lupalbigenin 和 isolupalbigenin 的全合成和抗菌评价。

IF 1.3 3区医学 Q3 CHEMISTRY, APPLIED

Journal of Asian Natural Products Research Pub Date : 2024-11-21 DOI:10.1080/10286020.2024.2428794

Li Liao, Na Wang, Ling Mei, Bin Long, Tong Luo, Meng-Qi Wang, Lan Lu, Hong-Bo Dong

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引用次数: 0

摘要

羽扇豆甙元（1）是从大戟科植物 Maclura cochinchinensis (Lour.) Corner 中分离出来的一种抗菌异黄酮。在这项研究中，我们首次从市售的染料木素（2）中合成了克级规模的羽扇豆甙元（1），产率为 47.7%。关键步骤是通过克莱森重排，同时在羽扇豆甙元（1）的 C-6 和 C-11 位置上安装两个炔基。抗菌活性测定显示，羽扇豆甙元（1）具有快速杀菌活性，可抑制α-溶血素和生物膜的形成，并能破坏细菌细胞膜。这些研究结果表明，狼尾草甙元 (1) 是开发新型抗生素以抗击细菌感染的理想候选物质。

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Total synthesis and antibacterial evaluation of lupalbigenin and isolupalbigenin.

Lupalbigenin (1) is an antibacterial isoflavone isolated from Maclura cochinchinensis (Lour.) Corner (Moraceae). In this study, we achieved the first gram-scale synthesis of lupalbigenin (1) from commercially available genistein (2), with a yield of 47.7%. The key step was a Claisen rearrangement that simultaneously installed two prenyl groups at the C-6 and C-11 positions of lupalbigenin (1). Antimicrobial activity assays revealed that lupalbigenin (1) exhibited rapid bactericidal activity, inhibited α-hemolysin and biofilm formation, and disrupted bacterial cell membranes. These findings suggest that lupalbigenin (1) is a promising candidate for the development of novel antibiotics to combat bacterial infections.

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来源期刊

Journal of Asian Natural Products Research 医学-药学

CiteScore

3.20

自引率

5.90%

发文量

审稿时长

2.3 months

期刊介绍： The Journal of Asian Natural Products Research (JANPR) publishes chemical and pharmaceutical studies in the English language in the field of natural product research on Asian ethnic medicine. The journal publishes work from scientists in Asian countries, e.g. China, Japan, Korea and India, including contributions from other countries concerning natural products of Asia. The journal is chemistry-orientated. Major fields covered are: isolation and structural elucidation of natural constituents (including those for non-medical uses), synthesis and transformation (including biosynthesis and biotransformation) of natural products, pharmacognosy, and allied topics. Biological evaluation of crude extracts are acceptable only as supporting data for pure isolates with well-characterized structures. All published research articles in this journal have undergone rigorous peer review, based on initial editor screening and anonymized refereeing by at least two expert referees.