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Volatile Composition and Biological Activities of the Leaf Essential Oil from Zanthoxylum limoncello Grown in Oaxaca, México

2018; Wiley; Volume: 16; Issue: 2 Linguagem: Inglês

10.1002/cbdv.201800498

1612-1880

Nemesio Villa‐Ruano, Yesenia Pacheco‐Hernández, José Alejo Zárate‐Reyes, Ramiro Cruz Durán, Edmundo Lozoya‐Gloria,

Phytochemical compounds biological activities

Abstract Zanthoxylum limoncello is a native plant from southern Mexico which is used as a timber source, condiment and as a traditional medicine. Herein, we report on the volatile content of the leaf essential oil and its biological activities. The annual essential oils (2015–2018) contained volatile organic compounds which exhibited a moderate growth inhibitory activity against H. pylori ATCC 53504 (MIC 121.4–139.7 μg mL −1 ), 26695 (MIC 85.5–94.9 μg mL −1 ) and J99 (MIC 94.7–110.4 μg mL −1 ). These hydrodistillates contained 2‐undecanone (31.6–36.8 %; MIC 185.3–199.2 μg mL −1 ) and 2‐undecenal (25.1–35.7 %; MIC 144.8–111.3 μg mL −1 ) as the most abundant compounds which were partially involved in the anti ‐H. pylori activity. The human ornithine decarboxylase enzyme (ODC1), which shows increased activity in several cancer types, was non‐competitively inhibited (V max 2.7>0.8 K cat s −1 ) by the essential oil of Z. limoncello as well as by 2‐undecanone and 2‐undecenal in accordance to in vitro kinetic studies. In silico calculations strongly suggest that the carbonyl group of these oxygenated hydrocarbons interacts with both Asn319 and Ala39 at the subunit A of ODC1. Considering that Ala39 is located close to Asn44, a crucial amino acid of the ODC's allosteric site, the non‐competitive inhibition of the enzyme by 2‐undecanone and 2‐undecenal is endorsed. Finally, the essential oil of Z. limoncello and its main volatiles showed a significant ( p <0.01) and prolonged repellent effect against Aedes aegypti .