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Inhibitory Effects of Constituents of an Endophytic Fungus Hypoxylon investiens on Nitric Oxide and Interleukin‐6 Production in RAW264.7 Macrophages
Author(s) -
Chang ChunWei,
Chang HsunShuo,
Cheng MingJen,
Liu TaWei,
Hsieh SungYuan,
Yuan GwoFang,
Chen IhSheng
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300364
Subject(s) - chemistry , nitric oxide , quercetin , stereochemistry , positive control , fungus , endophyte , biochemistry , traditional medicine , botany , biology , organic chemistry , medicine , antioxidant
Three new compounds, hypoxyloamide ( 1 ), 8‐methoxynaphthalene‐1,7‐diol ( 2 ), and hypoxylonol ( 3 ), together with seven compounds isolated from nature for the first time, investiamide ( 4 ), hypoxypropanamide ( 5 ), hypoxylonol A ( 6 ), investienol ( 7 ), 2‐heptylfuran ( 8 ), (3 S )‐5‐methyl‐8‐ O ‐methylmellein ( 9 ), (4 R )‐ O ‐methylsclerone ( 10 ), along with 19 known compounds, 11 – 29 , were isolated from the culture broth of Hypoxylon investiens BCRC 10F0115, a fungal endophyte residing in the stems of an endemic Formosan plant Litsea akoensis var. chitouchiaoensis. The structures of the new compounds were established by spectroscopic methods, including UV, IR, HR‐ESI‐MS, and extensive 1D‐ and 2D‐NMR techniques. Of these isolates, 2 , 8‐methoxynaphthalen‐1‐ol ( 15 ), and 1,8‐dimethoxynaphthalene ( 16 ) showed nitric oxide (NO) inhibitory activity with IC 50 values of 11.8±0.9, 17.8±1.1, and 13.3±0.5 μ M , respectively, stronger than the positive control quercetin ( IC 50 36.8±1.3 μ M ). Compounds 2, 15 , and 16 also showed interleukin‐6 (IL‐6) inhibitory activity with IC 50 values of 9.2±1.7, 18.0±0.6, and 2.0±0.1 μ M , stronger than the positive control quercetin ( IC 50 31.3±1.6 μ M ). To the best of our knowledge, this is the first report on guaiane sesquiterpene metabolites, 3, 6 , and 7 , from the genus Hypoxylon.