[go: up one dir, main page]

US20130211136A1 - Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof - Google Patents

Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof Download PDF

Info

Publication number
US20130211136A1
US20130211136A1 US13/704,616 US201113704616A US2013211136A1 US 20130211136 A1 US20130211136 A1 US 20130211136A1 US 201113704616 A US201113704616 A US 201113704616A US 2013211136 A1 US2013211136 A1 US 2013211136A1
Authority
US
United States
Prior art keywords
oil palm
oil
extracts
palm
shikimic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/704,616
Inventor
Sambandan Tg
ChoKyun Rha
Ravigadevi Sambanthamurthi
Anthony J. Sinskey
Yew Ai Tan
Kalyana Sundram P. Manickam
Mohd Basri Wahid
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Malaysian Palm Oil Board MPOB
Original Assignee
Malaysian Palm Oil Board MPOB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Malaysian Palm Oil Board MPOB filed Critical Malaysian Palm Oil Board MPOB
Publication of US20130211136A1 publication Critical patent/US20130211136A1/en
Assigned to MALAYSIAN PALM OIL BOARD reassignment MALAYSIAN PALM OIL BOARD ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WAHID, MOHD BASRI, MANICKAM, KALYANA SUNDRAM P., TAN, YEW AI, SAMBANTHAMURTHI, RAVIGADEVI, RHA, CHOKYUN, SINSKEY, ANTHONY J., TG, SAMBANDAN
Priority to US15/414,058 priority Critical patent/US9963415B2/en
Priority to US15/943,777 priority patent/US10308583B2/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/50—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1085—Transferases (2.) transferring alkyl or aryl groups other than methyl groups (2.5)
    • C12N9/1092—3-Phosphoshikimate 1-carboxyvinyltransferase (2.5.1.19), i.e. 5-enolpyruvylshikimate-3-phosphate synthase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y205/00—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5)
    • C12Y205/01—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5) transferring alkyl or aryl groups, other than methyl groups (2.5.1)
    • C12Y205/01019—3-Phosphoshikimate 1-carboxyvinyltransferase (2.5.1.19), i.e. 5-enolpyruvylshikimate-3-phosphate synthase
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention generally relates to a method to obtain and produce shikimic acid from plants and plant based materials, and more particularly to a method for producing shikimic acid based on oil palm and oil palm based materials.
  • Shikimic Acid is an imperative biochemical intermediate in plants and microorganisms, and has emerged as a vital starting material in the synthesis of an anti-influenza drug, widely known as Tamiflu (oseltamivir). It is discovered to be highly functionalized and it plays a major role in the production of essential aromatic amino acids which are not synthesized in the human body, such as phenylalanine, tryptophan and tryrosine.
  • shikimic acid can be obtained based on microbe-catalyzed synthesis schemes or from plants, whereby the primary plant-based source for shikimic acid is the star anise (Illicium anisatum), whereby the yield of shikimic acid from star anise seed can be as high as 7%.
  • Oseltamivir also known as the trade name Tamiflu, aids in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B infection, by way of blocking the influenza virus from spreading between cells and body.
  • the administration of oseltamivir is preferably conducted within 48 hours from the first appearance of flu symptoms, as during this period it is observed that the virus has yet to replicate and infect many cells thus inhibition is considerably more effective.
  • the compound from Tamiflu is hydrolyzed by esterases in the liver, forming active form of drug, which is the oseltamivir carboxylate. Oseltamivir carboxylate then binds to and thereby inhibits viral neuralminidase.
  • Such inhibition of neuraminidase by Tamiflu and other neuraminidase inhibitors prevents the release of new virus from the infected host cells.
  • shikimic acid As shikimic acid cannot be synthesized economically, the notion in shortage of shikimic acid has been surfaced due to increasing demand and consequently researchers began bioprospecting in many areas, in their endeavours to find alternative sources apart from star anise seed as briefly mentioned above. Accordingly, shikimic acid content has been discovered in a number of plants, particularly in the seeds of the sweetgum fruit, the Indian plant Calophylium apetalum and Araucaria excelsea . Nevertheless it has been observed that these plants produce toxic compounds that necessitate prohibitively expensive refinement methods to ensure and thus obtain purified shikimc acid.
