Central JSM Biochemistry & Molecular Biology Bringing Excellence in Open Access Review Article *Corresponding author Egydio-Brandão, Anary Priscila Monteiro, Department of Botany, University of São Paulo, Rua do Matão, Alkaloids from Annona: Review 277. Cidade Universitária, São Paulo -SP, Brazil, Tel: 55-11-30917532; Fax: 55-11-30917547; Email from 2005 to 2016 Submitted: 05 August 2017 Egydio-Brandão, Anary Priscila Monteiro1*, Novaes, Paula1 and Accepted: 06 October 2017 Santos, Déborah Yara Alves Cursino dos1 Published: 08 October 2017 1Department of Botany, University of São Paulo, Brazil ISSN: 2333-7109 Copyright Abstract © 2017 Egydio-Brandão et al. Species of Annonaceae have different popular uses as edible fruits or as traditional OPEN ACCESS medicines. The genus Annona is a rich source of secondary metabolites, which have been isolated Keywords and identified from different parts of plant. Among these compounds, alkaloids are known as an • Anthracene alkaloids important class of chemical constituents. Several chemical and pharmacological investigations on • Aporphine alkaloids species of Annona indicated the presence of important bioactive compounds, exhibiting various • Benzylisoquinoline alkaloids biological activities including anti-acetylcholinesterase, antioxidant, antidepressant, antiepileptic, • β-carboline alkaloids antimicrobial, antiplasmodial, antiproliferative, antibacterial, antifungal, anti-ulcer, anxiolytic- • Biological activity like effects, cytotoxic, immune-stimulant and larvicidal. In this review, we analyzed published papers from 2005 to 2016 looking preferably for alkaloid composition of species of Annona related to biological activities. Among these papers, 70 alkaloids were reported during the researched period, distributed in 20 species. Aporphine alkaloids were the most common, corresponding to more than half of all alkaloids described. Most of the available data are for leaves; seeds and roots need further studies. INTRODUCTION A. muricata L. - guanabana or soursop; A. reticulata L. - custard Annonaceae is a pantropical family, which comprises apple; A. macroprophyllata Donn. Sm. - ilama; A. glabra L. - pond- 2400 species distributed in 108 genera arranged in four apple; A. purpurea Moc. & Sessé ex Dunal – soncoya) [9]. subfamilies (Annonoideae, Anaxagoreoideae, Ambavioideae Annona species are used in folk medicine for very different and Malmeoideae). Guatteria (210 species) is the largest genera. treatments. Antdiarrheal use is described for many species includ- Annona (around 200 species) also presents a wide number of ing A. crassiflora Mart. [10], A. muricata [11], A. purpurea Moc. & species, including all previous species placed in Rollinia [1]. The Sessé ex Dunal [12], A. reticulata L. [13] and A. salzmannii A. DC. family is recognized as one of the most diverse, even related to [14]. Emetic use has been pointed out for A. cherimola [15], A. mu- richness and abundance of individuals [2]. This family appears ricata [16,11] and A. squamosa L [11]. Anti-parasitic treatment has into Magnoliales, together with Myristicaceae, Magnoliaceae, been observed for A. cherimola [17], A. muricata [16], A. reticulata Degeneriaceae, Himantandraaceae and Eupomatiaceae [3]. [13], A. salzmannii [14], A. squamosa L [11]. A. foetida Mart. [18], A. Species of Annonaceae present different popular uses as purpurea [12] and A. reticulata [13] have been traditionally used to edible fruits (e.g. A. muricata, A. squamosa, A. cherimola and A. treat fever. Rheumatism treatment is described for A. foetida [18], reticulata) or as traditional medicines (e.g. A. crassiflora, A. A. glabra [19], A. muricata [16; 11]. Ulcers have been threated us- montana, A. muricata and A. squamosa). A wide diversity of ing A. foetida [18], A. reticulata [13], A. salzmannii [14], A. squamosa chemical compounds has been isolated from the members of L [11], while anti-cancer action is described for A. muricata [11] and A. senegalensis [20]. A. muricata [21,22], A. squamosa L [11], A. the secondary metabolites isolated from the bark, leaves, fruits vepretorum [23,24] have been used for pain and A. reticulata [13], andthis seedsfamily. of Acetogenins, Annonaceae diterpenes[4,5] which andare relatedflavonoids to the are biological some of A. rugulosa (Schltdl.) H. Rainer [25] for infections. Other uses in- activities described for the family, e.g. antiprotozoal [6] or clude tranquilizer for A. muricata [26], treatment of skin diseases cytotoxic [7]. However, one of the most important characteristic for A. cherimola [27] and A. salzmannii of Annonaceae species is the presence of alkaloids [8], mainly for A. salzmannii. [14] and A. vepretorum [28], molluscicide for A. benzylisoquinoline. crassiflora [10], insecticide for A. cherimola[14], [17], anti-inflammatory and antimalarial for Pers. [29]. Despite Annona is only the third genus in number of species A. senegalensis in Annonaceae, the most economically important species of this family are placed in this genus (e.g. Annona cherimola Mill. in different parts of the plant, including fruits, leaves, branches, – cherimoya; A. squamosa L. - sugar apple; Annona x atemoya stems,There barks, are aroots, large seedsnumber and of twigsalkaloids [30-34]. that has Several been biologicalidentified Mabb.