ALOIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H22O9
Molecular Weight	418.394
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@]2([H])C3=CC=CC(O)=C3C(=O)C4=C2C=C(CO)C=C4O

InChI

InChIKey=AFHJQYHRLPMKHU-OSYMLPPYSA-N

InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H22O9
Molecular Weight	418.394
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23569857 | https://www.ncbi.nlm.nih.gov/pubmed/28656293 | https://www.ncbi.nlm.nih.gov/pubmed/29072259 | https://www.ncbi.nlm.nih.gov/pubmed/28673785

The ALOIN A (barbaloin) is considered to be the most specific secondary phytoconstituent in Aloe species, widely distributed throughout the world. Barbaloin has been found to have a strong inhibitory effect on histamine release from mast cells. Orally administered barbaloin is poorly absorbed but is metabolized by intestinal microflora to aloe emodin, which is readily absorbed. Barbaloin is the main medicinal constituent of aloe vera, which has anti-inflammatory activity. Moreover, it has strong anti-oxidant and anti-tumor properties. For example, barbaloin inhibited the proliferation and metastasis of non-small cell lung carcinoma cells in vivo and in vitro. Barbaloin demonstrated a cardioprotective potential: barbaloin pretreatment attenuates myocardial ischemia-reperfusion injury. Plus, it might be used as an antiarrhythmic drug.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
p38MAPK cascade 8 Target ID: GO:0038066 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28656293	Inhibitor 8297
AMPK signaling pathway 5 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28673785	Activator 1430
Calcium and sodium voltage-gated ion channels (rabbit) 1 Target ID: Calcium and sodium voltage-gated ion channels (rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29072259	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28656293	Primary	Preclinical	Unknown Approved Use Unknown
Myocardial ischemia-reperfusion injury 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28673785	Preventing	Preclinical	Unknown Approved Use Unknown
Ventricular arrhythmia 50 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29072259	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
In vitro antimicrobial and antioxidant activities of anthrone and chromone from the latex of Aloe harlana Reynolds.	2011 Dec	21452374
Barbaloin pretreatment attenuates myocardial ischemia-reperfusion injury via activation of AMPK.	2017 Sep 2	28673785
Barbaloin inhibits ventricular arrhythmias in rabbits by modulating voltage-gated ion channels.	2018 Mar	29072259

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 20 mg/kg/d for 5 days

Route of Administration: Intragastric

In Vitro Use Guide

Application of barbaloin (100, 200 uM/L) decreased ATX II-enhanced late sodium current (INa.L) by 36.6% and 71.8%, respectively. However, barbaloin up to 800 uM/L did not affect the inward rectifier potassium current (Ik1) or the rapidly activated delayed rectifier potassium current (Ikr) in ventricular myocytes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:25:29 GMT 2023` Edited by `admin` on `Fri Dec 15 16:25:29 GMT 2023`
Record UNII	648RW354S9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALOIN A

Common Name

English

(10S)-10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE

Common Name

English

9(10H)-ANTHRACENONE, 10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-, (10S)-

Systematic Name

English

ALOIN A [MI]

Common Name

English

NSC-407305

Code

English

9(10H)-ANTHRACENONE, 10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-, (S)-

Systematic Name

English

BARBALOIN A

Common Name

English

Code System Code Type Description

NSC

407305