The Chemical Constituents, Biological Synthesis and Pharmacological Effects of the genus Polygonatum Saponins: A Review

doi:10.11924/j.issn.1000-6850.casb2024-0141

Abstract

Abstract:

The genus Polygonatum Mill, commonly referred to as "Huang Jing," are plants renowned for their medicinal and edible properties. Their active constituents, including polysaccharides, flavonoids, and saponins, exhibit notable pharmacological effects. Recent studies have predominantly centered on the extraction of saponin components from the genus Polygonatum, which are attributed with anti-fatigue, antioxidant, hypoglycemic, lipid-lowering, and immune-enhancing properties. While there has been some advancement in the structural analysis of the genus Polygonatum saponins, their biosynthetic pathways remain underexplored. The synthesis of saponins in the genus Polygonatum occurs via the mevalonic acid pathway and the 2-C-methyl-D-erythritol-4-phosphate pathway, encompassing multiple enzymatic steps. This research indicates that the genus Polygonatum saponins exert diverse biological effects, including anti-tumor, antibacterial, anti-inflammatory, antiviral, and immune regulatory activities, and hold significant potential in medicine, food, cosmetics, and other sectors. Nonetheless, current studies are limited by inadequate structural analysis, an incomplete understanding of biosynthetic pathways, and ambiguous mechanisms of pharmacological action. Future endeavors should prioritize the isolation, structural analysis, synthetic biology, and pharmacology of the genus Polygonatum saponins to advance their scientific investigation and product development, thereby laying a foundation for the creation of novel therapeutic agents.

Key words: Polygonatum spp, saponins, chemical composition, biological synthesis, pharmacological activity, antioxidant activity

ZHAI Yufeng, DING Lan, YU Yemin, JIA Qiaojun, LIANG Zongsuo, WANG Dekai. The Chemical Constituents, Biological Synthesis and Pharmacological Effects of the genus Polygonatum Saponins: A Review[J]. Chinese Agricultural Science Bulletin, 2024, 40(29): 21-30.

