Chemical Composition and Cytotoxicity Evaluation of Essential Oil from Leaves of Casearia Sylvestris, Its Main Compound α-Zingiberene and Derivatives

Abstract

Casearia sylvestris (Salicaceae), popularly known as "guaçatonga", is a plant widely used in folk medicine to treat various diseases, including cancer. The present work deals with the chemical composition as well as the cytotoxic evaluation of its essential oil, its main constituent and derivatives. Thus, the crude essential oil from leaves of C. sylvestris was obtained using a Clevenger type apparatus and analyzed by GC/MS. This analysis afforded the identification of 23 substances, 13 of which corresponded to 98.73% of the total oil composition, with sesquiterpene α-zingiberene accounting for 50% of the oil. The essential oil was evaluated for cytotoxic activity against several tumor cell lines, giving IC 50 values ranging from 12 to 153 μg/mL. Pure α-zingiberene, isolated from essential oil, was also evaluated against the tumor cell lines showing activity for HeLa, U-87, Siha and HL60 cell lines, but with IC 50 values higher than those determined for the crude essential oil. Aiming to evaluate the effect of the double bonds of α-zingiberene on the cytotoxic activity, partially hydrogenated α-zingiberene (PHZ) and fully hydrogenated α-zingiberene (THZ) derivatives were obtained. For the partially hydrogenated derivative only cytotoxic activity to the B16F10-Nex2 cell line (IC 50 65μg/mL) was detected, while totally hydrogenated derivative showed cytotoxic activity for almost all cell lines, with B16F10-Nex2 and MCF-7 as exceptions and with IC 50 values ranging from 34 to OPEN ACCESSMolecules 2013, 18 9478 65 μg/mL. These results indicate that cytotoxic activity is related with the state of oxidation of compound.

Cytotoxicity and genotoxicity of zingiberene on different neuron cell lines in vitro

“…Our findings were in line with previous reports. Similar to our findings, it was reported that the purified a-ZBN from the essential oil from leaves of Casearia sylvestris showed a cytotoxic activity against HeLa, U-87, Siha and HL60 cell lines (Bou et al 2013). Our results are also in agreement with previous studies which have reported that parthenolide demonstrated strong cytotoxicity towards human lung carcinoma (A549), human medulloblastoma (TE671), human colon adenocarcinoma (HT-29) cells in the MTT in vitro assay (Parada-Turska et al 2007).…”

“…ZBN has been used in the odors and cosmetics industry for a long time (Denyer et al 1994). Furthermore, previous reports indicated that ZBN has antifertility, antiviral, antiulcer and anticancer effects (Denyer et al 1994;Millar 1998;Bou et al 2013).…”

Anticancer Activity of Essential Oils: Targeting of Protein Networks in Cancer Cells

“…There is an exciting piece of evidence suggesting that partially hydrogenated α-zingiberene isolated from essential oil from Casearia sylvestris was effective against B16F10-Nex2 cell line. However, surprisingly, fully hydrogenated derivative was effective against MCF-7 and B16F10-Nex2 (Bou et al, 2013).…”

Hydroalcoholic crude extract of Casearia sylvestris Sw. reduces chronic post-ischemic pain by activation of pro-resolving pathways

“…The Casearia sylvestris specie was recently related to the family of Salicaceae (Ferreira et al, 2011) and contains phytochemicals from different classes of medicinal interest such as sesqui- (Bou et al, 2013) and diterpenes (Meesakul et al, 2016).…”