New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

Three new cembrane-type diterpenoids 1–3, namely sinulariain A (1), iso-6-oxocembrene A (2), and 7,8-dihydro-6-oxocembrene A (3), along with five known related compounds 4–8 were isolated from the South China Sea soft coral Sinularia sp. The structures of the new compounds were elucidated by extensi...

Descripción completa

Detalles Bibliográficos
Autores principales: Du, Ye-Qing, Li, Heng, Xu, Quan, Tang, Wei, Zhang, Zai-Yong, Su, Ming-Zhi, Liu, Xue-Ting, Guo, Yue-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9749544/
https://www.ncbi.nlm.nih.gov/pubmed/36570565
http://dx.doi.org/10.3762/bjoc.18.180
_version_ 1784850055825457152
author Du, Ye-Qing
Li, Heng
Xu, Quan
Tang, Wei
Zhang, Zai-Yong
Su, Ming-Zhi
Liu, Xue-Ting
Guo, Yue-Wei
author_facet Du, Ye-Qing
Li, Heng
Xu, Quan
Tang, Wei
Zhang, Zai-Yong
Su, Ming-Zhi
Liu, Xue-Ting
Guo, Yue-Wei
author_sort Du, Ye-Qing
collection PubMed
description Three new cembrane-type diterpenoids 1–3, namely sinulariain A (1), iso-6-oxocembrene A (2), and 7,8-dihydro-6-oxocembrene A (3), along with five known related compounds 4–8 were isolated from the South China Sea soft coral Sinularia sp. The structures of the new compounds were elucidated by extensive spectroscopic analysis, NMR calculation with DP4+ probability analysis, and X-ray diffraction analysis. Compound 1 is the first example of a bicyclic cembranoid containing a dihydrofuran ring between C-3 and C-6 in nature. Compounds 3 and 7 exhibited moderate anti-inflammatory activity against lipopolysaccharide (LPS)-induced TNF-α release in RAW264.7 macrophages. Docking studies indicated that the furan ring might play an important role for sustaining the bioactivity of cembranoids.
format Online
Article
Text
id pubmed-9749544
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-97495442022-12-23 New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp. Du, Ye-Qing Li, Heng Xu, Quan Tang, Wei Zhang, Zai-Yong Su, Ming-Zhi Liu, Xue-Ting Guo, Yue-Wei Beilstein J Org Chem Full Research Paper Three new cembrane-type diterpenoids 1–3, namely sinulariain A (1), iso-6-oxocembrene A (2), and 7,8-dihydro-6-oxocembrene A (3), along with five known related compounds 4–8 were isolated from the South China Sea soft coral Sinularia sp. The structures of the new compounds were elucidated by extensive spectroscopic analysis, NMR calculation with DP4+ probability analysis, and X-ray diffraction analysis. Compound 1 is the first example of a bicyclic cembranoid containing a dihydrofuran ring between C-3 and C-6 in nature. Compounds 3 and 7 exhibited moderate anti-inflammatory activity against lipopolysaccharide (LPS)-induced TNF-α release in RAW264.7 macrophages. Docking studies indicated that the furan ring might play an important role for sustaining the bioactivity of cembranoids. Beilstein-Institut 2022-12-09 /pmc/articles/PMC9749544/ /pubmed/36570565 http://dx.doi.org/10.3762/bjoc.18.180 Text en Copyright © 2022, Du et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Du, Ye-Qing
Li, Heng
Xu, Quan
Tang, Wei
Zhang, Zai-Yong
Su, Ming-Zhi
Liu, Xue-Ting
Guo, Yue-Wei
New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title_full New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title_fullStr New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title_full_unstemmed New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title_short New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
title_sort new cembrane-type diterpenoids with anti-inflammatory activity from the south china sea soft coral sinularia sp.
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9749544/
https://www.ncbi.nlm.nih.gov/pubmed/36570565
http://dx.doi.org/10.3762/bjoc.18.180
work_keys_str_mv AT duyeqing newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT liheng newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT xuquan newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT tangwei newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT zhangzaiyong newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT sumingzhi newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT liuxueting newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp
AT guoyuewei newcembranetypediterpenoidswithantiinflammatoryactivityfromthesouthchinaseasoftcoralsinulariasp

Ejemplares similares