Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-10-26 DOI:10.1021/acs.jnatprod.4c00751

Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina

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Abstract

The phytochemical investigation of the MeOH extract of Astragalus condensatus roots led to the discovery of a new tetrahydropyran cycloartane-type triterpenoid, astracondensatol A (1), alongside six known cyclocephagenol derivatives (2, 3, 20, 32, 35, and 36). Elucidation of their structures involved 1D and 2D-NMR spectroscopy and mass data analysis. Upon comparing NMR spectroscopic data with prior literature, several carbon shift anomalies, particularly at C-24, prompted a reevaluation using quantum chemical calculations, resulting in the revision of the 24S to 24R absolute configuration for compound 2 and 38 other reported cyclocephagenol-type triterpenoids. X-ray crystallography data further supported the analysis in establishing the absolute configuration of compound 2. Ambiguous NOE correlations and publication bias could have played a significant role in miss-assigning the C-24 absolute configuration in tetrahydropyran cycloartane-type triterpenoids.

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通过黄芪重新审视环黄芪醇：结构见解和构型修正。

通过对黄芪根的 MeOH 提取物进行植物化学研究，发现了一种新的四氢吡喃环安坦类三萜类化合物 astracondensatol A（1），以及六种已知的环黄芪醇衍生物（2、3、20、32、35 和 36）。对它们的结构的阐明涉及一维和二维核磁共振光谱以及质量数据分析。将核磁共振光谱数据与之前的文献进行比较后，发现了几个碳位移异常点，尤其是 C-24 碳位移异常点，这促使我们使用量子化学计算方法对其进行了重新评估，从而将化合物 2 和其他 38 种已报道的环石竹烯醇型三萜类化合物的绝对构型从 24S 修改为 24R。X 射线晶体学数据进一步支持了确定化合物 2 绝对构型的分析。不明确的 NOE 相关性和出版偏差可能在错误指定四氢吡喃环安坦类三萜化合物的 C-24 绝对构型方面起了重要作用。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.