Variability of Volatile Oils Composition, Tannins, and Phenols from Campomanesia adamantium (CAMBESS.) O. Berg
DOI:
https://doi.org/10.21664/2238-8869.2022v11i4.p206-223Palavras-chave:
carobinha, cerrado, Myrtaceae, plantas medicinais, óleos essenciaisResumo
Campomanesia adamantium (Myrtaceae), conhecida como "guabiroba-do-campo", é um arbusto nativo do Cerrado popularmente usado como anti-séptico anti-inflamatório, antidiarreico e do trato urinário. Os objetivos deste estudo foram: avaliar a variabilidade sazonal dos fenóis totais e taninos e compostos químicos dos óleos voláteis das folhas de C. adamantium em um período de 12 meses. As folhas e flores foram coletadas em Bela Vista, Goiás, Brasil. Os óleos voláteis foram obtidos por hidrodestilação em aparelho de Clevenger e analisados por GC/MS. A determinação dos fenóis totais e taninos foi realizada pelo método de Hagerman e Butler. Os principais compostos dos óleos das folhas foram γ-elemeno, limoneno, epóxido de italiceno, β-funebreno, biciclogermacreno, linalol e das flores foram sabineno, limoneno, linalol, tricicleno e salicilato de metila. O teor total de fenóis variou de 3,75% a 9,56% e o teor de taninos, de 2,25% a 4,84%. Concluiu-se que o melhor período para coleta das folhas com maior índice de fenóis e taninos é a baixa precipitação. Este trabalho representa a primeira descrição da variabilidade sazonal dos óleos essenciais, taninos e fenóis totais de C. adamantium coletados em Bela Vista.
Referências
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Barros FMC, Zambarda EO, Heinzmann BM, Carlos A, Mallmann CA 2009. Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae). Quim Nova 32 (4): 861-867.
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Benyahia S, Benayache S, Benayache F, León F, Quintana J, Lopez M, Hernández JC, Estévez F, Bermejo J 2005. Cladocalol a pentacyclic 28- nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity. Phytochem 66: 627-632.
Brasil. 2010. Farmacopeia Brasileira. 5ª ed., Atheneu, São Paulo, 546 pp.
Cardoso CAL, Silva JRM, Kataoka VMF, Brum CS, Poppi NR 2008. Avaliação da atividade antioxidante, toxicidade e composição química por CG-EM do extrato hexânico das folhas de Campomanesia pubescens. Rev Cien Farm Bas Aplic 29: 297-301.
Cardoso C, Salmazzo G, Honda NK, Prates CB, Vieira MC, Coelho RG 2010. Antimicrobial activity of the extracts and fractions of hexanic fruits of Campomanesia species (Myrtaceae). J Med Food 13 (5): 1273-1276.
Coutinho ID, Coelho RG, Kataoka VMF, Honda NK, Silva JRM, Vilegas W, Cardoso CAL. 2008a. Determination of phenolic compounds and evaluation of antioxidant capacity of Campomanesia adamantium leaves. Eclét Quím 33 (4): 53-60.
Coutinho ID, Poppi NR, Cardoso C. 2008b. Identification of the volatile compounds of leaves and flowers in guavira (Campomanesia adamantium O. Berg.). J Essent Oil 20 (5): 405-407.
Coutinho ID, Cardoso CAL, Ré-poppi, Melo AM, Vieira MC, Honda NK, Coelho RG. 2009. Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities of essential oil of Campomanesia adamantium (Cambess.) O. Berg (Guavira). Braz J Pharm Sci 45 (4): 767-776.
Coutinho ID, Kataoka VMF, Honda NK, Coelho RG, Vieira MC, Claudia AL, Cardoso CAL 2010. Influência da variação sazonal nos teores de flavonóides e atividade antioxidante das folhas de Campomanesia adamantium (Cambess.) O. Berg, Myrtaceae. Braz J Pharmacog 20(3): 322-327.
Djoukeng JD, Abou-mansour E, Tabacchi R, Tapondjou AL, Bouda H, Lontsi D. 2005. Antibacterial triterpenes from Syzygium guineense (Myrtaceae). J Ethnopharmacol 101: 283-286.
