Diosgenin

Names

[ CAS No. ]:
512-04-9

[ Name ]:
Diosgenin

[Synonym ]:
EINECS 208-134-3
3β-Hydroxy-5-spirostene
Diosgenin
(25R)-5-Spirosten-3β-ol
MFCD00016887
DELTA 5,20A,22A,25D-SPIROSTEN-3BETA-OL

Biological Activity

[Description]:

Diosgenin, a steroidal saponin, can inhibit STAT3 signaling pathway.

[Related Catalog]:

Research Areas >> Metabolic Disease

Natural Products >> Steroids

[Target]

STAT3

[In Vitro]

In MC65 cells, a cellular AD model, diosgenin exhibited weak protective abilities at 1 μM, may represent a good candidate as a steroidal moiety in our bivalent compounds against AD pathology[1]. Diosgenin inhibits the constitutive activation of STAT3 in C3A cells in a dose-dependent manner, with maximum inhibition occurring at around 100 μM[2].

[In Vivo]

Diosgenin treatment significantly reduces fasted and refed blood glucose level in HF dietfed mice. Diosgenin treatment significantly reduces blood glucose level in IPGTT test, compared with that of HF diet-fed mice[3].

[References]

[1]. Jeremy E. Chojnacki, et al. Bivalent ligands incorporating curcumin and diosgenin asmultifunctional compounds against Alzheimer’s disease. Bioorganic & Medicinal Chemistry, 23 (2015) 7324–7331

[2]. Li F, et al. Diosgenin, a steroidal saponin, inhibits STAT3 signaling pathway leading to suppression of proliferation and chemosensitization of human hepatocellular carcinoma cells. Cancer Lett. 2010 Jun 28;292(2):197-207.

[3]. Wang X, et al. Effect of diosgenin on metabolic dysfunction: Role of ERβ in the regulation of PPARγ. Toxicol Appl Pharmacol. 2015 Dec 1;289(2):286-96.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
527.1±50.0 °C at 760 mmHg

[ Melting Point ]:
205-208°C

[ Molecular Formula ]:
C₂₇H₄₂O₃

[ Molecular Weight ]:
414.621

[ Flash Point ]:
272.6±30.1 °C

[ Exact Mass ]:
414.313385

[ PSA ]:
38.69000

[ LogP ]:
5.84

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.564

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
chloroform: 20 mg/mL, clear, slightly yellow

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WH1450000

CHEMICAL NAME :: Spirost-5-en-3-beta-ol, (25R)-

CAS REGISTRY NUMBER :: 512-04-9

BEILSTEIN REFERENCE NO. :: 0094582

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C27-H42-O3

MOLECULAR WEIGHT :: 414.69

WISWESSER LINE NOTATION :: T F5 E5 B666 HXO OUTJ A1 E1 G1 RQ H-& BT6OXTJ E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4872 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay)

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay)

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3564 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay)

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
WH1450000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Diosgenin-based thio(seleno)ureas and triazolyl glycoconjugates as hybrid drugs. Antioxidant and antiproliferative profile.

Eur. J. Med. Chem. 99 , 67-81, (2015)

The stereoselective preparation of diosgenin-derived thio(seleno)ureas and glycomimetics bearing a 1,2,3-triazolyl tether on C-3 has been accomplished. The key steps in the synthetic pathway are the i...

In Vivo Protective Effects of Diosgenin against Doxorubicin-Induced Cardiotoxicity.

Nutrients 7 , 4938-54, (2015)

Doxorubicin (DOX) induces oxidative stress leading to cardiotoxicity. Diosgenin, a steroidal saponin of Dioscorea opposita, has been reported to have antioxidant activity. Our study was aimed to find ...

The Chinese herb polyphyllin D sensitizes ovarian cancer cells to cisplatin-induced growth arrest.

J. Cancer Res. Clin. Oncol. 141(2) , 237-42, (2015)

We evaluated the effects of polyphyllin D (PD), a natural compound with anti-neoplastic activity and a major component of the Chinese herb Paris polyphylla, on ovarian cancer (OVCA) cell line prolifer...

Related Compounds

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