PMID: 11908965Mar 23, 2002Paper

Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products

Journal of Natural Products
Toshihiro AkihisaHoyoku Nishino

Abstract

Microbial transformation of betulin (1), a lupane-type triterpene obtained from the bark extract of white birch (Betula platyphylla Sukatshev var. japonica), and its chemical oxidation product, betulonic acid (2), by the fungus Chaetomium longirostre yielded 4,28-dihydroxy-3,4-seco-lup-20(29)-en-3-oic acid (3) and 4-hydroxy-3,4-seco-lup-20(29)-ene-3,28-dioic acid (4) from 1, and 4,7beta,17-trihydroxy-3,4-seco-28-norlup-20(29)-en-3-oic acid (5) and 7 beta,15 alpha-dihydoxy-3-oxolup-20(29)-en-28-oic acid (6) from 2. The four metabolites, 3-6, along with 1 and 2, were evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for inhibitors of tumor promotion. All of the triterpenes tested showed potent inhibitory effects, with the four metabolites 3-6 exhibiting the more potent effects.

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Citations

Sep 14, 2007·Investigational New Drugs·Praveen RajendranAnand C Burman
Sep 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tatiane C de CarvalhoNiege A J C Furtado
Nov 26, 2013·Journal of Asian Natural Products Research·Haq Nawaz Bhatti, Rasheed Ahmad Khera
May 1, 2010·Natural Product Research·Leonardo Ribeiro Martins, Jacqueline Aparecida Takahashi
Oct 11, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Nighat Sultana, Zafar Saeed Saify
Dec 13, 2005·Bioorganic & Medicinal Chemistry·Carolina P ReyesIsabel L Bazzocchi
May 6, 2011·Chemical Reviews·Hannes LeischPeter C K Lau

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