CN101058596A - Method of extracting and preparing triterpene compounds - Google Patents
Method of extracting and preparing triterpene compounds Download PDFInfo
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- CN101058596A CN101058596A CN 200610025792 CN200610025792A CN101058596A CN 101058596 A CN101058596 A CN 101058596A CN 200610025792 CN200610025792 CN 200610025792 CN 200610025792 A CN200610025792 A CN 200610025792A CN 101058596 A CN101058596 A CN 101058596A
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- Prior art keywords
- cra
- colosolic
- extraction
- preparation
- resin
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- 238000000034 method Methods 0.000 title claims abstract description 11
- -1 triterpene compounds Chemical class 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 19
- 239000011347 resin Substances 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- HFGSQOYIOKBQOW-ZSDYHTTISA-N corosolic acid Chemical compound C1[C@@H](O)[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C HFGSQOYIOKBQOW-ZSDYHTTISA-N 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 11
- 239000000284 extract Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 238000000605 extraction Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 239000003463 adsorbent Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000003648 triterpenes Chemical class 0.000 claims description 6
- 238000011010 flushing procedure Methods 0.000 claims description 4
- 238000005374 membrane filtration Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 239000002994 raw material Substances 0.000 claims 2
- 229920001429 chelating resin Polymers 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 239000008280 blood Substances 0.000 abstract description 3
- 210000004369 blood Anatomy 0.000 abstract description 3
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010812 external standard method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- 244000198896 Lagerstroemia speciosa Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- IMQSIXYSKPIGPD-YQRUMEKGSA-N filipin III Chemical compound CCCCC[C@@H](O)[C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)\C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O IMQSIXYSKPIGPD-YQRUMEKGSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
The invention discloses an extracting method and making method of Colosolic acid (CRA), which comprises the following steps: extracting Banaba leaf in the low-grade intoxic alcohol; filtering the extract; adsorbing the filtrate through large-hole adsorbing resin; desorbing through hydrophilic solvent; collecting CRA desorbing position; condensing in the vacuum; freezing; drying; obtaining the product with purity between 20% and 60%; fitting for controlling blood sugar; treating melituria and losing weight.
Description
Technical field
The invention belongs to the vegetable chemistry technical field, be specifically related to extraction, the preparation method of a kind of triterpene compound Colosolicacid (CRA).
Background technology
Colosolic acid (CRA) is a kind of natural product, and it mainly is present in the leaf of plant Lagerstroemiaspeciosa.In South East Asia, the leaf of this kind of plant is used as herbtherapy diabetes, controlling obesity always and is extensive use of.Filipine Tagalog claims that this plant is Banaba, thereby gain the name " Ba Naba ".Show that after deliberation CRA is the main active ingredient of Banaba, relevant report proof CRA can reduce the blood sugar of test white mouse and the test white mouse that suffers from hereditary diabetes is had hypoglycemic activity, CRA can activate the transmission of glucose, therefore can lowering blood glucose, effect with treatment diabetes, fat-reducing, praise promising glucokinin one title, can be applicable to fields such as medicine, food, protective foods.Therefore the extraction preparation method who researchs and develops CRA has important practical significance.
Extract present report seldom about the preparation of CRA, the Banaba plant is used as local herbal medicine to some extent in South East Asia, but in international academic research, not to the pharmacokinetic of CRA, report is not relevant yet tests the human body effect.CRA has confirmed its pharmaceutical use as the pure natural plants extract in the people's prolonged application of South East Asia, but the preparation extraction of CRA is not still had effective means.
Summary of the invention:
Technical problem to be solved by this invention is to study a kind ofly extracts the production method of CRA product from Banaba, and Environmental Safety, cycle are short, simple to operate, the technology of energy suitability for industrialized production.
The invention provides the extraction preparation method of a kind of triterpene compound Colosolic acid (CRA).
The inventive method with the Banaba leaf through water carry, alcohol extracting, extract CRA to greatest extent, extracting solution filters through 1-0.45 micron membranes strainer, removes undissolved impurity.Adopt the nonpolar or low-pole resin of macroporous type to adorn post as stopping composition, under 20～60 ℃, CRA in the extracting solution is adsorbed, and with between gradient zones in 40%～95% low-alcohol solution desorb, collection contains the cut of CRA, and cut vacuum concentration to the solid content that collection is obtained is to carry out lyophilize at 25% o'clock, and concentrated solution is carried out making finished product after the lyophilize, this finished product detects through HPLC, and the CRA product content is 20～60%.
Method of the present invention specifically comprises the following steps:
(1) the Banaba leaf is immersed in the nontoxic rudimentary (C that 8-10 doubly measures
2-C
3) extract 3 times each 2-3 hour in the alcohol;
(2) extracting solution is used 0.1-0.5 μ micro-filtrate membrane filtration, filtrate merga pass macroporous adsorbent resin;
(3) will adsorb the nontoxic lower alcohol flushing of saturated macroporous adsorbent resin with gradient, dominant discharge 4-5BV/h desorbs CRA, and stripping liquid detects by HPLC, collects to be rich in the CRA part;
(4) stripping liquid obtains the CRA product through 80 ℃ of vacuum concentration, lyophilize, detects with HPLC, and content is 20～60%.
Present method adopts is to adopt the nonpolar or low-pole polymeric adsorbent of macroporous type that CRA is carried out fractionation by adsorption, utilizes the absorption of the nonpolar or low-pole resin CRA of team of macropore and can wash-out under the lower alcohol condition of suitable concn goes out the principle of CRA.Effectively enrichment CRA, the CRA content in the products obtained therefrom can be risen to 20～60%, theoretical yield is 80%～90%.
