Journal
ORGANIC LETTERS
Volume 24, Issue 23, Pages 4182-4186Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01443
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Funding
- National Research Foundation (NRF) grant from the Korean government [NRF-2020R1A2C2102603]
- Korea Institute of Marine Science & Technology Promotion (KIMST) - Ministry of Oceans and Fisheries [KIMST-20220526]
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Ovataline, a polar metabolite from marine dinoflagellate, inhibits the activity of type II 5α-reductase in prostate cells.
Ovataline (1), which is a polar metabolite containing a hexahydroquinoline moiety, was isolated from cultures of the marine dinoflagellate Ostreopsis cf. ovata. 1 was characterized as a zwitterionic compound with hexahydroquinoline and tetrahydropyran rings. The configurations of the chiral centers in 1 were established using ROESY correlations, Piased configurational and Mosher reaction analyses, and density functional theory calculations. 1 exhibited a 78% (1 mu M) inhibition of type II 5 alpha-reductase in testosterone propionate-induced RWPE-1 human prostatic cells.
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