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Plants are chemical engineers par excellence. Collectively they make a vast array of structurally diverse specialized metabolites. The raw materials for building new pathways (genes encoding biosynthetic enzymes) are commonly recruited directly or indirectly from primary metabolism. Little is known about how new metabolic pathways and networks evolve in plants, or what key nodes contribute to branches that lead to the biosynthesis of diverse chemicals. Here we review the molecular mechanisms underlying the generation of biosynthetic branchpoints. We also consider examples in which new metabolites are formed through the joining of precursor molecules arising from different biosynthetic routes, a scenario that greatly increases both the diversity and complexity of specialized metabolism. Given the emerging importance of metabolic gene clustering in helping to identify new enzymes and pathways, we further cover the significance of biosynthetic gene clusters in relation to metabolic networks and dedicated biosynthetic pathways. In conclusion, an improved understanding of the branchpoints between metabolic pathways will be key in order to be able to predict and illustrate the complex structure of metabolic networks and to better understand the plasticity of plant metabolism. This article is part of the theme issue 'The evolution of plant metabolism'. [ABSTRACT FROM AUTHOR]

AbstractProcyanidins (PCs) have emerged as agents with potential antimicrobial and antibiofilm activities, although their mechanisms of action and structure–activity relationships remain poorly understood. This review assessed the potential mechanisms of action and applications of these compounds to explore these aspects. Studies on the antimicrobial properties of PCs suggest that they are involved in osmotic imbalance, DNA interactions and metabolic disruption. Although less studied, their antibiofilm activities include antiadhesive effects and the modulation of mobility and quorum sensing. However, most research has used uncharacterized plant extracts for in vitro assays, limiting the understanding of the structure–activity relationships of PCs and their in vivo mechanisms. Clinical trials on the antimicrobial and antibiofilm properties of PCs have not clarified these issues due to nonstandardized methodologies, inadequate chemical characterization, and the limited number of studies, preventing a consensus and evaluation of the in vivo effects. Additionally, patent analysis revealed that technological developments in the antimicrobial and antibiofilm uses of PCs are concentrated in health care and dental care, but new biotechnological uses are emerging. Therefore, while PCs are promising antimicrobial and antibiofilm compounds, further research into their chemical structures and mechanisms of action is crucial for evidence-based applications in biotechnology and health care. [ABSTRACT FROM AUTHOR]

Abstract Treatment of bacterial infections with antibiotic resistance is complicated. For this reason, new therapeutic methods are needed to control bacterial infections. Therefore, it is necessary to discover new antibiotics from medicinal plants that can destroy drug-resistant bacteria. Essential oils (EO) of some medicinal plants have antimicrobial effects and can be used as antimicrobial agents in the treatment of infections and food industries. The aim of this study was to determine the EO composition and antimicrobial effects of EO and polyphenols profile of Salvia Sahendica roots for the first time. Chemical compounds and antibacterial activity of EOs against Staphylococcus aureus and Bacillus cereus as gram-positive and Escherichia coli and Pseudomonas aeruginosa as gram- negative bacteria were evaluated using microtiter broth dilution method. Studied organs of S. sahendica showed significant diversity in terms of type and percentage of essential oil and polyphenol compounds. Overall, 44, 46, 42, and 45 compounds were identified in the essential oil of leaves, flowers, stems, and roots of this plant, which constituted 99.6, 99.3, 98.2, and 99.4% of total oil composition, respectively. The current study collectively demonstrated inhibitory effects ranged from strong (S. aureus) to low inhibition (P. aeruginosa). According to the HPLC result, the amounts of coumaric acid, chlorogenic acid, and gallic acid compounds in the root are higher than in other plant parts, which indicate that the root can be a suitable source for the production of these valuable polyphenol compounds. Due to the results, it is possible to hope for the application of EO from S. sahendica as natural antibacterial in the pharmaceutical and food industries.

Eplingiella fruticosa, popularly known as "alecrim-de-vaqueiro", is an aromatic and medicinal plant of the Lamiaceae family, endemic to the coastal region of northeastern Brazil. The objective of this study was to evaluate, in 12 genotypes of E. fruticosa, the variation of 16 morpho-agronomic markers related to the plant and leaves, as well as to identify the phytochemical compounds present in the essential oil (EO) of this species. The essential oil was obtained from dry leaves by hydrodistillation and analyzed by gas chromatograph coupled to mass spectrometer and a flame ionization detector (GC–MS/FID). The data were evaluated using multivariate analysis via the unweighted pair group method with arithmetic mean (UPGMA) for hierarchical clustering with canonical variables. Based on the morpho-agronomic data obtained, the formation of at least three groups was observed. The characteristics that most contributed to the formation of the groups were left petiole length, fresh leaf weight and leaf length. The genotypes EF002, EF003, EF005 and EF012 stood out by presenting greater genetic distances, indicating good potential for use in breeding programs aimed at foliar biomass production. A total 15 constituents were identified in the EOs, of which (E)-caryophyllene, bicyclogermacrene and α-pinene were the main components of all genotypes. Diversity classification based on chemical composition of EOs put them into groups. The highest detected components in the respective genotypes were: Group 1, represented by seven genotypes, containing (E)-caryophyllene (8.61–13.15%) and bicyclogermacrene (7.15–13.25%) as major compounds; Group 2, consisting of two genotypes, with (E)-caryophyllene (14.42–16.36%) and bicyclogermacrene (16.96–19.82%) as major compounds; Group 3, represented by two individuals, with highest production of (E)-caryophyllene (13.86–14.98%); and Group 4, with only one genotype, containing α-pinene (12.0%) as the major compound. The results of the present study can contribute to a better understanding and management of conservation and breeding of E. fruticosa germplasm. In addition, the results show the potential of the essential oils of this species and their major compounds for the development of new pharmaceutical products. [ABSTRACT FROM AUTHOR]

