WO2013160881A1 - Method for obtaining an extract rich in triterpenic acids from eucalyptus barks - Google Patents
Method for obtaining an extract rich in triterpenic acids from eucalyptus barks Download PDFInfo
- Publication number
- WO2013160881A1 WO2013160881A1 PCT/IB2013/053318 IB2013053318W WO2013160881A1 WO 2013160881 A1 WO2013160881 A1 WO 2013160881A1 IB 2013053318 W IB2013053318 W IB 2013053318W WO 2013160881 A1 WO2013160881 A1 WO 2013160881A1
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- WIPO (PCT)
- Prior art keywords
- previous
- acids
- bark
- triterpenic acids
- eucalyptus
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/028—Flow sheets
- B01D11/0284—Multistage extraction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
Definitions
- the present invention relates to a method of obtaining extracts having very high contents (up to 98 %) of triterpenic acids, mainly oleanolic and ursolic acids, from eucalyptus barks.
- the method involves the solid-liquid extraction of the bark with organic solvents, preferably hexane, and the fractionation of the crude extract by means of a simple treatment with an alkaline solution, followed by separation of the aqueous phase, its filtration, acidification and finally isolation of the enriched triterpenic acids fraction by means of filtration, centrifugation or extraction with an organic solvent, preferably hexane, followed by solvent removal.
- Betulinic acid is known to exhibit anti-HIV, antibacterial, antimalarial, anti-inflammatory and antioxidant properties
- Oleanolic and ursolic acids are known also to have antimicrobial (Horiuchi et al . , 2007, Kuete et al . , 2007, Sattar et al . , 1995) and significant anti-tumour activities
- ursolic acid is a useful suppressive compound for rheumatoid arthritis treatment with low risk of gastric problems (Kang et al . , 2008).
- the novelty of the present invention resides in the use of Eucalyptus bark residues (and particularly Eucalyptus globulus for obtaining extracts with high amounts (up to 98%) of triterpenic acids by means of solid-liquid extraction with an organic solvent, preferably n-hexane, followed by the fractionation through sequential alkaline/acid solutions treatment.
- the proposed method has the advantage of being highly efficient and easily industrialized when compared with some of the technologies available .
- the object of the present invention is a method for obtaining extracts rich in triterpenic acids wherein it comprises the following steps:
- the method further comprises a crystallization step.
- the Eucalyptus bark is obtained from Eucalyptus species, namely E. globulus, E. urograndls , E. grandls x globulus , E. maidenii E. grandis and E. nitens and the residual moisture and granulometry of the bark samples are below 15% and 60 mesh respectively.
- the organic solvent used is dichloromethane, n-heptane, n-hexane or other non-polar solvent and the aqueous solution comprises at least one of: metal hydroxide (KOH or NaOH) or carbonate (Na 2 CC>3 or K 2 CO 3 ) , as well as the corresponding hydrogenocarbonates, or phosphate (Na 3 PC>4 or K 3 PO 4 ) , as well as the corresponding hydrogenophosphates and dihydrogenophosphates , or ammonium hydroxide (NH 4 OH) , being that the pH of the alkaline aqueous solution is between 8 and 14.
- metal hydroxide KOH or NaOH
- carbonate Na 2 CC>3 or K 2 CO 3
- phosphate Na 3 PC>4 or K 3 PO 4
- NH 4 OH ammonium hydroxide
- the separation is performed by decantation or centrifugation .
- the acidification of the aqueous phase is done with inorganic acid solutions, such as sulphuric, hydrochloric and nitric acids, and organic acid solutions, such as acetic, and propionic acids and the pH of the acid solution is between 1 and 5.
- inorganic acid solutions such as sulphuric, hydrochloric and nitric acids
- organic acid solutions such as acetic, and propionic acids
- the pH of the acid solution is between 1 and 5.
- Another object of the present invention is the extracts, obtained by the method described above, wherein the triterpenic acids content is in the range of 93-98%.
- Another object of the present invention is the use of the extracts described above wherein they are used in pharmaceuticals, nutraceuticals , cosmetics and functional food industries. Description of the drawings
- Figure 1 Steps of the method of obtaining extracts enriched in triterpenic acids, from Eucalyptus species barks .
- the present invention relates to a method of obtaining extracts enriched in triterpenic acids, from Eucalyptus species barks, outlined in Fig. 1.
- the method comprises four main steps:
- this process can also comprise a crystallization step .
- the result of this process is a whitish powder with a triterpenic acids content of about 93-98 %.
- the bark used as raw material can be obtained from different Eucalyptus species, namely E. globulus, E. urograndls , E. grandls x globulus , E. maldenll E. grandls and E. nltens , among others.
- Fresh or decayed biomass can be used but should be preferably dried and milled before the solvent extraction.
- the drying and milling steps include known methodologies such as lyophilization, air drying, hot air drying, and any mechanical milling such as, e.g., blade, knife or hammer milling, respectively.
- the residual moisture and granulometry of the bark used in this process are below 15% and 60 mesh, respectively.
