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The undifferentiated cambial meristematic cell (CMC) has been recognized as a value-added production platform for plant natural products in comparison to the dedifferentiated plant cell line (DDC). In a time-based approach at 0, 24, 48, and 72 h, the present study aimed at investigating the phytochemical metabolome of methyl jasmonate (MeJA)-elicited CMC cultures derived from sweet basil (Ocimum basilicum L.), including primary and secondary metabolites analyzed using GC/TOF-MS post-silylation and RP-UPLC-C 18 -FT-MS/MS, respectively, as well as the analysis of aroma composition using headspace SPME-GC-MS. The results revealed a stress response in primary metabolism manifested by an increase in amino and organic acids reaching their maximum levels after 48 (1.3-fold) and 72 (1.7-fold) h, respectively. In addition, phenolic acids (e.g., sagerinic acid, rosmarinic acid, and 3-O-methylrosmarinic acid) followed by flavonoid aglycones (e.g., salvigenin and 5,6,4'-trihydroxy-7,3'-dimethoxyflavone) were the most abundant with prominent increases at 48 (1.2-fold) and 72 (2.1-fold) h, respectively. The aroma was intensified by the elicitation along the time, especially after 48 and 72 h. Furthermore, multivariate data analyses, including principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) confirmed elicitation effect, especially post 48 and 72 h. The study further assessed the effect of MeJA elicitation on the antioxidant and polyphenolic content. The cultures at 48 h demonstrated a significant (p < 0.05) antioxidant activity concurrently with correlation with total polyphenolic content using Pearson's correlation. Our study provides new insights to the elicitation impact on primary and secondary metabolism, in addition to aroma profile, to orchestrate the stress response and in relation to antioxidant effect., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

Eucalyptus: L'Hér. (Myrtaceae) is one of the economically most important and widely cultivated trees for wood crop purposes worldwide. Climatic changes together with the constant need to expand plantations to areas that do not always provide optimal conditions for plant growth highlight the need to assess the impact of abiotic stresses on eucalypt trees. We aimed to unveil the drought effect on the leaf metabolome of commercial clones with differential phenotypic response to this stress. For this, seedlings of 13 clones were grown at well-watered (WW) and water-deficit (WD) conditions and their leaf extracts were subjected to comparative analysis using ultra-high performance liquid chromatography coupled to mass spectrometry (UPLC-MS) and nuclear magnetic resonance spectroscopy (NMR). UPLC-MS and NMR analyses led to the annotation of over 100 molecular features of classes such as cyclitols, phenolics, flavonoids, formylated phloroglucinol compounds (FPCs) and fatty acids. Multivariate data analysis was employed for specimens' classifications and markers identification from both platforms. The results obtained in this work allowed us to classify clones differing in drought tolerance. Classification models were validated using an extra subset of samples. Tolerant plants exposed to water deficit accumulated arginine, gallic acid derivatives, caffeic acid and tannins at higher levels. In contrast, stressed drought-sensitive clones were characterised by a significant reduction in glucose, inositol and shikimic acid levels. These changes in contrasting drought response eucalypt pave ways for differential outcomes of tolerant and susceptible phenotypes. Under optimal growth conditions, all clones were rich in FPCs. These results can be used for early screening of tolerant clones and to improve our understanding of the role of these biomarkers in Eucalyptus tolerance to drought stress., Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests:Mohamed A. Farag reports financial support was provided by Alexander von Humboldt Foundation. Clarice Noleto-Dias reports financial support was provided by National Council for Scientific and Technological Development., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

Sapotaceae is a flowering plants family reported for its richness in triterpenoid saponins. Sapotaceae comprises a large number of fruit-producing plants of nutritional and medicinal value. Different species of family Sapotaceae received a considerable interest owing to their rich triterpenoid saponins content of a myriad pharmacological effects and health benefits. Several databases were searched for collecting papers for this review in the scope of phytochemistry, bioactivity and record of triterpenoid saponins from family Sapotacese such as PubMed, Google Scholar, Web of Science, Scopus and Reaxys from 1990 till now. Triterpenoid saponins reported from Sapotaceae plants are mostly of protobassic acid, 16-α-hydroxyprotobassic acid, bayogenin, and oleanolic acid derivatives with both monodesmosidic and/or bidesmosidic attached sugar side chains. Besides, the most frequently attached sugar units are glucose, glucoronic acid, apiose, xylose, rhamnose, and arabinose. The reported health effects of Sapotaceae plants in folk medicine in relation to their bioactive saponins were also reviewed with special attention to anti-inflammatory, antiulcer activity, antimicrobial activity, cytotoxic, anti-hypercholesterolemic, antioxidant, and immunomodulatory activities. This review aims to present a holistic compile on the phytochemical and biological diversity of triterpenoid saponins reported from family Sapotaceae with future perspectives., (Copyright © 2022 Elsevier Ltd. All rights reserved.)

Portulaca oleracea, commonly known as purslane, is a popular plant of considerable value for its nutritive composition as well as traditional medicinal uses. P. oleracea is reported to possess neuroprotective, antimicrobial, antidiabetic, antioxidant, anti-inflammatory, antiulcerogenic, and anticancer activities. Three taxa of P. oleracea L. (P. oleracea, P. rausii and P. granulatostellulata) are grown as mixed populations in several locations in Egypt. The close morphological similarities among these taxa warrants development of methods for their correct identification or classification. We aimed in this study to assess metabolome differences among three P. oleracea taxa via ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) in the context of their genetic diversity and/or geographical origin. A total of 85 metabolites were identified including 6 amino acids, 22 phenolic compounds, 16 alkaloids, and 11 fatty acids characterized based on their MS n and UV spectra. Methoxylated flavone glycosides, O-flavonoids, C-flavonoids and four previously undescribed cyclodopa alkaloids are reported in P. oleracea for the first time. Multivariate data analyses were used for samples classification and revealing that cyclodopa alkaloids (oleracein A, C, K and N) contributed the most for accessions classification. To the best of our knowledge, this study presents the first metabolite profile of Portulaca and its compositional differences that provide chemical based evidence for its nutritive and/or health benefits., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Bauhinia L. (Fabaceae) comprises ca. 300-350 plant species, many of which are traditionally used in folk medicine for their antidiabetic, antioxidant and anti-inflammatory effects. Bauhinia s.l. recently has been subdivided into 9 genera based on phylogenetic data: Bauhinia s.str., Barklya, Brenierea, Gigasiphon, Lysiphyllum, Phanera, Piliostigma, Schnella (American Phanera) and Tylosema. The aerial parts of 8 species corresponding to 5 genera were analyzed: Bauhinia forficata, Bauhinia variegata, B. variegata var. candida, Bauhinia galpinii, Schnella glabra, Piliostigma racemosa, Phanera vahlii and Lysiphyllum hookeri. Leaves and shoots were subjected to metabolite profiling via UHPLC-PDA-qTOF-MS coupled to multivariate data analyzes to identify compound compositional differences. A total of 90 metabolites were identified including polyphenols and fatty acids; flavonoid conjugates accounted for most of the metabolite variation observed. This study provides a comprehensive map of polyphenol composition in Bauhinia and phytochemical species aggregations are consistent with recent Bauhinia genus taxonomic relationship derived from phylogenetic studies. DPPH radical scavenging and α-glucosidase inhibitory assays were also performed to assess selected aspects of the antioxidant and antidiabetic potential for the examined species with respect to metabolite profiles., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

The metabolomic differences in phenolics from leaves derived from 3 artichoke cultivars (Cynara scolymus): American Green Globe, French Hyrious and Egyptian Baladi, collected at different developmental stages, were assessed using UHPLC-MS coupled to chemometrics. Ontogenic changes were considered as leaves were collected at four different time intervals and positions (top and basal) during artichoke development. Unsupervised principal component analysis (PCA) and supervised orthogonal projection to latent structures-discriminant analysis (O2PLS-DA) were used for comparing and classification of samples harvested from different cultivars at different time points and positions. A clear separation among the three investigated cultivars was revealed, with the American Green Globe samples found most enriched in caffeic acid conjugates and flavonoids vs. other cultivars. Furthermore, these metabolites also showed a marked effect on the discrimination between leaf samples from cultivars harvested at different positions, regardless of the plant age. Metabolite absolute quantifications further confirmed that discrimination was mostly influenced by phenolic compounds, namely caffeoylquinic acids and flavonoids. This study demonstrates an effect of artichoke leaf position, regardless of plant age, on its secondary metabolites composition. To the best of our knowledge, this is the first report for compositional differences among artichoke leaves, based on their positions, via a metabolomic approach and suggesting that top positioned artichoke leaves present a better source of caffeoylquinic acids, compared to basal ones., (Copyright © 2014 Elsevier Ltd. All rights reserved.)

