Distribution of 5,6-dihydro-α-pyrones by electrospray ionization ion trap mass spectrometry in different aerial parts of Hyptis monticola

Hyptis monticola Mart. ex Benth. (Lamiaceae) is an endemic species of altitude regions of Brazil. From the leaves of this plant, two 5,6-dihydro-α-pyrones, named monticolides A and B, have been reported as cytotoxic agents against different tumor cell lines. The isolation by high-speed countercurrent chromatography in combination with recycling preparative high-performance liquid chromatography of the undescribed monticolides C-F is presented. These compounds corresponded to a series of related monticolide derivatives differing from each other by the number of acyl substituents. Their characterization by mass spectrometry and nuclear magnetic resonance is also presented, in conjunction with an evidence by a simple chemical correlation for their absolute stereochemistry. The distribution of these chemical markers in extracts of flowers, leaves and branches collected in different seasons by electrospray ionization ion trap mass spectrometry in positive mode was analyzed. Multivariate data analyses indicated that seasonality affects monticolide concentrations in different organs of the aerial parts. Monticolides A-F seem to be present as the original markers of the analyzed plant. However, mono-, di- and triacetylated monticolides can undergo acid-catalyzed transesterifications and their natural yields estimated were affected during the isolation procedures. [Display omitted] •Monticolides C-F were isolated as undescribed 6-heptyl-5,6-dihydro-2H-pyran-2-ones.•Distribution of monticolides A-F in different plant organs were analyzed by UHPLC-ESI- MS/MS.•Multivariate data analyses indicated that seasonality affects monticolide concentrations.•Monticolides A-F seems to be present as original makers of the analyzed plant material.•Mono-, di- and triacetylated montecolides can undergo acid-catalyzed transesterifications.