Send Orders for Reprints to [email protected] 290 The Natural Products Journal, 2014, 4, 290-298 Chemical Constituents and Biological Activities of Simira Genus: A Contribution to the Chemotaxonomic of Rubiaceae Family Vinicius F. Moreira*, Ivo J. C. Vieira and Raimundo Braz-Filho Sector of Natural Products Chemistry, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes-28013-602, RJ, Brazil Abstract: The Simira genus belongs to the Rubiaceae family. Studies of this genus have attracted interest, mainly due to phototoxic activities, antifebrile, tonic and purgative presented by some secondary metabolites isolated from drug value of species of this genus. This study is a review of the Simira genus, through the acquisition of data from studies of phytochemicals and evaluation of biological activities of the species that compose it, in order to contribute their chemotaxonomic classification within the family. Keywords: Biological activities, chemical constituents, chemotaxom, phytochemicals, Rubiaceae, Simira. 1. INTRODUCTION genus was reordered into the subfamily Ixoroideae with the tribe Condamineeae by using molecular phylogenetic data Rubiaceae family includes approximately 660 genera and reconstruction [10]. about 11,150 species [1]. In molecular phylogenetic studies, this family is divided into three subfamilies: Cinchonoideae, Facing these changes in the classification of the genus Ixoroideae and Rubioideae [2, 3]. within subfamilies and tribes, it is necessary to gather data from various fields of study in order to confirm the position Occupying the fourth place in diversity among the of this genus within the family. In this review we sought, Angiosperms, behind only the Asteraceae, Orchidaceae primarily, chemical data collection and the main evaluations and Leguminosae [4], the Rubiaceae family has a wide of biological activities. distribution, mainly in tropical and subtropical regions, also reaching temperate and cold regions of Europe and Northern 2. METHODOLOGY Canada [5]. In America, the family is represented by approximately 229 genera and 5,200 species [6]. In Brazil, Data collection was conducted through websites and there are about 118 genera and 1,347 species, corresponding portals of academic research and databases: www.ibict.br, to one of the main families of our flora, even though a large www.scielo.org, www.sciencedirect.com, https://scifinder. number of species are still without any biological or cas.org, www.scirus.com and www.periodicos.capes.gov.br. phytochemicals studies [7]. The terms used in the strategy for scientific publications This vast family has a great range of chemical structures search were outlined by genus, species and family. With the goal of giving greater scope to the bibliographical study, which vary little, but with very significant pharmacological some specific terms related to phytochemical studies and potential. Among the classes of secondary metabolites biological activities were also selected. presented by the family, one can highlight iridoids, anthraquinones, triterpenes and indole alkaloids, the latter The academic papers and scientific publications obtained being considered as a chemotaxonomic marker of the family for the genre are sorted and presented in this study on [8]. Numerous chemical constituents such as flavonoids and four items: phytochemical studies, biological activities, other phenolic derivatives and Terpenoids (Diterpenes), are ethnopharmacological activities and other studies, according also found in this family [9]. to the information presented. From the Rubiaceae family, Simira genus was classified 3. THE Simira GENUS in the subfamily Cinchonoideae and in the tribe Rondeletieae based on morphological data. However, phylogenetic studies The Simira genus includes 45 species distributed in the based on molecular data places Simira in the tribe Simireae Neotropics, from Mexico to Bolivia, Paraguay and Brazil, within the subfamily Ixoroideae [3]. Recently, the Simira with reported species in the flora of Colombia, Venezuela, Costa Rica, Panama, Belize, Ecuador, Peru, Guyana and Argentina. It is represented in Brazil by approximately 19 *Address correspondence to this author at the Sector of Natural Products species distributed among the States of Amazonas, Pará, Chemistry, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Goiás, Espírito Santo, Rio de Janeiro, São Paulo, Paraná and 28013-602 Campos dos Goytacazes-RJ, Brazil; Tel: +55 22 2748 6504; E-mail: [email protected] Santa Catarina, inserted in the Atlantic forest. Eight species 2210-3163/14 $58.00+.00 © 2014 Bentham Science Publishers Chemical Constituents and Biological Activities of Simira The Natural Products Journal, 2014, Vol. 4, No. 4 291 Table 1. Substances isolated from the genus Simira. Substances Species References Alkaloids Harman (1) S. mexicana, S. glaziovii, S. rubra, S. salvadorensis, [19, 22, 23, 25, 30] S. eliezeriana, S. grazielae Ophiorine A (2) S. glaziovii, S. tinctoria, S. williamsii, S. grazielae [21, 24, 30] Ophiorine B (3) S. glaziovii, S. tinctoria, S. williamsii [21, 24] Sickingine (4) S. tinctoria, S. williamsii [24] 5α-Carboxystrictosidine (5) S. tinctoria, S. williamsii [24] Lyalosidic acid (6) S. tinctoria, S. williamsii [24] Maxonine (7) S. maxonii [26-28] Methyl lyalosilate (8) S. glaziovii [21] Pentaacetyllyalosidic acid (9), S. glaziovii [21] 1,22-Lactamlyalosíde (10) S. glaziovii [21] Harmine (11) S. tinctoria, S. williamsii [24] Strictosamide (12) S. mexicana [25] N-acetyl-serotonin (13) S. grazielae [30] Coumarins Isofraxidine (14) S. glaziovii, S. grazielae [22, 30] Scopoletine (15) S. glaziovii, S. tinctoria, S. williamsii, S. grazielae [22, 24, 30] Dimethylfratexine (16) S. glaziovii, S. grazielae [22, 30] 7-Hydroxy-8-methoxycoumarin (17) S. grazielae [30] 5,7-Dimethoxycoumarin (18) S. grazielae [30] Terpenoids Simirane A (19) S. eliezeriana [23] Simirane B (20) S. glaziovii, S. eliezeriana [22, 23] Lupeol (21), S. glaziovii [22] Lupenone (22) S. glaziovii [22] 1β,3β-Dihydroxyolean-12-en (23) S. glaziovii [21] Oleanoic ácid (24) S. tinctoria, S. williamsii [24] Eufol (25), S. glaziovii [29] Butirospermol (26), S. glaziovii [29] Steroids Sitosterol (27) S. glaziovii, S. eliezeriana, S. grazielae [21-23, 29, 30] Stigmasterol (28) S. glaziovii, S. eliezeriana, S. grazielae [22, 23, 30] Campesterol (29) S. glaziovii, S. eliezeriana [22, 23] 3β-O-β-D-Glicopyranosylsitosterol (30) S. glaziovii, S. grazielae [21, 30] β-Sitostenone (31), S. glaziovii [22] Stigmastenone (32) S. glaziovii [22] 3-O-Glicopyranosyl-(6,1)-acil-sitosterol (33) S. glaziovii [22] 292 The Natural Products Journal, 2014, Vol. 4, No. 4 Moreira et al. Table 1. contd…. Substances Species References Iridoids Loganin (34) S. tinctoria, S. williamsii [24] Sweroside (35) S. tinctoria, S. williamsii [24] Secoxyloganin (36) S. tinctoria, S. williamsii [24] Lignans Pinoresinol (37) S. eliezeriana, S. grazielae [23, 30] Pinocebrine (38) S. glaziovii [22] Other substances Methyl hexadecanoate (39) S. glaziovii [21] Hexadecanoic acid (40) S. glaziovii [21] Octadecanoic acid (41) S. glaziovii [21] Eicosanoic acid (42) S. glaziovii [21] Inositol (43) S. glaziovii [29] Methyl trans-4-hydroxy-3-methoxycinnamate (44) S. glaziovii [21] Coniferyl aldehyde (45) S. eliezeriana [23] Syrigaldehyde (46) S. eliezeriana, S. grazielae [23, 30] 3,4,5-Trimethoxyphenol (47) S. grazielae [30] 6’-O-Vaniloilchioside (48) S. grazielae [30] are found in the Southeast region, five of which occur in the photo-dermatitis in humans and predators, conferring an State of Rio de Janeiro [7, 11-14]. evolutionary advantage to the plants that have these The name Simira is popular in Guyana. In Brazil, species substances [19]. of this genus are known as araribá, araribá-vermelha, araribá- Simira species with reports in the literature of chemical rosa, araribá-branca, quina-rosa, canela-samambaia, maiate e studies until now are presented in Table 1, where the isolated marfim [11]. substances are listed, and where the names of the species from which we isolated the substances, and the original The genus is represented by small to large trees with bibliographic references of the citations referring to the species of economic interest, known for their tinctorial, substances are. The structures for these substances are timber, craft and landscape values for the planting of streets. represented in Fig. 1, and the biosynthetic pathway for these It is characterized by presenting brown or greyish heartwood, structures is in Torssell 1997 [20]. yellowish or greyish sapwood when freshly cut, and generally acquiring reddish, purplish or pink color when 3.1. Biological Activities of Simira Genus exposed to air and/or brightness which disappears a few months after collection [15-17]. The bibliographic survey highlighted studies on assessment of biological activities from extracts of the species Simira The interest on the chemical study of Simira species is glaziovii and S. sampaioana against Mycobacterium fortuitum based mainly on activities and substances of phar- and M. malmoense. We conducted a susceptibility screening macological value that were already identified in this genus, to determine the activity of extracts and partitioned plant with many of these species being used by the local extracts at fixed concentrations of 100 µg/mL, where the species community as producers of coloring, antifebrile, tonic and of Simira genus were not effective against mycobacteria purgative substances [17]. under study at