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合果花椒酰胺,一种从合果花椒中提取的新型抗疟原虫(+)-去甲肾上腺素衍生物。

Syncarpamide, a new antiplasmodial (+)-norepinephrine derivative from Zanthoxylum syncarpum.

作者信息

Ross Samir A, Sultana Gazi N N, Burandt Charles L, ElSohly Mahmoud A, Marais Jannie P J, Ferreira Daneel

机构信息

National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677-1848, USA.

出版信息

J Nat Prod. 2004 Jan;67(1):88-90. doi: 10.1021/np030417t.

DOI:10.1021/np030417t
PMID:14738394
Abstract

A new (+)-norepinephrine derivative, syncarpamide (1), along with a known coumarin, (+)-S-marmesin (2), and one known alkaloid, decarine (3), have been isolated from the stem of Zanthoxylum syncarpum. The structure of compound 1 was elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation, and CD analyses. Its absolute stereochemistry was elucidated by synthesis of its enantiomer and subsequent comparison of CD data. Characterizations of compounds 2 and 3 were based on spectral analysis and comparison with reported data. Compounds 1 and 3 showed antiplasmodial activity, with IC(50) values of 2.04 and 1.44 microM against Plasmodium falciparum D(6) clone and 3.06 and 0.88 microM against P. falciparum W(2) clone, respectively. Compound 3 showed cytotoxicity at 56.42 microM, whereas compound 1 was not cytotoxic at 10.42 microM. Compound 1 was tested for hypotensive activity, but no activity was observed. Compound 2 showed no antiplasmodial or antimicrobial activities.

摘要

一种新的(+)-去甲肾上腺素衍生物,合果花椒酰胺(1),与一种已知的香豆素,(+)-S-崖椒素(2),以及一种已知的生物碱,去甲卡里宁(3),已从合果花椒的茎中分离出来。化合物1的结构通过一维和二维核磁共振、质谱、红外光谱、旋光度和圆二色光谱分析得以阐明。其绝对立体化学通过合成其对映体并随后比较圆二色光谱数据得以阐明。化合物2和3的表征基于光谱分析并与已报道的数据进行比较。化合物1和3显示出抗疟活性,对恶性疟原虫D(6)克隆的半数抑制浓度(IC50)值分别为2.04和1.44微摩尔,对恶性疟原虫W(2)克隆的IC50值分别为3.06和0.88微摩尔。化合物3在56.42微摩尔时显示出细胞毒性,而化合物1在10.42微摩尔时无细胞毒性。对化合物1进行了降压活性测试,但未观察到活性。化合物2未显示出抗疟或抗菌活性。

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