  • oil palm (Elaies guineensis) is in the oil, which offers various health advantages and benefits, owing to its high content of phytonutrients demonstrate antioxidant properties. Nevertheless, at present, the oil palm based extracts, in particular its vegetation liquour and palm oil mill effluent (POME), has been discovered by way of various studies to have beneficial implications on skin ageing, cancer and heart diseases.
  • POME vegetation liquour and palm oil mill effluent
  • Malaysia is currently one of the world's largest producers of palm oil. Being the major foreign exchange earner industry and to fulfill the rapid progression of the world's demand for palm oil based on the world population growth, Malaysia has at least 265 palm oil mills all over the country.
  • the extraction of palm oil which is the primary product of palm fruit, involves a combination of various processes, wherein the main steps include the reception of fresh fruit bunches from plantations, sterilizing and threshing of the bunches, mashing the fruit and pressing the crude palm oil prior to storage and exportation.
  • the extraction of palm oil leads to the production of oil palm vegetation liquor which is discarded in the waste stream as Palm Oil Mill Effluent (POME).
  • PME Palm Oil Mill Effluent
  • EFB Empty Fruit Bunches
  • other waste materials are discarded in the milling process
  • Palm oil mill effluent for instance, if untreated, is a pollutant due to the high chemical oxygen demand (COD) and biological oxygen demand (BOD).
  • COD chemical oxygen demand
  • BOD biological oxygen demand
  • the major components of POME include oil and grease and solids, while elements found in POME include phosphorus, potassium, boron, iron, manganese, copper, magnesium and zinc. So far POME has been used in the preparation of fertilizers or as a substrate for bacterial production of biodegradable plastics.
  • OPP oil palm phenolics
  • the extracts comprises oil palm phenolics (OPP) obtained from oil palm-based materials.
  • OPP oil palm phenolics
  • shikimic acid are purified from the OPP extracts.
  • OPP extracts are obtained from palm oil vegetation liquor.
  • OPP extracts are obtained from palm oil mill effluent (POME).
  • composition containing shikimic acid wherein said shikimic acid is obtained from extracts of oil palm.
  • a method for producing shikimic acid comprises the steps of obtaining extracts from oil palm based materials.
  • oil palm based materials including vegetation liquors, any oil palm by products, palm oil milling wastes materials, oil palm based waste materials (liquid and solid), materials from oil palm based industries, any ancillary oil palm vegetative matters, any part of the oil palm tree for instance but not limiting to the stem, pulp, seed, trunk, fruitlet, fruitbunch, frond, any part of the oil palm fruit and other oil palm based materials and sources not name explicitly herein.
  • the method further includes the step of obtaining extracts from oil palm based materials preferably without using solvents.
  • the method may include the step of obtaining water soluble, and enriched with phenolic compounds, extracts from oil palm based materials.
  • the step of obtaining extracts from oil palm based materials may be performed based on conventional separation principles. It should be noted that however the method involved for extraction is solvent-free.
  • the method may further includes the step of obtaining water soluble, antioxidant rich extracts known as oil palm phenolics (OPP) from oil palm based materials including vegetation liquors, any oil palm by products, palm oil milling wastes materials, materials from oil palm based industries, any ancillary oil palm vegetative matters, any part of the oil palm tree for instance but not limiting to the stem, pulp, seed, trunk, fruitlet, fruitbunch, frond, any part of the oil palm fruit and other oil palm based materials and sources not name explicitly herein.
  • OPP oil palm phenolics
  • the extracts may be obtained from materials used or generated from oil palm based industries.
