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D1634

Sigma-Aldrich

Diosgenin

≥93%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C27H42O3
Numéro CAS:
512-04-9
Poids moléculaire :
414.62
Numéro Beilstein :
94582
Numéro CE :
208-134-3
Numéro MDL:
MFCD00016887
Code UNSPSC :
12352200
ID de substance PubChem :
24893501
Nomenclature NACRES :
NA.77

Pureté

≥93%

Forme

powder

Chaîne SMILES 

[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

Clé InChI

WQLVFSAGQJTQCK-VKROHFNGSA-N

Informations sur le gène

human ... UGT1A4(54657)

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Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Antioxidative and hypolipidemic effects of diosgenin, a steroidal saponin of yam (Dioscorea spp.), on high-cholesterol fed rats
Son IS, et al.
Bioscience, Biotechnology, and Biochemistry, 71(12), 3063-3071 (2007)
Gautam Sethi et al.
Nutrients, 10(5) (2018-05-23)
Novel and alternative options are being adopted to combat the initiation and progression of human cancers. One of the approaches is the use of molecules isolated from traditional medicinal herbs, edible dietary plants and seeds that play a pivotal role
Chung-Hsiung Huang et al.
Journal of natural products, 73(6), 1033-1037 (2010-05-15)
It was hypothesized that the suppressive effect of diosgenin (1) on the intestinal T helper (Th)2 responses is associated with an enhancement of the regulatory T-cell immunity. Ovalbumin (OVA)-sensitized BALB/c mice were gavaged daily with 1 and received repeatedly oral
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
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
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