Essential oils are generally produced to confer the protection of medicinal plants against several natural enemies. Variations of chemical and physical environmental factors exert significant influences on plant development. They hence may affect the quality and quantity of volatile organic metabolites of interest and, therefore, the economic applications of essential oils. This research focused on the effects of the harvest region on the production and analytes present in Tunisian Pimpinella lutea Desf. Apiaceae that were collected in three different growing environments (North and South Bizerta and Tabarka). Essential oils extracted from a variety of genotypes were analyzed, for the first time, using gas chromatography and mass spectrometry (GC/FID and GC/MS). The determination of the percentage of essential oil components allowed the recognition of three chemotypes: α-trans-Bergamotene quantified at a percentage of 18.1% in North Bizerta (NBEO), muurola-4,10(14)-dien-1-β-ol identified in South Bizerta (10.1%, SBEO) and acora-3,7(14)-dien present in a high level of 29.1% in Tabarka population (TEO). The richness of different populations in sesquiterpenes (60.2–78.1%) suggests that Pimpinella lutea Desf. may be used in different industrial segments.

A detailed phytochemical investigation has been carried out on the aerial parts of G. foetida leading to the isolation of 29 pure compounds, mainly belonging to the amorfrutin and polyphenol classes. Among them, the new amorfrutin N (5) and exiguaflavone L (21) were isolated and their structures elucidated by means of HR-ESIMS and NMR. All the isolated compounds were investigated for modulation of mitochondrial activity and stimulation of glucose uptake via GLUT transporters, two metabolic processes involved in intracellular glucose homeostasis, which, therefore, correlate with the incidence of metabolic syndrome. These experiments revealed that amorfrutins were active on both targets, with amorfrutin M (17) and decarboxyamorfrutin A (2) emerging as mitochondrial stimulators, and amorfrutin 2 (12) as a glucose uptake promoter. However, members of the rich chalcone/flavonoid fraction also proved to contribute to this activity.