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Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea

Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3–6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The abso...

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Autores principales: Zheng, Juan-Juan, Shao, Chang-Lun, Chen, Min, Gan, Li-She, Fang, Yu-Chun, Wang, Xu-Hui, Wang, Chang-Yun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3967227/
https://www.ncbi.nlm.nih.gov/pubmed/24637960
http://dx.doi.org/10.3390/md12031569
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author Zheng, Juan-Juan
Shao, Chang-Lun
Chen, Min
Gan, Li-She
Fang, Yu-Chun
Wang, Xu-Hui
Wang, Chang-Yun
author_facet Zheng, Juan-Juan
Shao, Chang-Lun
Chen, Min
Gan, Li-She
Fang, Yu-Chun
Wang, Xu-Hui
Wang, Chang-Yun
author_sort Zheng, Juan-Juan
collection PubMed
description Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3–6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C(16) skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio.
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spelling pubmed-39672272014-03-27 Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea Zheng, Juan-Juan Shao, Chang-Lun Chen, Min Gan, Li-She Fang, Yu-Chun Wang, Xu-Hui Wang, Chang-Yun Mar Drugs Communication Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3–6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C(16) skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio. MDPI 2014-03-14 /pmc/articles/PMC3967227/ /pubmed/24637960 http://dx.doi.org/10.3390/md12031569 Text en © 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Zheng, Juan-Juan
Shao, Chang-Lun
Chen, Min
Gan, Li-She
Fang, Yu-Chun
Wang, Xu-Hui
Wang, Chang-Yun
Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title_full Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title_fullStr Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title_full_unstemmed Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title_short Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea
title_sort ochracenoids a and b, guaiazulene-based analogues from gorgonian anthogorgia ochracea collected from the south china sea
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3967227/
https://www.ncbi.nlm.nih.gov/pubmed/24637960
http://dx.doi.org/10.3390/md12031569
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