title: Gymnopalynes A and B, chloropropynyl-isocoumarin antibiotics from cultures of the basidiomycete Gymnopus sp.
abstract: 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.
authors.affiliation: Institute of Excellence in Fungal Research and School of Science, Mae Fah Luang University , Chiang Rai 57100, Thailand.
authors.forename: Benjarong
authors.initials: B
authors.lastname: Thongbai
authors.forename: Frank
authors.initials: F
authors.lastname: Surup
authors.forename: Kathrin
authors.initials: K
authors.lastname: Mohr
authors.forename: Eric
authors.initials: E
authors.lastname: Kuhnert
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Hyde
authors.forename: Marc
authors.initials: M
authors.lastname: Stadler
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D049934:Isocoumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013785:Thailand
chemical_list: D000900:Anti-Bacterial Agents; D049934:Isocoumarins; C586140:gymnopalyne A; C586139:gymnopalyne B