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Structure Database (LMSD)

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Common Name

Yamogenin

Systematic Name

(25S)-spirost-5-en-3β-ol

Synonyms

LM ID

LMST01080045

Formula

C₂₇H₄₂O₃

Exact Mass

Calculate m/z

414.313395

Sum Composition

ST 27:3;O3

Status

Curated

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Classification

Biological Context

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 µM.¹ Yamogenin (10 µM) 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 µg/ml, respectively).²

This information has been provided by Cayman Chemical

References

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 hepatocytes. Biosci. 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 lines. Pharm. Biol. 59(1), 424-437 (2021).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Smilax aspera (#59116)

Magnoliopsida (#3398)

Steroid saponins,
Phytochemistry, 1982

DOI: 10.1016/S0031-9422(00)82400-0

String Representations

InChiKey (Click to copy)

WQLVFSAGQJTQCK-CAKNJAFZSA-N

InChi (Click to copy)

InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

SMILES (Click to copy)

C1[C@H](O)CC2[C@@](C)([C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC=2)CC[C@H](C)CO6)C)C1