The inventive method has that technology is simple, product purity is high, with short production cycle, advantage that cost is low.It is 20%～60% that the CRA product that adopts the inventive method to extract preparation detects purity through HPL.
Description of drawings:
The HPLC of Fig. 1 CRA product detects, and retention time is that the peak of 12.146min is the CRA signal among the figure.
Specific embodiment
Embodiment one.
Take by weighing Banaba leaf 500g, with 8 times of 4 liters of 40% ethanol of amount, refluxing extraction 4 times is used ethanol 4L at every turn, and each extracted 60 minutes, united extraction liquid, with extracting solution with 0.1 μ micro-filtrate membrane filtration.Get the D101 resin 300g dress post that cleans up, extracting solution is passed through this resin, flow velocity 3BV/h.At first use 40% ethanol of 1L, the flushing resin; Use the flow velocity wash-out CRA of 80% ethanol of 1.5L then, collect this stream part with 3BV/h.With elutriant under 60 vacuum concentration to about 500ml, then with the concentrated solution lyophilize.Obtain the CRA powder, be weighed as 9.72g, detect through the HPLC external standard method, CRA content is 21.06%, and the rate of recovery is 81.9%.
Embodiment two.
Take by weighing Banaba leaf 300g, with 6 times of amount 60% n-propyl alcohol 3L, refluxing extraction 3 times is used n-propyl alcohol 3L at every turn, and each extracted 80 minutes, united extraction liquid, with extracting solution with 0.2 μ film vacuum filtration.Get the ADS-5 resin 300g dress post that cleans up, by this resin, flow velocity is 3BV/h with extracting solution.At first the n-propyl alcohol with 1L60% washes resin; Use the flow velocity wash-out CRA of 80% n-propyl alcohol of 1.5L then, collect this flow point with 2BV/h.With elutriant under 70 vacuum concentration to 500ml, then with the concentrated solution lyophilize.The CRA powder weighing that obtains is 2.72g, detects through the HPLC external standard method, and CRA content is 29.58%, and the rate of recovery is 53.7%.
Embodiment three.
Take by weighing Banaba leaf 200g, with 6 times of amount 70% Virahol 4L, refluxing extraction 3 times is used Virahol 4L at every turn, and each extracted 80 minutes, and united extraction liquid is with extracting solution 8000 rev/mins of processing of whizzer.Get the HP20 resin 100g dress post that cleans up, by this resin, flow velocity is 3BV/h with centrifugal gained extracting solution.At first with 600ml 70% Virahol flushing resin; Use the flow velocity wash-out CRA of the Virahol of 800ml 90% then, collect this flow point with 2BV/h.With elutriant under 70 vacuum concentration to 300ml, then with the concentrated solution lyophilize.Obtain the CRA powder, be weighed as 0.654g, detect through the HPLC external standard method, CRA content is 51.38%, the rate of recovery 33.6%.
Claims (4)
1, the present invention discloses extraction, the preparation method of a kind of triterpene compound Colosolic acid, it is characterized in that this method comprises the following steps:
(1) the Banaba leaf is immersed in the C of 8-10 times of raw material weight
2-C
3Extract in the alcohol, extract 3 times, each 2-3 hour;
(2) extracting solution is used 0.1-0.5 μ micro-filtrate membrane filtration, filtrate merga pass macroporous adsorbent resin;
(3) will adsorb the C of saturated macroporous adsorbent resin with gradient
2-C
3The alcohol flushing, dominant discharge 4-5BV/h, desorb Colosolic acid, stripping liquid detects by HPLC appearance method, collects to be rich in Colosolic acid part;
(4) be 20～25% o'clock with stripping liquid through 80 ℃ of vacuum concentration to solids content, lyophilize obtains Colosolic acid product, detects with HPLC appearance method, and content is 20～60%.
2, extraction, the preparation method of a kind of triterpene compound Colosolic acid according to claim 1 is characterized in that wherein said raw material must select for use Colosolic acid content at the plant Banaba leaf more than 0.5%.
3, extraction, the preparation method of a kind of triterpene compound Colosolic acid according to claim 1 is characterized in that wherein said macroporous adsorbent resin is styrene tyle macroporous nonpolar or low-pole resin: macroporous resin D series, ADS series, HP series or Amberlite XAD.
4, extraction, the preparation method of a kind of triterpene compound Colosolic acid according to claim 1 is characterized in that described hydrophilic organic solvent is C
2-C
3Primary alconol or secondary alcohol class: ethanol or propyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100257923A CN100564392C (en) | 2006-04-18 | 2006-04-18 | A kind of extraction of triterpene compound, preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100257923A CN100564392C (en) | 2006-04-18 | 2006-04-18 | A kind of extraction of triterpene compound, preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101058596A true CN101058596A (en) | 2007-10-24 |
| CN100564392C CN100564392C (en) | 2009-12-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100257923A Expired - Fee Related CN100564392C (en) | 2006-04-18 | 2006-04-18 | A kind of extraction of triterpene compound, preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100564392C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532239A (en) * | 2010-12-24 | 2012-07-04 | 苏州宝泽堂医药科技有限公司 | Method for extracting demethylzeylasteral from thunder god vine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003018043A1 (en) * | 2001-08-31 | 2003-03-06 | Ohio University | Compositions and methods for treating subjects with hyperglycemia |
-
2006
- 2006-04-18 CN CNB2006100257923A patent/CN100564392C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532239A (en) * | 2010-12-24 | 2012-07-04 | 苏州宝泽堂医药科技有限公司 | Method for extracting demethylzeylasteral from thunder god vine |
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| Publication number | Publication date |
|---|---|
| CN100564392C (en) | 2009-12-02 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20091202 Termination date: 20210418 |