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Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper

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journal contribution
posted on 10.02.2020 by Apisada Jiso, Siriporn Kittiwisut, Ruttanaporn Chantakul, Supreeya Yuenyongsawad, Sumaitt Putchakarn, Till F. Schäberle, Prapapan Temkitthaworn, Kornkanok Ingkaninan, Kulathida Chaithirayanon, Anuchit Plubrukarn
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.