Ferreira ACF, Neto JC, Silva ACM, Kuster RM, CARVALHO DP 2006. Inhibition of thyroid peroxidase by Myrcia uniflora flavonoids. Chem Res Toxicol 19 (3): 351-355.
Ferreira LC, Grabe-Guimarães A, Michel MC, Guimarães RG, Rezende SA. 2013. Anti-inflammatory and antinociceptive activities of Campomanesia adamantium. J Ethnopharmacol 145 (1): 100-108.
Gobbo-Neto L, Lopes NP 2007. Plantas medicinais: fatores de influência no conteúdo de metabólitos secundários. Quim Nova 30 (2): 374-381.
Gomes SM, Somavilla NSDN, Gomes-Bezerra KM, Miranda SC, Carvalho OS, Graciano-Ribeiro D 2009. Anatomia foliar de espécies de Myrtaceae: contribuições à taxonomia e filogenia. Acta Bot Bras 23(1): 223-238.
Gressler E, Pizo MA, Morellato LPC 2006. Polinização e dispersão de sementes em Myrtaceae do Brasil. Braz J Bot 29 (4): 509-530.
Gu JQ, Park EJ, Luyengi L, Hawthorne ME, Mehta RG, Farnsworth N R, Pezzuto JM, Kinghorn AD 2001. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochem 58: 121-127.
Hammer Ø, Harper DAT, Ryan PD 2001. PAST: Paleontological Statistics Software package for education and data analysis. Palaeontol Electr 4:1-9.
Hassiotis CN, Ntana F, Lazari DM, Poulios S, Vlachonasios KE 2014. Environmental and developmental factors affect essential oil production and quality of Lavandula angustifolia during flowering period. Ind Crop Prod 62: 359-366.
INMET. 2017. Instituto Nacional de Meteorologia. Ministério da agricultura, pecuária e abastecimento. [updated 2017 May]. Available from: http://www.inmet.gov.br/portal/.
Klafke JZ, Silva MA, Panigas TF, Belli KC, Oliveira MF, Barichello MM, Rigo FK, Rossato MF, Santos ARS, Pizzolatti MG, Ferreira J, Viecili PR 2010. Effects of Campomanesia xanthocarpa on biochemical, hematological and oxidative stress parameters in hypercholesterolemic patients. J Ethnopharmacol 127: 299-305.
Kuhlmann M 2012. Frutos e sementes do Cerrado atrativos para a fauna. Ed. Rede de Sementes do Cerrado, Brasília, 360 pp.
Lee YL, Ding P 2016. Production of essential oil in plants: Ontogeny, secretory structures and seasonal variations. PJSRR 2(1): 1-10
Lima HRP, Kaplan MAC, Cruz AVM 2003. Influência dos fatores abióticos na produção e variabilidade de terpenoides em plantas. Floresta e Ambiente 10:71–77.
Lima DF, Goldenberg R, Sobral M 2011. O gênero Campomanesia (Myrtaceae) no estado do Paraná, Brasil. Rodriguésia 62 (3): 683-693.
Limberger RP, Apel MA, Sobral M, Menut LC 2001. Chemical composition of essential oils from some Campomanesia Species (Myrtaceae). J Essent Oil Res 13 (2): 113-115.
Lorenzi H, Lacerda M, Bacheret L 2008. Frutas brasileiras e exóticas cultivadas. Ed. Instituto Plantarum, São Paulo, 640 pp.
Markman BEO, Bacchi EM, Kato ETM 2004. Antiulcerogenic effects of Campomanesia xanthocarpa. J Ethnopharmacol 94 (1): 55-7.
Mole S, Waterman PG 1987. A critical analysis of techniques for measuring tannins in ecological studies. Oecologia 72: 137-147.
Mustafa K, Perry NB, Weavers RT 2005. Lipophilc C-methyl flavonoids with no B-ring oxygenation in Metrosideros species (Myrtaceae). Biochem Syst Ecol 33: 1049-1059.
NIST 1998. National Institute of Standards and Technology, PC Version of the NIST/EPA/NIH Mass Spectral Database. U.S. Department of Commerce, Gaithersburg.