Tanacetum vulgare L., tansy, is a perennial plant with highly variable terpenoid composition, with mono‐ and sesquiterpenoids being the most abundant. The high diversity of terpenoids plays an important role in mediating ecological interactions. However, the distribution of terpenoids in different tissues and inducibility of terpenoids in these tissues via biotic stress are poorly understood. We investigated changes in terpenoid profiles and concentrations in different organs following treatment of roots with pipecolic acid (Pip), a non‐proteinogenic amino acid that triggers defence responses leading to induce systemic resistance (SAR) in plants. Tansy leaves and midribs contained mainly monoterpenoids, while coarse and fine roots contained mainly sesquiterpenoids. Rhizomes contained terpenoid profiles of both midribs and roots but also unique compounds. Treatment with Pip led to an increase in concentrations of mono‐ and sesquiterpenoids in all tissues except rhizomes. However, significantly more sesquiterpenoids was formed in root tissues in response to Pip treatment, compared to shoots. The metabolic atlas for terpenoids presented here shows that there is exceptionally strong differentiation of terpenoid patterns and terpenoid content in different tissues of tansy. This, together with differential inducibility by Pip, suggests that the chemical diversity of terpenoids may play an important role in tansy ecological interactions and defence against biotic stressors that feed on below‐ and aboveground organs. [ABSTRACT FROM AUTHOR]

Key message: Inventory and seasonal variation of terpene emissions from tropical trees in French Guiana: implications for environmental and ecological roles. A limited understanding of foliar terpene emissions from different tree species is prominent in diverse tropical forests. We conducted a study in French Guiana, screening BVOC emissions from 36 tropical woody species. We focused on 32 species in the dry season and 33 in the wet season, documenting terpene emissions for the first time in some of these tree species. Our findings show that 93.8% emitted terpenes in the dry season, while only 33.3% did so in the wet season. Terpene emissions ranged from 0.01 to 80.9 μg g−1 h−1 in the dry season and 0 to 11.7 μg g−1 h−1 in the wet season, consistent with previous reports. We identified and quantified 23 terpene compounds, including 19 monoterpenes and 4 sesquiterpenes. Additionally, 2 non-terpenoid compounds were detected: 2,2,4,6,6-pentamethylheptane (with no detected emissions in the dry season) and toluene. Among the monoterpenes, the most abundant were α-terpinolene, limonene, α-pinene, β-ocimene, and sabinene. As for sesquiterpenes, β-caryophyllene, α-caryophyllene, and α-copaene were observed during the dry season, while during the wet season, α-terpinolene predominated, followed by limonene, α-pinene, sabinene, β-caryophyllene, and α-copaene. Isoprene was detected in most of the species studied in both seasons. Sesquiterpene emissions displayed a notable phylogenetic pattern, whereas total terpenes and monoterpenes did not; however, total terpenes and monoterpenes exhibited a significant seasonal influence. Our study demonstrates that seasonality strongly influences BVOC production in tropical trees, with higher emissions in the dry season. These findings imply that various factors and conditions influence tree emissions in this tropical forest, affecting their ecological, environmental, and climatic roles, as well as the implementation of atmospheric chemistry models. [ABSTRACT FROM AUTHOR]

Intraspecific variation of specialized metabolites in plants, such as terpenoids, are used to determine chemotypes. Tansy Tanacetum vulgare exhibits diverse terpenoid profiles that affect insect communities. However, it is not fully known whether patterns of their chemical composition and associated insects vary beyond the community scale. Here, we investigated the geographic distribution of mono‐ and sesquiterpenoid chemotypes in tansy leaves and their relationships with specific insect communities across Germany. We sampled tansy leaves from ten plants with and five plants without aphids in each of 26 sites along a north–south and west–east transect in Germany. Hexane‐extracted metabolites from leaf tissues were analyzed by gas chromatography‐mass spectrometry (GC‐MS). Plant morphological traits, aphid occurrence and abundance, and occurrence of ants were recorded locally. The effect of plant chemotype, plant morphological parameters, and abiotic site parameters such as soil types, temperature and precipitation on insect occurrences were analyzed. Plants clustered into four monoterpenoid and four sesquiterpenoid chemotype classes. Monoterpene classes differed in their latitudinal distribution, whereas sesquiterpenes were more evenly distributed across the transect. Aphid and ant occurrence was influenced by monoterpenoids. Plants of monoterpenoid class 1 were colonized by aphids and ants significantly more often than expected by chance, whereas in other classes there were no significant differences. Aphid abundance was affected by soil type, and average annual temperature positively correlated with the occurrence of ants. We found significant geographic patterns in the distribution of tansy chemodiversity and show that monoterpenoids affect aphid and ant occurrence, while the soil type can influence aphid abundance. We show that geographic variation in plant chemistry influences insect community assembly on tansy plants. [ABSTRACT FROM AUTHOR]

3,4-bridged indoles are underrepresented among the vast number of indoles described in the literature. Attempts to access 3,4-macrocyclized indoles led to the unexpected formation of a novel tetracyclic indole through intramolecular acid-catalyzed ring contraction. The herein-established one-step synthetic route provides an excellent medicinal chemistry platform for the construction of screening libraries covering a unique chemical space of indoles. [ABSTRACT FROM AUTHOR]

