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

Apisada Jiso; Siriporn Kittiwisut; Ruttanaporn Chantakul; Supreeya Yuenyongsawad; Sumaitt Putchakarn; Till F. Schäberle; Prapapan Temkitthaworn; Kornkanok Ingkaninan; Kulathida Chaithirayanon; Anuchit Plubrukarn

doi:10.1021/acs.jnatprod.9b00886

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

Apisada Jiso
, Siriporn Kittiwisut
, Ruttanaporn Chantakul
, Supreeya Yuenyongsawad
, Sumaitt Putchakarn
, Till F. Schäberle
, Prapapan Temkitthaworn
, Kornkanok Ingkaninan
, Kulathida Chaithirayanon
, Anuchit Plubrukarn

Prince of Songkla University
Thammasat University
Naresuan University
Walailak University
Burapha University
Justus-Liebig-University Gießen
Fraunhofer Institute for Molecular Biology and Applied Ecology (IME)
Mahidol University

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	532-536
Number of pages	5
Journal	Journal of Natural Products
Volume	83
Issue number	2
DOIs	https://doi.org/10.1021/acs.jnatprod.9b00886
Publication status	Published - 28 Feb 2020
Externally published	Yes

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10.1021/acs.jnatprod.9b00886

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

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.",

author = "Apisada Jiso and Siriporn Kittiwisut and Ruttanaporn Chantakul and Supreeya Yuenyongsawad and Sumaitt Putchakarn and Sch{\"a}berle, \{Till F.\} and Prapapan Temkitthaworn and Kornkanok Ingkaninan and Kulathida Chaithirayanon and Anuchit Plubrukarn",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society and American Society of Pharmacognosy.",

year = "2020",

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doi = "10.1021/acs.jnatprod.9b00886",

language = "English",

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pages = "532--536",

journal = "Journal of Natural Products",

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T1 - Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper

AU - Jiso, Apisada

AU - Kittiwisut, Siriporn

AU - Chantakul, Ruttanaporn

AU - Yuenyongsawad, Supreeya

AU - Putchakarn, Sumaitt

AU - Schäberle, Till F.

AU - Temkitthaworn, Prapapan

AU - Ingkaninan, Kornkanok

AU - Chaithirayanon, Kulathida

AU - Plubrukarn, Anuchit

PY - 2020/2/28

Y1 - 2020/2/28

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85079751529

U2 - 10.1021/acs.jnatprod.9b00886

DO - 10.1021/acs.jnatprod.9b00886

M3 - Article

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EP - 536

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 2

ER -

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

Abstract

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