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Gymnopalynes A and B, Chloropropynyl-isocoumarin Antibiotics from Cultures of the Basidiomycete Gymnopus sp.

2013; American Chemical Society; Volume: 76; Issue: 11 Linguagem: Inglês

10.1021/np400609f

1520-6025

Benjarong Thongbai, Frank Surup, Kathrin I. Mohr, Eric Kuhnert, Kevin D. Hyde, Marc Stadler,

Marine Sponges and Natural Products

A chlorinated isocoumarin with an acetylenyl side chain and its 3,4-dihydro derivative, named gymnopalynes A (1) and B (2), were isolated from cultures of a basidiomycete originating from the rain forest of Northern Thailand. The producing organism was identified as a species of Gymnopus (Marasmiaceae). Their structures were elucidated by spectroscopic methods including UV/vis and NMR spectroscopy as well as high-resolution mass spectrometry as 3-(3-chloroprop-1-yn-1-yl)-1H-isochromen-1-one (1) and 3-(3-chloroprop-1-yn-1-yl)-3,4-dihydro-1H-isochromen-1-one (2). The absolute stereochemistry of 2 was assigned as S by CD spectroscopy. Both compounds showed weak to moderate antimicrobial and pronounced cytotoxic activities.