(+)-Fenchone

Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae).[Pubmed:31813390]

Bull Entomol Res. 2020 Jun;110(3):406-416.

Sitophilus zeamais is a key pest of stored grains. Its control is made, usually, using synthetic insecticides, despite their negative impacts. Botanical insecticides with fumigant/repellent properties may offer an alternative solution. This work describes the effects of Anethum graveolens, Petroselinum crispum, Foeniculum vulgare and Cuminum cyminum essential oils (EOs) and (S)-carvone, cuminaldehyde, estragole and (+)-Fenchone towards adults of S. zeamais. Acute toxicity was assessed by fumigation and topical application. Repellence was evaluated by an area preference bioassay and two-choice test, using maize grains. LC50 determined by fumigation ranged from 51.8 to 535.8 mg L-1 air, with (S)-carvone being the most active. LD50 values for topical applications varied from 23 to 128 microg per adult for (S)-carvone > cuminaldehyde > A. graveolens > C. cyminum > P. crispum. All EOs/standard compounds reduced significantly the percentage of insects attracted to maize grains (65-80%) in the two-choice repellence test, whereas in the area preference bioassay RD50 varied from 1.4 to 45.2 microg cm-2, with cuminaldehyde, (S)-carvone and estragole being strongly repellents. Petroselinum crispum EO and cuminaldehyde affected the nutritional parameters relative growth rate, efficiency conversion index of ingested food and antifeeding effect, displaying antinutritional effects toward S. zeamais. In addition, P. crispum and C. cyminum EOs, as well as cuminaldehyde, showed the highest acetylcholinesterase inhibitory activity in vitro (IC50 = 185, 235 and 214.5 microg mL-1, respectively). EOs/standard compounds exhibited acute toxicity, and some treatments showed antinutritional effects towards S. zeamais. Therefore, the tested plant products might be good candidates to be considered to prevent damages caused by this pest.

Triggering of apoptosis and cell cycle arrest by fennel and clove oils in Caco-2 cells: the role of combination.[Pubmed:31364915]

Toxicol Mech Methods. 2019 Nov;29(9):710-722.

Background: Fennel (Foeniculum vulgare) and clove (Syzygium aromaticum) oils are known for their various biological effects, including anticancer properties. Objective: To investigate the anticancer effect of combined fennel and clove oil treatment on Caco-2 cells and normal human lymphocytes (NHL). Methods: GC-MS, in vitro cytotoxicity, morphological, apoptosis-related marker, and flow cytometric cell cycle distribution analyses were conducted. Results: Seventeen volatile compounds were identified in fennel oil, including trans-anethole (68.3%) and (+)-Fenchone (8.1%). In clove oil, 22 compounds, including eugenol (71.4%) and caryophyllene (8.7%), were identified. IC50 of the fennel, clove, and oil mixture were 300 +/- 5.0, 150 +/- 4.0, and 73 +/- 2.5 microg/mL, respectively with combination index (CI) < 1.0. Mechanistic anticancer properties were investigated using 30, 45, and 60 microg/mL oil mixture. Analysis of apoptotic morphology, flow cytometric cell cycle distribution, and apoptosis-related markers, such as Bcl-2 and Ki-67, confirmed cell cycle arrest and apoptosis induction in Caco-2 cells by the fennel and clove oil combination. Moreover, the oil mixture did not exert significant (p < 0.01) toxicity on NHL in vitro. Conclusion: The oil mixture exerted selective cytotoxicity towards Caco-2 cells through cell cycle arrest and apoptosis, which may occur through synergistic effects between fennel and clove oil active ingredients.