Structure and hemolytic activity relationships of triterpenoid saponins and sapogenins

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• 作者：Nhu Ngoc Quynh Vo ; Ery Odette Fukushima ; Toshiya Muranaka
• 关键词：Hemolytic activity ; Structure–activity relationships ; Hemolytic time course ; Triterpene saponins and sapogenins
• 刊名：Journal of Natural Medicines
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：71
• 期：1
• 页码：50-58
• 全文大小：
• 刊物主题：Pharmacology/Toxicology; Plant Sciences; Complementary & Alternative Medicine; Medicinal Chemistry; Pharmacy;
• 出版者：Springer Japan
• ISSN：1861-0293
• 卷排序：71

文摘

We evaluated the hemolytic activity of 41 commercially available triterpenoid saponins and sapogenins derived from three types of structural skeletons. Structure–activity relationships were established by comparing the structural characteristics of both the aglycone and sugar moieties among the tested compounds. The majority of oleanane-type sapogenins had stronger hemolytic effects than those of the ursane and dammarane types. The presence of polar regions on sapogenins, such as a carboxyl (COOH) at position 28, an α-hydroxyl (α-OH) at position 16, and/or a β-hydroxyl (β-OH) at position 2, significantly enhanced hemolysis. Meanwhile, the introduction of an α-OH at position 2 or a methyl hydroxyl (CH₂OH) at positions 23 or 24 was closely associated with reduced activity. Our findings suggest that not only the complexity of sugar moieties but also the types and stereochemical configurations of functional groups at different positions, as well as the skeleton types, are important structural features affecting hemolytic potential. Our results provide a baseline in terms of the toxicity of saponins and sapogenins to erythrocytes, which holds promise for drug development.