Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity

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	Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity
	Duan, Xiao-Juan ; Li, Xiao-Ming ; Wang, Bin-Gui; Wang, BG, Chinese Acad Sci, Inst Oceanog, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China
	2007-07-01
发表期刊	JOURNAL OF NATURAL PRODUCTS
ISSN	0163-3864
卷号	70 期号:7 页码:1210-1213
文章类型	Article
摘要	Four new highly brominated and fully substituted mono- and bis-phenols, 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (1), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane (2), 6-(2,3,6-tribromo-4,5-dihydroxybenzyl)-2,5-dibromo-3,4-dihydroxybenzyl methyl ether (3), and 2,3,6-tribromo-4,5-dihydroxybenzyl methyl sulfone (4), were characterized from the marine red alga Symphyocladia latiuscula. In addition, five known bromophenols, bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (5), bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether (6), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (7), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (8), and 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (9), were also isolated and identified. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR as well as by low- and high-resolution mass spectrometric analysis. Structurally, all of these compounds are highly brominated and fully substituted, and contain one or two 2,3,6-tribromo-4,5-dihydroxyphenyl unit(s) in each of the molecules. In addition, compound 4 possesses a unique sulfone structural feature. Each of the isolated compounds was evaluated for alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity and all were found to be potent, with IC50 values ranging from 8.1 to 24.7 mu M, compared to the known positive control butylated hydroxytoluene (BHT), with an IC50 of 81.8 mu M.; Four new highly brominated and fully substituted mono- and bis-phenols, 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (1), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane (2), 6-(2,3,6-tribromo-4,5-dihydroxybenzyl)-2,5-dibromo-3,4-dihydroxybenzyl methyl ether (3), and 2,3,6-tribromo-4,5-dihydroxybenzyl methyl sulfone (4), were characterized from the marine red alga Symphyocladia latiuscula. In addition, five known bromophenols, bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (5), bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether (6), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (7), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (8), and 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (9), were also isolated and identified. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR as well as by low- and high-resolution mass spectrometric analysis. Structurally, all of these compounds are highly brominated and fully substituted, and contain one or two 2,3,6-tribromo-4,5-dihydroxyphenyl unit(s) in each of the molecules. In addition, compound 4 possesses a unique sulfone structural feature. Each of the isolated compounds was evaluated for alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity and all were found to be potent, with IC50 values ranging from 8.1 to 24.7 mu M, compared to the known positive control butylated hydroxytoluene (BHT), with an IC50 of 81.8 mu M.
关键词	Rhodomela-confervoides Bromophenol Constituents Derivatives Ether
学科领域	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000248344800027
引用统计	被引频次：117[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/1595
专题	实验海洋生物学重点实验室
通讯作者	Wang, BG, Chinese Acad Sci, Inst Oceanog, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China
作者单位	1.Chinese Acad Sci, Inst Oceanog, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
推荐引用方式 GB/T 7714	Duan, Xiao-Juan,Li, Xiao-Ming,Wang, Bin-Gui,et al. Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity[J]. JOURNAL OF NATURAL PRODUCTS,2007,70(7):1210-1213.
APA	Duan, Xiao-Juan,Li, Xiao-Ming,Wang, Bin-Gui,&Wang, BG, Chinese Acad Sci, Inst Oceanog, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China.(2007).Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity.JOURNAL OF NATURAL PRODUCTS,70(7),1210-1213.
MLA	Duan, Xiao-Juan,et al."Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity".JOURNAL OF NATURAL PRODUCTS 70.7(2007):1210-1213.

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