Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum

Abstract The four new briarane diterpenoids 2-butyryloxybriarane B-3 (2), 9-acetylbriarenolide S (3), briarenolide W (4), and 12-isobriarenolide P (5), along with briarane B-3 (1) and the five known diterpenes 6–10 were isolated from the gorgonian coral Briareum asbestinum collected from the Mexican...

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Autores principales:	Dawrin Pech-Puch, Pedro Joseph-Nathan, Eleuterio Burgueño-Tapia, Carlos González-Salas, Diana Martínez-Matamoros, David M. Pereira, Renato B. Pereira, Carlos Jiménez, Jaime Rodríguez
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/78f116e0c21947f59551bf9400e5f299
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spelling	oai:doaj.org-article:78f116e0c21947f59551bf9400e5f2992021-12-02T14:12:41ZAbsolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum10.1038/s41598-020-79774-12045-2322https://doaj.org/article/78f116e0c21947f59551bf9400e5f2992021-01-01T00:00:00Zhttps://doi.org/10.1038/s41598-020-79774-1https://doaj.org/toc/2045-2322Abstract The four new briarane diterpenoids 2-butyryloxybriarane B-3 (2), 9-acetylbriarenolide S (3), briarenolide W (4), and 12-isobriarenolide P (5), along with briarane B-3 (1) and the five known diterpenes 6–10 were isolated from the gorgonian coral Briareum asbestinum collected from the Mexican Caribbean Sea. The structures were elucidated by 1D and 2D NMR and MS measurements. Since the structure of briarane B-3 (1) was only suggested and published without any spectroscopic support, it was herein confirmed, and the supporting data are now provided. In addition, 1 provided the opportunity to explore the sensitivity of vibrational circular dichroism (VCD) to determine the configuration of a single stereogenic center in the presence of eight other stereogenic centers in a molecule possessing a highly flexible ten-member ring. A single-crystal X-ray diffraction study, in which the Flack and Hooft parameters of 1 were determined, further confirmed that briarane B-3 is (1S,2S,6S,7R,8R,9S,10S,11R,17R)-1. This paper reports for first time the use of VCD in briarane diterpenes and with the presence of chlorine atoms. Biological evaluation of seven isolated compounds evidenced a moderate anti-inflammatory activity for compounds 6 and 9 but it did not show any cytotoxic, antiviral, antibacterial, and topoisomerase inhibitory activity.Dawrin Pech-PuchPedro Joseph-NathanEleuterio Burgueño-TapiaCarlos González-SalasDiana Martínez-MatamorosDavid M. PereiraRenato B. PereiraCarlos JiménezJaime RodríguezNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-14 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Dawrin Pech-Puch Pedro Joseph-Nathan Eleuterio Burgueño-Tapia Carlos González-Salas Diana Martínez-Matamoros David M. Pereira Renato B. Pereira Carlos Jiménez Jaime Rodríguez Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
description	Abstract The four new briarane diterpenoids 2-butyryloxybriarane B-3 (2), 9-acetylbriarenolide S (3), briarenolide W (4), and 12-isobriarenolide P (5), along with briarane B-3 (1) and the five known diterpenes 6–10 were isolated from the gorgonian coral Briareum asbestinum collected from the Mexican Caribbean Sea. The structures were elucidated by 1D and 2D NMR and MS measurements. Since the structure of briarane B-3 (1) was only suggested and published without any spectroscopic support, it was herein confirmed, and the supporting data are now provided. In addition, 1 provided the opportunity to explore the sensitivity of vibrational circular dichroism (VCD) to determine the configuration of a single stereogenic center in the presence of eight other stereogenic centers in a molecule possessing a highly flexible ten-member ring. A single-crystal X-ray diffraction study, in which the Flack and Hooft parameters of 1 were determined, further confirmed that briarane B-3 is (1S,2S,6S,7R,8R,9S,10S,11R,17R)-1. This paper reports for first time the use of VCD in briarane diterpenes and with the presence of chlorine atoms. Biological evaluation of seven isolated compounds evidenced a moderate anti-inflammatory activity for compounds 6 and 9 but it did not show any cytotoxic, antiviral, antibacterial, and topoisomerase inhibitory activity.
format	article
author	Dawrin Pech-Puch Pedro Joseph-Nathan Eleuterio Burgueño-Tapia Carlos González-Salas Diana Martínez-Matamoros David M. Pereira Renato B. Pereira Carlos Jiménez Jaime Rodríguez
author_facet	Dawrin Pech-Puch Pedro Joseph-Nathan Eleuterio Burgueño-Tapia Carlos González-Salas Diana Martínez-Matamoros David M. Pereira Renato B. Pereira Carlos Jiménez Jaime Rodríguez
author_sort	Dawrin Pech-Puch
title	Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
title_short	Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
title_full	Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
title_fullStr	Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
title_full_unstemmed	Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum
title_sort	absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the gorgonian briareum asbestinum
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/78f116e0c21947f59551bf9400e5f299
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Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum

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