Metabolic fingerprinting of banana passion fruits and its correlation with quorum quenching activity

Abstract Banana passion fruit of the Passiflora genus, are commercially cultivated on a small to medium scale, mainly as edible fruits or as components of traditional herbal medicines. This subgenus comprises several species and hybrid specimens that grow readily in the wild. Due to their taxonomical complexity, many of these species have recently been reclassified (Ocampo Perez and Coppens d’Eeckenbrugge, 2017), and their chemical profile has still to be determined. In this study, an 1H NMR-based platform was applied to the chemical profiling of seven wild species of the Passiflora subgenus, and UHPLC-DAD-MS was additionally used for the identification of phenolic compounds. A total of 59 compounds were detected including 26 O- and C-glycosidated flavonoids and polyphenols, nine organic acids, seven amino acids, GABA, sucrose, glucose, myo-inositol, and five other non-identified compounds. Two of the identified compounds are the previously undescribed C-glycosyl flavonoids, apigenin-4′-O-β-glucopyranosyl, 8-C-β-(6″acetyl)-glucopyranoside and apigenin-4-O-β-glucopyranosyl-8-C-β-neohesperidoside. These C-glycosyl flavonoids were isolated to confirm their proposed structures by NMR and LCMS analysis. The PCA score plots obtained from the 1H NMR data of the studied Passiflora samples showed P. cumbalensis and P. uribei as the species with the most distinguishable chemical profile. In addition, a correlation analysis using OPLS-DA was conducted between 1H-NMR data and the quorum quenching activity (QQ) of Chromobacterium violaceum ATCC 31532. This analysis revealed P. lehmannii, and P. uribei extracts to be the most active, and apigenin-4′-O-β-glucopyranosyl, 8-C-β-(6″acetyl)-glucopyranoside and apigenin-4-O-β-glucopyranosyl-8-C-β-neohesperidoside were identified as possibly responsible for the QQ activity. To confirm this, QQ activity of both compounds was tested against C. violaceum ATCC 3153. An inhibition of violacein production of 0.135 mM (100 μg/mL) and 0.472 mM (300 μg/mL) was observed for apigenin-4′-O-β-glucopyranosyl,8-C-β-(6″acetyl)-glucopyranoside and apigenin-4-O-β-glucopyranosyl-8-C-β-neohesperidoside respectively, while bacterial growth was unaffected in both cases. Furthermore, both compounds showed the ability to inhibit the production of the toxoflavin of the phytopathogen Burkholderia glumae ATCC 33617.