来自无名千里光的大环吡咯里西啶生物碱。使用液滴逆流色谱法分离复杂生物碱提取物。

Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.

作者信息

Zalkow L H, Asibal C F, Glinski J A, Bonetti S J, Gelbaum L T, VanDerveer D, Powis G

机构信息

School of Chemistry, Georgia Institute of Technology, Atlanta 30332.

出版信息

J Nat Prod. 1988 Jul-Aug;51(4):690-702. doi: 10.1021/np50058a005.

DOI:10.1021/np50058a005

PMID:3210016

Abstract

Ten 12-membered macrocyclic pyrrolizidine alkaloids, all of them esters of the necines, retronecine or otonecine, have been isolated from Senecio anonymus. The separation, carried out by droplet counter-current chromatography, afforded senecionine [1], integerrimine [2], retrorsine [3], senkirkine [5], neosenkirkine [6], otosenine [10], hydroxysenkirkine [7], and a new alkaloid given the trivial name anonamine [9]. Traces of usaramine [4] and another new alkaloid, hydroxyneosenkirkine [8], were detected by 1H nmr. In addition, the previously unreported 3a beta-hydroxy-4-ethoxy-2,6-perhydroindoledione [11] was isolated. X-ray structures were obtained for neosenkirkine [6], hydroxysenkirkine [7], anonamine [9], and [11]. 1H-13C heteronuclear shift correlated nmr (HETCOR) provided unambiguous chemical shift assignments for 13C-nmr data. Antitumor activity was assayed using the A204-rhabdomyosarcoma cell line in soft agarose.

摘要

从隐齿千里光中分离出了10种12元大环吡咯里西啶生物碱，它们均为裂碱、倒千里光碱或奥托千里光碱的酯。通过液滴逆流色谱法进行分离，得到了千里光宁碱[1]、全缘千里光碱[2]、倒千里光碱[3]、Senkirkine[5]、新千里光碱[6]、奥托千里光宁碱[10]、羟基千里光碱[7]，以及一种俗名为阿诺胺的新生物碱[9]。通过1H核磁共振检测到痕量的乌沙胺[4]和另一种新生物碱羟基新千里光碱[8]。此外，还分离出了之前未报道的3aβ-羟基-4-乙氧基-2,6-全氢吲哚二酮[11]。获得了新千里光碱[6]、羟基千里光碱[7]、阿诺胺[9]和[11]的X射线结构。1H-13C异核位移相关核磁共振（HETCOR）为13C核磁共振数据提供了明确的化学位移归属。使用A204横纹肌肉瘤细胞系在软琼脂糖中测定了抗肿瘤活性。