PROTODIOSCIN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18068966
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

Condition	Modality	Highest Phase	Product
Erectile dysfunction 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18068966	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 82 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Renal cancer 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Colon cancer 61 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 195 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Hypogonadism 28 Sources: https://clinicaltrials.gov/ct2/show/NCT02702882	Primary	Approved 8043	FUROSAP Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.	2001 Nov	11745732
Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.	2002 Apr	11988850
Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.	2002 Aug 9	12127159
Two new sulfated furostanol saponins from Tribulus terrestris.	2002 Jan-Feb	11926540
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.	2003 Apr	12804079
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	12469212
The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro.	2003 Jun	12901285
Total synthesis of methyl protodioscin: a potent agent with antitumor activity.	2003 May 2	12713375
Steroidal saponins from Dioscorea panthaica and their cytotoxic activity.	2004 Apr	15125576
Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid.	2006 Jul	16713252
Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines.	2006 Sep	16797625
Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.	2006 Sep 8	16458429
Determination of protodioscin in rat plasma by liquid chromatography-tandem mass spectrometry.	2007 Apr 1	17251071
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	18068966
Steroidal saponins from Smilax excelsa rhizomes.	2009	19521905
A new spirostanol glycoside from fruits of Solanum indicum L.	2009 Jul	19571425
Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis C.H. Wright.	2010 Dec	20659537
[Effects of methyl protodioscin on [Ca2+]i and ATPase activity in cardiomyocytes and analysis of mechanisms].	2010 Jan	20349722
Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles.	2010 Jul 9	20627255
Pharmacokinetics of methyl protodioscin in rats.	2010 May	20503929
Qualitative and quantitative determination of major saponins in Paris and Trillium by HPLC-ELSD and HPLC-MS/MS.	2010 Nov 1	20870470
Development of a rapid HPLC-UV method for simultaneous quantification of protodioscin and rutin in white and green asparagus spears.	2010 Nov-Dec	21535581
Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica.	2010 Oct	20509104

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 [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)