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Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis

Documents on the chemical composition of the soft coral Sarcophyton mililatensis are sparse. The present investigation of the Hainan soft coral S. mililatensis resulted in the discovery of six new cembrane diterpenes, sarcoxacyclols A–F (1–6) and four known analogs (7–10). Their structures were eluc...

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Autores principales: Zhang, Ling, Yang, Min, Chen, Zi-Hui, Ge, Zeng-Yue, Li, Song-Wei, Yan, Xian-Yun, Yao, Li-Gong, Liang, Lin-Fu, Guo, Yue-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9915928/
https://www.ncbi.nlm.nih.gov/pubmed/36768306
http://dx.doi.org/10.3390/ijms24031979
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author Zhang, Ling
Yang, Min
Chen, Zi-Hui
Ge, Zeng-Yue
Li, Song-Wei
Yan, Xian-Yun
Yao, Li-Gong
Liang, Lin-Fu
Guo, Yue-Wei
author_facet Zhang, Ling
Yang, Min
Chen, Zi-Hui
Ge, Zeng-Yue
Li, Song-Wei
Yan, Xian-Yun
Yao, Li-Gong
Liang, Lin-Fu
Guo, Yue-Wei
author_sort Zhang, Ling
collection PubMed
description Documents on the chemical composition of the soft coral Sarcophyton mililatensis are sparse. The present investigation of the Hainan soft coral S. mililatensis resulted in the discovery of six new cembrane diterpenes, sarcoxacyclols A–F (1–6) and four known analogs (7–10). Their structures were elucidated by extensive spectroscopic analysis along with a comparison with the data in current literature. The nonaromatic oxacycles in their structures were the rarely found tetrahydrofuran ether across C-1 and C-12 and tetrahydropyran ether across C-1 and C-11, respectively. Moreover, the absolute configuration of compound 4 was established unambiguously by X-ray diffraction analysis using Ga Kα radiation (λ = 1.34139 Å). Based on the biogenetical consideration, the absolute configurations of other five new compounds were tentatively assumed. Assessment of the bioactivity for these secondary metabolites revealed that compound 1 exhibited significant tumor necrosis factor (TNF)-α inhibitory activity (IC(50) = 9.5 μmol/L), similar to the positive control dexamethasone (IC(50) = 8.7 μmol/L), but no obvious cytotoxicity towards RAW264.7 cells (CC(50) > 50 μmol/L). The preliminary molecular docking suggested the crucial roles of the hydroxyl and acetoxyl groups in the computational prediction of the binding mode between the diterpene and the protein.
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spelling pubmed-99159282023-02-11 Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis Zhang, Ling Yang, Min Chen, Zi-Hui Ge, Zeng-Yue Li, Song-Wei Yan, Xian-Yun Yao, Li-Gong Liang, Lin-Fu Guo, Yue-Wei Int J Mol Sci Article Documents on the chemical composition of the soft coral Sarcophyton mililatensis are sparse. The present investigation of the Hainan soft coral S. mililatensis resulted in the discovery of six new cembrane diterpenes, sarcoxacyclols A–F (1–6) and four known analogs (7–10). Their structures were elucidated by extensive spectroscopic analysis along with a comparison with the data in current literature. The nonaromatic oxacycles in their structures were the rarely found tetrahydrofuran ether across C-1 and C-12 and tetrahydropyran ether across C-1 and C-11, respectively. Moreover, the absolute configuration of compound 4 was established unambiguously by X-ray diffraction analysis using Ga Kα radiation (λ = 1.34139 Å). Based on the biogenetical consideration, the absolute configurations of other five new compounds were tentatively assumed. Assessment of the bioactivity for these secondary metabolites revealed that compound 1 exhibited significant tumor necrosis factor (TNF)-α inhibitory activity (IC(50) = 9.5 μmol/L), similar to the positive control dexamethasone (IC(50) = 8.7 μmol/L), but no obvious cytotoxicity towards RAW264.7 cells (CC(50) > 50 μmol/L). The preliminary molecular docking suggested the crucial roles of the hydroxyl and acetoxyl groups in the computational prediction of the binding mode between the diterpene and the protein. MDPI 2023-01-19 /pmc/articles/PMC9915928/ /pubmed/36768306 http://dx.doi.org/10.3390/ijms24031979 Text en © 2023 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
Zhang, Ling
Yang, Min
Chen, Zi-Hui
Ge, Zeng-Yue
Li, Song-Wei
Yan, Xian-Yun
Yao, Li-Gong
Liang, Lin-Fu
Guo, Yue-Wei
Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title_full Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title_fullStr Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title_full_unstemmed Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title_short Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral Sarcophyton mililatensis
title_sort cembrane diterpenes possessing nonaromatic oxacycles from the hainan soft coral sarcophyton mililatensis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9915928/
https://www.ncbi.nlm.nih.gov/pubmed/36768306
http://dx.doi.org/10.3390/ijms24031979
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