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Paper | Regular issue | Vol 87, No. 12, 2013, pp.2501-2512
Published online, 1st November, 2013
DOI: 10.3987/COM-13-12795
DIOSPENTENOLS A AND B, TWO NEW CYCLOPENTAPYRANS ISOLATED FROM ABANDONED MINE BACTERIUM STREPTOMYCES SP. KMA-001

Jin-Soo Park, Jin Wook Cha, Seong-Hwan Kim, Dong-Chan Oh, and Hak Cheol Kwon*

*Natural Medicine Center, Korea Institute of Science and Technology, 679 Saimdang-ro, 210-340, Korea

Abstract

Two new cyclopentapyrans, diospentenols A and B were isolated from the Streptomyces sp. KMA-001 which was isolated from a heat-treated soil sample collected at the abandoned zinc mine. Spectroscopic analyses including extensive 2D NMR spectra, mass spectrometry, and chemical modification revealed structures of diospentenols consisted of 7,7a-dihydro-2H- cyclepenta[b]pyran-6-one core with a hydroxyl group and allyl side chain. This carbon skeleton is rare in natural products reported in the literature. Diosphenol, previously isolated from marine sponge and ascidian, is one of a few known natural products that possess this structural core. Each diospentenol was verified as a racemate using the modified Mosher method and chiral HPLC analysis.