Secondary metabolites from Morinda elliptica leaves and root extracts and their antioxidant activities
Main Article Content
Abstract
The isolation and purification of dichloromethane fraction of the root bark extract and leaves extract of Morinda elliptica using different chromatographic methods have led to a total of five metabolites. Their structures were elucidated using various spectral data and were confirmed as benzaldehyde (1), 2-hydroxy-1-methoxyanthracene-9,10-quinone (2), dehydroabietic acid (3), and 3-(4-ethoxy-3-methoxyphenyl)-1-phenylprop-2-en-1-one (4), which were extracted from the root, while methyl cinnamate (5) was successfully isolated from the leaves extract. The 1,1-diphenyl-2-picryl-hydrazil assay revealed that dichloromethane and methanol fractions of the leaves and root extracts demonstrated strong antioxidant activities, which were comparable with ascorbic acid. Hexane and ethyl acetate fractions showed weak antioxidant activities. This study showed that M. elliptica has a beneficial effect, considering the virtue of its antioxidant properties. These isolated compounds (1-4) were reported for the first time in the root bark extract of M. elliptica and contributed to the chemotaxonomic importance of M. elliptica. Dehydroabietic acid (3) which is claimed to be a key to active compounds in treating acute stroke, epilepsy, asthma, hypertension, gastric hypermotility, and psychoses, has further added to the medicinal value of M. elliptica.
Downloads
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Anam, F., Abbas, A., Lo, K. M., Hameed, S., Ramasami, P., Umar, Y., Ullah, A., and Naseer, M. M. (2017). Synthesis, crystal structure, experimental and theoretical investigations of 3-(4-ethoxy-3-methoxyphenyl)-1-phenylprop-2-en-1-one. Journal of Molecular Structure, 1127, 742-750.
Aqil, F., Ahmed, I., and Mehmood, Z. (2006). Antioxidant and free radical scavenging properties of twelve traditionally used Indian medicinal plants. Turkish Journal of Biology, 30, 177-183.
Burkill, I. H. (1996). Dictionary of The Economic Products of The Malay Peninsula Crown Agents for The Colonies, Kuala Lumpur: Ministry of Agriculture and Co-Operatives, pp. 253-260.
Chan-Blanco, Y., Vaillant, F., Perez, A. M., Reynes, M., Brillouet, J. M., and Brat, P. (2006). The noni fruit (Morinda citrifolia L.): a review of agricultural research, nutritional and therapeutic properties. Journal of Food Composition and Analysis, 19(6-7), 645-654.
Dahiru, D., Mamman, D. N., and Wakawa, H. Y. (2010). Ziziphus mauritiana fruit extract inhibits carbon tetrachloride-induced hepatotoxicity in male rats. Pakistan Journal of Nutrition, 9(10), 990-993.
Djeridane, A., Yousfi, M., Nadjemi, B., Boutassouna, D., Stocker, P., and Vidal, N. (2006). Antioxidant activity of some algerian medicinal plants extracts containing phenolic compounds. Food Chemistry, 97(4), 654-660.
Efdi, M., Fujita, S., Inuzuka, T., and Koketsu, M. (2010). Chemical studies on Goniothalamus tapis Miq. Natural Product Research, 24(7), 657-662.
Fouillaud, M., Venkatachalam, M., Girard-Valenciennes, E., Caro, Y., and Dufossé, L. (2016). Anthraquinones and derivatives from marine-derived fungi: structural diversity and selected biological activities. Marine Drugs, 14(4), 64-67.
Gonzalez, M. A., Perez-Guaita, D., Correa-Royero, J., Zapata, B., Agudelo, L., Mesa-Arango, A., and Betancur-Galvis, L. (2010). Synthesis and biological evaluation of dehydroabietic acid derivatives. European Journal of Medicinal Chemistry, 45(2), 811-816.
Hoskins, J. A. (1984). The occurrence, metabolism and toxicity of cinnamic acid and related compounds. Journal of Applied Toxicology, 4(6), 283-292.
Ismail, N. H., Ali, A. M., Aimi, N., Kitajima, M., Takayama, H., and Lajis, N. H. (1997). Anthraquinones from Morinda elliptica. Phytochemistry, 45(8), 1723-1725.
