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Contribuição ao estudo de espécies da família Rubiaceae: gênero amaioua

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Previous issue date: 2014-03-07 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / The Amaioua genus (Rubiaceae) is included in the subfamily Ixoroideae. The
genus comprises 10 species, ranging from Panama to Peru, Venezuela and Brazil, and
four of these species are found in Cerrado (DELPRET et al., 2004b). There are no
records in the literature on the popular use of the Amaioua genus. Amaioua guianensis
Aulb is a shrub up to 3 m or a 10-20 m tree, popularly known as marmelada-brava ou
marmelinho-vermelho. Phytochemical studies of leaves and twigs of this species led to
the isolation of several classes of secondary metabolites, such as coumarins, a
cyclopeptide alkaloid, pentacyclic triterpenes, proanthocyanidins and chlorogenic acids
(OLIVEIRA,2009).
Amaioua intermedia Mart, popularly known as carvoeiro, pau-carvão, cinzeiro,
canela-de-veado, guapeva-forte or marmelada-brava, presents itself as shrubs up to 3 m
or 15 m trees. Until the moment there are no records in the literature about a
phytochemical study of A. intermedia,. As part of our phytochemical research for new
compounds from higher plants, we studied the ethanolic extracts of A. guianensis and A.
intermedia, and evaluated the antioxidant activity of such extracts and fractions
obtained from them. Herein we describe the isolation and structural elucidation of a new
kaurane diterpene (compound 8), a new cyclopeptide alkaloid (compound 19), two new
secologanin iridoid (compounds 24 and 25, and seventeen known compounds: a
cyclopeptide alkaloid (compound 7), five iridoids (compounds 1, 13, 14, 15 and 16), a
ent-kaurane diterpene (compound 22), two dimeric proanthocyanidins (compounds 11
and 12), three pentacyclic triterpenes (compounds 9, 20 and 21), a sugar (compound 10)
and four steroids (compounds 3, 4, 5 and 6).
The antioxidant activity analysis of the raw extracts obtained from fruits, roots,
leaves and twigs of A. guianensis, as well as the raw extracts from the leaves and twigs
of A. Intermedia, showed that they reacted to the DPPH radical, leading to a loss of 50%
in its absorbance, on the following concentrations of 71.87, 7.55, 5.30, 7.48, 46.83 and
57.42 mg/mL. / O gênero Amaioua (Rubiaceae) é posicionado na subfamília Ixoroideae
Ecompreende cerca de 10 espécies encontradas do Panamá até o Peru, Venezuela e
Brasil, sendo que quatro destas espécies encontram-se no bioma Cerrado (DELPRET et
al., 2004b). Não há registro na literatura do uso na medicina popular para as espécies do
gênero.
Amaioua guianensis Aulb é um arbusto de até 3 m ou árvore de 10-20 m de altura
conhecido popularmente como marmelada-brava ou marmelinho-vermelho. O estudo
fitoquímico das folhas e dos galhos dessa espécie levou ao isolamento de diversas
classes de metabólitos secundários tais como: cumarinas, alcalóide ciclopeptídeo,
triterpenos pentacíclicos, proantocianidinas, e ácidos clorogênicos, (OLIVEIRA, 2009).
Amaioua intermedia Mart conhecida popularmente como carvoeiro, pau-carvão,
cinzeiro, canela-de-veado, guapeva-forte ou marmelada-brava, apresenta-se como
arbustos de até 3 m ou árvores de até 15 m de altura. Até o presente momento, não há
relatos na literatura sobre o estudo fitoquímico da espécie A. intermedia.
Como parte de nossa pesquisa fitoquímica em busca de novos metabólitos de
espécies da família Rubiaceae, nós investigamos os extratos etanólicos de A. guianensis
e A. intermedia, bem como a atividade antioxidante desses extratos e das frações obtidas
dos mesmos. No presente estudo descrevemos o isolamento e a elucidação estrutural de
um novo diterpeno kaurano (composto 8), um novo alcalóide ciclopeptídeo (composto
19), dois novos iridóides secologanínicos (compostos 24 e 25), além de outros dezessete
compostos já conhecidos: sendo um alcalóide ciclopeptídeo (composto 7), cinco
iridóides (compostos 1, 13, 14, 15 e 16), um diterpeno ent-kaurano (composto 22), duas
proantocianidinas diméricas (composto 11 e 12), três triterpenos pentacíclicos
(compostos 9, 20 e 21), um açúcar (composto 10), além de quatro esteróides (compostos
3, 4, 5 e 6).
A análise da atividade antioxidante dos extratos brutos dos frutos, raízes, folhas e
galhos da espécie A. guianensis, bem como dos extratos brutos das folhas e galhos da
espécie A. intermedia, mostrou que os mesmos reagiram com o radica DPPH levando a
uma perda de 50% na absorbância do mesmo em concentrações de 71,87; 7,55; 5,30;
7,48; 46,83 e 57,42 μg/mL, respectivamente.

