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Opuntisines, 14-membered cyclopeptide alkaloids from fruits of Opuntia stricta var. dillenii isolated by high-performance countercurrent chromatography

2020; Elsevier BV; Volume: 334; Linguagem: Inglês

10.1016/j.foodchem.2020.127552

1873-7072

Frank Surup, Thu Minh Thi Tran, Sebastian Pfütze, Jarmo Budde, Tamer E. Moussa-Ayoub, Sascha Rohn, Gerold Jerz,

Phytochemicals and Antioxidant Activities

Extracts of Opuntia stricta var. dillenii fruits were fractionated by semi-preparative high-performance countercurrent chromatography (HPCCC) to study the secondary metabolite formation, whereby HPCCC showed a superior separation capacity to fractionate minor metabolites compared to HPLC. A family of new peptides was detected in semi-polar fractions when monitoring the HPCCC separation by off-line injections of fractions to ESI-MS/MS. Planar structures of the major compounds, two 14-ring-membered cyclopeptide alkaloids, which were named opuntisines A and B, were elucidated by 1D- and 2D-NMR spectroscopy and HR-ESI-MS/MS spectrometry, while a combination of chemical derivatisation and degradation revealed the stereo-configurations. Specifically, the methods of Marfey and Mosher indicated l-Glu, l-Ile, l-Phe and 1S-configurations, respectively; ROESY correlations revealed 8S, 9S. The novel opuntisine A showed moderate activity against the Gram-negative bacterium Escherichia coli, but no further antibacterial, antifungal nor cytotoxic effects. This bioactive natural product class is reported for the first time in the plant family Cactaceae.