Isolation and caracterization of Zerumbone isolated from Zingiber zerumbet
Abstract
Zerumbone is a cyclic sesquiterpene compound which is the main content of ethanol extract and lempuyang essential oil (Zingiber zerumbet). Zerumbone has been studied as a potential anticancer agent because it induces apoptosis and cycle inhibition while inhibiting invasion and metastasis. This research aims to isolate zerumbone from lempuyang wangi (Zingiber zerumbet) extract. The method used in this research includes isolation using column chromatography which allows a compound to be obtained in quite large quantities. Monitoring of the isolate extract was analyzed using Thin Layer Chromatography (TLC) under a UV lamp, monitoring of the isolate fraction using TLC under a UV lamp, then testing the purity of the zerumbone isolate using the UV-Vis spectrophotometer method, IR (Infrared) spectroscopy, TLC with different eluents , and LC-MS/MS, obtained the same compound isolation results between the isolate and the zerumbone standard with high purity, with a yield of 11% isolate.
References
A. Haque, I. Jantan, and H. Harikrishnan, “Zerumbone suppresses the activation of in fl ammatory mediators in LPS- stimulated U937 macrophages through MyD88-dependent NF- κ B / MAPK / PI3K-Akt signaling pathways,” Int. Immunopharmacol., vol. 55, pp. 312–322, 2018, doi: 10.1016/j.intimp.2018.01.001
Abdul, A.B.H., Al-Zubairi A.S., Tailan, N.D., Wahab, S.I.A., Zain, Z.N.M., Rulay, S., and Syam, M.M. 2008. Anticancer Activity of Natural Compound (Zerumbone) Extracted from Zingiber zerumbet in Human HeLa Cervical Cancer Cells. International Journal of Pharmacology. 4(3): 160-168.
Akhtar, N.M.Y., Jantan, I., Arshad, L., Haque, M.A., 2019. Standardized ethanol extract, essential oil and zerumbone of Zingiber zerumbet rhizome suppress phagocytic activity of human neutrophils. BMC Complement. Altern. Med. 19, 331. doi:10.1186/s12906-019-2748-5
Ariani, S. R. D., Septiana, N. and Falentina, S. 2021. Isolation and Identification of Essential Oils from Bitter Ginger (Zingiber amaricans Bl.), Fragrant Ginger (Zingiber aromaticum Val.) and Shampoo Ginger (Zingiber zerumbet (L.) Smith) Rhizomes Grown in Jumapolo Karanganyar Central Java Indonesia. JKPK (Jurnal Kim. dan Pendidik. Kim., vol. 6, no. 2, pp. 242– 251.
Ashraf, S.M., Sebastian, J., Rathinasamy, K., 2019. Zerumbone, a cyclic sesquiterpene, exerts antimitotic activity in HeLa cells through tubulin binding and exhibits synergistic activity with vinblastine and paclitaxel. Cell Prolif 52, e12558. doi:10.1111/cpr.12558
Avérous L. Polylactic Acid: Synthesis, Properties and Applications. In: Gemini MNB, editor. Monomers, Polymers and Composites from Renewable Resources. Amsterdam: Elsevier; 2008. p. 433-50.
Barathan, M., Vellasamy, K.M., Ibrahim, Z.A., Mariappan, V., Hoong, S.M., Vadivelu, J., 2021. Zerumbone mediates apoptosis and induces secretion of proinflammatory cytokines in breast carcinoma cell culture. Iran. J. Basic Med. Sci. 24, 1538–1545. doi:10.22038/IJBMS.2021.58573.13012
Chan, M.-L., Liang, J.-W., Hsu, L.-C., Chang, W.-L., Lee, S.-S., Guh, J.-H., 2015. Zerumbone, a ginger sesquiterpene, induces apoptosis and autophagy in human hormone-refractory prostate cancers through tubulin binding and crosstalk between endoplasmic reticulum stress and mitochondrial insult. Naunyn Schmiedebergs Arch. Pharmacol. 388, 1223–1236. doi:10.1007/s00210-015-1152-z
Chiang, P.-K., Tsai, W.-K., Chen, M., Lin, W.-R., Chow, Y.-C., Lee, C.-C., Hsu, J.-M., Chen, Y.-J., 2018. Zerumbone regulates DNA repair responding to ionizing radiation and enhances radiosensitivity of human prostatic cancer cells. Integr. Cancer Ther. 17, 292–298. doi:10.1177/1534735417712008
D. Hanwar, O. Elisafitri, and A. Suhendi, “Standardisasi Ekstrak Rimpang Lempuyang Gajah (Zingiber Zerumbet Smith),” 9th Univ. Res. Colloqium 2019, vol. 9, no. 1, pp. 345–351, 2019.
