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AURANTIO-OBTUSIN

Product NameAURANTIO-OBTUSIN
CAS67979-25-3
MFC17H14O7
MW330.29
EINECS
MOL File67979-25-3.mol

Chemical Properties

Melting point	265-266 °C
Boiling point	594.6±50.0 °C(Predicted)
Density	1.510±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Soluble in chloroform, DMSO and methan
form	powder
pka	6.32±0.20(Predicted)
color	Orange
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 Information

Safety Statements	24/25
HS Code	29389090

Usage And Synthesis

Description

Aurantioobtusin is an anthraquinone originally isolated from Cassia seeds with diverse biological activities. It inhibits rat lens aldose reductase (RLAR) in vitro (IC₅₀ = 13.6 μM). Aurantioobtusin (10 and 100 μM) activates the aryl hydrocarbon receptor (AhR) in a concentration-dependent manner. It inhibits rat platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), ADP, and collagen. 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). It is larvicidal against A. gambiae mosquitoes (LD₅₀ = 10 ppm).

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.

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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