Stereoisomers of Eudesmane Sesquiterpene From Cleome droserifolia

IF 3 4区化学 Q2 CHEMISTRY, ANALYTICAL

Chirality Pub Date : 2025-06-02 DOI:10.1002/chir.70038

Sarfaraz Ahmed, Mohammad Nur-e-Alam, Umberto Calice, Patrizia Scafato, James B. Orton, Maria Grazia Bonomo, Hattan A. Alharbi, Omer I. Fantoukh, Stefano Superchi, Adnan J. Al-Rehaily

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Abstract

The present study reports the chemical investigation on the aerial parts of Cleome droserifolia yielding the related eudesmane sesquiterpene solyraterpenoid A (1) and the novel cledrone A (2) from the acetonitrile fraction of the dichloromethane extract. These compounds were separated by column chromatography, centrifugal thin layer chromatography (CTLC) followed by semipreparative reversed-phase high performance liquid chromatography (RP-HPLC). The chemical structure of these compounds was determined by mono and bidimensional NMR techniques, IR spectroscopy, and HRESIMS, while the absolute configuration was established by computational analysis of ECD spectra. Furthermore, the structure and absolute configuration of both 1 and 2 were unambiguously confirmed via single crystal X-ray diffraction (scXRD). Both compounds showed antibacterial activity against Escherichia coli and Pseudomonas aeruginosa strains, with compound 2 being more active.

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桂花倍半萜的立体异构体研究

本研究报道了从二氯甲烷提取物的乙腈馏分中分离得到相关的环氧萜类倍半萜-巯基萜类A(1)和新型环氧萜类A(2)的化学性质。采用柱层析、离心薄层析（CTLC）和半制备反相高效液相色谱（RP-HPLC）对化合物进行分离。这些化合物的化学结构通过单、二维核磁共振技术、红外光谱和hresms测定，并通过ECD谱计算分析确定了绝对构型。此外，通过单晶x射线衍射（scXRD）明确了1和2的结构和绝对构型。两种化合物对大肠杆菌和铜绿假单胞菌均有抑菌活性，其中化合物2的抑菌活性更强。

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

Chirality 医学-分析化学

CiteScore

4.40

自引率

5.00%

发文量

124

审稿时长

1 months

期刊介绍： The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties. Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.