SILIDIANIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H22O10
Molecular Weight	482.4362
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CO[C@@]3(O)C(=O)[C@H](C=C([C@H]4OC5=CC(O)=CC(O)=C5C(=O)[C@@H]4O)[C@@]13[H])[C@@H]2C6=CC(OC)=C(O)C=C6

InChI

InChIKey=CYGIJEJDYJOUAN-JSGXPVSSSA-N

InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3/t11-,13-,18+,20+,22+,23-,25-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29439388 | https://www.ncbi.nlm.nih.gov/pubmed/31069872 | https://www.ncbi.nlm.nih.gov/pubmed/16444663 | https://www.ncbi.nlm.nih.gov/pubmed/118048 | https://www.ncbi.nlm.nih.gov/pubmed/118049

Silydianin is a flavonolignan from Silymarin, which is the major constituent of milk thistle extract. Silydianin, an active constituent of Silybium marianum, have inhibitory properties against the P2Y12 receptor and block ADP-induced blood platelet activation. Silydianin has antiinflammatory activity, it regulates caspase-3 activation, affects cell membranes and acts as a free radical scavenger. Silydianin non-competitively inhibits the lipoxygenase from soybeans in vitro. It also inhibits the formation of prostaglandins in vitro.

Approval Year

PubMed

Title	Date	PubMed
Silymarin, an inhibitor of prostaglandin synthetase.	1979 Dec 15	118049
Silymarin, an inhibitor of lipoxygenase.	1979 Dec 15	118048
Inhibitory Effect of Flavonolignans on the P2Y12 Pathway in Blood Platelets.	2018 Feb 10	29439388

Sample Use Guides

In Vitro Use Guide

When polymorphonuclear neutrophils were cultured with 100 uM silydianin for 24 h, caspase-3 was activated. Induction of apoptosis by silydianin was accompanied by a decrease in luminol-enhanced chemiluminescence as well as superoxide radical (O2*-) release in freshly isolated cells and lipid peroxidation in mouse spleen microsomes.

Name

Type

Language

SILIDIANIN

Official Name

English

SILIDIANINE

Common Name

English

(+)-2,3.ALPHA.,3A.ALPHA.A,7A-TETRAHYDRO-7A.ALPHA.-HYDROXY-8-(4-HYDROXY-3-METHOXYPHENYL)-4-(3.ALPHA.,5,7-TRIHYDROXY-4-OXO-2.BETA.-CHROMANYL)-3,6-METHANOBENZOFURAN-7(6.ALPHA.H)-ONE

Common Name

English

SILIDIANIN (CONSTITUENT OF MILK THISTLE) [DSC]

Common Name

English

SILYDIANIN

Common Name

English

SILYDIANIN [USP-RS]

Common Name

English

silidianin [INN]

Common Name

English

SILIDIANIN [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2081