U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42O3
Molecular Weight 414.6216
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSGENIN

SMILES

C[C@]1([H])CC[C@@]2([C@@]([H])(C)[C@@]3([H])[C@]([H])(C[C@@]4([H])[C@]5([H])CC=C6C[C@]([H])(CC[C@]6(C)[C@@]5([H])CC[C@@]43C)O)O2)OC1

InChI

InChIKey=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

HIDE SMILES / InChI

Molecular Formula C27H42O3
Molecular Weight 414.6216
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12724917 https://www.ncbi.nlm.nih.gov/pubmed/26222585

Diosgenin is a major bioactive constituent of various edible pulses and roots, well characterized in the seeds of fenugreek as well as in the root tubers of wild yams. The findings from pre-clinical and mechanistic studies strongly implicate the use of diosgenin as a novel multi-target based chemo preventive or therapeutic agent against several chronic diseases. Diosgenin has been shown to increase cholesterol secretion fiveto seven-fold in the bile of rats without altering the output of bile salts and phospholipids (Kosters et al., 2005; Nervi et al., 1988; Nibbering et al., 2001). Recently, it was shown that the biliary cholesterol secretion stimulated by diosgenin and leading to fecal cholesterol excretion is independent of intestinal cholesterol absorption. The anti-cancer effects of diosgenin in vitro through different mechanisms was investigated and was shown that it could use in the treatment Colon cancer, breast cancer, prostate cancer and some others. Also was investigates the effect of diosgenin on hepatitis C virus (HCV) replication and was shown that compound can inhibits HCV replication at low µM concentrations. Diosgenin was able to protect the kidney from morphological changes associated with ovariectomy. The mechanism is responsible for this protection was the conversion of diosgenin to progesterone. The extensive pre-clinical and clinical research should be carried out prior to advocating the safe and efficacious use of diosgenin and diosgenin-rich plant extracts against the prevention and control of diseases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9WTN3
Gene ID: 20787.0
Gene Symbol: Srebf1
Target Organism: Mus musculus (Mouse)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Isolation and identification of steroidal saponins in total saponin from Dioscorea nipponica Makino].
2002 Apr
Studies toward the synthesis of the shark repellent pavoninin-5.
2002 Dec
[Comparative study on anti-hypercholesterolemia activity of diosgenin and total saponin of Dioscorea panthaica].
2002 Jul
[Advances in the study of Paris L. and its uses].
2002 Mar
[The antitumor activity of Diosgenin in vivo and in vitro].
2002 Oct
[Intestinal bacteria metabolism of TSDP and characterization of metabolites in rats].
2002 Sep
[Study on chemical constituents of rhizome of Anemone raddeana].
2002 Sep
Structural changes in the kidney associated with ovariectomy and diosgenin replacement therapy in adult female rats.
2003
The effects of sustained delivery of diosgenin on the adrenal gland of female rats.
2003
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.
2003 Apr
Different contribution of apoptosis to the antiproliferative effects of diosgenin and other plant steroids, hecogenin and tigogenin, on human 1547 osteosarcoma cells.
2003 Apr
Structural features of sterols required to inhibit human sperm capacitation.
2003 Apr
The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides.
2003 Apr 4
In vitro micropropagation, differentiation of aerial bulbils and tubers and diosgenin content in Dioscorea bulbifera.
2003 Aug
Regulation of biliary cholesterol secretion is associated with abcg5 and abcg8 expressions in the rats: effects of diosgenin and ethinyl estradiol.
2003 Aug
[Apoptosis of human chronic myeloid leukemia k562 cell induced by prosapogenin B of dioscin (P.B) in vitro].
2003 Aug
Synthesis of rhamnosylated diosgenyl glucosides as mimetics of cytostatic steroidal saponins from Ornithogalum saindersiae and Galtonia candicans.
2003 Dec 21
Regioselective cleavage of rings E and F in sarsasapogenin.
2003 Feb
Ovine metabolism of diosgenin coated on cellulose in relation to hepatogenous photosensitization of ruminants.
2003 Feb
Biological activities of synthetic saponins and cardiac glycosides.
2003 Jan
[Sports and doping].
2003 Jul
Anti-obesity effect of Dioscorea nipponica Makino with lipase-inhibitory activity in rodents.
2003 Jul
The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro.
2003 Jun
Relation between hepatic expression of ATP-binding cassette transporters G5 and G8 and biliary cholesterol secretion in mice.
2003 Jun
Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol- or indomethacin-induced gastric mucosal lesions in rats: structural requirement for activity and mode of action.
2003 Mar 24
Solanidine hydrolytic extraction and separation from the potato (Solanum tuberosum L.) vines by using solid-liquid-liquid systems.
2003 Mar 26
Genetic stability assessment of plants regenerated from cryopreserved embryogenic tissues of Dioscorea bulbifera l. Using RAPD, biochemical and morphological analysis.
2003 Mar-Apr
[Advances in the study on Dioscorea zingiberensis C.H. Wright].
2003 May
Total synthesis of methyl protodioscin: a potent agent with antitumor activity.
2003 May 2
Isolation and identification of steroidal saponins in Taiwanese yam cultivar (Dioscorea pseudojaponica Yamamoto).
2003 Oct 22
Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.
2003 Oct 8
Furostanol saponins from Tribulus terrestris.
2003 Sep
Diosgenin, a plant steroid, induces apoptosis in human rheumatoid arthritis synoviocytes with cyclooxygenase-2 overexpression.
2004
Diosgenin induces apoptosis in HeLa cells via activation of caspase pathway.
2004 Aug
Diosgenin, a steroid saponin of Trigonella foenum graecum (Fenugreek), inhibits azoxymethane-induced aberrant crypt foci formation in F344 rats and induces apoptosis in HT-29 human colon cancer cells.
2004 Aug
Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol.
2004 Dec
Supercritical fluid extraction of sapogenins from tubers of Smilax china.
2004 Dec
Diosgenin dose-dependent apoptosis and differentiation induction in human erythroleukemia cell line and sedimentation field-flow fractionation monitoring.
2004 Dec 15
Antifungal steroid saponins from Dioscorea cayenensis.
2004 Jan
Alpha-hydroxylation at C-15 and C-16 in cholesterol: synthesis of (25R)-5alpha-cholesta-3beta,15alpha,26-triol and (25R)-5alpha-cholesta-3beta,16alpha,26-triol from diosgenin.
2004 Jan 22
Microbial metabolism of pseudoprotodioscin.
2004 Jul
Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.
2004 Jul 12
[Studies on the dynamic trends of diosgenin content in vegetative organs of Dioscorea zingiberensis].
2004 Jun
Induction of antiproliferative effect by diosgenin through activation of p53, release of apoptosis-inducing factor (AIF) and modulation of caspase-3 activity in different human cancer cells.
2004 Jun
In vivo antiosteoporotic activity of a fraction of Dioscorea spongiosa and its constituent, 22-O-methylprotodioscin.
2004 Mar
A mouse model of sitosterolemia: absence of Abcg8/sterolin-2 results in failure to secrete biliary cholesterol.
2004 Mar 24
Cytotoxicity of the phytosterol diosgenin and its derivatives in rat cultured hepatocytes and V79 fibroblasts.
2004 Oct
Phytochemical analysis and anti-allergic study of Agave intermixta Trel. and Cissus sicyoides L.
2004 Sep
Effects of steroidal glycoalkaloids from potatoes (Solanum tuberosum) on in vitro bovine embryo development.
2005 Feb
Expression of ABCG5 and ABCG8 is required for regulation of biliary cholesterol secretion.
2005 Mar 11
Patents

