Ethyl p-methoxycinnamate Exhibits Superior Multi-Modal Anti-Inflammatory Activity Compared to Structurally Related Cinnamic Acid Derivatives

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Sarmoko Sarmoko, Nisa Yulianti Suprahman, Anjar Hermadi Saputro, Iwan Syahjoko Saputra, Khaerunnisa Anbar Istiadi, Arif Fadlan, Fadilah Fadilah, I Gede Raditya Purwanata, Vito Rahmat Fitrah

2026 Journal of Pharmacopuncture Vol. 29 Issue 1 Article Cited by 0 Quartile

Abstract

Objectives: This study aimed to investigate the anti-inflammatory potential of cinnamic acid (CA) and its derivatives, ethyl p-methoxycinnamate (EPMC) and trans-4-methoxy cinnamic acid (APMC), using integrated in silico, in vitro, and in vivo approaches to identify safer alternatives to conventional nonsteroidal anti-inflammatory drugs (NSAIDs). Methods: Molecular docking was performed to evaluate binding interactions with inflammation-related proteins, including heat shock protein 90 alpha family class A member 1 (HSP90AA1), Janus kinase 2 (JAK2), prostaglandin-endoperoxide synthase 2 (PTGS2), lipoxygenase, heat shock protein 90 beta family class B member 1 (HSP90AB1), and nitric oxide synthase 3 (NOS3). In vitro anti-inflammatory activity was assessed using bovine serum albumin (BSA) denaturation assays to determine the half-maximal inhibitory concentration (IC50). In vivo efficacy was evaluated using a carrageenan-induced paw edema model in mice (n = 3 per group), and hematological analysis was conducted 3 hours post-induction. Results: Molecular docking revealed that EPMC exhibited superior multi-target binding affinities across five inflammatory proteins compared with allyl p-methoxycinnamate (APMC) and CA, with notable interaction with prostaglandin-endoperoxide synthase 2 (PTGS2/COX-2) interaction (-6.29 kcal/mol). CA uniquely bound NOS3 (-3.06 kcal/mol), suggesting distinct mechanistic pathways. BSA denaturation assays demonstrated comparable IC50 values for EPMC (170.02 µg/mL), CA (171.48 µg/mL), and diclofenac sodium (165.05 µg/mL), whereas APMC exhibited weaker activity (215.06 µg/mL). In vivo, EPMC produced the most rapid and complete resolution of inflammation, achieving significantly lower area-under-curve values than diclofenac sodium (p < 0.05). Hematological analysis revealed mechanistic divergence: APMC (600 mg/kg) tended to normalize white blood cell (WBC) and lymphocyte counts, suggesting systemic immunomodulation, whereas EPMC and CA demonstrated localized anti-inflammatory action without hematological effects. Conclusion: EPMC demonstrates superior multi-modal anti-inflammatory activity through multi-target engagement and localized tissue action, positioning it as a promising lead for next-generation anti-inflammatory therapeutics with potentially improved safety profiles compared with conventional NSAIDs. Copyright © Korean Pharmacopuncture Institute. This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/4.0/) which permits unrestricted noncommercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Affiliations

Department of Pharmacy, Faculty of Science, Institut Teknologi Sumatera, South Lampung, Indonesia; Department of Cosmetic Engineering, Faculty of Industrial Technology, Institut Teknologi Sumatera, South Lampung, Indonesia; Department of Biology, Faculty of Science, Institut Teknologi Sumatera, South Lampung, Indonesia; Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Surabaya, Indonesia; Department of Medical Chemistry, Faculty of Medicine, Universitas Indonesia, Jakarta, Indonesia