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KR19990081362A - Medicinal soap composition containing natural fig isolate - Google Patents

Medicinal soap composition containing natural fig isolate Download PDF

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KR19990081362A
KR19990081362A KR1019980015245A KR19980015245A KR19990081362A KR 19990081362 A KR19990081362 A KR 19990081362A KR 1019980015245 A KR1019980015245 A KR 1019980015245A KR 19980015245 A KR19980015245 A KR 19980015245A KR 19990081362 A KR19990081362 A KR 19990081362A
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extract
chloroform
soap
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butanol
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KR100512285B1 (en
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성 렬 류
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22Organic compounds, e.g. vitamins
    • C11D9/38Products in which the composition is not well defined
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/02Compositions of detergents based essentially on soap on alkali or ammonium soaps
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22Organic compounds, e.g. vitamins
    • C11D9/26Organic compounds, e.g. vitamins containing oxygen

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Biotechnology (AREA)
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  • Microbiology (AREA)
  • Mycology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 알칼리금속비누베이스에 승정 도우핀(Masui Dauphine), 봉래시 또는 화이트제아노종의 무화과 열매 또는 잎의 용매 추출분리물 0.05 내지 25 중량% 및 안정화제 0.1 내지 5.0 중량%를 함유함을 특징으로 하는 약용비누조성물에 관한 것이다. 본 발명의 약용비누조성물은 독성이나 부작용없이 피부무좀 및 진균 그리고 향균 등의 치료효과가 우수하다.The present invention is characterized in that the alkali metal soap base contains 0.05 to 25% by weight of the solvent extract isolate of fig fruit or leaves of Masui Dauphine, Bonsi or Whitezeano species, and 0.1 to 5.0% by weight of stabilizer. It relates to a medicinal soap composition. Medicinal soap composition of the present invention is excellent in the therapeutic effect of skin athlete's foot and fungus and antibacterial without toxic or side effects.

Description

천연 무화과 분리성분을 함유한 약용비누 조성물Medicinal soap composition containing natural fig isolate

본 발명은 천연무화과 분리성분을 함유한 향진균성 및 향균성을 갖는 약용비누 조성물에 관한 것이다.The present invention relates to a medicinal soap composition having antifungal and antifungal properties containing a natural fig separation component.

무화과는 오랜 전통식품으로 농약을 전혀 사용하지 않는 완전한 무공해 과일로 성인병 예방과 밀접한 관계가 있는등 식품학적 가치가 뛰어나며 무화과에 풍부하게 포함되어 있는 피신(Ficine)과 미네랄 등의 여러 가지 항미생물 활성물질이 많이 존재하는 것으로 알려져 있다. 무화과는 무좀 및 구충제로도 활용되고 있으며 또한 무화과 잎에도 많은 활성물질이 존재한다. 그러나 무화과 잎이나 열매를 추출하고 약리활성물질을 분리하여 각 활성물질에 대한 항미생물 활성을 측정하여 천연 항미생물인 물질을 직접 비누베이스에 이용하여 비누제제를 제조하는 기술은 아직까지 전혀 시도된 바 없다.Fig is a long-established traditional food that has no pesticides at all and is a completely pollution-free fruit. It is closely related to the prevention of adult diseases. It has excellent food value and contains various antimicrobial active substances such as ficine and minerals. This is known to exist a lot. Figs are also used as athlete's foot and insect repellent, and there are many active substances in fig leaves. However, no technique has been attempted to manufacture soap preparations by extracting fig leaves or berries and separating pharmacologically active substances to measure antimicrobial activity of each active substance and using natural antimicrobial substances directly in the soap base. none.

특히 항진균제로는 화학합성 요법제가 다수를 차지하고 있으며, 이들중 한 예로 쟌센사에서 개발한 케토코나졸 및 이트라코나졸등은 칸디나 및 피부 사상균에 의한 백선(무좀), 지루성 피부염, 완선, 전풍 등에 적용하는 광범위 항진균제로서 심재성 진균증 그리고 표재성 진균증에도 효과가 탁월한 것으로 알려져 있다(미합중국 특허 제 4,335,125 호 참조). 또한 국소 투여에 의한 진균성 피부 질환 치료에 적합한 약학적 조성물, 특히 극소 적용 약제 조성물로서 용액제, 페이스트제, 연고제등의 조성물 및 화장품류, 즉 스킨 밀크로숀 등의 조성물 제제가 공지되어 있다(한국 특허 공개 제 90-17590호). 그러나, 이러한 화학합성 제제들은 진균간염이 혈관 분포가 적거나 또는 전혀 없는 손톱 및 발톱, 피부 또는 모발 등에 발생하므로 충분한 양의 약물을 분포 및 축적시키기 곤란하며, 심재성 진균증 같은 경우 약물이 깊이 투과시키기 어렵고 또 이러한 합성 물질들은 케토코나졸을 장기간에 걸쳐 경구 투여하게 되면 간독성과 위장장애 등 부작용이 유발되며, 많은 항진균제제들이 일반적으로 비극성물질로 극성인 물이나 극성용매에는 녹지 않는등의 문제점이 있다.In particular, chemosynthetic therapies account for a large number of antifungal agents. Among them, ketoconazole and itraconazole, developed by Texen, are widely used for antifungal agents such as ringworm (athlete), seborrheic dermatitis, sensitization, and sensitization caused by Candina and dermatophytes. It is also known to be effective against cardiac fungi and superficial fungi (see US Pat. No. 4,335,125). In addition, pharmaceutical compositions suitable for the treatment of fungal skin diseases by topical administration, in particular, compositions of solutions such as solutions, pastes, ointments, and cosmetics, that is, skin milk croshon, etc. are well known as microscopic application pharmaceutical compositions (Korea Patent Publication No. 90-17590). However, these chemical synthetic agents are difficult to distribute and accumulate in a sufficient amount of drugs because fungal hepatitis occurs in nails and toenails, skin or hair with little or no blood vessel distribution, and in case of heart disease, it is difficult to penetrate deeply. In addition, such synthetic materials cause side effects such as hepatotoxicity and gastrointestinal disorders when orally administered ketoconazole over a long period of time, and many antifungal agents are generally nonpolar and are insoluble in polar water or polar solvents.

다른한편, 국소적용 약제 조성물로서 이들 약제 조성물은 피부의 외부가 넓은 경우 많은 양의 약물이 요구되며, 바르는 양에 따라서는 피부질환 백선등에는 국소적으로 적용하기가 곤란한 점이 있으며 이물감 및 불쾌감을 야기시키고, 적용후 점성이 높은 반고형제의 경우(예:연고제, 크림제) 피부에 잔존하는 약제 조성물이 피복물에 달라 붙어서 불쾌감을 일으키는 문제점이 있다.On the other hand, as a topical pharmaceutical composition, these pharmaceutical compositions require a large amount of drugs when the outside of the skin is large, and depending on the amount applied, it is difficult to apply topically to a ringworm such as skin disease, causing foreign body feelings and discomfort. In the case of semi-solid high viscosity (for example, ointment, cream) after application, there is a problem that the pharmaceutical composition remaining on the skin clings to the coating, causing discomfort.

그외에, 기존의 알칼리 금속 비누는 각종 이물과 세균류에 대한 세정 작용은 있으나, 진균류 및 항균류에 기인한 각종 피부 질환에 대한 치료 효과는 거의 기대 할 수 없다. 그리고 화학합성 요법제로 알려진 케토코나졸과 이트라코나졸 등의 진균제를 이용한 제제들이 개발되고 있으나, 이들역시 장기간 동안 사용할 때 피부에 부작용이 있을 수 있으며 극성에 대한 용해도면에서 현저하게 난용성으로 특히 샴푸,액체비누등에서 이물질출현등 불쾌감이 있을수 있으며 불균일성 형상으로 약효 등을 충분히 발휘할 수 없다. 만약 이러한 제제를 비누에 적용한다 해도 물에 극히 난용성인 화합물로 약효는 응집에 따른 국한적 범위를 벗어나지 못 할 것으로 볼 수 있다.In addition, the existing alkali metal soap has a washing action against various foreign substances and bacteria, but the therapeutic effect against various skin diseases due to fungi and antibacterial can hardly be expected. In addition, preparations using fungicides such as ketoconazole and itraconazole, which are known as chemotherapy agents, have been developed, but these may also have side effects on the skin when used for a long time, and are particularly poorly soluble in polar solubility, especially in shampoos and liquid soaps. There may be unpleasant feelings such as foreign substance appearance, and it may not be able to exert its effects sufficiently due to the non-uniform shape. If these formulations are applied to soaps, the compounds are extremely poorly soluble in water, and their efficacy cannot be exceeded due to the aggregation.

이에 본발명자는 전술한 종래의 국소적용 약제 조성물의 문제점을 해결하기 위해 예의연구한 결과, 기존의 알카리 금속 비누에 천연과일로 먹을수 있는 무화과열매나 잎에서 강력한 항진균성분 및 항균성분을 추출분리하여 얻은 분획물질을 적용시킴으로써 독성이나 부작용없이 피부 무좀 및 진균 그리고 항균증의 치료 효과를 나타낼 수 있음을 밝혀내고 본 발명을 완성하게 되었다.Accordingly, the present inventors have made a thorough study to solve the problems of the conventional topical pharmaceutical composition described above, and obtained by extracting and separating strong antifungal and antibacterial ingredients from fig fruits or leaves that can be eaten as natural fruits in conventional alkali metal soaps. The present invention has been completed by discovering that fractional substances can be used to treat skin athlete's foot fungus and fungi and antibacterial effects without toxicity or side effects.

제 1도는 무화과 열매의 추출 및 분리 공정을 나타낸다.Figure 1 shows the extraction and separation process of the fig fruit.

제 2도는 무화과 잎의 추출 및 분리공정을 나타낸다.2 shows the extraction and separation of fig leaves.

본 발명은 알칼리금속비누베이스에 승정 도우핀(Masui Dauphine), 봉래시 또는 화이트제아노종의 무화과 열매 또는 잎의 용매 추출분리물 0.05 내지 25 중량% 및 안정화제 0.1 내지 5.0 중량%를 함유함을 특징으로 하는 약용비누조성물에 관한 것이다.The present invention is characterized in that the alkali metal soap base contains 0.05 to 25% by weight of the solvent extract isolate of fig fruit or leaves of Masui Dauphine, Bonsi or Whitezeano species, and 0.1 to 5.0% by weight of stabilizer. It relates to a medicinal soap composition.

본 발명은 무화과 잎이나 열매를 용매를 이용하여 분획추출 및 분리한 화합물을 알칼리금속비누베이스에 적용하여 약용 비누를 제조하는 것이다. 본 발명에서 사용되는 무화과 잎이나 열매는 시료 채취시기와 추출농축 온도가 중요하다. 바람직하게는 무화과가 나오는 전 계절의 과일과 잎을 이용하며, 보다 국한적으로는 6-10월 등 모든 완숙과일과 미숙과일인 무화과 열매와 무화과 잎을 이용하는 것이 효과적이다. 바람직하게는 저온인 20-70℃ 범위의 온도에서 감압농축한다.The present invention is to prepare a medicated soap by applying the compounds extracted and separated from the fig leaf or fruit using a solvent to the alkali metal soap base. Fig leaf and fruit used in the present invention is the sampling time and the extraction concentration is important. It is preferable to use fruits and leaves of all seasons with figs, and more particularly, to use fig fruits and fig leaves which are all ripe fruits and immature fruits such as June and October. It is preferably concentrated under reduced pressure at a low temperature of 20-70 ℃ range.

