We studied the alkaloid composition of Annona muricata L. (Annonaceae) leaves collected in February 2009 in Conakry Botanical Garden (Republic of Guinea).
Ordinary CHCl3 extraction afforded total alkaloids (0.125%) that were separated into phenolic and nonphenolic parts. Column chromatography over silica gel of the nonphenolic fraction isolated three bases; of the phenolic fraction, one. Spectral data, physical constants of the alkaloids and their salts, chemical transformation, and comparison with authentic samples identified the pure alkaloids.
Base 1, C17H15NO2, mp 120–122°C, mass spectrum (m/z): 265 [M]+, 264 [M – 1]+ (100), 250, 236, 235; identified as anonaine [1,2].
Base 2, isolated as the hydrochloride, C19H19NO3·HCl, mp 244–246°C, identified as isolaureline [3,4].
Base 3, C18H17NO3, mp 124–126°C (acetone), UV spectrum (λmax, EtOH): 219, 282 (log ε 4.49, 4.25), spectrum similar to that of isolaureline.
The mass spectrum of 3 had peaks for ions (m/z) 295 [M]+, 294 [M – 1]+, 280 [M – 15]+, 266 [M – 29]+, and 147.5 [M]++ that were characteristic of noraporphine alkaloids. A comparison of spectral data of 3 and 2 in addition to the difference in the molecular weights by 14 mass units suggested that 3 was norisolaureline.
In fact, Hess methylation of 3 produced a base that was identical to 2. According to these results, 3 was identified as xylopine [2,5].
Base 4, C17H19NO3, phenolic crystalline base, mp 218–220°C (acetone), identified as coclaurine [6,7].
Thus, we studied the alkaloid composition of Annona muricata leaves and isolated for the first time and identified the aporphine alkaloids anonaine, isolaureline, and xylopine and the benzyltetrahydroisoquinoline alkaloid coclaurine, which was isolated previously from this plant [7].
References
R. Ziyaev, O. N. Arslanova, A. Abdusamatov, and S. Yu. Yunusov, Khim. Prir. Soedin., 429 (1980).
H. Guinaudean, M. Leboeuf, and A. Cave, J. Nat. Prod., 38, 275 (1975); 42, 325 (1979); 46, 761 (1983); 51, 389 (1989).
R. Ziyaev, A. Abdusamatov, and S. Yu. Yunusov, Khim. Prir. Soedin., 685 (1974).
R. Ziyaev, M. D. Sturua, A. Abdusamatov, and D. M. Tsakadze, Khim. Prir. Soedin., 407 (1999).
D. Cortes, A. Ramahatra, A. Cave, J. C. Bayma, and H. Dadoun, J. Nat. Prod., 48, 254 (1985).
R. Ziyaev, T. Irgashev, I. A. Israilov, N. D. Abdullaev, M. S. Yunusov, and S. Yu. Yunusov, Khim. Prir. Soedin., 239 (1977).
M. Leboeuf, C. Legueut, A. Cave, J. F. Desconclois, P. Forgacs, and H. Jacquemin, Planta Med., 42, 37 (1981).
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, p. 287, March–April, 2011.
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Fofana, S., Ziyaev, R., Abdusamatov, A. et al. Alkaloids from Annona muricata leaves. Chem Nat Compd 47, 321 (2011). https://doi.org/10.1007/s10600-011-9921-5
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DOI: https://doi.org/10.1007/s10600-011-9921-5