- the solvent used for extraction includes non polar organic solvents, preferably n-hexane. This operation can be performed using conventional procedures, such as maceration, extraction under reflux, Soxtec, Soxhlet, accelerated solvent extraction, or any other solid-liquid extraction technique.
- the crude organic extract is then treated with an alkaline aqueous solution, until pH between 8 and 14, preferably NaOH or KOH, or carbonate (Na 2 CC>3 or K 2 CO 3 ) , as well as the corresponding hydrogenocarbonates , or phosphate (Na 3 PC>4 or K 3 PO 4 ) , as well as the corresponding hydrogenophosphates and dihydrogenophosphates , or ammonium hydroxide (NH 4 OH) , to promote the conversion of the triterpenic acids into the corresponding salts and its migration to the aqueous phase.
- the separation of the organic phase is performed by decantation or by any other liquid-liquid separation technique, such as centrifugation .
- the aqueous phase is filtrated, by means of conventional methods, and acidified until pH ⁇ 3 with preferably an inorganic acid, such as sulphuric, hydrochloric and nitric acids and organic acid solutions, such as acetic, and propionic acids.
- an inorganic acid such as sulphuric, hydrochloric and nitric acids
- organic acid solutions such as acetic, and propionic acids.
- the precipitated triterpenic acids can be finally isolated by extraction with an organic solvent, filtration or by centrifugation .
- the extraction of the dried milled bark was performed in a Soxhlet extraction apparatus with 1 L of n-hexane as solvent, at reflux temperature. The extraction lasted 6 hours .
- the 1 L n-hexane crude extract was extracted with 1 L 0.1 M sodium hydroxide (NaOH) aqueous solution.
- the aqueous phase was separated from the n-hexane phase by decantation, and vacuum filtrated through 0.45 ym porosity nylon membranes disks, a clear solution being obtained.
- the said solution was acidified to pH ⁇ 3 with 2 M sulfuric acid (H 2 SO 4 ) resulting in a whitish precipitate suspension.
- the precipitate was vacuum filtrated, washed with 1 L of distilled water up to neutral pH, and dried at 105 °C for 3 h.
- a whitish powder consisting of a sum of triterpenic acids, with a minimum 97.8% by weight content composed of: 52.4% of ursolic acid, 17.3% of oleanolic acid, 13.2% of betulonic acid, 9.7% of betulinic acid, and 5.2% of other triterpenic acids (Fig. 2) .
- Kolomitsyna 0., Krasutsky, P., A., Kacharov, 0., D., Kolomitsyn, I., V., Krasutskyy, D., A, 2005. Method for obtaining natural products from plant material. WO 2005047304. Kuete, V., Eyong, K.O., Folefoc, G.N., Beng, V.P., Hussain, H., Krohn, K., Nkengfack, A.E., 2007. Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. Pharmazie. 62, 552-556.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- Botany (AREA)
- Mycology (AREA)
- Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Epidemiology (AREA)
- Food Science & Technology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Nutrition Science (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Polymers & Plastics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES201490120A ES2525953B2 (es) | 2012-04-26 | 2013-04-26 | Método de obtención de un extracto rico en ácidos triterpénicos de corteza de eucalipto |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PT106278A PT106278B (pt) | 2012-04-26 | 2012-04-26 | Método para a obtenção de um extrato rico em ácidos triterpénicos a partir da casca de eucalipto |
PT106278 | 2012-04-26 |
Publications (1)
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WO2013160881A1 true WO2013160881A1 (en) | 2013-10-31 |
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PCT/IB2013/053318 WO2013160881A1 (en) | 2012-04-26 | 2013-04-26 | Method for obtaining an extract rich in triterpenic acids from eucalyptus barks |
Country Status (3)
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ES (1) | ES2525953B2 (es) |
PT (1) | PT106278B (es) |
WO (1) | WO2013160881A1 (es) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112021339A (zh) * | 2019-06-03 | 2020-12-04 | 南京臻旸生物科技有限公司 | 一种桉树叶和桉树皮制生物农药和生物肥料的方法及产品 |
EP4186575A1 (en) * | 2021-11-30 | 2023-05-31 | Raiz - Instituto De Investigação Da Floresta E Papel | Integrated process for extracting bioactive compounds from eucalyptus biomass |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112021339A (zh) * | 2019-06-03 | 2020-12-04 | 南京臻旸生物科技有限公司 | 一种桉树叶和桉树皮制生物农药和生物肥料的方法及产品 |
EP4186575A1 (en) * | 2021-11-30 | 2023-05-31 | Raiz - Instituto De Investigação Da Floresta E Papel | Integrated process for extracting bioactive compounds from eucalyptus biomass |
Also Published As
Publication number | Publication date |
---|---|
PT106278B (pt) | 2018-01-03 |
ES2525953A2 (es) | 2015-01-02 |
PT106278A (pt) | 2013-10-28 |
ES2525953R1 (es) | 2015-03-24 |
ES2525953A9 (es) | 2015-03-23 |
ES2525953B2 (es) | 2017-06-14 |
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