구체적으로는, 천연물질인 무화과 열매 또는 잎을 유기용매인 메탄올로 침적법, 압착법 또는 분쇄법 등에 의해 추출시켜 혼합추출물을 얻고, 이를 유기용매인 에틸아세테이트, n-부탄올, 에틸에테르, 핵산, 메칠렌클로라이드 또는 물로 각각 추출하여 분획추출물을 얻고, 또한 이를 연속방법으로 수포화 부탄올로 pH 2-6.5 인 산성용매 또는 pH 7.5-10인 알칼리 용매중에서 온도 30-90℃에서 행하고, 보다 바람직하게는 50-70℃의 온도에서 2-36시간 동안 용매의 종류에 따라 분획 추출하여 단백질 및 당을 선택적으로 제거하여 조성량의 효율을 높일 수 있다. 또한 카본처리로 탈색을 하고 용액을 알카리 및 산으로 중화시키고 이를 유기용매인 에틸아세테이트, n-부탄올, 에틸에테르, 핵산, 클로로포름, 메칠렌클로라이드, 물을 통하여 분리 분획 활성물질을 얻고 이를 칼럼 크로마토그래피-고형 충진제로서 실리카겔(SiO2),산화알루미나(Al2O3) 그리고 전개용매(클로로포름:부탄올=70:30, 메탄올, 에틸아세테이트:클로로포름:=70:30, n-부탄올:클로로포름:핵산=30:60:10, 클로로포름:메탄올=70:30, n-부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)를 이용하여 추출분리된 각 분리물질 즉 도면 제 1도 및 2도에 기재된 화합물 A, B, C, D, E, F, G, a, b, c, d, e, f, g를 주 원료로 사용한다.Specifically, the fig fruit or leaf which is a natural substance is extracted with methanol, which is an organic solvent, by dipping, pressing, or grinding, to obtain a mixed extract, which is an organic solvent, ethyl acetate, n-butanol, ethyl ether, nucleic acid, Extraction is carried out with methylene chloride or water, respectively, to obtain a fraction extract, which is also carried out in a continuous manner in an acidic solvent having a pH 2-6.5 or an alkaline solvent having a pH of 7.5-10 with saturated butanol at a temperature of 30-90 캜, more preferably. Fractional extraction is performed depending on the type of solvent for 2 to 36 hours at a temperature of 50-70 ℃ to selectively remove proteins and sugars to increase the efficiency of the amount of the composition. In addition, decolorization was carried out by carbon treatment and the solution was neutralized with alkali and acid, and the separated fraction active material was obtained through organic solvents, ethyl acetate, n-butanol, ethyl ether, nucleic acid, chloroform, methylene chloride and water, which were then subjected to column chromatography. Silica gel (SiO 2 ), alumina oxide (Al 2 O 3 ) and developing solvent (chloroform: butanol = 70: 30, methanol, ethyl acetate: chloroform: = 70: 30, n-butanol: chloroform: nucleic acid = 30:60:10, chloroform: methanol = 70: 30, n-butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50: 50) And compounds A, B, C, D, E, F, G, a, b, c, d, e, f, g described in FIG. 2 are used as the main raw materials.

본 발명에 따르면, 무화과 열매 또는 잎을 유기용매인 메탄올을 이용하여 침적법, 압착법 또는 분쇄법등으로 추출하여 혼합 추출물을 얻고, 이를 각 유기용매를 이용 분획 추출물을 얻고, 또 연속방법으로 이를 칼럼 크로마토그래피를 이용 유기용매인 에틸아세테이트, n-부탄올, 에틸에테르, 핵산, 클로포름, 메칠렌클로라이드, 물을 통하여 상기 혼합용매 및 단일 용매를 이용하여 추출분리된 각 분리물질을 안정화제와 함께 배합하여 약용비누 조성물을 제조한다.According to the present invention, the fig fruit or leaf is extracted by dipping, pressing or pulverizing with an organic solvent, methanol, to obtain a mixed extract, to obtain a fraction extract using each organic solvent, and to obtain a column extract in a continuous method. Using chromatography, the organic solvents, ethyl acetate, n-butanol, ethyl ether, nucleic acid, chloroform, methylene chloride, and water, are separated from each other using the mixed solvent and a single solvent. To prepare a medicated soap composition.

본 발명의 약용비누조성물에서 무화과 열매 또는 잎의 유기용매 추출분리물은 알칼리 금속 비누에 0.05 내지 25중량부, 바람직하게는 0.1 내지 12 중량부 첨가하는 것이 좋다. 무화과 분리 성분를 0.05 중량부 이하로 첨가하는 경우는 피부질환 치료 효과가 미약하고, 25중량부 이상 사용하는 경우에는 비누제형의 형성이 어려우며 더 이상의 항진균 비누효과를 기대할 수 없다.In the medicinal soap composition of the present invention, the organic solvent extract isolate of the fig fruit or leaf is preferably added in an amount of 0.05 to 25 parts by weight, preferably 0.1 to 12 parts by weight, to the alkali metal soap. When the fig separation component is added at 0.05 parts by weight or less, the effect of treating skin diseases is insignificant, and when it is used at 25 parts by weight or more, it is difficult to form a soap formulation and no antifungal soap effect can be expected.

본 발명에 따른 약용비누 조성에 있어서 알카리 금속비누는 무화과 자체에 함유하고 있는 칼슘염 지방산을 혼합하여 40중량부 까지 혼합 가능하다. 알칼리금속 비누는 탄소 원자수 10 내지 25개인 지방산의 알칼리 금속염이며, 여기서 지방산 야자유, 무화과유, 피마자유, 올리브유, 팜유, 대두유, 팜핵유 등 식물 유지와 우지, 양지, 돈지, 어유 등 동물유지로부터 얻는다. 알칼리 금속은 나트륨 또는 칼륨으로 단독 또는 혼합으로 지방산을 중화시켜 알칼리 금속 비누를 제조한다.Alkali metal soap in the medicated soap composition according to the present invention can be mixed up to 40 parts by weight by mixing the calcium salt fatty acid contained in the fig itself. Alkali metal soaps are alkali metal salts of fatty acids having 10 to 25 carbon atoms, from which fatty acid palm oil, fig oil, castor oil, olive oil, palm oil, soybean oil, palm kernel oil and other vegetable oils and fats, oil, pig oil, fish oil, etc. Get Alkali metals neutralize fatty acids either alone or in admixture with sodium or potassium to produce alkali metal soaps.

본 발명의 약용비누 조성물은 유효 성분인 항진균 및 항균성이 있는 무화과 분리 성분의 안정화를 위하여 안정화제를 사용할 수 있다. 안정화제는 비타민 C, 구연산, 구연산 나트륨, 사과산, 탄산나트륨, 중조, 치오황산나트륨, 중아황산나트륨, 치오우레아, 토코페롤, 초산 토코페롤, 아스코르빈산 나트륨, 무수나트륨 비설파이트, 무수나트륨 설파이트, 이미드우레아, 글루타치온, 폴리페놀, 부틸화하이드록시 아니솔, 부틸화 하이드록시 톨루엔, 아스코르빌 팔미테이트, 아스코르빌 올레에이트, 폴리소르베이트 80, 올레인산, D·B·A(알킬벤젠설폰산) 중에서 선택된 1종 또는 2종 이상을 사용한다.The medicated soap composition of the present invention may use a stabilizer for the stabilization of the anti-fungal and antimicrobial fig separation component of the active ingredient. Stabilizers include vitamin C, citric acid, sodium citrate, malic acid, sodium carbonate, sodium bicarbonate, sodium thiosulfate, sodium bisulfite, thiourea, tocopherol, tocopherol acetate, sodium ascorbate, anhydrous sodium bisulfite, sodium sulfite, imideurea, Selected from glutathione, polyphenol, butylated hydroxy anisole, butylated hydroxy toluene, ascorbyl palmitate, ascorbyl oleate, polysorbate 80, oleic acid, D.B.A (alkylbenzenesulfonic acid) Use 1 type, or 2 or more types.

본 발명의 약용 비누 조성물은 안정화제는 0.1 내지 5.0중량부, 바람직하게는 0.1 내지 2.0 중량부 함유하는 것이 좋다. 안정화제를 0.1중량부 이하 사용하는 경우는 충분한 안정화 효과를 기대 할 수 없으며, 5.0중량부 이상 사용하는 경우는 피부자극 등 부작용이 발생하며 안정화 효과가 작아진다.The pharmaceutical soap composition of the present invention preferably contains 0.1 to 5.0 parts by weight, preferably 0.1 to 2.0 parts by weight. When the stabilizer is used in an amount of 0.1 parts by weight or less, sufficient stabilization effect cannot be expected, and when used in an amount of 5.0 parts by weight or more, side effects such as skin irritation occur and the stabilization effect is small.

본 발명의 약용비누 조성물은 또한 화장비누에 일반적으로 사용하는 담체 성분들을 함유할 수 있다. 예를들어 금속이온 봉쇄제를 약 0.2중량부 이하로 첨가하고, 향료, 염료, 안료 등을 약 6.0중량부 이하의 수준으로 첨가할 수 있다. 본 발명에 따른 약용비누 조성물은 일반적인 비누 제조 방법에 따라 제조할 수 있다. 예를들어 일정한 혼합기에 수분이 8 내지 25 중량부 함유되어 있는 화장비누 베이스를 넣고 유효 성분인 항진균 및 항균성분이 있는 무화과 분리성분을 넣고 향료, 염료 및 기타 첨가제를 넣은 후 교반기를 이용하여 혼합하면서 안정화제를 1종 또는 2종 이상을 혼합한 다음 압출, 성형 및 절단하여 제조할 수 있다.The medicated soap composition of the present invention may also contain carrier components commonly used in cosmetic soaps. For example, a metal ion sequestrant may be added at about 0.2 parts by weight or less, and flavors, dyes, pigments, and the like may be added at a level of about 6.0 parts by weight or less. The medicated soap composition according to the present invention can be prepared according to a general soap manufacturing method. For example, put a makeup soap base containing 8 to 25 parts by weight of water in a constant mixer, add figs containing antifungal and antibacterial ingredients as active ingredients, add fragrances, dyes and other additives, and then stir with a stirrer. The agent may be prepared by mixing one kind or two or more kinds and then extruding, molding and cutting.

화장비누 베이스는 일반적으로 사용되고있는 천연 유지인 팜유(palm oil)의 나트륨염과 칼륨염이 사용되며, 바람직하게는 탄소수가 10내지 25개인 팜지방산유 나트륨염과 칼륨염이 사용된다. 본 발명에 따른 약용비누 조성물에서는 수분 8.0 내지 25.0중량부 함유된 화장비누 베이스(soap base)를 약 50 내지 98중량부를 사용한다.Soap base and sodium salt and potassium salt of palm oil (palm oil) which is a commonly used natural fat is used, preferably palm fatty acid sodium and potassium salts having 10 to 25 carbon atoms are used. In the medicated soap composition according to the present invention, about 50 to 98 parts by weight of a soap base (soap base) containing 8.0 to 25.0 parts by weight of water is used.

본 발명에 따른 약용비누 조성물은 호호바유, 글리세린 폴리에틸렌글리콜(분자량 4000), 에틸렌글리콜 같은 보습제를 0.1 내지 5중량부 함유할 수 있다.The medicated soap composition according to the present invention may contain 0.1 to 5 parts by weight of a moisturizing agent such as jojoba oil, glycerin polyethylene glycol (molecular weight 4000), ethylene glycol.

본 발명에 따른 약용비누 조성물은 1일-2일간 3회, 3-4일간 2,3회 진균류에 기인한 피부 질환에 국소적으로 적용하면 피부진균증 치료 효과가 나타나며 계속 15일간 정도 사용하면 진균류에 기인한 대부분의 피부 질환에 탁월한 치료 효과를 나타낸다.The medicated soap composition according to the present invention is applied to skin diseases caused by fungi three times a day, two days three days, and two or three times three to four days. It has an excellent therapeutic effect on most skin diseases caused.

본 발명에 따른 약용비누 조성물은 일반 화장비누와 같이 매일 사용할 수 있으며, 특히 세정효과와 피부세균증 그리고 피부 진균증의 치료를 동시에 겸할 수 있고 1회 사용량이 매우 적으면서 지속적으로 환부에 사용하기가 간편하여서 치료 효과 및 사용성에서 상당히 개선된 새로운 형태의 두발 및 두피의 비듬 과 피부 진균 및 세균 치료제라고 할 수 있다.The medicated soap composition according to the present invention can be used every day as a general cosmetic soap, and in particular, it can simultaneously combine the cleaning effect and the treatment of skin bacteremia and skin fungus, and is easy to use continuously in the affected area with very low one-time use. It is a new form of dandruff and scalp and skin fungal and bacterial treatments that has significantly improved the therapeutic effect and usability.

본 발명에 따른 약용비누조성물은 샴푸, 액체비누, 린스, 항미생물제, 어류병치료제, 어류사료첨가제, 식료품가공첨가제, 무공해식물재배시 농약대체물, 무좀치료제, 피부연고제 또는 피부질환치료제 등의 제형으로 유용하게 사용될 수 있다.Medicinal soap composition according to the present invention is a shampoo, liquid soap, rinse, antimicrobial agent, fish disease treatment agent, fish feed additive, food processing additives, pollution-free plant during planting, pesticide substitute, athlete's foot treatment, skin ointment or skin disease treatment It can be usefully used.

