Soyasaponin II
(Synonyms: 大豆皂苷II) 目录号 : GC61284SoyasaponinII是具有抗病毒活性的皂苷。SoyasaponinII抑制HSV-1,HCMV,流感病毒和HIV-1的复制。SoyasaponinII对HSV-1复制显示出有效的抑制作用。SoyasaponinII作为YB-1磷酸化和NLRP3炎性小体引发的抑制剂,可保护小鼠免受LPS/GalN诱导的急性肝衰竭。
Cas No.:55319-36-3
Sample solution is provided at 25 µL, 10mM.
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Soyasaponin II is a saponin with antiviral activity. Soyasaponin II inhibits the replication of HSV-1, HCMV, influenza virus, and HIV-1. Soyasaponin II shows potent inhibition on HSV-1 replication. Soyasaponin II serves as a inhibitor for YB-1 phosphorylation and NLRP3 inflammasome priming and could protect mice against LPS/GalN induced acute liver failure[1][2].
Soyasaponin II inhibits the replication of HSV-1 (IC50=54μM), HCMV (104μM), influenza virus (88μM), and HIV-1 (112 μM)[1].
Soyasaponin II (5 mg/kg; p.o.; once a day for three consecutive days) ameliorates canonical NLRP3 inflammasome-associated innate immune response[2].
[1]. Hayashi K, et al. Inhibitory activity of soyasaponin II on virus replication in vitro. Planta Med. 1997;63(2):102-105. [2]. Wang F, et al. Soyasaponin II protects against acute liver failure through diminishing YB-1 phosphorylation and Nlrp3-inflammasome priming in mice. Theranostics. 2020;10(6):2714-2726. Published 2020 Feb 3.
Cas No. | 55319-36-3 | SDF | |
别名 | 大豆皂苷II | ||
Canonical SMILES | C[C@]12[C@@](CC=C3[C@]2(CC[C@@]4([C@@]3([H])CC(C)(C[C@H]4O)C)C)C)([H])[C@@]5([C@@]([C@](C)([C@H](CC5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(O)=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)CO)([H])CC1)C | ||
分子式 | C47H76O17 | 分子量 | 913.1 |
溶解度 | 储存条件 | -20°C, protect from light | |
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Soyasaponin II protects against acute liver failure through diminishing YB-1 phosphorylation and Nlrp3-inflammasome priming in mice
Theranostics 2020 Feb 3;10(6):2714-2726.PMID:32194830DOI:10.7150/thno.40128.
Acute liver failure is characterized by the rapid development of liver dysfunction and remarkably high mortality. Accumulating evidence suggests that soyasaponin possesses potential anti-inflammatory activities. Here, we aimed to investigate the potential role of Soyasaponin II in acute liver failure and establish the underlying mechanism. Methods: Lipopolysaccharide/D-galactosamine (LPS/GalN) was employed to induce acute liver failure. We applied liquid chromatography and mass spectrometry (LC/MS) to characterize the changes of Soyasaponin II levels in the cecal content and liver. Transcriptomics and proteomics analysis were used to evaluate the functional molecule mediated by Soyasaponin II in macrophages. Results: LPS/GalN administration markedly decreased fecal and hepatic Soyasaponin II levels. Soyasaponin II treatment protected mice against LPS/GalN induced acute liver injury. Additionally, Soyasaponin II markedly diminished Y-Box Binding Protein 1 (YB-1) phosphorylation and nuclear translocation, Nlrp3 inflammasome priming, and interleukin 1β (Il-1β) production in macrophages. Phosphorylated YB-1 could activate Nlrp3 mRNA transcription by binding the promoter region. Finally, immunofluorescence analysis showed elevated p-YB-1 nuclear translocation in macrophages of acute liver failure patients compared to controls. Conclusion: Our data shows that Soyasaponin II which serves as a novel inhibitor for YB-1 phosphorylation and Nlrp3 inflammasome priming could protect mice against LPS/GalN induced acute liver failure.
Inhibitory activity of Soyasaponin II on virus replication in vitro
Planta Med 1997 Apr;63(2):102-5.PMID:9140220DOI:10.1055/s-2006-957622.
