DIHYDROTANSHINONE I

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H14O3
Molecular Weight	278.302
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1COC2=C1C(=O)C(=O)C3=C2C=CC4=C(C)C=CC=C34

InChI

InChIKey=HARGZZNYNSYSGJ-JTQLQIEISA-N

InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H14O3
Molecular Weight	278.302
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900610 | https://www.ncbi.nlm.nih.gov/pubmed/27891092 | https://www.ncbi.nlm.nih.gov/pubmed/27580276

Dihydrotanshinone I (DHI), a diterpenoid first isolated from the roots of Salvia miltiorrhiza, is a relatively high affinity inhibitor of human AChE. Dihydrotanshinone I (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice. Dihydrotanshinone I dramatically inhibits the enhanced expression of LOX-1, NOX4, and NF-κB in aorta. Dihydrotanshinone I treatment can improve cardiac function, reduce infarct size, ameliorate the variations in myocardial zymogram and histopathological disorders, decrease 20-HETE generation, and regulate apoptosis-related protein in myocardial ischemia-reperfusion rats.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900610	Inhibitor 8297	0.6 µM [Ki]
Topoisomerase I 4 Target ID: CHEMBL6023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27389501	Inhibitor 8297
UDP-glucuronosyltransferase 1-9 11 Target ID: CHEMBL1743319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28466663	Inhibitor 8297	0.72 µM [IC50]
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26547530	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Liver disease 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28257144	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27891092	Primary	Preclinical	Unknown Approved Use Unknown
Myocardial ischemia-reperfusion injury 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27580276	Primary	Preclinical	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26547530	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Structures of human acetylcholinesterase bound to dihydrotanshinone I and territrem B show peripheral site flexibility.	2013 Nov 14	24900610
Dihydrotanshinone I Attenuates Atherosclerosis in ApoE-Deficient Mice: Role of NOX4/NF-κB Mediated Lectin-Like Oxidized LDL Receptor-1 (LOX-1) of the Endothelium.	2016	27891092

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Dihydrotanshinone I (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice.

Route of Administration: Intragastric

In Vitro Use Guide

In lipopolysaccharide (LPS)-stimulated human umbilical vein endothelial cells (HUVECs), Dihydrotanshinone I (10 nM) decreased lectin-like ox-LDL receptor-1 (LOX-1) and NADPH oxidase 4 (NOX4) expression, reactive oxygen species (ROS) production, NF-κB nuclear translocation, ox-LDL endocytosis and monocytes adhesion.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:11:00 UTC 2023` Edited by `admin` on `Sat Dec 16 18:11:00 UTC 2023`
Record UNII	562G9360V6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIHYDROTANSHINONE I

Common Name

English

DIHYDROTANSHINONE (CONSTITUENT OF CHINESE SALVIA) [DSC]

Common Name

English

DIHYDROTANSHINONE I, (-)-

Common Name

English

PHENANTHRO(1,2-B)FURAN-10,11-DIONE, 1,2-DIHYDRO-1,6-DIMETHYL-, (1R)-

Systematic Name

English

(-)-DIHYDROTANSHINONE I

Systematic Name

English

Code System Code Type Description

HSDB

8105