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Chemical systematics of mulberry: Phenylpropanes and aromatic polyketones

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https://www.eduzhai.net International Journal of Plant Research 2017, 7(2): 39-47 DOI: 10.5923/j.plant.20170702.03 Chemosystematic Aspects of the Moraceae Family: Phenylpropanoids and Aromatic Polyketides Adriana Lima de Sousa1,*, Cibele Maria Stivanin de Almeida2, Maria Auxiliadora Coelho Kaplan3, Rodrigo Rodrigues de Oliveira2 1Instituto Federal Fluminense Campus Campos Guarus, Campos dos Goytacazes, Brazil 2Laboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro-UENF, Campos dos Goytacazes, Brazil 3Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Bl. H, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, Brazil Abstract The present study discusses the evolutionary status of Moraceae, from the perspective of chemical features of phenolic micromolecules. A chemosystematics analysis points to affinities between genera and tribe belonging to the Moraceae family, by correlation of the protection parameters of micromolecule hydroxyls resulting from the mixed pathway (acetate/shikimate) and the shikimate pathway. The phenylpropanoid and aromatic polyketide hydroxyl groups are mainly protected by prenylation and methylation mechanisms. A chemometric analysis (grouping and factor analyses) was used to evaluate the evolutionary relationships of the Moraceae genera and tribe, and it was possible to establish taxonomic relationships for the systematic characterization of the Moraceae family through the chemosystematic data. The results of the chemosystematic study suggest evidence that the Trilepisium genus is inadequately classified in the Dorstenia tribe and that the Streblus genus does not belong to the Moreae tribe. In addition, this chemosystematic study confirms the advanced status of Moraceae and legitimization of intrafamiliar classification. Keywords Moraceae, Chemotaxonomy, Micromolecules, Mixed pathway, Shikimate pathway 1. Introduction The Moraceae family consists in monophyletic taxa [1-3], constituted by a group of cosmopolitan species, comprising about 1500 species [4, 5]. According to APG IV (2016) [6], this family is classified as Rosales. Moraceae species present an impressive range of breeding systems and pollination syndromes, as well as enormous variations in growth [2-3, 7-9]. Furthermore, they present a great diversity of anatomical and morphological characteristics, in addition to floral complexity [4, 10]. The intrinsic diversity of species belonging to the Moraceae family culminates in classification conflicts among its systematics, based on morphological and anatomical characters, as proposed by the researchers Rohwer (1993) and Berg (2001) [11-13] versus systematics based on evolutionary relationships and molecular phylogeny introduced by Dätwyler and Weiblen (2004), Beg (2005) and Clement and Weiblen (2009) [2, 3, 8]. The Moraceae systematic classification is still not resolved, due to suprageneric and infrageneric relationships. * Corresponding author: adrianalima@iff.edu.br (Adriana Lima de Sousa) Published online at https://www.eduzhai.net Copyright © 2017 Scientific & Academic Publishing. All Rights Reserved In view of this, we conjecture that the systematic classifications of the Moraceae family based only on morphological and phylogenetic data are insufficient to explain why this taxon “is related to mulberry and bread-fruit” [10]. There are still questions to be answered so that the evolutionary history of Moraceae can be traced. It has been questioned at what point in their history was insect pollination inserted [1-3, 5, 8, 12] and what are the geographical and temporal origins of this family [14-16]. In this context, chemosystematics can contribute to the study of the positioning of Moraceae family genera as a conspicuous and complementary tool. Chemosystematics represents the integration of chemical data and organism morphology dependent on the association of genetic inheritance, and geographic and environmental regulators [17]. The special metabolism stimulated along the angiosperm adaptive process as a defense subterfuge, consisting of micromolecules, is noteworthy, rich in structural diversity and biosynthesized in metabolic pathways derived from the primary metabolism [17, 18]. Chemical evolution in angiosperms is represented in terms of evolutionary channelling [19, 20], in which flavonoid biosynthesis developed prior to lignin biosynthesis [17]. The Moraceae metabolism is conspicuous in the production of metabolites 40 Adriana Lima de Sousa et al.: Chemosystematic Aspects of the Moraceae Family: Phenylpropanoids and Aromatic Polyketides from the mixed pathway (acetate/shikimate) compared to the shikimate pathway [21]. The high heterogeneity exerted by flavonoid derivatives corroborates Dalghren (1980) in his classification for Angiosperms [22]. In angiosperms, evolutionary diversity is characterized by molecular protection processes in response to oxidative degradation [17-20, 23]. This occurs in the Moraceae family species concerning phenolic hydroxyls, resulting from the shikimate and the mixed pathway, alongside phenolic hydroxyls produced by methylation, glycosylation and prenylation [21]. Moraceae species present abundant metabolites resulting from the mixed pathway, with unprotected oxylic groups. Prenylated flavonoids, such as flavone, flavonol, flavanone, chalcone, stilbene and diels alder adducts are noteworthy in this context. In the same way, micromolecules originating from the shikimate pathway, coumarins and lignans, have a majority of unprotected oxylic groups. Although this taxon does not present a key chemo marker, evolutionary advancement index evaluations provide valuable chemosystematic information. With this in mind, the chemosystematic aspects of phenylpropanoids and aromatic polyketides biosynthesized by Moraceae species were evaluated herein, according to the evolutionary advancement parameters regarding hydroxyl protection parameters. These data were used for similarity predictions between genera and in the understanding of Moraceae evolutionary chemistry. 2. Materials and Methods 2.1. Chemosystematic Methodology Chemical data were collected from an extensive literature survey regarding Chemical Abstracts, via Scifinder, covering the range from 1907 to 2014. Phenylpropanoids and aromatic polyketides identified in Moraceae species were listed and submitted to the chemosystematic methodology. It is worth noting that genera organization is based on recent phylogenetic studies conducted by taxonomists Dätwyler and Weiblen (2004) both specialists in Moraceae species. The evolutionary advancement indices for Moraceae genera related to phenylpropanoids and hydroxyl and aromatic polyketides hydroxyl protection mechanisms were determined as proposed by Gottlieb et al. [16] and Emerenciano [24]. These parameters can provide chemical advancements for Moraceae in relation to plant evolution. In addition, they also denote important ecological information regarding adaptive responses and point towards evolutionary trends. The chemical parameters for micromolecules resulting from the mixed and the shikimate pathways regarding O-glycosyl (AEG), O-methyl (AEM), O-prenyl (AEP), Total O-Protection (AEPT), as well as Total O-unprotection (AEUT), were calculated by Equations 1, 2, 3, 4 and 5, respectively. AEG= ∑ IG NO (1) AEM= ∑ IM NO (2) AEPren= ∑ IPren NO (3) AEPT= ∑ IPT NO (4) AEUT= ∑ IUT NO (5) The abbreviations used were as follows: NO: Number of occurrences IG: Number of groups O-glycosyl/ Total number of oxylic groups IM: Number of groups O-methyl/ Total number of oxylic groups IPren: Number of groups O-prenyl/ Total number of oxylic groups IPT: Number of groups oxilicos protected/ Total number of oxylic groups IUT: Number of groups oxilicos unprotected/ Total number of oxylic groups 2.2. Multivariate Analysis In the present study the following statistical approaches were applied: factorial analysis and cluster analysis to explain observed similarities among Moraceae genera and tribes. The former provides tools to analyse the interrelationships (correlations) of a large number of variables, defining sets of variables which are strongly interrelated, known as factors (representing dimensions which summarize or explain the original set of observed variables). The main purpose of the second approach is to aggregate objects based on their characteristics, by recognizing and indicating relationship patterns [25]. The statistical analyses were conducted with Statistica® 7 for Windows. 3. Results and Discussion An estimated occurrence frequency of 404 phenylpropanoids and 1827 aromatic polyketides are listed in the Moraceae database. Moraceae metabolism shows a rich bioproduction of phenolic micromolecules preferably by the mixed (acetate/shikimate) pathway, instead of the shikimic acid derivative pathway, supporting the hypothesis that evolutionary channelling occurred in angiosperms. The occurrence frequency of these compounds in Moraceae genera is detailed in Tables 1 and 2. The chemometric exploration of evolutionary specialization and oxidation advancement parameters of phenylpropanoids and aromatic polyketides consisted in the observation of the similarities between genera, through a factorial and a cluster analysis. However, regarding hydroxyl protection, aromatic polyketides are mostly unprotected, and phenylpropanoids show peculiar protection patterns in each of the investigated genera. It must be considered that derivative protection systems must have evolved at the same time with International Journal of Plant Research 2017, 7(2): 39-47 41 micromolecular diversification. The hydroxyl protection and the hydroxyl protection indices of the tribes are indices of the evaluated genera are summarized in Table 3 displayed in Table 4. Table 1. Occurrence frequency of aromatic polyketides in Moraceae genera Mixed pathway: aromatic polyketides Label Moraceae Genera Au Mo Flg Flc Ch Di Fon Fdol Fol Fl Fla Dih Dip I E Na Ca Ada A1 Artocarpus 9 51 - 1 83 9 549 - 21 58 - - - 3 77 1 29 13 A2 Batocarpus - - - - -- 2 - - - - - - -- - - - A3 Clarissa - - - - -- 2 - - - - - - -1 - - - A4 Hulletia - - - - - - - - - - - - - -- - - - A5 Parartocarpus - - - - 9- 5 - - 5 - - - -- - - - A6 Prainea - - - - - - - - - - - - - -- - - - A7 Treculia - - - 24- 1 - 1- - - - -- - 2 - C1 Antiaris - - - - 12 - - - 3 17 - - - -- - - - C2 Antiaropsis - - - - -- - - - - - - - -- - - - C3 Castila - - - - - - - - - - - - - -- - - - C4 Helicostylis - - - - -- - - - - - - - -- - - - C5 Maquira - - - - - - - - - - - - - -- - - - C6 Mesogyne - - - - - - - - - - - - - -- - - - C7 Naucleopsis - - - - - - - - - - - - - -- - - - C8 Perebea - - - - - - - - - - - - - -- - - - C9 Poulsenia - - - - - - - - - - - - - -- - - - C10 Pseudolmedia - - - - - - - - - - - - - -- - - - C11 Sparratosyce - - - - - - - - - - - - - -- - - - D1 Bosqueiopsis - - - - - - - - - - - - - -- - - - D2 Brosimum - 1 - 26- 2 - - 7 14 1 - 71 - 1 7 D3 Dorstenia - - - - 52 - 25 - 13 14 1 - - -- - - 1 D4 Helianthostylis - - - - - - - - - - - - - -- - - - D5 Scyphosyce - - - - -- - - - - - - - -- - - - D6 Trilepisium - - - - 21 3 - - - - - - 1- - 1 - D7 Trymatococcus - - - - - - - - - - - - - -- - - - D8 Utsetela - - - - - - - - - - - - - -- - - - F1 Ficus - - - - 3 2 26 1 24 3 - - - 17 1 5 16 - M1 Bagassa - 8 2 - -4 - - - 1 - - - -5 - - - M2 Bleeckrodea - - - - -- - - - - - - - -- - - - M3 Broussonetia 4 2 - - 26 2 39 - 51 6 44 - 41 - 1 - 1 1 M4 Fatoua - - - - 3- - - - - - - - -- - - - M5 Maclura - - - - 17 4 - 10 10 - - - 30 3 - - - M6 Milicia - 1 - - -- 4 - - - - - - -- - - - M7 Morus 4 39 - - 1 12 44 - 35 15 1 - - - 17 10 - 32 M8 Sorocea - 1 - - 15 5 - 2- - - - - 1 - - 38 M9 Streblus - - - - -2 2 - 11 - - - - 5- - 2 - M10 Trophis - - - 5 -- - - - - - - - -- - - - Identified aromatic polyketides categories: Fl=Flavanone; Fla=Flavan; DiH= Diarylheptanoid; Dip= Diarylpropanoid; I=Isoflavonoid; E=Stilbene; An= Anthocyanin; Ca= Catechin; Ada= Diels-Alder adducts; Au=Aurone; Mo=Moracine; Flg= Flavolignan; Flc= Flavocoumarin; Ch=Chalcone; Di= Dihydroflavonol; Fon=Flavone; Fdol= Flavanodiol; Fol=Flavonol. 42 Adriana Lima de Sousa et al.: Chemosystematic Aspects of the Moraceae Family: Phenylpropanoids and Aromatic Polyketides Table 2. Occurrence frequency of phenylpropanoids in Moraceae genera Label A1 A2 A3 A4 A5 A6 A7 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 D1 D2 D3 D4 D5 D6 D7 D8 F1 M1 M2 M3 M4 M5 M6 M7 M8 M9 M10 Shikimate pathway: phenylpropanoids Moraceae Genera CA BA Phe Artocarpus 5 8 8 Batocarpus 0 0 0 Clarissa 0 0 0 Hulletia 0 0 0 Parartocarpus 0 0 0 Prainea 0 0 0 Treculia 1 2 0 Antiaris 2 3 1 Antiaropsis 0 0 0 Castila 0 0 0 Helicostylis 0 0 0 Maquira 0 0 0 Mesogyne 0 0 0 Naucleopsis 0 0 0 Perebea 0 0 0 Poulsenia 0 0 0 Pseudolmedia 0 0 0 Sparratosyce 0 0 0 Bosqueiopsis 0 0 0 Brosimum 3 1 1 Dorstenia 1 0 1 Helianthostylis 0 0 0 Scyphosyce 0 0 0 Trilepisium 2 2 0 Trymatococcus 0 0 0 Utsetela 0 0 0 Ficus 7 17 0 Bagassa 0 0 0 Bleeckrodea 0 0 0 Broussonetia 10 2 1 Fatoua 0 0 1 Maclura 0 0 0 Milicia 0 0 0 Morus 10 1 0 Sorocea 0 1 0 Streblus 3 3 0 Trophis 0 0 0 Lig Co 2 2 0 0 0 0 0 0 0 0 0 0 0 5 12 4 0 0 0 0 0 0 0 3 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 39 0 108 0 0 0 0 0 0 0 0 0 0 7 16 0 0 0 0 21 10 0 19 0 0 0 0 0 11 0 0 45 2 0 0 Identified phenylpropanoid categories: CA= Cinnamic acid; BA= Benzoic acid; Phe= Phenylpropene= Lig= Lignans; Co= Coumarin. International Journal of Plant Research 2017, 7(2): 39-47 43 Table 3. Values of the evolutionary protection and unprotection mixed pathway and shikimate pathway advancement parameters of Moraceae genera Tribes Artocarpeae Genera Artocarpus Batocarpus Clarisia Hulletia Parartocarpus Prainea Treculia Mixed pathway: Aromatic polyketides AEG AEM AEP AEPT AEUT 0.0073 0.0000 0.0000 0.0697 0.1250 0.2778 0.1440 0.2500 0.0000 0.2188 0.3750 0.2778 0.7600 0.6250 0.7222 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.2857 0.2857 0.6429 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 10.000 Shikimate pathway: Phenylpropanoids AEG AEM AEP AEPT AEUT 0.0192 0.0000 0.0000 0.2910 0.0000 0.0000 0.0769 0.0000 0.0000 0.3038 0.0000 0.0000 0.6577 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.3125 0.3125 0.625 0.375 Castilleae Antiaris Antiaropsis Castila Helicostylis Maquira Mesogyne Naucleopsis Pereba Poulsenia Pseudolmedia Sparratosyce 0.0141 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.2141 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0078 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.2359 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.7641 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0227 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.5341 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.1364 0.0000 0.0000 0.0000 1.0000 0.0000 1.0000 0.0000 0.0000 0.0000 0.0000 0.7008 0.0000 0.0000 0.0000 1.0000 0.0000 1.0000 0.0000 0.0000 0.0000 0.0000 0.2992 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 Dorstenieae Bosqueiopsis Brosimum Dorstenia Helianthostylis Scyphosyce Trilepisium Trymatococcus Utsetela 0.0000 0.0051 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.1075 0.0211 0.0000 0.0000 0.1250 0.0000 0.0000 0.0000 0.1129 0.2025 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.2255 0.2181 0.0000 0.0000 0.1250 0.0000 0.0000 0.0000 0.7745 0.7866 0.0000 0.0000 0.8750 0.0000 0.0000 0.0000 0.0000 0.0045 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.2311 0.2576 0.0000 0.0000 0.1250 0.0000 0.0000 0.0000 0.6023 0.6500 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.8447 0.9273 0.0000 0.0000 0.1250 0.0000 0.0000 0.0000 0.1098 0.0682 0.0000 0.0000 0.8750 0.0000 0.0000 Ficeae Ficus 0.0645 0.0954 0.0415 0.1988 0.7986 0.0390 0.2738 0.1596 0.4723 0.3787 Moreae Bagassa Bleeckrodea Broussonetia Fatoua Maclura Milicia Morus Sorocea Streblus Trophis 0.0000 0.0000 0.0398 0.0000 0.0300 0.0000 0.0606 0.0085 0.1561 0.0000 0.0500 0.0000 0.0509 0.0000 0.0205 0.0000 0.0282 0.0000 0.1568 0.0000 0.0167 0.0000 0.0524 0.0833 0.1372 0.2167 0.0821 0.1805 0.0000 0.0000 0.0667 0.0000 0.1434 0.0833 0.1646 0.2167 0.1095 0.2268 0.3129 0.0000 0.8333 0.0000 0.8518 0.9167 0.8815 0.7833 0.8089 0.7883 0.6871 0.0000 0.0000 0.0000 0.0720 0.0000 0.0000 0.0000 0.0606 0.0000 0.0535 0.0000 0.0000 0.0000 0.2955 0.3458 0.0000 0.0000 0.1439 0.0000 0.1403 0.0000 0.0000 0.0000 0.1742 0.3167 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.5985 0.7000 0.0000 0.0000 0.2045 1.0000 0.2126 0.0000 0.0000 0.0000 0.3845 0.3125 0.0000 0.0000 0.7955 0.0000 0,7119 0.0000 Identified indices: AEG: O-glycosylation; AEM: O-methylation, AEP: O-prenylation; AEPT: Total O-Protection; AEUT: Total O-unprotection. 44 Adriana Lima de Sousa et al.: Chemosystematic Aspects of the Moraceae Family: Phenylpropanoids and Aromatic Polyketides Table 4. Values of the evolutionary protection and unprotection mixed pathway and shikimate pathway advancement parameters of Moraceae tribes Tribes Artocarpeae Castilleae Dorstenieae Ficeae Moreae Artocarpeae Castilleae Dorstenieae Ficeae Moreae AEG 0.0073 0.0141 0.0051 0.0645 0.295 0.0192 0.0227 0.0045 0.039 0.1861 Mixed pathway: Aromatic polyketides AEM 0.4725 AEP 0.6797 AEPT 1.1573 0.2141 0.0078 0.2359 0.2536 0.3154 0.5686 0.0954 0.0415 0.1988 0.3064 0.7689 1.3239 Shikimate pathway: Phenylpropanoids 0.6035 0.3894 0.9288 0.5341 2.1364 2.7008 0.6137 1.2523 1.8970 0.2738 0.1596 0.4723 0.9255 0.4909 2.7156 AEUT 3.5501 0.7641 2.4361 0.7986 6.5509 1.0327 0.2992 1.0530 0.3787 2.2044 Identified indices: AEG: O-glycosylation; AEM: O-methylation, AEP: O-prenylation; AEPT: Total O-Protection; AEUT: Total O-unprotection. The factorial analysis of the evaluated Moraceae genera combines Factor 1 with O-Glycosylation (mixed pathway), O-Glycosylation (shikimate pathway) and O-Unprotection (shikimate pathway). Factor 2 consists of O-Prenylation (shikimate pathway), Total O-protection (shikimate pathway) and O-Prenylation (shikimate pathway). Factor 3 is composed of O-Prenylation (Mixed pathway), Total O-Protection (Mixed pathway), O-Unprotection (Mixed pathway) and O-Prenylation (Mixed pathway). Finally, Factor 4 is founded on the systematic classification of genera and tribes, based on Dätwyler and Weiblen [2]. The bidimensional diagram displayed in Figure 1 shows the factorial analysis of the 37 Moraceae genera, demonstrating dispersion among them. It is clearly observable that the genera for which there is no number of occurrence of micromolecules in one pathway overlap between -0.5 and -1.0. It is noteworthy that the factorial analysis was useful in reducing the number of data, by grouping the variables (evolutionary advancement parameters) into the factors, thus favoring a chemosystematic analysis of the genera of the Moraceae family. In addition, corroborating previous analyses [2, 21], the Trilepisium genus is unrelated to other Dorstenieae genera. This is probably due to the fact that Dorstenia and Brosimum widely apply the subterfuge of hydroxyl protection of the shikimate pathway, by methylation and preferably by prenylation, while in Trilepisium phenolic micromolecule hydroxyls are usually unprotected. When they display protection, this is due to methylation. The genera from Moreae tribe are quite scattered throughout the graph displayed in Figure 1, which can be related to their high morphological and floral variety, which allowed for the bioproduction of many metabolites. However, the proximity of Ficus and Broussonetia is worth mentioning. Both genera have very close evolutionary advancement parameters referring to the protection of micromolecules resulting from the shikimate pathway: AEM Ficus: 0.2738, AEM , Broussonetia: 0.2955 AEP Ficus: 0.1596, AEP Broussonetia: 0.1742, AEUT Ficus: 0.3787, AEUT Broussonetia: 0.3845 0,3845. After a preliminary analysis, the genera with no metabolite records in the literatures were removed. Thus, when comparing Factors 1 and 3, displayed in Figure 2, results were very similar to the previous graph. A high dispersion among genera is also verified. Thus, the distance of Trilepisium to other Dorstenieae genera is clearly noted. The ratification of this evidence is associated with differences in Trilepisium protection patterns, both among metabolites arising from the mixed pathway as among metabolites originating from the shikimate pathway. While hydroxyls of phenolic micromolecules bioproduced in the shikimate pathway of the Trilepisium genus are the most unprotected, Dorstenia and Brosimum possess metabolites displaying high levels of protection, especially by prenylation. Similarly, phenolic metabolites from the mixed pathway are also unprotected, but when protection occurs in Trilepisium, it is by methylation, while Brosimum shows hydroxyl protection by methylation or prenylation, and Dorstenia preferably by prenylation. Through this analysis, the dispersion among Moreae genera can be observed, which differ from each other basically because they show different patterns of hydroxyl modulations. However, it can be observed that Milicia e Sorocea are related, due to protection of micromolecules resulting from the mixed pathway, that present high index of unprotection and close O-prenylation: AEP Milicia: 0.2167, AEP Sorocea: 0.1805, while Batocarpus and Paratocarpus are close as result of a similar O-prenylation index : AEP Batocarpus: 0.2500, AEP Paratocarpus: 0.2857. Among Moreae genera, Clarisia and Artocarpus occur closely, with a very close index of Total O-unprotection: AEUT Clarisia: 0.722, AEUT Artocarpus: 0.760. Ficeae presents correlations with Moreae genera, because both have high hydroxyl unprotection values in common and, however tenuous, phenolic hydroxyl protection by glycosylation. International Journal of Plant Research 2017, 7(2): 39-47 45 The cluster analysis by Ward's method allowed for the and Castilleae. The second group consists of a grouping of identification of two main groups (Figure 3). The first group the Dorstenieae, Ficeae and Moreae genera. is divided into three genera subgroups, namely Artocarpeae 3,5 3,0 C5 C7 2,5 D3 2,0 D2 1,5 M4 FACTOR2 1,0 A7 0,5 M8 C1A1 M3 F1 0,0 -0,5 MM1M02D1DD8C754C1C1CC9816043A2A64 M6 M5 A5A2 A3 D6 -1,0 M7 M9 -1,5 -2 -1 0 1 2 3 4 FACTOR1 Figure 1. Bidimensional diagram (Factor 1 x Factor 2) displaying the interrelationships between the 37 Moraceae family genera analyzed in the present study 3 2 A2 A5 1 M9 M6M8 M5 M7 Factor 3: 18,63% 0 D3 D2 F1 M1 M3 A3 -1 A1 D6 M4 -2 C1 A7 -3 -5 -4 -3 -2 -1 0 1 2 3 Factor 1: 33,46% Figure 2. Bidimensional diagram (Factor 1 x Factor 3) displaying the interrelationships between Moraceae family genera analysed in the present study 46 Adriana Lima de Sousa et al.: Chemosystematic Aspects of the Moraceae Family: Phenylpropanoids and Aromatic Polyketides A1 A2 A3 A5 A7 C1 D2 D3 D6 F1 M1 M3 M4 M5 M6 M7 M8 M9 0 20 40 60 80 100 120 140 160 180 Linkage Distance A1 – Artocarpus; A2 – Batocarpus; A3 – Clarissa; A5 – Parartocarpus; A7 – Treculia Representatives of the Castileae tribe: C1 – Antiaris; D2 – Brosimum; D3 – Dorstenia; D6 – Trilepisium; F1 - Ficus; M1 – Bagassa; M3 – Broussonetia; M4 – Fatoua; M5 – Maclura; M6 – Milicia; M7 – Morus; M8 – Sorocea; M9 – Streblus; M10 – Trophis. Figure 3. Dendrogram of 37 Moraceae family genera analysed in the present study (Ward’s method based on Euclidean Distances) 4. Conclusions ACKNOWLEDGEMENTS This chemosystematic study greatly contributes to knowledge on the Moraceae family and ratifies that the evolutionary and oxidative advance parameters of Moraceae have systematic values. Analyses of the chemosystematic evolutionary advancement parameters of this family showed a high incidence of aromatic polyketides, with most hydroxyls unprotected, characterizing the primitive positioning of the Moraceae family. Phenylpropanoids have a high variety of hydroxyl protection and each genus showed a particular hydroxyl protection pattern. In sum, the chemosystematic data of phenolic micromolecules presented both similarities and dissimilarities between Moraceae genera and tribes. The main conclusions obtained herein were the consolidation that the Trilepisium genus forms a clade unlinked to the other genera of the Dorstenieae tribe, and that the Streblus genus is a discrepancy of the Moreae tribe and consist in a polyphyletic group. 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