Identiferoai:union.ndltd.org:IBICT/oai:repositorio.bc.ufg.br:tde/3043
Date07 March 2014
CreatorsOliveira, Pollyanna Laurindo
ContributorsOliveira, Cecília Maria Alves, Oliveira, Cecília Maria Alves de, Garcez, Walmir Silva, Foglio, Mary Ann, Lião, Luciano Morais, Sabino, José Ricardo
PublisherUniversidade Federal de Goiás, Programa de Pós-graduação em Química (IQ), UFG, Brasil, Instituto de Química - IQ (RG)
Source SetsIBICT Brazilian ETDs
LanguagePortuguese
Detected LanguagePortuguese
Typeinfo:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis
Formatapplication/pdf
Sourcereponame:Biblioteca Digital de Teses e Dissertações da UFG, instname:Universidade Federal de Goiás, instacron:UFG
Rightshttp://creativecommons.org/licenses/by-nc-nd/4.0/, info:eu-repo/semantics/openAccess
Relation663693921325415158, 600, 600, 600, 600, 7826066743741197278, -8194069717282802154, 2075167498588264571, Brasileiro BF, Passeri LA. Epidemiological analysis of maxillofacial fractures in Brazil: a 5-year prospective study. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 2006; 102: 28-34. Jin Z, Jiang X, Shang L. Analysis of 627 hospitalized maxillofacial-oral injuries in Xi’an, China. Dent Traumatol 2013. Gassner R, Tuli T, Hächl O, Rudisch A, Ulmer H. Craniomaxillofacial trauma: a 10 year review of 9543 cases with 21067 injuries. J Craniomaxillofac Surg 2003; 31:51-61. Kotecha S, Scannell J, Monaghan A, Williams RW. A four year retrospective study of 1062 patients presenting with maxillofacial emergencies at a specialist paediatric hospital. Br J Oral Maxillofac Surg 2008; 293-6. Scariot R, Oliveira IA, Passeri LA, Rebellato NLB, Müller PR. Maxillofacial injuries in a group of Brazilian subjects under 18 years of age. J Appl Oral Sci 2009; 17:195-8. Cavalcanti AL, Bezerra PKM, Oliveira DM, Granville-Garcia AF. Maxillofacial injuries and dental trauma in patients aged 19-80 years, Recife, Brazil. Rev Esp Cir Oral Maxilofac 2010; 32:11-6. Chrcanovic BR, Abreu MHNG, Freire-Maia B, Souza LN. 1,454 mandibular fractures: A 3-year study in a hospital in Belo Horizonte, Brazil. J Craniomaxillofac Surg 2012; 40:116-23. Lee KH, Snape L, Steenberg LJ, Worthington J. Comparison between interpersonal violence and motor vehicle accidents in the etiology of maxillofacial fractures. ANZ J Surg 2007: 77:695- Kostakis G, Stathopoulos P, Dais P, Gkinis G, Igoumenakis D, Mezitis M, Rallis G. An epidemiologic analysis of 1142 maxillofacial fractures and concomitant injuries. Oral Surg Oral Med Oral Pathol Oral Radiol 2012; 114:S69-73. Motamedi MHK. An assessment of maxillofacial fractures: a 5-year study of 237 patients. J Oral Maxillofac Surg 2003; 61:61-4. Chrcanovic BR, Freire-Maia B, Souza LN, Araújo VO, Abreu MH. Facial fractures: a 1-year retrospective study in a hospital in Belo Horizonte. Braz Oral Res 2004; 18:322-8. Subhashraj K, Nandakumar N, Ravindran C. Review of maxillofacial injuries in Chennai, India: a study of 2748 cases. Br J Oral Maxillofac Surg 2007; 45:637-9. van den Bergh B, Karagozoglu KH, Heymans MW, Forouzanfar T. Aetiology and incidence of maxcillofacial trauma in Amsterdam: a retrospective analysis of 579 patients. J Craniomaxillofac Surg 2012; 40:e165-9. Hogg NJ, Stewart TC, Armstrong JE, Girotti MJ. Epidemiology of maxillofacial injuries at trauma hospital in Ontario, Canada between 1992 and 1997. J Trauma 2000; 49: 425:32. Iida S, Kogo M, Sugiura T, Mima T, Matsuya T. Retrospective analysis of 1502 patients with facial fractures. Int J Oral Maxillofac Surg 2001; 30:286-90. Ribeiro MFP, Marcenes W, Croucher R, Sheiham A. The prevalence and causes of maxillofacial fractures in patients attending accident and emergency departments in Recife-Brazil. Int Dent J 2004; 54:47-51. Maliska MCS, Júnior SML, Gil JN. Analysis of 185 maxillofacial fractures in the state of Santa Catarina, Brazil. Braz Oral Res 2009; 23:268-74. Chrcanovic BR, Abreu MHNG, Freire-Maia B, Souza LN. Facial fractures in children and adolescents: a retrospective study of 3 years in a hospital in Belo Horizonte, Brazil. Dent Traumatol 2010; 26:262-70. Leles JLR, Santos ÊJ, Jorge FD, Silva ET, Leles CR. Risk factors for maxillofacial injuries in a Brazilian emergency hospital sample. J Appl Oral Sci 2010; 18:23-9. Pereira CM, Filho MS, Carneiro DS, Arcanjo RC, Andrade LA, Araújo MGB. Epidemiology of maxillofacial injuries at a regional hospital in Goiânia, Brazil, between 2008 and 2010. RSBO 2011; 8:381-5. IBGE [Brazilian Institute of Geography and Statistics]. Demographic Census; 2013. World Health Organization. Standardization of reporting of dental disease and condition. Technical Report Series 1962; n.242, 23p. Roccia F, Bianchi F, Zavattero E, Tanteri G, Ramieri. Characteristics of maxillofacial trauma in females: a retrospective analysis of 367 patients. J Craniomaxillofac Surg 2010; 38:314-9. Lin S, Levin L, Goldman S, Peled M. Dento-alveolar and maxillofacial injuries – a retrospective study from a level 1 trauma center in Israel. Dent Traumatol 2007; 23:155-7. Al Ahmed HEA, Jaber MA, Fanas SHA, Karas M. The pattern of maxillofacial fractures in Sharjah, United Arab Emirates: A review of 230 cases. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 2004; 98:166-70. Yokoyama T, Motozawa Y, Sasaki T, Hitosugi M. A retrospective analysis of oral and maxillofacial injuries in motor vehicle accidents. J Oral Maxillofac Surg 2006; 64:1731-35. Anderson PJ. Fractures of the facial skeleton in children. Injury 1995; 26:47-50. Arosarena OA, Fritsch TA, Hsueh Y, Aynehchi B, Haug R. Maxillofacial injuries and violence against women. Arch Facial Plast Surg 2009; 11:48-52. Oji C. Jaw fractures in Enugu, Nigeria, 1985-95. Br J Oral Maxillofac Surg 1999; 37: 106-9. Almeida-Filho N, Rouquayrol MZ. Introdução à epidemiologia. 3 ed. Rio de Janeiro: Medsi, 2002. Freire MCM, Pattusi MP. Tipos de estudo. In: Estrela C. Metodologia Científica. 2 ed. São Paulo: Artes Médicas, 2005. p.185-209. Antunes JLF, Peres MA. Fundamentos de odontologia, epidemiologia da saúde bucal. Rio de Janeiro: Guanabara Koogan, 2006. Hulley SB, Cummings SR. 1988. Designing Clinical Research. Baltimore (MD, Williams & Wilkins). AGUIAR, LA. A.; PORTO, R. S.; LAHLOU, S.; ZIN, W. A.; LEAL-CARDOSO, J. H. Antispasmodic effects of a new kaurene diterpene isolated from Croton argyrophylloides on rat airway smooth muscle. Journal of Pharmacy and Pharmacology. v. 64, p. 1155-1164, 2012. ALCÂNTARA, A. F. de C.; SILVA, M. C. FRANÇA, R. C.; VELOSO, D. P.; da COSTA, H. N. R.; SANTOS, M. C. Constituintes químicos e atividade antiedematogênica de Peltodon radicans (LAMIACEAE). Química Nova. v. 31, p. 744-750, 2008. AMBROSIO, S. R.; TIRAPELLI, C. R.; da COSTA, F. B.; de OLIVEIRA, A. M. Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility. Life Sciences, v. 79, pp. 925-933, 2006. ARGÁEZ, R. B.; BAIZABÁL, L. M.; PAT, F. M.; RODRÍGUEZ, L. M. P. A new ent-kaurane from the root extract of Chicocca alba. Canadian Journal of Chemistry, v. 75, pp. 801-804, 1997. ASLAN, I.; KILIC, T.; GOREN, A.C.; TOPCU, G. Toxicity of acetone extract of Sideritis trojana and 7-epicandicandiol, 7-epicandicandiol diacetate and 18-acetylsideroxol against stored pests Acanthoscelides obtectus(Say), Sitophilus granarius (L.) and Ephestia kuehniella (Zell.) Industrial Crops and Products v. 23, pp. 171-176, 2006. BAN, N. K.; GIANG, V. H.; LINH, T. M.; LIEN, L. Q.; NGOC, N. T.; THAO, D. T.; NAM, N. H.; CUONG, N. X.; KIEM, P. V.; MINH, C. V. Two new 11-noriridoids from the aerial parts of Morinda umbellata. Phaytochemistry Letters, v. 6, p. 267-269, 2013. BENABADJI, S. H.; WEN, R.; ZHENG, J-B.; DONG, X-C.; YUAN S-G. Anticarcinogenic and antioxidant activity of diindolylmethane derivatives. Acta Pharmacol Sin, v. 25, p. 666-671, 2004. BENEVIDES, P. J. C.; YOUNG, M. C. M.; BOLZANI, V. S. Biological Activities of Constituents from Psychotria spectabilis. Pharmaceutical Biology, v. 42, pp. 565-569, 2004. BENTLEY, K. W. β-Phenylethylamines and the isoquinoline alkaloids. Nat. Prod. Rep. v. 23, p. 444-463, 2006. BHATTACHARYYA, J.; BARROS, C. B. Triterpenoids of Cnidosculus urens. Phytochemistry. v. 25, p.274–276, 1986. BLOCK, L.C.; SANTOS, A.R.S.; SOUZA, M.M.; SCHEIDT, C.; YUNES, R.A.; SANTOS, M.A.; MONACHE, F.D.; FILHO, V.C. Chemical and pharmacological examination of antinociceptive constituents of Wedelia paludosa. Journal of Ethnopharmacology, v. 61, pp. 85-89, 1998. BOAVENTURA, M. A. D.; PEREIRA, R. G.; FREITAS, L. B. O.; REIS, L. A.; VIEIRA, H. S. Preparation and phytotoxicity of novel kaurane diterpene amides with potential use as herbicides. Journal of Agricultural Food Chemistry, v. 56, n. 9, pp. 2985-2988, 2008. BOLZANI, V. S.; TREVISAN, L. M. V.; YOUNG, M. C. M. Rev. Latinoamer. Quim., v. 23, n. 1, p. 20-21, 1992. BOLZANI, V. D. S.; IZUMISAWA, C. M.; YOUNG, M. C. M.; TREVISAN, L. M. V.; KINGSTON, D. G. I.; GUNATILAKA, A. L. Iridoids from Tocoyena formosa. Phytochemistry, v. 46, p. 305, 1997. BOLZANI et. al. Ésteres triterpênicos de Himatanthus sucuuba (Spruce) Woodson. Química Nova, v. 21, p. 702-704, 1998. BOLZANI, V. da S., YOUNG, M. C. M., FURLAN, M., CAVALHEIRO, A. J., ARAÚJO, A. R., SILVA, D. H. S., LOPES, M. N. Recent