Deorukhkar, A., Ahuja, N., Mercado, A.-L., Diagaradjane, P., Raju, U., Patel, N., Mohindra, P., Diep, N., Guha, S., Krishnan, S., 2015. Zerumbone increases oxidative stress in a thiol-dependent ROS-independent manner to increase DNA damage and sensitize colorectal cancer cells to radiation. Cancer Med 4, 278–292. doi:10.1002/cam4.367
Diastuti, H., Asnani, A., Delsy, E.V.Y., Pamukasari, R. and Indriani, S., 2022. Toxicity and Antimicrobial Activity of Zerumbon from Zingiber zerumbet Rhizome. Molekul, 17(3), pp.328-334.
H. S. Rahman et al., “Biomedical properties of a natural dietary plant metabolite, Zerumbone, in cancer therapy and chemoprevention trials,” Biomed Res. Int., vol. 2014, 2014, doi: 10.1155/2014/920742.
Hamid, A., Lee, L.S., Karim, S.R., Jufri, N.F., 2018. Hepatoprotective Effects of Zerumbone against Paracetamol-Induced Acute Hepatotoxicity in Rats. Malays. J. Med. Sci. 25, 64–71. doi:10.21315/mjms2018.25.2.7
Ho, Y.-C., Lee, S.-S., Yang, M.-L., Huang-Liu, R., Lee, C.-Y., Li, Y.-C., Kuan, Y.-H., 2017. Zerumbone reduced the inflammatory response of acute lung injury in endotoxin-treated mice via Akt-NFκB pathway. Chem. Biol. Interact. 271, 9–14. doi:10.1016/j.cbi.2017.04.017
Hu, Z., Zeng, Q., Zhang, B., Liu, H., Wang, W., 2014. Promotion of p53 expression and reactive oxidative stress production is involved in zerumbone-induced cisplatin sensitization of non-small cell lung cancer cells. Biochimie 107 Pt B, 257–262. doi:10.1016/j.biochi.2014.09.001
Igarashi, Y., Ohnishi, K., Irie, K., Murakami, A., 2016. Possible Contribution of Zerumbone-Induced Proteo-Stress to Its Anti-Inflammatory Functions via the Activation of Heat Shock Factor 1. PLoS One 11, e0161282. doi:10.1371/journal.pone.0161282
Jalili-Nik, M., Afshari, A.R., Sabri, H., Bibak, B., Mollazadeh, H., Sahebkar, A., 2021. Zerumbone, a ginger sesquiterpene, inhibits migration, invasion, and metastatic behavior of human malignant glioblastoma multiforme in vitro. Biofactors 47, 729–739. doi:10.1002/biof.1756
Jalili-Nik, M., Sadeghi, M.M., Mohtashami, E., Mollazadeh, H., Afshari, A.R., Sahebkar, A., 2020. Zerumbone Promotes Cytotoxicity in Human Malignant Glioblastoma Cells through Reactive Oxygen Species (ROS) Generation. Oxid. Med. Cell. Longev. 2020, 3237983. doi:10.1155/2020/3237983
Jegannathan, S.D., Arul, S., Dayalan, H., 2022. Zerumbone Sensitizes the Anti-Cancer Efficacy of Cisplatin in Hepatocellular Carcinoma Cells. Anticancer Agents Med. Chem. doi:10.2174/1871520622666220324090801
Jorvig, J.E., Chakraborty, A., 2015. Zerumbone inhibits growth of hormone refractory prostate cancer cells by inhibiting JAK2/STAT3 pathway and increases paclitaxel sensitivity. Anticancer Drugs 26, 160–166. doi:10.1097/CAD.0000000000000171
Kim, A., Gwon, M.-H., Lee, W., Moon, H.-R., Yun, J.-M., 2022. Zerumbone suppresses high glucose and LPS-induced inflammation in THP-1-derived macrophages by inhibiting the NF-κB/TLR signaling pathway. Nutr. Res. 100, 58–69. doi:10.1016/j.nutres.2022.01.002
