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 SM, Musa AM, Abdullahi M, Sule M, Sani YM. 2013. Isolation of lupeol from the stem-bark of Loncho carpussericeus (Papilionaceae). Sch Acad J Biosci 1:18-19.
Ahmed Hamdi OA, Lo Y, Alfarizal MN, Kamarudin M, Hazni H, Paydar M, Looi CY, Shilpi JA, Kadir HA, Awang K. 2015. Neuroprotective and antioxidant constituents from Curcuma zedoaria rhizomes. Rec Nat Prod 9: 349-355.
Carlsen MH, Halvorsen BL, Holte K, Bøhn SK, Dragland S, Sampson L, Willey C, Senoo H, Umezono Y, Sanada C, Barikmo I, Berhe1 N, Willett WC, Phillips KM, Jacobs Jr DR, Blomhoff R. 2010.The total antioxidant content of more than 3100 foods, beverages, spices, herbs and supplements used worldwide. Nutrition J 9: 2-11.
Damodaran NP, Dev S. 1965. Stereochemistry of zerumbone. Tetrahed 6: 1977-1981.
Damodaran NP, Dev S. 1968a. Studies in sesquiterpenes-XXXVII. Sesquiterpenoids from the essential oil of Zingiber zerumbet Smith. Tetrahed 24: 4113-4122.
Dev S. 1960. Sesquiterpenes. XVI. Zerumbone, a monocyclic sesquiterpene ketone. Tetrahed 8: 171-180.
Fidyt K, Fiedorowicz A, Strza L, Szumny A. 2016. â-caryophyllene and â-caryophyllene oxidenatural compounds of anticancer and analgesic properties. Cancer Med 5: 3007– 3017.
Finose A, Gopalakrishnan VK. 2014. Antioxidant potential of Zingiber nimmonii (j. graham) Dalzell. Int J Pharm Pharm Sci 6: 50-52.
Garrat DC. 1964. The Quantitative analysis of Drugs. Chapman and Hall Ltd., Japan 3: 456 458.
Govindarajan M, Rajeswary M, Arivoli S, Tennyson S, Giovanni B. 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? Parasitol Res 115: 1807-1816.
Güner OF. 2002. History and evolution of the pharmacophore concept in computer-aided drug design. Curr Top Med Chem 2: 1321- 1332.
Jang S, Ah-Reum Han, Park G. GiI-Ja Jhon, Eun-Kyoung Seo. 2004. Flavonoids and aromatic compounds from the rhizomes of Zingiber zerumbet. Arch Pharm Res 27: 386-389.
Konickal MPK, Gopinathan RA, Mamiyil S, Indira B. 2013. Ancient Sci Life 32: 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 Chem 105: 548–554.
Mabberley DJ. 1990. The Plant-Book: A Portable Dictionary of the Higher Plants. Cambridge University Press, Cambridge, p. 623.
Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Evans C R. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 26: 1231–1237.
Rodrigues F, Maniscalco DA, Silva FAJ, Chiari BG, Castelli MV, Isaac VLB, Cicarelli RMB, López SN. 2017. Trypanocidal activity of flavokawin B, a component of Polygonum ferrugineum Wedd. Planta Med 83: 239-244.
Sabu M. 2003. Revision of the genus Zingiber in South India. Folia Malaysiana 4: 25–52.
Sabulal M, Dan R. Kurup, Sukumaran N, Krishna R, George V. 2006. Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity. Phytochem 67: 2469- 2473.
Soobrattee MA, Neergheen VS, Luximon-Ramma A, Aruoma OI, Bahorun T. 2005. Phenolics as potential antioxidant therapeutic agents: mechanism and actions. Mut Res 579: 200- 213.
Voet R, Kumar A, Zhang KYJ. 2014. Combining in silico and in cerebro approaches for virtual screening and pose prediction in SAMPL4. J Comp Aided Mol Des 28: 363-373.
Wermuth CG, Lindberg P, Ganellin CR, Mitscher LA. 1998. Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998). Pure Appl Chem 70: 1129-1143.
Won SJ, Liu CT, Tsao LT, Weng JR, Ko HH, Wang JP, Lin CN. 2005. Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem 40: 103–112.
Zhang YJ, Gan RY, Li S, Zhou Y, Li AN, Xu DP, Li HB. 2015. Antioxidant phytochemicals for the prevention and treatment of chronic diseases. Molecules 20: 21138-21156.
© CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow-226015
Greeshma Gopalan, Hridya V Kavunkal, Devika S Ravindran, Sabu Mamiyil, Shibi IG, Radhakrishnan KV. 2021. Chemical constituents and their bioactivities of Zingiber nimmonii: An endemic species in South India. J Med Aromat Plant Sci 43: 15-24.
