Phytochemical Characterization and TRPA1/TRPM8 Modulation Profile of the Cannabigerol-Rich Cannabis sativa L. Chemotype IV.

The first detailed phytochemical analysis of the cannabigerol (CBG)-rich chemotype IV of Cannabis sativa L. resulted in the isolation of the expected cannabigerolic acid/cannabigerol (CBGA/CBG) and cannabidiolic acid/cannabidiol (CBDA/CBD) and of nine new phytocannabinoids (5-13), which were fully characterized by HR-ESIMS and 1D and 2D NMR. These included mono- or dihydroxylated CBGA/CBG analogues, a congener with a truncated side chain (10), cyclocannabigerol B (11), and the CBD derivatives named cannabifuranols (12 and 13). Cyclocannabigerol B and cannabifuranols are characterized by a novel phytocannabinoid structural architecture. The isolated phytocannabinoids were assayed on the receptor channels TRPA1 and TRPM8, unveiling a potent dual TRPA1 agonist/TRPM8 antagonist profile for compounds 6, 7, and 14. Chiral separation of the two enantiomers of 5 resulted in the discovery of a synergistic effect of the two enantiomers on TRPA1.

Comparison of Biostimulant Treatments in Acmella oleracea Cultivation for Alkylamides Production.

Acmella oleracea is a promising cosmetic, nutraceutical, and pharmaceutical ingredient, and plants with high levels of active compounds are needed in the market. Cultivation can be valuable if sufficient levels of alkylamides are present in plant material. In this regard the application of biostimulants can be an innovative approach to increase yield of cultivation or bioactive compound levels. A. oleracea plants were cultivated in Northern Italy in an experimental site using three different types of biostimulants, triacontanol-based mixture (Tria), an extract from plant tissues (LL017), and seaweed extract (Swe). Plants were grown in the field in two different growing seasons (2018 and 2019). After treatments inflorescences were harvested and the quali-quantitative analysis of alkylamides and polyphenols was performed. Treated and control plants were compared for yields, morphometric measurements, quali-quantitative composition in secondary metabolites. Overall results show that both triacontanol-based mixture and the LL017 positively influenced plant growth (Tria >+ 22%; LL017 >+ 25%) and flower production (Tria >+ 34%; LL017 >+ 56%). The amount of alkylamides and polyphenols in flowers were between 2.0-5.2% and 0.03-0.50%, respectively. Biostimulant treatments ensure higher cultivation yields and allow maintenance of the alkylamide and polyphenol levels based on % (w/w), thus offering an advantage in the final quantity of extractable chemicals. Furthermore, data revealed that samples harvested in late season show a decrease of polyphenols.

HPLC-DAD-MS identification of bioactive secondary metabolites from Ferula communis roots.

A simple HPLC method was developed to distinguish between 'poisonous' and 'non-poisonous' chemotypes of Ferula communis. The method was performed on a C8 reverse phase analytical column using a binary eluent (aqueous TFA 0.01%-TFA 0.01% in acetonitrile) under gradient condition. The two chemotypes showed different fingerprints. The identification of five coumarins and eleven daucane derivatives by HPLC-diode array detection (HPLC-DAD) and HPLC-MS is described. A coumarin, not yet described, was detected.