1. Structural Characterization and Biological Evaluation of 18-Nor-ent-labdane Diterpenoids from Grazielia gaudichaudeana.
- Author
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Balbinot RB, de Oliveira JAM, Bernardi DI, Melo UZ, Zanqueta ÉB, Endo EH, Ribeiro FM, Volpato H, Figueiredo MC, Back DF, Basso EA, Ruiz ALTG, de Carvalho JE, Foglio MA, Prado Filho BD, Nakamura TU, Nakamura CV, do Carmo MRB, Sarragiotto MH, and Baldoqui DC
- Subjects
- Anti-Infective Agents chemistry, Anti-Infective Agents isolation & purification, Anti-Infective Agents pharmacology, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Antioxidants chemistry, Antiprotozoal Agents chemistry, Antiprotozoal Agents isolation & purification, Antiprotozoal Agents pharmacology, Asteraceae metabolism, Cell Line, Tumor, Cell Survival drug effects, Crystallography, X-Ray, Diterpenes isolation & purification, Diterpenes pharmacology, Fungi drug effects, Gram-Negative Bacteria drug effects, Gram-Positive Bacteria drug effects, Humans, Leishmania drug effects, Magnetic Resonance Spectroscopy, Molecular Conformation, Plant Extracts chemistry, Asteraceae chemistry, Diterpenes chemistry
- Abstract
The phytochemical investigation of Grazielia gaudichaudeana aerial parts yielded 15 compounds, including diterpenes, triterpenes, sterols and flavonoids. With exception to ent-kaurenoic acid diterpenes, the compounds isolated are being described for the first time in this species. Some unusual
1 H-NMR chemical shifts of 18-nor-ent-labdane (7-9) led us carry out a conformational analysis by theoretical calculations in order to support the experimental data. Moreover, due to the limitation of studies focused on pharmacological potential of Grazielia gaudichaudeana, the present study was carried out to investigate the antioxidant, antiproliferative, antiviral, antileishmanial and antimicrobial activities from the extract, fractions and isolated compounds obtained from this species. Ethyl acetate fraction showed significant activity in the antiproliferative assay, with GI50 range of 3.9 to 27.2 μg mL-1 . Dichloromethane fraction, rich in diterpenoids, inhibited all human tumor cell lines tested, and the nor-labdane 7 showed potent cytotoxic activity against glioma and ovary cancer cell lines., (© 2019 Wiley-VHCA AG, Zurich, Switzerland.)- Published
- 2019
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