Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H42O3 |
Molecular Weight | 414.6206 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
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
Molecular Formula | C27H42O3 |
Molecular Weight | 414.6206 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://cdn.intechopen.com/pdfs-wm/25787.pdfCurator'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
Sources: http://cdn.intechopen.com/pdfs-wm/25787.pdf
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q9WTN3 Gene ID: 20787.0 Gene Symbol: Srebf1 Target Organism: Mus musculus (Mouse) Sources: http://www.uniprot.org/uniprot/Q9WTN3 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
C-27 and C-3 glucosylation of diosgenin by cell suspension cultures of Costus speciosus. | 2001 |
|
The prevention of osteoporotic progression by means of steroid loaded TCPL drug delivery systems. | 2001 |
|
13C cross-polarization MAS NMR study of some steroidal sapogenins. | 2001 Aug-Sep |
|
Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. | 2001 Feb |
|
Effects of two saponins extracted from the polygonatum Zanlanscianense pamp on the human leukemia (HL-60) cells. | 2001 Feb |
|
An improved synthesis of the saponin, polyphyllin D. | 2001 Mar 9 |
|
A plant steroid, diosgenin, induces apoptosis, cell cycle arrest and COX activity in osteosarcoma cells. | 2001 Oct 12 |
|
[Isolation and identification of steroidal saponins in total saponin from Dioscorea nipponica Makino]. | 2002 Apr |
|
Preparations of heterospirostanols and their pharmacological activities. | 2002 Aug |
|
Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and xiebai saponin I. | 2002 Dec 13 |
|
Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests. | 2002 Jun |
|
A facile approach to diosgenin and furostan type saponins bearing a 3beta-chacotriose moiety. | 2002 Nov 19 |
|
[The antitumor activity of Diosgenin in vivo and in vitro]. | 2002 Oct |
|
[Study on hydrolysis conditions of Dioscorea nipponica with uniform design method]. | 2002 Sep |
|
Low temperature crystal structure of natural diosgenone. | 2002 Sep-Oct |
|
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model. | 2003 Apr |
|
Structural features of sterols required to inhibit human sperm capacitation. | 2003 Apr |
|
Relation between hepatic expression of ATP-binding cassette transporters G5 and G8 and biliary cholesterol secretion in mice. | 2003 Jun |
|
Solanidine hydrolytic extraction and separation from the potato (Solanum tuberosum L.) vines by using solid-liquid-liquid systems. | 2003 Mar 26 |
|
Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors. | 2004 Aug 6 |
|
Diosgenin dose-dependent apoptosis and differentiation induction in human erythroleukemia cell line and sedimentation field-flow fractionation monitoring. | 2004 Dec 15 |
|
[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 |
|
Diosgenin-3-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranoside obtained as a new anticancer agent from Dioscorea futschauensis induces apoptosis on human colon carcinoma HCT-15 cells via mitochondria-controlled apoptotic pathway. | 2004 Jun |
|
In vivo antiosteoporotic activity of a fraction of Dioscorea spongiosa and its constituent, 22-O-methylprotodioscin. | 2004 Mar |
|
Expression of ABCG5 and ABCG8 is required for regulation of biliary cholesterol secretion. | 2005 Mar 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27924509
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24656238
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
Edited
Fri Dec 15 15:17:42 GMT 2023
by
admin
on
Fri Dec 15 15:17:42 GMT 2023
|
Record UNII |
K49P2K8WLX
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DSLD |
1360 (Number of products:3)
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
D004144
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
K49P2K8WLX
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
33396
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
m4593
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | Merck Index | ||
|
99474
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
DIOSGENIN
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
4629
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
512-04-9
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
208-134-3
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY | |||
|
DTXSID00895074
Created by
admin on Fri Dec 15 15:17:42 GMT 2023 , Edited by admin on Fri Dec 15 15:17:42 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |