Maytenus ilicifolia or "Espinheira-Santa" is a renowned Brazilian medicinal plant usually used against intestinal and stomach ulcers. Other species with similar thorny leaves have raised great confusion in order to discern the authentic M. ilicifolia. Misidentifications can lead to product adulteration of authentic M. ilicifolia with other species, which can be found on the Brazilian market. The intake of misclassified herbal products potentially could be fatal, demanding faster reliable fingerprinting-based classification methods. In this study, the use of 1 H HR-MAS NMR metabolomics fingerprinting and principal component analysis (PCA) allowed an evaluation of the authenticity for both collected and commercial M. ilicifolia samples, from the content of the flavanol, (−)-epicatechin (2), by observing variations in metabolic patterns. Plant specimen types from cultivated and natural habitats were analyzed by considering seasonal and topological differences. The interand intraplant topological metabolic profiles were found to be affected by seasonal and/or ecological trends such as sunlight, shade, rain, and the presence of pathogens. Moreover, several commercial samples, labeled as M. ilicifolia, were evaluated, but most of these products were of an inadequate quality.T he use of medicinal plants is a foundation of folk medicine in several countries, including Brazil. Some plants offer therapeutic attributes due to the presence of various chemical compounds, and on proper use, they can treat several diseases. However, the intake of misclassified, false, or wrongly labeled unauthentic plants or their products may be fatal. Usually, false products can comprise foreign matter, toxic plant ingredients, or harmful chemical additives that can have adverse effects. 1−3 Brazil has several renowned medicinal plants from the Maytenus genus. This genus represents about 300 species, including Maytenus ilicifolia Mart. ex Reissek (Celastraceae) (synonyms: Celastrus pinifolius Larranãga; Maytenus angustior Briq.; Maytenus hassleri Briq.; Maytenus muelleri Schwacke; Maytenus off icinalis Mabb.; Maytenus pilcomayensis Briq.; and Maytenus aquifolium Mart.). This species is known popularly as "Espinheira-Santa", and it is distributed in different regions of Brazil. 4 According to the Brazilian Pharmacopeia, the leaves of this species have several marker constituents (e.g., flavonoids) and are largely consumed as an infusion (tea), as the raw material, or as extracts and capsules. 4,5 Also, M. ilicifolia and/or M. aquifolium have been cited in the "National List of Medicinal Plants of Interest to the Unified Health System (RENISUS)", and this list contains 71 medicinal plants of interest for therapeutic use by the Brazilian population. 6

Berberis laurina (Berberidaceae) is a well-known medicinal plant used in traditional medicine since ancient times; however, it is scarcely studied to a large-scale fingerprint. This work presents a broad-range fingerprints determination through high-resolution magical angle spinning (HR-MAS) nuclear magnetic resonance (NMR) spectroscopy, a well-established flexible analytical method and one of most powerful “omics” platforms. It had been intended to describe a large range of chemical compositions in all plant parts. Beyond that, HR-MAS NMR allowed the direct investigation of botanical material (leaves, stems, and roots) in their natural, unaltered states, preventing molecular changes. The study revealed 17 metabolites, including caffeic acid, and berberine, a remarkable alkaloid from the genus Berberis L. The metabolic pattern changes of the leaves in the course of time were found to be seasonally dependent, probably due to the variability of seasonal and environmental trends. This metabolites overview is of great importance in understanding plant (bio)chemistry and mediating plant survival and is influenceable by interacting environmental means. Moreover, the study will be helpful in medicinal purposes, health sciences, crop evaluations, and genetic and biotechnological research.

The functionalisation of 2-naphthols and their derivatives has much importance because of their potential pharmaceutical and materials applications. In this context, this work presents a fast, cheap, and efficient method for direct chalcogenylation at position C1 of 2-naphthols promoted by simple bases. The mechanistic studies indicate an ionic mechanism, essentially an electrophilic aromatic substitution, with a key role played by atmospheric oxygen for regeneration of the diorganoyl dichalcogenides.

We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl3 and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines using simple and cheap catalysts. Several control experiments supported the hypothesis that a redox reaction between Fe(III) and KI produces I2, which catalyzed the chalcogenylation.

This research characterizes key metabolites in the leaf from Citronella gongonha Martius (Mart.) Howard (Cardiopteridaceae). All metabolites were assessed in intact leaf tissue by proton (1H) high-resolution magic angle spinning (HR-MAS) nuclear magnetic resonance (NMR) spectroscopy integrated with the principal component analysis (PCA) to depict molecular association with the seasonal change. The major ‘known unknown’ metabolites detected in 1H HR-MAS NMR were derivatives of flavonoid, polyphenolic and monoterpenoid compounds such as kaempferol-3-O-dihexoside, caffeoyl glucoside (2), 3-O-caffeoylquinic acid (3), 5-O-caffeoylquinic acid (4), kingiside (5), 8-epi-kingisidic acid (6), (7α)-7-O-methylmorroniside (7), (7β)-7-O-methylmorroniside (8) and alpigenoside (9) together with the universally occurring sucrose (10), α-glucoses (11, 12), alanine (13), and fatty (linolenic) acid (14). Several of the major metabolites (1, 2–9) were additionally confirmed by liquid chromatography tandem mass spectrometry (LC–MS/MS). In regard with the PCA results, metabolites 1, 2–9 and 14 were influenced by seasonal variation and/or from further (a) biotic environmental conditions. The findings in this work indicate that C. gongonha Mart. is an effective medicinal plant by preserving particularly compounds 2, 3–9 in abundant amounts. Because of close susceptibility with seasonal shift and ecological trends, further longitudinal studies are needed to realize the physiology and mechanism involved in the production of these and new metabolites in this plant under controlled conditions. Also, future studies are recommended to classify different epimers, especially of the phenolics and monoterpenoids in the given plant.

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