A reliable validated high-performance liquid chromatography-photodiode array detection method for quantification of terpenes in Copaifera pubiflora, Copaifera trapezifolia, and Copaifera langsdorffii oleoresins

References

• ANVISA, RE899. 2003. Guia para Validação de Métodos Analíticos e Bioanalíticos. Brasília: ANVISA, Diário Oficial da União.
   Google Scholar
• Arruda C, Aldana Mejía JA, Ribeiro VP, Gambeta Borges CH, Martins CHG, Sola Veneziani RC, Ambrósio SR, Bastos JK. 2019. Occurrence, chemical composition, biological activities and analytical methods on Copaifera genus, A review. Biomed Pharmacother. 109:1–20.
   PubMed Web of Science ®Google Scholar
• Baccarin T, Muceneeki RS, Bresolin TM, Yunes RA, Malheiros A, Lucinda-Silva RM. 2011. Development and validation of an HPLC-PDA method for the determination of myrsinoic acid B in the extracts of Rapanea ferruginea Mez. Talanta. 85(2):1221–1224.
   PubMed Web of Science ®Google Scholar
• Barbosa PCS, Medeiros RS, Sampaio PTB, Vieira G, Wiedemann LSM, Veiga-Junior VF. 2012. Influence of abiotic factors on the chemical composition of copaiba oil (Copaifera multijuga Hayne): soil composition, seasonality and diameter at breast height. J Braz Chem Soc. 23(10):1823–1833.
   Web of Science ®Google Scholar
• Bardají DK, Da silva JJ, Bianchi TC, De Souza ED, De Oliveira PF, Leandro LF, Rogez HL, Venezianni RC, Ambrosio RS, Tavares D, et al. 2016. Copaifera reticulata oleoresin: chemical characterization and antibacterial properties against oral pathogens. Anaerobe. 40:18–27.
   PubMed Web of Science ®Google Scholar
• Borges CHG, Cruz MG, Carneiro LJ, da Silva JJM, Bastos JK, Tavares DC, de Oliveira PF, Rodrigues V, Veneziani RCS, Parreira RLT, et al. 2016. Oleoresin and its main non volatile terpenes: schistosomicidal properties. Chem Biodivers. 13(10):1348–1356.
   PubMed Web of Science ®Google Scholar
• Borges VRA, Ribeiro AF, Anselmo CS, Cabral LM, de Sousa VPJ. 2013. Development of a high performance liquid chromatography method for quantification of isomers β-caryophyllene and α-humulene in copaiba oleoresin using the Box-Behnken design. J Chromatogr B Analyt Technol Biomed Life Sci. 940:35–41.
   PubMed Web of Science ®Google Scholar
• Cardona L, García B, Giménez JE, Pedro JR. 1992. A shorter route to the synthesis of (+)-junenol isojunenol, and their coumarate esters from (−)-santonin. Tetrahedron. 48(5):851–860.
   Web of Science ®Google Scholar
• Carneiro L, Bianchi T, da Silva J, Oliveira L, Borges C, Lemes D, Veneziani RCS, Bastos JK, Ambrósio SR. 2017. Development and validation of a rapid and reliable RP-HPLC-PDA method for the quantification of six diterpenes in Copaifera duckei, Copaifera reticulata and Copaifera multijuga Oleoresins. Braz Chem Soc. 4:729–737.
   Google Scholar
• Carneiro LJ, Tasso TO, Santos MFC, Goulart MO, dos Santos RA, Bastos JK, da Silva JJM, Crotti AEM, Parreira RLT, Orenha RP, et al. 2020. Copaifera multijuga, Copaifera pubiflora and Copaifera trapezifolia oleoresins: chemical characterization and in vitro cytotoxic potential against tumoral cell lines. J Braz Chem Soc. 31(8):1679–1689.
   Web of Science ®Google Scholar
• da Silva JJM, Crevelin EJ, Carneiro LJ, Rogez H, Veneziani RCS, Ambrósio SR, Beraldo Moraes LA, Bastos JK. 2017. Development of a validated ultra-high-performance liquid chromatography tandem mass spectrometry method for determination of acid diterpenes in Copaifera oleoresins. J Chromatogr A. 1515:81–90.
   PubMed Web of Science ®Google Scholar
• Da Trindade R, da Silva JK, Setzer WN. 2018. Copaifera of the neotropics: a review of the phytochemistry and pharmacology. IJMS. 19(5):1511.
   Google Scholar
• Langenheim JH. 1994. Higher plant terpenoids: a phytocentric overview of their ecological roles. J Chem Ecol. 20(6):1223–1280.
   PubMed Web of Science ®Google Scholar
• Maciel MAM, Pinto AC, Veiga Jr VF, Grynberg NF, Echevarria A. 2002. Plantas medicinais: a necessidade de estudos multidisciplinares. Quím Nova. 25(3):429–438.
   Web of Science ®Google Scholar
• Ohsaki A, Yan LT, Ito S, Edatsugi H, Iwata D, Komoda Y. 1994. The isolation and in vivo potent antitumour activity of clerodane diterpenoid from the oleoresin of the Brazilian medicinal plant, Copaifera langsdorffii Desfon. Bioorg Med Chem. 4(24):2889–2892.
   Google Scholar
• Oliveira LC, Porto TS, Junior AHC, Santos MFC, Ramos HP, Braun GH, de Lima Paula LA, Bastos JK, Furtado NAJC, Parreira RLT, et al. 2020. Schistosomicidal activity of kaurane, labdane and clerodane-type diterpenes obtained by fungal transformation. Process Biochem. 98:34–40.
   Web of Science ®Google Scholar
• Reynolds WF, Enríquez RG, Escobar LI, Lozoya X. 1984. Total assignment of 1H and 13C spectra of kauradien-9(11),16-oic acid with the aid of heteronuclear correlated 2D spectra optimized for geminal and vicinal 13C–1H coupling constants: or what to do when "INADEQUATE" is impossible. Can J Chem. 62(11):2421–2425.
   Web of Science ®Google Scholar
• Silva EA, Takahashi JÁ, Boaventura MAD, Oliveira AB. 1999. The biotransformation of ent-kaur-16-en-19-oic acid by Rhizopus stolonifer. Phytochemistry. 52(3):397–400.
   PubMed Web of Science ®Google Scholar
• Souza AB, Moreira MR, Borges CHG, Simão MR, Bastos JK, de Sousa JPB, Ambrosio SR, Veneziani RCS. 2013. Development and validation of a rapid RP-HPLC method for analysis of (-)-copalic acid in copaiba oleoresin. Biomed Chromatogr. 27(3):280–283.
   PubMed Web of Science ®Google Scholar
• Tappin MRR, Pereira JFG, Lima LA, Siani AC, Mazzei JL, Ramos MFS. 2004. Análise química quantitativa para a padronização do óleo de copaíba por cromatografia em fase gasosa de alta resolução. Quím Nova. 27(2):236–240.
   Google Scholar
• Veiga VF, Jr., Patitucci ML, Pinto AC. 1997. Authenticity control of commercial copaiba oils by high resolution gas chromatography. Quim Nova. 20:612.
   Web of Science ®Google Scholar