4 years ago

Site-selective oxidation of unactivated C–H sp3 bonds of oleanane triterpenes by Streptomyces griseus ATCC 13273

Site-selective oxidation of unactivated C–H sp3 bonds of oleanane triterpenes by Streptomyces griseus ATCC 13273
The oxidization of unactivated C–H bonds is of great interests in the structural modification of pentacyclic triterpenes. Herein we discovered the unique capability of Streptomyces griseus ATCC 13273 to catalyze the site-selective oxidation of C-29 methyl group to carboxyl group over a range of oleanane triterpenes, oleanolic acid (1), hederagenin (2), echinocystic acid (3), quillaic acid (4) and senegenin (5). Along with this reaction the hydroxylation on C-24 and C-21 were also discovered on some substrates. As a result, eight new compounds (1c, 2a5a and 2b∼4b) among the ten metabolites were isolated. The anti-inflammatory activities of these compounds were evaluated against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages, and the products with hydroxyl group on C-21 (1c, 2b and 5a) showed significantly enhanced activities with the IC50 values of 1.230, 0.078 and 0.015 μM, respectively. Thus S. griseus ATCC 13273 was further proved as a useful biocatalyst to expand the structural diversity of oleanane triterpenes for medicinal chemistry research.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017304192

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.