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Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum

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Abstract

Bistachybotrysins L–V (1–11), eleven novel dimeric phenylspirodrimanes, were isolated from the fungus Stachybotrys chartarum CGMCC 3.5365. Among them, 1 and 2, a pair of stereoisomeric dimers represent an unusual aromatic [5,6]-spiroketal skeleton with a central 2-methoxy-1,6-dioxaspiro[4.5]decane core fused with two phenyl units. Their structures, including absolute configurations, were elucidated using extensive spectroscopic data, single-crystal X-ray diffraction (Cu Kα), and calculated electronic circular dichroism (ECD) analyses. Biological assay revealed that 2 showed potent cytotoxicity against five human tumor cell lines with IC50 values in the range of 1.8–3.5 μM; 2, 3, and 9 displayed neuroprotective effects toward the glutamate-induced toxicity in SK-N-SH cells by increasing cell viability 17.4%–17.6% at 10.0 μM; and 8 exhibited anti-inflammatory activity by suppressing LPS-induced NO production in BV2 cells with an inhibition rate of 54.2% at 10.0 μM. Furthermore, the possible biogenetic pathways of these compounds are proposed.

Graphical abstract: Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum

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Article information


Submitted
20 Oct 2019
Accepted
25 Dec 2019
First published
26 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum

J. Liu, X. Jia, J. Zhao, J. Feng, M. Chen, R. Chen, K. Xie, D. Chen, Y. Li, D. Zhang, Y. Peng, S. Si and J. Dai, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01284B

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