2. Academic Validation
  3. Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper

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

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.

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