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D1634

Sigma-Aldrich

Diosgenin

≥93%

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

Quality Level

200

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.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extraction of tannins and saponins from plant sources and their effects on in vitro methanogenesis and rumen fermentation
Yuliana P, et al.
Journal of the Indonesian Tropical Animal Agriculture, 39(2), 91-97 (2014)
Lijuan Wang et al.
Journal of natural products, 76(5), 909-914 (2013-04-30)
The purpose of this study was to investigate the ameliorating effect of dioscin (1) on multidrug resistance (MDR) in adriamycin (ADR)-resistant erythroleukemic cells (K562/adriamycin, K562/ADR) and to clarify the molecular mechanisms involved. High levels of multidrug resistance 1 (MDR1) mRNA
Jing Chen et al.
Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban, 36(6), 806-810 (2016-12-08)
This study investigated the effect of diosgenin, a natural sapogenin possessing various pharmacological activities, on benign prostatic hyperplasia (BPH) in rats and the possible mechanisms. BPH was established in the castrated rats by subcutaneous injection of testosterone propionate. Animals were
Shaofang Hua et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 1460-1465 (2016-11-05)
Gestational diabetes (GD) is a pathological condition, affecting 2-5% of pregnant women. Diosgenin (DSG) possesses a variety of biological activities. The present study was designed to examine the effect of DSG on GD and to investigate the possible mechanism in
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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