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Chemical Compounds and Biologic Activities: a Review of Cedrela Genus

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Chemical Compounds and Biologic Activities: a Review of Cedrela Genus molecules Review Chemical Compounds and Biologic Activities: A Review of Cedrela Genus Thalya Soares R. Nogueira 1,* , Michel de S. Passos 1, Lara Pessanha S. Nascimento 1 , Mayara Barreto de S. Arantes 1, Noemi O. Monteiro 1, Samyra Imad da S. Boeno 1, Almir de Carvalho Junior 2, Otoniel de A. Azevedo 3, Wagner da S. Terra 4, Milena Gonçalves C. Vieira 4, Raimundo Braz-Filho 1,5 and Ivo J. Curcino Vieira 1 1 Laboratório de Ciências Químicas, Centro de Ciências e Tecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Rio de Janeiro 20000-000, Brazil; [email protected] (M.d.S.P.); [email protected] (L.P.S.N.); [email protected] (M.B.d.S.A.); [email protected] (N.O.M.); [email protected] (S.I.d.S.B.); [email protected] (R.B.-F.); [email protected] (I.J.C.V.) 2 Instituto Federal de Santa Catarina, Campus Criciúma, Criciúma 88800-000, Brazil; [email protected] 3 Centro Universitário São Camilo, Campus I, Rua São Camilo de Léllis 01, Cachoeiro de Itapemirim, Espírito Santo 29304-910, Brazil; [email protected] 4 Instituto Federal de Educação, Ciência e Tecnologia Fluminense, Campus Campos Centro, Campos dos Goytacazes, Rio de Janeiro 28030-130, Brazil; [email protected] (W.d.S.T.); milena.uff@gmail.com (M.G.C.V.) 5 Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro 20000-000, Brazil * Correspondence: [email protected]; Tel.: +22-2748-6207 Received: 13 October 2020; Accepted: 16 November 2020; Published: 18 November 2020 Abstract: The genus Cedrela P. Browne, which belongs to the Meliaceae family, has eighteen species. Trees of this genus are of economic interest due to wood quality, as well as being the focus of studies because of relevant biologic activities as in other Meliaceae species. These activities are mainly related to limonoids, a characteristic class of compounds in this family. Therefore, the aim of this review is to perform a survey of the citations in the literature on the Cedrela genus species. Articles were found on quantitative and qualitative phytochemical studies of the Cedrela species, revealing the chemical compounds identified, such as aliphatics acid and alcohol, flavonoids, tocopherol, monoterpenes, sesquiterpenes, triterpenes, cycloartanes, steroids, and limonoids. Although some activities were tested, the majority of studies focused on the insecticidal, antifeedant, or insect growth inhibitor activities of this genus. Nonetheless, the most promising activities were related to their antimalarial and antitripanocidal effects, although further investigations are still needed. Keywords: Meliaceae; chemical profile; Cedrela genus; limonoids; biological activity 1. Introduction The genus Cedrela P. Browne contains 18 species (Figure1) and is one of 53 genera of trees and shrubs from the Meliaceae family. These species are distributed from northern Mexico to the northwest part of Argentina [1–3]. Molecules 2020, 25, 5401; doi:10.3390/molecules25225401 www.mdpi.com/journal/molecules Molecules 2020, 25, 5401 2 of 34 Molecules 2020, 25, x FOR PEER REVIEW 2 of 34 Figure 1. 1.Accepted Accepted names names of 18 Cedrelaof 18species. Cedrela Data species from The. PlantData Listfrom site (Thehttp: //www.theplantlist.Plant List site org(http://www.theplantlist.org/tpl1.1/search?q=cedrela)/tpl1.1/search?q=cedrela) and Palacios et al. [3]. and Palacios et al. [3]. Meliaceae trees are known as an excellent hardwood, prized for their wood quality, besides Meliaceae trees are known as an excellent hardwood, prized for their wood quality, besides having considerable economic value, for example, cedar (Cedrela) and mahogany (Swietenia spp., having considerable economic value, for example, cedar (Cedrela) and mahogany (Swietenia spp., Khaya spp.) [4,5]. As a result, plants of this genus have experienced overexploitation, leading to three Khaya spp.) [4,5]. As a result, plants of this genus have experienced overexploitation, leading to three species being added to the Official National List of Flora Species Endangered by Decree No. 443 of species being added to the Official National List of Flora Species Endangered by Decree No. 443 of the Brazilian Ministry of the Environment on 17 December 2014 [6]. In this decree, Cedrela fissilis the Brazilian Ministry of the Environment on 17 December 2014 [6]. In this decree, Cedrela fissilis Vell. Vell. and Cedrela odorata L. were considered vulnerable species (VU), and C. angustifolia DC. an and Cedrela odorata L. were considered vulnerable species (VU), and C. angustifolia DC. an endangered endangered species (EN). Furthermore, these species were also added to the International Union for species (EN). Furthermore, these species were also added to the International Union for Conservation Conservationof Nature (IUCN) of Nature Red (IUCN)List of threatened Red List of species. threatened Therefore, species. several Therefore, recent several studies, recent mainly studies, in mainly in biotechnology, have focused on sustainable production and the use of Cedrela in forest biotechnology, have focused on sustainable production and the use of Cedrela in forest cultivation. cultivation.Moreover, there Moreover, are recommendat there are recommendationsions for the broadening for the of broadening national and of nationalinternational and internationallegislation to legislation to protect Cedrela species [7]. protect Cedrela species [7]. Cedrela Knowledge of the chemical compounds and and,, mainly, limonoids present in Cedrela isis importantimportant Cedrela Toona to didifferentiatefferentiate Cedrela and Toona (Endl.) M. M. Roem. Roem. species, species, considering considering that that both both genera genera are are part part of of a achemotaxonomic chemotaxonomic discussion, discussion, based based on on the the inclusion inclusion of of these these genera genera in in the the Cedreleae tribe within Cedreloideae by Harms [[8]8],, and in the Cedreleae tribe under Swietenioidae subfamily by Pen Pennigntonnignton and Styles [[9]9].. Toona According to some authors, the affiliation affiliation of Toona toto SwietenioideaeSwietenioideae is rather problematic, preciselyprecisely because in termsterms ofof secondarysecondary metabolites,metabolites, mexicanolidemexicanolide type limonoids, characteristic to Toona Swietenioideae, areare notnot present in Toona [[1010––1212].]. Thus,Thus, itit could not be included in this subfamily with Cedrela genus, while another aaffirmationffirmation is that morphological aspects justify the junction of these genera by Harms [[11]11].. Although De Leo et al. [ 13] present a review review of terpenoids of CedrelCedrelaa and Toona, this review focus Cedrela is the chemical composition of only Cedrela species, besides current the structural classificationclassification of the limonoids isolated until now and carry out a brief discussion on the difference difference between Cedrela and Toona Toona atat limonoidslimonoids pointpoint ofof view.view. As reported by Tan andand LuoLuo [[1144],], MeliaceaeMeliaceae speciesspecies attractattract considerableconsiderable attention from the chemistry andand biologybiology researchresearch community community because because of of possible possible biological biological activities, activities, mainly mainly related related to theto the presence presence of characteristicof characteristic limonoid limonoid compounds compound ofs thisof this family. family. Limonoids are are a group a group of modified of modified triterpenes, triterpenes, also known also as known tetranortriterpenoids. as tetranortriterpenoids. This class Thisof compounds class of compoundshas highly oxygenated has highly structures, oxygenated derived structures, from a precursor derived from with a 4,4,8 precursor-trimethyl with-17 a- 4,4,8-trimethyl-17-furanylsteroidfuranylsteroid skeleton that is skeletonbiosynthesiz that ised biosynthesized by the acetate by the-mevalonate acetate-mevalonate pathway pathway[15]. These [15]. Theseoxidative oxidative processes processes and methyl and methylgroup rearrangement group rearrangement contribute contribute to structural to structural diversity. diversity. It is worth It ismentioning worth mentioning that limonoids that limonoids can also can be alsofound be foundin Rutaceae, in Rutaceae, Cneoraceae, Cneoraceae, Ptaeroxylaceae, Ptaeroxylaceae, and andSimaroubaceae Simaroubaceae famil families;ies; however however,, they they are are especially especially abundant abundant and and structurally structurally diversified diversified in in the Meliaceae family [[1166]] Overall, thethe following following biological biological activities activities are describedare described for the for Meliaceae the Meliaceae family,which family, are which reported are forreported the genus for theCedrela genus[17 ]:Cedrela antiviral, [17] anthelmintic,: antiviral, anthelmintic, anti-rheumatic, anti anti-cancer,-rheumatic, andanti anti-inflammatory-cancer, and anti- action,inflammatory and antifeedant action, and and antifeedant insecticidal and eff ectsinsecticidal [4,14]. effects [4,14]. The aims of this review were to carry out a survey of the citations reported in the literature to date about species of the genus Cedrela, as well as to provide a foundation for further studies and the Molecules 2020, 25, 5401 3 of 34 Molecules 2020, 25, x FOR PEER REVIEW 3 of 34 The aims of this review were to carry out a survey of the citations reported in the literature to date about species
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