Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris

Abstract Three new guaiazulene alkaloids muriceidines A–C (1–3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt Δ 1-pipecolic...

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Autores principales:	Pinglin Li, Xiaoling Liu, Hongyan Zhu, Xuli Tang, Xuefeng Shi, Yonghong Liu, Guoqiang Li
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/f84d40a73f1b441fb0da7c2c3068b865
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spelling	oai:doaj.org-article:f84d40a73f1b441fb0da7c2c3068b8652021-12-02T11:53:11ZUnusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris10.1038/s41598-017-08100-z2045-2322https://doaj.org/article/f84d40a73f1b441fb0da7c2c3068b8652017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-08100-zhttps://doaj.org/toc/2045-2322Abstract Three new guaiazulene alkaloids muriceidines A–C (1–3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt Δ 1-pipecolic acid via a unique sp2 methine-bridged linkage, and the bis-sesquiterpene was comprised by a guaiazulene and a indene units linked through a unprecedented carbon-carbon σ-bond between the high steric bridgehead carbon C-10 of guaiazulene moiety and C-2′ of indene moiety. The chiral compounds 2–4 were obtained initially as racemates and further separated by chiral HPLC methods. The inner-salt structures of 1–3 and absolute configurations of 2–4 were fully elucidated by calculated 13C NMR, ECD and OR with quantum chemical calculation methods. Compound 1 showed cytotoxicity against K562 cell lines with IC50 value of 8.4 μM and antifouling activity against the larvae of the barnacle Balanus albicostatus with EC50 value of 11.9 μg/mL and potent therapeutic index (LC50/EC50 = 3.66). Also the racemic (±)-3 showed cytotoxicities against both HL-60 and K562 cell lines with IC50 values of 2.2 and 3.7 μM, respectively. A semisynthetic trial was performed to validate the proposed biosynthetic hypotheses.Pinglin LiXiaoling LiuHongyan ZhuXuli TangXuefeng ShiYonghong LiuGuoqiang LiNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Pinglin Li Xiaoling Liu Hongyan Zhu Xuli Tang Xuefeng Shi Yonghong Liu Guoqiang Li Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
description	Abstract Three new guaiazulene alkaloids muriceidines A–C (1–3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt Δ 1-pipecolic acid via a unique sp2 methine-bridged linkage, and the bis-sesquiterpene was comprised by a guaiazulene and a indene units linked through a unprecedented carbon-carbon σ-bond between the high steric bridgehead carbon C-10 of guaiazulene moiety and C-2′ of indene moiety. The chiral compounds 2–4 were obtained initially as racemates and further separated by chiral HPLC methods. The inner-salt structures of 1–3 and absolute configurations of 2–4 were fully elucidated by calculated 13C NMR, ECD and OR with quantum chemical calculation methods. Compound 1 showed cytotoxicity against K562 cell lines with IC50 value of 8.4 μM and antifouling activity against the larvae of the barnacle Balanus albicostatus with EC50 value of 11.9 μg/mL and potent therapeutic index (LC50/EC50 = 3.66). Also the racemic (±)-3 showed cytotoxicities against both HL-60 and K562 cell lines with IC50 values of 2.2 and 3.7 μM, respectively. A semisynthetic trial was performed to validate the proposed biosynthetic hypotheses.
format	article
author	Pinglin Li Xiaoling Liu Hongyan Zhu Xuli Tang Xuefeng Shi Yonghong Liu Guoqiang Li
author_facet	Pinglin Li Xiaoling Liu Hongyan Zhu Xuli Tang Xuefeng Shi Yonghong Liu Guoqiang Li
author_sort	Pinglin Li
title	Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
title_short	Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
title_full	Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
title_fullStr	Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
title_full_unstemmed	Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris
title_sort	unusual inner-salt guaiazulene alkaloids and bis-sesquiterpene from the south china sea gorgonian muriceides collaris
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/f84d40a73f1b441fb0da7c2c3068b865
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Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris

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