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MedKoo Cat#: 574124 | Name: Aurantioobtusin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aurantioobtusin is an anthraquinone that inhibits rat lens aldose reductase (RLAR) and activates the aryl hydrocarbon receptor (AhR). It inhibits platelet aggregation induced by arachidonic acid, 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).

Chemical Structure

Aurantioobtusin
Aurantioobtusin
CAS#67979-25-3

Theoretical Analysis

MedKoo Cat#: 574124

Name: Aurantioobtusin

CAS#: 67979-25-3

Chemical Formula: C17H14O7

Exact Mass: 330.0740

Molecular Weight: 330.29

Elemental Analysis: C, 61.82; H, 4.27; O, 33.91

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 550.00 2 Weeks
100mg USD 850.00 2 Weeks
250mg USD 1,650.00 2 Weeks
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Related CAS #
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Synonym
Aurantioobtusin; Aurantio-obtusin; Aurantio obtusin
IUPAC/Chemical Name
1,3,7-trihydroxy-2,8-dimethoxy-6-methyl-9,10-anthracenedione
InChi Key
RNXZPKOEJUFJON-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OC1=C(OC)C(O)=C(C(C(C(OC)=C(O)C(C)=C2)=C2C3=O)=O)C3=C1
Appearance
A crystalline solid
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 330.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zhou F, Ding M, Gu Y, Fan G, Liu C, Li Y, Sun R, Wu J, Li J, Xue X, Li H, Li X. Aurantio-Obtusin Attenuates Non-Alcoholic Fatty Liver Disease Through AMPK- Mediated Autophagy and Fatty Acid Oxidation Pathways. Front Pharmacol. 2022 Jan 11;12:826628. doi: 10.3389/fphar.2021.826628. PMID: 35087411; PMCID: PMC8787202. 2: Xiao SL, Guan LJ, Jiang RF, Wang XG, Li X, Cai W. The Metabolism and Pharmacokinetics of Rhein and Aurantio-Obtusin. Curr Drug Metab. 2020;21(12):960-968. doi: 10.2174/1389200221666200719002128. PMID: 32682364. 3: Hyun SK, Lee H, Kang SS, Chung HY, Choi JS. Inhibitory activities of Cassia tora and its anthraquinone constituents on angiotensin-converting enzyme. Phytother Res. 2009 Feb;23(2):178-84. doi: 10.1002/ptr.2579. PMID: 18803227. 4: Hu M, Zhong Y, Liu J, Zheng S, Lin L, Lin X, Liang B, Huang Y, Xian H, Li Z, Zhang B, Wang B, Meng H, Du J, Ye R, Lu Z, Yang X, Yang X, Huang Z. An adverse outcome pathway-based approach to assess aurantio-obtusin-induced hepatotoxicity. Toxicology. 2022 Aug;478:153293. doi: 10.1016/j.tox.2022.153293. Epub 2022 Aug 19. PMID: 35995123. 5: Hu M, Lin L, Liu J, Zhong Y, Liang B, Huang Y, Li Z, Lin X, Wang B, Zhang B, Meng H, Ye R, Du J, Dai M, Peng Y, Li H, Wu Q, Gao H, Yang X, Huang Z. Aurantio- obtusin induces hepatotoxicity through activation of NLRP3 inflammasome signaling. Toxicol Lett. 2022 Jan 1;354:1-13. doi: 10.1016/j.toxlet.2021.10.011. Epub 2021 Oct 28. PMID: 34718095. 6: Yun-Choi HS, Kim JH, Takido M. Potential inhibitors of platelet aggregation from plant sources, V. Anthraquinones from seeds of Cassia obtusifolia and related compounds. J Nat Prod. 1990 May-Jun;53(3):630-3. doi: 10.1021/np50069a014. PMID: 2213033. 7: She YS, Ma LQ, Liu BB, Zhang WJ, Qiu JY, Chen YY, Li MY, Xue L, Luo X, Wang Q, Xu H, Zang DA, Zhao XX, Cao L, Shen J, Peng YB, Zhao P, Yu MF, Chen W, Nie X, Shen C, Chen S, Chen S, Qin G, Dai J, Chen J, Liu QH. Semen cassiae Extract Inhibits Contraction of Airway Smooth Muscle. Front Pharmacol. 2018 Dec 4;9:1389. doi: 10.3389/fphar.2018.01389. PMID: 30564120; PMCID: PMC6288305. 