Tetrahydrocurcumin Derivatives Enhanced the Anti-Inflammatory Activity of Curcumin: Synthesis, Biological Evaluation, and Structure–Activity Relationship Analysis
| dc.contributor.author | González, Yisett | |
| dc.contributor.author | Mojica-Flores, Randy | |
| dc.contributor.author | Moreno-Labrador, Dilan | |
| dc.contributor.author | Pecchio, Marisín | |
| dc.contributor.author | Rao, K. S. Jagannatha | |
| dc.contributor.author | Ahumedo-Monterrosa, Maicol | |
| dc.contributor.author | Fernández, Patricia L. | |
| dc.contributor.author | Larionov, Oleg V. | |
| dc.contributor.author | Lakey-Beitia, Johant | |
| dc.date.accessioned | 2024-06-28T15:01:59Z | |
| dc.date.available | 2024-06-28T15:01:59Z | |
| dc.date.issued | 2023-11-26 | |
| dc.date.updated | 2024-06-28T15:01:59Z | |
| dc.description.abstract | Tetrahydrocurcumin, the most abundant curcumin transformation product in biological systems, can potentially be a new alternative therapeutic agent with improved anti-inflammatory activity and higher bioavailability than curcumin. In this article, we describe the synthesis and evaluation of the anti-inflammatory activities of tetrahydrocurcumin derivatives. Eleven tetrahydrocurcumin derivatives were synthesized via Steglich esterification on both sides of the phenolic rings of tetrahydrocurcumin with the aim of improving the anti-inflammatory activity of this compound. We showed that tetrahydrocurcumin (<b>2</b>) inhibited TNF-α and IL-6 production but not PGE<sub>2</sub> production. Three tetrahydrocurcumin derivatives inhibited TNF-α production, five inhibited IL-6 production, and three inhibited PGE<sub>2</sub> production<sub>.</sub> The structure–activity relationship analysis suggested that two factors could contribute to the biological activities of these compounds: the presence or absence of planarity and their structural differences. Among the tetrahydrocurcumin derivatives, cyclic compound <b>13</b> was the most active in terms of TNF-α production, showing even better activity than tetrahydrocurcumin. Acyclic compound <b>11</b> was the most effective in terms of IL-6 production and retained the same effect as tetrahydrocurcumin. Moreover, acyclic compound <b>12</b> was the most active in terms of PGE<sub>2</sub> production, displaying better inhibition than tetrahydrocurcumin. A 3D-QSAR analysis suggested that the anti-inflammatory activities of tetrahydrocurcumin derivatives could be increased by adding bulky groups at the ends of compounds <b>2</b>, <b>11</b>, and <b>12</b>. | |
| dc.identifier | doi: 10.3390/molecules28237787 | |
| dc.identifier.citation | Molecules 28 (23): 7787 (2023) | |
| dc.identifier.uri | https://hdl.handle.net/20.500.12588/6448 | |
| dc.title | Tetrahydrocurcumin Derivatives Enhanced the Anti-Inflammatory Activity of Curcumin: Synthesis, Biological Evaluation, and Structure–Activity Relationship Analysis |