Plants synthesize aromatic components during their secondary metabolism, these components are known as volatile oils or essential oils. Oils extracted from medicinal and aromatic plants have been investigated and applied due to their ethnomedicinal properties and the presence of abundant bioactive compounds. Many research studies examined the variations in the yield and composition of essential oil depending on the season and duration of the day-night period. The aim of the present study is twofold, we have performed a bibliometric analysis by using the Scopus database (data collection) and VOSviewer software (analysis) along with a comprehensive review of the literature published to date on the essential oils extracted from aromatic and medicinal plants, with an emphasis on their chemical profiles based on climatic and circadian periods. Extensive research on this relationship between abiotic factors (climatic and circadian) and chemical constituents, has identified significant variability among them. Phyto medicines and preparations with well-defined and verified bioactive volatile components, action mechanisms, and therapeutic potential of essential oils, have been utilized as pharmacological means. During this study, it was observed that this field is under-explored, and only limited data is available so far, therefore it has a lot of scope for future research. [ABSTRACT FROM AUTHOR]

Network pharmacology is an ideal tool to explore the effects of therapeutic components derived from plants on human metabolic diseases that are linked to inflammation. This study investigated the antioxidant effects of ginger leaves (GLs) and predicted targets for antioxidant activity. Quantitative and free radical scavenging analyses were performed to detect the main bioactive compounds of GLs and evaluate their antioxidant activities. Chemical diversity and network pharmacology approaches were used to predict key antioxidant components of GLs and their molecular targets. Nine major bioactive compounds of GLs were quantified using an internal standard method, and the antioxidant activity was evaluated using the DPPH and ABTS free radical scavenging methods. We first built the compound-gene-pathways and protein-protein interaction networks of GLs-related antioxidant targets and then conducted gene ontology and Kyoto Encyclopedia of Gene and Genome (KEGG) pathway enrichment analyses. Molecular docking results show that astragalin, a compound isolated from GLs, had the highest level of connectivity in the compound-target network and was involved in inflammation-related biosynthesis by directly impacting cytokine gene expression and PTGS2 inhibition markers. These findings not only suggest that the compounds isolated from GLs can be developed as potential antioxidants, but also demonstrate the applicability of network pharmacology to assess the potential of foods for disease treatment. [ABSTRACT FROM AUTHOR]

Ageratum conyzoides L., recognized globally as a noxious weed, holds significant value in traditional medicine, particularly in treating cuts, wounds, and tick infestations. This study focuses on identifying specific germplasms of this plant, rich in therapeutically valuable metabolites, across various phytogeographical zones in India. Using the Reverse Phase High-Performance Liquid Chromatography with Photodiode Array Detection (RP-HPLC-PDA) method, we analyzed 110 samples to quantify five key bioactive markers: Precocene-I (PRC-I), Coumarin (CM), Caryophyllene (CAR), Caryophyllene Oxide (CAO), and Humulene (HUM). Our findings revealed distinct geographical variations in these compounds. The highest concentrations of PRC-I (7.86±1.36 %) was found in sample NAC-12, CM (1.50±0.46 %) and HUM (0.0099±0.0004 %) in NAC-104, while CAR (6.33±0.87 %) and CAO (6.23±0.18 %) were predominant in NAC-01 and NAC-02, respectively. Ecological Niche Modelling (ENM) was used to predict the climatic suitability of regions for high yield of these metabolites. The ENM results showed that annual precipitation (Bio 12), precipitation of the coldest quarter (Bio 19) and minimum temperature of coldest month (Bio 6) were the principal climatic factors influencing metabolite content. Geographically, the Indo-Gangetic plain, Indus plain, and Central India were identified as suitable for higher content of PRC-I, CAO, CAR, whereas the North Eastern region favoured high content of CM and HUM. This study underscores the importance of bioactive marker-based assessment in understanding chemotypic diversity and demonstrates the effective use of ENM in predicting optimal habitats for harvesting specific chemotypes. These insights pave the way for location-specific cultivation strategies and targeted procurement of metabolite-rich germplasms, contributing to sustainable sourcing and conservation efforts, as well as to the advancement of herbal product standardization and efficacy. [Display omitted] • Five bioactive markers were quantified in 110 Ageratum conyzoides samples. • Precocene I was in maximum concentration followed by caryophyllene. • Central India region was favorable for precocene and caryophyllenes. • North Eastern region of India favoured high content of coumarin and humulene. [ABSTRACT FROM AUTHOR]

Summary: As a frequently consumed beverage worldwide, tea is rich in naturally important bioactive metabolites. Combining genetic, metabolomic and biochemical methodologies, here, we present a comprehensive study to dissect the chemical diversity in tea plant. A total of 2837 metabolites were identified at high‐resolution with 1098 of them being structurally annotated and 63 of them were structurally identified. Metabolite‐based genome‐wide association mapping identified 6199 and 7823 metabolic quantitative trait loci (mQTL) for 971 and 1254 compounds in young leaves (YL) and the third leaves (TL), respectively. The major mQTL (i.e., P < 1.05 × 10−5, and phenotypic variation explained (PVE) > 25%) were further interrogated. Through extensive annotation of the tea metabolome as well as network‐based analysis, this study broadens the understanding of tea metabolism and lays a solid foundation for revealing the natural variations in the chemical composition of the tea plant. Interestingly, we found that galloylations, rather than hydroxylations or glycosylations, were the largest class of conversions within the tea metabolome. The prevalence of galloylations in tea is unusual, as hydroxylations and glycosylations are typically the most prominent conversions of plant specialized metabolism. The biosynthetic pathway of flavonoids, which are one of the most featured metabolites in tea plant, was further refined with the identified metabolites. And we demonstrated the further mining and interpretation of our GWAS results by verifying two identified mQTL (including functional candidate genes CsUGTa, CsUGTb, and CsCCoAOMT) and completing the flavonoid biosynthetic pathway of the tea plant. [ABSTRACT FROM AUTHOR]

