PROTODIOSCIN

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 Search

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

Molecular Formula	C51H84O22
Molecular Weight	1049.1995
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	31 / 31
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18068966	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 72 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 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11988850	Primary	Basic research	Unknown Approved Use Unknown
Hypogonadism 29 Sources: https://clinicaltrials.gov/ct2/show/NCT02702882	Primary	Approved 8583	FUROSAP Approved Use Unknown

PubMed

Title	Date	PubMed
Development of a rapid HPLC-UV method for simultaneous quantification of protodioscin and rutin in white and green asparagus spears.	2011-05-04	21535581
Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis C.H. Wright.	2010-12	20659537
Qualitative and quantitative determination of major saponins in Paris and Trillium by HPLC-ELSD and HPLC-MS/MS.	2010-11-01	20870470
Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica.	2010-10	20509104
Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles.	2010-07-09	20627255
Pharmacokinetics of methyl protodioscin in rats.	2010-05	20503929
[Effects of methyl protodioscin on [Ca2+]i and ATPase activity in cardiomyocytes and analysis of mechanisms].	2010-01	20349722
A new spirostanol glycoside from fruits of Solanum indicum L.	2009-07	19571425
Steroidal saponins from Smilax excelsa rhizomes.	2009	19521905
The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat.	2008-01	18068966
Distribution of steroidal saponins in Tribulus terrestris from different geographical regions.	2008-01	17719068
Determination of protodioscin in rat plasma by liquid chromatography-tandem mass spectrometry.	2007-04-01	17251071
[Study on steroidal saponins of Dioscorea septemloba thunb].	2006-11	17228658
Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.	2006-09-08	16458429
Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines.	2006-09	16797625
Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid.	2006-07	16713252
Methyl protodioscin induces G2/M arrest and apoptosis in K562 cells with the hyperpolarization of mitochondria.	2005-06-28	15914274
Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.	2004-07-12	15220085
Microbial metabolism of pseudoprotodioscin.	2004-07	15254856
Steroidal saponins from Dioscorea panthaica and their cytotoxic activity.	2004-04	15125576
Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.	2003-10-08	14518934
Furostanol saponins from Tribulus terrestris.	2003-09	12946722
The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro.	2003-06	12901285
Total synthesis of methyl protodioscin: a potent agent with antitumor activity.	2003-05-02	12713375
Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.	2003-04	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.	2003-01	12469212
Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.	2002-08-09	12127159
Two new sulfated furostanol saponins from Tribulus terrestris.	2002-04-03	11926540
Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.	2002-04	11988850
Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.	2001-11	11745732

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:03:33 GMT 2025` Edited by `admin` on `Mon Mar 31 19:03:33 GMT 2025`
Record UNII	D0LC3PH24P
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PROTODIOSCIN

Official 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))-

Preferred 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

Protodioscin [WHO-DD]

Common Name

English

Classification Tree Code System Code

DSLD

1157 (Number of products:8)