Alkaloids from Annona muricata leaves

Abstract

We studied the alkaloid composition of Annona muricata L. (Annonaceae) leaves collected in February 2009 in Conakry Botanical Garden (Republic of Guinea). Ordinary CHCl 3 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, C 17 H 15 NO 2 , 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, C 19 H 19 NO 3 •HCl, mp 244-246°C, identified as isolaureline [3, 4]. Base 3, C 18 H 17 NO 3 , mp 124-126°C (acetone), UV spectrum (O max , EtOH): 219, 282 (log H 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, C 17 H 19 NO 3 , 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].

Exploring the Leaves of Annona muricata L. as a Source of Potential Anti-inflammatory and Anticancer Agents

“…The chloroform extraction of A. muricata leaves yielded a crude extract with 0.125% of total alkaloids, which was later separated into nonphenolic and phenolic parts and subjected to column chromatography over silica gel. The nonphenolic fraction afforded aporphine alkaloids identified as anonaine, isolaureline, and xylopine, while the phenolic fraction led to the isolation of coclaurine, the benzyltetrahydroisoquinoline alkaloid (Fofana et al, 2011 ). Fofana et al ( 2011 ) conducted further investigation on the alkaloid content of A. muricata leaves using chromatography over a column of silica gel.…”

“…The nonphenolic fraction afforded aporphine alkaloids identified as anonaine, isolaureline, and xylopine, while the phenolic fraction led to the isolation of coclaurine, the benzyltetrahydroisoquinoline alkaloid (Fofana et al, 2011 ). Fofana et al ( 2011 ) conducted further investigation on the alkaloid content of A. muricata leaves using chromatography over a column of silica gel. The alkaloids were eluted by various ratios of benzene and ethanol solvent system 99:1, 98:2, 95:5, and 90:10, yielded N -methylcoclaurine, asimilobin, remerine, isoboldine, and liriodenine.…”

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

“…While in leaves, the greatest presence occurred during fruiting (August -October rains), in the stems ( Figure 5A -5 C), the pattern was the opposite, with the highest levels during foliar senescence in the February-April dry season (p < 0.05, Figure 5). (4) [18] [19] 900128-00-6…”

“…12.41 Tetrahydroisoquinoline 236 (M + , 100), 222 (19), 237 (14), 220 (12) NIST [15] 2169 [26] Antifungal Activities of Alkaloidal Extracts of A. purpurea…”

Annonamine, a New Aporphine Alkaloid from the Leaves of Annona muricata

“…6) In this study, we have phytochemically investigated the leaves of the title plant in detail to characterize the chemical constituents especially on alkaloids, because the leaves of A. muricata are used as tea for cardiotonics and it has been known that A. muricata produced benzylisoquinoline type alkaloids. 7,8) The present study describes the isolation and structural elucidation of a new aporphine alkaloid, annonamine (1) together with four known alkaloids (2)(3)(4)(5). The neurotoxicities of these compounds (1)(2)(3)(4)(5) were also investigated against human neuroblastoma cell line, SH-SY5Y.…”