Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada

doi:10.1016/j.phytochem.2017.01.007

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	Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada
	Yu, Xiao-Qing 1; Jiang, Chang-Sheng 1; Zhang, Yi 1; Sun, Pan 1; Kurtan, Tibor 2; Mandi, Attila 2; Li, Xiao-Lu 3; Yao, Li-Gong 3; Liu, Ai-Hong 4; Wang, Bin 1
刊名	PHYTOCHEMISTRY
	2017-04
卷号	136 页码:81-93
关键词	Laurencia composita Rhodomelaceae Rearranged chamigrane sesquiterpenoid Chamigrane sesquiterpenoid Compositacins A-K ECD calculation X-ray diffraction Antifungal activity Cytotoxicity
ISSN号	0031-9422
DOI	10.1016/j.phytochem.2017.01.007
文献子类	Article
英文摘要	Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A-K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C-L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC80 value of 4 mu g/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC50 values ranging from 48.6 to 85.2 mu M. (C) 2017 Elsevier Ltd. All rights reserved.
资助项目	National Natural Science Foundation of China[81001397] ; National Natural Science Foundation of China[21162016] ; National Natural Science Foundation of China[21362024] ; Young Scientists Training Program of Jiangxi Province[20133BCB23004] ; Natural Science Foundation of Jiangxi Province, China[20151BAB205082] ; Natural Science Foundation of Jiangxi Province, China[20161BAB205211] ; State Key Laboratory of Drug Research-SIMM[SIMM1601KF-10] ; EU[00000000] ; European Regional Development Fund[GINOP-2.3.2-15-2016-00008]
WOS关键词	MARINE NATURAL-PRODUCTS ; ABSOLUTE-CONFIGURATION ; CHEMICAL-CONSTITUENTS ; DIGESTIVE GLAND ; SESQUITERPENES ; METABOLITES ; STEREOCHEMISTRY ; DERIVATIVES ; PACIFENOL ; ALKALOIDS
WOS研究方向	Biochemistry & Molecular Biology ; Plant Sciences
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000397354700010
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/272729]
专题	天然药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Mao, Shui-Chun
作者单位	1.Nanchang Univ, Sch Pharm, 461 Bayi Rd, Nanchang 330006, Jiangxi, Peoples R China; 2.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary; 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 4.Nanchang Univ, Ctr Anal & Testing, Nanchang 330047, Jiangxi, Peoples R China
推荐引用方式 GB/T 7714	Yu, Xiao-Qing,Jiang, Chang-Sheng,Zhang, Yi,et al. Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada[J]. PHYTOCHEMISTRY,2017,136:81-93.
APA	Yu, Xiao-Qing.,Jiang, Chang-Sheng.,Zhang, Yi.,Sun, Pan.,Kurtan, Tibor.,...&Mao, Shui-Chun.(2017).Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada.PHYTOCHEMISTRY,136,81-93.
MLA	Yu, Xiao-Qing,et al."Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada".PHYTOCHEMISTRY 136(2017):81-93.