Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants
Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants
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DOI：
10.1023/b:joec.0000017975.16399.c3
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发表时间：
2004-02-01
影响因子：
2.3
通讯作者：
Bernays, EA
中科院分区：
文献类型：
--
作者：
Hartmann, T;Theuring, C;Bernays, EA
编制了亚利桑那州东南部两种高度多食性的绿头虫Estimene acrea和Gramia genura中的吡咯里西丁生物碱(PAS)的分布及其潜在的PA来源。紫草科四种植物中的一种，Plagiobothys arizonicus，含有多胺；这是该植物的第一个PA记录。PA的主要来源是菊科千里光(Senecio Longilobus)和豆科豆科植物Crotalaria puila。扩展了已知的长柄链霉菌的PA模式；该种被发现含有六个与千里光碱型密切相关的PA。从前人未见研究过的短冠草属植物中分离并鉴定了三个新的野百合碱型多胺类化合物，命名为短冠草素A-C。小豆碱是种子中的主要多胺，而在营养器官中，它们伴随着简单的甜蜜素衍生物苏豆碱，并作为优势化合物亚乌拉辛(1β，2β-环氧三苯二甲双胺)。在这两种植物中，Pas都以N-氧化物的形式储存，但短小金鸡儿种子积累了游离碱。不同种群间PA组成存在较大差异。建立了摄食人工饲料添加角鱼粉的金龟子幼虫和成虫的PA图谱，并对取食长尾轮虫的遗传小蜂进行了分析。在这两个实验中，幼虫可以在各自的PA来源和饮食之间自由选择，或者在不含PA的食物植物中自由选择。为这两个物种编制的图谱反映了它们的PA来源的生物碱图谱，但有一个例外，即在龙须草中永远不能检测到亚乌拉辛。除获得性多胺外，在这两个北极种中还检测到由获得性蜜碱和昆虫来源的蜜酸合成的昆虫多胺。这些不存在于幼虫食物来源的昆虫多酚类物质约占从昆虫中提取的多酚类物质总量的40-70%(E.acrea)和17-37%(G.genura)。鉴定出了许多新的昆虫PA。植物和昆虫获取的苯丙氨酸被发现以N-氧化物的形式积累。结果被讨论了与特定的生化、电生理和行为机制有关的PA固存涉及牛膝糖。
The profiles of pyrrolizidine alkaloids (PAs) in the two highly polyphagous arctiids Estigmene acrea and Grammia geneura and their potential PA sources in southeastern Arizona were compiled. One of four species of Boraginaceae, Plagiobothrys arizonicus, contained PAs; this is the first PA record for this plant species. The principle PA sources are Senecio longilobus (Asteraceae) and Crotalaria pumila (Fabaceae). The known PA pattern of S. longilobus was extended; the species was found to contain six closely related PAs of the senecionine type. Three novel PAs of the monocrotaline type, named pumilines A-C, were isolated and characterized from C. pumila, a species not studied before. The pumilines are the major PAs in the seeds, while in the vegetative organs they are accompanied by the simple necine derivatives supinidine and as the dominant compound subulacine (1beta,2beta-epoxytrachelanthamidine). In both plant species, the PAs are stored as N-oxides, except C. pumila seeds, which accumulate the free bases. Great variation in PA composition was observed between local populations of C. pumila. The PA profiles were established for larvae and adults of E. acrea that as larvae had fed on an artificial diet supplemented with crotalaria-powder and of G. geneura fed with S. longilobus. In both experiments, the larvae had a free choice between the respective PA source and diet or food plants free of PAs. The profiles compiled for the two species reflect the alkaloid profiles of their PA sources with one exception, subulacine could never be detected in E. acrea. Besides acquired PAs, insect PAs synthesized from acquired necine bases and necic acids of insect origin were detected in the two arctiid species. These insect PAs that do not occur in the larval food sources accounted for some 40-70% (E. acrea) and 17-37% (G. geneura) of total PAs extracted from the insects. A number of novel insect PAs were identified. Plant-acquired and insect PAs were found to accumulate as N-oxides. The results are discussed in relation to specific biochemical, electrophysiological, and behavioral mechanisms involved in PA sequestration by arctiids.