Chemical synthesis of marine saponins

• Published in: Natural product reports 2019-05, Vol.36 (5), p.769-787
• Main Authors: Xiao, Guozhi, Shao, Xiaofei, Zhu, Dapeng, Yu, Biao
• Format: Article
• Language: English
• Subjects: Aminoglycosides - chemical synthesis; Animals; Aquatic Organisms - chemistry; Cholestenones - chemical synthesis; Cholesterol - analogs & derivatives; Cholesterol - chemical synthesis; Holothurin - analogs & derivatives; Holothurin - chemical synthesis; Saponins - chemical synthesis; Saponins - chemistry; Sea Cucumbers - chemistry; Starfish - chemistry; Steroids - chemical synthesis
• ISSN: 0265-0568; 1460-4752
• DOI: 10.1039/c8np00087e

Covering: 1989-2017 Saponins are characteristic metabolites of starfish and sea cucumbers, and occasionally are also found in sponges, soft coral, and small fish. These steroid or triterpenoid glycosides often show remarkable biological and pharmacological activities, such as antifungal, antifouling, shark repellent, antitumor and anti-inflammatory activities. Over one thousand marine saponins have been characterized; the majority of them can be categorized into three major structural types, i.e. , asterosaponins, polyhydroxysteroid glycosides, and holostane glycosides. Thus far, only 12 marine saponins have been synthesized; those representing the major types were successfully synthesized recently. The syntheses involve preparation of the aglycones from the terrestrial steroid or triterpene materials, installation of the carbohydrate units, and manipulation of the protecting groups. Herein, we provide a comprehensive review on these syntheses. The chemical syntheses of marine saponins are comprehensively reviewed.