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Yamogenin Sale

(Synonyms: 雅姆皂甙元; Neodiosgenin) 目录号 : GC39535

A steroidal sapogenin with diverse biological activities

Yamogenin Chemical Structure

Cas No.:512-06-1

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10mM (in 1mL DMSO)
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产品描述

Yamogenin is a steroidal sapogenin that has been found in fenugreek (T. foenum graecum) and has diverse biological activities.1,2 It inhibits activation of the liver X receptor (LXR) induced by the LXRα and LXRβ agonist T0901317 in HepG2 cells in a reporter assay when used at concentrations of 5 or 10 ?M.1 Yamogenin (10 ?M) decreases triglyceride levels in primary mouse hepatocytes. It is cytotoxic to HaCaT keratinocytes, as well as HeLa cervical and SKOV3 ovarian cancer cells (IC50s = 16.4, 19.6, and 23.9 ?g/ml, respectively).2

1.Moriwaki, S., Murakami, H., Takahashi, N., et al.Yamogenin in fenugreek inhibits lipid accumulation through the suppression of gene expression in fatty acid synthesis in hepatocytesBiosci. Biotechnol. Biochem.78(7)1231-1236(2014) 2.Stefanowicz-Hajduk, J., Kól-Kogus, B., Sparzak-Stefanowska, B., et al.Cytotoxic activity of standardized extracts, a fraction, and individual secondary metabolites from fenugreek seeds against SKOV-3, HeLa and MOLT-4 cell linesPharm. Biol.59(1)424-437(2021)

Chemical Properties

Cas No. 512-06-1 SDF
别名 雅姆皂甙元; Neodiosgenin
Canonical SMILES [H][C@]1(O[C@@]2(OC[C@@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]
分子式 C27H42O3 分子量 414.62
溶解度 Ethanol: 10 mg/mL (24.12 mM) 储存条件 Store at -20°C
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5 mM 0.4824 mL 2.4118 mL 4.8237 mL
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Research Update

Yamogenin-Induced Cell Cycle Arrest, Oxidative Stress, and Apoptosis in Human Ovarian Cancer Cell Line

Molecules 2022 Nov 24;27(23):8181.PMID:36500274DOI:10.3390/molecules27238181.

Steroidal saponins are a group of compounds with complex structures and biological activities. They have anti-inflammatory, antimicrobial, fungicidal, and antitumor properties. Yamogenin is one of the spirostane saponins and occurs in Trigonella foenum-graecum, Asparagus officinalis, and Dioscorea collettii. It is a stereoisomer of diosgenin-a well-known compound whose activity and mechanisms of action in cancer cells are determined. However, the antitumor effect of Yamogenin is still little known, and the mechanism of action has not been determined. In this study, we evaluated the effect of Yamogenin on human ovarian cancer SKOV-3 cells in vitro by determining the cellular factors that trigger cell death. The viability of the cells was assessed with a Real-Time xCELLigence system and the cell cycle arrest with flow cytometry. The activity of initiator and executioner caspases (-8, -9, and -3/7) was estimated with luminometry and flow cytometry, respectively. The mitochondrial membrane depolarization, the level of oxidative stress, and DNA damage in the yamogenin-treated cells were also evaluated by flow cytometry. Genes expression analysis at the mRNA level was conducted with Real-Time PCR. Bid activation and chromatin condensation were estimated with fluorescent microscopy. The obtained results indicate that Yamogenin has cytotoxic activity in SKOV-3 cells with an IC50 value of 23.90 ± 1.48 µg/mL and strongly inhibits the cell cycle in the sub-G1 phase. The compound also triggers cell death with a significant decrease in mitochondrial membrane potential, an increase in the level of oxidative stress (over two times higher in comparison to the control), and activation of caspase-8, -9, -3/7, as well as Bid. The results of genes expression indicate that the Tumor Necrosis Factor (TNF) Receptor Superfamily Members (TNF, TNFRSF10, TNFRSF10B, TNFRSF1B, and TNFRSF25), Fas Associated via Death Domain (FADD), and Death Effector Domain Containing 2 (DEDD2) were significantly upregulated and their relative expression was at least two times higher than in the control. Our work shows that Yamogenin induces apoptosis in ovarian cancer cells, and both the extrinsic and mitochondrial-intrinsic pathways are involved in this process.

