Isolation and seasonal variation of fruticin in fruits of false indigo-bush (Amorpha fruticosa L. Fabaceae) from Serbia

Stevan Samardžić, Aleksandra Tucović, Danilo Stojanović, Zoran Maksimović

DOI: http://dx.doi.org/10.5937/leksir2040052S

Abstract


Fruticin (amorphin) is a constituent of the fruit of the false indigo-bush (Amorpha fruticosa L.), which belongs to the class of rotenoid glycosides, and shows several interesting pharmacological activities. The aim of this study was to isolate and chemically characterize this natural product, as well as to determine the optimal period of the year for A. fruticosa fruits collection. Fruticin was obtained by re-crystallization of the precipitate that formed after partial evaporation of the extract, prepared by 3-fold extraction of powdered plant material by chloroform - ethanol (1:1, v/v). The structure of the final product was determined by various techniques of instrumental analysis (NMR, UV and MS), and confirmed by comparing the obtained spectra with corresponding data in available literature. The content of fruticin in A. fruticosa fruit was determined by LC-DAD-MS, using the external standard method based on the constructed calibration curve. Limits of detection (LOD) and quantification (LOQ) were also determined. A substantial increase in fruticin content was observed during the ripening period (>50%). It has also been established that the optimal time for fruit collection is mid-December. Obtained results indicate that the content of fruticin in the A. fruticosa fruit is highly dependable on the time of collection. Since the biosynthesis of secondary plant metabolites is influenced not only by the time of collection, but by numerous other factors as well, additional studies are needed to define, with greater certainty, the conditions that are necessary for design of prospective efficient and sustainable production process.

Keywords


Amorpha fruticosa L., fruticin, isolation, chemical characterization, seasonal variation

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References


Aĭzikov, M.I., Rasulova, S.A., Kurmukov, A.G. (1984). Hypocoagulatory action of amorphin in experimental atherosclerosis. Doklady Akademii nauk UzSSR 10: 49–50. (Article in Russian).

Anonymous. (1968). Last month in the World – December 1967. SSSR. Liječnički vjesnik 90: 59-60. (Article in Croatian).

Anonymous. (1974). New preparations: fruticin, a sedative agent. Farmatsiia 6: 84-85. (Article in Russian).

Anonymous. (1982). Order of the USSR Ministry of Health of 05/28/1982 N 503 „On exclusion from the State Register of obsolete medicines“. http://www.hippocratic.ru/medtext1/medtext_738.htm. Accessed: 14.11.2020. (Article in Russian).

Blagojević, M., Konstantinović, B., Samardžić, N., Kurjakov, A., Orlović, S. (2015). Seed bank of Amorpha fruticosa L. on some ruderal sites in Serbia. Journal of Agricultural Science and Technology B 5(2): 122-128. doi: 10.17265/2161-6264/2015.02.006

Buckingham J. (1993) Dictionary of Natural Products, Vol. 1., page 293. Chapman & Hall/CRC Press, London, New York.

Ciuvăţ, A.L., Vasile, D., Dinu, C., Apostol, E., Apostol, B., Petriţan, A.M. (2016). Valorisation possibilities of invasive indigobush (Amorpha fruticosa L.) in Romania. Revista de Silvicultură şi Cinegetică 21(39): 96-99.

Claisse, J., Crombie, L., Peace, R. (1964). Structure and stereochemistry of the vicianoside amorphin, the first rotenoid glycoside. Journal of the Chemical Society 1964: 6023-6036. doi: 10.1039/JR9640006023

Crombie, L., Kilbee, G.W., Whiting, D.A. (1975). Carbon-13 magnetic resonance spectra of natural rotenoids and their relatives. Journal of Chemical Society, Perkin Transactions 1 15: 1497-1499. doi: 10.1039/P19750001497

Gagić, R., Mihajlović, L., Glavendekić, M. (2008). Acanthoscelides pallidipennis (Coleoptera: Bruchidae), a spermatophagous insect of indigo bush (Amorpha fruticosa L.) and its natural enemies in Serbia. Acta herbologica 17(2): 195-201. (Article in Serbian).

Genkina, G.L., Shakirov, T.T., Shamsutdinov, R.I. (1971). Improved spectrophotometric method for determining amorphine in the fruits of Amorpha fruticosa. Pharmaceutical Chemistry Journal 5: 298–300.

Hulina, N. (2010). “Planta Hortifuga” in flora of the continental part of Croatia. Agriculturae Conspectus Scientificus 75(2): 57-65.