  • the extraction of the oil palm phenolics (OPP) as briefly described above in accordance with a preferred embodiment of the present invention may involve the steps of providing three-phase decantor system, and preferably a plurality of separation stages using different types of membranes suitably adapted to separate residual oil, ionic contaminants and components of high molecular weight, thereby obtaining oil palm phenolics (OPP).
  • oil palm phenolics (OPP) in accordance with an embodiment of the present invention can be obtained from palm oil mill effluent (POME).
  • palm oil mill effluent (POME) is a thick brownish liquid that contains approximately 4% solids by dry weight.
  • POME can be a source of nutrient content (Zakaria et. al) upon treated to reduce the organic load (Ma et al.). Conventionally, the treated POME may be recycled to the field.
  • shikimic acid is purified from said oil palm phenolics (OPP).
  • the method further includes the step of extraction or purifying shikimic acid from the oil palm based materials extracts.
  • preparation of the extracts, oil palm or parts of oil palm may be treated with glyphosate, a compound typically used in eliminating unwanted plants especially weeds, so as to increase levels or obtain high yield of shikimic acid.
  • glyphosate inhibits the exnzyme EPSP synthase, thus condenses shikimate-3-phosphate and phosphore-enol-pyruvate to form 5-enolpyruvylshikimate-3-phosphate, a precursor of chorismate. It is understood that the dose of glyphosate is suitably controlled to as to allow maximum yield of shikimic acid.
  • extracts from oil palm based materials or OPP extracts can be scaled up to accommodate larger or more substantial extraction batch sizes desired.
  • HPLC was carried out on a sample of OPP extracts. Results obtained to show the presence and HPLC profile of shikimic acid are as shown in FIG. 1 .
  • the determination of elements within the extracts can be carried out using various standard procedures, for instance, but not limiting to, mass spectroscopy.
  • a Nuclear magnetic resonance (NMR) analysis may further be carried out to confirm such purification.
  • extraction and purification of shikimic acid from OPP may be conducted based on standard purification methods.
  • the extract and purification can be scaled up to accommodate larger or more substantial extraction batch sizes desired.
  • the yield of shikimic acid obtained from OPP is approximately 1% of the dry weight. It is expected that the amount may increase if plant is treated with glyphosate prior to extracting the OPP.
  • Shikimic acid obtained based on the present invention may be used as an immunomodulatory agent.
  • incubation of peripheral blood mononuclear cells with shikimic acid in combination with the polyphenol quercetin led to an increase in the release of chemokines IL-8 and IL-6, whereby these chemokines play a major role in recruiting and activating lymphocytes for the innate immunity system.
  • chemokines IL-8 and IL-6 chemokines
  • Such discovery therefore demonstrates that shikimic acid and quercetin from dietary may enhance the innate immunity system, which would be beneficial for combating viral infections (Bertelli et. al).
  • the shikimic acid obtained may be used in the treatment for hair loss.
  • an experiment was conducted and water soluble extracts containing shikimic acid obtained from Illicium anisatum (aniseed) has been reported to be able to aid in increasing subcutaneous blood flow and in mice and thus stimulate the elongation of mouse follicles in culture (Sakaguchi et. al.)
  • the OPP extracts containing shikimic acid obtained from oil palm based materials may be used to make, or are contained in but not limiting to, drinks, edible products, health supplements, antioxidant additives, cosmeceutical products or medicinal products.
  • oil palm based materials can be considered as the most abundant and inexpensive source for shikimic acid. It is estimated that 46 million tons of palm oil mill effluent (POME) can be produced yearly.
  • POME palm oil mill effluent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Zoology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Fats And Perfumes (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides compositions and method for production of shikimic acid based on extracts obtained from oil palm-based materials, and more particularly oil palm based waste materials and by-products. The method includes purifying shikimic acid from extracts comprising oil palm phenolics (OPP).