Figures/Tables 5

References 60

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来源	皂苷类化合物名称	参考文献
滇黄精 Polygonatum kingianum	kingianosides A，kingianosides B，kingianosides C，kingianosides D	[12]
	6-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-3β,6α,12β,25-tetrahydroxy-(20S,24R)-epoxy-dammarane	[13]
	kingianoside H、kingianoside I、ginsenoside-Rc、(25R)-spirost-5-en-3β,17a-diol-3-O-a-L-rhamnopyra-nosyl-（1→4）-a-L-rhamnopyranosyl-（1→4）-[a-L-rhamnopy-ranosyl-（1→2）]-β-D-glucopyranoside; （25R）-spirost-5-en-3β,17a-diol-3-O-β-D-glucopyranosyl-（1→3）-[a-L-rhamnopyranosyl-（1→2）]-β-D-glucopyranoside; polygonatoside C1; ophiopogonin C’;	[14]
	kingianoside K，(3β,23S,25R)-23-hydroxy-12-oxospirost-5-en-3-yl 4-O-β-D-glucopyranosyl-β-D-galactopyranoside	[15]
黄精 Polygonatum sibiricum	Huangjinoside A，Huangjinoside B，Huangjinoside C，Huangjinoside D，Huangjinoside E，Huangjinoside F; Huangjinoside G; Huangjinoside H; Huangjinoside I; Huangjinoside J; Huangjinoside K; Huangjinoside L; Huangjinoside M; Huangjinoside N; Huangjinoside O; Huangjinoside P; Huangjinoside Q; Huangjinoside R;	[16]
	asiaticoside，Oleanane-type saponins，madecassoside，3β(OH)-(3→1)glucose-(4→1)glucose(28→1)arabinose-（2→1）arabinose-oleanolic acid;	[17]
	3-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-[α-L-rhamnopyranosyl（1→2）]-β-D-glucopyranosyl-diosgenin; 3-O-β-D-glucopyranosyl（1→4）-[α-L-rhamnopyranosyl（1→2）]-β-D-glucopyranosyl-diosgenin;	[9]
	3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl -(25R)-spirost-5-en-3β,17α-diol， 3-O-β-D-glucopyranosyl（1→4）-β-D- fucopyranosyl-（25S）-spirost-5-en-3β,17α-diol; 3-O-β-D-glucopyranosyl（1→2）-β-D-glucopyranosyl（1→4）-β-D-fucopyranosyl-（25R）-spirost-5-en-3β,17α-diol;3-O-β-D-glucopyranosyl（1→4）-β-D-fucopyranosyl-（25R/S）-spirost-5-en-3β,12β-diol;	[18]
	polygonoside 1，polygonoside 2，polygonoside 3，polygonoside，polygonoside 5，polygonoside 6，polygonoside 7	[19]
	polygodoside F，yamogenin 3-O-β-lycotetraoside，gentrogenin 3-O-β-lycotetraoside，neoprazerigenin A 3-O-β-lycotetraoside; diosgenin 3-O-β-lycotetraoside; madecassoside; diosgenin 3-O-α-L-rhamnopyranosyl-（1→2）-[O-α-L-arabinofuranosyl-（1→4）]-β-D-glucopyranoside; prosapogenin B of dioscin; neoprazerigenin A; （25R）-kingianoside G; acutoside A; diosgenin 3-O-β-D-glucopyranosyl-（1→4）-[α-L-rhamnopyranosyl-（1→2）]-β-D-glucopyranoside	[20]
	Polygonoides C (1)，Polygonoides D (2)，Polygonoides E (3)	[21]
点花黄精 Polygonatum punctatum	Polypunctatoside A，PolypunctatosideB，PolypunctatosideC，PolypunctatosideD，Polypunctatoside E，dioscin;protodioscin; 3-O-α-L-rhamnopyranosyl（1→2）[α-L-arabinofuranosyl（1→4）]-β-D-glucopyranoside; prosapogenin A of dioscin; proto-type of prosapogenin A of dioscin;	[22]
轮叶黄精 Polygonatum verticillatum	26-O-β-D-glucopyranosyl-22ξ-hydroxy-(25R)-furost-5-en-3β,26-diol,3-O-β[xylopyranosyl(1→3)α-L-rhamnopyranosyl（1→2）β-D-glucopyranoside]; 3-O-β-D-xylopyranosyl（1→3）α-L-rhamnopyranosyl（1→3）β-D-glucopyranoside diosgenin;	[23]
多花黄精 Polygonatum cyrtonema	(25R)spirostan-5-en-12-one-3-O-β-D-glucopyranosyl-(1→2)O-[β-D-glucopyranosyl-（1→3）]-O-β-D-glucopyranosyl-（1→4）-β-D-galactopyranoside; （25S）spirostan-5-en-12-one-3-O-β-D-glucopyranosyl-（1→2）O-[β-D-glucopyranosyl-（1→3）]-O-β-D-glucopyranosyl-（1→4）-β-D-galactopyranoside （25R）spirostan-5-en-12-one-3-O-D-glucopyranosyl-（1→2）-O-[β-D-xylopyranosyl（1→3）]-O-β-Dglucopyranosyl（1→4）-β-D-galactopyranoside; （25S）spirostan-5-en-12-one-3-O-D-glucopyranosyl-（1→2）-O-[β-D-xylopyranosyl（1→3）]-O-β-Dglucopyranosyl（1→4）-β-D-galactopyranoside 25R-3-β-hydroxyspirost-5-en-12-one; 25S-3-β-hydroxyspirost-5-en-12-one	[24]

