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Home , Chrysobalanaceae, Chrysobalanus icaco, Couepia, Exellodendron, Licania, Parinari

Revista Brasileira de Farmacognosia Brazilian Journal of Pharmacognosy : traditional uses, 22(5): 1181-1186, Sep./Oct. 2012 phytochemistry and pharmacology

Evanilson Alves Feitosa,1 Haroudo Satiro Xavier,1 Karina Perrelli Randau*,1

Laboratório de Farmacognosia, Universidade Federal de , . Review Abstract: Chrysobalanaceae is a family composed of seventeen genera and about 525 species. In Africa and some species have popular indications Received 16 Jan 2012 for various diseases such as malaria, epilepsy, diarrhea, infl ammations and diabetes. Accepted 25 Apr 2012 Despite presenting several indications of popular use, there are few studies confi rming Available online 14 Jun 2012 the activities of these species. In the course of evaluating the potential for future studies, the present work is a literature survey on databases of the botanical, chemical, Keywords: biological and ethnopharmacological data on Chrysobalanaceae species published since the fi rst studies that occurred in the 60’s until the present day. botany ethnopharmacology

ISSN 0102-695X http://dx.doi.org/10.1590/S0102- 695X2012005000080

Introduction Small fl owers usually greenish-white, cyclic, zigomorphic, diclamides, with a developed receptacle, and petals Chrysobalanaceae was fi rst described by the free, general pentamers, androecium consists of two botanist Robert Brown in his study “Observations, to many free or more or less welded together; systematical and geographical, on the herbarium collected superomedial ovary, bi to tricarpellate, unilocular, usually by Professor Christian Smith, in the vicinity of the Congo, with only one ovule and usually drupaceous. In the during the expedition to explore that river, under the Brazilian Cerrado and in the Amazonian forests from command of Captain Tuckey, in the year 1816” (Salisbury, the species of the Licania can be found. Some of 1818). It is a family composed of seventeen genera and them are known as “oiticica”, and they are oil-producing. about 525 species. These are woody , shrubs and The Cerrado species usually present a very twisted trunk. trees found in tropical and subtropical regions, mainly in In Northeastern Brazil, species of Licania and the New World tropics (Yakandawala et al., 2010). The are known as “oiti”. Other genera of the Amazon region wood is of little advantage due to high rate of silica, but produces the fruit called “pajurá” (Parinarium). Also several species have edible (Prance, 1988). in the Amazon, species of produce a type of nut known as “castanha-de-cutia” (Joly, 1998). Again Material and Methods in Northeast Brazil, many are used as forage potential: icaco, Couepia impressa, Couepia rufa, An extensive search through books and original Couepia uiti, Licania parvifl ora, Licania salzmannii and articles was carried out in this work. The search was Licania tomentosa. In Pernambuco´s Atlantic Jungle performed accessing SciFinder, ScienceDirect, Web of region, they are used as fodder: Couepia impressa and Science, Scielo and NAPRALERT databases, updated to Couepia rufa and on the coast and February 2012. The keywords used for this review were Licania tomentosa (Tabarelli & Silva, 2002). Chrysobalanaceae, Licania, Parinari and the names of Metcalfe & Chalk (1988) describes anatomical all other Chrysobalanaceae genus. More than 90% of the features of some species of Chrysobalanaceae. The references obtained were later consulted. has a closed cylinder of xylem and phloem, and two small adaxial vascular strands, with variations Botany (morphology and microscopy) occurring among genera and species of a single genus. The show paracytic stomata (sometimes only on The Chrysobalanaceae plants have entire leaves, the abaxial surface) and epidermis with mucilaginous hard, provision of alternate, distichous, with stipules. walls, with papillose on abaxial surface; hypoderm is

