New natural diterpene-type abietane from Tetradenia riparia essential oil with cytotoxic and antioxidant activities

• Published in: Molecules (Basel, Switzerland) Vol. 19; no. 1; pp. 514 - 524
• Main Authors: Gazim, Zilda Cristiani, Rodrigues, Felipe, Amorin, Ana Carolina Lourenço, de Rezende, Cláudia Moraes, Soković, Marina, Tešević, Vele, Vučković, Ivan, Krstić, Gordana, Cortez, Lucia Elaine Ranieri, Colauto, Nelson Barros, Linde, Giani Andrea, Cortez, Diógenes Aparício Garcia
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01-01-2014; MDPI
• Subjects: 6,7-dehydroroyleanone; 9β,13β-epoxy-7-abietene; abietane diterpenes; Antimicrobial agents; antioxidant activity; Antioxidants; Antioxidants - chemistry; Antioxidants - pharmacology; Cell Line, Tumor; Cell Proliferation - drug effects; Cytotoxicity; cytotoxicity activity; Diterpenes, Abietane - chemistry; Diterpenes, Abietane - pharmacology; Diterpenes, Abietane - toxicity; Electronic mail systems; essential oil; Free Radical Scavengers - chemistry; Free Radical Scavengers - pharmacology; Humans; Inhibitory Concentration 50; Lamiaceae; Lamiaceae - chemistry; Molecular Structure; NMR; Nuclear magnetic resonance; Nuclear Magnetic Resonance, Biomolecular; Oils & fats; Oils, Volatile - chemistry; Plant Extracts - chemistry; Riparia; Tetradenia riparia; Brazil; Serbia
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules19010514

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.