Khodzhaev, K.N., Trofimova, N.I., Shamsutdinov, M.R.I., Shakirov, T.T. (1982). Isolation of frutitsin from the seeds of Amorpha fruticosa. Chemistry of Natural Compounds 18: 585–587. doi: 10.1007/BF00575043

Kloutek, E., Popov, A., Drenska, D., Uzunov, P. (1985). Experimental studies on the hepatoprotective activity of isolated Amorpha fruticosa flavonoids Eksperimentalna meditsina i morfologiia 24(2): 50-54. (Article in Bulgarian).

Kozuharova, E., Matkowski, A., Woźniak, D., Simeonova, R., Naychov, Z., Malainer, C., Mocan, A., Nabavi, S.M., Atanasov, A.G. (2017). Amorpha fruticosa - A noxious invasive alien plant in Europe or a medicinal plant against metabolic disease? Frontiers in Pharmacology 8: 333. doi: 10.3389/fphar.2017.00333

Krpan, A.P.B., Tomašić, Ž., Bašić Palković, P. (2011). Biopotential of indigobush (Amorpha fruticosa L.) – second year of investigation. Šumarski list 135(13): 103-112. (Article in Croatian).

Kurmukov, A.G., Aĭzikov, M.I., Rasulova. S.A., Makhmudov, O.Kh. (1986). Hypolipidemic, hypocholesterolemic and antisclerotic action of the rotenoid glycoside amorphin. Farmakologiia i Toksikologiia 49(6): 54-57. (Article in Russian).

Lazarević, P., Stojanović, V., Jelić, I., Perić, R., Krsteski, B., Ajtić, R., Sekulić, N., Branković, S., Sekulić G., Bjedov V. (2012). A preliminary list of invasive species in Serbia, with general measures of control and reduction as a basis of future legal acts. Zaštita prirode 62(1): 5-31. (Article in Serbian). doi: 10.5937/ZasPri1802041S

Li, L., Wang, H.K., Chang, J.J., McPhail, A.T., McPhail, D.R., Terada, H., Konoshima, T., Kokumai, M., Kozuka, M., Estes, J.R., Lee K.H. (1993). Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa. Journal of Natural Products 56(5): 690-8. doi: 10.1021/np50095a005.

Liang Y, Li X, Gu Z, Qin P, Ji M. Toxicity of amorphigenin from the seeds of Amorpha fruticosa against the larvae of Culex pipiens pallens (Diptera: Culicidae). Molecules. 2015;20(2): 3238-54.

López Díaz, A. (2016). Monografia de Amorpha fruticosa L.; una planta muy polifacética. Final Degree Project. Universidad Complutense de Madrid. Available at: https://eprints.ucm.es/49183/ (Accessed: 30 November 2020).

Malenović, A., Stojanović B. (2010). Handbook of pharmaceutical analysis. University of Belgrade - Faculty of Pharmacy, Belgrade.

Moiseev, S.G., Ustinova, E.Z. (1967). Experience in the use of the new Soviet preparation Amorphin (Fruticin) for the prevention of attacks of paroxysmal tachycardia. Sovetskaja Medicina 30(12): 53-56. (Article in Russian).

Muharini, R. (2016). Bioactive Secondary Metabolites from Medicinal Plants. Doctoral Dissertation. Heinrich Heine Universität Düsseldorf. Available at: https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=40400/ (Accessed: 30 November 2020).

Petkov, E., Uzunov, P., Kostova, I., Somleva, T., Ognyanov, I. (1983). Inhibition of rat heart phosphodiesterase by some rotenoids and isoflavonoids. Planta Medica 47(4): 237-9. doi: 10.1055/s-2007-969996.

Radulović, S., Skočajić, D., Bjedov, I., Đunisijević-Bojović, D. (2008). Amorpha fruticosa L. on wet sites in Belgrade. Glasnik Šumarskog fakulteta, Beograd 97: 221-234. (Article in Serbian).

Sariaslani, F.S., Rosazza, J.P. (1983). Microbial transformations of natural antitumor agents: products of rotenone and dihydrorotenone transformation by Cunninghamella blakesleeana. Applied and Environmental Microbiology 45(2): 616-21. doi: 10.1128/AEM.45.2.616-621.1983.

Syropyatov, O.G., Dzeruzhinskaya, N.A. (2001). Phytotherapy of psychosomatic disorders. VEAP-ICKPiP. Kiev. (Book in Russian).

Szigetvári, C. (2002). Initial steps in the regeneration of a floodplain meadow after a decade of dominance of an invasive transformer shrub, Amorpha fruticosa L. Tiscia 33: 67-77.

Wu, X., Liao, H.B., Li, G.Q., Liu, Y., Cui, L., Wu, K.F., Zhu, X.H., Zeng, X.B. (2015). Cytotoxic rotenoid glycosides from the seeds of Amorpha fruticosa. Fitoterapia 100: 75-80. doi: 10.1016/j.fitote.2014.11.015.


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