Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>

Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>

Three new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from <i>Briareum violaceum</i>, a gorgonian inhabiting Taiwan...

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Main Authors: Atallah F. Ahmed, Yang Cheng, Chang-Feng Dai, Jyh-Horng Sheu
Format: Article
Language:English
Published: MDPI AG 2021-05-01
Series:Molecules
Subjects:
<i>Briareum violaceum</i>
klysimplexane
briarol
eunicellin
gorgonian
Online Access:https://www.mdpi.com/1420-3049/26/11/3276
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spelling doaj-7a9c3c36fd4541eaa60855c99c8bb6492021-06-01T01:32:44ZengMDPI AGMolecules1420-30492021-05-01263276327610.3390/molecules26113276Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>Atallah F. Ahmed0Yang Cheng1Chang-Feng Dai2Jyh-Horng Sheu3Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanInstitute of Oceanography, National Taiwan University, Taipei 112, TaiwanDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanThree new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from <i>Briareum violaceum</i>, a gorgonian inhabiting Taiwanese waters. The chemical structures of these compounds were determined by employing extensive analyses of NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. Metabolites 1‒3 were found to possess the rarely found skeleton of the diterpenoid klysimplexin T. All isolated compounds showed very weak cytotoxic activity against the growth of three cancer cell lines. A plausible biosynthetic pathway for briarols A‒C from the coexisting eunicellin diterpenoid briarol D (4) was postulated.https://www.mdpi.com/1420-3049/26/11/3276<i>Briareum violaceum</i>klysimplexanebriaroleunicellingorgonian
collection DOAJ
language English
format Article
sources DOAJ
author Atallah F. Ahmed
Yang Cheng
Chang-Feng Dai
Jyh-Horng Sheu
spellingShingle Atallah F. Ahmed
Yang Cheng
Chang-Feng Dai
Jyh-Horng Sheu
Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
Molecules
<i>Briareum violaceum</i>
klysimplexane
briarol
eunicellin
gorgonian
author_facet Atallah F. Ahmed
Yang Cheng
Chang-Feng Dai
Jyh-Horng Sheu
author_sort Atallah F. Ahmed
title Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
title_short Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
title_full Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
title_fullStr Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
title_full_unstemmed Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian <i>Briareum violaceum</i>
title_sort polyoxygenated klysimplexane- and eunicellin-based diterpenoids from the gorgonian <i>briareum violaceum</i>
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2021-05-01
description Three new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from <i>Briareum violaceum</i>, a gorgonian inhabiting Taiwanese waters. The chemical structures of these compounds were determined by employing extensive analyses of NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. Metabolites 1‒3 were found to possess the rarely found skeleton of the diterpenoid klysimplexin T. All isolated compounds showed very weak cytotoxic activity against the growth of three cancer cell lines. A plausible biosynthetic pathway for briarols A‒C from the coexisting eunicellin diterpenoid briarol D (4) was postulated.
topic <i>Briareum violaceum</i>
klysimplexane
briarol
eunicellin
gorgonian
url https://www.mdpi.com/1420-3049/26/11/3276
work_keys_str_mv AT atallahfahmed polyoxygenatedklysimplexaneandeunicellinbasedditerpenoidsfromthegorgonianibriareumviolaceumi
AT yangcheng polyoxygenatedklysimplexaneandeunicellinbasedditerpenoidsfromthegorgonianibriareumviolaceumi
AT changfengdai polyoxygenatedklysimplexaneandeunicellinbasedditerpenoidsfromthegorgonianibriareumviolaceumi
AT jyhhorngsheu polyoxygenatedklysimplexaneandeunicellinbasedditerpenoidsfromthegorgonianibriareumviolaceumi
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