ISOSILYBIN B

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H22O10
Molecular Weight	482.4362
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=CC(=C1)[C@@H]2OC3=CC=C(C=C3O[C@H]2CO)[C@H]4OC5=CC(O)=CC(O)=C5C(=O)[C@@H]4O

InChI

InChIKey=FDQAOULAVFHKBX-WAABAYLZSA-N

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H22O10
Molecular Weight	482.4362
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17484885 | https://www.ncbi.nlm.nih.gov/pubmed/18332867 | http://cdn.intechopen.com/pdfs/32947/InTech-Silymarin_natural_flavonolignans_from_milk_thistle.pdf

Milk thistle (Silybum marianum) has been used for centuries for the treatment of liver disorders and as a hepatoprotectant. The primary extract of milk thistle is termed silymarin, a complex mixture that contains a number of structurally-related flavonolignans, the flavonoid, taxifolin, and a number of other constituents. The major flavonolignans present in most extracts are silybin A, silybin B, isosilybin A and isosilybin B, silydianin, silychristin and isosilychristin. Isosilybin B elicited the strongest anti-NF-kappaB and anti-HCV actions. The data suggest that silymarin-derived compounds may influence HCV disease course in some patients. Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2C8 18 Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28457856	Inhibitor 8504
Cytochrome P450 3A 22 Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23801821	Inhibitor 8504	60.0 µM [IC50]
angiogenesis 17 Target ID: GO:0001525 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22514647	Inhibitor 8504
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19934397	Inhibitor 8504	74.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22514647 https://www.ncbi.nlm.nih.gov/pubmed/18332867	Primary		Preclinical	Unknown Approved Use Unknown
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17484885	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A systematic approach to evaluate herb-drug interaction mechanisms: investigation of milk thistle extracts and eight isolated constituents as CYP3A inhibitors.	2013-09	23801821
Angiopreventive efficacy of pure flavonolignans from milk thistle extract against prostate cancer: targeting VEGF-VEGFR signaling.	2012	22514647
Identification of hepatoprotective flavonolignans from silymarin.	2010-03-30	20231449
Two flavonolignans from milk thistle (Silybum marianum) inhibit CYP2C9-mediated warfarin metabolism at clinically achievable concentrations.	2010-03	19934397
Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway.	2008-06-26	18332867
Inhibition of T-cell inflammatory cytokines, hepatocyte NF-kappaB signaling, and HCV infection by standardized Silymarin.	2007-05	17484885

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50 and 100 mg/kg body weight

Route of Administration: Oral

In Vitro Use Guide

Isosilybin B (10-90 uM) treatment decreased the AR and prostate specific antigen (PSA) levels in LNCaP, 22Rv1 and LAPC4 cells, but not in non-neoplastic human prostate epithelial PWR-1E cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:56:00 GMT 2025` Edited by `admin` on `Mon Mar 31 21:56:00 GMT 2025`
Record UNII	15EH97604R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOSILYBIN B

Common Name

English

ISOSILIBININ B

Preferred Name

English

ISOSILYBIN B [MI]

Common Name

English

SILYBIN A2

Common Name

English

ISOSILYBIN B (CONSTITUENT OF MILK THISTLE) [DSC]

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2-((2S,3S)-2,3-DIHYDRO-2-(4-HYDROXY-3-METHOXYPHENYL)-3-(HYDROXYMETHYL)-1,4-BENZODIOXIN-6-YL)-2,3-DIHYDRO-3,5,7-TRIHYDROXY-, (2R,3R)-

Systematic Name

English

Classification Tree Code System Code

DSLD

1488 (Number of products:2)