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Key Documents

D1634

Sigma-Aldrich

Diosgenin

≥93%

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C27H42O3
Número CAS:
Peso molecular:
414.62
Beilstein:
94582
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

Ensaio

≥93%

forma

powder

cadeia de caracteres 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

chave InChI

WQLVFSAGQJTQCK-VKROHFNGSA-N

Informações sobre genes

human ... UGT1A4(54657)

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Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Hecogenin phyproof® Reference Substance

PHL83508

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Protodioscin from Dioscorea spp., ≥98% (HPLC)

Sigma-Aldrich

G0299

Protodioscin

Tigogenin phyproof® Reference Substance

PHL83916

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Ruscogenin ≥98% (HPLC)

Sigma-Aldrich

SMB00295

Ruscogenin

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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