title: Oxirapentyns F-K from the marine-sediment-derived fungus Isaria felina KMM 4639.
abstract: Six new highly oxygenated chromene derivatives, oxirapentyns F-K (2-7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2-9 were determined using spectroscopic methods. The relative configurations of compounds 2-7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher's method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences , Prospect 100-letiya Vladivostoka, 159, Vladivostok 690022, Russian Federation.
authors.forename: Anton N
authors.initials: AN
authors.lastname: Yurchenko
authors.forename: Olga F
authors.initials: OF
authors.lastname: Smetanina
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.forename: Michael A
authors.initials: MA
authors.lastname: Pushilin
authors.forename: Valeriy P
authors.initials: VP
authors.lastname: Glazunov
authors.forename: Yuliya V
authors.initials: YV
authors.lastname: Khudyakova
authors.forename: Natalya N
authors.initials: NN
authors.lastname: Kirichuk
authors.forename: Svetlana P
authors.initials: SP
authors.lastname: Ermakova
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Dyshlovoy
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Yurchenko
authors.forename: Shamil Sh
authors.initials: SSh
authors.lastname: Afiyatullov
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification*; D004354:Drug Screening Assays, Antitumor; D019015:Geologic Sediments / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D006999:Hypocreales / Q000737:chemistry*; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D001578:Benzopyrans; D047630:Depsipeptides; C039875:oxirapentyn