Diaporindenes A-D: Four Unusual 2,3-Dihydro-1 H-indene Analogues with Anti-inflammatory Activities from the Mangrove Endophytic Fungus Diaporthe sp. SYSU-HQ3

The Journal of Organic Chemistry
Hui CuiZhigang She

Abstract

Diaporindenes A-D (1-4), four unusual 2,3-dihydro-1 H-indene isomers, a novel isoprenylisobenzofuran A (5), two new isoprenylisoindole alkaloids diaporisoindoles D and E (6 and 7), and a new benzophenone derivative tenellone D (11), together with four known biogenetic agents (8-10 and 12), were all separated from the endophytic fungus Diaporthe sp. SYSU-HQ3 guided by ultraperformance liquid chromatography high-resolution mass spectrometry. The absolute configurations of 1-7 and 11 were defined by X-ray diffraction, quantum chemical calculations, and spectroscopic analysis. Diaporindenes A-D (1-4) possessed an unprecedented chemical skeleton featuring a 2,3-dihydro-1 H-indene ring and a 1,4-benzodioxan moiety. All of the isolates (1-12) were tested for their inhibitory effects on the production of nitric oxide in lipopolysaccharide-induced microglial cells (RAW 264.7 cells). Compounds 1-5, 8, and 9 were found to exhibit significant inhibitory effects against nitric oxide production with IC50 values from 4.2 to 9.0 μM and SI values from 3.5 to 6.9. In addition, the structure-activity relationships of all compounds were summarized.

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Citations

Sep 30, 2019·Natural Products and Bioprospecting·Rufin Marie Kouipou Toghueo
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Aug 12, 2020·Natural Product Reports·Huomiao Ran, Shu-Ming Li
Sep 18, 2020·Organic & Biomolecular Chemistry·Huibo LiuWeimin Zhang
Apr 26, 2020·Planta medica·Pragya Paramita PalA Sajeli Begum
Apr 1, 2020·Organic & Biomolecular Chemistry·Le Thi Ngoc ChucDuen-Ren Hou
Aug 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zheng NiuWeimin Zhang
Feb 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hongju LiuZhigang She
Nov 19, 2019·Journal of Asian Natural Products Research·Yan Fei Liu, Shi-Shan Yu
Feb 4, 2021·Journal of Natural Products·Sharna-Kay Daley, Geoffrey A Cordell
Jul 7, 2020·Journal of Microbiology and Biotechnology·Kashvintha NagarajanWen-Nee Tan
Jun 29, 2021·Natural Product Research·Yu-Jie PengGe-Lei Xiao
Aug 1, 2019·Journal of Natural Products·Runlin CaiZhigang She
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