Volume: 43 Issue: 1
Chemical constituents and their bioactivities of Zingiber nimmonii: An endemic species in South India
Year: 2021, Page: 15-24, Doi: https://doi.org/10.62029/jmaps.v43i1.Gopalan
Received: June 11, 2021 Accepted: June 24, 2021 Published: July 1, 2021
Eight major compounds were isolated and characterised from the rhizomes of Zingiber nimmonii (J. Graham) Dalzell by chromatographic and spectroscopic techniques. The compounds characterised by recording its Nuclear Magnetic Resonance Spectra (1D NMR, 2D NMR) together with Mass Spectra under ESI/HRMS and IR Spectra. The major compounds characterized as galangin3-O-methyl ether (1), galangin-3,7-di-O-methyl ether (2), ß-caryophyllene (3), α-humulene (4), zerumbone (5), germacrone (6), flavokavain B (7) and lupeol (8). Comparative DPPH scavenging, ABTS scavenging and NO scavenging assays of Zingiber nimmonii were carried out in both extracts and molecular level so as the consumption of this herb can regulate the free radicals produced in our body through various metabolic pathways. The compound, flavokavain B displayed better scavenging of DPPH radicals with IC50 values of 30.21 ± 0.111 µM, the compound, germacrone showed better scavenging of ABTS with an IC50 values of 51.7189 ± 0.688 µM, and the compound, zerumbone exhibited better IC50 value against the nitric oxide radicals with IC50 value of 97.876 ± 0.853 µM. The effects of inhibitory actions of the isolated compounds were also carried out for their virtual screening of antidiabetic and anticancer activities. The compounds 1 and 2 were effectively bound to the active sites of the enzymes with a docking score of -11.2018kcal/mol and -11.2703 kcal/mol respectively for the enzyme 2ITW and, -13.1593 kcal/mol and -11.9667 kcal/mol respectively for the enzyme 3A4A.
Keywords: Antioxidative activity, Molecular docking, Zerumbone, Zingiber nimmonii, -humulene, -caryophyllene
Abdullahi, S. M., Musa, A. M., Abdullahi, M., Sule, M., & Sani, Y. M. (2013). Isolation of lupeol from the stem-bark of Lonchocarpus sericeus (Papilionaceae). Scholarly Academic Journal of Biosciences, 1, 18–19.
Ahmed Hamdi, O. A., Lo, Y., Alfarizal, M. N., Kamarudin, M., Hazni, H., Paydar, M., Looi, C. Y., Shilpi, J. A., Kadir, H. A., & Awang, K. (2015). Neuroprotective and antioxidant constituents from Curcuma zedoaria rhizomes. Records of Natural Products, 9, 349–355.
Carlsen, M. H., Halvorsen, B. L., Holte, K., Bøhn, S. K., Dragland, S., Sampson, L., Willey, C., Senoo, H., Umezono, Y., Sanada, C., Barikmo, I., Berhe, N., Willett, W. C., Phillips, K. M., Jacobs Jr., D. R., & Blomhoff, R. (2010). The total antioxidant content of more than 3100 foods, beverages, spices, herbs and supplements used worldwide. Nutrition Journal, 9, 2–11.
Damodaran, N. P., & Dev, S. (1965). Stereochemistry of zerumbone. Tetrahedron, 6, 1977–1981.
Damodaran, N. P., & Dev, S. (1968a). Studies in sesquiterpenes—XXXVII. Sesquiterpenoids from the essential oil of Zingiber zerumbet Smith. Tetrahedron, 24, 4113–4122.
Dev, S. (1960). Sesquiterpenes. XVI. Zerumbone, a monocyclic sesquiterpene ketone. Tetrahedron, 8, 171–180.
Fidyt, K., Fiedorowicz, A., Strzał, Ł., & Szumny, A. (2016). β-caryophyllene and β-caryophyllene oxide—natural compounds with anticancer and analgesic properties. Cancer Medicine, 5, 3007–3017.
