A New Cytotoxic Naphthoquinone and Other Chemical Constituents of Sinningia reitzii

Author(s)

Silva, Adson S. ^[1] ; Amorim, Magali S. ^[1] ; Fonseca, Mariana M. ^[2] ; Salvador, Marcos J. ^[2] ; de Sa, Eduardo L. ^[1] ; Stefanello, Maria Elida A. ^[1]

Affiliation

^[1] Univ Fed Parana, Dept Quim, BR-81530900 Curitiba, Parana - Brazil

^[2] Univ Estadual Campinas, Inst Biol, Dept Biol Vegetal, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 30, n. 10, SI, p. 2060-2065, OCT 2019.
• Web of Science Citations: 0

Abstract

Phytochemical study of Sinningia reitzii (Gesneriaceae) led to the isolation of three new naphtoquinones, 6.7-dimethoxydunnione, 7-hydroxy-6-methoxydunnione, and 5 -hydroxy6,7-dimethoxydunnione from the tubers, together with four known compounds, 7-hydroxydunnione, 8-hydroxydunn lone. 5-hydroxy-6,7-dimethoxy-alpha-dunnione. and 8-hydroxydeydrodunnione. Aerial parts furnished five known compounds, 5-hydroxy-6,7-dimethoxydunniol. 6.8-dihydroxy-7-methoxy2-O-methyldunniol, loureirin B, jacaranone, and methyl 4-hydroxyphenylacetate. Compounds 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-oc-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 -hydrox y-6,7-dimethox ydunnione, 7-hydroxydunnione, 8-hydroxydunnione, 5-hydroxy6,7-dimethoxy-alpha-dunnione. Compounds 6,7-dimethoxydunnione, 8-hydroxydunnione, 5-hydroxy6,7-dimethoxy-alpha-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 mu mol L-1). and was inactive against 3T3 fibroblasts (IC50 > 100 mu mol L-1). Compounds 8-hydroxydunnione, 5-hydroxy-6.7-dimethoxya-dunnione and 8-hydroxydeydrodunnione were inactive against all tested cell lines. (AU)

• FAPESP's process: 15/03726-8 - Integrated chemical and biological study in the search for bioactive substances in plants* and development of analytical procedures. *(Amaranthaceae, Gesneriaceae, Myrtaceae e Annonaceae)
• Grantee: Marcos José Salvador
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/03598-5 - Preventive effect of Ilex paraguariensis preparations (chimarrão, terere and mate tea) against damages caused by chronic ethanol consumption: comparative analysis of preparation technology, chemical profile and evaluation of therapeutic effect and safety
• Grantee: Mariana Mesquita Fonseca
• Support Opportunities: Scholarships in Brazil - Doctorate