Description

    CLAIM OF PRIORITY
  • This non-provisional application is a national phase application in USA for PCT Application No. PCT/MY2011/000097 filed on Jun. 16, 2011, which claims priority to Malaysian Patent Application No. PI2010002835 filed on Jun. 16, 2010.
    • FIELD OF INVENTION
  • The invention generally relates to a method to obtain and produce shikimic acid from plants and plant based materials, and more particularly to a method for producing shikimic acid based on oil palm and oil palm based materials.
    • BACKGROUND OF THE INVENTION
  • Reference to any prior art in this specification is not, and should not be taken as, an acknowledgement or any form of suggestion that this prior art forms part of the common general knowledge in Malaysia or any other country.
  • Shikimic Acid (SA) is an imperative biochemical intermediate in plants and microorganisms, and has emerged as a vital starting material in the synthesis of an anti-influenza drug, widely known as Tamiflu (oseltamivir). It is discovered to be highly functionalized and it plays a major role in the production of essential aromatic amino acids which are not synthesized in the human body, such as phenylalanine, tryptophan and tryrosine. Presently, shikimic acid can be obtained based on microbe-catalyzed synthesis schemes or from plants, whereby the primary plant-based source for shikimic acid is the star anise (Illicium anisatum), whereby the yield of shikimic acid from star anise seed can be as high as 7%.
  • Oseltamivir, also known as the trade name Tamiflu, aids in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B infection, by way of blocking the influenza virus from spreading between cells and body. The administration of oseltamivir is preferably conducted within 48 hours from the first appearance of flu symptoms, as during this period it is observed that the virus has yet to replicate and infect many cells thus inhibition is considerably more effective. Under normal circumstances, the compound from Tamiflu is hydrolyzed by esterases in the liver, forming active form of drug, which is the oseltamivir carboxylate. Oseltamivir carboxylate then binds to and thereby inhibits viral neuralminidase. Such inhibition of neuraminidase by Tamiflu and other neuraminidase inhibitors prevents the release of new virus from the infected host cells.
  • It is observed based on current conditions that the primary challenge in oseltamivir production is the availability of a viable source of shikimic acid. As shikimic acid cannot be synthesized economically, the notion in shortage of shikimic acid has been surfaced due to increasing demand and consequently researchers began bioprospecting in many areas, in their endeavours to find alternative sources apart from star anise seed as briefly mentioned above. Accordingly, shikimic acid content has been discovered in a number of plants, particularly in the seeds of the sweetgum fruit, the Indian plant Calophylium apetalum and Araucaria excelsea. Nevertheless it has been observed that these plants produce toxic compounds that necessitate prohibitively expensive refinement methods to ensure and thus obtain purified shikimc acid.
  • It is being reported that at least 50 million people have been treated with oseltamivir and this amount is expected to increase within the upcoming years. It is further estimated that the market size for Tamiflu will be at 400 million doses per year, at which 130 mg of shikimic acid is required to synthesize one dose of Tamiflu. From here, it can be expected that at least 52 metric tons of shikimic acid is required to meet the upcoming demands. Although production can be increased by way of replacing isolation from plant sources with recombinant microbial catalysts following the need but shortage of shikimic acid will intermittently be a challenging factor especially in the occurrence of a pandemic worldwide.
  • Following this there is a great need to provide a renewable and inexpensive source or viable alternative sources of shikimic acid.
  • The commercial value of oil palm (Elaies guineensis) is in the oil, which offers various health advantages and benefits, owing to its high content of phytonutrients demonstrate antioxidant properties. Nevertheless, at present, the oil palm based extracts, in particular its vegetation liquour and palm oil mill effluent (POME), has been discovered by way of various studies to have beneficial implications on skin ageing, cancer and heart diseases.
  • Malaysia is currently one of the world's largest producers of palm oil. Being the major foreign exchange earner industry and to fulfill the rapid progression of the world's demand for palm oil based on the world population growth, Malaysia has at least 265 palm oil mills all over the country.
  • Typically, the extraction of palm oil which is the primary product of palm fruit, involves a combination of various processes, wherein the main steps include the reception of fresh fruit bunches from plantations, sterilizing and threshing of the bunches, mashing the fruit and pressing the crude palm oil prior to storage and exportation. However, the extraction of palm oil leads to the production of oil palm vegetation liquor which is discarded in the waste stream as Palm Oil Mill Effluent (POME). In addition Empty Fruit Bunches (EFB) and other waste materials are discarded in the milling process
  • Palm oil mill effluent (POME) for instance, if untreated, is a pollutant due to the high chemical oxygen demand (COD) and biological oxygen demand (BOD). The major components of POME include oil and grease and solids, while elements found in POME include phosphorus, potassium, boron, iron, manganese, copper, magnesium and zinc. So far POME has been used in the preparation of fertilizers or as a substrate for bacterial production of biodegradable plastics.
  • It is being reported that more than 500 kg (around 0.5 m3) of liquid wastes, primarily in the form of palm oil mill effluent (POME), are discharged during the processing of 1.0 metric tons of fresh fruit bunches (Ma et al. 1996) in a typical oil palm mill. Accordingly, it is expected that more than 50 m3 of POME from a mill after processing 100 metric tons of fresh fruit bunches.
  • Proceeding from the above and based on recent studies on phytochemicals extracted from oil palm, the palm oil industry creates an abundance of prospect in beneficial phytochemicals and other compounds recovery due to the amount of oil palm based materials including waste materials generated from the industry, if treated effectively.
  • It is a primary object of the present invention to provide a method for production of shikimic acid based on oil palm extracts.
  • It is yet another object of the present invention to provide a method for production of shikimic acid based on oil palm by-products.
  • It is another object of the present invention to provide a composition and a method for producing a composition comprising shikimic acid obtained from oil palm vegetation liquor.
  • It is yet another object of the present invention to provide a composition and a method for producing shikimic acid obtained from palm oil mill effluent (POME).
  • It is yet another object of the present invention to provide a composition comprising shikimic acid obtained from extracts from oil palm-based materials and method for producing said shikimic acid based on oil palm based materials.
  • It is yet another object of the present invention to provide a composition comprising oil palm phenolics (OPP) with shikimic acid content and method for producing said shikimic acid based on oil palm based materials.
  • It is yet a further object of the present invention to provide a composition and method for producing shikimic acid obtained from oil palm liquid waste based materials.
  • Further objects and advantages of the present invention may become apparent upon referring to the preferred embodiments of the present invention as shown in the accompanying drawings and as described in the following description.
    • SUMMARY OF INVENTION
  • There is disclosed a method for production of shikimic acid comprising the step of obtaining extracts from oil palm-based materials.
  • It is disclosed that the extracts comprises oil palm phenolics (OPP) obtained from oil palm-based materials.
  • It is further disclosed that the shikimic acid are purified from the OPP extracts.
  • It is further disclosed that the OPP extracts are obtained from palm oil vegetation liquor.
  • It is further disclosed that the OPP extracts are obtained from palm oil mill effluent (POME).
  • In another aspect of the present invention there is disclosed a composition containing shikimic acid, wherein said shikimic acid is obtained from extracts of oil palm.
    • DETAILED DESCRIPTION OF THE INVENTION
  • In line with the above summary, the disclosed description and examples relates to a composition comprising shikimic acid and method of producing the said shikimic acid based on oil palm based materials. It shall be apparent however to one skilled in the art that the exemplifications are provided to better elucidate the embodiments of the present invention and therefore should not be construed as limiting the scope of protection.
  • As briefly described earlier, during oil palm fruit processing, the extraction of palm oil generates a waste stream of vegetation liquor, which is thereby considered as an aqueous phase of the milling process prior to being discarded as palm oil mill effluent (POME) and solid wastes.
  • In one embodiment of the present invention, a method for producing shikimic acid comprises the steps of obtaining extracts from oil palm based materials is disclosed. Suitably, it should be noted that oil palm based materials including vegetation liquors, any oil palm by products, palm oil milling wastes materials, oil palm based waste materials (liquid and solid), materials from oil palm based industries, any ancillary oil palm vegetative matters, any part of the oil palm tree for instance but not limiting to the stem, pulp, seed, trunk, fruitlet, fruitbunch, frond, any part of the oil palm fruit and other oil palm based materials and sources not name explicitly herein.
  • The method further includes the step of obtaining extracts from oil palm based materials preferably without using solvents.
  • In one embodiment of the present invention, the method may include the step of obtaining water soluble, and enriched with phenolic compounds, extracts from oil palm based materials.
  • In accordance with the present invention, the step of obtaining extracts from oil palm based materials may be performed based on conventional separation principles. It should be noted that however the method involved for extraction is solvent-free.
  • According to the present invention, the method may further includes the step of obtaining water soluble, antioxidant rich extracts known as oil palm phenolics (OPP) from oil palm based materials including vegetation liquors, any oil palm by products, palm oil milling wastes materials, materials from oil palm based industries, any ancillary oil palm vegetative matters, any part of the oil palm tree for instance but not limiting to the stem, pulp, seed, trunk, fruitlet, fruitbunch, frond, any part of the oil palm fruit and other oil palm based materials and sources not name explicitly herein.
  • Based on another embodiment of the present invention, the extracts may be obtained from materials used or generated from oil palm based industries.
  • In another embodiment of the present invention, the extraction of the oil palm phenolics (OPP) as briefly described above in accordance with a preferred embodiment of the present invention may involve the steps of providing three-phase decantor system, and preferably a plurality of separation stages using different types of membranes suitably adapted to separate residual oil, ionic contaminants and components of high molecular weight, thereby obtaining oil palm phenolics (OPP).
