PDF icon Download PDF
Planta Med 2017; 83(07): 654-660
DOI: 10.1055/s-0042-119650
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Novel Isochroman Dimers from Stachybotrys sp. PH30583: Fermentation, Isolation, Structural Elucidation and Biological Activities

Wei Li   *
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
2   School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, China
,
Ya-Bin Yang   *
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Xue-Qiong Yang
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Hui-Ding Xie
2   School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, China
,
Zhi-Hui Shao
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Hao Zhou
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
,
Cui-Ping Miao
3   Yunnan Institute of Microbiology, Yunnan University, Kunming, China
,
Li-Xing Zhao
3   Yunnan Institute of Microbiology, Yunnan University, Kunming, China
,
Zhong-Tao Ding
1   School of Chemical Science and Technology, Yunnan University, Kunming, China
› Author Affiliations
Further Information

Publication History

received 08 April 2016
revised 10 July 2016

accepted 18 October 2016

Publication Date:
02 November 2016 (online)

Also available ateRef
   Permissions and Reprints
Preview

Abstract

The rare anishidiol and five new isochromans, including three novel dimers with unprecedented skeletons, were isolated from Stachybotrys sp. PH30583. Their structures were determined by spectral analyses. The bioactivities of these compounds were also investigated. The dimers (6–10) inhibited acetylcholinesterase at 50 µM, but the monomers did not. To investigate the biogenesis of the novel dimers, a time-course investigation of metabolite production was undertaken.

Key words

Stachybotrys sp. - Hypocreales - isochroman - bioactivity - dimer - anti-acetylcholinesterase

* W. Li and Y. B. Yang contributed equally to this paper.


Supporting Information

1D, 2D NMR, MS, and CD spectra of the new compounds 2–10 (Figs. 6 S–31 S), HPLC investigation on the metabolic production of these compounds from PH30583 (Fig. 1 S), chiral HPLC analyses of the compounds (Fig. 2 S), lowest-energy conformers of stachydein and stachiol with different configurations (Fig. 3 S), and Tables 1 S with the biological activity test of these compounds are available as Support Information.