The antiviral activities of two saponins, soyasaponin I and II, isolated from soybean (Glycine max Merrill) were studied in vitro against herpes simplex virus type 1 (HSV-1). Soyasaponin II was more potent than soyasaponin I as shown by reduction of HSV-1 production. Soyasaponin II was also found to inhibit the replication of human cytomegalovirus, influenza virus, and human immunodeficiency virus type 1. The action was not due to inhibition of virus penetration and protein synthesis, but might involve a virucidal effect. When acyclovir and Soyasaponin II were evaluated in combination for anti-HSV-1 activity, additive antiviral effects were observed for this virus.
A novel saponin hydrolase from Neocosmospora vasinfecta var. vasinfecta
Appl Environ Microbiol 2004 Feb;70(2):865-72.PMID:14766566DOI:10.1128/AEM.70.2.865-872.2004.
We isolated a soybean saponin hydrolase from Neocosmospora vasinfecta var. vasinfecta PF1225, a filamentous fungus that can degrade soybean saponin and generate soyasapogenol B. This enzyme was found to be a monomer with a molecular mass of about 77 kDa and a glycoprotein. Nucleotide sequence analysis of the corresponding gene (sdn1) indicated that this enzyme consisted of 612 amino acids and had a molecular mass of 65,724 Da, in close agreement with that of the apoenzyme after the removal of carbohydrates. The sdn1 gene was successfully expressed in Trichoderma viride under the control of the cellobiohydrolase I gene promoter. The molecular mass of the recombinant enzyme, about 69 kDa, was smaller than that of the native enzyme due to fewer carbohydrate modifications. Examination of the degradation products obtained by treatment of soyasaponin I with the recombinant enzyme showed that the enzyme hydrolyzed soyasaponin I to soyasapogenol B and triose [alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-D-glucuronopyranoside]. Also, when Soyasaponin II and soyasaponin V, which are different from soyasaponin I only in constituent saccharides, were treated with the enzyme, the ratio of the reaction velocities for soyasaponin I, Soyasaponin II, and soyasaponin V was 2,680:886:1. These results indicate that this enzyme recognizes the fine structure of the carbohydrate moiety of soyasaponin in its catalytic reaction. The amino acid sequence of this enzyme predicted from the DNA sequence shows no clear homology with those of any of the enzymes involved in the hydrolysis of carbohydrates.
Saponins from Trifolium repens
Phytochemistry 1992 May;31(5):1773-7.PMID:1368366DOI:10.1016/0031-9422(92)83145-o.
From the whole plant of white clover, Trifolium repens, five new triterpenoid saponins, designated cloversaponins I-V, were isolated together with four known saponins, beta-D-glucoronopyranosylsoyasapogenol B, soyasaponin I, Soyasaponin II and azukisaponin II as their methyl esters. Their structures were determined by 2H NMR and 13C NMR spectroscopy and chemical evidence.
Analysis of saponins from black bean by electrospray ionization and fast atom bombardment tandem mass spectrometry
J Mass Spectrom 1999 Aug;34(8):804-12.PMID:10423561DOI:10.1002/(SICI)1096-9888(199908)34:8<804::AID-JMS835>3.0.CO;2-8.
Saponins from black bean (Vigna mungo L. Hepper) were analyzed using positive and negative ion fast atom bombardment mass spectrometry (FAB-MS) and liquid chromatography/mass spectrometry. Methanol was used to extract the saponins from defatted black bean, which was partially purified by extraction with n-butanol, and the extract was dialyzed with 3000 M(r) cut-off tubing. The dialyzate was analyzed using mass spectrometry. According to FAB-MS/MS, mixtures from black bean contain soyasaponin I as the predominant saponin. In addition, MS/MS analysis was performed in which the structures of saponins of black bean cotyledon were determined to be soyasaponin I, Soyasaponin II, soyasaponin V, 3-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl]complogenin (saponin A) and 3-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]oleanolic acid (saponin B). For the black bean shell and the root of black bean sprout, analysis confirmed the saponins of soyasaponin I, Soyasaponin II, soyasaponin V, saponin A, saponin B, acetylsoyasaponin A(4) and soyasaponin beta(g). Moreover, all the studied saponins were found in the stem and leaves of the black bean sprouts, except soyasaponin beta(g) and acetylsoyasaponin A(4), respectively.