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

• Published in: Journal of natural products (Washington, D.C.) Vol. 83; no. 2; pp. 532 - 536
• Main Authors: Jiso, Apisada, Kittiwisut, Siriporn, Chantakul, Ruttanaporn, Yuenyongsawad, Supreeya, Putchakarn, Sumaitt, Schäberle, Till F, Temkitthaworn, Prapapan, Ingkaninan, Kornkanok, Chaithirayanon, Kulathida, Plubrukarn, Anuchit
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 28.02.2020; Amer Chemical Soc
• Subjects: 5-alpha Reductase Inhibitors - chemistry; 5-alpha Reductase Inhibitors - isolation & purification; 5-alpha Reductase Inhibitors - pharmacology; Animals; Chemistry, Medicinal; Finasteride - chemistry; Finasteride - isolation & purification; Finasteride - pharmacology; Humans; Life Sciences & Biomedicine; Male; Molecular Structure; Pharmacology & Pharmacy; Plant Sciences; Porifera - chemistry; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; AUSTRALIAN MARINE SPONGE; 5-ALPHA-REDUCTASE; QUINONE; INHIBITORS; HYDROQUINONE
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.9b00886

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.