Molecular Structure of the Pyrrolizidine Alkaloid Trichodesmin from Rindera oblongifolia

IF 0.8 4区 化学 Q4 CHEMISTRY, MEDICINAL Chemistry of Natural Compounds Pub Date : 2024-09-17 DOI:10.1007/s10600-024-04472-7
R. M. Ruzibaeva, R. Ya. Okmanov, B. Tashkhodzhaev, N. I. Mukarramov, A. G. Eshimbetov, A. M. Nigmatullaev
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Abstract

The known pyrrolizidine alkaloids trichodesmine, trichodesmine N-oxide, lindelofine, and trichelanthic acid were isolated from Rindera oblongifolia for the first time. The absolute configurations of the chiral centers of trichodesmine, which contains an 11-membered macrocycle, were established as 7R,8R,11R,12R,13R by an X-ray crystal structure analysis. A study of the conformation of trichodesmine showed that the nature of intra- and intermolecular H-bonds and packing factors were decisive in realizing one conformer or another of the 11-membered macrocycle.

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Rindera oblongifolia 中的吡咯烷类生物碱 Trichodesmin 的分子结构
首次从Rindera oblongifolia中分离出了已知的吡咯烷生物碱trichodesmine、trichodesmine N-oxide、lindelofine和trichelanthic acid。通过 X 射线晶体结构分析,确定了含有 11 元大环的 trichodesmine 手性中心的绝对构型为 7R、8R、11R、12R、13R。对三氯地明构象的研究表明,分子内和分子间氢键的性质以及堆积因素对实现 11 元大环的一种或另一种构象起着决定性作用。
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来源期刊
Chemistry of Natural Compounds
Chemistry of Natural Compounds 化学-有机化学
CiteScore
1.40
自引率
25.00%
发文量
265
审稿时长
7.8 months
期刊介绍: Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.
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