SCUTELLARIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H18O12
Molecular Weight	462.3612
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(ccc1-c2cc(=O)c3c(cc(c(c3O)O)O[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C(=O)O)O4)O)O)O)o2)O

InChI

InChIKey=DJSISFGPUUYILV-ZFORQUDYSA-N

InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H18O12
Molecular Weight	462.3612
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21340731 | https://www.ncbi.nlm.nih.gov/pubmed/17878763 | https://www.ncbi.nlm.nih.gov/pubmed/21823483

Scutellarin is the main bioactive component of Breviscapine prepared from the traditional Chinese herb Erilgeron breviscapus (Vant) Hand-Mazz. Scutellarin demonstrated protective effect on cardiovascular and cerebrovascular ischemia. The potential cytoprotective effects of the drug against cerebrovascular ischemia were evidenced by reducing cerebral infarct sizes, ameliorating neurological deficit and inhibiting neuronal apoptosis. Scutellarin is capable of inhibiting I(Na) in neurons through predominantly affecting the inactivated state of I(Na). Scutellarin may alleviate cognitive impairment in a mouse model of hypoxia by promoting proliferation and neuronal differentiation of neural stem cells. Scutellarin might play an therapeutic role by inhibiting oxidative stress and apoptosis in Alzheimer's disease treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Target ID: Sodium channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/21340731	Blocker 511	7.1 µM [Ki]
Apoptosis 145 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26775564 \| https://www.ncbi.nlm.nih.gov/pubmed/21823483	Inhibitor 7728
Acetylcholinesterase 201 Target ID: CHEMBL3199 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21986571	Modulator 780

Conditions

Condition	Modality	Highest Phase	Product
Brain ischemia 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17878763 https://www.ncbi.nlm.nih.gov/pubmed/27103430 https://www.ncbi.nlm.nih.gov/pubmed/28809432	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17323972 https://www.ncbi.nlm.nih.gov/pubmed/21986571 https://www.ncbi.nlm.nih.gov/pubmed/22739358 https://www.ncbi.nlm.nih.gov/pubmed/25614117	Primary	Preclinical	Unknown Approved Use Unknown
Heart ischemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17878763 https://www.ncbi.nlm.nih.gov/pubmed/20942814 https://www.ncbi.nlm.nih.gov/pubmed/26775564	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of flavonoids on Naja naja and human recombinant synovial phospholipases A2 and inflammatory responses in mice.	1994	8190018
Antagonistic effect of scutellarin on the toxicity of selenium in rat livers.	2004 Jun	15131321
Neuroprotective effects of scutellarin on rat neuronal damage induced by cerebral ischemia/reperfusion.	2005 Dec	16297343
The anti-HIV-1 effect of scutellarin.	2005 Sep 2	16023998
Effects of scutellarin on apoptosis induced by cobalt chloride in PC12 cells.	2007 Dec 31	18442013
Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death.	2007 Mar 21	17323972
Scutellarin inhibits high glucose-induced and hypoxia-mimetic agent-induced angiogenic effects in human retinal endothelial cells through reactive oxygen species/hypoxia-inducible factor-1α/vascular endothelial growth factor pathway.	2014 Sep	25192544
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.	2015 Mar	25388478

Patents

Sample Use Guides

In Vivo Use Guide

Single administration of 60 mg of scutellarin.

Route of Administration: Oral

In Vitro Use Guide

100 uM of scutellarin sensitized resveratrol (200 uM) and 5-fluorouracil (500 uM)-evoked apoptosis in p53+/+ but not p53(-/-) cells. Resveratrol- and 5-fluorouracil-elicited caspase-6 activation were promoted by scutellarin in a time-dependent manner. scutellarin itself did not trigger apoptosis or caspase-6 activation at the concentration tested.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 14:15:11 UTC 2021` Edited by `admin` on `Sat Jun 26 14:15:11 UTC 2021`
Record UNII	16IGP0ML9A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCUTELLARIN

Common Name

English

SCUTELLAREIN 7-GLUCURONIDE

Systematic Name

English

SCUTELLAREIN 7-O-.BETA.-GLUCURONIDE

Systematic Name

English

SCUTELLAREIN 7-.BETA.-D-GLUCURONOSIDE

Systematic Name

English

BREVISCAPIN

Common Name

English

FLAVONE, 4',5,6,7-TETRAHYDROXY-, 7-.BETA.-D-GLUCOPYRANURONOSIDE

Systematic Name

English

SCUTELLAREIN GLUCURONIDE [WHO-DD]

Common Name

English

SCUTELLAREIN 7-O-.BETA.-D-GLUCURONIDE

Systematic Name

English

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 5,6-DIHYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL

Systematic Name

English

SCUTELLAREIN 7-.BETA.-D-GLUCURONIDE

Systematic Name

English

SCUTELLAREIN GLUCURONIDE [MI]

Common Name

English

GLUCOPYRANOSIDURONIC ACID, 5,6-DIHYDROXY-2-(P-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL, .BETA.-D-

Systematic Name

English

BREVISCAPINE

Common Name

English

SCUTELLAREIN-7-GLUCURONIDE

Common Name

English

S-7-G

Common Name

English

SCUTELLARIN B

Common Name

English

Code System Code Type Description

MERCK INDEX

M9819