| An efficient chemical method for separation of corsolic acid from its isomeric maslinic acid. | |
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MedLine Citation:
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PMID: 16854724 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Based on the difference in steric bulk around C12-C13 double bond, the two isomeric dihydroxy pentacyclic triterpenic acids viz: corsolic acid and maslinic acid have been quantitatively separated via their methyl esters by reacting with the bulky m-chloroperbenzoic acid. Corsolic acid methyl ester was obtained in pure form, whereas maslinic acid methyl ester was separated as 12-oxo derivative formed via its epoxide. Alkaline hydrolysis of corsolic acid methyl ester afforded the desired acid. This method was also found to work well with the isomeric amyrin mixture (alpha- and beta-), but not highly selective. The high selectivity of this method with corsolic maslinic acid system can be rationalized in terms of 2alpha-hydroxy functionality, which provides additional crowding around the double bond and completely prevented corsolic acid from its reaction with perbenzoic acid. |
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Authors:
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Uppuluri V Mallavadhani; Anita Mahapatra; Satyabrata Mohapatra |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Natural product research Volume: 20 ISSN: 1478-6419 ISO Abbreviation: Nat. Prod. Res. Publication Date: 2006 Aug |
Date Detail:
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Created Date: 2006-07-20 Completed Date: 2006-09-19 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101167924 Medline TA: Nat Prod Res Country: England |
Other Details:
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Languages: eng Pagination: 946-52 Citation Subset: IM |
Affiliation:
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Centre for Herbal Drugs, Regional Research Laboratory (CSIR), Bhubaneswar-751 013, India. uvmavadani@rrlbhu.res.in |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Chlorobenzoates
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chemistry* Chromatography, Gel Diospyros / chemistry* Esterification Isomerism Nuclear Magnetic Resonance, Biomolecular Optical Rotation Plant Leaves / chemistry Spectrometry, Mass, Fast Atom Bombardment Spectroscopy, Fourier Transform Infrared Triterpenes / chemistry, isolation & purification* |
| Chemical | |
Reg. No./Substance:
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0/Chlorobenzoates; 0/Triterpenes; 4373-41-5/maslinic acid; 937-14-4/3-chloroperbenzoic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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