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Molecules 2014, 19(1), 514-524; doi:10.3390/molecules19010514
Article

New Natural Diterpene-Type Abietane from Tetradenia riparia Essential Oil with Cytotoxic and Antioxidant Activities

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1 Postgraduate Program in Biotechnology Applied to Agriculture, University, Umuarama, PR 87.502-210, Brazil 2 Laboratory of Experimental Oncology, Federal University of Ceará, Fortaleza, CE 60.455-970, Brazil 3 Technology Center, Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro, RJ 21941-909, Brazil 4 Institute for Biological Research, University of Belgrade, Belgrade 11000, Serbia 5 Faculty of Chemistry, University of Belgrade, Belgrade 11000, Serbia 6 Postgraduate Program in Health Promotion, University Center of Maringá, Maringá, PR 87050-390, Brazil 7 Postgraduate Program in Pharmaceutical Sciences, State University of Maringá, Maringá, PR 87020-900, Brazil
* Author to whom correspondence should be addressed.
Received: 12 December 2013 / Revised: 24 December 2013 / Accepted: 25 December 2013 / Published: 3 January 2014
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Abstract

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.
Keywords: Tetradenia riparia; essential oil; abietane diterpenes; 9β,13β-epoxy-7-abietene; 6,7-dehydroroyleanone; cytotoxicity activity; antioxidant activity Tetradenia riparia; essential oil; abietane diterpenes; 9β,13β-epoxy-7-abietene; 6,7-dehydroroyleanone; cytotoxicity activity; antioxidant activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Gazim, Z.C.; Rodrigues, F.; Amorin, A.C.L.; Rezende, C.M.; Soković, M.; Tešević, V.; Vučković, I.; Krstić, G.; Cortez, L.E.R.; Colauto, N.B.; Linde, G.A.; Cortez, D.A.G. New Natural Diterpene-Type Abietane from Tetradenia riparia Essential Oil with Cytotoxic and Antioxidant Activities. Molecules 2014, 19, 514-524.

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