Res. Devel. Phytochemistry. v. 5, p. 19, 2001. BREMER, B.; ANDREASEN, K.; OLSSON, D. Subfamilial and tribal relationships in the Rubiaceae based on rbcL sequence data. Annals of the Missouri Botanic Garden, v. 82, p. 383- 397, 1995. BRESCIANI, L.F.V.; CECHINEL-FILHO, V.; YUNES, R.A. Comparative study of different parts of Wedelia paludosa by gas chromatography. Natural Product Letters, v. 14, pp. 247-254, 2000. BRESCIANI, L.F.V.; YUNES, R.A.; BURGER, C.; OLIVEIRA, L.E.; BÓF, K.L.; CECHINELFILHO, V. Z. Seasonal variation of kaurenoic acid, a hypoglycemic diterpene present in Wedelia paludosa (Acmela brasiliensis) (Asteraceae). Zeitschrift fur Naturforschung - Section C Journal of Biosciences, v. 59, pp. 229-232, 2004. CAVALCANTI, B.C.; COSTA-LOTUFO, L.V.; MORAES, M.O.; BURBANO, R.R.; SILVEIRA, E.R.; CUNHA, K.M.A.; RAO, V.S.N.; MOURA, D.J.; ROSA, R.M.; HENRIQUES, J.A.P.; PESSOA, C. Genotoxicity evaluation of kaurenoic acid, a bioactive diterpenoid present in Copaiba oil. Food and Chemical Toxicology, v. 44, pp. 388-392, 2006. CHAUDHURI, R. K.; WINKLER, T.; STICHER, O. 13C NMR spectroscopy of naturally occurring iridoid glucosides and their acylated derivatives. Tetrahedron, v. 36, p. 2317-2326, 1980. CHEENPRACHA, S.; YODSAOUE, O.; KARALAI, C.; PONGLIMANONT, C.;SUBHADHIRASAKU, S.; TEWTRAKUL, S.; KANJANA-OPAS, A. Potential antiallergic ent-kaurene diterpenes from the bark of Suregada multiflora. Phytochemistry, v. 67, pp. 2630-2634, 2006. CHEN, K.; SHI, Q.; FUJIOKA, T.; NAKANO, T.; HU, C. –Q.; JIN, J. –Q.; KILKUSKIE, R. E.; LEE, K. –H. Anti-AIDS Agents-XIX. Neotripterifordin, a Novel Anti-HIV Principle from Tripterygium wilfordii: Isolation and Structural Elucidation. Bioorganic & Medicinal Chemistry, v. 3, pp. 1345-1348, 1995. COSTA-LOTUFO, L.V.; CUNHA, G.M.A.; FARIAS, P.A.M.; VIANA, G.S.B.; CUNHA, K.M.A.; PESSOA, C.; MORAES, M.O.; SILVEIRA, E.R.; GRAMOSA, N.V.; RAO, V.S.N. The cytotoxic and embryotoxic effects of kaurenoic acid, a diterpene isolated from Copaifera langsdorffii oleo-resin. Toxicon, v. 40, pp. 1231-1234, 2002. CUNHA, K.M.A.; PAIVA, L.A.; SANTOS, F.A.; GRAMOSA, N.V.; SILVEIRA, E.R.; RAO, V.S. Smooth Muscle Relaxant Effect of Kaurenoic Acid, a Diterpene from Copaifera langsdorffii on Rat Uterus in vitro. Phytotherapy Research, v. 17, pp. 320-324, 2003. DELPRETE, P.G. Rubiaceae. In: SMITH, N.P. et al. Flowering Plant Families of the American Tropics. Ed. Princeton University Press/ New York Botanical Garden Press. p. 328-333, 2004a. DELPRETE, P. G., SMITH, L. B., KLEIN, R. M. Rubiáceaes, Vol. I – Gêneros de A-G: 1. Alseis até 19. Galium. In: A. Reis. (Ed), Flora Ilustrada Catarinense. Itajaí, SC. 344 p, 2004b. DELPRETE, P.G. Sinopse dos gêneros de Rubiaceae do Brasil. 49 Congresso Nacional de Botânica (26 Julho - 1 Agosto), Resumos, Salvador, Bahia, p. 85-86, 1998. DEVAPPA. R. K.; MAKKAR, H. P. S.; BECKER, K. Jatropha Diterpenes: a Review. Journal of the American Oil Chemists’ Society, v. 88, pp. 301-322, 2011. DEWICK, P. M. Medicinal Natural Products. A Biosynthetic Approach. 2. ed., Chichester: John Wiely & Sons Ltd, 2002. DIXON, R. A.; XIE, D-Y., SHARMA, S. B. Proanthocyanidins –a final frontier in flavonoid research? New Phytol., v. 165, p. 9-28, 2005. DREWES, S. E.; HORN, M. M.; MUNRO, O. Q.; RAMESAR, N.; OCHSE, M.; BRINGMANN, G.; PETERS, K. PETERS E. V. Stereostructure, conformation and reactivity of - and -gardiol fron Burchellia bubalina. Phytochemistry. v. 50, p. 387-394, 1999. DRÖGE, W. Free Radicals in the Physiological Control of Cell Function. Physiol Ver. v. 82, 47–95, 2002. DUAN, H.; TAKAISHI, Y.; MOMOTA, H.; OHMOTO, Y.; TAKI, T.; JIA, Y.; LI, Y. Immunosuppressive Diterpenoids from Tripterygium wilfordii . Journal of Natural Products, v. 62, pp. 1522-1525, 1999. DUAN, H.; TAKAISHI, Y.; MOMOTA, H.; OHMOTO, Y.; TAKI, T,; TORI, S. T.; JIA, Y.; LI, D. Immunosuppressive terpenoids from extracts of Tripterygium wilfordii. Tetrahedron , v. 57, pp. 8413-8424, 2001. DUMAS, J. B. Annales of Chimie at de Physique, v. 5, n. 3, 1874. In: RODRIGUES, J. A. R. & MORAN, P. J. S. Reduções enantiosseletivas de cetonas utilizando-se fermento de pão. Química Nova, v. 24, n. 6, São Paulo, 2001. EL-SEEDI, H. R.; GOHIL, S.; PERERA, P.; TORSSELL, K. B. G.; BOHLIN, L. Cyclopeptide alkaloids from Heisteria nitida. Phytochemistry. v. 52, p. 1739-1744, 1999 ESQUIVEL, P.; JIMÉNEZ, V. M. Functional properties of coffee and coffee by-products. Food Research International, v. 46, pp. 488-495, 2012. FARID, H. A. R.; KUNERT, O.; HASLINGER, E.; SEGER, C. Isolation and structure elucidation of iridóides and coumarin derivatives from Xeromphis nilotica (Rubiaceae). Monatshefte für Chemie. v. 133, p. 1453-1458, 2002. GÁLVEZ, M.; CORDERO, C. M.; AYUSO, M. J. Pharmacological activities of iridoids biosynthesized by route II. Studies in Natural Products Chemistry. v. 32, pag. 365-394, 2005. GIACOMELLI, S. R.; MALDANER, G.; GONZAGA, W. A.; GARCIA, C. M.; SILVA, U. F.; DALCOL, I. I.; MOREL, A. F. Cyclic peptide alkaloids from the bark of Discaria americana. Phytochemistry. v. 65, p. 933-937, 2004. GHISALBERTI, E. L. The biological activity of naturally occurring kaurane diterpenes. Fitoterapia, v. 68, pp. 303-325, 1997. GHISALBERTI, E.L.; PENNACCHIO, M.; ALEXANDER, E. Survey of Secondary Plant Metabolites with Cardiovascular Activity. Pharmaceutical Biology, v. 36, pp. 237-279, 1998. GONÇALVES, C.; DINIS, T.; BATISTA, M. T. Antioxidant properties of proanthocyanidins of Uncaria tomentosa bark decoction: a mechanism for anti-inflammatory activity. Phytochemistry. v. 66, p. 89-98, 2005. GOURNELIS, D. C.; LASKARIS, G. G.; VERPOORTE, R. Cyclopeptide alkaloids. Natural Product Reports. v. 14, p.75-82, 1997. HANSON, J. R. Diterpenoids. Natural Products Reports, v. 21, pp. 785-793, 2004. HANSON, J. R. Diterpenoids. Natural Products Reports, v. 26, pp. 1156-1171, 2009. HASAN, C. M.; HEALEY, T. M.; WATERMAN P. G. Kolavane and kaurane diterpenos from the stem bark of Xylopia aethiopica*. Phytochemistry, v. 21, pp. 1365-1368, 1982. HE, D. –H.; MATSUNAMI, K.; OTSUKA, H.; SHINZATO, T.; ARAMOTO, M.; BANDO, M.; TAKEDA, Y. Trcalysiosides H-O: Ent-kaurane glucosides from the leaves of Tricalysia dubia. Phytochemistry, v. 66, pp. 2857-2864, 2005. HE, D. –H.; MATSUNAMI, K.; OTSUKA, H.; SHINZATO, T.; ARAMOTO, M.; BANDO, M.; TAKEDA, Y. Tricalysiolide G and tricalysiols A and B: rearranged ent-kaurane-type and entkaurane- type diterpenoids from the leaves of Tricalysia dubia (Lindl.) Ohwi. Journal Natural Products, v. 61, pp. 46-50, 2007. HEDDEN, P. The oxidases of gibberelin biosynthesis: their function and mechanism. Physiologia plantarum, v. 101, pp. 709-719, 1997. HEITZMAN, M. E.; NETO, C. C.; WINIARZ, E.; VAISBERG, A. J.; HAMMOND, G. B. Rev. Ethnobotany, phytochemistry and pharmacology of Uncaria (Rubiaceae). Phytochemistry. v. 66, p. 5-29, 2005. HENRIQUES, A. T. ; LOPES, S. O.; PARANHOS, J. T.; GREGIANINI, T. S.; POSER, G. L. V.; FETT-NETO, A. G.; SCHRIPSEMA, J. N. β-D-Glucopyrnosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa. Phytochemisty. v. 65, p. 449- 454, 2004. HIROSE, M.; HAGIWARA, A.; HASUI,; INOVE, K.; ITO, N. Combinated effects of BHA and other antioxidants in induction of forestomach lesions in rats. Cancer Lett., Shannon, v.30, n.2, p. 169-174, 1986. ITO, N.; FUKUSHIMA, S.; HAGIWARA, A.; SHIBATA, M.; OGISO, T. Carcinogenicity of butylated hydroxyanisole in F 344 rats. J. Natl. Cancer Inst., Cary, v.70, p. 343- 352, 1983. JAENSCH, M.; JAKUPOVIC, J.; SANCHEZ, H.; DOMINGUEZ, X. A. Diterpenes from Hoffamannia strigillosa. Phytochemistry, v. 29, pp. 3587-3590, 1990. JENSEN, S. R. Iridoids in Rothmannia globosa Phytochemistry, v. 22, p. 1761, 1983. JOULLIÉ, M. M.; RICHARD, D. J. Cyclopeptide alkaloids : chemistry and biology. Chem. Commun. p. 2011-2015. 2004. JUNGES, M. J.; FERNANDES, J. B.; VIEIRA, P. C.; FERNANDES, M. F. G. S.; FILHO, E. R.; FRUHAUF, M.; BARAÑANO, A. G. Triterpenos Ursânicos e Oleanânicos Isolados do Caule de Eugenia Florida DC. Revista de Pesquisa e Pós-Graduação, Erechim, RS, Brasil, v. 01, p. 13-30, 2000. KAMIYA, K.; WATANABE, C.; ENDANG, H.; UMAR, M.; SATAKE, T. Studies on the Constituents of Bark of Parameria laevigata MOLDENKE. Chem. Pharm. Bull., v 49 (5), 551- 557, May 2001. KIM, S.; NA, M.K.; OH, H.; JANG, J.P.; SOHN, C.B.; KIM, B.Y.; OH, W.K.; AHN, J.S. PTP1B inhibitory activity of kaurane diterpenes isolated from Siegesbeckia glabrescens. Journal of Enzyme Inhibition and Medicinal Chemistry, v. 21, pp. 379-383, 2006. KITAJIMA, M.; OHARA, S.; KOGURE, N.; SANTIARWORN, H. T. B-Carboline-type indole alkaloid glycosides from Ophiorrhiza trichocarpon. Tetrahedron, v. 69, p. 9451-9456, 2013. KO, H. H.; CHANG, W. L.; LU, T. M. Antityrosinase and antioxidant effects of ent-kaurane diterpenos from leaves of Broussonetia papyrifera. Journal of Natural Products, v. 71, n. 11, pp. 1930-1933, 2008. KOIKE, C.; DORDELL, G. A.; FARNSWORTH, N. R.; FREER, A. A.; GILMORE, C. J.; SIM, G. A. New cytotoxic diterpenos from Rondeletia panamensis (Rubiaceae). Tetrahedron, v. 36, pp. 1167-1172, 1980. KOLEVA, II.; van BEEK, T.; LINSSEN, J. P.; de GROOT, A.; EVSTATIEVA, L. N. Screening of plant extracts for antioxidant activity: a comparative study on three testing methods. Phytochemistry. Anal 13: 8-17, 2002. KOUAME, F. P. B.; BEDI, G.; KOFFI, A. M.; CHALCHAT, J. C.; GUESSAN, T. Y. N. Volatiles constituents from leaves of Morinda morindoïdes (Rubiaceae): A medicinal plant from the Ivory Coast. The Open Natural Products Journal, v. 3, pp. 6-9, 2010. LIN, L.; GAO, Q.; CUI, C.; ZHAO, H.; FU, L.; CHEN, L.; YANG, B.; LUO, W.; ZHAO, M. Isolation and identification of ent-kaurane-type diterpenoids from Rabdosia serra (MAXIM.) HARA leaf and their inhibitory activities against HepG-2, MCF-7, and HL-60 cell lines. Food Chemistry, v. 131, pp 1009-1014, 2012. LING, S-K.; LOMORITA, A.; TANAKA, T.; FUJIOKA, T.; MIHASHI, K.; KOUNO, I. Iridoids and Anthraquinones from the Malaysian Medicinal Plant, Saprosma scortechinii (Rubiaceae). Chem. Pharm. Bull. v. 50, n. 8, p. 1035-1040, 2002. LIU, R.; ZHANG, P.; GAN, T.; COOK, J. M. Regiospecific Bromination of 3-Methylindoles with NBS and Its Application to the Concise Synthesis of Optically Active Unusual Tryptophans Present in Marine Cyclic Peptides. J. Org. Chem. v. 62, p. 7447-7456, 1997. LIU, J.J.; HUANG, R.W.; LIN, D.J.; PENG, J.; ZHANG, M.H.; PAN, X.L.; HOU, M.; WU, X.Y.; LIN, Q.; CHEN, F. Ponicidin, an Ent-Kaurane Diterpenoid Derived from a Constituent of the Herbal Supplement PC-SPES, Rabdosia rubescens, Induces Apoptosis by Activation of Caspase-3 and Mitochondrial Events in Lung Cancer Cells In Vitro Read More. Cancer Investigation, v. 24, pp. 136-148, 2006. LOPES, S.; POSER, G. L.; KERBER, V. A.; FARIAS, F. M.; KONRATH, E. L.; MORENO, P.; SOBRAL, M. E.; ZUANAZZI, J. A. S. e HENRIQUES, A. T. Taxonomic significance of alkaloids and iridoid glucosides in the tribe Psychotrieae (Rubiaceae). Biochem. Syst. Ecol., v. 32, p. 1187-1195, 2004. LOPES, M. N.; SILVA, V. C.; FARIA, A. O.; BOLZANI, V. S.. A new ent-kaurane diterpene from stems of Alibertia macrophylla K. schum (Rubiaceae). Helvetica Chimica Acta, v. 90, pp. 1781-1785, 2007. LUCIANO, J. H. S.; LIMA, M. A. S.; SOUZA, E. B.; SILVEIRA, E. R. Chemical constituents of Alibertia myrciifolia Spruce ex K. Schum. Biochemical systematics and ecology. v. 32, p. 1227-1229, 2004. LUCIANO, J. H. S.; LIMA, M. A. S.; SIQUEIRA, E. R. Antifungal iridoids, Triterpenes and Phenol compounds from Alibertia myrciifolia Sprunge ex. Schum. Química Nova. v. 33. n. 2, 292-294, 2010. MAHATO, S. B.; KUNDU, A. P. 13C NMR Spectra of pentacyclic triterpenoids—a compilation and some salient features. Phytochemistry, v 37, p. 1517-1575, 1994. MARTIN, G. E., SANDUJA, R., ALAM, M. Two-Dimensional NMR Studies of Marine Natural Products. Utilization of Two-Dimensional Proton Double Quantum Coherence NMR Spectroscopy in Natural Products Structure Elucidation-Determination of Long-Range Couplings in Plumericin. J. Org. Chem. v. 50, 1985. MENEZES, A. S.; MOSTARDEIRO, M. A.; ZANATTA, N.; MOREL, A. F. Scutianine-J, a cyclopeptidic alkaloid isolated from Scutia buxifolia. Phytochemistry. v. 38, p. 783-786, 1995. MOREL, A. F.; ARAUJO, C. A.; SILVA, U. F.; HOELZEL, S. C. S. M.; ZÁCHIA, R.; BASTOS, N. R. Antibacterial cyclopeptide alkaloids from the bark of Condalia buxifolia. Phytochemistry. v. 61, p. 561-566, 2002. MOREL, A. F.; MALDANER, G.; ILHA, V.; MISSAU, F.; SILVA, U. F.; DALCOL, I. I. Cyclopeptide alkaloids from Scutia buxifolia Reiss and their antimicrobial activity. Phytochemistry. v. 66, p. 2571-2576, 2005. MORRIS, B.D.; FOSTER, S.P.; GRUGEL, S.R.; CHARLET, L.D. Isolation of the diterpenoids, ent-karan- -ol and ent-atisan- -ol, from sunflowers, as oviposition stimulants for the banded sunflower moth, Cochylis hospes. Journal of Chemical Ecology, v. 31, pp. 89-102, 2005. MOURA, V. M.; SANTOS, D. P.; SANTIN, S. M. O. Constituintes químicos de Galianthe brasiliensis (Rubiaceae). Química Nova. v. 29, n. 3, p. 452-455, 2006. NAGASHIMA, F.; TANAKA, H.; TAKAOKA, S.; ASAKAWA, Y. Ent-kaurane-type diterpenoids from the liverwort Jungermannia exsertifolia ssp. Cordifolia. Phytochemistry, v. 41, pp. 1129-1141, 1996. NAGASHIMA, F.; TANAKA, H.; ASAKAWA, Y. Ent-kaurane-type diterpenoids from the liverwort Jungermannia rotundata. Phytochemistry, v. 44, pp. 653-657, 1997. NASCIMENTO, C. A. Estudo fitoquímico e avaliação da atividade antibacteriana de Palicourea coureacea (Rubiaceae). Goiânia: UFG, 2005. Dissertação (Mestrado em Química), Instituto de Química, Universidade Federal de Goiás, 2005. NASCIMENTO, C. J.; VIOLANTE, I. M. P.; GARCEZ, W. S.; POTT, A.; GARCEZ, F. R. Biologically active abietane and ent-kaurane diterpenoids and other constituents from Erythroxylum suberosum. Phytochemistry Letters, v. 5, pp. 401-406, 2012. NISHIMURA, K.; HITOTSUYANAGI, Y.; SUGETA, N.; SAKAKURA, K-I.; FUKITA, K.; FUKAYA, H.; AOYAGI, Y.; HASUDA, T.; KINOSHITA, T.; TAKEYA, K.; HE, D.-H.; OTSUKA, H.; TAKEDA, Y. Tricalysiamides A-F, new rearranged ent-kaurane diterpenos from Tricalysia dúbia. Tetrahedron, v. 62, pp. 1512-1519, 2006. NISHIMURA, K.; HITOTSUYANAGI, Y.; SUGETA, N.; FUKAYA, H.; AOYAGI, Y.; HASUDA, T.; KINOSHITA, T.; TAKEYA, K. Tricalysiamides A-D, Diterpenoid alkaloids from Tricalysia dúbia. Journal of Natural Products, v. 70, pp. 758-762, 2007. OLIVEIRA, P. L. Contribuição ao estudo de espécies da família Rubiaceae: Fitoquímica da espécie Amaioua guianensis Aulb. Goiânia: UFG, 2009. Dissertação (Mestrado em Química), Instituto de Química, Universidade Federal de Goiás, 2009. OLIVEIRA, P. R. N. et al. Saponinas triterpênicas das raízes de Guettarda pohliana Müll. Arg. (Rubiaceae). Química Nova v. 31, n. 4, p. 755-758, 2008. OTSUKA, H.; SHITAMOTO, J.; HE, D.-H.; MATSUNAMI, K.; SHINZATO, T.; ARAMOTO, M.; TAKEDA, Y.; KANCHANAPOOM, T. Tricalysiosides P-U: Ent-kaurane glucosides and a labdane glucoside from leaves of Tricalysia dubia Ohwi. Chemical and Pharmaceutical Bulletin, v. 55, pp. 1600-1605, 2007. PHUONG, N. T.; LEE, K. A.; JEONG, S. J.; FU, C. X.; CHOI, J. K.; KIM, Y. H. KANG, J.S. Capillary electrophoretic method for the determination of diterpenoid isomers in Acanthopanax species. Journal of Pharmaceutical and Biomedical Analysis, v. 40, pp. 56-61, 2006. PINTO, A.C.; PINCHIN, R.; PRADO, S.K. Three ent-kaurene diterpenosfrom Vellozia caputardeae. Phytochemistry, v. 22, pp. 2017- 2019, 1983 RAVEN, J. A.; BEARDALL, J.; CHUDEK, J. A.; SCRIMGEOUR, C. M.; CLAYTON, M. N.; MINROY, S. G. Altritol synthesis by Notheia anomala. Phytochemistry. v. 58, p. 389-394, 2001. REYNOLDS, W. F.; LOUGH, A. J.; SAWYER, J. F.; ENRIQUEZ, R. G.; ORTIZ, B.; WALLS, F. Structure of (4α)-kaura-9(11),16-dien-18-oic acid (grandiflorenic acid), an active ingredient of the Mexican medicinal plant zoapatle. Acta Crystallographica Sect. C-47, pp. 973-977, 1991. ROESLER, R.; MALTA, L. G.; CARRASCO, L. C.; PASTORE, G. Evaluation of the Antioxidant Properties of the Brazilian Cerrado Fruit Annona crassiflora (Araticum). Journal of Food Science. v. 71, n. 2, 102-107, 2006. ROOS, B.; WEG, G. V.; URGERT, R.; BOVENKAMP, P. V.; CHARRIER, A.; KATAN, M. B. Levels of cafestol, kahweol, and related diterpenoids in Wild Species of the Coffee Plant Coffea. Journal Agricutural Food Chemistry, v. 45, pp. 3065-3069, 1997. ROSA, E. A.; SILVA, C. C.; TANAKA, C. M. A.; OLIVEIRA, C. M. A.; KATO, L.; FERREIRA, H. D. Antraquinona de Palicourea rígida (Rubiaceae). 29a Reunião Anual da Sociedade Brasileira de Química – SBQ. Águas de Lindóia, SP. 2006. PN-025. ROSSING, D.; KAHL, R.; HILDEBRANDT, A. G. Effect of synthetic antioxidants on hydrogen peroxide formation, oxyferro cytocrome P450 concentration and oxygen consumption in liver microssomes. Toxicology. Amsterdam, v. 34, n.1, p. 67-77, 1985. ROVA, J. H. E.; DELPRETE, P. G.; ANDERSSON, L.; ALBERT, V. A. A trnL-F cpDNA sequence study of the Condamineeae-Rondeletieae-Sipaneeae complex with implications on the phylogeny of the Rubiaceae. American Journal of Botany. v. 89, p. 145-159, 2002. RUIZ, Y.; RODRIGUES, J.; ARVELO, F.; USUBILLAGA, AL; MONSALVE, M.; DIEZ, N.; GALINDO-CASTRO, I. Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-em-19- oic acid, a derivative of grandiflorolic acid from Espeletia schultizii. Phytochemistry, v. 69, n. 2, pp. 432-438, 2008. SANTIN, S. M. O.; ARAUJO, F. C. V.; MARQUES, F. G.; SILVA, C. C. Terpenos isolads de Coussarea platyphylla Müll. Arg. (Rubiaceae). Química Nova, v. 32, pp. 1760-1763, 2009. SANTOS, R. P. et al. Chemical constituents of Cordial piauhiensis- Boraginaceae. J. Braz. Chem. Soc. v 16, n. 3B, p. 662-665, 2005. SHITAMOTO, J.; SUGIMOTO, S.; MATSUNAMI, K.; OTSUKA, H.; SHINZATO, T.; TAKEDA, Y. Tricalysionoside A, a Megastigmane Gentiobioside, Sulfatricalysines A-F, and Tricalysiosides X-Z, ent-kaurane glucosides, from the leaves of Tricalysia dubia. Chemical and Pharmaceutical Bulletin, v. 59, pp. 72-77, 2011. SIERRA, M. G.; MASCARETTI, O. A.; DIAZ, F. J.; RUVEDA, E. A.; CHANG, C.; HAGAMAN, E.W.; WENKERT, E. J. Chem. Soc., Chem. Commun. p. 915, 1972. SILVA, F. M.; KATO, L.; OLIVEIRA, C. M. A.; SILVA, C. C.; TANAKA, C. M. A.; SOARES, P. R. O.; GUILLO, L. A. Vallesiachotamina e atividade citotóxica de Palicourea rigida Kunth. 29a Reunião Anual da Sociedade Brasileira de Química – SBQ Águas de Lindóia, SP. 2006. QB-050. SILVA, V. C.; SILVA, B. G. H.; BOLZANI, V. S.; LOPES, M. N. Isolation of lignans glycosides from Alibertia sensilis (Vell) k. Schum. (Rubiaceae) by preparative high-performance liquid chromatography. Ecética Química. v. 31, p. 55-58, 2006. SILVA, V. C.; FARIA, A. O.; BOLZANI, V. S.; LOPES, M. N. Diterpeno, derivados fenólicos e iridóides glicosilados isolados dos caules de Alibertia macrophylla. 30ª Reunião Anual da Sociedade Brasileira de Química-SBQ. Águas de Lindóia, SP. 2007. PN-013. SMANSKI, M. J.; PETERSON, R. M.; HUANG, S. -X.; SHEN, B. Bacterial diterpeno synthases: new opportunities for mechanistic enzymology and engineered biosynthesis. Chemical Biology, v. 16, p. 132-141, 2012. SOMOVA, L. I.; SHODE, F. O.; MOODLEY, K.; GOVENDER, Y. J. Cardiovascular and diuretic activity of kaurene derivatives of Xylopia aethiopica and Alepidea amatymbica. Journal of Ethnopharmacology,v. 77, pp. 165-174, 2001. STADEN, J. V.; AREMU, A. O.; AMOO, S. O.; NADHLALA, A. R.; FINNIE, J. F. Antioxidant activity, acetylcholinesterase inhibition, iridoid content and mutagenic evaluation of Leucosidea sericea. Food and Chemical Toxicology. v. 49, 1122-1128, 2011. STEFANELLO, M. E. A.; SALVADOR, M. J.; ITO, I. Y.; MACARI, P. A. T. Avaliação da atividade antimicrobiana e citotóxica de extratos de Gochnatia polymorpha ssp. Floccosa. Revista Brasileira de Farmacognosia, v. 16, n. 4, pp. 525-530, 2006. STEPHENS, P. J.; PAN, J. J.; DEVLIN, F. J.; CHEESEMAN J.R. Determination of the Absolute Configurations of Natural Products Using TDDFT Optical Rotation Calculations: The Iridoid Oruwacin. Journal of Natural Products. v.71, p.285–288, 2008. SUGAWARA F.; ISHIMOTO, M.; LE-VAN, N.; KOSHINO, H.; UZAWA, J.; YOSHIDA, S.; KITAMURA, K. Insecticidal peptide from mungbean: aresistant factor against infestation with azuki bean weevil. J Agric Food Chem. v. 44, p. 3360-3364, 1996. TADESMIR, D.; GÜNER, N. D.; PEROZZO, R; BRUN, R.; DÖNMEZ, A. A.; ÇALIS, I.; RÜEDI, P. Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots. Phytochemistry.. v. 66, p. 355-362, 2005. TAKAGI, S.; ISHIGURO, K.; YAMAKI, M. Studies on Iridoid-Related Compounds, II. The Structure and Antimicrobial Activity of Aglucones of Galioside and Gardenoside. Jounal of Natural Products. v. 46, n 4. p. 532-536, 1983. TAKAHASHI, J. A.; VIEIRA, H. S.; SILVA, E. A.; BOAVENTURA, M. A. D.; OLIVEIRA, A. B.; CHIARI, E. Preparation and activity of diterpenoids against trypomastigotes of Typanosoma cruzi. Revista Brasileira de Farmacognosia, v. 12, p. 118-120, 2002. TAKETA, A. T. C. et al. Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté). J. Braz. Chem. Soc. v. 15, n. 2, p. 205-211, 2004. TAMAKI, N.; MATSUNAMI, K.; OTSUKA, H.; SHINZATO, T.; ARAMOTO, M.; TAKEDA, Y. Rearranged ent-kauranes from the stems of Tricalysia dubia and their biological activities. Journal of Natural Medicines, v. 62, p. 314-320, 2008. TAN, N. H.; ZHOU, J. Plant Cyclopeptides. Chem.Rev. v. 106, p. 840-895, 2006. TANAKA, N.; OOBA, N.; DUAN, H.; TAKAISHI, Y.; NAKANISHI, Y.; BASTOW, K.; LEE, K. H. Kaurane and abietane diterpenoids from Tripterygium doianum (Celastraceae). Phytochemistry, v. 65, p. 2071-2076, 2004. TIRAPELLI, C.R.; AMBROSIO, S.R.; COUTINHO, S.T.; DE OLIVEIRA, D.C.R.; DA COSTA, F.B.; DE OLIVEIRA, A.M. Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid. Journal of Pharmacy and Pharmacology, v. 57, p. 997-1004, 2005. TORRENEGRA, R.; GOMEZ, D. L.; TELLEZ, A. N. Gibberelic activity of diterpenes derivatives of kaurenes isolated from Espeletiopsis santanderensis Cuatr. Actualidades Biologicas, v. 23, n. 75, p. 19-22, 2001. TOTTÉ, N.; CHARON, L.; ROHMER, M.; COMPERNOLLE, F.; BABOEUF, I.; GEUNS, J. M. C. Byosynthesis of the diterpenoid steviol, an ent-kaurene derivative from Stevia rebaudiana Bertoni, via the methylerytrhritol phosphate pathway. Tetrahedron Letters, n. 41, p. 6407- 6410, 2000. TUNDIS, R.; LOIZZO, M. R.; MENICHINI, F.; STATTI, G. A.; MENICHINI, F. Biological and Pharmacological Activities of Iridoids: Recent Develoments. Mini-Reviews in Medicinal Chemistry, v. 8, p. 399-420, 2008. VECHIA, L. D.; GNOATTO, S. C. B.; GOSMANN, G. Derivados oleananos e ursanos e sua importância na descoberta de novos fármacos com atividade antitumoral, anti-inflamatória e antioxidante. Química Nova, v. 32, p. 1245-1252, 2009. VIEIRA, H. S. Transformações químicas de diterpenos com atividade biológica. Belo Horizonte: UFMG, 2000. 331p. TESE (Doutorado em Ciências-Química)-Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 2000. WAFO, P.; KAMDEM, R. S. T.; ALI, Z.; ANJUM, S.; BEGUM, A

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