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Details

Stereochemistry ABSOLUTE
Molecular Formula C51H84O22
Molecular Weight 1049.2015
Optical Activity UNSPECIFIED
Defined Stereocenters 31 / 31
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTODIOSCIN

SMILES

C[C@]([H])(CC[C@@]1([C@@]([H])(C)[C@@]2([H])[C@]([H])(C[C@@]3([H])[C@]4([H])CC=C5C[C@]([H])(CC[C@]5(C)[C@@]4([H])CC[C@@]32C)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O6)O[C@@]7([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C)O7)O)O)O)O)O[C@@]8([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C)O8)O)O)O)O1)O)CO[C@@]9([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O9)O)O)O

InChI

InChIKey=LVTJOONKWUXEFR-UEZXSUPNSA-N
InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11988850 | https://www.ncbi.nlm.nih.gov/pubmed/12804079

Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, Trigonella and Dioscorea families. Extracts from T. terrestris standardised have been demonstrated to produce proerectile effects in isolated tissues and aphrodisiac action in several animal species. Protodioscin have shown cytotoxic effects against a number of leukemia and solid tumors cell lines.

Approval Year

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
Primary
FUROSAP

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.
2003 Apr
The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro.
2003 Jun
Total synthesis of methyl protodioscin: a potent agent with antitumor activity.
2003 May 2
Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.
2003 Oct 8
Furostanol saponins from Tribulus terrestris.
2003 Sep
Steroidal saponins from Dioscorea panthaica and their cytotoxic activity.
2004 Apr
Microbial metabolism of pseudoprotodioscin.
2004 Jul
Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.
2004 Jul 12
Methyl protodioscin induces G2/M arrest and apoptosis in K562 cells with the hyperpolarization of mitochondria.
2005 Jun 28
Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid.
2006 Jul
[Study on steroidal saponins of Dioscorea septemloba thunb].
2006 Nov
Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines.
2006 Sep
Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.
2006 Sep 8
Determination of protodioscin in rat plasma by liquid chromatography-tandem mass spectrometry.
2007 Apr 1
Distribution of steroidal saponins in Tribulus terrestris from different geographical regions.
2008 Jan
Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis C.H. Wright.
2010 Dec
[Effects of methyl protodioscin on [Ca2+]i and ATPase activity in cardiomyocytes and analysis of mechanisms].
2010 Jan
Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles.
2010 Jul 9
Qualitative and quantitative determination of major saponins in Paris and Trillium by HPLC-ELSD and HPLC-MS/MS.
2010 Nov 1
Development of a rapid HPLC-UV method for simultaneous quantification of protodioscin and rutin in white and green asparagus spears.
2010 Nov-Dec
Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica.
2010 Oct
Patents

Patents

Sample Use Guides

24 New Zealand white rabbits were divided randomly into four groups of six each. Group I served control and was treated with vehicle alone. Groups II, III, IV were treated with three different concentrations of Tribulus terrestris extracts (2.5, 5 and 10 mg/kg, respectively), orally for 8 weeks.
Route of Administration: Oral
Protodioscin was tested for cytotoxicity in vitro against 60 human cancer cell lines in the NCI's (National Cancer Institute, USA) anticancer drug screen.
Name Type Language
PROTODIOSCIN
Common Name English
PROTODIOSCIN [INCI]
Common Name English
PROTODIOSCIN [WHO-DD]
Common Name English
PROTODIOSCINE
Common Name English
26-O-.BETA.-D-GLUCOPYRANOSYL-(25R)-FUROST-5-ENE-3.BETA.,22.ALPHA.,26-TRIOL 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1-2)-(.ALPHA.-L-RHAMNOPYRANOSYL-(1-4))-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
3.BETA.,22.ALPHA.,26-TRIHYDROXYFUROST-5-ENE 3-O-.BETA.-CHACOTRIOSIDE 26-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-26-(.BETA.-D-GLUCOPYRANOSYLOXY)-22-HYDROXYFUROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-
Common Name English
Classification Tree Code System Code
DSLD 1157 (Number of products:8)
Created by admin on Sat Jun 26 08:34:24 UTC 2021 , Edited by admin on Sat Jun 26 08:34:24 UTC 2021
Code System Code Type Description
WIKIPEDIA
Protodioscin
Created by admin on Sat Jun 26 08:34:24 UTC 2021 , Edited by admin on Sat Jun 26 08:34:24 UTC 2021
PRIMARY
CAS
55056-80-9
Created by admin on Sat Jun 26 08:34:24 UTC 2021 , Edited by admin on Sat Jun 26 08:34:24 UTC 2021
PRIMARY
PUBCHEM
441891
Created by admin on Sat Jun 26 08:34:24 UTC 2021 , Edited by admin on Sat Jun 26 08:34:24 UTC 2021
PRIMARY
FDA UNII
D0LC3PH24P
Created by admin on Sat Jun 26 08:34:24 UTC 2021 , Edited by admin on Sat Jun 26 08:34:24 UTC 2021
PRIMARY