Oliveira JDD, Alves DKM, Miranda MLD, Alves JM, Xavier MN, Cazal CDM, Alves CCF 2017. Chemical composition of essential oil extracted from leaves of Campomanesia adamantium subjected to different hydrodistillation times. Ciência Rural 47(1):1-7.
Osório C, Alarcon M, Moreno C, Bonilla A, Barrios J, Garzón C, DUQUE C 2006. Characterization of odor-active volatiles in champa (Campomanesia lineatifolia R. & P.). J Agricult Food Chem 54: 509-516.
Pascoal ACRF, Lourenco CC, Sodek L, Tamashiro JY, Franchi JRGC, Nowill AE, Stefanello MEA, Salvador MJ 2011. Essential oil from the leaves of Campomanesia guaviroba (DC.) Kiaersk. (Myrtaceae): Chemical composition, antioxidant and cytotoxic activity. J Essent Oil Res 23 (5): 34-37.
Pascoal ACRF, Ehrenfried CA, Lopez BGC, Araujo TM, Pascoal VDB, Gilioli R, Anhê GF, Ruiz ALTG, Carvalho JE, Stefanello MEA, Salvador MJ 2014. Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study. Molecules 19 (2): 1843-1855.
Paula JAM, Paula JR, Bara MTF, Rezende MH, Ferreira HD 2008. Estudo farmacognóstico das folhas de Pimenta pseudocaryophyllus (Gomes) L.R. Landrum Myrtaceae. Rev Bras Farmacogn 18: 265-278.
Pavan FR, Leite CQF, Coelho RG, Coutinho ID, Honda NK, Cardoso CAL, Vilegas W, Leite SRA, Sato DN 2009. Evaluation of anti-Mycobacterium tuberculosis activity of Campomanesia adamantium (Myrtaceae). Quim Nova 32 (5): 1222-1226.
Piva MG 2002. O Caminho das plantas medicinais: estudo etnobotânico. v 1, Editora Mondrian, Rio de Janeiro, 313 pp.
Sobral M, Proença C, Souza M, Mazine F, Lucas E 2010. Myrtaceae. Lista de espécies da flora do Brasil. [updated 2010 Sep 23]. Available from: http://www.floradobrasil.jbrj.gov.br/.
STATSOFT INC. 2004. Statistica: data analysis software system, version 7. Tulsa. Available from: http://www.statsoft.com/
Sá S, Chaul LT, Alves VF, Fiuza TS, Leonice LMF, Vaz BG, Ferri PH, Borges LL, Paula JR 2018. Phytochemistry and antimicrobial activity of Campomanesia adamantium. Rev Bras Farmacog 28: 303–311.
Stefanello MEA, Cervi AC, Wisniewski JrA, Simionatto EL 2008. Essential Oil Composition of Campomanesia adamantium (Camb) O. Berg. J Essent Oil Res 20(5): 424-425.
Tanaka T, Orii Y, Nonaka G, Nishioka I, Kouno I 1996. Syzyginins A and B, two ellagitannins from Syzygium aromaticum. Phytochem 43: 1345-1348.
Silva E, Soares M, Mariane B, Vallim M, Pascon R, Sartorelli P, Lago J 2013. The seasonal variation of the chemical composition of essential oils from Porcelia macrocarpa R. E. Fries (Annonaceae) and their antimicrobial activity. Molecules 18: 13574-13587.
Umehara K, Singh IP, Etoh H, Takasaki M, Konoshima T 1998. Five phloroglucinol-monoterpene adducts from Eucalyptus grandis. Phytochem 49(6): 1699-1704.
Van Den Dool H, Kratz PD 1963. Generalization of the Retention Index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11: 463-471.
Viscardi DZ, Oliveira VS, Arrigoa JS, Piccinelli AC, Cardoso CAL, Maldonadee IR, Kassuyac CAL, Sanjinez-Argandona EJ 2017. Anti-inflammatory, and antinociceptive effects of Campomanesia adamantium microencapsulated pulp. Rev Bras Farmacog 27: 220–227.
Ward JH 1963. Hierarchical grouping to optimize an objective function. J Am Stat Assoc. 58: 66-103.
Yang LL, Lee CY, Yen KY 2000. Induction of apoptosis by hydrolyzable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett 157: 65-75.
