(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one

• ChemBase ID: 72999
• Molecular Formular: C21H22O9
• Molecular Mass: 418.39398
• Monoisotopic Mass: 418.12638228
• SMILES: [C@@H]1(O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)[C@H]1c2c(C(=O)c3c1cc(cc3O)CO)c(ccc2)O)CO
• Canonical SMILES: OCc1cc(O)c2c(c1)[C@@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
• InChI: 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
• InChIKey: AFHJQYHRLPMKHU-OSYMLPPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
• IUPAC Traditional name: (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one; (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• Synonyms: Barbaloin; Barbaloin; Aloin(Barbaloin); 1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone; 10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone; Aloin A; Aloin

Database IDs

• CAS Number: 1415-73-2
• EC Number: 215-808-0
• MDL Number: MFCD00151160
• Beilstein Number: 6077558
• PubChem SID: 24890427; 162037919; 24891938
• PubChem CID: 12305761

CALCULATED PROPERTIES

• Acid pKa: 9.505504
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 0.41494715
• LogD (pH = 7.4): 0.4116161
• Log P: 0.41498974
• Molar Refractivity: 103.7931 cm^3
• Polarizability: 40.31564 Å^3
• Polar Surface Area: 167.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: pyridine: soluble50 mg/mL, clear, dark red

Safety Information

• Storage Condition: -20°C
• RTECS: LZ6520000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Increase prostaglandin synthesis; Na+, K(+)-adenosine triphosphatase (ATPase) inhibitor

Product Information

• Purity: ~50%; ≥97%
• Salt Data: Free Base
• Biological Source: Constit. of various Aloe spp.; from Aloe barbadensis Miller leaves; from Curacao aloe
• Loss on Drying: ≤5% loss on drying
• Application(s): Laxative; Purgative
• Empirical Formula (Hill Notation): C21H22O9

DETAILS

Selleck Chemicals - S2375

Research Area: Cancer
Biological Activity:
Aloin(Barbaloin) is a potent tyrosinase inhibitor with an IC50 of 97 µM for HeLaS3 cells. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.It also shows a pronounced antiproliferative effect at physiological concentration, causes cell cycle arrest in the S phase, and markedly increases HeLaS3 cell apoptosis (to 24%). In the concentration range of 20-100 µM, its action was accompanied by remarkable changes in the activity of almost all antioxidant enzymes: MnSOD activity was increased many fold, while CuZnSOD and iNOS activities were inhibited. Moreover, inhibition of CuZnSOD was shown to occur by direct aloin interaction with the enzyme. [1][2]

Sigma Aldrich - A0451

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

Sigma Aldrich - B6906

Application
Aloin, a natural mixed diastereomer (A/B) anthracycline from aloe plant, is studied as an antineoplastic agent that enhances melanogenesis and transglutaminase activity. Aloin A is used as a stabilizer in the preparation of gold and silver nanoparticles.
Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

Sigma Aldrich - 06088

Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

REFERENCES

• Ni??iforovi?? A et al. Cancer Biol Ther. 2007 Aug;6(8):1200-5.
• 1. Akao T, Che QM, Kobashi K, Hattori M, Namba T.
• A purgative action of barbaloin is induced by Eubacterium sp. strain BAR, a human intestinal anaerobe, capable of transforming barbaloin to aloe-emodin anthrone. Biol Pharm Bull. 1996 Jan;19(1):136-8.
• 2. Ishii Y, Tanizawa H, Takino Y. Studies of aloe. III. Mechanism of cathartic effect. (2). Chem Pharm Bull (Tokyo). 1990 Jan;38(1):197-200.
• 3. Capasso F, Mascolo N, Autore G, Duraccio MR. Effect of indomethacin on aloin and 1,8 dioxianthraquinone-induced production of prostaglandins in rat isolated colon.
• Prostaglandins. 1983 Oct;26(4):557-62.