Isolation and Characterization of Curcumenotone, a Sesquiterpene from Curcuma aeruginosa Roxb as Antioxidant
Keywords:
Bioassay Guided Isolation, Curcuma aeruginosa, Antioxidant, Sesquiterpenes, Curcumenotone
Abstract
Antioxidant compounds are necessary to block the initiation of oxidation chain reactions and inhibit the formation of ROS which are the cause of various diseases. Natural antioxidants can be isolated from various sources, one of them from Curcuma aeruginosa Roxb Rhizome. This study was aimed to isolate and identify antioxidant compounds from Curcuma aeruginosa Roxb rhizome. To isolate the active compound, the 2,2-diphenyl-1-picrylhidrazyl (DPPH) free radical scavenging activity guide was used. Initially the Curcuma aeruginosa Roxb rhizome powdered material macerated with ethanol 70% to give ethanol extract (EE). The EE was then fractionated gradually with increasing polarity solvents to give n-hexane (HF), ethyl acetate (EAF), ethanol (EF) and insoluble (IF) fractions. The EF was the active fraction, was fractionated into 6 fractions (EE.a-f) based on their TLC picture. Two compounds (EF.a1 and EF.a2) were isolated from active fraction (EF.a) by preparative TLC. The EF.a2 appeared as white crystals demonstrates better activity as anti radical DPPH, having 96.24% purity (HPLC). EF.a2 appeared as a single peak in GC (Rt 12,78), and having molecular weight at m/z 234. There were 2 absorbtion peaks at 226 nm and 260 nm in Uv-Vis spectrophotometer and absorption bands at 3364, 3314, 2905 and 1653 cm-1 on the FT-IR spectrum. Based on spectroscopic data (1H-,13C-NMR) and comparison with reported data, the EF.a2 was identified as sesquiterpene, curcumenotone (C15H22O2). The curcumenotone was shown potent antioxidant in DPPH radical scavenging assay had an IC50 53.24±1.51 µg/mL, ABTS radical scavenging assay had an IC50 41.33±3.15 µg/mL, and FRAP assay had an IC50 37,82±2.02 µg/mL.
References
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Sugita, P., Octaviana, N., Wukirsari, T., & Rahayu, D. U. . (2018). Chemical Constituent and Antioxidant Activity of Methanol Extract from Indonesian Curcuma aeruginosa Roxb. Rhizome. Journal of Pharmacy Research, 10(1), 293–297.
Suharsanti, R., N, S., E, L., & Rahardhian MRR. (2019). Potency of Belimbing Wuluh (Averrhoa bilimbi) as Antioxidant and Tyrosinase Inhibitor For Skin Whitening Products. Journal Of Pharma Research, 8(4), 151–154.
Suphrom, N., Pumthong, G., Khorana, N., Waranuch, N., Limpeanchob, N., & Ingkaninan, K. (2012). Anti-Androgenic Effect of Sesquiterpenes Isolated from The Rhizomes of Curcuma aeruginosa Roxb. Fitoterapia, 83(5), 864–871.
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Atun, S., Arianingrum, R., Aznam, N., & Malek, S. N. A. (2016). Isolation of Sesquiterpenes Lactone from Curcuma Aeruginosa Rhizome and The Cytotoxic Activity Against Human Cancer Cell Lines. International Journal of Pharmacognosy and Phytochemical Research, 8(7), 1168–1172.
Benzie, I. F. F., & Strain, J. J. (1996). The Ferric Reducing Ability of Plasma (FRAP) as a Measure of “Antioxidant Power”: The FRAP Assay. Analytical Biochemistry, 239(1), 70–76. https://doi.org/10.1006/ABIO.1996.0292
Boutsada, P., Giang, V. H., Linh, T. M., Mai, N. C., Cham, P. T., Hanh, T. T. H., Phonenavong, K., Sengchanh, S., Cuong, N. X., Lien, L. Q., & Ban, N. K. (2018). Sesquiterpenoids from The Rhizomes of Curcuma aeruginosa. Vietnam Journal of Chemistry, 56(6), 721–725.