Ismail, N. H., Alias, A., and Osman, C. P. (2012). Alkaloids and anthraquinones from Malaysian flora. In Phytochemicals-A Global Perspective of Their Role in Nutrition and Health (Rao, V., ed.), pp. 287-306. Beijing: InTech.
Kadhim, M. J., Sosa, A. A., and Hameed, I. H. (2016). Evaluation of anti-bacterial activity and bioactive chemical analysis of Ocimum basilicum using Fourier transform infrared (FT-IR) and gas chromatography-mass spectrometry (GC-MS) techniques. Journal of Pharmacognosy and Phytotherapy, 8(6), 127-146.
Kalaiselvan, A., Gokulakrishnan, K., and Anand, T. (2012). Gas chromatography-Mass Spectrum analysis of bioactive components of the ethanol extract of Andrographis Paniculata. Journal of Pharmaceutical and Biomedical Science, 20(15), 1-3.
Khong, H. Y., Zakaria, Z., Ismail, N. H., Nor, Z. M., Ahmad, R., and Din, L. B. (2006). Bioactivity investigation of Litsea globularia in Borneo. Malaysian Journal of Science, 28, 223-228.
Komarova, K. G., Sakipov, S. N., Plotnikov, V. G., and Alfimov, M. V. (2015). Luminescent properties of chalcone and its amino derivatives. Journal of Luminescence, 164, 57-63.
Koutsaviti, A., Ioannou, E., Couladis, M., Tzakou, O., and Roussis, V. (2017). 1H and 13C NMR spectral assignments of abietane diterpenes from Pinus heldreichii and Pinus nigra subsp. nigra. Magnetic Resonance in Chemistry, 55(8), 772-778.
Mariya, S., and Reena, L. (2017). Evaluation of pigments as antioxidant and antibacterial agents from beta vulgaris Linn. International Journal of Current Pharmaceutical Research, 9(3), 33-37.
Mahapatra, D. K., Asati, V., and Bharti, S. K. (2015). Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives. European Journal of Medicinal Chemistry, 92, 839-865.
Matos, M. J., Vazquez-Rodriguez, S., Uriarte, E., and Santana, L. (2015). Potential pharmacological uses of chalcones: a patent review (from June 2011 - 2014). Expert Opinion on Therapeutic Patients, 25(3), 351-366.
Molina, G., Pêssoa, M. G., Pimentel, M. R., Pelissari, F. M., Bicas, J. L., and Pastore, G. M. (2014). Production of natural flavor compounds using monoterpenes as substrates. In New Developments in Terpene Research (Hu, J., ed.), pp. 1-24. New York: Nova Publishers.
Nasir, A. B. S., Jasamai, M., and Jantan, I. (2012). Synthesis and biological evaluation of chalcone derivatives (mini review). Mini Reviews in Medicinal Chemistry, 12(13), 1394-1403.
Padalia, H., Moteriya, P., Satasiya, R., and Chanda, S. (2015). In vitro free radical scavenging activity and phenol and flavonoid content of Nerium indicum, Pelto phorampterocarpum and Rosa spps. flower extracts. Asian Journal of Pharmaceutical and Clinical Research, 8(1), 91-97.
Palipoch, S. (2013). A review of oxidative stress in acute kidney injury: protective role of medicinal plants-derived antioxidants. African Journal of Traditional, Complementary and Alternative Medicines, 10(4), 88-93.
Prakash, V., Mishra, P. K., and Mishra, M. (2009). Screening of medicinal plant extracts for antioxidant activity. Journal of Medicinal Plants Research, 3(8), 608-612.
Rath, G., Ndonzao, M., and Hostettmann, K. (1995). Antifungal anthraquinones from Morinda lucida. International Journal of Pharmacognosy, 33(2), 107-114.
Rosenfeld, M. E. (1998). Inflammation, lipids, and free radicals: lessons learned from the atherogenic process. Seminars in Reproductive Endocrinology, 16(4), 249-261.
Rupan, B., Gunja, A., Sujan, G. P. S., and Shruthi, S. D. (2012). A review on medicinal plants having antioxidant potential. Journal of Pharmaceutical Research, 5(8), 4278-4287.
