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

  • J Nat Prod. 2020 Feb 28;83(2):532-536. doi: 10.1021/acs.jnatprod.9b00886.
Apisada Jiso  1 ,  Siriporn Kittiwisut  1  2 ,  Ruttanaporn Chantakul  3 ,  Supreeya Yuenyongsawad  1  4 ,  Sumaitt Putchakarn  5 ,  Till F Schäberle  6  7 ,  Prapapan Temkitthaworn  3 ,  Kornkanok Ingkaninan  3 ,  Kulathida Chaithirayanon  8 ,  Anuchit Plubrukarn  1
Affiliations
  • 1. Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences , Prince of Songkla University , Hat-Yai , Songkhla 90112 , Thailand.
  • 2. Division of Pharmaceutical Sciences, Faculty of Pharmacy , Thammasat University , Klong Luang , Pathumthani 12120 , Thailand.
  • 3. Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences , Naresuan University , Phitsanulok 65000 , Thailand.
  • 4. School of Pharmacy , Walailak University , Tha Sala, Nakhon Si Thammarat 80160 , Thailand.
  • 5. Institute of Marine Science , Burapha University , Chonburi 20131 , Thailand.
  • 6. Institute for Insect Biotechnology , Justus-Liebig-University of Giessen , 35392 Giessen , Germany.
  • 7. Department of Bioresources , Fraunhofer Institute for Molecular Biology and Applied Ecology , 35392 Giessen , Germany.
  • 8. Department of Anatomy, Faculty of Science , Mahidol University , Ratchathewi, Bangkok 10400 , Thailand.
PMID: 32040314 DOI: 10.1021/acs.jnatprod.9b00886
Abstract

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.