Several species of the genus Urtica (especially Urtica dioica, Urticaceae), are used medicinally to treat a variety of ailments. To better understand the chemical diversity of the genus and to compare different accessions and different taxa of Urtica, 63 leaf samples representing a broad geographical, taxonomical and morphological diversity were evaluated under controlled conditions. A molecular phylogeny for all taxa investigated was prepared to compare phytochemical similarity with phylogenetic relatedness. Metabolites were analyzed via UPLC-PDA-MS and multivariate data analyses. In total, 43 metabolites were identified, with phenolic compounds and hydroxy fatty acids as the dominant substance groups. Principal component analysis (PCA) and hierarchical clustering analysis (HCA) provides a first structured chemotaxonomy of the genus. The molecular data present a highly resolved phylogeny with well-supported clades and subclades. U. dioica is retrieved as both para- and polyphyletic. European members of the U. dioica group and the North American subspecies share a rather similar metabolite profile and were largely retrieved as one, nearly exclusive cluster by metabolite data. This latter cluster also includes - remotely related - Urtica urens, which is pharmaceutically used in the same way as U. dioica. However, most highly supported phylogenetic clades were not retrieved in the metabolite cluster analyses. Overall, metabolite profiles indicate considerable phytochemical diversity in the genus, which largely falls into a group characterized by high contents of hydroxy fatty acids (e.g., most Andean-American taxa) and another group characterized by high contents of phenolic acids (especially the U. dioica-clade). Anti-inflammatory in vitro COX1 enzyme inhibition assays suggest that bioactivity may be predicted by gross metabolic profiling in Urtica., (Copyright © 2013. Published by Elsevier Ltd.)

The demand to develop efficient and reliable analytical methods for the quality control of herbal medicines and nutraceuticals is on the rise, together with an increase in the legal requirements for safe and consistent levels of active principles. Here, we describe an ultra-high performance liquid chromatography method (UHPLC) coupled with quadrupole high resolution time of flight mass spectrometry (qTOF-MS) analysis for the comprehensive measurement of metabolites from three Cynara scolymus (artichoke) cultivars: American Green Globe, French Hyrious, and Egyptian Baladi. Under optimized conditions, 50 metabolites were simultaneously quantified and identified including: eight caffeic acid derivatives, six saponins, 12 flavonoids and 10 fatty acids. Principal component analysis (PCA) was used to define both similarities and differences among the three artichoke leaf cultivars. In addition, batches from seven commercially available artichoke market products were analysed and showed variable quality, particularly in caffeic acid derivatives, flavonoid and fatty acid contents. PCA analysis was able to discriminate between various preparations, including differentiation between various batches from the same supplier. To the best of our knowledge, this study provides the first approach utilizing UHPLC-MS based metabolite fingerprinting to reveal secondary metabolite compositional differences in artichoke leaf extracts., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Onobrychis viciifolia (sainfoin) is a traditional fodder legume showing multiple benefits for the environment, animal health and productivity but weaker agronomic performance in comparison to other legumes. Benefits can be mainly ascribed to the presence of polyphenols. The polyphenol metabolism in O. viciifolia was studied at the level of gene expression, enzyme activity, polyphenol accumulation and antioxidant activity. A screening of 37 accessions regarding each of these characters showed a huge variability between individual samples. Principal component analysis revealed that flavonols and flavan 3-ols are the most relevant variables for discrimination of the accessions. The determination of the activities of dihydroflavonol 4-reductase and flavonol synthase provides a suitable screening tool for the estimation of the ratio of flavonols to flavan 3-ols and can be used for the selection of samples from those varieties that have a specific optimal ratio of these compounds for further breeding., (Copyright © 2012 Elsevier Ltd. All rights reserved.)