이하, 실시예에 의거하여 본 발명을 구체적으로 설명하지만, 이들 실시예로 본 발명의 기술적 범위가 제한되는 것은 아니다.Hereinafter, although this invention is demonstrated concretely based on an Example, the technical scope of this invention is not restrict | limited to these Examples.

실시예Example

1) 실험시료1) Experimental sample

무화과(Ficus carica Linn)는 전남 영암군 삼호면 산호리 인근 지역의 특산물로 재배 생산되고 있는 (Ficus carica Linn. var. hortensis Shinn) 승정도우핀(Masui Dauphine)과, 봉래시 ,그리고 화이트제노아종의 잎이나 열매를 각각 채취하여 실험 하였다.Fig (Ficus carica Linn) is a cultivar produced in the area near Sanho-myeon, Samho-myeon, Yeongam-gun, Jeollanam-do (Ficus carica Linn.var.hortensis Shinn) and the leaves or berries of Masui Dauphine, Bongsi, and White Genoa species. Each was collected and tested.

2) 용매를 이용한 무화과 추출방법 및 용액분획2) Fig extraction method and solution fraction using solvent

무화과 생과 및 습체잎을 각각 별도로 10kg을 기준하여 그대로 또는 분쇄하여 무화과 생과와 무화과 잎은 메탄올 또는 에탄올로 10배 분량의 각 용매를 가하여 상온에서 약 3개월동안 침적법, 압착법 또는 분쇄법으로 추출하고 Bchner funnel로 흡인 여과하여, 추출액을 혼합하여 25∼50℃에서 감압농축기 (Bchi RE 121,Switzerland)를 사용하여 메탄올을 제거한 후 시료로 하여 냉장실에 보관하면서 사용하였다.Fig fig raw fruits and wet leaves are separately or ground based on 10 kg each, and fig raw fruits and fig leaves are extracted by dipping, pressing or grinding for about 3 months at room temperature by adding 10 times the amount of each solvent with methanol or ethanol. The resultant was filtered by suction with a Bchner funnel, and the extracts were mixed and the methanol was removed using a reduced pressure concentrator (Bchi RE 121, Switzerland) at 25 to 50 ° C., which was used as a sample and stored in a refrigerator compartment.

상기 방법으로 메탄올 추출물(생과) 132g을 기준하여 도면1과 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 CHCl3, CH2Cl2, EtOAc, CH3CN, 에테르를 선택적으로 이용하여 1 L씩 3회 추출 후 농축하고 계속해서 수층은 수포화부탄올로 용매 분획한 다음 농축하여 각각 1.2g씩 분획물을 얻었으며 최종적으로 분획물 28.4g을 얻어 시료로하여 칼럼크로마토그래피로 분리하였다. 또 메탄올 (잎)132g을 기준하여 도면2와 같이 용매 분획하였다. 즉 ,무화과 추출물 분획여두에서 MeOH, n-BuOH, CH3CN, CHCl3, EtOAc,CH2Cl2을 선택적으로 이용하여 1 L씩 3회 추출 농축하고 계속해서 수층은 수포화-부탄올로 용매 분획한 다음 농축하여 최종적으로 분획물 5.6g을 얻고, 이를 칼럼크로마토그래피를 이용하여 분리하였다.Solvent fractionation was performed based on the methanol extract (fresh fruit) 132g by the above method. That is, extract extract fractions using CHCl 3 , CH 2 Cl 2 , EtOAc, CH 3 CN, ether three times 1 L each extract and concentrated, and then the aqueous layer was solvent fractionated with saturated butanol and then concentrated 1.2 g of each fraction was obtained, and finally 28.4 g of fractions were obtained as samples and separated by column chromatography. The solvent was fractionated as shown in FIG. 2 based on 132 g of methanol (leaf). That is, the extract extract fractions were extracted and concentrated three times by 1 L each time selectively using MeOH, n-BuOH, CH 3 CN, CHCl 3 , EtOAc, CH 2 Cl 2 and then the aqueous layer was solvent-fractionated with saturated butanol. And then concentrated to give 5.6 g of fractions which were then separated using column chromatography.

3) 무화과 약리활성 성분 분리를 위한 칼럼 크로마토그래피(column chromatography)를 위하여서는 역상 크로마토그래피(C18 Lobacolumn) 및 순상 크로마토그래피(silicagel 60)을 사용하였다. 도면 제 1도는 무화과열매의 추출 및 분리 공정을 나타내며, 제 2도는 무화과잎의 추출 및 분리 공정을 나타낸다.3) Reversed phase chromatography (C18 Lobacolumn) and normal phase chromatography (silicagel 60) were used for column chromatography for separation of pharmacologically active ingredients. 1 shows the extraction and separation process of fig fruit, and FIG. 2 shows the extraction and separation process of fig leaf.

실시예 1 : [A], [a]의 추출공정Example 1: Extraction process of [A], [a]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 및 습체잎 각각 별도로 10kg을 기준하여 무화과 생과와 무화과 잎을 메탄올로 1.5-10배 분량의 각 용매를 가하여 상온에서 약 2 개월 동안 침적법으로 추출하고 Bchner funnel로 흡인 여과하면 충분히 무화과 쥬스가 추출되어 유리된다. 추출 효율을 높이기 위해서는 20-70일 정도까지 추출하였다. 추출액을 무화과와 분리한 다음 이를 30-60℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 메탄올을 제거한 후 (열매-323.5g, 잎-267.0g) 액상 시럽상태의 진갈색 점성 화합물[A], [a]을 각각 얻었으며, 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs cleanly, remove the water, extract the fig raw fruits and the fig leaves with methanol by adding 1.5-10 times the amount of each solvent, based on 10 kg of the fig raw fruits and the wet leaves. Suction filtration with a Bchner funnel extracts and releases enough fig juice. In order to increase the extraction efficiency was extracted up to about 20-70 days. The extract was separated from the figs and then methanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) at 30-60 ° C. (fruit-323.5 g, leaf-267.0 g) and dark brown viscous compound in liquid syrup [A] , [a] were obtained, respectively, and used as samples as being stored in the refrigerator compartment.

실시예 2: [A], [a]의 추출공정Example 2: Extraction process of [A], [a]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 및 습체잎 각각 별도로 10kg을 기준하여 무화과 생과와 무화과 잎을 실온에서 n-부탄올로 1.5-10배 분량의 각 용매를 가하여 상온에서 약 2 개월 동안 침적법으로 추출하고 Bchner funnel로 흡인 여과하면 충분히 무화과 쥬스가 추출되어 유리된다. 추출 효율을 높이기 위해서는 20-70일 정도까지 추출하였다. 추출액을 무화과와 분리한 다음 증류수 400㎖를 넣고 약 3시간 동안 실온에서 추출한다. 이를 걸러서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 부탄올을 제거한 후 (열매-220g, 잎-210g) 액상 시럽상태의 진갈색 점성 화합물[A], [a]을 각각 얻었으며, 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs, the water is removed, and the fig raw fruits and fig leaves are submerged at room temperature for about 2 months by adding 1.5-10 times the amount of each solvent with n-butanol at room temperature based on 10 kg of fig raw fruits and wet leaves. Extraction by means of the method and suction filtration with Bchner funnel sufficiently extracts and releases the fig juice. In order to increase the extraction efficiency was extracted up to about 20-70 days. The extract is separated from the figs, and 400 ml of distilled water is added and extracted at room temperature for about 3 hours. After filtering, butanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) (fruit-220g, leaf-210g) to obtain a dark brown viscous compound [A] and [a] in liquid syrup. Each was used while storing in a refrigerator.

실시예 3: [A], [a]의 추출공정Example 3: Extraction process of [A], [a]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 및 습체잎 각각 별도로 10kg을 기준하여 무화과 생과와 무화과 잎을 메탄올로 1.5-10배 분량의 각 용매를 가하여 40-50℃에서 6시간동안 강제 앞착법으로 추출하고 Bchner funnel로 흡인 여과하면 무화과 쥬스가 추출되어 유리된다. 추출 효율을 높이기 위해서는 10시간이상 정도 추출함이 바람직하다. 이를 냉각시키고 추출액을 무화과와 분리한 다음 이를 30-60℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 메탄올을 제거한 후 (열매-351g, 잎-310g) 액상 시럽상태의 진갈색 점성 화합물[A], [a]을 얻었으며 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs cleanly, remove the water, and apply the fresh raw figs and fig leaves 1.5-10 times of each solvent with methanol based on 10 kg of fig raw fruits and wet leaves separately, and force them for 6 hours at 40-50 ℃. Extraction and suction filtration with Bchner funnel extract and release the fig juice. In order to increase the extraction efficiency, it is preferable to extract about 10 hours or more. The mixture was cooled, the extract was separated from the fig, and the methanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) at 30-60 ° C. (fruit-351 g, leaf-310 g). A dark brown viscous compound in liquid syrup [A ], [a] were obtained and used as samples as the samples were stored in the refrigerator compartment.

실시예 4: [A], [a]의 추출공정Example 4: Extraction process of [A], [a]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 10㎏을 기준하여 무화과 생과을 노르말부탄올로 1.5-2배 분량의 용매를 가하여 상온에서 압착법으로 용매와 함께 착즙하고 Bchner funnel로 흡인 여과하고 착즙액을 무화과와 분리한 다음 이를 30-60℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 노르말 부탄올을 제거한 후 312g의 액상 시럽상태의 진갈색 점성 화합물[A], [a]을 얻었으며, 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs cleanly, remove the water, add 1.5-2 times the amount of figs with normal butanol, and extract the fresh fruits with normal butanol at room temperature, compress them with solvent, suction filtration with Bchner funnel, and extract juice. After separating from the fig and using a depressurizer (Bchi RE 121, Switzerland) at 30-60 ℃ to remove the normal butanol, 312g of a liquid syrup-like dark brown viscous compound [A], [a] was obtained. Each was used while storing in the refrigerator compartment.

실시예 5: [A]의 추출공정Example 5: Extraction process of [A]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 10㎏을 기준하여 무화과 생과을 에탄올로 1.5-2배 분량의 각 용매를 가하여 상온에서 앞착법으로 용매와 함께 착즙하고 Bchner funnel로 흡인 여과하고 착즙액을 무화와 분리한 다음 이를 30-60℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 노르말 부탄올을 제거한 후 312g의 액상 시럽상태의 진갈색 점성 화합물[A]을 얻었으며, 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs cleanly, remove the water, add 1.5-2 times the amount of each fig of the fig raw fruit with ethanol, and juice it with the solvent by annealing at room temperature, suction filtration with Bchner funnel, and extract the juice. After separation with an atomized solution, normal butanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) at 30-60 ° C., and 312 g of a dark brown viscous compound [A] was obtained as a sample. Used while storing in.

실시예 6: [A]의 추출공정Example 6: Extraction process of [A]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 10㎏을 기준하여 무화과 생과을 에탄올로 1.5-2배 분량의 각 용매를 가하여 상온에서 침적법으로 실온에서 20일 이상 유기물질을 추출하고 이를 Bchner funnel로 흡인 여과하고 착즙액을 무화와 분리한 다음 이를 30-40℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 에탄올을 제거한 후 325g의 액상 시럽상태의 진갈색 점성 화합물[A]을 얻었으며, 이를 시료로 하여 각각 냉장실에 보관하면서 사용하였다.After washing the figs cleanly, remove water and add 1.5-2 times the amount of each fig fruit to ethanol based on the fig raw and 10 kg, extract organic materials at room temperature for 20 days or more by dipping at room temperature, and use Bchner funnel. The resultant was filtered by suction, the juice was separated from the fig, and the ethanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) at 30-40 ° C., whereby 325 g of a dark brown viscous compound [A] was obtained. Each sample was used while storing in a refrigerator compartment.

