Simaroubaceae Family: Botany, Chemical Composition and Biological Activities
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Rev Bras Farmacogn 24(2014): 481-501 Review Simaroubaceae family: botany, chemical composition and biological activities Iasmine A.B.S. Alvesa, Henrique M. Mirandab, Luiz A.L. Soaresa,b, Karina P. Randaua,b,* aLaboratório de Farmacognosia, Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal de Pernambuco, Recife, PE, Brazil bLaboratório de Farmacognosia, Departamento de Farmácia, Universidade Federal de Pernambuco, Recife, PE, Brazil ARTICLE INFO ABSTRACT Article history: The Simaroubaceae family includes 32 genera and more than 170 species of trees and Received 20 May 2014 brushes of pantropical distribution. The main distribution hot spots are located at tropical Accepted 10 July 2014 areas of America, extending to Africa, Madagascar and regions of Australia bathed by the Pacific. This family is characterized by the presence of quassinoids, secondary metabolites Keywords: responsible of a wide spectrum of biological activities such as antitumor, antimalarial, an- Chemical constituents tiviral, insecticide, feeding deterrent, amebicide, antiparasitic and herbicidal. Although the Simaba chemical and pharmacological potential of Simaroubaceae family as well as its participa- Simarouba tion in official compendia; such as British, German, French and Brazilian pharmacopoeias, Simaroubaceae and patent registration, many of its species have not been studied yet. In order to direct Quassia further investigation to approach detailed botanical, chemical and pharmacological aspects of the Simaroubaceae, the present work reviews the information regarding the main genera of the family up to 2013. © 2014 Sociedade Brasileira de Farmacognosia. Published by Elsevier Editora Ltda. All rights reserved. troughout the country (Arriaga et al., 2002; Almeida et al., 2007) Introduction (Fig. 1). Due to the chemical diversity previously described for many species of Simaroubaceae family, it is worth noting that it The Simaroubaceae family includes 32 genera and more than can be characterized as a promising source of bioactive molecules 170 species of trees and brushes of pantropical distribution. with remarkable research potential. An example of this is that It is characterized by its content of bitter substances, mostly since 1961, when the first quassinoide structure was elucidated, responsible for its pharmaceutical properties (Fernando and the growing interest on various species of Simaroubaceae family Quinn, 1992; Muhammad et al., 2004). The principal geographical resulted in the isolation and identification of the more than 200 distribution center is located at tropical America, extending to currently-known quassinoids (Curcino Vieira and Braz-Filho, the west to Africa, Madagascar, Asia (Malaysia) and regions of 2006). Nevertheless, many of its species have not been studied Australia bathed by the Pacific (Simão et al., 1991; Saraiva et al., or remain unexplored. In this context, in order to base and 2002;). In Brazil, this family is represented by the genera Quassia direct future studies, the present work is a review of literature and Picrolemma, in the Amazon, Castela and Picrasma, to the from 1846 until 2013, and contemplates botanical, chemical and South; and Simaba, Simarouba and Picrolema, which are present pharmacological aspects of the family’s main species. * Corresponding author. E-mail: [email protected] (K.P. Randau). 0102-695X/$ - see front matter © 2014 Sociedade Brasileira de Farmacognosia. Published by Elsevier Editora Ltda. All rights reserved. http://dx.doi.org/10.1016/j.bjp.2014.07.021 482 Iasmine A.B.S. Alves et al. / Rev Bras Farmacogn 24(2014): 481-501 Figure 1 – Simarouba amara Aubl. (Simaroubaceae). Source: Tarcisio Leão, 2013. of filament and number of stamen and petals. In this Materials and methods context, the family was divided in four tribes: Simaroubeae, Harrisonieae, Ailantheae and Spathelieae. Later on, Information regarding the botanical descriptions, the isolated Bentham and Hooker (1862) proposed a classification based and identified chemical constituents, and the pharmacological on division of the ovary that yielded the tribes Simaroubeae activities of isolated compounds or crude extracts of the main and Picramnieae. Years later, Engler (1874) recognized three species of Simaroubaceae family, were retrieved from books and tribes: Surianeae, Eusimaroubeae and Picramnieae, taking original articles found in several databases (Medline, SciFinder, into account the nature of the carpels and styles, as well Periodicos Capes, Science Direct, Scopus and Web of Science) as the number of ovules. The last classification of Engler in the period from 1846 to 2013, was performed. The used (1931), the most used, was based on the number and nature keywords included Simaroubaceae, Simarouba, Simaba, Quassia of the carpels and styles, number and position of ovules, and other genera belonging to the family. Once the references presence or absence of scales at the filaments’ base and were obtained, those considered relevant were selected. composition of the leaf. This classificiation included nine tribes in six subfamilies. Due to the heterogeneous nature of Simaroubaceae Botany family from the Engler classification (1931), shown in wood anatomy (Webber, 1936; Heimsch, 1942) and Extensive bibliography regarding the botanical aspects of the pericarp (Fernando and Quinn, 1992), pollen morphology Simarubaceae family composition was found. The subfamilies’ (Erdtman, 1952, 1986; Moncada and Machado, 1987) and affinities have been thoroughly discussed, and five of its phytochemistry (Hilditch and Williams, 1964; Simão et six subfamilies; Surianoideae, Kirkioideae, Irvingioideae, al., 1991); later authors reduced the family even more. Picrammioideae and Alvaradoideae, have been removed from the Takhtajan (1987), Cronquist (1988) and Thorne (1992) family. Thus, in this context, only the Simarouboideae subfamily, excluded one or more subfamilies. The studies of Fernando comprised of 22 genera, would be part of the Simaroubaceae and collaborators (1995) on rbcL sequence variation family (Simão et al., 1991; Muhammad et al., 2004). clearly showed that Simaroubaceae is polyphyletic, The Simarubaceae family is botanically related to the which based the recognition of the families Surianaceae Rutaceae, Meliaceae and Burseraceae families, though, in this sensu Cronquist, Kirkiaceae and Irvingiaceae, previously group, it is more related to the first one in terms of chemical segregated to Simaroubaceae. composition, wood anatomy, lack of resin ducts in the bark and The genera Picramnia and Alvaradoa, despite occasionally in the free stamens. It differs from the others by its absence reported as constituents of the Simaroubaceae family of secretory cavities containing aromatic oils in leaves and (Balderrama et al., 2001; Rodríguez-Gamboa et al., 2001; floral parts (Fernando and Quinn, 1992) and by the presence Cortadi et al., 2010), were excluded from it and put into the of quassinoids, exclusive of Simaroubaceae (Thomas, 1990). Picramniaceae family by Fernando and collaborators (1995). Planchon (1846) was the first one to propose an intra- This translocation is supported by the fact that Picramnia and family classification, based on the ovary nature (free Alvaradoa are phytochemically characterized by a vast presence or connate), number of ovules, type of embryo, length of anthraquinones and anthracenic derivates in comparison Iasmine A.B.S. Alves et al. / Rev Bras Farmacogn 24(2014): 481-501 483 to quassinoids, the taxonomic markers of the Simaroubaceae family (Diaz et al., 2004). The species from this family have alternate compound or complete leafs, not punctuate, with or without thorns. Its flowers are, generally, placed together in axial inflorescences, showing free or fused sepals, free petals, stamens in double of the number of the petals, filaments usually with appendix. The ovary is superior, above a short gynophore or above a four or five carpels disk, generally free at the base and fused by the style with one (in the case of Quassia) or two ovules per carpel. Its fruit is a drupe, generally separated in drupelets (Noldin, 2005). The chemical compounds of this nature were, initially, known as “quassin”, after a physician named Quassi used the bark of Simaroubaceae plants to treat fever. The first isolated Chemical constituents and identified quassinoids were quassin (6) and neoquassin (7), from Quassia amara; the isolation was done in by Clark (1937) Since 1930, the Simaroubaceae family has been the subject in the 1930’s. Furthermore, the structural elucidation was of many studies regarding its chemical constitution, and successful until the beginning of the 1960’s, when Valenta and numerous compounds have been isolated and their structure collaborators (1961) were able to apply novel techniques, such has been elucidated; among these, quassinoids, alkaloids, as Nuclear Magnetic Resonance (NMR). Since then, the interest triterpenes, steroids, coumarins, anthraquinones, flavonoids in diverse species of Simaroubaceae family has increased, and other metabolites (Barbosa et al., 2011) (Chart 1). which has resulted in the isolation and identification of the Quassinoids can be considered a taxonomic marker of the more than 200 quassinoids currently known (Curcino Vieira Simaroubaceae family since it is the most abundant group of and Braz-Filho, 2006). natural substances and their synthe almost exclusive (Saraiva et al., 2006; Almeida et al., 2007). Quassinoids Many genera from the Simaroubaceae family have