Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Abstract

Introduction: Xanthones are metabolites with a variety of biological properties. The Clusiaceae family, which until recently included the genus Calophyllum, is recognised for its production of monohydroxylated and polyhydroxylated xanthones. Presently, C. brasiliense is the only Calophyllum spp. known to occur in the Yucatan peninsula. Objective: To use a combination of traditional phytochemical methods and carbon-13 nuclear magnetic resonance ( 13 C-NMR) dereplication analysis to identify xanthones in the stem bark of C. brasiliense. Material and methods: Initial fractionation and purification of the stem bark extract of C. brasiliense produced macluraxanthone (1). Additional xanthones, together with chromanones and terpenoids, were identified using 13 C-NMR dereplication analysis in different semipurified fractions obtained from the low and medium polarity fractions of the stem bark extract of C. brasiliense.Results: Initial identification of macluraxanthone (1) was confirmed by 13 C-NMR dereplication analysis; additionally, 13 C-NMR dereplication analysis allowed the identification of a number of monohydroxylated and polyhydroxylated xanthones, together with chromanones and terpenoids. Conclusion:This study confirms C. brasiliense as a rich source of xanthones and the 13 C-NMR dereplication analysis as a suitable method to quickly identify the presence of different families of secondary metabolites in semipurified fractions.

Chemodiversity of propolis samples collected in various areas of Benin and Congo: Chromatographic profiling and chemical characterization guided by 13C NMR dereplication

“…Thus, the aim of this study was to characterize major compounds from propolis samples collected in various phytogeographical zones of Benin and Congo (Africa) using 13 C nuclear magnetic resonance (NMR) dereplication with MixONat software 43,44 . A preliminary study using a database (DB) containing NPs previously reported from propolis together with their 13 C predicted chemical shifts ( δ C ) did not yield any usable data compared to the satisfactory results usually obtained with plant extracts 43–45 . This can be explained by the chemical composition of propolis, which is highly dependent on the local flora, making it impossible to construct a chemotaxonomic DB.…”

“…43,44 A preliminary study using a database (DB) containing NPs previously reported from propolis together with their 13 C predicted chemical shifts (δ C ) did not yield any usable data compared to the satisfactory results usually obtained with plant extracts. [43][44][45] This can be explained by the chemical composition of propolis, which is highly dependent on the local flora, making it impossible to construct a chemotaxonomic DB. Thus, to decipher major compounds from Beninese and Congolese propolis, in the present work we performed high-performance liquid chromatography coupled with ultraviolet and evaporative light scattering detection mass spectrometry (HPLC-UV-ELSD-MS) and gas chromatography coupled with mass spectrometry (GC-MS) analyses on crude propolis extracts to identify their main structural features and build corresponding DBs of NPs suitable for MixONat software.…”

The application and perspective of NMR and MS based strategies for functional compounds mining in medicinal and dietary plants

“…In addition, as a complementary approach to MS within a chemometric model, MixONat was successfully used for confirming the structures of high anti-advanced glycation end-products (AGEs) activity markers directly from crude bark extracts of Garcinia parvifolia prior to their isolation [50] . Other relevant literature has also reported the use of MixONat for elucidating the composition of propolis samples [51][52] , xanthones from Calophyllum brasiliense [53] , and polyphenolic FCs from Clusia flava Jacq. [54] .…”

Artificial intelligence in microbial natural product drug discovery: current and emerging role

“…160 Recently, using 13 C-NMR, a dereplication soware (MixONat) 124 was developed that allowed the distinction of structurally close NPs, including stereoisomers, and aided the identication of xanthones in Calophyllum brasiliense. 124,161 In another study that used 1 H-NMR, Grienke et al developed a workow ELINA (Eliciting Nature's Activities) based on a heterocovariance analysis, which can detect chemical features that correlate with bioactivity before isolation; using this approach, the authors discovered lanostane triterpenes from the extract of the fungus Fomitopsis pinicola. 125 2.5.…”