Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.
Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.
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DOI：
10.1021/np50058a005
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发表时间：
1988-07
影响因子：
5.1
通讯作者：
L. Zalkow;C. F. Asibal;J. Gliński;S. Bonetti;L. Gelbaum;D. Vanderveer;G. Powis
中科院分区：
文献类型：
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作者：
L. Zalkow;C. F. Asibal;J. Gliński;S. Bonetti;L. Gelbaum;D. Vanderveer;G. Powis
从香参中分离得到10个12元大环吡咯利西啶类生物碱，均为香参碱、反香参碱和耳香参碱的酯类。采用液滴逆流色谱法分离得到荆芥碱[1]、荆芥碱[2]、逆转录酶[3]、仙柯碱[5]、新仙柯碱[6]、葡萄碱[10]、羟基仙柯碱[7]和一种新的生物碱，名称为茴香胺[9]。1H nmr检测到usaramine[4]和另一种新的生物碱hydroxyneosenkirkine[8]。此外，还分离出了先前未报道的3a -羟基-4-乙氧基-2,6-过氢吲哚二酮[11]。获得了neosenkirkine[6]、hydroxysenkirkine[7]、anonamine[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分配。用软琼脂糖培养的a204横纹肌肉瘤细胞系测定其抗肿瘤活性。
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.