1181 Chrysobalanaceae: traditional uses, phytochemistry and pharmacology Evanilson Alves Feitosa et al.

present in some species. It has a ramified, peltate, stellate floribunda bark is used in West or glandular hairs. Mesophyll has predominantly a Africa to treat diarrhea and dysentery (Koné et al., dorsiventral traversed by lignified cells, like fiber. Veins 2004), racemosa is used to treat pregnancy with vascular bundles surrounded by sclerenchymatous nausea in Polynesia (Ostraff et al., 2000), and in Latin fibers. Vessel cells with simple perforations without America Licania arborea is used as an antifungal spiral thickening, uni-triseriate bands of apotracheal (Svetaz et al., 2010). In Senegal, a cigarette is prepared parenchyma in heterogeneous rays, and pits bordered from the stem bark of macrophylla used as a in fibers. Silica crystal, isolated or clustered, is present remedy for snake bite (Mohagheghzadeh et al., 2006). into membranes, into epidermis cells, into idioblasts The ethnopharmacological uses of these surrounding veins and in the mesophyll. Secretory species reveal that they present a significant number cavities are also found in some genera. A continuous of indications in South America and Africa, where or discontinuous ring of sclerenchyma encircles the they are distributed. Usually. the popular knowledge vascular cylinder, characterizing the pericycle, and can guide the search for medicinal plants, which cells with U-thickening in transversal section. The occasionally results in the discovery of molecules with main vascular bundle shows variations related to xylem biological activity (Maciel et al., 2002). Therefore, and phloem arrangement. species of Licania and Parinari can be studied for anti- inflammatory activity, diabetes and malaria. Ethnopharmacology Phyto-constituents In folk medicine, Chrysobalanaceae species are used for various purposes. Among those in popular use, There are few studies that address the chemical the species of the genus Licania show the largest number composition of species Chrysobalanaceae beyond genres of biological activities, and are vastly used in Licania and Parinari. Note that there are no studies with as an anti-inflammatory (Pittier, 1978). Most of them other genera of the family as Hirtella, , are cultivated because of its edible fruits (Toledo et al., or . 1982). Early phytochemical studies occurred in the In Northeastern Brazil, Licania species has its 60's and described the presence of aglycone flavonoids leaves used to treat diabetes (Agra et al., 2007), stomach in species of , including two taxa of aches (Albuquerque et al., 2007), diarrhea and dysentery Chrysobalanaceae: Chrysobalanus icaco and Licania (Cartaxo et al., 2010). The stem bark of , rigida, where was identified the myricetin (Chaffaud & which is widespread in Senegal (Ndiaye et al., 2008), is Emberger, 1960). also used to treat diabetes; and also leaves of Hirtella Later, the investigation of 31 species of Parinari racemosa, that is commonly known in the northern Brazil in 1985 presented that they showed a predominance of as “ajirú-do-mato” (Coelho-Ferreira, 2009). flavonoids glycosides based on myricetin (1), quercetin Chrysobalanus icaco, also known as “abajeru”, (2), and kaempferol (3) (Coradin et al., 1985). Other is a medium sized shrub native of the American coast. It phytochemicals studies of Parinari species led to the is used in folk medicine for the treatment of leucorrhoea, isolation and identification of flavonoids with fatty acids bleeding and chronic diarrhea, and is also known for its and their glycosides (Chisholm & Hopkins, 1966; Coradin diuretic, hypoglycemic and antiangiogenic effects (Costa, et al., 1985). The molecules identified in Chrysobalanaceae 1977; Paulo et al., 2000; Vargas-Simon et al., 1997). In are shown in the Table 1. Northern Brazil, its root is used to treat diabetes (Coelho- Phytochemical studies with the genus Licania Ferreira, 2009). shown similarities with other Chrysobalanaceae, Parinari species, like P. curatellifolia and P. resulting in the isolation and characterization of two excelsa, are traditionally used in Africa as a remedy for majority classes of compounds: flavonoids and triterpene dysentery, epilepsy, malaria, toothache and venereal metabolites (Castilho et al., 2005). Isocarthamidin diseases (Uys et al., 2002; Arnold & Gulumian, 1984). The and 4-hydroxybenzoic acid were isolated by the leave of P. curatellifolia is indicated to treat stomachaches powdered stems of P. anamense (Werawattanachai & in Southern Uganda (Ssegawa & Kasenene, 2007). The Kaewamatawong, 2010). Of P. curatellifolia, diterpenes stem bark of P. excelsa is used in Guinea to treat infectious with molecular core ent-kaurene derivative of 15- diseases (Magassouba et al., 2010). In West Africa, its oxozoapatlin (4) were isolated and presented cytotoxic stem bark is popularly known as anthelmintic, and its fruit activity (Lee et al., 1996). In other species, P. campestris, is used to treat diarrhea (Diehl et al., 2004). In it six diterpenes kaurane were also isolated (Braca et al., is used as an antiseptic and to treat malaria (Kamuhabwa 2005). et al., 2000). P. polyandra is also used to treat malaria in Ghana (Asase et al, 2005).

1182 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 22(5): Sep./Oct. 2012 Chrysobalanaceae: traditional uses, phytochemistry and pharmacology Evanilson Alves Feitosa et al.

Biological activities R1 OH O There are studies that show the antihyperglycemic property of some species of Chrysobalanaceae, as HO O O R2 Chrysobalanus icaco (Presta & Pereira, 1987) and P. O OH excelsa, confirming its use in traditional medicine (Ndiaye O OH O et al., 2008). Cytotoxic activity is observed in the pomolic 1 R1=R2=OH 4 acid of Chrysobalanus icaco. Betulinic and oleanolic acid 2 R1=H; R2=OH 3 R1=OH; R2=H of Licania tomentosa, show ability to inhibit the growth and induce apoptosis in the cell line erythroleukemia

(K562), and also to prevent proliferation of Lucena 1, a The study of the phytochemical composition derived vincristine-resistant from K562 (Fernandes et al., of the other genera in the family can contribute to 2003). The root extract of L. michauxii has cytotoxicity the characterization of the major constituents in against cultured human hepatoma (Hep G2) and colon Chrysobalanaceae.

Table 1. Molecules identified in Chrysobalanaceae species. Specie Molecules Reference Licania apetala kaempferol-3-rutinoside, myricetin-3-rhamnoside, myricetin-4’-rhamnoside, quercetin-3- (Braca et al., 2002) rhamnoside, quercetin-3-arabinoside, quercetin-3-galactoside, quercetin 3-glucoside, rutin, taxifolin-3-rhamnoside

Licania arianeae acid 3-O-[6’-O-4-hidroxybenzoyl]-β-D-galactopyranosyl-ursa-12-en-28-óico, acid flavone-6- (Carvalho & Da sulphonic, 4’-O-methyl-5,7-diidroxy-flavone-6-sulphonic. Costa, 2009) Licania densiflora myricetin (1), myricetin-3-rhamnoside, myricetin-3-glucoside, myricetin-3-galactoside, (Braca et al., 1999a; myricetin-4’-methoxy-3-rhamnoside, myricetin-3’,5’-dimethylether-3-rhamnoside, myricetin-3’- Braca, 2001b) methylether-3-galactoside, myricetin-3’-methylether-3-glucoside, myricetin-3’,5’-dimethylether- 3-O-glucoside, myricetin-3-O-α-L-(2’’-O-α-L-rhamnopyranosyl)-rhamnopyranoside-3’,4’- dimethylmyricetin-3-O-β-D-glucopyranoside, quercetin (2), quercetin-3-rhamnoside, quercetin-3-glucoside, narigenin-8-hydroxy-4’-methyl ether, catechin

Licania myricetin-3-galactoside, myricetin-4’-methoxy-3-rhamnoside, myricetin-3,4’-di-O-α-L- (Braca et al., 1999b; heteromorpha rhamnopyranoside, myricetin-4’-methyl ether-3-O-β-D-galactopyranoside, myricetin-4’- Braca et al., 1999c) methoxy-3-galactoside, myricetin-4’-methoxy-3-glucoside, myricetin-7-methyl ether-3,4’-di-O- α-L-rhamnopyranoside, betulinic acid, alphitolic acid Licania licaniaeflora kaempferol-3-(2’’-xylosyl)-rhamnoside, kaempferol-3-rhamnoside, myricetin-3-arabinoside, (Braca et al., 2002, myricetin-3-galactoside, dihidromyricetin-3-rhamnoside, quercetin-3-rhamnoside, quercetin- Braca et al., 2001a, 3-arabinoside, 8-hydroxy-narigenin, taxifolin-3-rhamnoside, oleanolic acid, maslinic acid, Bilia et al., 1996a) oleanolic acid 3-O-arabinoside, betulinic acid, arjunetin, tomentic acid glucosyl ester, pomolic acid, olean-12-en-2α,3β-diol Licania pittieri quercetin (2), quercetin-3-rhamnoside, quercetin-3-arabinoside, quercetin-3-galactoside, (Bilia et al., 1996a; quercetin 3-glucoside, catechin, epicathechin, ursolic acid, oleanolic acid Mendez et al., 1995) kaempferol (3), kaempferol-3-rhamnoside, kaempferol-3-arabinoside, kaempferol-3-(2’’-xylosil) (Bilia et al., 1996a) rhamnoside, hypoletin, 8-hydroxy-eriodictyol, 8-hydroxy-narigenin, myricetin (1), myricetin- 3-rhamnoside, myricetin-3-(2’’-xylosyl)rhamnoside, quercetin (2), quercetin-3-rhamnoside, quercetin-3-arabinoside, quercetin-3-(2’’-xylosyl)rhamnoside Licania tomentosa betulinic acid, licanolide, palmitoeic acid, oleanolic acid, stigmasterol, sitosterol, lupeol, (Castilho & Kaplan, tomentic acid, ursolic acid 2008) Licania carii myricetin-3-rutinoside, myricetin-3-glucoside, myricetin-3-(2’’-xylosyl)rhamnoside, quercetin- (Bilia et al., 1996b) 3-(2’’-xylosyl)rhamnoside, quercetin-3-galactoside, quercetin 3-glucoside, rutin, 2α-hydroxy ursolic acid, betulinic acid, maslinic acid. kaempferol-3-rutinoside, 15-oxozoapatlin-13α-yl-10’α,16’α-dihydroxy-9’α-methyl-20’nor- (Coradin et al., 1985; kauran-19’-oic acid γ-lactone-17’-oate, 13-hydroxy-15-oxozoapatlin, 10α,13α,16α,17- Braca et al., 2005) tetrahydroxy-9α-methyl-15-oxo-20-nor-kauran-19-oic acid γ-lactone, 2α,10α,13α,16α,17- pentahydroxy-9α-methyl-15-oxo-20-nor-kauran-19-oic acid (19,10)-lactone, 3α,10α,13α,16α,17-pentahydroxy-9α-methyl-15-oxo-20-nor-kauran-19-oic acid γ-lactone, 1β,16α,17-trihydroxy-ent-kaurane. Parinari 15-oxozoapatlin (4), 13-methoxy-15-oxozoapatlin, 13-hydroxy-15-oxozoapatlin. (Lee et al., 1996) curatellifolia Chrysobalanus icaco pomolic acid. (Fernandes et al., 2003)

Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 22(5): Sep./Oct. 2012 1183 Chrysobalanaceae: traditional uses, phytochemistry and pharmacology Evanilson Alves Feitosa et al.

carcinoma (Caco-2) (Badisa et al., 2000). Ent-kaurane racemosa, lack of pharmacological studies. Licania diterpenes isolated from the root of P. curattellifolia, tomentosa and Chrysobalanus icaco have activity in vitro show cytotoxicity in vitro against several cancer cell lines in the treatment of multidrug-resistant erythroleukemia, (Lee et al., 1996). P. capensis has moderate cytotoxicity confirming the value of natural products in search of new against cell lines of lung cancer, renal cancer and active substances. We should also watch for the need of melanoma (Fouche et al., 2008). developing countries to research alternative therapies The presence of cytotoxicity may be indicative and substances candidates for drugs to fight diseases of anticancer action of these compounds, further called "neglected". Species such as Parinari excelsa studies are needed to assess the mechanism of action and P. curatellifolia present popular indication in the responsible for cytotoxicity and in vivo evaluation of treatment of malaria, and there are no studies to prove this these molecules and extracts. The presence of cytotoxic statement, while Licania carii, L. pittieri and L. pyrifolia activity of kaurane diterpenes is discussed in many need more studies to prove his action in the fight against studies in different species (He et al., 2009; Hueso- schistosomiasis. Falcón et al., 2010; Lin et al., 2012); Moreover, it appears that the molecules Diterpenes found in P. capensis have antifungal isolated by Chrysobalanaceae, mostly, are flavonoids (Garo et al., 1997) and antimalarial activity, but have and terpenoids. In a particular way, flavonoids and high toxicity (Uys et al., 2002). The hexane extract of terpenes being mentioned in most species of Licania has antibacterial activity against and kaurene diterpene in species of Parinari. Pseudomonas aeruginosa and the ethanolic extract Chrysobalanaceae still presents itself as an against Staphylococcus aureus and Pseudomonas unexplored source for the isolation and characterization of aeruginosa (Zuque et al., 2004). new active substances. Thus, new researches can open new Diterpenes of Chrysobalanus icaco have anti- paths in the discovery of molecules with therapeutic action HIV activity (Gustafson et al., 1991), and aqueous and drug discovery. extract of leaves have a potent genotoxic effect (Ferreira-Machado et al., 2004). References Other activities of the genus Licania are described. Quercetin flavonoids obtained from sheets of Agra MF, França PF, Barbosa-Filho JM 2007. Synopsis of the L. licaniaeflora and L. heteromorpha exhibit antioxidant plants known as medicinal and poisonous in Northeast of activity (Braca et al., 2001a; Montoro et al., 2005). Brazil. Rev Bras Farmacogn 17: 114-140. Licania carii, L. pittieri and L. pyrifolia are toxic against Albuquerque UP, Monteiro JM, Ramos MA, Amorim ELC Biomphalaria glabrata Say, a mollusk involved in the 2007. Medicinal and magic plants from a public reproductive cycle of Schistosoma mansoni Sambon market in northeastern Brazil. J Ethnopharmacol 110: (Bilia et al., 2000). The extract of L. tomentosa has the 76-91. ability to inhibit herpes simplex virus type I acyclovir- Arnold HJ, Gulumian MJ 1984. Pharmacopoeia of traditional resistant (ACVr-HSV1) and interfere with the initial medicine in Venda. J Ethnopharmacol 12: 35-74. process of infection in non-cytotoxic concentrations Asase A, Oteng-Yeboah AA, Odamtten GT, Simmondsb MSJ (Miranda et al., 2002). 2005. Ethnobotanical study of some Ghanaian anti- The fruits of presents anti- malarial plants. J Ethnopharmacol 99: 273-279. inflammatory activity by inhibiting the biosynthesis of Badisa BB, Chaundhuri SK, Pilarinou E, Rutkoski NJ, Hare prostaglandins (Dunstan et al., 1997). Although Licania J, Levenson CW 2000. Prance root species have popular indication as anti-inflamatory, extract induces hsp 70 mRNA and necrotic cell death there are few studies to support this use. in cultured human hepatoma and colon carcinoma cell lines. Cancer Lett 149: 61-68. Conclusion Bilia AR, Ciampi L, Mendez J, Morelli I 1996a. Phytochemical investigations of Licania genus. Flavonoids from Chrysobalanaceae species have indications Licania pyrifolia. Pharm Acta Helv 71: 199-204. in the traditional medicine and treatments for various Bilia AR, Mendez J, Morelli I 1996b. Phytochemical diseases such as malaria, epilepsy, diarrhea, bleeding, investigations of Licania genus. Flavonoids and venereal disease and diabetes. But there are few triterpenoids from Licania carii. Pharm Act Helv 71: studies, both phytochemical and pharmacological, 191-197. which express with larger therapeutic potential of these Bilia AR, Braca A, Mendez J, Morelli I 2000. Molluscicidal and species and chemicals. piscicidal activities of Venezuelan Chrysobalanaceae Chrysobalanus icaco and Parinari excelsa have plants. Life Sci 66: 53-59. results that express their potential on treating diabetes, Braca A, Bilia AR, Mendez J, Morelli I 1999a. Three but other species with popular indications such as Hirtella flavonoids from Licania densiflora. Phytochemistry

1184 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 22(5): Sep./Oct. 2012 Chrysobalanaceae: traditional uses, phytochemistry and pharmacology Evanilson Alves Feitosa et al.

51: 1125-1128. resistant and sensitive leukemia cell lines. Cancer Braca A, De Tomassi N, Mendez J, Morelli I 1999b. Flavonoids Lett 190: 165-169. and triterpenoids from Licania heteromorpha Ferreira-Machado SC, Rodrigues MP, Nunes APM, Dantas FJS, (Chrysobalanaceae). Biochem Syst Ecol 27: 527-530. De Matos JCP, Silva CR, Moura EG, Bezerra RJAC, Braca A, De Tommasi N, Mendez J, Morelli I, Pizza C Caldeira-de-Araujo A 2004. Genotoxic potentiality of 1999c. Three flavonoids from Licania heteromorpha. aqueous extract prepared from Chrysobalanus icaco Phytochemistry 51: 1121-1124. L. leaves. Toxicol Lett 151: 481-487. Braca A, Sortino C, Mendez J, Morelli I 2001a. Trierpenes Fouche G, Cragg GM, Pillay P, Kolesnikova N, Maharaj VJ, from Licania licaniaeflora. Fitoterapia 72: 585-587. Senabe J 2008. In vitro anticancer screening of South Braca A, Bilia A R, Mendez J, Morelli I 2001b. Myricetin African plants. J Ethnopharmacol 119: 455-461. glycosides from Licania densiflora. Fitoterapia 72: Garo E, Maillard M, Hostettmann K, Stoeckli-Evvans H, 182-185. Mavi S 1997. Absolute configuration of a diterpene Braca A, Luna D, Mendez J, Morelli I 2002. Flavonoids lactone from . Helv Chim Acta 80: from Licania apetala and Licania licaniaeflora 538-544. (Chrysobalanaceae). Biochem Syst Ecol 30: 271-273. Gustafson KR, Munro MHG, Cardellina JH, MC Malon JB, Braca A, Abdel-Razik AF, Mendez J, Morelli I 2005. A new Gulakowshi RJ, Cragg GM, Cox PB, Linda SJ 1991. kaurane diterpene dimer from Parinari campestris. HIV inhibitory natural products. 3. Diterpenes from Fitoterapia 76: 614-619. Homalantus acuminatus and Chrysobalanus icaco. Cartaxo SL, Souza MMA, Albuquerque UP 2010. Medicinal Tetrahedron 47: 4547-4554. plants with bioprospecting potential used in semi-arid Hueso-Falcón I, Girón N, Velasco P, Amaro-Luis JM, northeastern Brazil. J Ethnopharmacol 131: 326-342. Ravelo AG, Heras B, Hortelano S, Estevez-Braun A Carvalho MG, Da Costa PM 2009. Outros constituintes 2010. Synthesis and induction of apoptosis signaling isolados de Licania arianeae (Chrysobalanaceae). pathway of ent-kaurane derivatives. Bioorg. Med Brazil J Pharmacogn 19(1B): 290-293. Chem 18: 1724-1735. Castilho RO, Oliveira RR, Kaplan MAC 2005. Licanolide, He F, Xiao WL, Pu JX, Wu YL, Zhang HB, Li XN, Zhao a new triterpene lactone from Licania tomentosa. Y, Yang LB, Chen GQ, Sun HD 2009. Cytotoxic Fitoterapia 76: 562-566. ent-kaurane diterpenoids from Isodon sinuolata. Castilho RO, Kaplan