Host plant consumption and pathogen infection commonly influence insect traits related to development and immunity, which are ultimately reflected in the behavior and physiology of the insect. Herein, we explored changes in the metabolome of a generalist insect herbivore, Vanessa cardui (Lepidoptera: Nymphalidae), in response to both dietary variation and pathogen infection in order to gain insight into tritrophic interactions for insect metabolism and immunity. Caterpillars were reared on two different host plants, Plantago lanceolata (Plantaginaceae) and Taraxacum officinale (Asteraceae) and subjected to a viral infection by Junonia coenia densovirus (JcDV), along with assays to determine the insect immune response and development. Richness and diversity of plant and caterpillar metabolites were evaluated using a liquid chromatography-mass spectrometry approach and showed that viral infection induced changes to the chemical content of V. cardui hemolymph and frass dependent upon host plant consumption. Overall, the immune response as measured by phenoloxidase (PO) enzymatic activity was higher in individuals feeding on P. lanceolata compared with those feeding on T. officinale. Additionally, infection with JcDV caused suppression of PO activity, which was not host plant dependent. We conclude that viral infection combined with host plant consumption creates a unique chemical environment, particularly within the insect hemolymph. Whether and how these metabolites contribute to defense against viral infection is an open question in chemical ecology. [ABSTRACT FROM AUTHOR]

Diabetes mellitus is a chronic metabolic condition marked by high blood glucose levels caused by inadequate insulin synthesis or poor insulin use. This condition affects millions of individuals worldwide and is linked to a variety of consequences, including cardiovascular disease, neuropathy, nephropathy, and retinopathy. Diabetes therapy now focuses on controlling blood glucose levels through lifestyle changes, oral medicines, and insulin injections. However, these therapies have limits and may not successfully prevent or treat diabetic problems. Several marine-derived chemicals have previously demonstrated promising findings as possible antidiabetic medicines in preclinical investigations. Peptides, polyphenols, and polysaccharides extracted from seaweeds, sponges, and other marine species are among them. As a result, marine natural products have the potential to be a rich source of innovative multitargeted medications for diabetes prevention and treatment, as well as associated complications. Future research should focus on the chemical variety of marine creatures as well as the mechanisms of action of marine-derived chemicals in order to find new antidiabetic medicines and maximize their therapeutic potential. Based on preclinical investigations, this review focuses on the next step for seaweed applications as potential multitargeted medicines for diabetes, highlighting the bioactivities of seaweeds in the prevention and treatment of this illness. [ABSTRACT FROM AUTHOR]

Introduction: The plant essential oils are composed of volatile compounds and have significant value in preventing and treating neurological diseases, anxiety, depression, among others. The genus Salvia has been shown to be an important medicinal resource, especially the aerial parts of genus Salvia, which are rich in volatile compounds; however, the chemical diversity and distribution patterns of volatile compounds in Salvia species are still unknown. Objective: The work is performed to analyse the chemical diversity and distribution patterns of volatile compounds in genus Salvia. Methods: The genomic single nucleotide polymorphisms (SNPs) combined with gas chromatography–mass spectrometry (GC–MS) were used to explore the evolution and chemical diversity of Salvia volatile compounds. Initially, the genetic relationship of genus Salvia was revealed by phylogenetic tree that was constructed based on SNPs. And then, GC–MS was applied to explore the chemical diversity of volatile compounds. Results: The results indicated that the volatile compounds were mainly monoterpenoids, sesquiterpenoids, and aliphatic compounds. The genomic SNPs divided species involved in this work into four branches. The volatile compounds in the first and second branches were mainly sesquiterpenoids and monoterpenoids, respectively. Species in the third branch contained more aliphatic compounds and sesquiterpenoids. And those in the fourth branch were also rich in monoterpenoids but had relatively simple chemical compositions. Conclusion: This study offered new insights into the phylogenetic relationships besides chemistry diversity and distribution pattern of volatile compounds of genus Salvia, providing theoretical guidance for the investigations and development of secondary metabolites. The results indicated that the volatile compounds were mainly monoterpenoids, sesquiterpenoids, and aliphatic compounds. The genomic single nucleotide polymorphisms divided species involved in this work into four branches. The volatile compounds in the first and second branches were mainly sesquiterpenoids and monoterpenoids, respectively. Species in the third branch contained more aliphatic compounds and sesquiterpenoids. And those in the fourth branch were also rich in monoterpenoids but had relatively simple chemical compositions. [ABSTRACT FROM AUTHOR]

Abstract The aquatic networks that connect soils with oceans receive each year 5.1 Pg of terrestrial carbon to transport, bury and process. Stagnant sections of aquatic networks often become anoxic. Mineral surfaces attract specific components of organic carbon, which are released under anoxic conditions to the pool of dissolved organic matter (DOM). The impact of the anoxic release on DOM molecular composition and reactivity in inland waters is unknown. Here, we report concurrent release of iron and DOM in anoxic bottom waters of northern lakes, removing DOM from the protection of iron oxides and remobilizing previously buried carbon to the water column. The deprotected DOM appears to be highly reactive, terrestrially derived and molecularly distinct, generating an ambient DOM pool that relieves energetic constraints that are often assumed to limit carbon turnover in anoxic waters. The Fe-to-C stoichiometry during anoxic mobilization differs from that after oxic precipitation, suggesting that up to 21% of buried OM escapes a lake-internal release-precipitation cycle, and can instead be exported downstream. Although anoxic habitats are transient and comprise relatively small volumes of water on the landscape scale, our results show that they may play a major role in structuring the reactivity and molecular composition of DOM transiting through aquatic networks and reaching the oceans.

