| Identification | Back Directory | [Name]
AURANTIO-OBTUSIN | [CAS]
67979-25-3 | [Synonyms]
URANTIO-OBTUSIN
AURANTIO-OBTUSIN
Aurantio-obtusifolin
Aurantioobtusin, 98%, from Catsia tora Linn
1,3,7-Trihydroxy-2,8-diMethoxy-6-Methyl-9,10-anthracenedione
1,3,7-Trihydroxy-2,8-dimethoxy-6-methylanthracene-9,10-dione
9,10-Anthracenedione, 1,3,7-trihydroxy-2,8-dimethoxy-6-methyl- | [Molecular Formula]
C17H14O7 | [MDL Number]
MFCD13194886 | [MOL File]
67979-25-3.mol | [Molecular Weight]
330.291 |
| Chemical Properties | Back Directory | [Melting point ]
265-266 °C | [Boiling point ]
594.6±50.0 °C(Predicted) | [density ]
1.510±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Soluble in chloroform, DMSO and methan | [form ]
powder | [pka]
6.32±0.20(Predicted) | [color ]
Orange | [Major Application]
food and beverages | [InChI]
InChI=1S/C17H14O7/c1-6-4-7-11(17(24-3)12(6)19)14(21)10-8(13(7)20)5-9(18)16(23-2)15(10)22/h4-5,18-19,22H,1-3H3 | [InChIKey]
RNXZPKOEJUFJON-UHFFFAOYSA-N | [SMILES]
C1(O)=C2C(C(=O)C3=C(C2=O)C(OC)=C(O)C(C)=C3)=CC(O)=C1OC |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
WGK 3 | [HS Code ]
29389090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Aurantioobtusin is an anthraquinone originally isolated from Cassia seeds with diverse biological activities.1,2,3,4,5 It inhibits rat lens aldose reductase (RLAR) in vitro (IC50 = 13.6 μM).1 Aurantioobtusin (10 and 100 μM) activates the aryl hydrocarbon receptor (AhR) in a concentration-dependent manner.2 It inhibits rat platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), ADP, and collagen.3 Aurantioobtusin induces vasorelaxation in isolated precontracted rat mesenteric artery rings, an effect that is inhibited by the PI3K inhibitor LY290042 or inhibition of endothelial nitric oxide synthase (eNOS).4 It is larvicidal against A. gambiae mosquitoes (LD50 = 10 ppm).5 | [Chemical Properties]
Derived from the dried mature seeds of Cassia or Cassia minor, an annual herbaceous plant of the Leguminosae family | [Uses]
A compound found in herbal remedies, believed to have an effect on blood platelet aggregation and lower blood lipid count | [Definition]
ChEBI: A trihydroxyanthraquinone that is 1,3,7-trihydroxy-9,10-anthraquinone which is by methoxy groups at positions 2 and 8, and by a methyl group at position 6. | [in vivo]
Aurantio-obtusin (5-15 mg/kg; Oral administration; Single dose) in HFSW-induced mice reduces HFSW-induced lipid droplet accumulation and extensive steatosis in a dose-dependent manner[3].
Aurantio-obtusin (5-15 mg/kg; Oral administration; A single dose) inhibits fatty acid synthesis, promotes FAO and activates AMPK signaling and autophagy in HFSW-induced mice [3].
| Animal Model: | C57BL/6J mice model[3] | | Dosage: | 5 mg/kg, 10 mg/kg, 15 mg/kg | | Administration: | Oral gavage (p.o.), feeding with HFSW diet for 4 weeks then giving different dose of Aurantio-obtusin for another 4 weeks. | | Result: | Decreased the levels of TG and TC in liver and TG, ALT and AST in serum induced by HSFW.
Reduced the number and size of fat droplets in liver cells.
Significantly increased AMPK phosphorylation in HFSW-induced mice.
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| [References]
[1] DAE SIK JANG. Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.[J]. Biological & pharmaceutical bulletin, 2007, 30 11: 2207-2210. DOI: 10.1248/bpb.30.2207
[2] YOSHIAKI AMAKURA. Characterization of natural aryl hydrocarbon receptor agonists from cassia seed and rosemary.[J]. Molecules, 2014, 19 4: 4956-4966. DOI: 10.3390/molecules19044956
[3] HYE SOOK YUN-CHOI Michio T Jae Hoon Kim. Potential Inhibitors of Platelet Aggregation from Plant Sources, V. Anthraquinones from Seeds of Cassia obtusifolia and Related Compounds[J]. Journal of Natural Products , 1990, 53 3: 630-633. DOI: 10.1021/np50069a014
[4] SHUZHEN LI . Aurantio-obtusin relaxes systemic arteries through endothelial PI3K/AKT/eNOS-dependent signaling pathway in rats[J]. Journal of pharmacological sciences, 2015, 128 3: Pages 108-115. DOI: 10.1016/j.jphs.2015.05.006
[5] VALENTINE C MBATCHOU. Mosquito larvicidal activity of Cassia tora seed extract and its key anthraquinones aurantio-obtusin and obtusin.[J]. Parasites & Vectors, 2017: 562. DOI: 10.1186/s13071-017-2512-y |
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