Apisada JisoSiriporn KittiwisutRuttanaporn ChantakulSupreeya YuenyongsawadSumaitt PutchakarnTill F. SchäberlePrapapan TemkitthawornKornkanok IngkaninanKulathida ChaithirayanonAnuchit PlubrukarnWalailak UniversityNaresuan UniversityJustus Liebig University GiessenMahidol UniversityThammasat UniversityBurapha UniversityPrince of Songkla UniversityFraunhofer Institute for Molecular Biology and Applied Ecology IME2020-03-262020-03-262020-02-28Journal of Natural Products. Vol.83, No.2 (2020), 532-53615206025016338642-s2.0-85079751529https://repository.li.mahidol.ac.th/handle/123456789/53582Copyright © 2020 American Chemical Society and American Society of Pharmacognosy. A chemical investigation of the sponge Verongula cf. rigida led to the isolation of 13 merosesquiterpenes, among which quintaquinone (2), 5-epi-nakijiquinone L (3), and 3-farnesyl-2-hydroxy-5-methoxyquinone (4) were isolated and reported here for the first time. Particularly, compound 2 is the first member of merosesquiterpenes with a polyketide side chain substituted on C-19. All of the isolated compounds were examined for steroid 5α-reductase inhibitory activity. Cyclospongiaquinone 1 (5) showed a strong activity in the same range as that of standard finasteride.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryMedicinePharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1021/acs.jnatprod.9b00886