Cyclocurcumin

• CAT Number: M095071
• CAS Number: 153127-42-5
• Molecular Formula: C21H20O6
• Molecular Weight: 368.38
• Purity: ≥95%
• Synonyms: 2-(4-hydroxy-3-methoxyphenyl)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,3-dihydropyran-4-one
• InChI: InChI=1S/C21H20O6/c1-25-20-9-13(4-7-17(20)23)3-6-16-11-15(22)12-19(27-16)14-5-8-18(24)21(10-14)26-2/h3-11,19,23-24H,12H2,1-2H3/b6-3+
• InChIKey: IZLBLUIBVMGMIY-ZZXKWVIFSA-N
• SMILES: COC1=C(C=CC(=C1)C=CC2=CC(=O)CC(O2)C3=CC(=C(C=C3)O)OC)O

Cyclocurcumin is a potent p38α inhibitor. Cyclocurcumin shows antirheumatic, antivasoconstrictive and antioxidant activities[1][2][3].
Cyclocurcumin (10-40 μM; 18 h) leads to significant inhibition in the release of TNF-α in a dose-dependent manner in LPS-stimulated human macrophages[1].
Cyclocurcumin (5-25 μM) inhibits phenylephrine (HY-B0769)-induced vasocontraction in a concentration-dependent manner (IC50=14.9±1.0 μM) in freshly isolated rat aortic rings[2].
Cyclocurcumin (5-25 μM; 30 min) inhibits influx of intracellular calcium in a dose-dependent manner. Cyclocurcumin inhibits L-type calcium channel-mediated vasoconstriction in a concentration-dependent manner. The anticontractile effect of Cyclocurcumin is reversible[2].
Cyclocurcumin has strong activity as a scavenger of ˙OH and ˙OOH free radicals preferentially by its 4′-OH phenolic radical via a hydrogen-atom transfer mechanism in water and a physiological environment[3].

Reference

[1]. Fu M, et al. Cyclocurcumin, a curcumin derivative, exhibits immune-modulating ability and is a potential compound for the treatment of rheumatoid arthritis as predicted by the MM-PBSA method. Int J Mol Med. 2017 May;39(5):1164-1172.
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[2]. Kim K, et al. Cyclocurcumin, an Antivasoconstrictive Constituent of Curcuma longa (Turmeric). J Nat Prod. 2017 Jan 27;80(1):196-200.
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[3]. Li Y, et al. Antioxidant properties and free radical scavenging mechanisms of cyclocurcumin. New Journal of Chemistry, 2018, 42(15): 12698-12705.