8: Mao R, Li W, He Z, Bai Z, Xia P, Liang Z, Liu Y. Physiological, transcriptional, and metabolic alterations in spaceflight-subjected Senna obtusifolia. Plant Physiol Biochem. 2019 Jun;139:33-43. doi: 10.1016/j.plaphy.2019.03.009. Epub 2019 Mar 9. PMID: 30878836. 9: Kwon KS, Lee JH, So KS, Park BK, Lim H, Choi JS, Kim HP. Aurantio-obtusin, an anthraquinone from cassiae semen, ameliorates lung inflammatory responses. Phytother Res. 2018 Aug;32(8):1537-1545. doi: 10.1002/ptr.6082. Epub 2018 Apr 20. PMID: 29675883. 10: Qin W, Yang Z, Yin J, Chen D, Huo J, Wang J, Wang L, Zhuo Q. Effect Assessment of Aurantio-Obtusin on Novel Human Renal Glomerular Endothelial Cells Model Using a Microfluidic Chip. Nutrients. 2022 Nov 2;14(21):4615. doi: 10.3390/nu14214615. PMID: 36364876; PMCID: PMC9654768. 11: Xu Y, Wan Y, Liu F, Chen J, Tan T, Guo L. Simultaneous determination of seven anthraquinones in Cassiae semen by natural deep eutectic solvent extraction. Phytochem Anal. 2022 Dec;33(8):1246-1256. doi: 10.1002/pca.3176. Epub 2022 Oct 3. PMID: 36191586. 12: Mao R, Bai Z, Wu J, Han R, Zhang X, Chai W, Liang Z. Transcriptome and HPLC Analysis Reveal the Regulatory Mechanisms of Aurantio-Obtusin in Space Environment-Induced Senna obtusifolia Lines. Int J Environ Res Public Health. 2022 Jan 14;19(2):898. doi: 10.3390/ijerph19020898. PMID: 35055719; PMCID: PMC8776150. 13: Mi BL, Sun Q, Qu YQ, Gao XX, Yu ZW, Ge GB, Cai SS, Zhang J, Zheng YC, Zhang ZQ. Glucuronidation of aurantio-obtusin: identification of human UDP- glucuronosyltransferases and species differences. Xenobiotica. 2014 Aug;44(8):716-21. doi: 10.3109/00498254.2014.895881. Epub 2014 Mar 11. PMID: 24618000. 14: Xu L, Li J, Tang X, Wang Y, Ma Z, Gao Y. Metabolomics of Aurantio-Obtusin- Induced Hepatotoxicity in Rats for Discovery of Potential Biomarkers. Molecules. 2019 Sep 23;24(19):3452. doi: 10.3390/molecules24193452. PMID: 31547563; PMCID: PMC6804130. 15: Nie C, Zhang F, Ma X, Guo R, Zhou S, Zhao L, Xu H, Xiao X, Wang Z. Determination of quality markers of Xuezhiling tablet for hyperlipidemia treatment. Phytomedicine. 2018 May 15;44:231-238. doi: 10.1016/j.phymed.2018.03.004. Epub 2018 Mar 15. PMID: 29631806. 16: Guo CY, Liao WT, Qiu RJ, Zhou DS, Ni WJ, Yu CP, Zeng Y. Aurantio-obtusin improves obesity and insulin resistance induced by high-fat diet in obese mice. Phytother Res. 2021 Jan;35(1):346-360. doi: 10.1002/ptr.6805. Epub 2020 Aug 4. PMID: 32749748. 17: Bu Z, Lv L, Li X, Chu C, Tong S. pH-zone-refining elution-extrusion countercurrent chromatography: Separation of hydroxyanthraquinones from Cassiae semen. J Sep Sci. 2017 Nov;40(21):4281-4288. doi: 10.1002/jssc.201700809. Epub 2017 Sep 26. PMID: 28845549. 18: Xu L, Wang Y, Ma Z, Tang X, Gao Y. Urine Metabolomics Study on Potential Hepatoxic Biomarkers Identification in Rats Induced by Aurantio-Obtusin. Front Pharmacol. 2020 Aug 12;11:1237. doi: 10.3389/fphar.2020.01237. PMID: 32903457; PMCID: PMC7435054. 19: Zhang WD, Wang PY, Wang Y, Wang Q, Gu Y, Cao J, Wang SQ, Wang XJ. Simultaneous determination of aurantio-obtusin, chrysoobtusin, obtusin and 1-desmethylobtusin in rat plasma by UHPLC-MS/MS. Biomed Chromatogr. 2014 Mar;28(3):369-74. doi: 10.1002/bmc.3030. Epub 2013 Sep 12. PMID: 24027008. 20: Yu X, Wei LH, Zhang JK, Chen TR, Jin Q, Wang YN, Zhang SJ, Dou TY, Cao YF, Guo WZ, Ge GB, Yang L. Anthraquinones from Cassiae semen as thrombin inhibitors: in vitro and in silico studies. Phytochemistry. 2019 Sep;165:112025. doi: 10.1016/j.phytochem.2019.04.018. Epub 2019 Jun 14. PMID: 31207449.