Benzophenones from Guignardia sp. IFB-E028, an Endophyte on Hopea hainanensis

• Published in: Chemistry & biodiversity 2010-01, Vol.7 (1), p.216-220
• Main Authors: Wang, Feng-Wu, Ye, Yong-Hao, Ding, Hui, Chen, Yun-Xi, Tan, Ren-Xiang, Song, Yong-Chun
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Ascomycota - chemistry; Ascomycota - metabolism; Benzophenone dimers; Benzophenones - chemistry; Benzophenones - isolation & purification; Benzophenones - toxicity; Dipterocarpaceae - microbiology; Guignardia; Guignardia sp. IFB-E028; Guignasulfide; Helicobacter pylori; Helicobacter pylori - drug effects; Hep G2 Cells; Hopea hainanensis; Humans; Sulfides - chemistry; Sulfides - isolation & purification; Sulfides - toxicity
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.200800353

The first natural S‐containing benzophenone dimer, named guignasulfide (3), was isolated from the culture of Guignardia sp. IFB‐E028, an endophytic fungus residing in healthy leaves of Hopea hainanensis. Its structure was determined through correlative analyses of its MS, 1D‐ and 2D‐NMR spectroscopic data. Two other known benzophenone derivatives, monomethylsulochrin and rhizoctonic acid (1 and 2, resp.) were also isolated. Guignasulfide (3) was more active against the human liver cancer cell line HepG2 (IC50 value: 5.2±0.4 μM) than metabolites 1 and 2 (IC50 values: 63.5±0.6 and 60.2±0.5 μM); compounds 1–3 showed also moderately inhibitory effects on the human bacterial pathogen Helicobacter pylori with MIC values of 28.9±0.1, 60.2±0.4, and 42.9±0.5 μM, respectively.