A New Cytotoxic Naphthoquinone and Other Chemical Constituents of Sinningia reitzii
| Autor: | Adson S. Silva, Mariana Mesquita Fonseca, Eduardo L. de Sá, Marcos José Salvador, Magali S. Amorim, Maria Élida Alves Stefanello |
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| Rok vydání: | 2019 |
| Předmět: |
biology
Sinningia reitzii Absolute configuration General Chemistry Gesneriaceae biology.organism_classification Naphthoquinone HeLa chemistry.chemical_compound naphthoquinones medicine.anatomical_structure chemistry Biochemistry Phytochemical Cell culture medicine Fibroblast Cytotoxicity IC50 cytotoxic activity |
| Zdroj: | Journal of the Brazilian Chemical Society v.30 n.10 2019 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ Journal of the Brazilian Chemical Society, Volume: 30, Issue: 10, Pages: 2060-2065, Published: 21 OCT 2019 |
| ISSN: | 0103-5053 |
| DOI: | 10.21577/0103-5053.20190054 |
| Popis: | Phytochemical study of Sinningia reitzii (Gesneriaceae) led to the isolation of three new naphtoquinones, 6,7-dimethoxydunnione, 7-hydroxy-6-methoxydunnione, and 5-hydroxy-6,7-dimethoxydunnione from the tubers, together with four known compounds, 7-hydroxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione, and 8-hydroxydeydrodunnione. Aerial parts furnished five known compounds, 5-hydroxy-6,7-dimethoxydunniol, 6,8-dihydroxy-7-methoxy-2-O-methyldunniol, loureirin B, jacaranone, and methyl 4-hydroxyphenylacetate. Compounds 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione, 8-hydroxydeydrodunnione, 5-hydroxy-6,7-dimethoxydunniol and 6,8-dihydroxy-7-methoxy-2-O-methyldunniol had been previously reported in the tubers of S. reitzii. Density functional theory was used to assign the absolute configuration of compounds 6,7-dimethoxydunnione, 7-hydroxy-6-methoxydunnione 5-hydroxy-6,7-dimethoxydunnione, 7-hydroxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione. Compounds 6,7-dimethoxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione and 8-hydroxydeydrodunnione were evaluated for cytotoxicity against PC3 (prostate), SKMEL 103 (melanoma), and HeLa (cervix) human cancer, and 3T3 fibroblast cell lines, using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. Compound 6,7-dimethoxydunnione displays cytotoxic activity against all the tumor cell lines tested (half maximal inhibitory concentration, IC50, 4.47-26.2 µmol L-1), and was inactive against 3T3 fibroblasts (IC50 > 100 µmol L-1). Compounds 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione and 8-hydroxydeydrodunnione were inactive against all tested cell lines. |
| Databáze: | OpenAIRE |
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