Pablo Luis B Figueiredo1, Laine C Pinto2, Jamile S da Costa3, Alberto Ray C da Silva4, Rosa Helena V Mourão5, Raquel C Montenegro6, Joyce Kelly R da Silva7, José Guilherme S Maia8. 1. Programa de Pós-Graduação em Química, Universidade Federal do Pará, 66075-110 Belém, PA, Brazil. Electronic address: pablolbf@ufpa.br. 2. Laboratório de Citogenética, Universidade Federal do Pará, 66075-110 Belém, PA, Brazil. 3. Programa Institucional de Bolsas de Iniciação Científica, Universidade Federal do Pará, 66075-110 Belém, PA, Brazil. 4. Coordenação de Botânica, Museu Paraense Emilio Goeldi, 66040-170 Belém, PA, Brazil. 5. Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, 68035-110 Santarém, PA, Brazil. 6. Laboratório de Farmacogenética, Universidade Federal do Ceará, 60455-760 Fortaleza, CE, Brazil. 7. Programa de Pós-Graduação em Química, Universidade Federal do Pará, 66075-110 Belém, PA, Brazil. Electronic address: joycekellys@ufpa.br. 8. Programa de Pós-Graduação em Química, Universidade Federal do Pará, 66075-110 Belém, PA, Brazil. Electronic address: gmaia@ufpa.br.
Abstract
ETHNOPHARMACOLOGICAL RELEVANCE: Oils and extracts of Eugenia uniflora have been reported as antimicrobial, antifungal, antinociceptive, antiprotozoal, antioxidant and cytotoxic. AIM OF THE STUDY: The oils of five specimens (E1 to E5) that occur in the Brazilian Amazon were extracted, analyzed for their chemical composition, and submitted to antioxidant and cytotoxic assays. MATERIAL AND METHODS: Oils were hydrodistilled, analyzed by GC and GC-MS, and submitted to PCA and HCA analyses. The antioxidant activity of the oils was evaluated by the DPPH radical scavenging and the β-carotene/linoleic acid assays. Antiproliferative effects of the oils and curzerene were tested against colon (HCT-116), gastric (AGP-01), and melanoma (SKMEL-19) human cancer cell lines and a normal human fibroblast cell line (MRC-5), using MTT assay. RESULTS: Oxygenated sesquiterpenes and sesquiterpene hydrocarbons such as curzerene, selina-1,3,7(11)-trien-2-one, selina-1,3,7(11)-trien-2-one epoxide, germacrene B, caryophyllene oxide, and (E)-caryophyllene were predominant in the oils. PCA and HCA analyses classified the oils samples into four chemotypes. TEAC values of chemotype II (E3 oil, 228.3 ± 19.2 mg TE/mL) and chemotype III (E4 oil, 217.0 ± 23.3 mg TE/mL) displayed significant antioxidant activities. The oils E2 and E4 showed cytotoxic activity against all cell lines tested HCT-116 (IC50 E2:16.26 μg/mL; IC50 E4:9.28 μg/mL), AGP-01, (IC50 E2:12.60 μg/mL; IC50 E4:8.73 μg/mL), SKMEL-19 (IC50 E2:12.20 μg/mL; IC50 E4:15.42 μg/mL), and MRC-5 (IC50 E2:10.27 μg/mL; IC50 E4:14.95 μg/mL). Curzerene showed the more significant activity against melanoma cells (SKMEL-19, IC50:5.17 μM), induced apoptosis at 5.0 μM and 10.0 μM compared to DMSO, exhibiting a decrease in the cell migration at 5.0 μM and 10.0 μM, after 30 h of treatment. CONCLUSION: The curzerene chemotype oil and E. uniflora oils can be indicated as drug candidates for anticancer activity of the lung, colon, stomach, and melanoma, with a real prospect to their subsequent phytotherapeutic development.
