Facile synthesis of oleanolic acid monoglycosides and diglycosides.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yu ShaMao-Sheng Cheng

Abstract

Oleanolic acid and its glycosides are important natural products, possessing various attractive biological activities such as antitumor, antivirus and anti-inflammatory properties. In the present work, fifteen oleanolic acid saponins bearing various saccharide moieties, including 3-monoglycoside, 28-monoglycoside and 3,28-diglycoside, were easily synthesized in high yields. Benzyl was chosen as the protective group for the COOH(28) group, instead of commonly used methyl and allyl, to avoid difficulties in the final deprotection. Alkali-promoted condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new idea for the corresponding synthetic methods to the glycoside derivatives of other triterpenoid.

References

Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·R R Schmidt, W Kinzy
Dec 1, 1995·Journal of Ethnopharmacology·J Liu
Jul 31, 1999·Bioorganic & Medicinal Chemistry·Y LiM Yoshikawa
Jun 3, 2006·Natural Product Reports·Petr DzubakJan Sarek
Jun 13, 2006·Bioorganic & Medicinal Chemistry Letters·Mao-Cai YanMao-Sheng Cheng

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Citations

Apr 15, 2010·Journal of Asian Natural Products Research·Shan QianYong Wu
Oct 1, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniele F FelipeDiógenes A G Cortez
Nov 7, 2012·Expert Opinion on Drug Metabolism & Toxicology·David J Greenblatt, Gary K Zammit
May 7, 2013·Phytochemistry·Naima BoutaghaneZahia Kabouche
May 12, 2009·Carbohydrate Research·Maria Carmen del Ruiz RuizPaul Kosma
Nov 10, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yang LiuMao-Sheng Cheng
Jan 29, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hanqing ZhaoXiaomei Liang

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Methods Mentioned

BETA
glycosylation
gel
gel column chromatography
column chromatography

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