- atemoya, a hybrid between A. cherimola and A. squamosa; activities described for A. cherimola, A. foetida, A. glabra, A. Cite this article: Egydio-Brandão, APM,Novaes, P, Santos, DYAC (2017) Alkaloids from Annona: Review from 2005 To 2016.. JSM Biochem Mol Biol 4(3): 1031. Egydio-Brandão et al. (2017) Email: Central Bringing Excellence in Open Access mucosa and A. muricata reported, presented the same distribution of the aporphine alkaloids except for seeds. Protoberberine-type is the main Alkaloids are a very diverse group of low-weighted secondary are related to alkaloids profiles. alkaloid in roots, also occurring in stems (22.7%), but with less metabolites with a Nitrogen atom. In plants, most of them present prominence in barks (5%). Some alkaloid-types presented a very restrict distribution, and were detected only in one or two plant organs. Annoretine ), the only one phenanthrene skeleton, systems,an amino whichacid as include precursor, isoquinoline, and they areindole, classified pyrrole, based pyridine upon (55 was reported exclusively in leaves. The no-tyrosine derivative andthe basicpiperidine skeletal structures. configuration Benzylisoquinoline of their carbon–nitrogen alkaloids ringare alkaloids were also restricted. Antracene skeleton was reported synthesized from tyrosine and make up approximately 2500 compounds, which are common in some families of Ranunculales (Papaveraceae, Berberidaceae, Menispermaceae, Ranunculaceae) in barksBesides and the seeds, alkaloid and variation,β-carboline an in enormous barks and difference roots. in plant and in Magnoliaceae [35,36]. organs content can be noted. While almost 46% of the alkaloids were reported in leaves, only 3.5% of them were obtained from There are two classical reviews about alkaloid distribution seeds or roots (Figure 3). It is worthy to notice that both, seed in Annonaceae [4,37]. Recently, three reviews on alkaloids from and roots, are important sources of uncommon alkaloids in Annonaceae were published. Barbalho et al. [38], presented the Annona. In addition, liriodenine (49), an oxoaporphine alkaloid, compounds of A. crassiflora, A. muricata, A. reticulata, A. cuneata, was described for young tissues as embryos, radicles, and roots A. coriacea and A. cherimola and their pharmacological effects. at early developmental stages [43] (Table 1). The other two newest reviews were published as book chapters Biological activities chemical structures and pharmacological activities of alkaloids Few papers described some biological activity investigation forby Rabêlo species et of al. Annona [39], and while Lucio the et other al., [40]. for AnnonaceaeThe first one inpresented general. for isolated alkaloids or, at least, for enriched alkaloid extract (Table 2). Several pharmacological activities have been described journal articles. However, the access to book chapters is much more difficult than for these compounds including anti-acetylcholinesterase [44], The main goal of our revision is to present alkaloid antioxidant, antidepressant [31], antiepileptic [45], antimicrobial, distribution in Annona associated with their biological activities. antileishmanial [32], anti-Trypanosoma [33], antiplasmodial For that, we searched for published papers in the period of [46], antiproliferative [47], antibacterial, antifungal [43], anti- 2005 – 2016 using a combination of the keywords “Annona”, ulcer [48], cytotoxic [49], immune-stimulant, larvicidal [50], and anxiolytic-like [51]. ISI ®Web of Science, and ® “alkaloids” and “biological activity” in two scientific databases, Antileishmanial activity with detection tests only, wereSciFinder. not consider. The search was refined to Leishmaniasis is a disease caused by Protozoan species of include only papers with some compound identification. Papers which are transmitted by the bite of an infected Alkaloids from Annona Leishmania, Seventy alkaloids were reported in 42 papers during the of the leishmaniasis: visceral (also known as Kala-azar, the most searched period (2005 to 2016) from 20 species of Annona seriousfemale ofform Phlebotomines of the disease), and flies. cutaneous There are(the three most main common) forms with some biological activity associated. Most of them (66) are and mucocutaneous.