실시예 7: [B]의 추출공정Example 7: Extraction process of [B]

메탄올 추출물(생과) 132g을 기준으로 도면 제 1도와 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 CHCl31 L씩 3회 추출 한 다음 활성탄 2.2g을 이용 탈색하여 여과하고 여액을 농축하여 칼럼크로마토그래피(전개용매 n-부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)를 실시하여 고체 화합물 [B] 0.15g을 얻었다.The solvent was fractionated as shown in FIG. 1 based on 132 g of the methanol extract (fresh fruit). That is, extract 3 times 1 L each of CHCl 3 from the fig extract fraction, decolorized using 2.2 g of activated charcoal, and filtered. The filtrate was concentrated and column chromatography (developing solvent n-butanol: distilled water: chloroform = 10: 5: 80 and Chloroform: methanol = 50:50) was carried out to obtain 0.15 g of solid compound [B].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.89TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.89

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 1724(CO), 1653, 1450(C=C)IR spectral data IR (KBr), Cm-1: 1724 (CO), 1653, 1450 (C = C)

1H-NMR 스펙트럼 데이타 δ: 6.5 (1H, d, J=9. 6Hz, H-3), 6.9(1H, d, J=3. 2Hz, H-3'), 7.5(1H, s, H-8), 7.8(6H, s, H-5), 7.6(1H, d, J=1. 7Hz, H-2') 7.8(H, d, J=1. 7Hz, H-4) 1 H-NMR spectral data δ: 6.5 (1H, d, J = 9.6 Hz, H-3), 6.9 (1H, d, J = 3.2 Hz, H-3 '), 7.5 (1H, s, H -8), 7.8 (6H, s, H-5), 7.6 (1H, d, J = 1.7 Hz, H-2 ') 7.8 (H, d, J = 1.7 Hz, H-4)

Mass 스펙트럼은 이온 피크가 m/z186에서 나타나고 base피크가 m/z 131에서 그리고 fragment이온피크가 m/z168.9, 158,147,118.9에 나타났다.Mass spectra showed ion peaks at m / z186, base peaks at m / z 131, and fragment ion peaks at m / z168.9, 158,147, and 118.9.

실시예 8: [C]의 추출공정Example 8: Extraction process of [C]

메탄올추출물(생과) 132g을 기준하여 도면1.과 같이 용매 분획하였다. 즉 ,무화과 추출물 분획여두에서 CHCl31 L씩 3회 추출 한 다음 2.1g을 이용 탈색하여 여과하고 여액을 농축하여 칼럼크로마토그래피(전개용매 노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)를 실시하여 화합물 [C] 0.21g을 얻었다.Methanol extract (fresh fruit) based on 132g solvent fractionation as shown in Figure 1. That is, extract 3 times 1 L each of CHCl 3 from the fig extract fraction, and then decolorized and filtered using 2.1 g, and the filtrate was concentrated and column chromatography (developing solvent normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: Methanol = 50:50) to obtain 0.21 g of compound [C].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.44TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.44

IR 스펙트럼 데이타 (KBr), Cm-1 : 3013, 1679, 1416, 1324, 1200IR spectral data (KBr), Cm-1: 3013, 1679, 1416, 1324, 1200

실시예 9: [D]의 추출공정Example 9: Extraction process of [D]

실시예 1에 의한 방법으로 메탄올 추출물(생과) 132g을 기준하여 도면 제 1도와 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 클로로포름 400㎖에 넣고 추출하여 추출한 액을 감압농축하여 12g을 얻었다. 이를 다시 에테르 300㎖에 넣고 추출하여 추출된 화합물에 활성탄 1.2g을 이용 40℃에서 약 10분동안 교반하고 이를 여과하였다. 여액을 감압농축하고 다시 아세토나이트릴 300㎖로 추출하여 녹아나온 화합물에 활성탄 1.2g을 이용 40℃에서 약 10분동안 교반하고 이를 여과하였다. 여액을 농축하여 녹여 칼럼크로마토그래피(전개용매 노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)를 실시하여 결정화합물 [D] 0.28g을 얻었다.Solvent fractionation based on the methanol extract (fresh fruit) 132g by the method according to Example 1 as shown in FIG. That is, the extract was extracted with filtrate in 400 ml of chloroform and extracted and concentrated under reduced pressure to obtain 12 g. The mixture was added to 300 ml of ether again, and extracted with 1.2 g of activated carbon. The mixture was stirred at 40 ° C. for about 10 minutes and filtered. The filtrate was concentrated under reduced pressure, and extracted again with 300 ml of acetonitrile. Then, 1.2 g of the activated carbon was dissolved in the dissolved compound at 40 ° C. for about 10 minutes and filtered. The filtrate was concentrated and dissolved to perform column chromatography (developing solvent normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50:50) to obtain 0.28 g of crystalline compound [D].

TLC(전개용매: 콜로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.68TLC (developing solvent: coloform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.68

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 3500(OH), 2983(CH), 1650, 1400(C=C)IR Spectrum Data IR (KBr), Cm-1: 3500 (OH), 2983 (CH), 1650, 1400 (C = C)

1H-NMR 스펙트럼 데이타 δ: 1.0(mH,m), 3.3(1H,m,H-3), 5.3(1H,m,H-6) 1 H-NMR spectral data δ: 1.0 (mH, m), 3.3 (1H, m, H-3), 5.3 (1H, m, H-6)

Mass 스펙트럼은 이온 피크가 m/z 414 에서 나타나고 그리고 fragment이온피크가 m/z 303, 254, 213, 159, 146, 107, 95에 나타났다.Mass spectra showed ion peaks at m / z 414 and fragment ion peaks at m / z 303, 254, 213, 159, 146, 107 and 95.

실시예 10: [E]의 추출공정Example 10 Extraction of [E]

실시예 1에 의한 방법으로 메탄올 추출물(생과) 132g을 기준하여 도면 제 1도와 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 디클로로메탄 400㎖에 넣고 추출하였다. 불용화합물을 에틸아세테이트 300㎖에 넣고 추출하여 층 분리시키고 황산마그네슘 0.12g으로 건조시킨 다음 감압농축하여 시럽화합물[E]을 0.1g 얻었다.Solvent fractionation based on the methanol extract (fresh fruit) 132g by the method according to Example 1 as shown in FIG. That is, the extract was put into 400 ml of dichloromethane and extracted from the filtrate fraction. The insoluble compound was added to 300 ml of ethyl acetate, followed by extraction. The layers were separated, dried over 0.12 g of magnesium sulfate, and concentrated under reduced pressure to obtain 0.1 g of syrup compound [E].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.08TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.08

1H-NMR 스펙트럼 데이타 δ: 2.35(1H, t), 1.65(1H, m), 1.25(13H, m), 0.88(2H, t) 1 H-NMR spectral data δ: 2.35 (1H, t), 1.65 (1H, m), 1.25 (13H, m), 0.88 (2H, t)

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 3008, 2289(C-H), 1652(C=C), 1109, 1423, 1245IR spectral data IR (KBr), Cm-1: 3008, 2289 (C-H), 1652 (C = C), 1109, 1423, 1245

실시예 11: [F]의 추출공정Example 11: Extraction process of [F]

실시예 1에 의한 방법으로 메탄올 추출물(생과) 132g을 기준하여 도면 제 1도와 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 디클로로메탄 400㎖에 넣어서 추출하고, 불용화합물을 에틸아세테이트 300㎖을 넣고 추출하여 분리시켰다. 이때 불용화합물을 합하여 감압농축하여 칼럼크로마토그래피(전개용매 클로로포름:메탄올=90:10)를 실시하여 결정화합물 [F] 0.52g을 얻었다.Solvent fractionation based on the methanol extract (fresh fruit) 132g by the method according to Example 1 as shown in FIG. That is, the extract was extracted by adding 400 mL of dichloromethane in the fractional filter extract, and the insoluble compound was extracted by adding 300 mL of ethyl acetate. At this time, the insoluble compounds were combined and concentrated under reduced pressure, followed by column chromatography (developing solvent chloroform: methanol = 90: 10) to obtain 0.52 g of crystalline compound [F].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.03TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.03

IR 스펙트럼 데이타 IR(KBr), Cm-1 :3010, 2990(C-H), 1650, 1470(C=C), 1710(C=O)IR Spectrum Data IR (KBr), Cm-1: 3010, 2990 (C-H), 1650, 1470 (C = C), 1710 (C = O)

실시예 12: [G]의 추출공정Example 12 Extraction of [G]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 10kg을 기준하여 무화과 생과을 메탄올로 1.5-10배 분량의 각 용매를 가하여 상온에서 약 2 개월 동안 침적법으로 추출하고 Bchner funnel로 흡인 여과하면 충분히 무화과 쥬스가 추출되어 나오는데, 보다 추출 효율을 높이기 위해서 20-70일 정도까지 추출하였다. 추출액을 무화과와 분리한 다음 이를 30-60℃에서 감압농축기 (Bchi RE 121, Switzerland)를 사용하여 메탄올을 제거한 후 열매-323.5g, 잎-267.0g을 얻었다. 이를 시료로하여 메탄올 생과 추출물 132g을 기준하여 도면1.과 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, CHCl31L 씩 3회 추출 한 다음 불용성화합물 및 수층은 포화 염화나트륨, 또는 포화염화칼슘 용액을 이용 실온에서 수포화부탄올 300㎖X5로 추출한 다음 층 분리하여 황산마그네슘 1.0g을 넣고 40℃에서 10분간 잘 저어준 다음 이를 걸러서 유기용매를 감압농축하여 최종적으로 액상시럽형태의 농축물 28.4g을 얻었다. 이를 다시 칼럼크로마토그래피 (전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 무색침상결정 화합물 [G] 10.3g을 얻었다. 이를 HPLC칼럼과 UV로 측정한 결과 흡수파장은 233㎚이고 융점은 258-259℃이다.After washing the figs cleanly, remove the water, add 1.5-10 times the amount of fig raw fruits to methanol based on 10kg of figs, extract them by immersion method at room temperature for about 2 months, and filter them by suction filtration with Bchner funnel. Is extracted, it was extracted up to about 20-70 days in order to increase the extraction efficiency. The extract was separated from the figs, and then methanol was removed using a vacuum concentrator (Bchi RE 121, Switzerland) at 30-60 ° C. to obtain fruit-323.5g and leaves-267.0g. As a sample, the solvent was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the filtrate fraction of the fig extract, and extracted three times with 1 L of CHCl 3. The insoluble compound and the aqueous layer were extracted with saturated sodium chloride or saturated calcium chloride solution at room temperature with 300 mlX5 of saturated butanol, and the layers were separated. 1.0 g of magnesium sulfate was added thereto, the mixture was stirred well at 40 ° C. for 10 minutes, and the organic solvent was concentrated under reduced pressure. Finally, 28.4 g of a concentrate in the form of a liquid syrup was obtained. This was again performed by column chromatography (developing solvent = normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50:50) to give 10.3 g of colorless needles (G). This was measured by HPLC column and UV, and the absorption wavelength was 233 nm and melting point was 258-259 ° C.

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.01TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.01

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 2925, 28259(-C-H), 1721(C=O), 1679(C=C-C=O), 1642(C=C), 1542, 1549, 1387, 1262, 1071, 771IR Spectrum Data IR (KBr), Cm-1: 2925, 28259 (-CH), 1721 (C = O), 1679 (C = CC = O), 1642 (C = C), 1542, 1549, 1387, 1262 , 1071, 771

실시예 13: [G]의 추출공정Example 13: Extraction process of [G]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 생과 10kg을 기준하여 무화과 생과을 n-부탄올로 1.5-10배 분량의 각 용매를 가하여 실시예 2의 방법과 동일하게 압착법으로 착즙하고 Bchner funnel로 여과하여 노르말 부탄올을 제거한 후 열매-220g, 잎-212g을 얻었다. 이를 시료로하여 부탄올 생과 추출물 132g을 기준하여 도면 제 1도와 같이 용매 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, CHCl31L 씩 3회 추출 한 다음 불용화합물 및 수층은 포화 염화나트륨, 또는 포화염화칼슘 용액을 이용 실온에서 수포화부탄올 300㎖X5로 추출한 다음 층 분리하여 황산마그네슘 1.0g을 넣고 40℃에서 10분간 잘 저어준 다음 이를 걸러서 유기용매를 감압농축하여 최종적으로 액상시럽형태의 28.4g을 얻었다. 다시 이를 칼럼크로마토그래피 (전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 고체 화합물 [G]을 얻었다.After washing the figs cleanly, the water was removed, and the figs were extracted by compressing them in the same manner as in Example 2 by adding 1.5-10 times the amount of each solvent with n-butanol, and filtering with Bchner funnel. After removing normal butanol, fruit-220g and leaf-212g were obtained. As a sample, the solvent was fractionated as shown in FIG. 1 based on 132 g of butanol raw fruit extract. That is, 200 ml of distilled water was added from the filtrate fraction of the fig extract, and extracted three times with 1 L of CHCl 3 , and the insoluble compound and the aqueous layer were extracted with saturated sodium chloride or saturated calcium chloride solution at room temperature with 300 mlX5 of saturated butanol, and the layers were separated. 1.0 g of magnesium sulfate was added thereto, the mixture was stirred well at 40 ° C. for 10 minutes, and the organic solvent was concentrated under reduced pressure to obtain 28.4 g of a liquid syrup form. It was then subjected to column chromatography (developing solvent = normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50: 50) to give a solid compound [G].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.01TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.01

