New natural diterpene-type abietane from Tetradenia riparia essential oil with cytotoxic and antioxidant activities.
Tetradenia riparia (Hochstetter) Codd belongs to the Lamiaceae family and it was introduced in Brazil as an exotic ornamental plant. A previous study showed its antimicrobial, acaricidal and analgesic activities. Two compounds were isolated from essential oil of T. riparia leaves and identified as 9β,13β-epoxy-7-abietene (1), a new one, and 6,7-dehydroroyleanone (2), already reported for another plant. The structure of these compounds was determined by spectroscopic analysis and by comparison with literature data. The cytotoxic activities of the essential oil and compounds 1 and 2 were determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and by tumor cells MDA-MB-435 (human breast carcinoma), HCT-8 (human colon), SF-295 (human nervous system) and HL-60 (human promyelocytic leukemia). The essential oil and compound 1 showed high cytotoxic potential of the cell lines SF-295 (78.06% and 94.80%, respectively), HCT-8 (85.00% and 86.54%, respectively) and MDA-MB-435 (59.48% and 45.43%, respectively). Compound 2 had no cytotoxic activity. The antioxidant activity was determined by 2,2-diphenyl-1-picryl-hydrazyl (DPPH), β-carotene-linoleic acid system and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The inhibitory concentration (IC50 in µg mL-1) for essential oil and compound 2 was, respectively 15.63 and 0.01 for DPPH; 130.1 and 109.6 for β-carotene-linoleic acid and 1524 and 1024 for ABTS. Compound 1 had no antioxidant activity. By fractioning the oil, it was possible to identify two unpublished compounds: 1 with high cytotoxic potential and 2 with high antioxidant potential.
Postgraduate Program in Biotechnology Applied to Agriculture, University, Umuarama, PR 87.502-210, Brazil. cristianigazim@unipar.br.
Zilda Cristiani
ZC
Gazim
Laboratory of Experimental Oncology, Federal University of Ceará, Fortaleza, CE 60.455-970, Brazil. feliperbio@yahoo.com.br.
Felipe
F
Rodrigues
Technology Center, Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro, RJ 21941-909, Brazil. anamorim13@hotmail.com.
Ana Carolina Lourenço
AC
Amorin
Technology Center, Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro, RJ 21941-909, Brazil. claudia.rezendeufrj@gmail.com.
Cláudia Moraes
CM
de Rezende
Institute for Biological Research, University of Belgrade, Belgrade 11000, Serbia. mris@ibiss.bg.ac.rs.
Marina
M
Soković
Faculty of Chemistry, University of Belgrade, Belgrade 11000, Serbia. vtesevic@chem.bg.ac.rs.
Vele
V
Tešević
Faculty of Chemistry, University of Belgrade, Belgrade 11000, Serbia. ivuckovic@chem.bg.ac.rs.
Ivan
I
Vučković
Faculty of Chemistry, University of Belgrade, Belgrade 11000, Serbia. gordana1988@gmail.com.
Gordana
G
Krstić
Postgraduate Program in Health Promotion, University Center of Maringá, Maringá, PR 87050-390, Brazil. luciaelaine@cesumar.br.
Lucia Elaine Ranieri
LE
Cortez
Postgraduate Program in Biotechnology Applied to Agriculture, University, Umuarama, PR 87.502-210, Brazil. nbc@unipar.br.
Nelson Barros
NB
Colauto
Postgraduate Program in Biotechnology Applied to Agriculture, University, Umuarama, PR 87.502-210, Brazil. gianilinde@unipar.br.
Giani Andrea
GA
Linde
Postgraduate Program in Pharmaceutical Sciences, State University of Maringá, Maringá, PR 87020-900, Brazil. dagcortez@uem.br.
Diógenes Aparício Garcia
DA
Cortez
D045784:Abietanes / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D019686:Lamiaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009822:Oils, Volatile / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry
D045784:Abietanes; D000975:Antioxidants; D016166:Free Radical Scavengers; D009822:Oils, Volatile; D010936:Plant Extracts