3α-Hydroxybufadienolides in Bufo gallbladders: structural insights and biotransformation

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL Natural Products and Bioprospecting Pub Date : 2024-03-04 DOI:10.1007/s13659-024-00442-2

Li-Jun Ruan, Zhi-Jun Song, Ren-Wang Jiang

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Abstract

Bufadienolides, naturally occurring steroids primarily found in toads, have garnered attention for their pharmacological properties and ecological significance. In this study, we isolated and identified 21 bufadienolides from the gallbladders of Bufo gargarizans, comprising four new compounds and 17 known ones. Notably, the predominance of 15 bufadienolides with a 3α-OH configuration in toad bile differs significantly from the 3β-OH bufadienolides found in venom secreted by toad glands. Moreover, our investigation into the biotransformation of 3β-OH and 3α-OH bufadienolides in the liver and kidney tissues of toads revealed an irreversible conversion from 3β-OH to 3α-OH bufadienolides, suggesting a crucial role in toad self-detoxification. These findings provide valuable insights into the structural diversity of bufadienolides and advance our understanding of their medical and ecological significance.

Graphical Abstract

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蟾蜍胆中的 3α-Hydroxybufadienolides: 结构见解和生物转化。

蟾蜍内酯（Bufadienolides）是主要存在于蟾蜍体内的天然类固醇，因其药理特性和生态学意义而备受关注。在这项研究中，我们从蟾蜍的胆囊中分离并鉴定了 21 种 bufadienolides，其中包括 4 种新化合物和 17 种已知化合物。值得注意的是，蟾蜍胆汁中主要含有 15 种 3α-OH 构型的布法迪内酯，这与蟾蜍腺体分泌的毒液中发现的 3β-OH 布法迪内酯有很大不同。此外，我们对 3β-OH 和 3α-OH 布法二烯醇内酯在蟾蜍肝脏和肾脏组织中的生物转化进行了研究，结果发现，3β-OH 布法二烯醇内酯向 3α-OH 布法二烯醇内酯的转化是不可逆的，这表明布法二烯醇内酯在蟾蜍的自我解毒过程中起着至关重要的作用。这些发现为我们了解布法迪烯醇内酯的结构多样性提供了宝贵的视角，并加深了我们对其医疗和生态意义的理解。

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.