Sahu, S. N., Balbhadra, S. S., Choudhary, J., and Kohli, D. V. (2012). Exploring pharmacological significance of chalcone scaffold: a review. Current Medicinal Chemistry, 19(2), 209-225.
Sawicka, D., Car, H., Borawska, M. H., and Nikliński, J. (2012). The anticancer activity of propolis. Folia Histochemica et Cytobiologica, 50(1), 25-37.
Shalini, S., and Sampathkumar, P. (2012). Phytochemical screening and antimicrobial activity of plant extracts for disease management. International Journal of Current Science, 20, 209-218.
Shaza, S., and Joumaa, M. (2016). Isolation and identification of methyl cinnamate from Syrian Ocimum basilicum. Chemistry and Materials Research, 8(6), 13-19.
Subramaniam, V., Adenan, M. I., Ahmad, A. R., and Sahdan, R. (2003). Natural antioxidants: Piper sarmentosum (kadok) and Morinda elliptica (mengkudu). Malaysian Journal of Nutrition, 9(1), 41-51.
Sun, Y. F., Wang, H. P., Chen, Z. Y., and Duan, W. Z. (2013). Solid-state fluorescence emission and second-order nonlinear optical properties of coumarin-based fluorophores. Journal of Fluorescence, 23(1), 123-130.
Tan, D. W., Xie, J. B., Li, Q., Li, H. X., Li, J. C., Li, H. Y., and Lang, J. P. (2014). Syntheses and structures of copper complexes of 3-(6-(1-H-pyrazol-1-yl) pyridin-2-yl)-pyrazol-1-ide and their excellent performance in the syntheses of nitriles and aldehydes. Dalton Transactions, 43(37), 14061-14071.
Velioglu, Y. S., Mazza, G., Gao, L., and Oomah, B. D. (1998). Antioxidant activity and total phenolics in selected fruits, vegetables, and grain products. Journal of Agriculture and Food Chemistry. 46(10), 4113-4117.
Verma, R. S., Padalia, R. C., Singh, V. R., Goswami, P., Chauhan, A., and Bhukya, B. (2017). Natural benzaldehyde from Prunus persica (L.) Batsch. International Journal of Food Properties, 20(2), 1259-1263.
Wakawa, H. Y, and Hauwa, M. (2013). Protective effect of Erythrina senegalensis (DC) leaves extract on carbon tetrachloride-induced liver injury in rats. Asian Journal of Biological Sciences, 6(4), 234-238.
Wakawa, H. Y., Ahmad, F. B., and Ahmad, Z. (2017). Antibacterial activity of leaves and root extracts of Abrus precatorius. Journal of Medicinal Plants, 5(6), 96-99.
Wang, H., Cao, G. H., and Prior, R. L. (1996). Total antioxidant capacity of fruits. Journal of Agriculture and Food Chemistry. 44(3), 701-705.
Wong, K. M. (1984). A synopsis of Morinda (Rubiaceae) in the Malay Peninsula, with two new species. Malay Nature Journal, 38, 89-98.
Wu, Y. B., Zheng, C. J., Qin, L. P., Sun, L. N., Han, T., Jiao, L., Zang, Q., and Wu, J. Z. (2009). Anti-osteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts. Molecules, 14(1), 573-583.
Xing, Y., Xu, Q., Li, X., Che, Z., and Yun, J. (2012). Antifungal activities of clove oil against Rhizopus nigricans, Aspergillus flavus and Penicillium citrinum in-vitro and in wounded fruit test. Journal of Food Safety, 32(1), 84-93.
Yang, W., Cheng, Z., Xu, Y., Shao, J., Zhou, W., Xie, J., and Li, M. (2015). A highly selective fluorescent chemo-sensor for cyanide anions based on a chalcone derivative in the presence of iron (III) ions, and its capacity for living cell imaging in mixed aqueous systems. New Journal of Chemistry, 39(9), 7488-7494.
Young, I. S., and Woodside, J. V. (2001). Antioxidants in health and disease. Journal of Clinical Pathology. 54(3), 176-186.