Çiçek Serhat S, Galarza Pérez Mayra, Wenzel-Storjohann Arlette, Bezerra Roberto M, Segovia Jorge F O, Girreser Ulrich, Kanzaki Isamu, Tasdemir Deniz
Department of Pharmaceutical Biology, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany.
GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany.
J Nat Prod. 2022 Apr 22;85(4):927-935. doi: 10.1021/acs.jnatprod.1c01035. Epub 2022 Mar 10.
Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (- and ) and six undescribed isoflavones, vatairenones C-H (- and -). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (-) or ring-closed forms (-). The most bioactive compound () exhibited activity against clinically relevant bacteria and fungi with IC values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of in the treatment of dermatological disorders. H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations.
奥布尔豆（豆科）是一种亚马逊药用植物物种，传统上用于治疗皮肤病。在初步筛选中，一种叶提取物及其亚提取物显示出抗菌和抗真菌活性。乙酸乙酯亚提取物被选用于化学分离，得到了五种已知的（-和-）和六种未描述的异黄酮，即瓦泰雷酮C-H（-和-）。所有异黄酮在C-8位均被异戊烯基化，呈现链状异戊烯基化（-）或闭环形式（-）。活性最强的化合物（）对临床相关细菌和真菌具有活性，IC值范围为6.8至26.9μM。由于其广泛的抗菌活性和较低的总体毒性，化合物是进行结构修饰的潜在先导化合物。本研究结果支持了奥布尔豆在治疗皮肤病方面的民族药用用途。一些分离化合物的1H NMR光谱显示出复杂的信号模式，这可能解释了文献中在确定异黄酮B环正确结构时反复出现的错误，我们通过高阶光谱模拟解决了这些问题。