Yoshikawa M, Shimada H, Nishida N, Toguchida I, Yamahara J, Matsuda H 1998. Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): Structures of myrciacitrins I and II and myrciaphenones A and B. Chem Pharm Bul 46(1):113-119.
Adati RT, Ferro VO 2006. Volatile oil constituents of Campomanesia phaea (O. Berg) Landrum. (Myrtaceae). J Essent Oil Res 18 (6): 691-692.
Barros FMC, Zambarda EO, Heinzmann BM, Carlos A, Mallmann CA 2009. Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae). Quim Nova 32 (4): 861-867.
Batish DR, Singh HP, Kohli RK, Kaur S 2008. Eucalyptus essential oil as a natural pesticide. For Ecol Manag 256: 2166-2174.
Benyahia S, Benayache S, Benayache F, León F, Quintana J, Lopez M, Hernández JC, Estévez F, Bermejo J 2005. Cladocalol a pentacyclic 28- nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity. Phytochem 66: 627-632.
Brasil. 2010. Farmacopeia Brasileira. 5ª ed., Atheneu, São Paulo, 546 pp.
Cardoso CAL, Silva JRM, Kataoka VMF, Brum CS, Poppi NR 2008. Avaliação da atividade antioxidante, toxicidade e composição química por CG-EM do extrato hexânico das folhas de Campomanesia pubescens. Rev Cien Farm Bas Aplic 29: 297-301.
Cardoso C, Salmazzo G, Honda NK, Prates CB, Vieira MC, Coelho RG 2010. Antimicrobial activity of the extracts and fractions of hexanic fruits of Campomanesia species (Myrtaceae). J Med Food 13 (5): 1273-1276.
Coutinho ID, Coelho RG, Kataoka VMF, Honda NK, Silva JRM, Vilegas W, Cardoso CAL. 2008a. Determination of phenolic compounds and evaluation of antioxidant capacity of Campomanesia adamantium leaves. Eclét Quím 33 (4): 53-60.
Coutinho ID, Poppi NR, Cardoso C. 2008b. Identification of the volatile compounds of leaves and flowers in guavira (Campomanesia adamantium O. Berg.). J Essent Oil 20 (5): 405-407.
Coutinho ID, Cardoso CAL, Ré-poppi, Melo AM, Vieira MC, Honda NK, Coelho RG. 2009. Gas Chromatography-Mass Spectrometry (GC-MS) and evaluation of antioxidant and antimicrobial activities of essential oil of Campomanesia adamantium (Cambess.) O. Berg (Guavira). Braz J Pharm Sci 45 (4): 767-776.
Coutinho ID, Kataoka VMF, Honda NK, Coelho RG, Vieira MC, Claudia AL, Cardoso CAL 2010. Influência da variação sazonal nos teores de flavonóides e atividade antioxidante das folhas de Campomanesia adamantium (Cambess.) O. Berg, Myrtaceae. Braz J Pharmacog 20(3): 322-327.
Djoukeng JD, Abou-mansour E, Tabacchi R, Tapondjou AL, Bouda H, Lontsi D. 2005. Antibacterial triterpenes from Syzygium guineense (Myrtaceae). J Ethnopharmacol 101: 283-286.
Ferreira ACF, Neto JC, Silva ACM, Kuster RM, CARVALHO DP 2006. Inhibition of thyroid peroxidase by Myrcia uniflora flavonoids. Chem Res Toxicol 19 (3): 351-355.
Ferreira LC, Grabe-Guimarães A, Michel MC, Guimarães RG, Rezende SA. 2013. Anti-inflammatory and antinociceptive activities of Campomanesia adamantium. J Ethnopharmacol 145 (1): 100-108.
Gobbo-Neto L, Lopes NP 2007. Plantas medicinais: fatores de influência no conteúdo de metabólitos secundários. Quim Nova 30 (2): 374-381.
Gomes SM, Somavilla NSDN, Gomes-Bezerra KM, Miranda SC, Carvalho OS, Graciano-Ribeiro D 2009. Anatomia foliar de espécies de Myrtaceae: contribuições à taxonomia e filogenia. Acta Bot Bras 23(1): 223-238.
Gressler E, Pizo MA, Morellato LPC 2006. Polinização e dispersão de sementes em Myrtaceae do Brasil. Braz J Bot 29 (4): 509-530.
Gu JQ, Park EJ, Luyengi L, Hawthorne ME, Mehta RG, Farnsworth N R, Pezzuto JM, Kinghorn AD 2001. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochem 58: 121-127.
Hammer Ø, Harper DAT, Ryan PD 2001. PAST: Paleontological Statistics Software package for education and data analysis. Palaeontol Electr 4:1-9.
Hassiotis CN, Ntana F, Lazari DM, Poulios S, Vlachonasios KE 2014. Environmental and developmental factors affect essential oil production and quality of Lavandula angustifolia during flowering period. Ind Crop Prod 62: 359-366.
INMET. 2017. Instituto Nacional de Meteorologia. Ministério da agricultura, pecuária e abastecimento. [updated 2017 May]. Available from: http://www.inmet.gov.br/portal/.
Klafke JZ, Silva MA, Panigas TF, Belli KC, Oliveira MF, Barichello MM, Rigo FK, Rossato MF, Santos ARS, Pizzolatti MG, Ferreira J, Viecili PR 2010. Effects of Campomanesia xanthocarpa on biochemical, hematological and oxidative stress parameters in hypercholesterolemic patients. J Ethnopharmacol 127: 299-305.
Kuhlmann M 2012. Frutos e sementes do Cerrado atrativos para a fauna. Ed. Rede de Sementes do Cerrado, Brasília, 360 pp.
Lee YL, Ding P 2016. Production of essential oil in plants: Ontogeny, secretory structures and seasonal variations. PJSRR 2(1): 1-10
Lima HRP, Kaplan MAC, Cruz AVM 2003. Influência dos fatores abióticos na produção e variabilidade de terpenoides em plantas. Floresta e Ambiente 10:71–77.
Lima DF, Goldenberg R, Sobral M 2011. O gênero Campomanesia (Myrtaceae) no estado do Paraná, Brasil. Rodriguésia 62 (3): 683-693.
Limberger RP, Apel MA, Sobral M, Menut LC 2001. Chemical composition of essential oils from some Campomanesia Species (Myrtaceae). J Essent Oil Res 13 (2): 113-115.
Lorenzi H, Lacerda M, Bacheret L 2008. Frutas brasileiras e exóticas cultivadas. Ed. Instituto Plantarum, São Paulo, 640 pp.
Markman BEO, Bacchi EM, Kato ETM 2004. Antiulcerogenic effects of Campomanesia xanthocarpa. J Ethnopharmacol 94 (1): 55-7.
Mole S, Waterman PG 1987. A critical analysis of techniques for measuring tannins in ecological studies. Oecologia 72: 137-147.
Mustafa K, Perry NB, Weavers RT 2005. Lipophilc C-methyl flavonoids with no B-ring oxygenation in Metrosideros species (Myrtaceae). Biochem Syst Ecol 33: 1049-1059.
NIST 1998. National Institute of Standards and Technology, PC Version of the NIST/EPA/NIH Mass Spectral Database. U.S. Department of Commerce, Gaithersburg.
Oliveira JDD, Alves DKM, Miranda MLD, Alves JM, Xavier MN, Cazal CDM, Alves CCF 2017. Chemical composition of essential oil extracted from leaves of Campomanesia adamantium subjected to different hydrodistillation times. Ciência Rural 47(1):1-7.
Osório C, Alarcon M, Moreno C, Bonilla A, Barrios J, Garzón C, DUQUE C 2006. Characterization of odor-active volatiles in champa (Campomanesia lineatifolia R. & P.). J Agricult Food Chem 54: 509-516.
Pascoal ACRF, Lourenco CC, Sodek L, Tamashiro JY, Franchi JRGC, Nowill AE, Stefanello MEA, Salvador MJ 2011. Essential oil from the leaves of Campomanesia guaviroba (DC.) Kiaersk. (Myrtaceae): Chemical composition, antioxidant and cytotoxic activity. J Essent Oil Res 23 (5): 34-37.
Pascoal ACRF, Ehrenfried CA, Lopez BGC, Araujo TM, Pascoal VDB, Gilioli R, Anhê GF, Ruiz ALTG, Carvalho JE, Stefanello MEA, Salvador MJ 2014. Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study. Molecules 19 (2): 1843-1855.
Paula JAM, Paula JR, Bara MTF, Rezende MH, Ferreira HD 2008. Estudo farmacognóstico das folhas de Pimenta pseudocaryophyllus (Gomes) L.R. Landrum Myrtaceae. Rev Bras Farmacogn 18: 265-278.
Pavan FR, Leite CQF, Coelho RG, Coutinho ID, Honda NK, Cardoso CAL, Vilegas W, Leite SRA, Sato DN 2009. Evaluation of anti-Mycobacterium tuberculosis activity of Campomanesia adamantium (Myrtaceae). Quim Nova 32 (5): 1222-1226.
Piva MG 2002. O Caminho das plantas medicinais: estudo etnobotânico. v 1, Editora Mondrian, Rio de Janeiro, 313 pp.
Sobral M, Proença C, Souza M, Mazine F, Lucas E 2010. Myrtaceae. Lista de espécies da flora do Brasil. [updated 2010 Sep 23]. Available from: http://www.floradobrasil.jbrj.gov.br/.
STATSOFT INC. 2004. Statistica: data analysis software system, version 7. Tulsa. Available from: http://www.statsoft.com/
Sá S, Chaul LT, Alves VF, Fiuza TS, Leonice LMF, Vaz BG, Ferri PH, Borges LL, Paula JR 2018. Phytochemistry and antimicrobial activity of Campomanesia adamantium. Rev Bras Farmacog 28: 303–311.
Stefanello MEA, Cervi AC, Wisniewski JrA, Simionatto EL 2008. Essential Oil Composition of Campomanesia adamantium (Camb) O. Berg. J Essent Oil Res 20(5): 424-425.
Tanaka T, Orii Y, Nonaka G, Nishioka I, Kouno I 1996. Syzyginins A and B, two ellagitannins from Syzygium aromaticum. Phytochem 43: 1345-1348.
Silva E, Soares M, Mariane B, Vallim M, Pascon R, Sartorelli P, Lago J 2013. The seasonal variation of the chemical composition of essential oils from Porcelia macrocarpa R. E. Fries (Annonaceae) and their antimicrobial activity. Molecules 18: 13574-13587.
Umehara K, Singh IP, Etoh H, Takasaki M, Konoshima T 1998. Five phloroglucinol-monoterpene adducts from Eucalyptus grandis. Phytochem 49(6): 1699-1704.
Van Den Dool H, Kratz PD 1963. Generalization of the Retention Index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11: 463-471.
Viscardi DZ, Oliveira VS, Arrigoa JS, Piccinelli AC, Cardoso CAL, Maldonadee IR, Kassuyac CAL, Sanjinez-Argandona EJ 2017. Anti-inflammatory, and antinociceptive effects of Campomanesia adamantium microencapsulated pulp. Rev Bras Farmacog 27: 220–227.
Ward JH 1963. Hierarchical grouping to optimize an objective function. J Am Stat Assoc. 58: 66-103.
Yang LL, Lee CY, Yen KY 2000. Induction of apoptosis by hydrolyzable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett 157: 65-75.
Yoshikawa M, Shimada H, Nishida N, Toguchida I, Yamahara J, Matsuda H 1998. Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): Structures of myrciacitrins I and II and myrciaphenones A and B. Chem Pharm Bul 46(1):113-119.
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2022-12-30
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SÁ, Stone de; FIUZA, Tatiana de Sousa; BORGES, Leonardo Luiz; CUNHA, Luiz Carlos da; OLIVEIRA NETO, Jerônimo Raimundo de; PAULA, José Realino de. Variability of Volatile Oils Composition, Tannins, and Phenols from Campomanesia adamantium (CAMBESS.) O. Berg. Fronteira: Journal of Social, Technological and Environmental Science, [S. l.], v. 11, n. 4, p. 206–223, 2022. DOI: 10.21664/2238-8869.2022v11i4.p206-223. Disponível em: https://revistas2.unievangelica.edu.br/index.php/fronteiras/article/view/4030. Acesso em: 24 nov. 2024.
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