Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: Potential for broomrapes and field dodder management
Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: Potential for broomrapes and field dodder management
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DOI：
10.1016/j.phytochem.2012.10.003
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发表时间：
2013-02-01
期刊：
影响因子：
3.8
通讯作者：
Evidente, Antonio
中科院分区：
文献类型：
--
作者：
Andolfi, Anna;Zermane, Nadjia;Evidente, Antonio
从地中海地区广布的菊科植物粘旋覆花（Inula viscosa）的地上部分中分离出4种具有植物毒性的双环和三环倍半萜内酯，命名为菊氧素A-D，并与已知的α-木香酸一起被鉴定。通过光谱和化学方法确定了菊粉A-D的结构，并确定为：（4 E，7 R *，8 R *，10 S *）-3-氧代-香叶-4，11（13）-二烯-8 β-12-酮（A），其11，13-二氢类似物（B），（5 R *，7 R *，8 R *，10 R *）-1，15-亚甲基-5 β-羟基-桉叶素-1（15），11（13）-二烯-8 β-12-酮（C）和（7 R *，8 R *）-1，4-二甲基-4-羟基-桉叶素-5（10），11（13）-二烯-8 β-12-酮（D）。应用改进的Mosher方法，对菊粉D的5-羟基己-2-基侧链C-5位的S绝对立体化学进行了归属。评价了菊粉A-D、重氮和单乙酰基衍生物（菊粉A和C，resply）以及α-costic酸对两种寄生植物物种，即钝齿列当（Orobanche crenata）和田野菟丝子（Cuscuta campestris）的植物毒性活性。犬儒毒素A、C和D对这两种寄生虫的活性最高，对种子萌发的抑制率高达100%。菊粉B对菟丝子活性较低，对列当完全无活性。主要代谢产物α-哥斯达黎加酸对菟丝子种子萌发有抑制作用，对肉苁蓉种子萌发有促进作用。这些初步结果允许假设一些结构-活性关系。(c)2012爱思唯尔有限公司保留所有权利。
Four phytotoxic bi- and tri-cyclic sesquiterpene lactones, named inuloxins A-D, were isolated together with the known alpha-costic acid, from the aerial parts of Inula viscosa (family Asteraceae), a widespread Mediterranean plant well known for its content of pharmacologically active metabolites. The structures of inuloxins A-D were established by spectroscopic and chemical methods and determined to be: (4E,7R*,8R*,10S*)-3-oxo-germacra-4,11(13)-dien-8 beta-12-olide (A), its 11,13-dihydro analogue (B), (5R*,7R*,8R*,10R*)-1,15-methylene-5 beta-hydroxy-eudesm-1(15),11(13)-dien-8 beta-12-olide (C), and (7R*,8R*)-1,4-dimethyl-4-hydroxy-secoeudesm-5(10),11(13)-dien-8 beta-12-olide (D). The S absolute stereochemistry at C-5 of 5-hydroxyhexan-2-yl side chain of inuloxin D was assigned by applying an advanced Mosher's method. The phytotoxic activity of inuloxins A-D, that of the diazo and monoacetyl derivatives (of inuloxin A and C, resply), as well as that of alpha-costic acid was evaluated against two parasitic plant species, i.e. crenate broomrape (Orobanche crenata) and field dodder (Cuscuta campestris). Inuloxins A, C and D were the most active on both parasites and caused up to 100% inhibition of the seed germination. Inuloxin B was less active on Cuscuta and completely inactive against Orobanche. The main metabolite alpha-costic acid had a suppressive effect on the dodder seed germination but had a stimulating action on the broomrape seed germination. These preliminary results allowed to suppose some structure-activity relationships. (c) 2012 Elsevier Ltd. All rights reserved.