Terpenes are important mediators of plant chemical response to environmental cues. Here, we describe the genome-wide identification and biochemical characterization of TPS-a members in Medicago truncatula, a model legume crop. Genome mining identified thirty-nine full-length terpene synthases with a significant number predicted to produce monoterpenes and sesquiterpenes. Biochemical characterization of the TPS-a subfamily associated with sesquiterpene biosynthesis revealed such compounds, that exhibit substantial biological activity in other plants. Gene expression analysis using qPCR and the Medicago gene atlas illustrated distinct tissue and time-based variation in expression in leaves and roots. Together our work establishes the gene-tometabolite relationships for sesquiterpene synthases in M. truncatula. Understanding the biosynthetic capacity is a foundational step to defining the ecological roles of this important family of compounds. [ABSTRACT FROM AUTHOR]

The aquatic networks that connect soils with oceans receive each year 5.1 Pg of terrestrial carbon to transport, bury and process. Stagnant sections of aquatic networks often become anoxic. Mineral surfaces attract specific components of organic carbon, which are released under anoxic conditions to the pool of dissolved organic matter (DOM). The impact of the anoxic release on DOM molecular composition and reactivity in inland waters is unknown. Here, we report concurrent release of iron and DOM in anoxic bottom waters of northern lakes, removing DOM from the protection of iron oxides and remobilizing previously buried carbon to the water column. The deprotected DOM appears to be highly reactive, terrestrially derived and molecularly distinct, generating an ambient DOM pool that relieves energetic constraints that are often assumed to limit carbon turnover in anoxic waters. The Fe-to-C stoichiometry during anoxic mobilization differs from that after oxic precipitation, suggesting that up to 21% of buried OM escapes a lake-internal release-precipitation cycle, and can instead be exported downstream. Although anoxic habitats are transient and comprise relatively small volumes of water on the landscape scale, our results show that they may play a major role in structuring the reactivity and molecular composition of DOM transiting through aquatic networks and reaching the oceans. [ABSTRACT FROM AUTHOR]

A comprehensive study was conducted on the diversity and characteristics of five Thymus species native to Hungary, concerning frequency of occurrence, habitat preferences, essential oil content of the dried flowering shoots, and chemotype patterns determined by GC/MS. Our main aims were to provide an overview of the essential oil diversity of thyme resources and select the best genotypes with potential for cultivation and utilization. Based on the results obtained in 74 populations of 63 localities belonging to 15 regions of the Transdanubian and Northern Hungarian Mountains, considerable essential oil diversity was found. Thymus pannonicus (TPA), of generalist character, was proven to be the most frequent species (38 populations), while T. serpyllum (TSE) occurred only in two habitats. High average amounts of essential oil (EO) were shown for T. pannonicus (0.46 mL/100 g DW), T. pulegioides (TPU: 0.47 mL/100 g DW), and T. serpyllum (0.59 mL/100 g DW), while low EO accumulating ability was detected in T. glabrescens (TGL: 0.26 mL/100 g DW) and in T. praecox (TPR: 0.10 mL/100 g DW). In general, the thymol chemotype was the most frequent (34 populations), found together with the related molecules (p-cymene: 26; γ-terpinene: 15), while numerous other monoterpenes (M: geraniol: 12, linalool: 7) or sesquiterpenes (S: germacrene D: 25, β-caryophyllene: 21) were dominant, as well as combined (MS) chemotypes, which were also described in the Eos of Thymus species in Hungary. Our findings confirmed that T. pannonicus shows potential for cultivation with homogenous drug quality, adequate amounts of essential oil, and stability in EO composition. Data from original habitats also supports its high tolerance and adaptability to diverse environmental conditions, which is advantageous when facing climate change and extremities. [ABSTRACT FROM AUTHOR]

Cicerbita alpina (L.) Wallr, is a perennial alpine plant and a member of the Asteraceae family, typically found at altitudes above 1000 meters in the Italian Alps. Although previously utilized primarily as a local delicacy, recent studies have revealed strong antiparasitic activity through in vitro experiments. In Europe, numerous chemical drugs employed to combat nematodes — helminths that infest the digestive tract of livestock — are banned due to their environmental harm or show only reduced efficiency because of the development of resistance. Consequently, there is a growing demand for new alternative anthelmintic treatments in agricultural practices. Specialized metabolites found in the extracts of C. alpina could offer a sustainable and biological alternative to chemical drugs, specifically for nematode control. For this purpose, a unique germplasm collection originating from eight distinct natural populations in the Italian Alps was analyzed for its chemical diversity using state-of-the-art targeted LC-MS/MS spectrometry, including quantification based on multiple reaction monitoring. The predominant metabolites identified from the species were the caffeic acid derivatives chicoric acid, chlorogenic acid, and 3. 5-dicaffeoylquinic acid, the sesquiterpene lactone derivative 8-O-acetyl-15-ß-D-glucopyranosyl lactucin and the flavone glycosides, apigenin-7-O-glucoside and luteolin-7-Oglucoside, alongside their precursors apigenin and luteolin, respectively. Additionally, the genetic diversity of eighty individual plants within the germplasm collection was evaluated using ten DNA molecular markers (Simple Sequence Repeats), successfully transferred from two closely related species (Cichorium intybus and Tanacetum parthenium). This investigation unveiled a significant range of genetic diversity within the examined populations, resulting in the establishment of three distinct genetic groups. The findings were further correlated with the original ecological environment and local climate conditions spanning a biennial period, indicating substantial variations among the different accessions and the intricate interplay between genetic background and environmental factors. These results could serve as a basis for future domestication of the species through plant breeding programs ensuring product quality, but also facilitating the cultivation of C. alpina in more diverse geographic regions. [ABSTRACT FROM AUTHOR]