Kim, S., Kil, W.H., Lee, J., Oh, S.-J., Han, J., Jeon, M., Jung, T., Lee, S.K., Bae, S.Y., Lee, H.C., Lee, J.H., Yi, H.W., Kim, S.W., Nam, S.J., Lee, J.E., 2014. Zerumbone suppresses EGF-induced CD44 expression through the inhibition of STAT3 in breast cancer cells. Oncol. Rep. 32, 2666–2672. doi:10.3892/or.2014.3514
Kumar, S.C.S., Srinivas, P., Negi, P.S., Bettadaiah, B.K., 2013. Antibacterial and antimutagenic activities of novel zerumbone analogues. Food Chem. 141, 1097–1103. doi:10.1016/j.foodchem.2013.04.021
Kungsuwan A, Ittipong B, Chandrkrachang S. Preservative effect of chitosan on fish products. In: Steven WF, Rao MS, Chandrkachang S. editors. Chitin and Chitosan: Environmental and Friendly and Versatile Biomaterials. Bangkok: Asian Institute of Technology: 1996. p. 193-9.
L. Noviyanti Sutardi, I. Wientarsih, E. Handharyani, and A. Setiyono., 2015. Indonesian Wild Ginger (Zingiber sp) Extract: Antibacterial Activity against Mycoplasma gallisepticum. IOSR J. Pharm., vol. 5, no. 10, pp. 59– 64, [Online]. Available: www.iosrphr.org
Li, J., Wang, L., Sun, Y., Wang, Z., Qian, Y., Duraisamy, V., Antary, T.M.A., 2022. Zerumbone-induced reactive oxygen species-mediated oxidative stress re-sensitizes breast cancer cells to paclitaxel. Biotechnol. Appl. Biochem. doi:10.1002/bab.2326
M. A. Haque, I. Jantan, and H. Harikrishnan, “Zerumbone suppresses the activation of inflammatory mediators in LPS-stimulated U937 macrophages through MyD88-dependent NF-κB/MAPK/PI3K-Akt signaling pathways,” Int. Immunopharmacol., vol. 55, no. October 2017, pp. 312–322, 2018, doi: 10.1016/j.intimp.2018.01.001
M. Sulistyani and N. Huda, “Optimasi Pengukuran Spektrum Vibrasi Sampel Protein Menggunakan Spektrofotometer Fourier Transform Infra Red (Ftir),” Indones. J. Chem. Sci., vol. 6, no. 2, pp. 173–180, 2017.
Ma, S., Lei, Y., Zhang, L., Wang, J., 2018. Effects of zerumbone on proliferation and apoptosis of esophageal cancer cells and on P53 and Bcl-2 expression levels. Oncol. Lett. 16, 4379–4383. doi:10.3892/ol.2018.9184
Muenmee S, Chiemchaisri W, Chiemchaisri C. Microbial consortium involving biological methane oxidation in relation to the biodegradation of waste plastics in a solid waste disposal open dump site. International Biodeterioration and Biodegradation 2015;102:172-81.
Nobari, S., Najafi, R., Mahdavinezhad, A., Jalali, A., Amini, R., 2022. The Combination of Zerumbone with 5-Fluorouracil for Sensitizing Colorectal Cancer-Associated Fibroblasts to Treatment. Evid. Based Complement. Alternat. Med. 2022, 9369328. doi:10.1155/2022/9369328
Noor, Nur Farhanah Mohamad, and Sirat, Hasnah Mohd. 2016. Isolation, Characterization, and Modification of Zerumbone form Zingiber zerumbet. eProsidings Chemistry
Orzel C. Wind and Temperature: Why Doesn’t Windy Equal Hot? [Internet]. 2010 [cited 2016 Jun 20]. Available from: http://scienceblogs.com/principles/2010/08/17/wind-and-temperature-why-doesn/.
