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Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta

Chemical investigation of the Hainan soft coral Sinularia hirta resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A (7), six new xeniaphyllane-type...

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Autores principales: Chen, Zi-Hui, Lu, Si-Qi, Han, Guan-Ying, Li, Xu-Wen, Guo, Yue-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9030993/
https://www.ncbi.nlm.nih.gov/pubmed/35447945
http://dx.doi.org/10.3390/md20040272
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author Chen, Zi-Hui
Lu, Si-Qi
Han, Guan-Ying
Li, Xu-Wen
Guo, Yue-Wei
author_facet Chen, Zi-Hui
Lu, Si-Qi
Han, Guan-Ying
Li, Xu-Wen
Guo, Yue-Wei
author_sort Chen, Zi-Hui
collection PubMed
description Chemical investigation of the Hainan soft coral Sinularia hirta resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A (7), six new xeniaphyllane-type diterpenoids (1–6), one new norxeniaphyllanoid (8), two new norcaryophyllene-type sesquiterpenoids (9 and 10), together with six known related compounds (11–16). Compounds 1–3 are three new furanone-containing xeniaphyllane-type diterpenoids. The structures of the new compounds, including their absolute configurations, were determined by extensive spectroscopic analysis and a series of quantum chemical calculations, including quantum mechanical-nuclear magnetic resonance (QM–NMR), time-dependent density functional theory–electronic circular dichroism (TDDFT–ECD), and optical rotatory dispersion (ORD) methods. A plausible biosynthetic connection between new compounds 1–9 was also proposed. New compounds 2–4, 7, and 8 were evaluated for in vitro cytotoxicity against four cancer cell lines.
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spelling pubmed-90309932022-04-23 Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta Chen, Zi-Hui Lu, Si-Qi Han, Guan-Ying Li, Xu-Wen Guo, Yue-Wei Mar Drugs Article Chemical investigation of the Hainan soft coral Sinularia hirta resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A (7), six new xeniaphyllane-type diterpenoids (1–6), one new norxeniaphyllanoid (8), two new norcaryophyllene-type sesquiterpenoids (9 and 10), together with six known related compounds (11–16). Compounds 1–3 are three new furanone-containing xeniaphyllane-type diterpenoids. The structures of the new compounds, including their absolute configurations, were determined by extensive spectroscopic analysis and a series of quantum chemical calculations, including quantum mechanical-nuclear magnetic resonance (QM–NMR), time-dependent density functional theory–electronic circular dichroism (TDDFT–ECD), and optical rotatory dispersion (ORD) methods. A plausible biosynthetic connection between new compounds 1–9 was also proposed. New compounds 2–4, 7, and 8 were evaluated for in vitro cytotoxicity against four cancer cell lines. MDPI 2022-04-18 /pmc/articles/PMC9030993/ /pubmed/35447945 http://dx.doi.org/10.3390/md20040272 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chen, Zi-Hui
Lu, Si-Qi
Han, Guan-Ying
Li, Xu-Wen
Guo, Yue-Wei
Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title_full Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title_fullStr Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title_full_unstemmed Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title_short Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta
title_sort sinuhirtone a, an uncommon 17,19-dinorxeniaphyllanoid, and nine related new terpenoids from the hainan soft coral sinularia hirta
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9030993/
https://www.ncbi.nlm.nih.gov/pubmed/35447945
http://dx.doi.org/10.3390/md20040272
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