  • As an example, oil palm phenolics (OPP) in accordance with an embodiment of the present invention can be obtained from palm oil mill effluent (POME). Generally palm oil mill effluent (POME) is a thick brownish liquid that contains approximately 4% solids by dry weight. POME can be a source of nutrient content (Zakaria et. al) upon treated to reduce the organic load (Ma et al.). Conventionally, the treated POME may be recycled to the field. In one embodiment of the present invention, shikimic acid is purified from said oil palm phenolics (OPP).
  • According to the present invention, the method further includes the step of extraction or purifying shikimic acid from the oil palm based materials extracts.
  • In accordance with a preferred embodiment of the present invention, preparation of the extracts, oil palm or parts of oil palm may be treated with glyphosate, a compound typically used in eliminating unwanted plants especially weeds, so as to increase levels or obtain high yield of shikimic acid. It is observed that glyphosate inhibits the exnzyme EPSP synthase, thus condenses shikimate-3-phosphate and phosphore-enol-pyruvate to form 5-enolpyruvylshikimate-3-phosphate, a precursor of chorismate. It is understood that the dose of glyphosate is suitably controlled to as to allow maximum yield of shikimic acid.
  • It is understood that the extracts from oil palm based materials or OPP extracts can be scaled up to accommodate larger or more substantial extraction batch sizes desired.
  • In order to determine the radical scavenging activity of the OPP prepared for the purpose of the present invention, standard procedures may be carried out. Such may include, but not limiting to, conducting Flash Chromatography or High Performance Liquid Chromatography (HPLC) on the OPP extracts. Results showing the compounds are obtained and presented in chromatograms. A free radical scavenging activity based on the plotted graph of obtained fractions and absorbance may be provided.
  • As an example, HPLC was carried out on a sample of OPP extracts. Results obtained to show the presence and HPLC profile of shikimic acid are as shown in FIG. 1.
  • In accordance with a preferred embodiment of the present invention, the determination of elements within the extracts can be carried out using various standard procedures, for instance, but not limiting to, mass spectroscopy.
  • A Nuclear magnetic resonance (NMR) analysis may further be carried out to confirm such purification.
  • In an embodiment of the present invention, extraction and purification of shikimic acid from OPP may be conducted based on standard purification methods. Suitably, it is understood that the extract and purification can be scaled up to accommodate larger or more substantial extraction batch sizes desired.
  • According to the present invention, the yield of shikimic acid obtained from OPP is approximately 1% of the dry weight. It is expected that the amount may increase if plant is treated with glyphosate prior to extracting the OPP.
  • An example of estimates of the amount of palm oil mill effluent (POME) may be required for production of shikimic acid at different extraction efficiencies are as depicted in TABLE 1 below:
  • 10% market 50% market 100% market
    demand = demand = demand =
    1 kg 5,200 Kg 26,000 Kg 52,000 Kg
    3.1% Shikimic 25 tons 132,000 tons 660,270 tons 1,320,000 tons
    acid yield
    form dry mass
    0.5% Shikimic  5 tons 26,4000 tons 132,000 tons   264,000 tons
    acid yield
    from dry mass
    1% Shikimic 2.5 tons   13,200 tons  66,000 tons   132,000 tons
    acid yield
    from dry mass
  • Apart from being the primary building block in the production of Tamiflu, shikimic acid has been reported based on various recent studies, to provide other various health related benefits.
  • Shikimic acid obtained based on the present invention may be used as an immunomodulatory agent. As an example, in an in-vitro model, incubation of peripheral blood mononuclear cells with shikimic acid in combination with the polyphenol quercetin led to an increase in the release of chemokines IL-8 and IL-6, whereby these chemokines play a major role in recruiting and activating lymphocytes for the innate immunity system. Such discovery therefore demonstrates that shikimic acid and quercetin from dietary may enhance the innate immunity system, which would be beneficial for combating viral infections (Bertelli et. al).
  • In accordance with the present invention, the shikimic acid obtained may be used in the treatment for hair loss. As an example, an experiment was conducted and water soluble extracts containing shikimic acid obtained from Illicium anisatum (aniseed) has been reported to be able to aid in increasing subcutaneous blood flow and in mice and thus stimulate the elongation of mouse follicles in culture (Sakaguchi et. al.)
  • Further in accordance to the present invention, the OPP extracts containing shikimic acid obtained from oil palm based materials may be used to make, or are contained in but not limiting to, drinks, edible products, health supplements, antioxidant additives, cosmeceutical products or medicinal products.
  • From the foregoing it is disclosed that oil palm based materials can be considered as the most abundant and inexpensive source for shikimic acid. It is estimated that 46 million tons of palm oil mill effluent (POME) can be produced yearly.
  • It is understood by a person skilled in the art that the methods for experiments and studies are described as exemplifications herein and thus the results are not intended, however, to limit or restrict the scope of the invention in any way and should not be construed as providing conditions, parameters, agents or starting materials which must be utilized exclusively in order to practice the present invention. It is therefore understood that the invention may be practiced, within the scope of the appended claims, with equivalent methods for the experiments than as specifically described and stated in claims.

