ALOESIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22O9
Molecular Weight	394.3726
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CC1=CC(=O)C2=C(O1)C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(O)C=C2C

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

Targets

Primary Target	Pharmacology	Potency
Tyrosinase 41 Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10403123	Inhibitor 8504	0.1 mM [IC50]
MAPK signaling pathway 26 Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28702312	Inhibitor 8504
SMAD protein signal transduction 1 Target ID: GO:0060395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28478809	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Skin hyperpigmentation 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12372097	Preventing	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28702312	Primary	Preclinical	Unknown Approved Use Unknown
Cutaneous wounds 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28478809	Primary	Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
100 mg 4 times / day multiple, topical Studied dose Dose: 100 mg, 4 times / day Route: topical Route: multiple Dose: 100 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12372097	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12372097	Sources: https://pubmed.ncbi.nlm.nih.gov/12372097

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00C2YS	https://www.1pchem.com/search?query=1P00C2YS
BLD Pharm	BD764107	http://www.bldpharm.com/search/Search.html?keyword=BD764107
BOC Sciences	30861-27-9	http://www.bocsci.com/description.asp?cas=30861-27-9
Cayman Chemical	14649	http://www.caymanchem.com/app/template/Product.vm/catalog/14649
Chem Scene	CS-0022690	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0022690
eMolecules	31239929	https://orderbb.emolecules.com/search/#?query=31239929
mcule	MCULE-1978959211	https://mcule.com/MCULE-1978959211/
MedChem Express	HY-N2460	https://www.medchemexpress.com/search.html?q=HY-N2460&ft=&fa=&fp=
MolPort	MolPort-044-183-260	https://www.molport.com/shop/molecule-link/MolPort-044-183-260
TargetMol	T5755	https://www.targetmol.com/search?keyword=T5755
Toronto Research Chemicals	A575435	https://www.trc-canada.com/product-detail/?CatNum=A575435

PubMed

Title	Date	PubMed
Tyrosinase inhibitory components from Aloe vera and their antiviral activity.	2017-12	27778516
Aloesin from Aloe vera accelerates skin wound healing by modulating MAPK/Rho and Smad signaling pathways in vitro and in vivo.	2017-05-15	28478809
Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway.	2017	28702312
Aloesin as a medical food ingredient for systemic oxidative stress of diabetes.	2015-08-10	26265996
In vitro and in vivo assessment of the genotoxic activity of aloesin.	2011-11	21821088
Antioxidant, free radical scavenging and anti-inflammatory effects of aloesin derivatives in Aloe vera.	2002-11	12451482
Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase.	2002-10	12213089
Aloesin inhibits hyperpigmentation induced by UV radiation.	2002-09	12372097
Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism.	1999-06	10403123
The distribution of aloesin in some South African Aloe species.	1967-08	5618645

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

NSC-631262

Preferred Name

English

ALOESIN

Official Name

English

ALOESIN [MI]

Common Name

English

ALOE RESIN B

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