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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

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@](O)(CC[C@@H](C)CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O2)O[C@]7([H])O[C@H](CO)[C@@H](O[C@]8([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@]9([H])O[C@@H](C)[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
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
Total synthesis of methyl protodioscin: a potent agent with antitumor activity.
2003 May 2
Microbial metabolism of pseudoprotodioscin.
2004 Jul
Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.
2004 Jul 12
Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid.
2006 Jul
Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.
2006 Sep 8
Development of a rapid HPLC-UV method for simultaneous quantification of protodioscin and rutin in white and green asparagus spears.
2010 Nov-Dec
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
INCI  
Official Name English
PROTODIOSCIN [INCI]
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
Protodioscin [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 1157 (Number of products:8)
Created by admin on Fri Dec 15 18:07:46 UTC 2023 , Edited by admin on Fri Dec 15 18:07:46 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID901021361
Created by admin on Fri Dec 15 18:07:47 UTC 2023 , Edited by admin on Fri Dec 15 18:07:47 UTC 2023
PRIMARY
CHEBI
8588
Created by admin on Fri Dec 15 18:07:46 UTC 2023 , Edited by admin on Fri Dec 15 18:07:46 UTC 2023
PRIMARY
WIKIPEDIA
Protodioscin
Created by admin on Fri Dec 15 18:07:47 UTC 2023 , Edited by admin on Fri Dec 15 18:07:47 UTC 2023
PRIMARY
CAS
55056-80-9
Created by admin on Fri Dec 15 18:07:46 UTC 2023 , Edited by admin on Fri Dec 15 18:07:46 UTC 2023
PRIMARY
PUBCHEM
441891
Created by admin on Fri Dec 15 18:07:47 UTC 2023 , Edited by admin on Fri Dec 15 18:07:47 UTC 2023
PRIMARY
FDA UNII
D0LC3PH24P
Created by admin on Fri Dec 15 18:07:47 UTC 2023 , Edited by admin on Fri Dec 15 18:07:47 UTC 2023
PRIMARY