ETHNOPHARMACOLOGICAL RELEVANCE: Oils and extracts of Eugenia uniflora have been reported as antimicrobial, antifungal, antinociceptive, antiprotozoal, antioxidant and cytotoxic. AIM OF THE STUDY: The oils of five specimens (E1 to E5) that occur in the Brazilian Amazon were extracted, analyzed for their chemical composition, and submitted to antioxidant and cytotoxic assays. MATERIAL AND METHODS: Oils were hydrodistilled, analyzed by GC and GC-MS, and submitted to PCA and HCA analyses. The antioxidant activity of the oils was evaluated by the DPPH radical scavenging and the β-carotene/linoleic acid assays. Antiproliferative effects of the oils and curzerene were tested against colon (HCT-116), gastric (AGP-01), and melanoma (SKMEL-19) humancancer cell lines and a normal human fibroblast cell line (MRC-5), using MTT assay. RESULTS: Oxygenated sesquiterpenes and sesquiterpene hydrocarbons such as curzerene, selina-1,3,7(11)-trien-2-one, selina-1,3,7(11)-trien-2-one epoxide, germacrene B, caryophyllene oxide, and (E)-caryophyllene were predominant in the oils. PCA and HCA analyses classified the oils samples into four chemotypes. TEAC values of chemotype II (E3 oil, 228.3 ± 19.2 mg TE/mL) and chemotype III (E4 oil, 217.0 ± 23.3 mg TE/mL) displayed significant antioxidant activities. The oils E2 and E4 showed cytotoxic activity against all cell lines tested HCT-116 (IC50 E2:16.26 μg/mL; IC50 E4:9.28 μg/mL), AGP-01, (IC50 E2:12.60 μg/mL; IC50 E4:8.73 μg/mL), SKMEL-19 (IC50 E2:12.20 μg/mL; IC50 E4:15.42 μg/mL), and MRC-5 (IC50 E2:10.27 μg/mL; IC50 E4:14.95 μg/mL). Curzerene showed the more significant activity against melanoma cells (SKMEL-19, IC50:5.17 μM), induced apoptosis at 5.0 μM and 10.0 μM compared to DMSO, exhibiting a decrease in the cell migration at 5.0 μM and 10.0 μM, after 30 h of treatment. CONCLUSION: The curzerene chemotype oil and E. uniflora oils can be indicated as drug candidates for anticancer activity of the lung, colon, stomach, and melanoma, with a real prospect to their subsequent phytotherapeutic development.
Authors: Lidiane Diniz do Nascimento; Sebastião Gomes Silva; Márcia Moraes Cascaes; Kauê Santana da Costa; Pablo Luis Baia Figueiredo; Cristiane Maria Leal Costa; Eloisa Helena de Aguiar Andrade; Lênio José Guerreiro de Faria Journal: Molecules Date: 2021-04-30 Impact factor: 4.411
Authors: Jamile S da Costa; Adenilson S Barroso; Rosa Helena V Mourão; Joyce Kelly R da Silva; José Guilherme S Maia; Pablo Luis B Figueiredo Journal: Biomolecules Date: 2020-02-19
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Authors: Igor A Schepetkin; Gulmira Özek; Temel Özek; Liliya N Kirpotina; Andrei I Khlebnikov; Mark T Quinn Journal: Molecules Date: 2021-06-15 Impact factor: 4.411
Authors: Jamile S da Costa; Ellen de Nazaré S da Cruz; William N Setzer; Joyce Kelly do R da Silva; José Guilherme S Maia; Pablo Luis B Figueiredo Journal: Biomolecules Date: 2020-08-06
Authors: Nayara Sabrina Freitas Alves; Suzana G Kaory Inoue; Adriana Ribeiro Carneiro; Ulisses Brigatto Albino; William N Setzer; José Guilherme Maia; Eloisa Helena Andrade; Joyce Kelly R da Silva Journal: PLoS One Date: 2022-01-21 Impact factor: 3.240