Simplex centroid mixture design, DI-ESI-MS, and chemometric analysis-guided isolation of parinarioidin C from bark of Brosimum parinarioides (Moraceae)

Abstract

Brosimum parinarioides , a plant species native to the Amazonian region, is used in folk medicine for the treatment of several diseases. However, knowledge regarding its phytochemical content is scarce. In order to investigate the phytochemical composition of B. parinarioides , an integrative approach based on simplex-centroid design, direct infusion electrospray ionization mass spectrometry (DI-ESI-MS), and chemometric analysis was adopted. According to simplex-centroid design, dichloromethane (DCM), ethyl acetate (AcOEt), and ethanol-based (EtOH) extracts were prepared and analyzed using DI-ESI-MS, and their chemical profile was submitted to principal component analysis (PCA) and hierarchical cluster analysis (HCA). The AcOEt extract from the bark was obtained on a large scale and subjected to chromatographic separation. The multivariate analysis indicated the formation of three groups and highlighted isoliquiritigenin ( 1 ), licoagrochalcone A ( 2 ), caffeic acid glucoside ( 3 ), epicatechin-glycoside ( 4) , caffeic acid ( 5 ), and one unknown compound, as being responsible for the segregation of these groups. Thus, the new compound was isolated and characterized using 1D and 2D nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry (HR-MS) as parinarioidin C ( 10 ). In addition, parinarioidin A ( 6 ), parinarioidin B ( 7 ), 3- O -caffeoylquinic acid ( 8 ), and kanzonol C ( 9 ) were tentatively identified based on manual interpretation of MS/MS spectra. Overall, the integrative approach proposed in the study provided a simple and effective model to dereplicate known compounds and guide the isolation of a new compound from a native amazon species, thus improving the knowledge regarding the phytochemical content of B. parinarioides . • One new compound was isolated from Brosimum parinarioides. • Nine phenolic compounds were identified based on the MS/MS data. • This study provided an effective model to guide the isolation of new natural products.