ALOESIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22O9
Molecular Weight	394.3733
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cc(c(c2c1c(=O)cc(CC(=O)C)o2)[C@@]3([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O3)O)O)O)O

InChI

InChIKey=HKIKAXXIWJHWLY-ZIIYPAMZSA-N

InChI=1S/C19H22O9/c1-7-3-10(22)14(19-17(26)16(25)15(24)12(6-20)28-19)18-13(7)11(23)5-9(27-18)4-8(2)21/h3,5,12,15-17,19-20,22,24-26H,4,6H2,1-2H3/t12-,15-,16+,17-,19+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12451482 | https://www.ncbi.nlm.nih.gov/pubmed/28702312 | https://www.ncbi.nlm.nih.gov/pubmed/12372097 | https://www.ncbi.nlm.nih.gov/pubmed/26265996

Aloesin is a chromone derivative isolated from aloe vera. It has many biological effects, such as wound and burn healing properties, and antioxidant, free radical scavenging, anti-inflammatory, and immunomodulatory effects. Aloesin has been shown to be a potent and selective inhibitor of tyrosinase. It exhibited direct inhibitory effects on melanogenesis. Aloesin treatment showed pigmentation suppression in a dose-dependent manner. Thus, aloesin may be used as an agent that inhibits melanin formation induced by UV radiation. Aloesin is thought to be one of the active ingredients in regards to the anti-diabetic activity of Aloe. Aloesin exerts its anticancer effect through the MAPK signaling pathway. It is a novel therapeutic drug for ovarian cancer treatment.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase
Cutaneous wounds 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28478809	Primary	Preclinical
Ovarian cancer 145 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28702312	Primary	Preclinical
Skin hyperpigmentation 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12372097	Preventing	Phase II

PubMed

Title	Date	PubMed
The distribution of aloesin in some South African Aloe species.	1967 Aug	5618645
Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism.	1999 Jun	10403123
Antioxidant, free radical scavenging and anti-inflammatory effects of aloesin derivatives in Aloe vera.	2002 Nov	12451482
Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase.	2002 Oct	12213089
Aloesin inhibits hyperpigmentation induced by UV radiation.	2002 Sep	12372097
In vitro and in vivo assessment of the genotoxic activity of aloesin.	2011 Nov	21821088
Aloesin as a medical food ingredient for systemic oxidative stress of diabetes.	2015 Aug 10	26265996
Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway.	2017	28702312
Tyrosinase inhibitory components from Aloe vera and their antiviral activity.	2017 Dec	27778516
Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo.	2017 May 15	28478809

Patents

Sample Use Guides

In Vivo Use Guide

100 mg ⁄ g vehicle, four times daily for 15 days.

Route of Administration: Topical

In Vitro Use Guide

Aloesin did not induce reverse mutations in Salmonella typhimurium and Escherichia coli at any of the tested dose levels up to 10,000 ug/plate. Similarly, aloesin did not increase the incidence of chromosome aberrations when incubated with Chinese hamster lung cells at any of the tested concentrations up to 10,000 ug/mL.

Name

Type

Language

ALOESIN

Official Name

English

ALOESIN [MI]

Common Name

English

ALOE RESIN B

Common Name

English

NSC-631262

Code

English

ALOESIN [INCI]

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 8-.BETA.-D-GLUCOPYRANOSYL-7-HYDROXY-5-METHYL-2-(2-OXOPROPYL)-

Common Name

English

Code System Code Type Description

MERCK INDEX

M1571