MAC 2008. Constituintes químicos de Phytochemistry 70: 1462-1466. Licania tomentosa Benth. (Chrysobalanaceae). Quim Joly AB 1998. Botânica: introdução à taxonomia vegetal. Nova 31: 66-69. Brasil: IBEP. Chaffaud M, Emberger L 1960. Traité de Botanique Kamuhabwa A, Nshimo C, de Witte P 2000. Cytotoxicity Systematique Vol. II. Paris: Masson, p. 1338-1340. of some medicinal extracts used in Tanzanian Chisholm MJ, Hopkins, CY 1966. Kamloenic acid and other traditional medicine. J Ethnopharmacol 70: 143-149. conjugated fatty acids in certain seed oils. J Am Oil Koné WM, Atindehou KK, Terreaux C, Hostettmann K, Chem Soc 43: 390-392. Traoré D, Dosso M 2004. Traditional medicine in Coelho-Ferreira M 2009. Medicinal knowledge and plant North Côte-d’Ivoire: screening of 50 medicinal plants utilization in an Amazonian coastal community of for antibacterial activity. J Ethnopharmacol 93: 43- Marudá, Pará State (Brazil). J Ethnopharmacol 126: 49. 159-175. Lee I, Shamon L, Chai H, Chagwedera TE, Besterman JM, Coradin L, Giannasi DE, Prance AT 1985. Chemosystematic Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn studies in the Chrysobalanaceae. Flavonoids in AD 1996. Cell-cycle specific cytotoxicity mediated Parinari. Britton 37: 169-178. by rearranged ent-kaurene diterpenoids isolated from Costa OA 1977. Plantas hipoglicemiantes brasileiras II. . Chem-Biol Interact 99: 193- Brasil: Leandra p 63-75. 204. Diehl MS, Atindehou KK, T´er´e H, Betschart B 2004. Lin L, Gao Q, Cui C, Zhao H, Fu L, Chen L, Yang B, Luo Prospect for anthelminthic plants in the Ivory Coast W, Zhao M 2012. Isolation and identification of using ethnobotanical criteria. J Ethnopharmacol 95: ent-kaurane-type diterpenoids from Rabdosia serra 277-284. (Maxim.) Hara leaf and their inhibitory activities Dunstan CA, Noreen Y, Serrano G, Cox PA, Pereira P, Bohlin against HepG-2, MCF-7, and HL-60 cell lines. Food L 1997. Evaluation of some Samoan and Peruvian Chem 131: 1009-1014. medicinal plants by prostaglandin biosynthesis and Maciel MAM, Pinto AC, Veiga Jr VF, Grynberg NF, Echevarria rate ear oedema assays. J Ethnopharmacol 57: 35-36. A 2002. Plantas medicinais: a necessidade de estudos Fernandes J, Castilho RO, Costa MR, Wagner-Souza K, Kaplan multidisciplinares. Quim Nova 25. no.3. MAC, Gattass CR 2003. Pentacyclic triterpenes from Magassouba FB, Diallo A, Kouyaté M, Mara F, Mara O, Chrysobalanaceae species: cytotoxicity on multidrug Bangoura O, Camara A, Traoré S, Diallo AK, Zaoro

Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 22(5): Sep./Oct. 2012 1185 Chrysobalanaceae: traditional uses, phytochemistry and pharmacology Evanilson Alves Feitosa et al.

M, Lamah K, Diallo S, Camara G, Traoré S, Kéita A, hipoglicemiantes. Rev Bras Farm 68: 91-101. Camara MK, Barry R, Kéita S, Oularé K, Barry MS, Salisbury R 1818. "[Review of] Narrative of an expedition to Donzo M, Camara K, Toté K, Vanden Berghe D, Totté J, explore the River Zaire, usually called the Congo, in Pieters L, Vlietinck AJ, Baldé AM 2010. Corrigendum , in 1816, under the direction of Captain J. to “Ethnobotanical survey and antibacterial activity H. Tuckey, R. N". Month Rev 86: 113-129, 292-305. of some plants used in Guinean traditional medicine”. Ssegawa P, Kasenene JM 2007. Medicinal plant diversity J Ethnopharmocol 114: 44-53. and uses in the Sango bay area, Southern Uganda. J Mendez J, Bilia AR, Morelli I 1995. Phytochemical Ethnopharmacol 113: 521-540. investigations of Licania genus. Flavonoids and Svetaz L, Zuljan F, Derita M, Petenatti E, Tamayo G, Cáceres triterpenoids from Licania pittieri. Pharm Acta Helv A, Filho VC, Giménez A, Pinzón R, Zacchino SA, 70: 223-226. Gupta M 2010. Value of the ethnomedical information Metcalfe CR, Chalk L 1988. Anatomy of the dicotyledons: for the discovery of plants with antifungal properties. systematic anatomy of the leaf and stem vol 1. Oxford: A survey among seven Latin American countries. J Clarendon Press. Ethnopharmacol 127: 137-158. Miranda MMFS, Gonçalves JLS, Romanos MTV, Silva FP, Tabarelli M, Silva JMC 2002. Diagnóstico da Biodiversidade Pinto L, Silva MH, Ejzemberg R, Granja LFZ, Wigg de Pernambuco. Recife: Secretaria de Ciência, MD 2002. Anti-herpes simplex virus effect of a seed Tecnologia e Meio Ambiente, Editora Massangana. extract from the tropical plant Licania tomentosa Toledo CL, Kbitzki K, Prance GH 1982. Flora de Venezuela (Benth.) Fritsch (Chrysobalanaceae). Phytomedicine vol IV. Caracas: Ediciones Fundacion Educacion 9: 641-645. Ambiental p 332-406. Mohagheghzadeh A, Faridi P, Shams-Ardakani M, Ghasemi Uys ACU, Malan SF, van Dyck S, van Zyl RL 2002. Y 2006. Medicinal smokes. J Ethnopharmacol 108: Antimalarial compounds from Parinari capensis. 161-184. Bioorg Medic Chem Lett 12: 2167. Montoro P, Braca A, Pizza C, De Tommasi N 2005. Structure– Vargas-Simon G, Arellano-Ostoa G, Garcia-Villanueva E antioxidant activity relationships of flavonoids 1997. Propagación por estacas com hojas de icaco isolated from different plant species. Food Chem 92: (Chrysobalanus icaco) y anatomía del enraizamento. 349-355. Proced Internat Soc Trop Horticul 41: 264-269. Ndiaye M, Diatta W, Sy AN, Dièye AM, Faye B, Bassène E Werawattanachai N, Kaewamatawong R 2010. Chemical 2008. Antidiabetic properties of aqueous barks extract constituents from Parinari anamense. Biochem Syst of Parinari excelsa in alloxan-induced diabetic rats. Ecol 38: 836-838. Fitoterapia 79: 267-270. Yakandawala D, Morton CM, Prance GT 2010. Phylogenetic Ostraff M, Anitoni K, Nicholson A, Booth GM 2000. relationships of the Chrysobalanaceae inferred from Traditional Tongan cures for morning sickness chloroplast, nuclear, and morphological data. Ann and their mutagenic: toxicological evaluations. J Missouri Bot Gard 97: 259-281. Ethnopharmacol 71: 201-209. Zuque ALF, Watanabe ES, Ferreira AMT, Arruda ALA, Resende Paulo SA, Balassiano IT, Silva NH, Castilho RO, UM, Bueno NR, Castilho RO 2004. Avaliação das Kaplan MAC, Cabral MC, Carvalho MGC 2000. atividades antioxidante, antimicrobiana e citotóxica Chrysobalanus icaco L. Extract for antiangiogenic de Couepia grandiflora Benth. (Chrysobalanaceae). potential observation. Internat J Mol Med 5: 667- Rev Bras Farmacogn 14: 129-136. 669. Pittier H 1978. Manual de las plantas usuales de Venezuela. *Correspondence Caracas: Editorial Fundación Eugenio Mendoza, p 579. Karina Perrelli Randau Prance GT 1988. Flora do Estado de Goiás. Goiânia: Ed. da Laboratório de Farmacognosia, Universidade Federal de Universidade Federal de Goiás. Pernambuco Presta GA, Pereira NA 1987. Atividade do abagerú Cidade Universitária, 50740-521 Recife-PE, Brazil (Crysobalanus icaco Lin, Crysobalanaceae) em [email protected] modelos experimentais para o estudo de plantas Tel.: +55 81 3076 4774

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