Aloin

Names

[ Name ]:
Aloin

[Synonym ]:
(1S)-1,5-Anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
(10R)-10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
EINECS 215-808-0
barbaloin isomers
BAR-5'-monophosphate
N6-Benzyladenosin-5'-phosphat
(10R)-1,8-Dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-9(10H)-anthracenone
Aloin
10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
Benzyl-amp
isobarbaloin
Benzyl-adenosine monophosphate
9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (R)-
MFCD00151160
10-(1',5'-Anhydroglucosyl)-aloe-emodin-9-anthrone
6-N-benzyladenosine-5'-O-monophosphate
N6-Benzyladenosin-5'-monophosphat
N6-Benzyladenosine 5'-Phosphat
D-Glucitol, 1,5-anhydro-1-C-[(9R)-9,10-dihydro-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9-anthracenyl]-, (1S)-
1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
(1S)-1,5-Anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydro-9-anthracenyl]-D-glucitol

Biological Activity

[Description]:

Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities.IC50 value:Target:in vitro: Aloin significantly inhibited HUVECs proliferation, migration and tube formation in vitro. suppressed activation of VEGF receptor (VEGFR) 2 and STAT3 phosphorylation in endothelial cells. In addition, the constitutively activated STAT3 protein, and the expression of STAT3-regulated antiapoptotic (Bcl-xL), proliferative (c-Myc), and angiogenic (VEGF) proteins were also down-regulated in response to AL in human SW620 cancer cells [1]. aloin exerted inhibition of cell proliferation, adhesion and invasion abilities of B16-F10 melanoma cells under non-cytotoxic concentrations. Furthermore, aloin induced melanoma cell differentiation through the enhancement of melanogenesis and transglutaminase activity [2].in vivo: Aloin substantially reduced tumor volumes and weight in vivo mouse xenografts, without obviously toxicity [1]. Aloin (10, 30 mg/kg bw) or vehicle was given by gavage to mice after each alcohol administration. Alcohol elevated the serum transaminases alanine aminotransferase, aspartate aminotransferase, total cholesterol and triglyceride levels which were significantly attenuated by the co-administration of aloin (p < 0.05) [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Quinones

[References]

[1]. Pan Q, et al. Inhibition of the angiogenesis and growth of Aloin in human colorectal cancer in vitro and in vivo. Cancer Cell Int. 2013 Jul 12;13(1):69.

[2]. Tabolacci C, et al. Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation. Amino Acids. 2013 Jan;44(1):293-300.

[3]. Cui Y, et al. Aloin protects against chronic alcoholic liver injury via attenuating lipid accumulation, oxidative stress and inflammation in mice. Arch Pharm Res. 2014 Dec;37(12):1624-33.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
752.6±60.0 °C at 760 mmHg

[ Melting Point ]:
148-149ºC

[ Molecular Formula ]:
C₂₁H₂₂O₉

[ Molecular Weight ]:
418.394

[ Flash Point ]:
268.0±26.4 °C

[ Exact Mass ]:
418.126373

[ PSA ]:
167.91000

[ LogP ]:
1.86

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.741

[ Stability ]:
Stable, but light sensitive. Incompatible with bases, strong oxidizing agents. Combustible.

[ Water Solubility ]:
pyridine: 50 mg/mL, clear, dark red

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ6520000

CHEMICAL NAME :: 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymeth yl)-, 9(10H)-anthracenone-, (+)-

CAS REGISTRY NUMBER :: 1415-73-2

LAST UPDATED :: 199012

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C21-H22-O9

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),314,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LZ6520000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The content of secondary phenol metabolites in pruned leaves of Aloe arborescens, a comparison between two methods: leaf exudates and leaf water extract.

J. Nat. Med. 62(4) , 430-5, (2008)

Aloe arborescens plants, originating from the deserts of South Africa, are grown in the Introduction Garden at Sede Boker in the Negev Desert of Israel. In previous studies, we developed agro-technica...

Determination of aloenin, barbaloin and isobarbaloin in aloe species by micellar electrokinetic chromatography.

J. Chromatogr. B. Biomed. Sci. Appl. 752(1) , 91-7, (2001)

Aloenin, barbaloin and isobarbaloin in JP Aloe, Aloe barbadensis (Aloe vera) and Aloe arborescens Miller var. natalensis Berger (Aloe arborescens Miller) were determined by micellar electrokinetic chr...

Liquid chromatographic determination of barbaloin (aloin) in foods.

J. Assoc. Off. Anal. Chem. 68(3) , 493-4, (1985)

A simple and rapid liquid chromatographic method is described for the determination of barbaloin (aloin, 10-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthraceno ne) in foods. Barbaloin i...