Issue 62, 2017, Issue in Progress

Fermentation of Illigera aromatica with Clonostachys rogersoniana producing novel cytotoxic menthane-type monoterpenoid dimers

Abstract

Illigera aromatica, a medicinal liana, was fermented with Clonostachys rogersoniana. Two novel menthane-type monoterpenoid dimers, dimericilligerates E (1) and F (2) were isolated from the fermented material. Their structures were identified by 1D/2D NMR, electric circular dichroism, derivatization, and Mosher's method. A novel elimination reaction that formed a benzene ring from a menthane moiety afforded derivative 1a, which possesses more resolved NMR signals than the dimeric monoterpenoid, dimericilligerate E (1). The determination of 1a verified the estimation of 1. Compounds 1 and 2 showed potent cytotoxic activities; especially, 1 possessed significant activities against the liver hepatocellular carcinoma cell line (SMMC-7721) with an IC50 value of 3.89 ± 0.23 μM. Three novel precursors, dimericilligerates A–C (3–5), were identified by HPLC-MS and isolated from the original I. aromatica. This paper presents a novel class of monoterpenoid dimers and suggests that C. rogersoniana-fermented I. aromatica is effective to produce cytotoxic dimeric monoterpenoids from inactive original materials.

Graphical abstract: Fermentation of Illigera aromatica with Clonostachys rogersoniana producing novel cytotoxic menthane-type monoterpenoid dimers

Supplementary files

Article information

Article type
Paper
Submitted
31 May 2017
Accepted
17 Jul 2017
First published
09 Aug 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 38956-38964

Fermentation of Illigera aromatica with Clonostachys rogersoniana producing novel cytotoxic menthane-type monoterpenoid dimers

J. Dong, L. Cai, X. Li, R. Mei, J. Wang, P. Luo, Y. Shu and Z. Ding, RSC Adv., 2017, 7, 38956 DOI: 10.1039/C7RA06078E

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