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Merck
CN

D1634

Sigma-Aldrich

Diosgenin

≥93%, apoptosis inducer, powder

Synonym(s):

(25R)-5-Spirosten-3β-ol, 3β-Hydroxy-5-spirostene, Nitogenin

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About This Item

Empirical Formula (Hill Notation):
C27H42O3
CAS Number:
512-04-9
Molecular Weight:
414.62
Beilstein:
94582
EC Number:
208-134-3
MDL number:
MFCD00016887
UNSPSC Code:
12352200
PubChem Substance ID:
24893501
NACRES:
NA.77

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Product Name

Diosgenin, ≥93%

Assay

≥93%

form

powder

SMILES string

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2

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-/m1/s1

InChI key

WQLVFSAGQJTQCK-VKROHFNGSA-N

Gene Information

human ... UGT1A4(54657)

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General description

Diosgenin is a triterpene and a glycone derivative of dioscin. Yams, Trigonella foenum-graecum and Costus speciosus are some of its source.

Application

Diosgenin has been:
  • used as a standard in the analysis of total saponins in Sapindus rarak
  • orally administered to the rats to study its role against atherogenic diet-induced production of inflammatory mediators in heart, liver and brain
  • used as a standard compound to determine the saponins content in chickpea and Tribulus terrestris

Biochem/physiol Actions

Diosgenin induces apoptosis in colon cancer cell lines and induces apoptosis, cell cycle arrest and cyclooxygenase activity in osteosarcoma cells. It serves as a precursor in steroid drug production. Diosgenin is shown to promote cholesterol production by stimulating biliary excretion. It influences lipoxygenase induced human erythroleukemia cell line differentiation.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000495746
0000495746
0000493068
0000493068
0000492996

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Won Seok Yang et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 43(6), 2434-2445 (2017-10-27)
We investigated how diosgenin, a steroidal sapogenin, has anti-tumor necrosis factor-α (TNF-α) effects in human aortic endothelial cells (HAECs). Tumor necrosis factor receptor 1 (TNFR1) was assessed by Western blot analysis. Intracellular Ca2+ was measured using Fluo-4 AM. Immunofluorescence staining
Fatemeh Ganjeizadeh Rohani et al.
Journal of pharmaceutical and biomedical analysis, 174, 552-560 (2019-07-01)
A novel electropolymerized molecularly imprinted polymer (MIP) film, based on diosgenin on a glassy carbon electrode (GCE), has been synthesized. Based on density functional theory (DFT), para-aminobenzoic acid (pABA), which is a green substance, was selected from five functional monomers
Atherogenic diet induced lipid accumulation induced NFkappaB level in heart, liver and brain of Wistar rat and diosgenin as an anti-inflammatory agent
Binesh A, et al.
Life Sciences, 196, 28-37 (2018)
Diosgenin induces cell cycle arrest and apoptosis in human leukemia K562 cells with the disruption of Ca 2+ homeostasis
Liu MJ, et al.
Cancer Chemotherapy and Pharmacology, 55(1), 79-90 (2005)
Andreas Blees et al.
Nature, 551(7681), 525-528 (2017-11-07)
The peptide-loading complex (PLC) is a transient, multisubunit membrane complex in the endoplasmic reticulum that is essential for establishing a hierarchical immune response. The PLC coordinates peptide translocation into the endoplasmic reticulum with loading and editing of major histocompatibility complex
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