Issue 33, 2017, Issue in Progress

Chroman-4-one and pyrano[4,3-b]chromenone derivatives from the mangrove endophytic fungus Diaporthe phaseolorum SKS019

Abstract

Seven new compounds: diaporchromanones A–D (1–4), (−)-phomopsichin A (5a), (+)-phomopsichin B (6a), and (±)-diaporchromone A (7), along with the known (+)-phomopsichin A (5b) and (−)-phomopsichin B (6b) were isolated from an endophytic fungus Diaporthe phaseolorum SKS019. The structures of the new compounds, including their absolute configurations, were determined on the basis of HRESIMS and NMR spectroscopic data, and experimental ECD and Rh2(OCOCF3)4-induced CD spectra analyses. Diaporchromanone A (1)/B (2), and C (3)/D (4) are two pairs of 3-epimers, and their structures possessing 3-substituted-chroman-4-one skeleton are rarely found in natural sources. (−)-Phomopsichin A (5a) and (+)-phomopsichin B (6a) are enantiomers of (+)-phomopsichin A (5b) and (−)-phomopsichin B (6b), respectively. All of the isolates were evaluated for their inhibitory effects against osteoclastogenesis in the RAW 264.7 cell line using luciferase reporter gene assays. Compounds 3–6b exhibited moderate inhibitory effects on osteoclastogenesis by suppressing the receptor activator of NF-κB by ligand-induced NF-κB activation.

Graphical abstract: Chroman-4-one and pyrano[4,3-b]chromenone derivatives from the mangrove endophytic fungus Diaporthe phaseolorum SKS019

Supplementary files

Article information

Article type
Paper
Submitted
14 Mar 2017
Accepted
30 Mar 2017
First published
06 Apr 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 20128-20134

Chroman-4-one and pyrano[4,3-b]chromenone derivatives from the mangrove endophytic fungus Diaporthe phaseolorum SKS019

H. Cui, M. Ding, D. Huang, Z. Zhang, H. Liu, H. Huang and Z. She, RSC Adv., 2017, 7, 20128 DOI: 10.1039/C7RA03032K

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