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J Org Chem. 2018 Oct 5;83(19):11804-11813. doi: 10.1021/acs.joc.8b01738. Epub 2018 Sep 5.

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.

Cui H1,2, Liu Y3, Li J4, Huang X1, Yan T5, Cao W5, Liu H1,4, Long Y1,6, She Z1.

Author information

1
School of Chemistry , Sun Yat-Sen University , Guangzhou 510275 , China.
2
School of Pharmaceutical Sciences , Guangzhou University of Chinese Medicine , Guangzhou , 510006 , China.
3
State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine , Sun Yat-Sen University Cancer Center , Guangzhou 510060 , China.
4
School of Pharmacy , Guangdong Medical University , Dongguan , 523808 , China.
5
South China Sea Institute of Oceanology , Chinese Academy of Sciences , Guangzhou 510301 , China.
6
School of Chemistry and Environment , South China Normal University , Guangzhou 510006 , China.

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.

PMID:
30141629
DOI:
10.1021/acs.joc.8b01738

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