Anti-inflammatory Alkaloids, Papaversomni A, a Hexacyclic-Membered Morphinan, and Two Pairs of E/Z Nonseparable Stereoisomers, Papaversomni C and Sinoracutinal, from Papaver somniferum.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-15 DOI:10.1021/acs.orglett.5c03443

Desire Girimpuhwe,Wei Hao Li,Zuo Qing Yu,Hao Ren,Ke-Jin Zhu,Chun-An Fan,Quan-Xiang Wu

引用次数: 0

Abstract

Five new alkaloids, including papaversomnis A-C (1, 3, and 4), sinoracutinal (5), and ethoxyepiglaudine (6), along with two known alkaloids, 2 and 7, were discovered from Papaver somniferum. 1 has unprecedented 6/6/6/6/5/5-fused hexacyclic framework, representing a novel type of morphinan, whereas 4 and 5 are two pairs of E/Z nonseparable stereoisomers. Their stereochemistries were identified via single crystal X-ray diffraction analysis, the exciton chirality method evaluation of ECD, comparison of the experimental and calculated 1H and 13C NMR, and ECD data. 1 and 2 exhibited stronger anti-inflammatory effects on NO production in lipopolysaccharide-stimulated RAW 264.7 macrophages, with IC50 values of 16.63 ± 0.83 and 12.78 ± 0.95 μM, respectively, than the positive control, with IC50 value of 22.10 ± 0.63 μM. Western blotting analysis displayed that 1 and 2 could inhibit the expression of iNOS and COX-2 as key mediators in the inflammatory responses.

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从木瓜中分离出抗炎生物碱——六环氨基吗啡酮A和两对E/Z不可分离的立体异构体木瓜C和紫丁香碱。

从罂粟中发现了5个新的生物碱，包括罂粟碱A-C（1、3、4）、辛草碱(5)和乙氧基比劳丁(6)，以及2个已知的生物碱2和7。1具有前所未有的6/6/6/6/5/5融合的六环框架，代表了一种新型的morphinan，而4和5是两对E/Z不可分离的立体异构体。通过单晶x射线衍射分析、ECD的激子手性方法评价、1H和13C核磁共振实验和计算结果的比较以及ECD数据，确定了它们的立体化学性质。1和2对脂多糖刺激的RAW 264.7巨噬细胞产生NO具有较强的抗炎作用，IC50值分别为16.63±0.83和12.78±0.95 μM，高于阳性对照的22.10±0.63 μM。Western blotting分析显示，1和2可以抑制iNOS和COX-2的表达，而iNOS和COX-2是炎症反应的关键介质。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.