Fitria, R., Seno, D. S. H., Priosoeryanto, B. P., Hartanti, & Nurcholis, W. (2019). Volatile Compound Profiles and Cytotoxicity in Essential Oils from Rhizome of Curcuma Aeruginosa and Curcuma zanthorrhiza. Biodiversitas, 20(10), 2943–2948.
Hamdi, O. A. A., Ye, L. J., Kamarudin, M. N. A., 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(3), 349–355.
Hastuti, B., Ibrahim, S., & Efdi, M. (2016). Isolation Structure and Elucidation of Flavone from Temu Hitam Rhizome (Curcuma aeruginosa Roxb.). Journal of Chemical and Pharmaceutical Research, 8(5), 302–304.
Hossain, C. F., Al-Amin, M., Sayem, A. S. M., Siragee, I. H., Tunan, A. M., Hassan, F., Kabir, M. M., & Sultana, G. N. N. (2015). Antinociceptive Principle from Curcuma aeruginosa. BMC Complementary and Alternative Medicine, 15(1), 1–7.
Istyastono, E. P., Margono, S. A., & Pranowo, H. D. (2003). The Keto-Enol Tautomerism of Curcumin and Some 4-substituted Curcumin Derivatives : A Theoretical Study Based on Computational Chemistry Approach. Indonesian Journal of Pharmacy, 14(3), 107–113.
Mistriyani, Riyanto, S., Windarsih, A., & Rohman, A. (2021). Antioxidant Activities and Identification of An Active Compound from Rambutan (Nephelium Lappaceum L.) Peel. Indonesian Journal of Chemistry, 21(2), 259–267.
Mukherjee, S., Pawar, N., Kulkarni, O., Nagarkar, B., Thopte, S., Bhujbal, A., & Pawar, P. (2011). Evaluation of Free-Radical Quenching Properties of Standard Ayurvedic Formulation Vayasthapana Rasayana. BMC Complementary and Alternative Medicine, 11.
Myint, K. (2006). Isolation and Characterization of Phytoconstituents from Myanmar Medicinal Plants. Martin Luther Universität Halle Wittenberg.
Nisar, T., Iqbal, M., Raza, A., Safdar, M., Iftikhar, F., & Waheed, M. (2015). Estimation of Total Phenolics and Free Radical Scavenging of Turmeric (Curcuma longa). American-Eurasian J. Agric. & Environ. Sci, 15(7), 1272–1277.
Nurcholis, W., Khumaida, N., Syukur, M., & Bintang, M. (2016). Variability of Total Phenolic and Flavonoid Content and Antioxidant Activity Among 20 Curcuma Aeruginosa Roxb. Accessions of Indonesia. Asian Journal of Biochemistry, 11(3), 142–148.
Patel, S. B., Attar, U. A., & Ghane, S. G. (2018). Antioxidant Potential of Wild Lagenaria siceraria (Molina) Standl. Thai Journal of Pharmaceutical Sciences (TJPS), 42(2), 90–96.
Pham, T. O., Nguyen, T. T., Do, T. X., Le, T. H., Opeyemi, N. A., & Isiaka, A. O. (2018). The Rhizome Essential Oil of Curcuma Aeruginosa Roxb. (Zingiberaceae) from Vietnam. Trends in Phytochemical, 2(3), 179–184.
Pourmorad, F., Hosseinimehr, S., & Shahabimajd, N. (2002). Antioxidant Activity, Phenol and Flavonoid Contents of Some Selected Iranian Medicinal Plants. African Journal of Biotechnology, 5(11), 1143–1145.
Rahardhian, M. R. R., & Suharsanti, R. (2019). Potency of Purification Extract from Belimbing Wuluh (Averrhoa Bilimbi) as Antioxidant and Anti-Tyrosinase. Journal of Pharma Research, 8(5), 318–322.
Rahayu, D. U. C., Hartono, & Sugita, P. (2018). Antibacterial Activity of Curcumenol From Rhizomes of Indonesian Curcuma aeruginosa (Zingiberaceae). Rasayan Journal of Chemistry, 11(2), 762–765.