Overview of Liquid Chromatography-Mass Spectroscopy Instrumentation,” Pharm. Methods, vol. 5, no. 2, pp. 47–55, doi: 10.5530/phm.2014.2.2
R. M. Silverstein, F. X. Webster, and D. J. 2015. Spectrometric Identification of Organic Compounds, 8th ed. New York: John Wiley & Sons, Inc
Rahman, H.S., Rasedee, A., Chartrand, M.S., Othman, H.H., Yeap, S.K., Namvar, F., 2014. Zerumbone induces G2/M cell cycle arrest and apoptosis via mitochondrial pathway in Jurkat cell line. Nat Prod Commun 9, 1237–1242.
Riyanto, S., 2007. Identification of the isolated compounds from Zingiber amaricans BL. Rhizome. Indonesian Journal of Chemistry, 7(1), pp.93-96.
S. Lallo, S. Kasim, R. Tayeb, A. D. Hasan, H. Sere, and T. Arifin, “Analisis Zerumbone dalam Zingiber zerumbet dan Aktivitas Penghambatannya terhadap Bakteri Mycobacterium tuberculosis,” vol. 4, no. 2, pp. 126–132, 2018, doi: 10.22487/j24428744.2018.v4.i2.11138.
S. Parasuraman, A. Rao, S. Balamurugan, S. Muralidharan, K. Jayaraj Kumar, and V. Vijayan, “An
Schnoell, J., Stanisz, I., Jank, B.J., Stanek, V., Schmid, R., Brunner, M., Heiduschka, G., Kotowski, U., 2022. Zerumbone acts as a radiosensitizer in head and neck squamous cell carcinoma. Invest. New Drugs 40, 224–231. doi:10.1007/s10637-021-01190-7
Sf, A., Maharjan, R., 2018. Immunomodulation of Zerumbone via Decreasing the Production of Reactive Oxygen Species from Immune Cells. Pak. J. Biol. Sci. 21, 475–479. doi:10.3923/pjbs.2018.475.479
Shamoto, T., Matsuo, Y., Shibata, T., Tsuboi, K., Nagasaki, T., Takahashi, H., Funahashi, H., Okada, Y., Takeyama, H., 2014. Zerumbone inhibits angiogenesis by blocking NF-κB activity in pancreatic cancer. Pancreas 43, 396–404. doi:10.1097/MPA.0000000000000039
Shieh, Y.-H., Huang, H.-M., Wang, C.-C., Lee, C.-C., Fan, C.-K., Lee, Y.-L., 2015. Zerumbone enhances the Th1 response and ameliorates ovalbumin-induced Th2 responses and airway inflammation in mice. Int. Immunopharmacol. 24, 383–391. doi:10.1016/j.intimp.2014.12.027
Shrestha MK. Relative ungulate abundance in a fragmented landscape: implications for tiger conservation [dissertation]. Saint Paul, University of Minnesota; 2004.
Sidahmed, H.M.A., Hashim, N.M., Abdulla, M.A., Ali, H.M., Mohan, S., Abdelwahab, S.I., Taha, M.M.E., Fai, L.M., Vadivelu, J., 2015. Antisecretory, gastroprotective, antioxidant and anti-Helicobcter pylori activity of zerumbone from Zingiber zerumbet (L.) Smith. PLoS One 10, e0121060. doi:10.1371/journal.pone.0121060
Su, C.-C., Wang, S.-C., Chen, I.-C., Chiu, F.-Y., Liu, P.-L., Huang, C.-H., Huang, K.-H., Fang, S.-H., Cheng, W.-C., Huang, S.-P., Yeh, H.-C., Liu, C.-C., Lee, P.-Y., Huang, M.-Y., Li, C.-Y., 2021. Zerumbone Suppresses the LPS-Induced Inflammatory Response and Represses Activation of the NLRP3 Inflammasome in Macrophages. Front. Pharmacol. 12, 652860. doi:10.3389/fphar.2021.652860
Suhartati. 2017. Dasar-Dasar Spektrofotometer UV-Vis dan Spektrofotometri Massa untuk Penentuan Struktur Senyawa Organik. Lampung:Aura Publishing.