Yamogenin in fenugreek inhibits lipid accumulation through the suppression of gene expression in fatty acid synthesis in hepatocytes

Biosci Biotechnol Biochem 2014;78(7):1231-6.PMID:25229863DOI:10.1080/09168451.2014.915736.

Yamogenin is a diastereomer of diosgenin, which we have identified as the compound responsible for the anti-hyperlipidemic effect of fenugreek. Here, we examined the effects of Yamogenin on the accumulation of triacylglyceride (TG) in hepatocytes, because Yamogenin is also contained in fenugreek. It was demonstrated that Yamogenin also inhibited TG accumulation in HepG2 hepatocytes and suppressed the mRNA expression of fatty acid synthesis-related genes such as fatty acid synthase and sterol response element-binding protein-1c. Indeed, Yamogenin also antagonized the activation of the liver X receptor (LXR) in luciferase ligand assay similar to diosgenin. However, Yamogenin could not exert such effects in the presence of T0901713, a potent agonist of LXR. These findings indicate that the effects of Yamogenin on TG accumulation would be weaker than those of diosgenin, suggesting that the structural difference between Yamogenin and diosgenin would be important for the inhibition of LXR activation.

Steroid Alkaloids and Yamogenin from Solanum spirale1

Planta Med 1987 Jun;53(3):292-3.PMID:17269026DOI:10.1055/s-2006-962711.

Tomatidenol, 15alpha-hydroxytomatidenol, and Yamogenin were isolated from the leaves, and etioline from the roots of SOLANUM SPIRALE.

Cytotoxic steroidal saponins from Panicum turgidum Forssk

Steroids 2017 Sep;125:14-19.PMID:28629616DOI:10.1016/j.steroids.2017.06.003.

Three new bidesmosidic cholestane-type steroidal glycosides, 16-O-β-d-glucopyranosyl-cholest-5-en-3β,16β-diol-22-one-3-O-α-l-rhamnopyranosyl-(1→2)-O-[(β-d-glucopyranosyl(1→4)]-O-β-d-glucopyranoside (1), 16-O-β-d-glucopyranosylcholest-5-en-3β,16β-diol-22-one-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranoside (2), and 16-O-β-d-glucopyranosylcholestan-3β,16β-diol-6,22-dione-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranoside (3) were isolated from a methanolic extract of Panicum turgidum. In addition four known compounds, pennogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)-O-α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (4), Yamogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (5), Yamogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)-O-α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (6), and pennogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (7) were also isolated and characterized. Their structures were established using extensive spectroscopic methods including 1D and 2D NMR and HRESIMS. The isolated compounds were screened for cytotoxicity towards a panel of mammalian cell lines and 4-7 were found to be cytotoxic.

Steroidal Sapogenins in Dioscorea collettii

Planta Med 1983 Sep;49(9):38-42.PMID:17405009DOI:10.1055/s-2007-969807.

Ten Steroidal compounds were isolated from the acid-treated rhizome of wild DIOSCOREA COLLETTII collected from Sichuan province, China. Five of them were identified as diosgenin ( 1), Yamogenin ( 2), beta-sitosterol ( 3), Delta (3,5)-deoxytigogenin ( 5) and isonarthogenin ( 9). The other four compounds have not been reported previously in the literature and their structures have been elucidated by spectroscopic data and chemical transformation. They are Delta (3,5)-deoxyneotigogenin ( 6), diosgenin palmitate ( 7), Yamogenin palmitate ( 8) and yamogenin-beta-D-glucoside ( 10). It is of interest to note that three pairs of C (25) isomers were isolated: 1 and 2,5 and 6,7 and 8, apparently as artefacts due to the acid treatment. The structure of dihydroxysterol ( 4) is still to be determined.