Rajurkar, N., & Hande, S. M. (2011). Estimation of Phytochemical Content and Antioxidant Activity of Some Selected Traditional Indian Medicinal Plants. Indian Journal of Pharmaceutical Sciences, 73(2), 146.
Saputra, R. R., & Kalalinggi, S. Y. (2022). Pengaruh Gugus Terhadap Kesetimbangan Keto Enol pada Senyawa Turunan Kurkumin. Bohr: Jurnal Cendekia Kimia, 1(01), 42–52.
Setiawan, V., Phangestu, S., Grace Soetikno, A., Arianti, A., & Kohar, I. (2021). Rapid Screening Analysis of Antioxidant Activities in Green Tea Products Using DPPH and FRAP. Pharmaceutical Journal of Indonesia, 7(1), 9–14.
Srivilai, J., Nontakhot, K., Nutuan, T., Waranuch, N., Khorana, N., Wisuthiprot, W., Scholfield, C. N., Champachaisri, K., & Ingkaninan, K. (2018). Sesquiterpene-Enriched Extract of Curcuma aeruginosa Roxb. Retards Axillary Hair Growth: A Randomised, Placebo-Controlled, Double-Blind Study. Skin Pharmacology and Physiology, 31(2), 99–106.
Srivilai, J., Phimnuan, P., Jaisabai, J., Luangtoomma, N., Waranuch, N., Khorana, N., Wisuitiprot, W., Scholfield, C. N., Champachaisri, K., & Ingkaninan, K. (2017). Curcuma aeruginosa Roxb. Essential Oil Slows Hair-Growth and Lightens Skin in Axillae; A Randomised, Double Blinded Trial. Phytomedicine, 25, 29–38.
Srivilai, J., Waranuch, N., Tangsumranjit, A., Khorana, N., & Ingkaninan, K. (2018). Germacrone and Sesquiterpene-Enriched Extracts from Curcuma aeruginosa Roxb. Increase Skin Penetration of Minoxidil, A Hair Growth Promoter. Drug Delivery and Translational Research, 8(1), 140–149.
Sugita, P., Firdaus, S., Ilmiawati, A., & Rahayu, D. U. C. R. (2018). Curcumenol: A Guaiane-Type Sesquiterpene from Indonesian Curcuma Heyneana Rhizome and it’s Antibacterial Activity Towards Staphylococcus aureus and Escherichia Coli. Journal of Chemical and Pharmaceutical Research, 10(6), 68–75.
Sugita, P., Octaviana, N., Wukirsari, T., & Rahayu, D. U. . (2018). Chemical Constituent and Antioxidant Activity of Methanol Extract from Indonesian Curcuma aeruginosa Roxb. Rhizome. Journal of Pharmacy Research, 10(1), 293–297.
Suharsanti, R., N, S., E, L., & Rahardhian MRR. (2019). Potency of Belimbing Wuluh (Averrhoa bilimbi) as Antioxidant and Tyrosinase Inhibitor For Skin Whitening Products. Journal Of Pharma Research, 8(4), 151–154.
Suphrom, N., Pumthong, G., Khorana, N., Waranuch, N., Limpeanchob, N., & Ingkaninan, K. (2012). Anti-Androgenic Effect of Sesquiterpenes Isolated from The Rhizomes of Curcuma aeruginosa Roxb. Fitoterapia, 83(5), 864–871.
Zhang, L. S., Shen, S. N., Gao, Y. L., Shi, S. Y., Zhou, C. X., Mo, J. X., Xu, Y. K., Lin, L. G., & Gan, L. S. (2019). Tautomerism and Bioactivities of Curcumenol, A Common Sesquiterpenoid Widely Existing In Edible Plants. Food & Function, 10(3), 1288–1294.
Published
2023-12-15
How to Cite
Suharsanti, R., Wahyuono, S., Astuti, P., & Yuniarti, N. (2023). Isolation and Characterization of Curcumenotone, a Sesquiterpene from Curcuma aeruginosa Roxb as Antioxidant. Indonesian Journal of Pharmacy, 34(4), 593-602. https://doi.org/10.22146/ijp.7799
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Research Article
