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Merck
CN

D1634

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
NACRES:
NA.77
PubChem Substance ID:
24893501
UNSPSC Code:
12352200
EC Number:
208-134-3
MDL number:
MFCD00016887
Beilstein/REAXYS Number:
94582

Key Documents

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Product Name

Diosgenin, ≥93%

InChI key

WQLVFSAGQJTQCK-VKROHFNGSA-N

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

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

assay

≥93%

form

powder

Quality Level

200

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

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000495746
0000495746
0000493068
0000493068
0000492996

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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
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)
Anuraga Jayanegara et al.
Animals : an open access journal from MDPI, 10(9) (2020-09-03)
The objective of this experiment was to test the effects of combining plant extracts rich in tannins and saponins at varying proportions on in vitro ruminal methane and ammonia formation. Tannins were extracted from Swietenia mahogani leaves and saponins from
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.
International immunopharmacology, 42, 59-66 (2016-11-26)
Although the development of T helper (Th)1-like regulatory T (Treg) cells under Th1 inflammatory conditions has been reported, the role of Th1-like Treg cells in Th2 allergic responses remains mostly unclear. We previously demonstrated that diosgenin, the major sapogenin contained
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