Isolation and Modification of Ethyl-p-Methoxycinnamate from Kaempferia galanga and Its Antioxidant Activity

Vidia Afina Nuraini, Farah Azizah Hanan, Iqbal Mustapha


Oxidative stress has been associated with the development of many diseases. Kaempferia galanga, also known as aromatic ginger, is widely distributed in Asian countries, including Indonesia, and has been traditionally used as an herbal medicine to treat various ailments. Its main constituent, ethyl-p-methoxycinnamate (EPMC), has been reported to exhibit various biological activities, including anticancer, anti-inflammatory, and antituberculosis. However, there has been little research on the antioxidant activity of EPMC. Therefore, this study aimed to investigate the antioxidant properties of EPMC isolated from the rhizome of K. galanga and its hydrolyzed compound. EPMC was successfully isolated from the n-hexane extract of K. galanga in a 5.88% yield. Hydrolysis of EPMC under basic conditions resulted in p-methoxycinnamic acid (PMCA) in a 21% yield. Results of in vitro antioxidant assay showed that PMCA gave stronger scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with an IC50 value of 518.58 ppm compared to EPMC (IC50 >1000 ppm). These results featured the importance of the hydroxyl group in enhancing the antioxidant properties of EPMC.

Kata Kunci

Antioxidant activity; ethyl-p-methoxycinnamate; hydrolysis; Kaempferia galanga; p-methoxycinnamic acid

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S.-Y. Wang, L. Cai, N. Yang, F.-F. Xu, Y.-S. Wu, and B. Liu, “Chemical composition of the Kaempferia galanga L. essential oil and its in vitro and in vivo antioxidant activities,” Front. Nutr., vol. 10, p. 1080487, 2023.

H. J. Forman and H. Zhang, “Targeting oxidative stress in disease: promise and limitations of antioxidant therapy,” Nat Rev Drug Discov, vol. 20, no. 9, pp. 689–709, 2021.

Y. S. Y. Yeap, N. K. Kassim, R. C. Ng, G. C. L. Ee, L. Saiful Yazan, and K. H. Musa, “Antioxidant properties of ginger (Kaempferia angustifolia Rosc.) and its chemical markers,” Int J Food Prop., vol. 20, no. sup1, pp. 1158–1172, 2017.

B. Halliwell, “Understanding mechanisms of antioxidant action in health and disease,” Nat Rev Mol Cell Biol, 2023.

A. I. Casas et al., “On the Clinical Pharmacology of Reactive Oxygen Species,” Pharmacol Rev, vol. 72, no. 4, pp. 801–828, 2020.

R. Sarangarajan, S. Meera, R. Rukkumani, P. Sankar, and G. Anuradha, “Antioxidants: Friend or foe?,” Asian Pac J Trop Med., vol. 10, no. 12, pp. 1111–1116, 2017.

A. Singh et al., “The industrially important genus Kaempferia: An ethnopharmacological review,” Front. Pharmacol., vol. 14, p. 1099523, 2023.

J. Techaprasan, S. Klinbunga, C. Ngamriabsakul, and T. Jenjittikul, “Genetic variation of Kaempferia (Zingiberaceae) in Thailand based on chloroplast DNA(psbA-trnH and petA-psbJ) sequences,” Genet. Mol. Res., vol. 9, no. 4, pp. 1957–1973, 2010.

N. Khanh Pham, H. Tuan Nguyen, and Q. Binh Nguyen, “A review on the ethnomedicinal uses, phytochemistry and pharmacology of plant species belonging to Kaempferia genus (Zingiberaceae),” Pharm Sci Asia, vol. 48, no. 1, pp. 1–24, 2021.

A. Kumar, “Phytochemistry, pharmacological activities and uses of traditional medicinal plant Kaempferia galanga L. – An overview,” J Ethnopharmacol, vol. 253, p. 112667, 2020.

A. Hashiguchi, M. San Thawtar, T. Duangsodsri, M. Kusano, and K. N. Watanabe, “Biofunctional properties and plant physiology of Kaempferia spp.: Status and trends,” J Funct Foods, vol. 92, p. 105029, 2022.

M. I. Umar et al., “Bioactivity-guided isolation of ethyl-p-methoxycinnamate, an anti-inflammatory constituent, from Kaempferia galanga L. extracts,” Molecules, vol. 17, no. 7, pp. 8720–8734, 2012.

A. Amuamuta, T. Plengsuriyakarn, and K. Na-Bangchang, “Anticholangiocarcinoma activity and toxicity of the Kaempferia galanga Linn. rhizome ethanolic extract,” BMC Complement Altern Med, vol. 17, no. 1, p. 213, 2017.

P. N. Fauziyah, E. Y. Sukandar, and D. K. Ayuningtyas, “Combination effect of antituberculosis drugs and ethanolic extract of selected medicinal plants against multi-drug resistant Mycobacterium tuberculosis isolates,” Sci. Pharm., vol. 85, no. 1, p. 14, 2017.

K. Kochuthressia and S. Britto, “In vitro antimicrobial evaluation of Kaempferia galanga L. rhizome extract,” AJBMS, vol. 2, no. 1, pp. 1–5, 2012.

P. C. Jagadish, K. P. Latha, J. Mudgal, and G. K. Nampurath, “Extraction, characterization and evaluation of Kaempferia galanga L. (Zingiberaceae) rhizome extracts against acute and chronic inflammation in rats,” J Ethnopharmacol, vol. 194, pp. 434–439, 2016.

H. Ali, R. Yesmin, M. A. Satter, R. Habib, and T. Yeasmin, “Antioxidant and antineoplastic activities of methanolic extract of Kaempferia galanga Linn. rhizome against Ehrlich ascites carcinoma cells,” J King Saud Univ Sci., vol. 30, no. 3, pp. 386–392, 2018.

R. Othman, H. Ibrahim, M. A. Mohd, M. R. Mustafa, and K. Awang, “Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L.,” Phytomedicine, vol. 13, no. 1–2, pp. 61–66, 2006.

Elshamy et al., “Recent advances in Kaempferia phytochemistry and biological activity: A comprehensive review,” Nutrients, vol. 11, no. 10, p. 2396, 2019.

W. Ridtitid, C. Sae-wong, W. Reanmongkol, and M. Wongnawa, “Antinociceptive activity of the methanolic extract of Kaempferia galanga Linn. in experimental animals,” J Ethnopharmacol. vol. 118, no. 2, pp. 225–230, 2008.

S. Lallo, B. Hardianti, S. Sartini, I. Ismail, D. Laela, and Y. Hayakawa, “Ethyl p-methoxycinnamate: an active anti-metastasis agent and chemosensitizer targeting NFκB from Kaempferia galanga for melanoma cells,” Life, vol. 12, no. 3, p. 337, 2022.

D. Lakshmanan et al., “Ethyl p-methoxycinnamate isolated from a traditional anti-tuberculosis medicinal herb inhibits drug resistant strains of Mycobacterium tuberculosis in vitro,” Fitoterapia, vol. 82, no. 5, pp. 757–761, 2011.

M. I. Umar et al., “Ethyl-p-methoxycinnamate isolated from Kaempferia galanga inhibits inflammation by suppressing interleukin-1, tumor necrosis factor-α, and angiogenesis by blocking endothelial functions,” Clinics, vol. 69, no. 2, pp. 134–144, 2014.

R. Farhoosh, S. Johnny, M. Asnaashari, N. Molaahmadibahraseman, and A. Sharif, “Structure–antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid,” Food Chem., vol. 194, pp. 128–134, 2016.



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