Claims (16)

1. A method for production of shikimic acid comprising the step of obtaining extracts from oil palm-based materials.
2. A method as claimed in claim 1 further comprising purifying said shikimic acid from said extracts from oil palm-based materials.
3. A method as claimed in claim 1 wherein the extracts are obtained from oil palm by-products.
4. A method as claimed in claim 1 wherein the extracts are obtained from oil palm based waste materials.
5. A method as claimed in claim 1 wherein the extracts are obtained from oil palm liquid waste materials.
6. A method as claimed in claim 1 wherein the extracts are obtained from palm oil vegetation liquor.
7. A method as claimed in claim 1 wherein the extracts are obtained from materials from oil palm based industries.
8. A method as claimed in claim 1 to 4 wherein the extracts are obtained from palm oil mill effluent (POME).
9. A method as claimed in claim 1 wherein the extracts are obtained from anyone of the following oil palm based materials; oil palm by products, palm oil milling wastes materials, materials from oil palm based industries, any ancillary oil palm vegetative matters, any part of the oil palm tree for instance but not limiting to the stem, pulp, seed, trunk, fruitlet, fruitbunch, frond, any part of the oil palm fruit and other oil palm based materials and sources.
10. A method as claimed in claim 1 wherein the extracts comprise of oil palm phenolics (OPP).
11. A method as claimed in claim 1 wherein said extracts are water soluble and enriched with anti-oxidants.
12. A method as claimed in claim 1 wherein the method further comprising treating said oil palm with glyphosate prior to obtaining the extracts from said oil palm-based materials.
13. A composition containing shikimic acid, characterized in that said shikimic acid is obtained from extracts of oil palm or oil palm based materials.
14. A composition as claimed in claim 13 wherein the extracts comprise of oil palm phenolics (OPP).
15. A composition as claimed in claim 13 to 14 wherein said shikimic acid is obtained from palm oil mill effluent (POME).
16. A composition as claimed in claim 13 wherein the shikimic acid is obtained from palm oil vegetation liquor.
US13/704,616 2010-06-16 2011-06-16 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof Abandoned US20130211136A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US15/414,058 US9963415B2 (en) 2010-06-16 2017-01-24 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
US15/943,777 US10308583B2 (en) 2010-06-16 2018-04-03 Compositions comprising shikimic acid obtained from oil palm-based materials

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
MYPI2010002835A MY160702A (en) 2010-06-16 2010-06-16 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
MYPI201002835 2010-06-16
PCT/MY2011/000097 WO2011159144A1 (en) 2010-06-16 2011-06-16 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/MY2011/000097 A-371-Of-International WO2011159144A1 (en) 2010-06-16 2011-06-16 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/414,058 Division US9963415B2 (en) 2010-06-16 2017-01-24 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof

Publications (1)

Publication Number Publication Date
US20130211136A1 true US20130211136A1 (en) 2013-08-15

Family

ID=45348382

Family Applications (3)

Application Number Title Priority Date Filing Date
US13/704,616 Abandoned US20130211136A1 (en) 2010-06-16 2011-06-16 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
US15/414,058 Active US9963415B2 (en) 2010-06-16 2017-01-24 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
US15/943,777 Active US10308583B2 (en) 2010-06-16 2018-04-03 Compositions comprising shikimic acid obtained from oil palm-based materials

Family Applications After (2)

Application Number Title Priority Date Filing Date
US15/414,058 Active US9963415B2 (en) 2010-06-16 2017-01-24 Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
US15/943,777 Active US10308583B2 (en) 2010-06-16 2018-04-03 Compositions comprising shikimic acid obtained from oil palm-based materials

Country Status (7)

Country Link
US (3) US20130211136A1 (en)
EP (1) EP2582654B1 (en)
CN (1) CN103097334A (en)
BR (1) BR112012031900A2 (en)
CO (1) CO6670556A2 (en)
MY (1) MY160702A (en)
WO (1) WO2011159144A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11045400B2 (en) * 2016-07-27 2021-06-29 Kemon S.P.A. Topical cosmetic composition for restructuring and protecting hair and scalp, and uses thereof

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY160702A (en) * 2010-06-16 2017-03-15 Malaysian Palm Oil Board Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
MY160083A (en) 2012-11-26 2017-02-15 Sime Darby Malaysia Berhad A method for isolating shikimic acid from oil palm waste
MY178049A (en) * 2013-02-21 2020-09-30 Malaysian Palm Oil Board Composition with inhibitory effect on viral integrase activity
WO2014189356A1 (en) * 2013-05-21 2014-11-27 Sime Darby Malaysia Berhad Processes for extracting protein from or increasing protein content of palm kernel cake
WO2014189357A1 (en) * 2013-05-21 2014-11-27 Sime Darby Malaysia Berhad A process for extracting phenolic compound
MY186191A (en) * 2013-06-28 2021-06-30 Malaysian Palm Oil Board Isolation of novel bioactive compound obtained from oil palm base materials
WO2018165780A1 (en) * 2017-03-17 2018-09-20 Malaysian Palm Oil Board Antioxidant, anti-inflammatory compositions and uses thereof
GB2560710B (en) * 2017-03-17 2021-10-20 Malaysian Palm Oil Board Compositions comprising oil palm phenolics and shikimic acid or derivatives thereof and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070148266A1 (en) * 2003-10-30 2007-06-28 Loders Croklaan B.V. Pine needle extract

