少花千里光的防御性化学物质

Defensive chemistry of Senecio miser.

作者信息

Reina M, González-Coloma A, Gutiérrez C, Cabrera R, Rodríguez M L, Fajardo V, Villarroel L

机构信息

Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, La Laguna, Tenerife, Spain.

出版信息

J Nat Prod. 2001 Jan;64(1):6-11. doi: 10.1021/np000114o.

DOI:10.1021/np000114o

PMID:11170657

Abstract

Three eremophilanolides, 1alpha-acetoxy-8beta-methoxy-10betaH-eremophil-7(11)-en-8alpha,12-olide (1); 1alpha-angeloyloxy-6beta-hydroxy-8beta-methoxy-10betaH-eremophil-7(11)-en-8alpha,12-olide (2); and 1alpha-angeloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide (3), and two pyrrolizidine alkaloids, integerrimine (4) and its N-oxide (5), were isolated from bioactive fractions of Senecio miser. The structures of the new compounds 1 and 2 were established by NMR spectroscopic analysis and chemical transformation. The X-ray analysis of compound 1 was also performed. Eremophilanolides 1 and 2 and alkaloids 4 and 5 were found to be strong insect antifeedants, further supporting a proposed defensive role for these classes of compounds.

摘要

从奇形千里光的生物活性组分中分离出三种桉烷型倍半萜内酯，即1α-乙酰氧基-8β-甲氧基-10βH-桉烷-7(11)-烯-8α,12-内酯(1)、1α-当归酰氧基-6β-羟基-8β-甲氧基-10βH-桉烷-7(11)-烯-8α,12-内酯(2)和1α-当归酰氧基-8βH,10βH-桉烷-7(11)-烯-8α,12-内酯(3)，以及两种吡咯里西啶生物碱，全缘千里光碱(4)及其N-氧化物(5)。通过核磁共振光谱分析和化学转化确定了新化合物1和2的结构。还对化合物1进行了X射线分析。发现桉烷型倍半萜内酯1和2以及生物碱4和5是强效昆虫拒食剂，进一步支持了这些类化合物具有防御作用的观点。