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 2925, 28259(-C-H), 1721(C=O), 1679(C=C-C=O), 1642(C=C), 1542, 1549, 1387, 1262, 1071, 771IR Spectrum Data IR (KBr), Cm-1: 2925, 28259 (-CH), 1721 (C = O), 1679 (C = CC = O), 1642 (C = C), 1542, 1549, 1387, 1262 , 1071, 771

실시예 14: [a]의 추출공정Example 14 Extraction of [a]

무화과를 깨끗이 세척한 후 물을 제거하고 무화과 습체잎 10kg을 기준하여 무화과 잎을 메탄올로 1.5-10배 분량의 용매를 가하여 상온에서 약 2 개월 동안 침적법으로 실시예1의 방법으로 추출하여 메탄올을 제거한 후 이 추출물 100g을 취해서 도면 제 2도와 같이 용액 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하여 이를 무수황산나트륨으로 탈수하고 걸러서 회수된 유기용매를 합하여 감압축하였다. 다시 이를 CHCl3150㎖씩 4회 추출하여 감압농축하여 칼럼크로마토그래피 (전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 고체 화합물 [a] 1.43g을 얻었다.After washing the figs cleanly, water was removed, and the fig leaves were extracted with the method of Example 1 by dipping at about room temperature for about 2 months by adding 1.5-10 times the amount of the solvent with methanol based on 10 kg of fig wet leaves. After removal, 100 g of the extract was taken and the solution was fractionated as shown in FIG. 2. That is, 200 ml of distilled water was added from the fig extract fraction filter, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times, and the layers were separated, dehydrated with anhydrous sodium sulfate, and the collected organic solvents were combined and concentrated under reduced pressure. Then, the mixture was extracted four times with 150 ml of CHCl 3, and concentrated under reduced pressure, followed by column chromatography (developing solvent = normal-butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50: 50) to give a solid compound [a]. 1.43 g was obtained.

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.94TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.94

실시예 15: [b]의 추출공정Example 15: Extraction process of [b]

실시예 11의 방법에 의해서 추출물 100g을 기준하여 도면 제 2도와 같이 용액 분획하였다. 즉 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하여 이를 무수황산나트륨으로 탈색하고 걸러서 회수된 유기용매를 합하여 감압농축하였다. 이를 다시 CHCl3150㎖씩 4회 추출하여 감압농축하였다. 그리고 칼럼크로마토그래피 (전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 화합물 [b] 1.43g을 얻었다.By the method of Example 11 based on 100g extract was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the extract extract filtrate, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times, and the layers were separated, decolorized with anhydrous sodium sulfate, and the organic solvents collected by filtration were concentrated under reduced pressure. It was extracted 4 times with 150 ml of CHCl 3 again and concentrated under reduced pressure. Then, column chromatography (developing solvent = normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50:50) was performed to obtain 1.43 g of compound [b].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.89TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.89

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 1724(CO), 1653, 1450(C=C)IR spectral data IR (KBr), Cm-1: 1724 (CO), 1653, 1450 (C = C)

1H-NMR 스펙트럼 데이타 δ: 6.5 (1H, d, J=9. 6Hz, H-3), 6.9(1H, d, J=3. 2Hz, H-3'), 7.5(1H, s, H-8), 7.8(6H, s, H-5), 7.6(1H, d, J=1.7Hz, H-2') 7.8(H, d, J=1.7Hz, H-4) 1 H-NMR spectral data δ: 6.5 (1H, d, J = 9.6 Hz, H-3), 6.9 (1H, d, J = 3.2 Hz, H-3 '), 7.5 (1H, s, H -8), 7.8 (6H, s, H-5), 7.6 (1H, d, J = 1.7 Hz, H-2 ') 7.8 (H, d, J = 1.7 Hz, H-4)

Mass 스펙트럼은 이온 피크가 m/z186에서 나타나고 base피크가 m/z 131에서 그리고 fragment이온피크가 m/z168.9, 158,147,118.9에 나타났다.Mass spectra showed ion peaks at m / z186, base peaks at m / z 131, and fragment ion peaks at m / z168.9, 158,147, and 118.9.

실시예 16: [c]의 추출공정Example 16: Extraction process of [c]

실시예 11의 방법에 의해서 추출물 100g을 기준하여 도면 제 2도와 같이 용액 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하여 이를 무수황산나트륨으로 탈색하고 걸러서 회수된 유기용매를 합하여 감압농축하여 이를 무수황산나트륨으로 탈수하고 걸러서 회수된 유기용매를 합하여 감압농축하여 12g을 얻었다. 이를 다시 실온에서 CHCl3150㎖씩 4회 추출하고 분리하여 수용액층을 모아 pH 2로 조절하고 실온에서 디클로로메탄으로 추출하여 층 분리한 다음 무수 황산마그네슘으로 탈수하고 걸러서 칼럼크로마토그래피 (전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 화합물 [c] 0.1g을 얻었다.By the method of Example 11 based on 100g extract was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the fig extract fraction filter, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times, and the layers were separated, decolorized with anhydrous sodium sulfate, filtered, and the recovered organic solvents were combined and concentrated under reduced pressure. The mixture was extracted four times at room temperature and extracted with 150 ml of CHCl 3 four times. Butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50: 50) was performed to obtain 0.1 g of the compound [c].

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=1TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 1

IR 스펙트럼을 분석한 결과 IR(KBr), Cm-1 : 1732(C=C), 1628, 1452(C=C)IR spectrum analysis shows IR (KBr), Cm-1: 1732 (C = C), 1628, 1452 (C = C)

1H-NMR 스펙트럼 데이타 δ: 4.29 (3H, s, OCH3), 6.28(1H, d, J=9. 8Hz, H-3'), 7.0(1H, d, J=2. 3Hz, H-3'), 7.3(1H, s, H-8), 7.6 (1H, d, J=2.4Hz, H-2'), 8.17(1H, d, J=9.7Hz, H-4) 1 H-NMR spectral data δ: 4.29 (3H, s, OCH 3 ), 6.28 (1H, d, J = 9.8 Hz, H-3 '), 7.0 (1H, d, J = 2.3 Hz, H- 3 '), 7.3 (1H, s, H-8), 7.6 (1H, d, J = 2.4 Hz, H-2'), 8.17 (1H, d, J = 9.7 Hz, H-4)

Mass 스펙트럼은 이온 피크가 m/z 216에서 나타나고 base피크가 m/z 173.1에서 그리고 fragment이온피크가 m/z 201.1, 188.1, 158.2, 145.2, 131.1에 나타났다.Mass spectra showed ion peaks at m / z 216, base peaks at m / z 173.1, and fragment ion peaks at m / z 201.1, 188.1, 158.2, 145.2, and 131.1.

실시예 17: [d]의 추출공정Example 17: Extraction process of [d]

실시예 11의 방법에 의해서 추출물 100g을 기준하여 도면 제 2도와 같이 용액 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하여 이를 무수황산나트륨으로 탈색하고 걸러서 회수된 유기용매를 합하여 감압축하였다. 다시 이를 CHCl3150㎖씩 4회 추출하고 불용성 물질을 pH 2로 맞추고 다시 디클로로메탄 250㎖씩 4회 추출하여 유리된 유기층을 무수 황산마그네슘 1g을 가하여 탈수한 다음 감압농축하여 칼럼크로마토그래피(전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 화합물[d] 0.1g을 얻었다.By the method of Example 11 based on 100g extract was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the fig extract fraction filter, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times, and the layers were separated, decolorized with anhydrous sodium sulfate, filtered, and the recovered organic solvents were combined and concentrated under reduced pressure. Again, 150 ml of CHCl 3 was extracted four times, and the insoluble matter was adjusted to pH 2, and 250 ml of dichloromethane was extracted four times. The free organic layer was dehydrated by adding 1 g of anhydrous magnesium sulfate, and then concentrated under reduced pressure, followed by column chromatography (developing solvent). = Normal butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50: 50), and 0.1 g of compound [d] was obtained.

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.68TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.68

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 3500(OH), 2983(CH), 1650, 1400(C=C)IR Spectrum Data IR (KBr), Cm-1: 3500 (OH), 2983 (CH), 1650, 1400 (C = C)

1H-NMR 스펙트럼 데이타 δ: 1.0(mH,m), 3.3(1H,m,H-3), 5.3(1H,m,H-6) 1 H-NMR spectral data δ: 1.0 (mH, m), 3.3 (1H, m, H-3), 5.3 (1H, m, H-6)

Mass 스펙트럼은 이온 피크가 m/z 414 에서 나타나고 그리고 fragment이온피크가 m/z 303, 254, 213, 159, 146, 107, 95에 나타났다.Mass spectra showed ion peaks at m / z 414 and fragment ion peaks at m / z 303, 254, 213, 159, 146, 107 and 95.

실시예 18: [e, f]의 추출공정Example 18 Extraction of [e, f]

실시예 11의 방법에 의해서 추출물 100g을 기준하여 도면 제 2도와 같이 용액 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 추출 한 다음 층분리하여 이를 무수황산나트륨으로 탈색하고 걸러서 회수된 유기용매를 합하여 감압축하였다. 이를 다시 CHCl3150㎖씩 4회 추출하고 불용성 물질을 pH 2로 맞추고 다시 디클로로메탄 250㎖씩 4회 추출하여 분리하고 불용성 화합물을 칼럼크로마토그래피(전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 화합물[e] 0.04g과 화합물[f] 0.12g을 각각 얻었다.By the method of Example 11 based on 100g extract was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the fig extract fraction filter, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times, and the layers were separated, decolorized with anhydrous sodium sulfate, filtered, and the recovered organic solvents were combined and concentrated under reduced pressure. The mixture was extracted four times with 150 ml each of CHCl 3, and the insoluble substance was adjusted to pH 2, and extracted again with 250 ml of dichloromethane four times. The insoluble compounds were separated by column chromatography (developing solvent = normal butanol: distilled water: chloroform = 10: 5). : 80 and chloroform: methanol = 50:50) to obtain 0.04 g of compound [e] and 0.12 g of compound [f], respectively.

TLC데이타(전개용매: 클로로포름:부탄올:n-헥산 = 85%:10%:5%): Rf=0.13TLC data (developing solvent: chloroform: butanol: n-hexane = 85%: 10%: 5%): Rf = 0.13

IR 스펙트럼 데이타 IR(KBr), Cm-1 : 3300(-OH), 1723(CO), 1690(C=O), 1650, 1450 (aromatic C=C)IR spectral data IR (KBr), Cm-1: 3300 (-OH), 1723 (CO), 1690 (C = O), 1650, 1450 (aromatic C = C)

1H-NMR 스펙트럼 데이타 δ: 6.2(1H,d, J=9.5, H-3), 6.8(1H,s,H-8),6.8(1H,s, H-6),7.7(1H,d, J=8.5, H-5),7.87(1H,d,J=9.7 Hz,H-4), 10.5(1H,s, OH) 1 H-NMR spectral data δ: 6.2 (1H, d, J = 9.5, H-3), 6.8 (1H, s, H-8), 6.8 (1H, s, H-6), 7.7 (1H, d , J = 8.5, H-5), 7.87 (1H, d, J = 9.7 Hz, H-4), 10.5 (1H, s, OH)

실시예 19: [g]의 추출공정Example 19: Extraction process of [g]

무화과 잎을 깨끗이 세척한 후 물을 제거하고 무화과 습체잎 10㎏을 기준하여 무화과잎을 메탄올로 1.5-10배 분량의 용매를 가하여 실시예 12의 방법을 이용하여 추출하여 메탄올을 제거한 후 추출액 100g을 기준하여 도면 제2도와 같이 용액 분획하였다. 즉, 무화과 추출물 분획여두에서 증류수 200㎖를 넣고, 에칠아세테이트 150㎖씩 5회 추출한 다음 층분리하고 수층을 포화 NaCl용액을 넣고 수층의 pH를 2.0에 맞춘다. 다시 에칠아세테이트 150㎖씩 5회 5시간동안 추출 한 다음 불용화합물 및 수층은 포화 염화나트륨, 또는 포화염화칼슘 용액을 이용 실온에서 수포화부탄올 300㎖X5로 추출한 다음 층 분리하여 이를 황산마그네슘 1.0g을 넣고 40℃에서 10분간 잘 저어준 다음 이를 걸러서 유기용매를 감압농축하여 최종적으로 액상시럽형태의 5.6g을 얻었다. 이를 다시 칼럼크로마토그래피(전개용매=노르말부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50)을 실시하여 화합물 [g]을 얻었다.After washing the fig leaves, the water is removed and the fig leaves are extracted with methanol by adding 1.5-10 times the amount of solvent, based on 10 kg of fig wet leaves, to remove methanol using the method of Example 12, and then 100 g of the extract is extracted. The solution was fractionated as shown in FIG. That is, 200 ml of distilled water was added from the fig extract fraction filter, 150 ml of ethyl acetate was extracted five times, and the layers were separated. The aqueous layer was added with saturated NaCl solution and the pH of the aqueous layer was adjusted to 2.0. Then, 150 ml of ethyl acetate was extracted five times for 5 hours. The insoluble compounds and the aqueous layer were extracted with saturated sodium chloride or saturated calcium chloride solution at 300 mlX5 of saturated butanol at room temperature, and the layers were separated. Then, 1.0 g of magnesium sulfate was added and 40 Stir well at 10 ° C. for 10 min, filter it, and concentrate the organic solvent under reduced pressure to obtain 5.6 g of liquid syrup. This was further subjected to column chromatography (developing solvent = normal butanol: distilled water: chloroform = 10: 5:80 and chloroform: methanol = 50: 50) to obtain a compound [g].

