An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods

被引：21

作者：

Areche, Carlos ^{[1
]}

San-Martin, Aurelio ^{[1
]}

Rovirosa, Juana ^{[1
]}

Soto-Delgado, Jorge ^{[1
]}

Contreras, Renato ^{[1
]}

机构：

[1] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

来源：

PHYTOCHEMISTRY | 2009年 / 70卷 / 10期

关键词：

Stypopodium flabelliforme; Dictyotaceae; Seaweeds; Meroditerpenoids; GIAO/DFT; Stypotriol; MARINE NATURAL-PRODUCTS; BROWN-ALGA; CHEMICAL ECOLOGY; ZONALE; EPITAONDIOL; DICTYOTALES; PHAEOPHYTA; MOLECULES; DENSITY;

D O I：

10.1016/j.phytochem.2009.07.017

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

Meroditerpenoids, 2-[2'(E)-3',7',11',15'-tetramethylhexadec-2-en-1'-yl]-6-methyl-1,4-benzohydroquinone diacetate and 4'-chlorostypotriol triacetate, along with eight known compounds isolated from the dichloromethane extract of the brown alga Stypopodium flabelliforme after peracetylation are reported. One of them, 2-(1-oxo-hexadecyl)-1,3,5-trihydroxybenzene, is described for the first time within this genus. Structural elucidation was carried out on the basis of spectroscopic data and theoretical studies using GIAO/DFT analysis at B3LYP/6-31G(d) and mPW1PW91/6-31G(d) levels of theory for 4'-chlorostypotriol. This isomer is the first metabolite from the Stypopodium genus possessing one halogen atom. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1315 / 1320

页数：6

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