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070264412A1 (en) 2003-10-30 2007-11-15 Youchun Yan Food Product Comprising an Extract From Pine Needles
CA2643916A1 (en) 2006-03-17 2007-09-27 Herbalscience Singapore Pte. Ltd. Extractions and methods comprising elder species
CN101415332A (en) * 2006-03-17 2009-04-22 草药科学新加坡私人有限公司 Extractions and methods comprising elder species
CL2008000934A1 (en) 2008-03-31 2009-03-27 Botanical Solutions S P A Method of preparation of quillaja saponaria molina extracts, extract obtained by said procedure and comprising saponins among other bioactive secondary metabolites, and its use for the control of b. cinerea in pre or post-harvest.
MY170986A (en) * 2009-05-26 2019-09-23 Malaysian Palm Oil Board Composition comprising caffeoylshikimic acids, protocatechuic acid, hydroxytyrosol, hydroxybenzoic acid and their derivatives and method of preparation thereof
MY160702A (en) * 2010-06-16 2017-03-15 Malaysian Palm Oil Board Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070148266A1 (en) * 2003-10-30 2007-06-28 Loders Croklaan B.V. Pine needle extract

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11045400B2 (en) * 2016-07-27 2021-06-29 Kemon S.P.A. Topical cosmetic composition for restructuring and protecting hair and scalp, and uses thereof

Also Published As

Publication number Publication date
BR112012031900A2 (en) 2017-11-28
CN103097334A (en) 2013-05-08
US20170129842A1 (en) 2017-05-11
EP2582654A1 (en) 2013-04-24
US10308583B2 (en) 2019-06-04
US9963415B2 (en) 2018-05-08
US20180222837A1 (en) 2018-08-09
CO6670556A2 (en) 2013-05-15
EP2582654A4 (en) 2015-12-16
MY160702A (en) 2017-03-15
EP2582654B1 (en) 2018-01-17
WO2011159144A1 (en) 2011-12-22

Similar Documents

Publication Publication Date Title
US10308583B2 (en) Compositions comprising shikimic acid obtained from oil palm-based materials
Rahmanian et al. Recovery and removal of phenolic compounds from olive mill wastewater
Aguilar et al. Production of antioxidant nutraceuticals by solid-state cultures of pomegranate (Punica granatum) peel and creosote bush (Larrea tridentata) leaves
AU2004276123B2 (en) Fermentation and culture method, fermented plant extract, fermented plant extract powder and composition containing the fermented plant extract
Daâssi et al. Olive oil mill wastewaters: Phenolic content characterization during degradation by Coriolopsis gallica
US20090053333A1 (en) Treatment of vegetation liquors derived from oil-bearing fruit
De et al. Effect of fish waste hydrolysate on growth, survival, health of Penaeus vannamei and plankton diversity in culture systems
KR101207899B1 (en) The producing process of functional and fermented material containing taurine and GABA by fermentation with oyster
KR20140146638A (en) Method for Production of L-Methionine and Related Products
GB2528793A (en) Triazine compound for combating coccidiosis in chickens
Lenora et al. Eichhornia crassipes (Mart.) Solms.-An alternate renewable source for Shikimic acid, a precursor for Tamiflu, a swine flu drug
WO2012067491A2 (en) Compositions comprising extracts obtained from oil palm based materials for providing anti -inflammatory effects and method of producing thereof
Guvem et al. Redefining the waste: Sustainable management of olive mill waste for the recovery of phenolic compounds and organic acids
NL2020952B1 (en) Method for producing inositol and inorganic phosphate
CN101784205B (en) Method for producing distilled olive juice extract
CN102006782A (en) Purification of protein hydrolysate and the resultant products
KR101751110B1 (en) Application of animals' whole blood for preapring high concentration amino acids powder and the preparing method thereof
CA2612975C (en) Dioctatin composition and use for inhibition of aflatoxin production and method for controlling aflatoxin contamination using dioctatin
CN1217671C (en) Fish brain oil and its extraction method
JP7464951B2 (en) Disuse muscle atrophy inhibitor and food composition for inhibiting disuse muscle atrophy
JP2012077058A (en) Influenza virus neuraminidase inhibitor
WO2007138607A1 (en) Method for obtaining shikimic acid
KR20240079156A (en) Method of shikimic acid extraction using Conifer
CN112516621A (en) Preparation method of high-content Chinese prickly ash flavone
JP2004352681A (en) Agent for suppressing cancer cell growth and method for producing the same

Legal Events

Date Code Title Description
AS Assignment

Owner name: MALAYSIAN PALM OIL BOARD, MALAYSIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:TG, SAMBANDAN;RHA, CHOKYUN;SAMBANTHAMURTHI, RAVIGADEVI;AND OTHERS;SIGNING DATES FROM 20140925 TO 20141231;REEL/FRAME:034874/0218

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION