& Bioch ial em b ic ro a c l i T M e f c de Jesus Marques et al., J Microb Biochem Technol 2015, 7:6 h o Journal of n l o a n l o r DOI: 10.4172/1948-5948.1000234 g u y o J ISSN: 1948-5948 Microbial & Biochemical Technology Research Article Article OpenOpen Access Access Occurrence and Distribution of Polyphenolics in Species of Deguelia (Leguminosae) Edson de Jesus Marques1, João Carlos da R Bastos Serafim2, Bruno Brito Lemes2, Marly Fernandes A Carvalho2, Madson de Godoi Pereira2 and Lourdes Cardoso de Souza Neta2* 1Departamento de Ciências Exatas e da Terra , Universidade do Estado da Bahia, Alagoinhas, Bahia, Brazil 2Departamento de Ciências Exatas e da Terra I, Universidade do Estado da Bahia, Salvador, Bahia, Brazil Abstract The species of Deguelia (Papilonoidae Leguminose) genus are recognized for producing polyphenolic secondary metabolities that are predominantly classified as isoflavonoids. The study about the distribution of these secundary metabolities in species of Deguelia genus is very important for understanding the chemosystematic at genus level. Additionally, it has been reported that polyphenolics isolated from Deguelia present many desirable biological effects against human diseases and agricultural pests. Thus, this paper reviewed the occurrence and distribution of polyphenolics in species of Deguelia and evidenced the biological properties of these compounds. Keywords: Deguelia (Papilonoidae Leguminosae); Polyphenolics; The species Deguelia sect. is mainly distributed in the Northern Leguminosae; Papilionoideae states, being found in Pará, Roraima, Amapa, Rondônia, Amazonas and Acre. D. nitidula is one of the few Deguelia sect. species found in other Introduction regions such as Midwestern Goiás and Mato Grosso; Northeastern Deguelia genus belongs to Papilionoideae subfamily, Leguminosae region in Maranhão and Piauí and Southeastern region in Minas Gerais family and comprises 20 species mainly distributed in South America and São Paulo. D. scandens is also found in Maranhão [1,2]. [1,2]. Some of them are used by Amazon indigenous population due Deguelia genus polyphenolics to its ictiotoxic properties, such as Deguelia duckeana, known as “cipó cururu” or “timbó” [3], D. utilis and D. rufescens var. urucu, commonly Deguelia species are rich in polyphenolics secondary metabolites known as “timbó branco” and “timbó vermelho”, respectively [4,5]. such as chalcones, stilbenes, isoflavonoids (rotenoids, isoflavones, Their insecticide and ichthyotoxic activities are attributed to rotenoids 4-hydroxy-3-phenylcoumarins, isoflavan and isoflavanones) and presence in its roots [4]. Deguelia species are rich in polyphenolic flavonoids derivatives (flavanones and dihydroflavanols). which demonstrate many biological activities such as leishmanicidal Rotenoids [6], cytotoxic against Artemia salina [3], antitumoral [7], antioxidant [8], phytotoxicity [9], antimicrobial [10,11] and vasorelaxant effect The review detected the presence of thirty four rotenoids in [12], among others. In this context, the aim of this paper is to review Deguelia species (Compounds 1-30 and 103-106, Figure 1). Deguelia Deguelia polyphenolics and biological potential of their species. sect. species was mainly isolated in Brazilian and Peruvian Amazon forest: D. utilis [13,14], D. negrensis [15], D. amazônica [16] and Cubé Deguelia species distribution in Brazil resin, formed by mixing D. utilis and D. rufescencs var. urucu [17]. Seventeen brazilian Deguelia species are distributed into two Thedehydrorotenone (1) was also the only rotenoid isolated from sections, based on morphological characters, specially the number of Multiovulis section D. densiflora species [7]. These compounds were eggs in the ovary: Deguelia sect. Multiovulis A.M.G. Azevedo comprises predominantly found in the roots, followed by the stems and aerial five species containing 7-15 eggs per ovary: Deguelia costata (Benth.) parts of these species. Rotenone (1) was the most widely distributed in A. M. G. Azevedo & R. A. Camargo, D. densiflora (Benth.) A. M. G. Deguelia species (Figure 1). Azevedo ex M. Souza, D. hastchbachii (Benth.) A.M.G. Azevedo, D. longeracemosa (Benth.) A.M.G. Azevedo and D. spruceana (Benth.) Stilbenes A. M. G. Azevedo & R. A. Camargo, while species with six eggs per Currently, eighteen stilbenes (compounds 31-47 and 109, Figure ovary are allocated in Deguelia sect. Deguelia: D. amazonica Killip, D. 1) and their derivatives have been isolated from Deguelia genus. The angulata (Ducke) A.M.G. Azevedo & R.A. Camargo, D. utilis (A. C. Sm.) A. M. G. Azevedo, D. scandens Aubl., D. negrensis (Benth.) Taub. [Magalhães], D. duckeana A. M. G. Azevedo, D. rariflora (Mart. ex *Corresponding authors: Lourdes Cardoso de Souza Neta, Departamento de Benth.) G. P. Lewis & Acev.-Rodr., D. urucu (Killip & A. C. Sm.) A. M. Ciências Exatas e da Terra I, Universidade do Estado da Bahia, Salvador, Bahia, G. Azevedo & R. A. Camargo, D. nitidula (Benth.) A. M. G. Azevedo & Brazil, Tel: 71 3117-2200; E-mail: [email protected] R. A. Camargo, D. glaucifolia A. M. G. Azevedo, D. dasycalyx (Harms) Received September 11, 2015; Accepted October 01, 2015; Published October A. M. G. Azevedo & R. A. Camargo. Many of these species have 08, 2015 Lonchocarpus sp and Derris sp. synonyms [1,2]. Citation: de Jesus Marques E, da R Bastos SerafimJC , Lemes BB, Carvalho MFA, Among Multiovulis sect. species, three occur mainly in two brazilian de Godoi Pereira M, et al. (2015) Occurrence and Distribution of Polyphenolics in Species of Deguelia (Leguminosae). J Microb Biochem Technol 7: 327-333. regions: Southeastern, in the states Espírito Santo, Minas Gerais and doi:10.4172/1948-5948.1000234 Rio de Janeiro (D. costata, D. hatchibachii and D. longeracemosa) and Northern, in Amapá, Amazonas and Pará (D. densifloraand D. Copyright: © 2015 de Jesus Marques E, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which spruceana). However, D. spruceana was also found in the northern permits unrestricted use, distribution, and reproduction in any medium, provided state of Maranhão [1,2]. the original author and source are credited. J Microb Biochem Technol ISSN: 1948-5948 JMBT, an open access journal Volume 7(6): 327-333 (2015) - 327 Citation: de Jesus Marques E, da R Bastos SerafimJC , Lemes BB, Carvalho MFA, de Godoi Pereira M, et al. (2015) Occurrence and Distribution of Polyphenolics in Species of Deguelia (Leguminosae). J Microb Biochem Technol 7: 327-333. doi:10.4172/1948-5948.1000234 OCH3 OCH3 OCH3 J Microb Biochem Technol ISSN: 1948-5948 JMBT, an open access journal O Volume 7(6): 327-333 (2015) - 328 H3CO O OCH3 R OH 35 - D. spruceana [25] 31 - R = H, D . nitidula [17], D. rariflora [21] 33 - D. hatschbachii [10], 32 - R = OCH3, D. nitidula [17], D. duckeana [3] Cubé resin [22] 34 - R = OH, D. hatschbachii [10] O OCH3 O R2 R1 OCH3 H3CO R3 R OR 4 R 44 - R1 = R2 = OCH3, R3 = OH, R4 = H R1 OCH3 38 - R = H, R1 = 45- R1 = H, R2 = R3 = R4 = OCH3 36 - R = OCH3, D. rufescens [9], D. utilis [4] D. utilis [6], D. rufescens [9] 46 - R1= OCH3, R2 = R4 = H, R3 = OH 37 - R = H, D . rufescens [5, 9], D. utilis [5, 20, 23] Cubé resin [22] 39 - R = R1 = H D. utilis [6], D. rufescens [5, 9] R O OR 1 40 - R = R1 = H, D. rufescens [9] O O O OH H CO 41 - R = CH3, R1= H 3 42 - R = R = CH 1 3 47 - Cubé resin [22] D. utilis [6] 43 - D. utilis [6] OH D. nitidula [21] 3 R2 OCH3 OCH OH O OR1 O R 3 O OH O OH O 48 - R1= R2= R3= H, D. duckeana [3] 51 - D. duckeana [3] O 49 - R1= R3= H ; R2= OH, D . duckeana [3], 52 - Cubé resin [22] D. nitidula [17], Cubé resin [22] 50 - R1= H; R2= R3= OH, D . nitidula [17] H3 CO O O O O O OCH3 O O O O 54 - D. densiflora [24] 53 - D. densiflora [24] O O O O O O Glu O OH O O O OR O OCH3 55 - D. spruceana [25], OH D. hatschbachii [10], 56 - R= H, osajin, D . longeracemosa [11] 58 - D. longeracemosa [11] D. longeracemosa [11] 57 - R= CH3 , scandinone, D. hatschbachii [10] O O O O O O O OCH3 R2 R1 OCH3OH OH O R3 OR O 59 - R= H, D. densiflora [7] OCH3 65- R1= ; R2= H; R3= OH, 60 - R= CH3, D. densiflora [7] 61 - D. utilis [20, 23] OCH3 D. spruceana [25], D. hatschabachii [10], D. longeracemosa [11] O O O 66 - R1= ; R2= OH; R3= OCH3 O O O O D. longeracemosa [11] OCH OCH 3 3 O O 67- R1= ; R2,R3= OCH2O 62 - D. densiflora [24] OCH OR 3 O D. longeracemosa [11] OH 63 - R= H, D. spruceana [25] O 68 - R = ; R = H; R = OH D. longeracemosa [11] 1 2 3 H3CO O 64 - R= CH , D. spruceana [25] 3 D. longeracemosa [11] H RO O OH O O O O OH O 80 - D. hatschbachii [10] OCH3 OCH3 OCH3 74- R= H 75- R= Me D. rariflora [21] O O O 73 - D. hatschabachii [10] R2 R3 R1 O O OCH3 OH R2 OH 69- R1= OH ; R2= OCH3, D. longeracemosa [11] O O O R O 70- R1= H ; R2= 1 D. longeracemosa [11] 76- R = OH; R = OMe; R = OMe, OH O 71- R , R = O C H O . longeracemosa [11] 1 2 3 1 2 2 77- R = OH; R = OH; R = OMe 72- R = H ; R = OCH , D. longeraccemosa [11], 1 2 3 81 - D. hatschbachii [10] 1 2 3 78- R = OH; R = OMe; R = OH D. hatschabachii [11] 1 2 3 79- R1= H; R2= OMe; R3= OMe Cubé resin [22] OCH3 H3CO O OH OH OH O 82- D. rufescens [8, 12] OCH3 O O OCH OCH3 OR2 3 H3CO O O O OH OH OH OR1 O R R OH O 83- R1=R2= CH3 OH O 84- R = CH ; R =H, 1 3 2 86- R= 3beta OH D.