来源	皂苷类化合物名称	参考文献
滇黄精 Polygonatum kingianum	kingianosides A，kingianosides B，kingianosides C，kingianosides D	[12]
	6-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-3β,6α,12β,25-tetrahydroxy-(20S,24R)-epoxy-dammarane	[13]
	kingianoside H、kingianoside I、ginsenoside-Rc、(25R)-spirost-5-en-3β,17a-diol-3-O-a-L-rhamnopyra-nosyl-（1→4）-a-L-rhamnopyranosyl-（1→4）-[a-L-rhamnopy-ranosyl-（1→2）]-β-D-glucopyranoside; （25R）-spirost-5-en-3β,17a-diol-3-O-β-D-glucopyranosyl-（1→3）-[a-L-rhamnopyranosyl-（1→2）]-β-D-glucopyranoside; polygonatoside C1; ophiopogonin C’;	[14]
	kingianoside K，(3β,23S,25R)-23-hydroxy-12-oxospirost-5-en-3-yl 4-O-β-D-glucopyranosyl-β-D-galactopyranoside	[15]
黄精 Polygonatum sibiricum	Huangjinoside A，Huangjinoside B，Huangjinoside C，Huangjinoside D，Huangjinoside E，Huangjinoside F; Huangjinoside G; Huangjinoside H; Huangjinoside I; Huangjinoside J; Huangjinoside K; Huangjinoside L; Huangjinoside M; Huangjinoside N; Huangjinoside O; Huangjinoside P; Huangjinoside Q; Huangjinoside R;	[16]
	asiaticoside，Oleanane-type saponins，madecassoside，3β(OH)-(3→1)glucose-(4→1)glucose(28→1)arabinose-（2→1）arabinose-oleanolic acid;	[17]
	3-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-[α-L-rhamnopyranosyl（1→2）]-β-D-glucopyranosyl-diosgenin; 3-O-β-D-glucopyranosyl（1→4）-[α-L-rhamnopyranosyl（1→2）]-β-D-glucopyranosyl-diosgenin;	[9]
	3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl -(25R)-spirost-5-en-3β,17α-diol， 3-O-β-D-glucopyranosyl（1→4）-β-D- fucopyranosyl-（25S）-spirost-5-en-3β,17α-diol; 3-O-β-D-glucopyranosyl（1→2）-β-D-glucopyranosyl（1→4）-β-D-fucopyranosyl-（25R）-spirost-5-en-3β,17α-diol;3-O-β-D-glucopyranosyl（1→4）-β-D-fucopyranosyl-（25R/S）-spirost-5-en-3β,12β-diol;	[18]
	polygonoside 1，polygonoside 2，polygonoside 3，polygonoside，polygonoside 5，polygonoside 6，polygonoside 7	[19]
	polygodoside F，yamogenin 3-O-β-lycotetraoside，gentrogenin 3-O-β-lycotetraoside，neoprazerigenin A 3-O-β-lycotetraoside; diosgenin 3-O-β-lycotetraoside; madecassoside; diosgenin 3-O-α-L-rhamnopyranosyl-（1→2）-[O-α-L-arabinofuranosyl-（1→4）]-β-D-glucopyranoside; prosapogenin B of dioscin; neoprazerigenin A; （25R）-kingianoside G; acutoside A; diosgenin 3-O-β-D-glucopyranosyl-（1→4）-[α-L-rhamnopyranosyl-（1→2）]-β-D-glucopyranoside	[20]
	Polygonoides C (1)，Polygonoides D (2)，Polygonoides E (3)	[21]
点花黄精 Polygonatum punctatum	Polypunctatoside A，PolypunctatosideB，PolypunctatosideC，PolypunctatosideD，Polypunctatoside E，dioscin;protodioscin; 3-O-α-L-rhamnopyranosyl（1→2）[α-L-arabinofuranosyl（1→4）]-β-D-glucopyranoside; prosapogenin A of dioscin; proto-type of prosapogenin A of dioscin;	[22]
轮叶黄精 Polygonatum verticillatum	26-O-β-D-glucopyranosyl-22ξ-hydroxy-(25R)-furost-5-en-3β,26-diol,3-O-β[xylopyranosyl(1→3)α-L-rhamnopyranosyl（1→2）β-D-glucopyranoside]; 3-O-β-D-xylopyranosyl（1→3）α-L-rhamnopyranosyl（1→3）β-D-glucopyranoside diosgenin;	[23]
多花黄精 Polygonatum cyrtonema	(25R)spirostan-5-en-12-one-3-O-β-D-glucopyranosyl-(1→2)O-[β-D-glucopyranosyl-（1→3）]-O-β-D-glucopyranosyl-（1→4）-β-D-galactopyranoside; （25S）spirostan-5-en-12-one-3-O-β-D-glucopyranosyl-（1→2）O-[β-D-glucopyranosyl-（1→3）]-O-β-D-glucopyranosyl-（1→4）-β-D-galactopyranoside （25R）spirostan-5-en-12-one-3-O-D-glucopyranosyl-（1→2）-O-[β-D-xylopyranosyl（1→3）]-O-β-Dglucopyranosyl（1→4）-β-D-galactopyranoside; （25S）spirostan-5-en-12-one-3-O-D-glucopyranosyl-（1→2）-O-[β-D-xylopyranosyl（1→3）]-O-β-Dglucopyranosyl（1→4）-β-D-galactopyranoside 25R-3-β-hydroxyspirost-5-en-12-one; 25S-3-β-hydroxyspirost-5-en-12-one	[24]