Cnidium monnieri (L.) Cusson, a widely distributed plant, has been used in traditional Chinese medicine for a long time. For its medicinal values reflected by chemical variation, researches on high-performance liquid chromatographic (HPLC) fingerprinting and molecular markers of chloroplast DNA (cpDNA) were carried out. In the research, we analyzed the chemical composition qualitatively and quantitatively, and amplified the fragment of trnL-trnF and trnS-trnG in C. monnieri from twelve populations throughout the known distributions in China to make a better understanding of the chemical variance and evolutionary history and to reveal the genetic mechanism of the chemical variance in C. monnieri. The results suggested chemical variance and high genetic diversity with a significant phylogeographical pattern (NST > GST, P > 0.05), which showed restricted gene flow among the populations and significant geographical or environmental isolation. Climatic difference might play a key role in the present distribution of the species, resulting the chemical variance in the C. monnieri. These findings not only provide some references for evaluating the medicinal quality and selecting C. monnieri (L.) Cusson with good pharmacological properties, but also elucidate the evolutionary history of this medicinal herb and provide guidance for the methods of resource conservation. [ABSTRACT FROM AUTHOR]

Stony coral symbiotic fungi were used to investigate the effects of different culture conditions on the anti‑inflammatory activities and chemical diversities of their secondary metabolites. Based on the OSMAC (one stain many compounds) strategy, 31 strains of stony coral‑derived symbiotic fungi were cultured in small‑scale fermentation with potato dextrose broth (PDB) and brown rice medium at three salinities (0.3%, 3.0%, and 10.0%), respectively. Lipopolysaccharide (LPS) ‑induced BV‑2 microglia were used as the inflammation model, from which the strains with anti‑inflammatory activity were selected. Via thin‑layer chromatography (TLC),ultra‑performance liquid chromatography quadrupole time‑of‑flight mass spectrometry (UPLC‑QTOF‑MS) and feature‑based molecular networking (FBMN), the chemical diversity of the secondary metabolites from the anti‑inflammatory active strains was further analyzed. The results showed that five strains demonstrated significant anti‑inflammatory activity under the brown rice medium conditions and showed moderate or strong inhibitory activity against LPS‑ induced nitric oxide (NO) release in BV‑2 cells, with a significant concentration‑dose dependence. While the crude extract of strain C3‑9 also showed the significant inhibition to NO production at low concentrations of 10 and 20 μg/mL, further TLC and FBMN analyses revealed that the secondary metabolites of strain C3‑9 were rich in anti‑inflammatory compounds and highly diverse. The secondary metabolites of the stony coral co‑epiphytic fungus C3‑9 have significant anti‑inflammatory activity and diversity, providing a basis for the subsequent discovery of anti‑ inflammatory active compounds. [ABSTRACT FROM AUTHOR]

3,4-bridged indoles are underrepresented among the vast number of indoles described in the literature. Attempts to access 3,4-macrocyclized indoles led to the unexpected formation of a novel tetracyclic indole through intramolecular acid-catalyzed ring contraction. The herein-established one-step synthetic route provides an excellent medicinal chemistry platform for the construction of screening libraries covering a unique chemical space of indoles.

Cytochrome P450s (CYPs) are the most prominent family of enzymes involved in NADPH- and O2-dependent hydroxylation processes throughout all spheres of life. CYPs are crucial for the detoxification of xenobiotics in plants, insects, and other organisms. In addition to performing this function, CYPs serve as flexible catalysts and are essential for producing secondary metabolites, antioxidants, and phytohormones in higher plants. Numerous biotic and abiotic stresses frequently affect the growth and development of plants. They cause a dramatic decrease in crop yield and a deterioration in crop quality. Plants protect themselves against these stresses through different mechanisms, which are accomplished by the active participation of CYPs in several biosynthetic and detoxifying pathways. There are immense potentialities for using CYPs as a candidate for developing agricultural crop species resistant to biotic and abiotic stressors. This review provides an overview of the plant CYP families and their functions to plant secondary metabolite production and defense against different biotic and abiotic stresses.

Abstract Background Wild fenugreek (Trigonella monantha), a multi-purpose annual plant, has traditionally been used as a food, forage, and medicinal plant. However, the knowledge of the diversity of its chemical characteristics is limited. In this study, 40 wild fenugreek ecotypes collected from their natural habitats in Iran and grown together in field conditions, were analyzed for their seed chemical properties. Results The ecotypes were cultivated in a randomized complete block design (RCBD) with three replications. The results of ANOVA revealed a significant difference among the ecotypes for all measured characters (P

Terpenes are important mediators of plant chemical response to environmental cues. Here, we describe the genome-wide identification and biochemical characterization of TPS-a members in Medicago truncatula, a model legume crop. Genome mining identified thirty-nine full-length terpene synthases with a significant number predicted to produce monoterpenes and sesquiterpenes. Biochemical characterization of the TPS-a subfamily associated with sesquiterpene biosynthesis revealed such compounds, that exhibit substantial biological activity in other plants. Gene expression analysis using qPCR and the Medicago gene atlas illustrated distinct tissue and time-based variation in expression in leaves and roots. Together our work establishes the gene-to-metabolite relationships for sesquiterpene synthases in M. truncatula. Understanding the biosynthetic capacity is a foundational step to defining the ecological roles of this important family of compounds.

