Two 18-membered epothilones from Sorangium cellulosum So0157-2

The Journal of Antibiotics
2010.0

Abstract

Epothilones are 16-membered ring macrolides originally isolated from Sorangium cellulosum Soce90 that kill dividing cells by stabilizing microtubules. Previously, S. cellulosum So0157-2 was found to produce epothilones, with production of epothilones A and B optimized to industrial scales and five new glycoside derivatives isolated. As part of ongoing efforts to discover new epothilones from this strain, we focused on minor and polar components from large-scale fermentations. The strain was cultivated in 70 l M26 medium, and through repeated column chromatography (Sephadex LH-20, RP-18, silica gel) and HPLC (C18 column, 65% methanol elution), two new epothilone-type 18-membered ring macrolides (named epothilones M and N) were isolated, along with known epothilones A9, A, B, and C. Their structures were established via HR quadrupole time-of-flight MS and NMR data: epothilone M (1) is an 18-membered macrolide with an ester bond between the oxymethylene group (H-17) and carboxyl group (C-1), while epothilone N (2) is 12,13-deepoxy-12-chloro-13-hydroxyl epothilone M. Cytotoxic activity against the MDA-MB-435 cell line (MTT method) showed epothilone M (IC50 0.12 μM) and epothilone A9 (IC50 0.26 μM) had similar activity, whereas epothilone N (IC50 2.47 μM) exhibited modest activity. These 18-membered epothilones from a wild-type strain represent a new structural type of epothilones, and their in vitro cytotoxicity suggests potential for antitumor drug discovery, with bioengineering of the strain to produce more derivatives and in vivo activity testing warranted.

Knowledge Graph

Similar Paper

Two 18-membered epothilones from Sorangium cellulosum So0157-2
The Journal of Antibiotics 2010.0
New Natural Epothilones from <i>Sorangium </i><i>c</i><i>ellulosum</i>, Strains So ce90/B2 and So ce90/D13:  Isolation, Structure Elucidation, and SAR Studies
Journal of Natural Products 2001.0
New Natural Epothilones from <i>Sorangium </i><i>c</i><i>ellulosum</i>, Strains So ce90/B2 and So ce90/D13:  Isolation, Structure Elucidation, and SAR Studies
Journal of Natural Products 2001.0
Five new epothilone metabolites from Sorangium cellulosum strain So0157-2
The Journal of Antibiotics 2009.0
Epothilone A and B—Novel 16‐Membered Macrolides with Cytotoxic Activity: Isolation, Crystal Structure, and Conformation in Solution
Angewandte Chemie International Edition in English 1996.0
Epothilons A and B: Antifungal and Cytotoxic Compounds from Sorangium cellulosum (Myxobacteria). Production, Physico-chemical and Biological Properties.
The Journal of Antibiotics 1996.0
Isolation and Characterization of New Epothilone Analogues from Recombinant <i>Myxococcus </i><i>x</i><i>anthus </i>Fermentations
Journal of Natural Products 2003.0
Isolation and Characterization of New Epothilone Analogues from Recombinant <i>Myxococcus </i><i>x</i><i>anthus </i>Fermentations
Journal of Natural Products 2003.0
A New Cytotoxic Epothilone from Modified Polyketide Synthases Heterologously Expressed in <i>Myxococcus </i><i>x</i><i>anthus</i>
Journal of Natural Products 2002.0
A New Cytotoxic Epothilone from Modified Polyketide Synthases Heterologously Expressed in <i>Myxococcus </i><i>x</i><i>anthus</i>
Journal of Natural Products 2002.0