Finose, A., & Gopalakrishnan, V. K. (2014). Antioxidant potential of Zingiber nimmonii (J. Graham) Dalzell. International Journal of Pharmacy and Pharmaceutical Sciences, 6, 50–52.
Garratt, D. C. (1964). The quantitative analysis of drugs. Chapman and Hall Ltd.
Govindarajan, M., Rajeswary, M., Arivoli, S., Tennyson, S., & Benelli, G. (2016). Larvicidal and repellent potential of Zingiber nimmonii (J. Graham) Dalzell (Zingiberaceae) essential oil: An eco-friendly tool against malaria, dengue, and lymphatic filariasis mosquito vectors. Parasitology Research, 115, 1807–1816.
Güner, O. F. (2002). History and evolution of the pharmacophore concept in computer-aided drug design. Current Topics in Medicinal Chemistry, 2(12), 1321–1332.
Jang, D. S., Han, A.-R., Park, G., Jhon, G.-J., & Seo, E.-K. (2004). Flavonoids and aromatic compounds from the rhizomes of Zingiber zerumbet. Archives of Pharmacal Research, 27(4), 386–389.
Konickal, M. P. K., Gopinathan, R. A., Mamiyil, S., & Indira, B. (2013). Significance of gingers (Zingiberaceae) in Indian System of Medicine—Ayurveda: An overview. Ancient Science of Life, 32(4), 253–261.
Liu, X., Dong, M., Chen, X., Jiang, M., Lv, X., & Yan, G. (2007). Antioxidant activity and phenolics of an endophytic Xylaria sp. from Ginkgo biloba. Food Chemistry, 105(2), 548–554.
Mabberley, D. J. (1990). The plant-book: A portable dictionary of the higher plants. Cambridge University Press.
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9–10), 1231–1237.
Rodrigues, F. D., Maniscalco, D. A., Silva, F. A. J., Chiari, B. G., Castelli, M. V., Isaac, V. L. B., Cicarelli, R. M. B., & López, S. N. (2017). Trypanocidal activity of flavokawin B, a component of Polygonum ferrugineum Wedd. Planta Medica, 83(3–4), 239–244.
Sabu, M. (2003). Revision of the genus Zingiber in South India. Folia Malaysiana, 4(1), 25–52.
Sabulal, B., Dan, M., Kurup, R., Pradeep, N. S., Valsamma, R. K., & George, V. (2006). Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity. Phytochemistry, 67(22), 2469–2473.
Soobrattee, M. A., Neergheen, V. S., Luximon-Ramma, A., Aruoma, O. I., & Bahorun, T. (2005). Phenolics as potential antioxidant therapeutic agents: Mechanism and actions. Mutation Research, 579(1–2), 200–213.
Voet, A. R. D., Kumar, A., Berenger, F., & Zhang, K. Y. J. (2014). Combining in silico and in cerebro approaches for virtual screening and pose prediction in SAMPL4. Journal of Computer-Aided Molecular Design, 28(4), 363–373.
Wermuth, C. G., Lindberg, P., Ganellin, C. R., & Mitscher, L. A. (1998). Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998). Pure and Applied Chemistry, 70(5), 1129–1143.
Won, S.-J., Liu, C.-T., Tsao, L.-T., Weng, J.-R., Ko, H.-H., Wang, J.-P., & Lin, C.-N. (2005). Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. European Journal of Medicinal Chemistry, 40(2), 103–112.
Zhang, Y.-J., Gan, R.-Y., Li, S., Zhou, Y., Li, A.-N., Xu, D.-P., & Li, H.-B. (2015). Antioxidant phytochemicals for the prevention and treatment of chronic diseases. Molecules, 20(12), 21138–21156.
© CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow-226015
Gopalan, G., Kavunkal, H. V., Ravindran, D. S., Mamiyil, S., Shibi, I. G., & Radhakrishnan, K. V. (2021). Chemical constituents and their bioactivities of Zingiber nimmonii: An endemic species in South India. Journal of Medicinal Aromatic Plant Sciences, 43(1), 15–24.