제조실시예 1Preparation Example 1

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(A) 3.0Fig isolate component (A) 3.0 with antifungal and antibacterial properties

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

비누베이스 96.25Soap Base 96.25

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 잘 혼합한 후 비누 제조 기계에서 압출하고 일정한 크기로 절단, 형타하여 고체형태인 화장비누 조성물을 제조하였다.The components were mixed well in a mixer and then extruded in a soap making machine, cut into a predetermined size, and molded to prepare a cosmetic soap composition in solid form.

제조실시예 2Preparation Example 2

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 A 13.0Fig. Isolate A 13.0 with antifungal and antibacterial properties

호호바유 0.3Jojoba Oil 0.3

비누베이스 84.3Soap Base 84.3

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 잘 혼합한 후 비누 제조 기계에서 압출하고 일정한 크기로 절단, 형타하여 고체형태인 화장비누 조성물을 제조하였다.The components were mixed well in a mixer and then extruded in a soap making machine, cut into a predetermined size, and molded to prepare a cosmetic soap composition in solid form.

제조실시예 3Preparation Example 3

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 A 24.0Fig. Isolate A 24.0 with antifungal and antibacterial properties

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

비누 베이스 72.3Soap Base 72.3

토코페롤 아세테이트 0.2Tocopherol Acetate 0.2

상기 성분들을 혼합기에서 잘 혼합한 후 비누 제조 기계에서 압출하고 인정한 크기로 절단, 형타하여 고체형태인 화장비누 조성물을 제조하였다.The components were mixed well in a mixer, extruded in a soap making machine, cut and shaped into a recognized size to prepare a cosmetic soap composition in solid form.

제조실시예 4Preparation Example 4

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 G 12.0Fig isolate ingredient with antifungal and antibacterial ingredients G 12.0

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

비누 베이스 86.3Soap Base 86.3

부틸레이티드하이드록시톨루엔 0.05Butylated hydroxytoluene 0.05

글리세린 0.2Glycerin 0.2

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형태인 화장비누 조성물을 제조하였다.The components were mixed in a mixer to prepare a cosmetic soap composition in the same manner as in Example 1.

제조실시예 5Preparation Example 5

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분a 10.0Fig isolate with antifungal and antimicrobial ingredientsa 10.0

부틸레이티드하이드록시톨루엔(B. H. T) 0.05Butylated hydroxytoluene (B. H. T) 0.05

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

비누베이스 94.5Soap Base 94.5

토코페롤 아세테이트 2.0Tocopherol Acetate 2.0

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형태인 화장비누 조성물을 제조하였다.The components were mixed in a mixer to prepare a cosmetic soap composition in the same manner as in Example 1.

제조실시예 6Preparation Example 6

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 a 3.0Fig isolate containing antifungal and antibacterial ingredients a 3.0

폴리페놀 0.3Polyphenol 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

비누베이스 95.6Soap Base 95.6

토코페롤 아세테이트 0.7Tocopherol Acetate 0.7

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형태인 화장비누 조성물을 제조하였다.The components were mixed in a mixer to prepare a cosmetic soap composition in the same manner as in Example 1.

제조실시예 7Preparation Example 7

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 A 20Fig. Isolate A 20 with antifungal and antibacterial properties

비누베이스 5.0Soap Base 5.0

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

글루타치온 1.0Glutathione 1.0

부틸레이티드하이드록시톨루엔 0.05Butylated hydroxytoluene 0.05

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

D.B.A(알킬벤젠 설폰산) 0.4D.B.A (alkylbenzene sulfonic acid) 0.4

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체형태인 샴푸 조성물을 제조하였다.The components were mixed in a mixer to prepare a shampoo composition in liquid form in the same manner as in Example 1.

제조실시예 8Preparation Example 8

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분 A 15.0Fig. Isolate A 15.0 with antifungal and antibacterial properties

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

D.B.A(알킬벤젠 설폰산) 0.4D.B.A (alkylbenzene sulfonic acid) 0.4

비누베이스 10Soap Base 10

올레인산 0.1Oleic Acid 0.1

세탄올 5Cetanol 5

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체 형태의 물비누 조성물을 제조하였다.The components were mixed in a mixer and the water soap composition in liquid form was prepared in the same manner as in Example 1.

제조실시예 9Preparation Example 9

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(G,A) 5.0Fig. Isolates with antifungal and antibacterial ingredients (G, A) 5.0

트리암시놀론 아세트나이트 0.1Triamcinolone Acetite 0.1

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

비누 베이스 91.3Soap Base 91.3

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형태인 화장비누 조성물을 제조하였다.The components were mixed in a mixer to prepare a cosmetic soap composition in the same manner as in Example 1.

제조실시예 10Preparation Example 10

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(A) 20Fig separation component with antifungal and antibacterial ingredients (A) 20

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체 세정제를 제조하였다.The above ingredients were mixed in a mixer to prepare a liquid detergent in the same manner as in Example 1.

제조실시예 11Preparation Example 11

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과잎 분리 성분 G 5.0Fig leaf separation ingredient with antifungal and antibacterial ingredient G 5.0

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체형상인 린스 조성물을 제조하였다.The above ingredients were mixed in a mixer to prepare a liquid rinse composition in the same manner as in Example 1.

제조실시예 12Preparation Example 12

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과잎 분리 성분 G,A 10.0Fig leaf separation ingredient with antifungal and antibacterial properties G, A 10.0

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체샴푸 조성물을 제조하였다.The above ingredients were mixed in a mixer to prepare a liquid shampoo composition in the same manner as in Example 1.

제조실시예 13Preparation Example 13

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과잎 분리 성분 G 4.0Fig leaf separation ingredient G 4.0 with antifungal and antibacterial properties

비누 베이스 10Soap Base 10

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체형상인 샴푸 조성물을 제조하였다.The above ingredients were mixed in a mixer to prepare a liquid shampoo composition in the same manner as in Example 1.

제조실시예 14Preparation Example 14

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 잎,열매 분리 혼합 성분 G 5.0Fig leaf with antifungal and antibacterial ingredients

비누 베이스 96.4Soap Base 96.4

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체비누 조성물인 화장비누를 제조하였다.The above ingredients were mixed in a mixer to prepare a cosmetic soap as a solid soap composition in the same manner as in Example 1.

제조실시예 15Preparation Example 15

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 잎,열매 분리 혼합 성분(G,A) 20.0Fig leaf with antifungal and antibacterial ingredients, fruit separation mixed ingredient (G, A) 20.0

비누 베이스 78.4Soap Base 78.4

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.6Polyethylene Glycol 4000 0.6

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형상 조성물인 화장비누 제제를 제조하였다.The above ingredients were mixed in a mixer to prepare a cosmetic soap formulation in the same manner as in Example 1.

제조실시예 16Preparation Example 16

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 잎,열매 분리 혼합 성분(G) 23.0Fig leaf with antifungal and antibacterial ingredients, separate component of fruit (G) 23.0

비누 베이스 78Soap Base 78

호호바유 0.3Jojoba Oil 0.3

세탄올 0.15Cetanol0.15

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 고체형상 조성물인 화장비누 제제를 제조하였다.The above ingredients were mixed in a mixer to prepare a cosmetic soap formulation in the same manner as in Example 1.

제조실시예 17(비교예)Preparation Example 17 (Comparative Example)

(중량부)(Parts by weight)

호호바유 0.3Jojoba Oil 0.3

비누 베이스 96.2Soap Base 96.2

글리세린 0.2Glycerin 0.2

폴리에틸렌글리콜 4000 0.8Polyethylene Glycol 4000 0.8

세탄올 0.15Cetanol0.15

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 비누 조성물을 제조하였다.The above ingredients were mixed in a mixer to prepare a soap composition in the same manner as in Example 1.

제조실시예 18Preparation Example 18

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(G) 23Fig. Isolate component (G) with antifungal and antibacterial properties 23

비누 베이스 10.0Soap Base 10.0

올레인산 0.1Oleic Acid 0.1

세탄올 0.15Cetanol0.15

글루타치온 1.0Glutathione 1.0

부틸레이티드하이드록시톨루엔 0.05Butylated hydroxytoluene 0.05

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

D.B.A(알킬벤젠 설폰산) 0.4D.B.A (alkylbenzene sulfonic acid) 0.4

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체형태인 샴푸 조성물을 제조하였다.The components were mixed in a mixer to prepare a shampoo composition in liquid form in the same manner as in Example 1.

제조실시예 19Preparation Example 19

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(G) 20Fig isolate ingredient with antifungal and antibacterial ingredients (G) 20

올레인산 0.1Oleic Acid 0.1

세탄올 0.15Cetanol0.15

글루타치온 1.0Glutathione 1.0

부틸레이티드하이드록시톨루엔 0.05Butylated hydroxytoluene 0.05

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 액체형태인 세정제 조성물을 제조하였다.The above ingredients were mixed in a mixer to prepare a cleaning composition in liquid form in the same manner as in Example 1.

제조실시예 20Preparation Example 20

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(A) 25Fig. Isolate component (A) with antifungal and antibacterial properties 25

글루타치온 1.0Glutathione 1.0

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 크림제 형태인 연고제 조성물을 제조하였다.The ingredients were mixed in a mixer and an ointment composition in the form of a cream was prepared in the same manner as in Example 1.

제조실시예 21Preparation Example 21

(중량부)(Parts by weight)

항진균 및 항균성분이 있는 무화과 분리 성분(G) 10Fig isolate ingredient with antifungal and antibacterial ingredients (G) 10

글루타치온 1.0Glutathione 1.0

토코페롤 아세테이트 0.3Tocopherol Acetate 0.3

글리세린 0.2Glycerin 0.2

상기 성분들을 혼합기에서 혼합하고 실시예 1과 동일한 방법으로 크림제 형태인 연고제 조성물을 제조하였다.The ingredients were mixed in a mixer and an ointment composition in the form of a cream was prepared in the same manner as in Example 1.

상기 실시예 및 비교예에서 제조한 비누 조성물의 진균 및 항균치료 효과를 확인하기 위하여 항균력 시험, 비듬 치료 효과 확인 임상실험을 하였다.In order to confirm the fungal and antimicrobial therapeutic effects of the soap compositions prepared in Examples and Comparative Examples, an antimicrobial activity test and a clinical test to confirm the dandruff therapeutic effect were conducted.