T. P. L. Sudarwati and M. A. H. F. Fernanda, Aplikasi Pemanfaatan Daun Pepaya (Carica papaya) Sebagai Biolarvasida Terhadap Larva Aedes aegypti, Pertama. Graniti, 2019.
Tan, J.W., Israf, D.A., Tham, C.L., 2018. Major Bioactive Compounds in Essential Oils Extracted From the Rhizomes of Zingiber zerumbet (L) Smith: A Mini-Review on the Anti-allergic and Immunomodulatory Properties. Front. Pharmacol. 9, 652. doi:10.3389/fphar.2018.00652
Tom Tyner. 2017. “‘ACS Reagent Chemicals’ Expands.” C&EN Global Enterprise 95(32): 34–34.
Tsuboi, K., Matsuo, Y., Shamoto, T., Shibata, T., Koide, S., Morimoto, M., Guha, S., Sung, B., Aggarwal, B.B., Takahashi, H., Takeyama, H., 2014. Zerumbone inhibits tumor angiogenesis via NF-κB in gastric cancer. Oncol. Rep. 31, 57–64. doi:10.3892/or.2013.2842
Tyree MT, Zimmermann MH. Xylem structure and the ascent of sap. Heidelberg, Germany: Springer; 2002.
United Nations Environment Programme (UNEP). SDGs and The Environment [Internet]. 2015 [cited 2016 Jun 7]. Available from: http://web.unep.org/post2015
USDA, “Plants Database,” United States Department of Agriculture, 2023. https://plants.sc.egov.usda.gov/home/plantProfile?symbol=ZIZE (accessed Okt. 25, 2023).
W. F. Dewatisari, L. Rumiyanti, and I. Rakhmawati, “Rendemen dan Skrining Fitokimia pada Ekstrak Daun Sanseviera sp.,” Jurnal Penelitian Pertanian Terapan, vol. 17, no. 3, p. 197, Jan. 2018, doi: 10.25181/jppt.v17i3.336.
Wahyuni, S.R.I, Bermawie, N. and Kristina, N. 2013. “Morphological 67 Characteristic, Yield Potential, and Major Rhizome Constituent of Nine Accession,” J. Littri, vol. 19, no. September, pp. 99–107
Wang, M., Niu, J., Ou, L., Deng, B., Wang, Y., Li, S., 2019b. Zerumbone Protects against Carbon Tetrachloride (CCl4)-Induced Acute Liver Injury in Mice via Inhibiting Oxidative Stress and the Inflammatory Response: Involving the TLR4/NF-κB/COX-2 Pathway. Molecules 24. doi:10.3390/molecules24101964
WHO. 2011. Quality Control Methods for Herbal Materials. Switzerland: WHO Press.
Willmott CJ, Ackleson SG, Davis RE, Feddema JJ, Klink KM, Legates DR, Donnell JO, Rowe CM. Statistics for the evaluation and comparison of models. Journal of Geophysical Research 1985;90(C5):8995-9005.
Wiwattanakantang P, To-im J. Tourist satisfaction on sustainable tourism development, amphawa floating marketSamut songkhram, Thailand. Proceedings of the 1st Environment and Natural Resources International Conference; 2014 Nov 6–7; The Sukosol hotel, Bangkok: Thailand; 2014.
Yang, H.-L., Lee, C.-L., Korivi, M., Liao, J.-W., Rajendran, P., Wu, J.-J., Hseu, Y.-C., 2018. Zerumbone protects human skin keratinocytes against UVA-irradiated damages through Nrf2 induction. Biochem. Pharmacol. 148, 130–146. doi:10.1016/j.bcp.2017.12.014
Zainal, N.S., Gan, C.P., Lau, B.F., Yee, P.S., Tiong, K.H., Abdul Rahman, Z.A., Patel, V., Cheong, S.C., 2018. Zerumbone targets the CXCR4-RhoA and PI3K-mTOR signaling axis to reduce motility and proliferation of oral cancer cells. Phytomedicine 39, 33–41. doi:10.1016/j.phymed.2017.12.011