Glycyrrhiza glabra, commonly known as licorice, is a popular herbal supplement used for the treatment of chronic inflammatory conditions and possesses anticancer and antiviral activities. This species contains a plethora of phytochemicals including terpenoids, saponins, flavonoids, polyamines and polysaccharides. The full complement of bioactive compounds has yet to be elucidated, a step necessary in order to explain its medicinal use. There are over 30 species in the Glycyrrhiza genus world-wide, most of which have been little characterized in terms of phytochemical or pharmacological properties. Here, large scale multi-targeted metabolic profiling and fingerprinting techniques were utilized to help gain a broader insight into Glycyrrhiza species chemical composition. UV, MS and NMR spectra of extracted components were connected with NMR, MS, and multivariate analyses data from Glycyrrhiza glabra, Glycyrrhiza uralensis, Glycyrrhiza inflata and Glycyrrhiza echinata. Major peaks in (1)H NMR and MS spectra contributing to the discrimination among species were assigned as those of glycyrrhizin, 4-hydroxyphenyl acetic acid, and glycosidic conjugates of liquiritigenin/isoliquiritigenin. Primary metabolites profiling using GC-MS revealed the presence of cadaverine, an amino acid, exclusively found in G. inflata roots. Both LC-MS and NMR were found effective techniques in sample classification based on genetic and or geographical origin as revealed from derived PCA analysis., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

The chloroform extract of the aerial parts of Caralluma russeliana yielded four acylated pregnane glycosides, namely russeliosides E-H, three were found now. The structures of the compounds were elucidated using MS, 1H NMR, 13C NMR, 1H-1H COSY, HMQC, NOESY and HMBC experiments.

An integrated approach utilizing HPLC-UV-ESI-MS and GC-MS was used for the large-scale and systematic identification of polyphenols in Medicago truncatula root and cell culture. Under optimized conditions, we were able to simultaneously quantify and identify 35 polyphenols including 26 isoflavones, 3 flavones, 2 flavanones, 2 aurones and a chalcone. All identifications were based upon UV spectra, mass spectral characteristics of protonated molecules, tandem mass spectral data, mass measurements obtained using a quadrupole time-of-flight mass spectrometer (QtofMS), and confirmed through the co-characterization of authentic compounds. In specific instances where the stereochemistry of sugar conjugates was uncertain, subsequent enzymatic hydrolysis of the conjugate followed by GC-MS was used to assign the sugar stereochemical configuration. Comparative metabolic profiling of Medicago truncatula root and cell cultures was then performed and revealed significant differences in the isoflavonoid composition of these two tissues.

Chemical and plant growth studies of Bacilli strains GB03 and IN937a revealed that the volatile components 2,3-butanediol and acetoin trigger plant growth promotion in Arabidopsis. Differences in growth promotion when cytokinin-signaling mutants are exposed to GB03 versus IN937a volatiles suggest a divergence in chemical signaling for these two bacterial strains. To provide a comprehensive chemical profile of bacterial volatiles emitted from these biologically active strains, headspace solid phase microextraction (SPME) coupled with software extraction of overlapping GC-separated components was employed. Ten volatile metabolites already reported from GB03 and IN937a were identified as well as 28 compounds not previously characterized. Most of the newly identified compounds were branched-chain alcohols released from IN937a, at much higher levels than in GB03. Principal component analysis clearly separated GB03 from IN937a, with GB03 producing higher amounts of 3-methyl-1-butanol, 2-methyl-1-butanol and butane-1-methoxy-3-methyl. The branched-chain alcohols share a similar functional motif to that of 2,3-butanediol and may afford alternative structural patterns for elicitors from bacterial sources.

In a study of Pacific Northwest plants of the Asteraceae family, a nor-ent-kaurane diterpene and a known diterpene, both displaying antibacterial activities, were isolated together with scopoletin and sitosterol-3-O-beta-glucopyranoside from the aerial parts of Antennaria geyeri. Anaphalis margaritacea afforded two hydroxylactones. The structures were established by one and two dimensional NMR techniques, IR and CIMS.

In response to insect feeding, tomato plants (Lycopersicon esculentum) release elevated levels of volatile organic compounds; that is, monoterpenes and sesquiterpenes are released both locally and systemically with wounding while C(6) green leaf volatiles are released only from damaged leaves. With the exogenous application (100 nmol) of the C(6)-tomato-volatile (E)-2-hexenal, an increase in the release of local and systemic terpenes was observed, while an equimolar amount of methyl jasmonate triggered only local emissions of terpenes. Labeling studies with 13CO(2) showed that de novo synthesis was not required for monoterpene or sesquiterpene release immediately following chemical treatment or insect feeding. Comparative measurements were made between aldehyde doses applied to the plant and levels naturally released from leaves with insect damage.