SYLVATESMIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24O6
Molecular Weight	372.4117
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CO[C@@H](C3=CC(OC)=C(OC)C=C3)[C@@]1([H])CO[C@@H]2C4=CC(OC)=C(O)C=C4

InChI

InChIKey=CPJKKWDCUOOTEW-YJPXFSGGSA-N

InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H24O6
Molecular Weight	372.4117
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/28887216 | https://www.ncbi.nlm.nih.gov/pubmed/10630110 | DOI: 10.1007/s00044-009-9217-5 | https://www.ncbi.nlm.nih.gov/pubmed/10483379 | https://www.ncbi.nlm.nih.gov/pubmed/22210027

Sylvatesmin is a furofuran lignin isolated from Forsythia suspense, Osmanthus fragrans and other plants. It protected LDL from lipid peroxidation and demonstrated free radical scavenging activity. Molecular modeling showed that sylvatesmin exhibited the highest inhibition of aldose reductase. In nutritive hyperlipidemia mice fed with high-cholesterol in vivo, the serum levels of blood TG and LDL-C were remarkably down-regulated by sylvatesmin. In vitro, sylvatesmin exhibited anti-inflammatory and anti-cancer activity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
lipid oxidation 20 Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10630110	Inhibitor 8297	0.89 µM [IC50]
Aldose reductase 44 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28321889	Inhibitor 8297
nitric oxide production involved in inflammatory response 17 Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22210027	Inhibitor 8297	25.5 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Hyperlipidemia 80 Sources: DOI: 10.1007/s00044-009-9217-5	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10483379 https://www.ncbi.nlm.nih.gov/pubmed/20162394	Primary	Basic research	Unknown Approved Use Unknown
Inflammatory diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22210027	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of low density lipoprotein oxidation by tetrahydrofurofuran lignans from Forsythia suspensa and Magnolia coco.	1999 Dec	10630110

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 150 mg/kg for 10 days

Route of Administration: Intragastric

In Vitro Use Guide

The inhibitions of sylvatesmin on the survival of three tumor cell lines, human hepatoma cells (SMMC-7721), human uterine cervix carcinoma cells (Hela) and mouse melanotic carcinoma cells (B16), were studied. The half inhibition concentration (IC50) of sylvatesmin for B16 cells was 40.4 ug/ml, for SMMC-7721 cells 113.4 and for Hela cells 127.9.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:19:23 UTC 2023` Edited by `admin` on `Sat Dec 16 09:19:23 UTC 2023`
Record UNII	886IAL08GN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SYLVATESMIN

Common Name

English

EPIPINORESINOL METHYL ETHER

Common Name

English

(+)-PHILLYGENIN

Common Name

English

PHILLYRIN AGLYCONE

Common Name

English

PHENOL, 4-((1S,3AR,4R,6AR)-4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXY-

Systematic Name

English

PHILLYGENIN

Common Name

English

(+)-MONOMETHYLPINORESINOL

Common Name

English

Code System Code Type Description

PUBCHEM

3083590