Plant and soil biodiversity can have significant effects on herbivore resistance mediated by plant metabolites. Here, we disentangled the independent effects of plant diversity and soil legacy on constitutive and herbivore‐induced plant metabolomes of three plant species in two complementary microcosm experiments. First, we grew plants in sterile soil with three different plant diversity levels. Second, single plant species were grown on soil with different plant diversity‐induced soil legacies. We infested a subset of all plants with Spodoptera exigua larvae, a generalist leaf‐chewing herbivore, and assessed foliar and root metabolomes. Neither plant diversity nor soil legacy had significant effects on overall foliar, root, or herbivore‐induced metabolome composition. Herbivore‐induced metabolomes, however, differed from those of control plants. We detected 139 significantly regulated metabolites by comparing plants grown in monocultures with conspecifics growing in plant or soil legacy mixtures. Moreover, plant–plant and plant–soil interactions regulated 141 metabolites in herbivore‐induced plants. Taken together, plant diversity and soil legacy independently alter the concentration and induction of plant metabolites, thus affecting the plant's defensive capability. This is a first step toward disentangling plant and soil biodiversity effects on herbivore resistance, thereby improving our understanding of the mechanisms that govern ecosystem functioning. [ABSTRACT FROM AUTHOR]

The chemical diversity of scleractinian corals is closely related to their physiological, ecological, and evolutionary status, and can be influenced by both genetic background and environmental variables. To investigate intraspecific variation in the metabolites of these corals, the metabolomes of four species (Pocillopora meandrina, Seriatopora hystrix, Acropora formosa, and Fungia fungites) from the South China Sea were analyzed using untargeted mass spectrometry-based metabolomics. The results showed that a variety of metabolites, including amino acids, peptides, lipids, and other small molecules, were differentially distributed among the four species, leading to their significant separation in principal component analysis and hierarchical clustering plots. The higher content of storage lipids in branching corals (P. meandrina, S. hystrix, and A. formosa) compared to the solitary coral (F. fungites) may be due to the high densities of zooxanthellae in their tissues. The high content of aromatic amino acids in P. meandrina may help the coral protect against ultraviolet damage and promote growth in shallow seawater, while nitrogen-rich compounds may enable S. hystrix to survive in various challenging environments. The metabolites enriched in F. fungites, including amino acids, dipeptides, phospholipids, and other small molecules, may be related to the composition of the coral's mucus and its life-history, such as its ability to move freely and live solitarily. Studying the chemical diversity of scleractinian corals not only provides insight into their environmental adaptation, but also holds potential for the chemotaxonomy of corals and the discovery of novel bioactive natural products. [ABSTRACT FROM AUTHOR]

Post-introduction evolution of plant defense traits is fundamental to several important theories for plant invasiveness. Research on chemical defense traits of invasive plants has focused mostly on targeted chemical analysis, however, such analyses restrict novel insights to known compounds. Here, we provide an untargeted metabolomic analysis of native and invasive Purple Loosestrife populations and we experimentally test if admixture between introduced populations provides a basis for rapid defense chemistry evolution. Invasive populations showed improved growth and generalist herbivore resistance, but lower resistance to a specialist weevil, consistent with the Shifting Defense Hypothesis of plant invasions. Metabolomic profiling revealed large shifts in chemistry between native and invasive populations, including differences in alkaloids and flavonoids. Experimental admixture increased chemical diversity and plant growth in the native populations, indicating its potential to fuel rapid evolution, but admixture did not affect generalist and specialist herbivory. Our untargeted metabolomics analysis provides novel insights in the evolutionary changes in the chemistry of invasive plants, and reveals the chemical associations of a shift from defenses against specialist to generalist herbivores in invasive populations. [ABSTRACT FROM AUTHOR]

Cytochrome P450s (CYPs) are the most prominent family of enzymes involved in NADPH- and O2-dependent hydroxylation processes throughout all spheres of life. CYPs are crucial for the detoxification of xenobiotics in plants, insects, and other organisms. In addition to performing this function, CYPs serve as flexible catalysts and are essential for producing secondary metabolites, antioxidants, and phytohormones in higher plants. Numerous biotic and abiotic stresses frequently affect the growth and development of plants. They cause a dramatic decrease in crop yield and a deterioration in crop quality. Plants protect themselves against these stresses through different mechanisms, which are accomplished by the active participation of CYPs in several biosynthetic and detoxifying pathways. There are immense potentialities for using CYPs as a candidate for developing agricultural crop species resistant to biotic and abiotic stressors. This review provides an overview of the plant CYP families and their functions to plant secondary metabolite production and defense against different biotic and abiotic stresses. [ABSTRACT FROM AUTHOR]

Plant species show large variation in the composition and content of their tannins and other polyphenols. These large metabolites are not easy to measure accurately, but they are important factors for species bioactivity and chemotaxonomy. Here, we used an automated group-specific UHPLC-DAD-MS/MS tool to detect and quantify eight most common polyphenol groups in 31 chemically diverse plant species representing many types of growth forms and evolutionary ages. Ten replicate plants were used for each species and two polyphenol-related bioactivities, i.e., protein precipitation capacity and oxidative activity were measured in all samples as well. By the help of a novel 2D fingerprint mapping tool we were able to visualize the qualitative and quantitative differences between the species in hydrolysable tannins (galloyl and hexahydroxydiphenoyl derivatives), proanthocyanidins (procyanidins and prodelphinidins), flavonols (kaempferol, quercetin and myricetin derivatives) and quinic acid derivatives together with the two bioactivities. The highest oxidative activities were found with species containing ellagitannins (e.g., Quercus robur, Geranium sylvaticum, Lythrum salicaria and Chamaenerion angustifolium) or prodelphinidin-rich proanthocyanidins (e.g., Ribes alpinum, Salix phylicifolia and Lysimachia vulgaris). The best species with high protein precipitation capacity were rich in gallotannins (Acer platanoides and Paeonia lactiflora) or oligomeric ellagitannins (e.g., Comarum palustre, Lythrum salicaria and Chamaenerion angustifolium). These types of tools could prove their use in many types of screening experiments and might reveal even unusually active polyphenol types directly from the crude plant extracts. [ABSTRACT FROM AUTHOR]

Premise: The scents of volatile organic compounds (VOCs) are an important component of ripe fleshy fruit attractiveness, yet their variation across closely related wild species is poorly understood. Phylogenetic patterns in these compounds and their biosynthetic pathways offer insight into the evolutionary drivers of fruit diversity, including whether scent can communicate an honest signal of nutrient content to animal dispersers. We assessed ripe fruit VOC content across the tomato clade (Solanum sect. Lycopersicon), with implications for crop improvement since these compounds are key components of tomato flavor. Methods: We analyzed ripe fruit volatiles from 13 species of wild tomato grown in a common garden. Interspecific variations in 66 compounds and their biosynthetic pathways were assessed in 32 accessions, and an accession‐level phylogeny was constructed to account for relatedness. Results: Wild tomato species can be differentiated by their VOCs, with Solanum pennellii notably distinct. Phylogenetic conservatism exists to a limited extent. Major cladewide patterns corresponded to divergence of the five brightly colored‐fruited species from the nine green‐fruited species, particularly for nitrogen‐containing compounds (higher in colored‐fruited) and esters (higher in green‐fruited), the latter appearing to signal a sugar reward. Conclusions: We established a framework for fruit scent evolution studies in a crop wild relative system, showing that each species in the tomato clade has a unique VOC profile. Differences between color groups align with fruit syndromes that could be driven by selection from frugivores. The evolution of colored fruits was accompanied by changes in biosynthetic pathways for esters and nitrogen‐containing compounds, volatiles important to tomato flavor. [ABSTRACT FROM AUTHOR]

Despite the first-order importance of crystallisation–differentiation for arc magma evolution, several other processes contribute to their compositional diversity. Among them is the remelting of partly crystallised magmas, also known as cumulate melting or 'petrological cannibalism'. The impact of this process on the plutonic record is poorly constrained. We investigate a nepheline-normative dyke suite close to the Blumone gabbros, a large amphibole-gabbro unit of the Tertiary Southern Alpine Adamello igneous complex. The compositions of the studied dykes are characterised by low SiO2 (43–46 wt. %), MgO (5.0–7.2 wt. %), Ni (18–40 μg/g), and high Al2O3 (20.2–22.0 wt. %) contents. Phenocrystic plagioclase in these dykes exhibits major, trace, and Sr isotope compositions similar to Blumone cumulate plagioclase, suggesting a genetic link between the nepheline-normative dykes and the amphibole-gabbro cumulates. We tested this hypothesis by performing saturation experiments on a nepheline-normative dyke composition in an externally heated pressure vessel at 200 MPa between 975 and 1100 °C at fO2 conditions close to the Ni–NiO buffer. Plagioclase and spinel are near-liquidus phases at and above 1050 °C, contrasting with the typical near-liquidus olivine ± spinel assemblage in hydrous calc-alkaline basalts. The alkaline nature of the dykes results from the abundance of amphibole in the protolith, consistent with melting of amphibole-gabbro cumulates. We modelled the heat budget from the repeated injection of basaltic andesite into a partly crystallised amphibole-gabbro cumulate. The results of this model show that no more than 7% of the cumulate pile reaches temperatures high enough to produce nepheline-normative melts. We propose that such nepheline-normative dykes are a hallmark of hydrous cumulate melting in subvolcanic plumbing systems. Therefore, ne-normative dykes in arc batholiths may indicate periods with high magma fluxes. [ABSTRACT FROM AUTHOR]

Network pharmacology is an ideal tool to explore the effects of therapeutic components derived from plants on human metabolic diseases that are linked to inflammation. This study investigated the antioxidant effects of ginger leaves (GLs) and predicted targets for antioxidant activity. Quantitative and free radical scavenging analyses were performed to detect the main bioactive compounds of GLs and evaluate their antioxidant activities. Chemical diversity and network pharmacology approaches were used to predict key antioxidant components of GLs and their molecular targets. Nine major bioactive compounds of GLs were quantified using an internal standard method, and the antioxidant activity was evaluated using the DPPH and ABTS free radical scavenging methods. We first built the compound-gene-pathways and protein-protein interaction networks of GLs-related antioxidant targets and then conducted gene ontology and Kyoto Encyclopedia of Gene and Genome (KEGG) pathway enrichment analyses. Molecular docking results show that astragalin, a compound isolated from GLs, had the highest level of connectivity in the compound-target network and was involved in inflammation-related biosynthesis by directly impacting cytokine gene expression and PTGS2 inhibition markers. These findings not only suggest that the compounds isolated from GLs can be developed as potential antioxidants, but also demonstrate the applicability of network pharmacology to assess the potential of foods for disease treatment.

Abstract Plant and soil biodiversity can have significant effects on herbivore resistance mediated by plant metabolites. Here, we disentangled the independent effects of plant diversity and soil legacy on constitutive and herbivore‐induced plant metabolomes of three plant species in two complementary microcosm experiments. First, we grew plants in sterile soil with three different plant diversity levels. Second, single plant species were grown on soil with different plant diversity‐induced soil legacies. We infested a subset of all plants with Spodoptera exigua larvae, a generalist leaf‐chewing herbivore, and assessed foliar and root metabolomes. Neither plant diversity nor soil legacy had significant effects on overall foliar, root, or herbivore‐induced metabolome composition. Herbivore‐induced metabolomes, however, differed from those of control plants. We detected 139 significantly regulated metabolites by comparing plants grown in monocultures with conspecifics growing in plant or soil legacy mixtures. Moreover, plant–plant and plant–soil interactions regulated 141 metabolites in herbivore‐induced plants. Taken together, plant diversity and soil legacy independently alter the concentration and induction of plant metabolites, thus affecting the plant's defensive capability. This is a first step toward disentangling plant and soil biodiversity effects on herbivore resistance, thereby improving our understanding of the mechanisms that govern ecosystem functioning.

Cicerbita alpina (L.) