Selina-1,3,7(11)-trien-8-one and Oxidoselina-1,3,7(11)-trien-8-one from Eugenia uniflora Leaf Essential Oil and Their Cytotoxic Effects on Human Cell Lines

• Published in: Molecules (Basel, Switzerland) Vol. 26; no. 3; p. 740
• Main Authors: Ascari, Jociani, Felipe Maciel Pereira, Marcos, Schaffka, Vinicius Monteiro, Nunes, Domingos Sávio, Magalhães, Cássia Gonçalves, Santos, Jânio Sousa, Granato, Daniel, Carmo, Mariana Araújo Vieira do, Azevedo, Luciana, Archilha, Marcos Vinicio Lopes Rodrigues, Riva Scharf, Dilamara
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 31-01-2021; MDPI
• Subjects: Adenocarcinoma; Animal models; Antineoplastic Agents - pharmacology; Antioxidants; Antioxidants - pharmacology; Biotechnology; Cell Line, Tumor; Cell Survival - drug effects; Chromatography; Cytotoxicity; Epithelial cells; Essential oils; Eugenia - chemistry; Eugenia uniflora; Flowers & plants; Hepatoma; Humans; Lipid peroxidation; Lipids; Lung cancer; Lungs; Naphthalenes - pharmacology; NMR; Nuclear magnetic resonance; Oils & fats; Oils, Volatile - chemistry; Optical rotation; oxidoselina-1,3,7-trien-8-one; Peroxidation; Plant Leaves - chemistry; Scavenging; selina-1,3,7-trien-8-one; Sesquiterpenes - pharmacology; Spectrometry; Spectrum analysis; Tumor cells; Brazil; oxidoselina-1,3,7-trien-8-one; selina-1,3,7-trien-8-one; Eugenia uniflora; cytotoxicity
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules26030740

The sesquiterpenes selina-1,3,7(11)-trien-8-one and oxidoselina-1,3,7(11)-trien-8-one were isolated from the essential oil of
L. leaves. The structures were elucidated using spectrometric methods (UV, GC-MS, NMR, and specific optical rotation). The relationship between antioxidant activity, as determined by DPPH assay, and the cytotoxic effect was evaluated using tumor cells, namely lung adenocarcinoma epithelial cells (A549) and human hepatoma carcinoma cells (HepG2), as well as a model of normal human lung fibroblast cells (IMR90). Both compounds did not show prominent free-radical scavenging activity according to DPPH assay, and did not inhibit lipid peroxidation in Wistar rat brain homogenate. The isolated compounds showed pro-oxidative effects and cytotoxicity in relation to the IMR90 cell line.