Issue 8, 2018

Isolation and biosynthesis of labdanmycins: four new labdane diterpenes from endophytic Streptomyces

Abstract

Chemical investigation of Streptomyces sp. KIB 015, an endophyte from the plant Panax notoginseng, led to the discovery of two novel labdane diterpenes, labdanmycins A (1) and B (2). In order to reveal the biosynthesis of labdanmycins, the genome of S. sp. KIB 015 was sequenced and a lab gene cluster encoding GGPP synthase, class II cyclase, class I cyclase, and cytochrome P450s was confirmed to be involved in labdanmycin biosynthesis by heterologous expression and gene inactivation experiments. Biogenetic precursor raimonol (3) was isolated from the gene labE inactivation mutant strain S. sp. KIB 015 ΔlabE, which suggested that P450 enzyme LabE is responsible for oxidizing the C-20 methyl group of 3 to an aldehyde or carbonyl group to afford 1 and 2. Additional two new labdane diterpenes (4 and 5) were also isolated from the mutant S. sp. KIB 015 ΔlabE. The chemical structures of 1–5 were elucidated on the basis of extensive NMR and MS spectroscopic analyses.

Graphical abstract: Isolation and biosynthesis of labdanmycins: four new labdane diterpenes from endophytic Streptomyces

Supplementary files

Article information

Article type
Research Article
Submitted
25 jan 2018
Accepted
28 feb 2018
First published
01 mar 2018

Org. Chem. Front., 2018,5, 1272-1279

Isolation and biosynthesis of labdanmycins: four new labdane diterpenes from endophytic Streptomyces

Z. Xiong, J. Huang, Y. Yan, L. Wang, Z. Wang, J. Yang, J. Luo, J. Li and S. Huang, Org. Chem. Front., 2018, 5, 1272 DOI: 10.1039/C8QO00085A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements