Abstract
Saponins are amphiphilic molecules consisting of carbohydrate and either triterpenoid or steroid aglycone moieties and are noted for their multiple biological activities—Fungicidal, antimicrobial, antiviral, anti-inflammatory, anticancer, antioxidant and immunomodulatory effects have all been observed. Saponins from natural sources have long been used in herbal and traditional medicines; however, the isolation of complexed saponins from nature is difficult and laborious, due to the scarce amount and structure heterogeneity. Chemical synthesis is considered a powerful tool to expand the structural diversity of saponin, leading to the discovery of promising compounds. This review focuses on recent developments in the structure optimization and biological evaluation of synthetic triterpenoid and steroid saponin derivatives. By summarizing the structure–activity relationship (SAR) results, we hope to provide the direction for future development of saponin-based bioactive compounds.
Highlights
IntroductionThe name “saponin” is derived from the Latin word sapo, meaning soap-like foam-generating ability, and the amphiphilic properties derived from the structure containing an isoprenoid-derived aglycone (a sapogenin) attached to one or more sugar chains by either an ether or ester linkage
The name “saponin” is derived from the Latin word sapo, meaning soap-like foam-generating ability, and the amphiphilic properties derived from the structure containing an isoprenoid-derived aglycone attached to one or more sugar chains by either an ether or ester linkage.Structural classification of saponins is primarily based on their sapogenin skeletons, which can be divided into two main groups—Triterpenoid saponins and steroid saponins [1,2]
Triterpenoid saponins are broadly distributed in dicotyledons, including four major skeletons—Pentacyclic oleanane, ursane, lupane, and tetracyclic dammarane (Figure 1a); steroid saponins are mostly derived from monocotyledons, comprised of four major skeletons—Tetracyclic cholestane, hexacyclic spirostane, pentacyclic furostane, and lactone-bearing cardenolide (Figure 1b)
Summary
The name “saponin” is derived from the Latin word sapo, meaning soap-like foam-generating ability, and the amphiphilic properties derived from the structure containing an isoprenoid-derived aglycone (a sapogenin) attached to one or more sugar chains by either an ether or ester linkage. As a result, applying an organic synthesis method to generate artificial saponins is a promising way to efficiently expand the structure library and search for highly active compounds [6,7]. Based on the research experiences on carbohydrate [8,9] and medicinal [10,11,12,13,14,15,16,17,18,19,20,21,22] chemistry in our lab, we summarize the biological effects and preliminary SAR results of synthetic saponins over the last five years to serve as a bridge between chemistry and biology, providing an insight for further structure optimization and mechanism studies, facilitating the development of saponin-based bioactive compounds
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