Sample Use Guides

in rats: Animals were randomly divided into four groups (n=10 each): model group (0.5% sodium carboxymethyl cellulose); positive control group (3 mg/kg finasteride); two diosgenin groups (50 and 100 mg/kg). The drugs were intragastricaly given in each group for consecutive 3 weeks.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment:: In vitro experiments were performed to investigate the inhibitory activity of diosgenin on human breast cancer MDA-MB-231 cell migration. Diosgenin caused a marked inhibition of cell migration in MDA-MB-231 cell by transwell assay. Also was found diosgenin significantly inhibited actin polymerization, Vav2 phosphorylation and Cdc42 activation, which might be, at least in part, attributed to the anti-metastatic potential of diosgenin
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:41:09 UTC 2021
Edited
by admin
on Sat Jun 26 00:41:09 UTC 2021
Record UNII
K49P2K8WLX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSGENIN
INCI   MI  
INCI  
Official Name English
DIOSGENIN [MI]
Common Name English
(3.BETA.,25R)-SPIROST-5-EN-3-OL
Systematic Name English
DIOSGENIN [WHO-DD]
Common Name English
NSC-33396
Code English
DIOSGENIN [INCI]
Common Name English
DIOSGENIN (CONSTITUENT OF FENUGREEK SEED) [DSC]
Common Name English
NITOGENIN
Common Name English
Classification Tree Code System Code
DSLD 1360 (Number of products:3)
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
Code System Code Type Description
MESH
D004144
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
FDA UNII
K49P2K8WLX
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
MERCK INDEX
M4593
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY Merck Index
PUBCHEM
99474
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
WIKIPEDIA
DIOSGENIN
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
CAS
512-04-9
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-134-3
Created by admin on Sat Jun 26 00:41:09 UTC 2021 , Edited by admin on Sat Jun 26 00:41:09 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY