PROFIL METABOLIT BERBAGAI EKSTRAK DAUN Chrysophyllum cainito L. MENGGUNAKAN UPLC-QTOF-MS/MS
Abstract
ABSTRACT
Chrysophyllum cainito L. is a plant which empirically used as traditional medicine. The pharmacological effect of C. cainito is caused by secondary metabolite activity contain in the leaves. The aim of this research was to know the metabolites profile in n-hexane extract, ethyl acetate extract, and methanol extract of C. cainito leaves using UPLC-QToF-MS/MS. Dried powder of C. cainito leaves was extracted with n-hexane, ethyl acetate, and methanol with gradual extraction using Ultrasonic Assisted Extraction (UAE). Each extract was prepared with methanol and DCM solvent then injected 5 µl into UPLC-QToF-MS/MS and analyzed with Masslynx 4.1 softwares and Chemspider. The result showed that there were 28 compounds from n-hexane extract with diethyltoluamide as major compound, 47 compounds from ethyl acetate extract with loliolide as major compound, and 34 compounds from methanol extract with eplerenone as major compound. Based on literature study, there were also several compounds that likely having activity as phytoestrogens.
Keyword: Metabolite profiling, chrysophyllum cainito L., UPLC QToF-MS/MS
ABSTRAK
Chrysophyllum cainito L. merupakan tumbuhan yang secara empiris digunakan sebagai obat tradisional. Efek farmakologi tersebut disebabkan adanya aktivitas dari berbagai senyawa metabolit sekunder yang terkandung dalam daun C. cainito. Tujuan dari penelitian ini untuk mengetahui profil metabolit ekstrak n-heksana, ekstrak etil asetat, dan ekstrak metanol daun C. cainito menggunakan UPLC-QToF-MS/MS. Serbuk kering daun C. cainito diekstraksi secara bertingkat menggunakan n-heksana, etil asetat, dan metanol dengan metode UAE. Masing-masing ekstrak dipreparasi dengan metanol dan DCM lalu diinjeksikan sebanyak 5 µl ke dalam UPLC-QToF-MS/MS, kemudian dianalisis dengan software Masslynx 4.1 dan Chemspider. Hasil menunjukkan profil metabolit dari masing-masing ekstrak daun C. cainito, yaitu ekstrak n-heksana dengan 28 senyawa dan diethyltoluamide sebagai senyawa mayor, 47 senyawa terkandung dalam ekstrak etil asetat dengan senyawa mayor loliolide, dan 34 senyawa terkandung dalam ekstrak metanol dengan senyawa mayor yaitu eplerenone. Dari studi literatur diketahui terdapat beberapa senyawa yang memiliki aktivitas sebagai fitoestrogen.
Kata Kunci: Metabolite profiling, Chrysophyllum cainito L., UPLC QToF-MS/MS
References
DAFTAR PUSTAKA
Attardi, B. J., Page, S. T., Hild, S. A, Coss, C. C., Matsumoto, A. M. (2010). Mechanism of Action of Bolandiol (19-nortestosterone-3beta,17beta-diol), a Unique Anabolic Steroid with Androgenic, Estrogenic, and Progestational Activities. The Journal of Steroid Biochemistry and Molecular Biology, 118 (3):151–61
Attwood, D., and Florence, A.T. (1983). Surfactant Systems: Their Chemistry, Pharmacy and Biology. London: Chapman and Hall Ltd.
Barrosa, K. H., Mecchi, M. C., Rando, D. G., Ferreira, A. J., Sartorelli, P., Valle, M. M., Bordin, S., Caperuto, L. C., Lago, J. H., Lellis-Santos, C. (2016). Polygodial, a sesquiterpene isolated from Drimys brasiliensis (Winteraceae), triggers glucocorticoid-like effects on pancreatic β-cells. Chemico-Biological Interactions, 258:245-256
Cui, J., Shen,Y., Li, R. (2013). A Review: Estrogen Synthesis and Signaling Pathways during Aging: from Periphery to Brain. Trends in Molecular Medicine, 19(3):197-209.
Delvaux, M., Maisin, J.M., Arany, Y., Atlan, P., Prieto-Cabanis, M. J., Canal, M., Frexinos, J. (1995). The Effects of Lintopride, a 5HT‐4 Antagonist, on Oesophageal Motility. Alimentary Pharmacology and Therapeutics, 9(5):563-569
Delyani, J. A., Rocha, R., Cook, C. S., Tolbert D. S., Levin S., Roniker B., Workman D. L., Sing Y. L., Whelihan B. (2006). Eplerenone: a Selective Aldosterone Receptor Antagonist (SARA). Cardiovascular Drug Reviews, 19(3):185–200
Dickson, M. A., Carvajal, R. D., Merrill, A. H. Jr, Gonen, M, Cane, L. M., Schwartz, G. K. (2011). A phase I Clinical Trial of Safingol in Combination with Cisplatin in Advanced Solid Tumors. Clinical Cancer Research, 17(8):2484-2492
Ditzen, M., Pellegrino, M., Vosshall, L. B. (2008). Insect Odorant Receptors are Molecular Targets of the Insect Repellent DEET. Sciencexpress, 319(5871):1838–42
Funk, J. L., Frye, J. B., Oyarzo, J. N., Timmermann, B. N. (2009). Comparative Effects of Two Gingerol-Containing Zingiber officinale Extracts on Experimental Rheumatoid Arthritis. Journal of Natural Products, 72 (3):403–7
Grabarczyk, M., Katarzyna, W., Maczka, W., Potaniec, B., Aniol, M. (2015). Loliolide - the Most Ubiquitous Lactone. Folia Biologica et Oecologica, 11:1-8
Griffiths, J. A. (1959). On the Distribution of Gentistic Acid in Green plants. Journal of Experimental Botany, 10:437-442
Handayani, H., Sriherfyna, F. H., Yunianta. (2016). Ekstraksi Antioksidan Daun Sirsak Metode Ultrasonic Bath (Kajian Rasio Bahan: Pelarut dan Lama Ekstraksi). Jurnal Pangan dan Agroindustri, 4(1):262-272
Harborne, J. B. (1994). The Flavonoids Advances in Research Since 1986. Florida: CRC Press LLC.
Harris, A. C., Henttu, P., Parker, G. M., and Sumpter, J. P. (1997). The Estrogenic Activity of Phtalate Esters In Vitro. Environmental Health Perspectives, 105(8):802-811
Hidayat, A. dan Ningsih, I. Y. (2015). Pengembangan Ekstrak Daun dan Buah Kenitu (Chrysophyllum cainito L.) untuk Obat Herbal Terstandar Diabetes Mellitus. Jember: Universitas Negeri Jember.
Hird, S. J., Benjamin, P., Lau, Y., Schuhmacher, R., Krska, R. (2014). Liquid chromatography-mass spectrometry for the determination of chemical contaminants in food. Trends in Analytical Chemistry, 59:59-72
Hong, H., Branham, W. S., Ng, H. W., Moland, C. L., Dial, S. L., Fang, H., Perkins, R., Sheehan, D., Tong, W. (2015). Human Sex Hormone-Binding Globulin Binding Affinities of 125 Structurally Diverse Chemicals and Comparison with Their Binding to Androgen Receptor, Estrogen Receptor, and α-Fetoprotein. Toxicological Sciences, 143(2):333-348
Kandasamy, N., and Ashokkumar, N. (2014). Renoprotective Effect of Myricetin Restrains Dyslipidemia and Renal Mesangial Cell Proliferation by the Suppression 0f Sterol Regulatory Element Binding Proteins In An Experimental Model of Diabetic Nephropathy. European Journal of Pharmacology, 743:53-62
Khatiwora, E., Adsul, V. B., Kulkarni, M., Deshpande, N. R., Kashalkar, R. V. (2012). Antibacterial Activity of Dibutyl Phthalate: a Secondary Metabolite Isolated from Ipomoea carnea stem. Journal of Pharmacy Research, 5(1):150-152
Koffi, N., Amoikon, K. E., Tiebre, M. S., Kadja, B., and Zirihi, G. N. (2009). Effect of Aqueous Extract of Chrysophyllum cainito Leaves on The Glycaemia of Diabetic Rabbits. African Journal Pharmacy and Pharmacology, 3:501-506
Koffi, N’guessan. (2008). Plantes medicinales et pratiques medicales traditionelles chez les peoples Abbey et Krobou du Department d’Agboville (Cote-d’Ivoire). [Thesis]. Cote-d’Ivoire: Universite de Cocody-Abidjan
Krastanov, A. (2010). Metabolomics – The State of Art. Biotechnology & Biotechnological Equipment, 24:1537-1543.
Lee, Dong-Sun. (2000). Dibutyl Phthalate an α-Glucosidase Inhibitor from Streptomyces melanosporofaciens. Journal of Bioscience and Bioengineering, 89(3):271-273
Li, S., Zhu, R., Zhong, M., Zhang, Y., Huang, K., Zhi, Xu., Fu, S. (2010). Effects of Ultrasound-Assistant Extraction Parameter on Total Flavones Yield of Selaginella deoderleinii and its Antioxidant Activity. Journal of Medicinal Plants Research, 4(17):1743-1750
Lim, T. K. (2016). Edible Medicinal and Non-Medicinal Plants: Volume 10, Modified Stems, Roots, Bulbs. Berlin: Springer International Publishing AG.
Lopez, J. A. (1983). Isolation of β-amyrin acetate from leaves and stems of star Apple (Chrysophyllum cainito: Sapotaceae). Ing. Cienc.Quim, 7:22-23
Luo, X. D., Basile, M. J., and Kennely, E. J. (2002) Polyphenolic Antioxidants from Chrysophyllum cainito L. (Star Apple). Journal of Agricultural and Food Chemistry, 50:1379-1382
Madala, N. E., Piater, L., Dubery, I., Steenkamp, P. (2016). Distribution patterns of flavonoids from three Momordica species byultra-high performance liquid chromatography quadrupole time of flight mass spectrometry: a metabolomic profiling approach. Revista Brasileira de Farmacognosia, 26:507-513
McDonald, T., Drescher, K. M., Weber, A., Tracy, S. (2012). Creatinine inhibits bacterial replication. The Journal of Antibiotics, 65(3):153–156
Morton, J. (1987). Star Apple Fruits of Warm Climates. Miami Florida. 408-410
Muhaimin, Syamsurizal, Chaerunisaa A.Y., Sinaga M.S. 2016. Eusiderin I from Eusideroxylon zwagery as Antifungal agent against Plant Pathogenic Fungus. International Journal of ChemTech Research, 9(5):418-424
Naushad, Mu. and Khan, M. R. (2014). Ultra Performance Liquid Chromatography Mass Spectrometry: Evaluation and Applications in Food Analysis. New York: CRC Press.
Pomara C., Barone, R., Gammazza, A. M., Sangiorgi, C., Barone, F., Pitruzzella, A., Locorotondo, N., Gaudio, F. D., Salerno, M., Maglietta, F., Sarni, A. L., Felice, V. D., Cappello, F., Tullazzi, E. (2015). Effects of Nandrolone Stimulation on Testosterone Biosynthesis in Leydig Cells. Journal of Cellular Physiology, 231:1385-1391
Rahman, Atta-ur. (2003). Studies in Natural Products Chemistry: Bioactive Natural Products (Part I). Amsterdam: Elsevier Science B.V.
Sasidharan, S., Chen, Y., Saravanan, D., Sundram K. M., Latha L. Y. (2011). Extraction, isolation and characterization of bioactive compounds from plants’ extracts. Journal of Traditional Complementary and Alternative Medicine, 8(1):1-10
Schröckeneder, Albert. (2012). Towards the Total Synthesis of Portentol A Formal Synthesis of Dimethylglutamine The Crystal Structure of the Dess-Martin Periodinane [Disertasi]. München: Ludwig Maximilians Universität München
Shailajan, S., and Gurjar, D. (2014). Pharmacognostic and Phytochemical Evaluation of Chrysophyllum cainito Linn. Leaves. International Journal of Pharmaceutical Sciences Review and Research, 26:106-111
Sreekumar A., Poisson, L. M., Rajendiran, T. M., Khan, A. P., Cao, Q., Yu, J., Laxman, B., Mehra, R., Lonigro, R. J., Li, Y., Nyati, M. K., Ahsan, A., Kalyana-Sundaram, S., Han, B., Cao, X., Byun, J., Omenn, G. S., Ghosh, D., Pennathur, S., Alexander, D. C., Berger, A., Shuster, J. R., Wei, J. T., Varambally, S., Beecher, C., Chinnaiyan, A. M. (2009). Metabolomic Profiles Delineate Potential Role for Sarcosine In Prostate Cancer Progression. Nature, 457:910-914
Thevissen, K., Hillaert, U., Meert, E. M. K., Chow, K. K., Cammue, B. P. A., Calenbergh, S. V., Francois, I. E. J. A. (2008). Fungicidal activity of truncated analogues of dihydrosphingosine. Bioorganic & Medicinal Chemistry Letters, 18(13):3728-3730
Trivedi, R. K., and Atel, M. C. P. (2012). Development of a Stability-Indicating RP-UPLC Method for Rapid Determination of Metaxalone and its Degradation Products in Solid Oral Dosage Form. Scientia Pharmaceutica, 80:353-366
Verma, G., Dua K. V., Agarwal D. D., Atul, P. K. (2011). Anti-malarial activity of Holarrhena antidysenterica and Viola canescens, plants traditionally used against malaria in the Garhwal region of north-west Himalaya. Malaria Journal, 10:10-20
Wainscott, D. B., Little, S. P., Yin, T., Tu, Y., Rocco, V. P., He, J. X., Nelson D. L. (2007). Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1. The Journal of Pharmacology and Experimental Therapeutics, 320(1):475–485
Yang, X., Kang, M. C., Lee, K. W., Kang, S. M., Lee, W. W., Jeon, Y. J. (2011). Antioxidant Activity and Cell Protective Effect of loliolide Isolated from Sargassum ringgoldianum subsp, coreanum. Algae, 26(2):201-208
Yildiz, F. (2006). Phytoestrogens In Functional Foods. New York: Taylor & Francis Group.
Zhai, B., Clark, J., Ling, T., Connelly, M., Medina-Bolivar, F., Rivas, F. (2014). Antimalarial evaluation of the chemical constituents of hairy root culture of Bixa orellana L. Molecules, 19(1):756-766
Zhang, Z., Bo, T., Bai, Y., Ye, M., An, R., Cheng, F., Liu, H. (2015). Quadrupole time-of-flight Mass Spectrometry as a Powerful Tool for Demystifying Traditional Chinese medicine. TrAC Trends in Analytical Chemistry, 72:169-180
Zhang, F., Zhang J. G., Qu, J., Zhang Q., Prasad, C., Wei, Z. J. (2017). Assessment of Anti-Cancerous Potential of 6-gingerol (Tongling White Ginger) and Its Synergy With Drugs On Human Cervical Adenocarcinoma Cells. Food and Chemical Toxicology, 109(2):910-922
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