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Details

Stereochemistry ABSOLUTE
Molecular Formula C51H84O22
Molecular Weight 1049.1995
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(O)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]2[C@@H]1C)O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)CO[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O

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

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
PubMed

PubMed

TitleDatePubMed
Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.
2001 Nov
Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.
2002 Apr
Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.
2002 Aug 9
Two new sulfated furostanol saponins from Tribulus terrestris.
2002 Jan-Feb
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.
2003 Apr
Protodioscin isolated from fenugreek (Trigonella foenumgraecum L.) induces cell death and morphological change indicative of apoptosis in leukemic cell line H-60, but not in gastric cancer cell line KATO III.
2003 Jan
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
The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat.
2008 Jan
Distribution of steroidal saponins in Tribulus terrestris from different geographical regions.
2008 Jan
Steroidal saponins from Smilax excelsa rhizomes.
2009
A new spirostanol glycoside from fruits of Solanum indicum L.
2009 Jul
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
Pharmacokinetics of methyl protodioscin in rats.
2010 May
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

In Vivo Use Guide
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
In Vitro Use Guide
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 [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
Code System Code Type Description
WIKIPEDIA
Protodioscin
Created by admin on Mon Oct 21 20:12:03 UTC 2019 , Edited by admin on Mon Oct 21 20:12:03 UTC 2019
PRIMARY
CAS
55056-80-9
Created by admin on Mon Oct 21 20:12:03 UTC 2019 , Edited by admin on Mon Oct 21 20:12:03 UTC 2019
PRIMARY
PUBCHEM
441891
Created by admin on Mon Oct 21 20:12:03 UTC 2019 , Edited by admin on Mon Oct 21 20:12:03 UTC 2019
PRIMARY