실험예 1: 무화과 생과 및 무화과 잎의 추출물 및 각 분획화합물에 대한 최소발육저지농도(MIC in vitro)의 측정Experimental Example 1: Determination of minimum fresh jersey concentration (MIC in vitro) for extracts of figs and fig leaves

1) 사용균주1) Use strain

본 실험에 사용한 미생물은 G(-)균으로 에세리시아 콜라이(Escherichia coli) ATCC 10536, 슈도모나스 아이루기노사(Pseudomonas aeruginosa) ATCC 9027, G(+)균으로 Staphylococcus aureus ATCC 25923, 바실루스 서브틸리스(Bacillus subtilis) ATCC 6633, 진균으로 칸디다 유틸리스(Candida utilis), 칸디다 알비칸스(Candida albicans) ATCC 10231, 사카로미세스 세레비시애(Saccharomyces cerevisiae) ATCC 9763, 아스퍼길루스 나이거(Aspergillus niger) 9029, 칸디다 슈도트로피칼리스(Candida pseudotropicalis), 토루롭시스 글라브라타(Tourlopsis glabrata) 89-5 를 사용하였다.The microorganisms used in this experiment were G (-) bacteria, Escherichia coli ATCC 10536, Pseudomonas aeruginosa ATCC 9027, and G (+) bacteria Staphylococcus aureus ATCC 25923, Bacillus subtilis subtilis) ATCC 6633, Candida utilis, Candida albicans ATCC 10231, Saccharomyces cerevisiae ATCC 9763, Aspergillus niger 9029, Candida Candida pseudotropicalis, Tourlopsis glabrata 89-5 were used.

2) 사용배지2) Medium used

본 실험에 사용한 세균용 배지: Mueller Hinton broth, Mueller Hinton agar이며 진균용 배지: Sabouraud Dextrose Broth, Sabouraud Dextrose agar로 조정하여 사용하였다.Bacterial media used in this experiment: Mueller Hinton broth, Mueller Hinton agar and fungal media: Sabouraud Dextrose Broth, Sabouraud Dextrose agar.

3) 각 분획추출물질 및 분리물질 조제와 검정 배지 제조 및 항미생물 활성 측정:3) Preparation of each fraction extract and separation substance, preparation of assay medium and measurement of antimicrobial activity:

① 균희석액을 만들기 위해 전배양은 균의 농도가 104-106 CFU/ml가 되게 희석한다.① In order to make fungal diluent, pre-culture should be diluted to concentration of 104-106 CFU / ml.

② 각 검체를 알맞은 용매로 녹인 후 배지로 2배 희석법으로 희석한다.② Dissolve each sample in a suitable solvent and dilute with 2 times dilution with medium.

③ 각각의 시험관에 균액을 접종한다.③ Inoculate the bacteria solution in each test tube.

④ 세균은 37도 24시간 배양하며 진균은 36-48시간 배양한다.④ bacteria 37 degrees 24 hours incubation fungi 36-48 hours.

⑤ 각 배양이 끝난후 시험관을 흔들어 균의 탁도를 확인한다. 탁도 여부를 확인한후 각각을 Mueller Hinton ager, Sabouraud Dextrose agar 배지에 제 접종하여 확인한다.⑤ Shake the test tube after each incubation to check the turbidity of the bacteria. After checking the turbidity, each was inoculated in Mueller Hinton ager and Sabouraud Dextrose agar medium.

⑥ 균의 성장여부를 확인한 후 성장이 인정되지 않는 가장 낮은 농도의 시험관 농도를 정하여 상기와 같은 액체배지 희석법(Broth Serial Dilution Method)으로 MIC를 정한다.⑥ After confirming the growth of bacteria, determine the lowest test tube concentration at which growth is not recognized.

분리된 화합물 (A,B,C,D,E,F,G 및 a,b,c,d,e,f) 과 대조 화합물 (케토코나졸)에 대한 in vitro에서 최소발육 저지농도(MIC, mg/ml)를 측정한 결과는 하기 표 1에 나타내었다.Minimum developmental inhibition concentrations (MIC, mg / in vitro for isolated compounds (A, B, C, D, E, F, G and a, b, c, d, e, f)) The results of measuring ml) are shown in Table 1 below.

표 1.Table 1.

단위: ㎎/㎖Unit: mg / ml 균주Strain GG BB CC DD EE FF AA aa bb cc dd ee K* K * 그람 양성 박테리아Gram-positive bacteria 바실루스서브틸리스(Bacillus subtilis) ATCC 6633Bacillus subtilis ATCC 6633 >5.42> 5.42 99 55 3636 88 -- 3131 2121 99 11.111.1 3737 1515 1.51.5 스테피로코커스 아우레우스(Staphylococcus aureus) ATCC 25923Staphylococcus aureus ATCC 25923 2.792.79 9.69.6 1111 18.518.5 -- -- 11.511.5 11.311.3 99 5.565.56 18.518.5 1515 7.57.5 그람 음성 박테리아Gram negative bacteria 에세리시아 콜라이(Escherichia coli) ATCC 10536Escherichia coli ATCC 10536 >2.79> 2.79 4.54.5 1313 1313 55 1010 1313 11.311.3 44 5.565.56 18.518.5 1515 1.871.87 슈도모나스 아에루기노사(Seudomonas aeruginosa) ATCC 9027Pseudomonas aeruginosa ATCC 9027 1.351.35 12.312.3 1111 1818 -- -- 2020 2020 1212 2.282.28 18.518.5 1515 1.871.87 칸디다 유틸리스(Candida utilis)Candida utilis 0.6750.675 55 3.33.3 4.64.6 24.624.6 >282> 282 55 2.282.28 4.624.62 7.57.5 1.871.87 칸디다 알비칸스(Candida albicans) ATCC 10231Candida albicans ATCC 10231 >0.675> 0.675 44 2.792.79 2.72.7 2.72.7 1010 12.712.7 282282 44 >2.28> 2.28 >4.6> 4.6 7.57.5 1.871.87 사카로미세스 세레비시아(Saccharomyces cerevisiae) ATCC 9763Saccharomyces cerevisiae ATCC 9763 2.792.79 44 77 18.518.5 -- -- 11.511.5 11.311.3 44 5.565.56 18.518.5 >15> 15 1.8751.875 아스퍼길루스 나이거(Aspergillus niger) 9029Aspergillus niger 9029 2.792.79 11.111.1 1111 3737 55 -- 13.713.7 122.6122.6 1010 11.111.1 3737 1515 1.8751.875

주) K*는 케토코나졸을 나타낸다.Note) K * represents ketoconazole.

본 발명의 약용비누조성물과 대조비누 또는 케토코나졸의 항균력을 측정한 결과는 하기표 2에 나타내었다.The results of measuring the antibacterial activity of the medicinal soap composition of the present invention and the control soap or ketoconazole are shown in Table 2 below.

표 2. 미생물의 최소성장억제농도 (minimum inhibition concentration)Table 2. Minimum Inhibition Concentration of Microorganisms

(단위: ㎍/㎖)(Unit: μg / ml) 균 주Strain 제조실시예 7 (샴푸)Preparation Example 7 (shampoo) 제조실시예 11 (린스)Preparation Example 11 (rinse) 제조실시예14(화장비누)Preparation Example 14 제조실시예17(대조비누)Preparation Example 17 (Control Soap) 케토코나졸 원료Ketoconazole Raw Material G(-)균으로에세리시아 콜라이(Escherichia coli) ATCC 10536,Escherichia coli ATCC 10536, 2929 5959 1212 5656 27.927.9 슈도모나스 아에루기노사(Pseudomonas aeruginosa) ATCC 9027Pseudomonas aeruginosa ATCC 9027 1515 2525 1010 2828 13.513.5 G(+)균으로스테피로코커스 아우레우스 (Staphylococcus aureus)ATCC 25923Staphylococcus aureus as G (+) 3535 3737 1515 6060 27.927.9 바실루스 서브틸리스(Bacillus subtilis) ATCC 6633,진균으로Bacillus subtilis ATCC 6633, fungus 8484 8989 2020 108108 54.254.2 칸디다 유틸리스(Candida utilis)Candida utilis 6.06.0 5.05.0 1.51.5 1414 6.756.75 칸디다 알비칸스(Candida albicans) ATCC 10231Candida albicans ATCC 10231 3.53.5 4.54.5 2.02.0 1414 6.756.75 사카로미세스 세레비시아(Saccharomyces cerevisiae) ATCC 9763Saccharomyces cerevisiae ATCC 9763 3030 3636 77 5656 27.927.9 아스퍼길루스 나이거(Aspergillus niger) 9029Aspergillus niger 9029 7070 8787 1010 160160 8080 칸디다 슈도트로피칼리스(Candida pseudotropicalis)Candida pseudotropicalis 100100 9595 4040 160160 160160 토루롭시스 글라브라타(Tourlopsis glabrata) 89-5Tourlopsis glabrata 89-5 7474 7474 1010 160160 160160

주1) 대조비누의 농도는 실시예 7 샴푸, 실시예 11 연고제, 실시예 14 비누의 각 희석단계별로 항진균 및 항균성분이 있는 무화과 분리 성분 농도에 준함.Note 1) The concentration of the control soap is based on the concentration of the fig separation component having antifungal and antibacterial ingredients at each dilution step of Example 7 shampoo, Example 11 ointment, and Example 14 soap.

주2) 항진균 및 항균성분이 있는 무화과 분리 성분 원료의 용해는 물로 함.Note 2) The dissolution of the raw material of fig isolate with antifungal and antibacterial ingredients is water.

실험예 2: 비듬치료 효과 및 피부의 가려움 및 무좀 및 습진등 피부질화 확인 임상 실험Experimental Example 2: Confirmation of dandruff treatment effect and skin itching and skin nitriding such as athlete's foot and eczema

비듬치료 및 피부의 가려움 및 무좀 및 습진등 피부질환 치료에 관한 임상효과를 측정하기 위하여 비듬 및 피부의 가려움 및 무좀 및 습진등 피부염이 많은 20∼40대 실험자 20명(실험군 10명, 대조군 10명)을 피시험자로 선정한 뒤 본발명의 제조 실시예 1(실험군)와 대조비누(제조실시예 7)의 비누조성물로 1일 1회 2주간 두피에 사용하도록하여 비듬 및 피부의 가려움 및 무좀 침 습진등 피부질환 치료 효과를 파악하였다.In order to measure the clinical effects of dandruff treatment and skin diseases such as itching and athlete's foot and eczema, 20 subjects in their 20s and 40s with high dermatitis such as dandruff and itching and athlete's foot and eczema (10 in experimental group and 10 in control group) ) Was selected as a test subject, and the soap composition of Preparation Example 1 (Experimental Group) and Control Soap (Preparation Example 7) of the present invention was used for scalp once a day for 2 weeks for dandruff and itching and athlete's foot eczema. The effects of back skin diseases were evaluated.

판정 방법은 일정한 등급을 매긴후, 육안 관찰에 의해 비듬 감소 및 두피의 가려움증 감소와 피부의 가려움 및 무좀, 습진 등 피부염의 해소를 확인하였다.After determining the grade, the visual observation confirmed the reduction of dandruff, itching of the scalp, the itching of the skin, and the elimination of dermatitis such as athlete's foot and eczema.

판정기준은 하기 표 3에 나타내었다.Criteria are shown in Table 3 below.

표 3.Table 3.

등급Rating 상 태condition 0 1 2 3 40 1 2 3 4 두피의 가려움 및 비듬이 완전히 없어지지 않음 두피의 가려움 및 비듬이 약간 없어짐 두피의 가려움 및 비듬이 상당히 없어짐 두피의 가려움 및 비듬이 거의 없어짐 두피의 가려움 및 비듬이 완전히 없어짐The scalp does not completely itch and dandruff Slightly disappears the scalp itch and dandruff Significantly eliminates the itching and dandruff of the scalp The scalp virtually eliminates the itching and dandruff The scalp completely disappears

임상 실험 대상지의 비듬치료에 대한 등급이 3 내지 4의 감소율을 나타내면 효과 우수, 1내지 2의 감소율을 나타내면 효과 중간, 감소율이 나타나지 않으면 효과 없음으로 판정한다. 상기 실험 결과는 다음 표 4에 나타난 바와 같다.If the grade for the dandruff treatment of the clinical trial site shows a reduction rate of 3 to 4, the effect is excellent. The experimental results are shown in Table 4 below.

표 4. 비듬 치료효과 확인 임상실험 결과Table 4. Clinical trial results confirming dandruff treatment effect

치료효과 우수Excellent therapeutic effect 치료효과 중간Treatment effect 치료 효과 없음No therapeutic effect system 제조실시예 1제조실시예 11제조실시예 13제조실시예 17(비교예)Manufacture Example 1 Manufacture Example 11 Manufacture Example 13 Manufacture Example 17 (Comparative Example) 8(90%)9(90%)7(90%)08 (90%) 9 (90%) 7 (90%) 4(10%)1(10%)3(10%)1(10%)4 (10%) 1 (10%) 3 (10%) 1 (10%) 000 9(90%)000 9 (90%) 10명(100%)10명(100%)10명(100%) 10명(100%)Ten (100%) Ten (100%) Ten (100%) Ten (100%)

상기 표에 보는 바와 같이, 항진균 및 항균성분이 있는 무화과 분리 성분[A]을 함유한 비누가 이를 함유하지 않은 비누보다 비듬치료 효과가 매우 우수한 것으로 나타났다.As shown in the table, the soap containing the anti-fungal and antibacterial fig separation component [A] was found to have a much better dandruff treatment effect than the soap does not contain it.

실험예 3: 피부의 가려움증과 무좀 및 습진등 피부염 임상실험Experimental Example 3: Clinical trial of skin itching and dermatitis such as athlete's foot and eczema

표 5. 판정기준Table 5. Criteria

등 급Rating 상 태condition 12341234 피부의 가려움 및 무좀 및 습진등 피부염이 완전히 없어지지 않음피부의 가려움 및 무좀 및 습진등 피부염 약간 없어짐피부의 가려움 및 무좀 및 습진등 피부염 상당히 없어짐피부의 가려움 및 무좀 및 습진등 피부염 거의 없어짐피부의 가려움 및 무좀 및 습진등 피부염 등이 완전히 없어짐Itching of the skin and dermatitis such as athlete's foot and eczema are not completely disappeared.Itching of the skin and dermatitis such as athlete's foot and eczema. Dermatitis such as athlete's foot and eczema disappear completely

임상 실험 대상지의 피부의 가려움 및 무좀 및 습진, 비듬치료에 대한 등급이 3 내지 4의 감소율을 나타내면 효과 우수, 1 내지 2의 감소율을 나타내면 효과 중간, 감소율이 나타나지 않으면 효과 없음으로 판정한다. 상기 실험 결과는 다음 표에 나타난 바와 같다.It is determined that the grade of skin itch, athlete's foot, eczema, and dandruff treatment of clinical trial site shows excellent effect when the reduction rate is 3 to 4, and the effect is medium when the reduction rate is 1 to 2, and no effect when the reduction rate is not shown. The experimental results are shown in the following table.

표 6.Table 6.

치료효과 우수Excellent therapeutic effect 치료효과 중간Treatment effect 치료효과 없음No treatment effect system (실시예 1)(Example 1) 8(90%)8 (90%) 2(10%)2 (10%) 00 10명(100%)10 people (100%) (비교예 1)(Comparative Example 1) 00 1(10%)1 (10%) 9(90%)9 (90%) 10명(100%)10 people (100%)

상기 표에 보는 바와 같이, 항진균 및 항균성분이 있는 무화과 분리성분을 함유한 연고제가 이를 함유하지 않은 대조 연고제보다 피부의 가려움 및 무좀 및 습진등 피부 치료효과가 매우 우수한 것으로 나타났다.As shown in the table, the ointment containing the anti-fungal and antimicrobial component of the fig separation component was found to have a much better skin healing effect such as itching and athlete's foot and eczema than the control ointment containing no.

본 발명에 따른 약용비누조성물은 독성이나 부작용없이 피부무좀 및 진균 그리고 향균 등의 치료효과가 우수하다.The medicinal soap-free composition according to the present invention has excellent therapeutic effects such as skin athlete's foot and fungus and antibacterial without toxicity or side effects.

Claims (10)

알칼리금속비누베이스에 승정 도우핀(Masui Dauphine), 봉래시 또는 화이트제노아종의 무화과 열매 또는 잎의 용매 추출분리물 0.05 내지 25 중량% 및 안정화제 0.1 내지 5.0 중량%를 함유함을 특징으로 하는 약용비누조성물.Medicinal soap, characterized in that the alkali metal soap base contains 0.05 to 25% by weight of solvent extract isolates of fig fruit or leaves of Masui Dauphine, Bongsi or White Genoa Composition. 제 1항에 있어서, 무화과열매의 추출분리물이 도면 제 1도에 도시된 바와 같이 추출 및 분리된 분획물 [A], [B], [C], [D], [E], [F] 또는 [G]임을 특징으로 하는 약용비누조성물.The method of claim 1, wherein the extract of the fig fruit is extracted and separated fractions [A], [B], [C], [D], [E], [F] as shown in FIG. Or [G] medicinal soap composition. 제 1항에 있어서, 무화과잎의 추출분리물이 도면 제 2도에 도시된 바와 같이 추출 및 분리된 분획물 [a], [b], [c], [d], [e], [f] 또는 [g]임을 특징으로 하는 약용비누조성물.The extract of claim 1, wherein the extract isolate of the fig leaf is extracted and separated fractions [a], [b], [c], [d], [e], [f] as shown in FIG. Or [g]. A medicinal soap composition. 제 1항에 있어서, 용매추출분리물이 무화과열매 또는 잎을 메탄올용매를 이용하여 침적법, 압착법 또는 분쇄법으로 추출하여 혼합 추출물을 얻고, 이를 유기용매인 에틸아세테이트, n-부탄올, 에틸에테르, 핵산, 클로로포름, 메칠렌클로라이드 또는 물로 각각 추출하여 분획 추출물을 얻고, 또한 이를 연속방법으로 수포화 부탄올로 pH 2-6.5인 산성용매 또는 pH 7.5-10인 알칼리 용매에서 온도 30-90℃에서 2 내지 36시간 동안 용매의 종류에 따라 분획 추출한 것인 약용비누조성물.The method of claim 1, wherein the solvent extract separation extract of the fig fruit or leaf by dipping, pressing or grinding method using a methanol solvent to obtain a mixed extract, which is an organic solvent ethyl acetate, n-butanol, ethyl ether , Extract with nucleic acid, chloroform, methylene chloride or water, respectively, to obtain a fraction extract, and also in a continuous method in an acidic solvent of pH 2-6.5 with saturated butanol or an alkaline solvent of pH 7.5-10 at a temperature of 30-90 ℃ The medicinal soap-free composition which is fractionated according to the type of solvent for 36 hours. 제 1항에 있어서, 무화과열매의 추출분리물이 카본처리로 탈색을 하고 용액을 알카리 및 산으로 중화시키고 이를 유기용매인 에틸아세테이트, n-부탄올, 에틸에테르, 핵산, 클로로포름, 메칠렌클로라이드 또는 물을 통하여 분리하여 분획 활성물질을 얻고, 이를 칼럼 크로마토그래피-고형 충진제로서 실리카겔(SiO2), 산화알루미나(Al2O3) 그리고 전개용매(클로로포름:부탄올=70:30, 메탄올, 아세토나이트릴, 에틸아세테이트:클로로포름:=70:30, n-부탄올:클로로포름:핵산=30:60:10, 클로로포름:메탄올=70:30, n-부탄올:증류수:클로로포름=10:5:80 및 클로로포름:메탄올=50:50, 클로로포름:메탄올=90:10, 클로로포름:메탄올:암모니아수=40:40:5)를 이용하여 추출분리된 약용비누조성물.The method of claim 1, wherein the extract separation of the fig fruit is decolorized by carbonization and the solution is neutralized with alkali and acid, which is an organic solvent, ethyl acetate, n-butanol, ethyl ether, nucleic acid, chloroform, methylene chloride or water. Separation was carried out to obtain a fractional active material, which was purified by silica gel (SiO 2 ), alumina oxide (Al 2 O 3 ) and developing solvent (chloroform: butanol = 70: 30, methanol, acetonitrile, Ethyl acetate: chloroform: = 70: 30, n-butanol: chloroform: nucleic acid = 30: 60: 10, chloroform: methanol = 70: 30, n-butanol: distilled water: chloroform = 10: 5: 80 and chloroform: methanol = 50:50, chloroform: methanol = 90: 10, chloroform: methanol: ammonia water = 40: 40: 5). 제 1항에 있어서, 무화과열매 또는 잎의 추출분리물이 무화과 열매로 완숙과일, 미숙과일 그리고 잎을 직접 n-부탄올 또는 메탄올에 침적시키고 추출하여 온도 20-70℃에서 감압농축하고 이를 직접 칼럼 크로마토그래피로 혼합물질 또는 단일성분 화합물로 분리시킨 것인 약용비누조성물.The extract of fig fruit or leaf is extracted with fig fruit by dipping the ripe fruit, immature fruit and leaf directly into n-butanol or methanol, extracting and concentrating under reduced pressure at a temperature of 20-70 ° C., and direct column chromatography A medicinal soapless composition which is separated into a mixture or a monocomponent compound by chromatography. 제 1항에 있어서, 안정화제가 비타민 C, 토코페롤, 글루타치온, 폴리페놀, 부틸화하이드록시아니솔, 부틸화하이드록시톨루엔, 아스코르빌팔미테이트, 아스코르빌올레에이트, 아스코르빈산나트륨, 무수나트륨비설파이트, 무수나트륨설파이트, 구연산, 구연산나트륨, 능금산, 탄산나트륨, 중조, 치오황산나트륨, 중아황산나트륨, 치오우레아, 이미드우레아, 폴리소르베이트80, 폴리옥시메틸렌노닐페닐에테르, 올레인산 및 D, B, A(알킬벤젠설폰산)중에서 선택된 1종 또는 2종 이상임을 특징으로 하는 약용비누조성물.2. The stabilizer according to claim 1, wherein the stabilizer is vitamin C, tocopherol, glutathione, polyphenol, butylated hydroxyanisole, butylated hydroxytoluene, ascorbyl palmitate, ascorbyl oleate, sodium ascorbate, anhydrous sodium Bisulfite, anhydrous sodium sulfite, citric acid, sodium citrate, nitric acid, sodium carbonate, sodium bicarbonate, sodium thiosulfate, sodium bisulfite, thiourea, imideurea, polysorbate 80, polyoxymethylenenonylphenyl ether, oleic acid and D, B, A medicinal soap-free composition characterized in that one or two or more selected from A (alkylbenzenesulfonic acid). 제 1항에 있어서, 알칼리금속베이스가 탄소원자수 10 내지 20개인 지방산의 알칼리금속염으로서 수분을 7.0 내지 28 중량% 함유함을 특징으로 하는 약용비누조성물.The medicinal soap composition according to claim 1, wherein the alkali metal base contains 7.0 to 28% by weight of water as an alkali metal salt of a fatty acid having 10 to 20 carbon atoms. 제 20항에 있어서, 지방산이 야자유, 팜유, 대두유, 피마자유, 올리브유, 팜핵유, 우지, 양지, 돈지 또는 어유로부터 얻어지고 또한 알칼리금속은 나트륨 또는 칼륨으로 단독 또는 혼합하여 지반산을 중화시킨 약용비누조성물.The medicinal product according to claim 20, wherein the fatty acid is obtained from palm oil, palm oil, soybean oil, castor oil, olive oil, palm kernel oil, tallow, sunny, lard, or fish oil, and the alkali metal is neutralized by solely or mixing with sodium or potassium. Soap composition. 제 1항, 2항 및 3항중 어느 하나에 있어서, 조성물이 샴푸, 액체비누, 린스, 항미생물제, 어류병치료제, 어류사료첨가제, 식료품가공첨가제, 무공해식물재배시 농약대체물, 무좀치료제, 피부연고제 또는 피부질환치료제임을 특징으로 하는 약용비누조성물.The composition according to any one of claims 1, 2 and 3, wherein the composition is a shampoo, a liquid soap, a rinse, an antimicrobial agent, a fish disease treatment agent, a fish feed additive, a food processing additive, a pesticide substitute, an athlete's foot treatment agent, a skin ointment when planting a pollution-free plant. Or medicinal soap composition characterized in that the treatment for skin diseases.
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KR100777258B1 (en) * 2006-12-21 2007-11-28 고려바이오주식회사 Acaricides and manufacturing methods using plant extracts
KR101050472B1 (en) * 2009-11-30 2011-07-20 임광세 Multifunctional beauty soap and its manufacturing method
JP2013539748A (en) * 2010-09-10 2013-10-28 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップ Bioactive composition comprising fig serous fraction and method for reducing the hyperpigmented appearance of skin
KR101468819B1 (en) * 2013-09-23 2014-12-04 순천대학교 산학협력단 Antibacterial compositions containing Ficus carica L extracts or fractions thereof under light intensity
US10682384B2 (en) 2017-02-28 2020-06-16 Cosmax Ns, Inc. Composition comprising natural complex extract as active ingredient

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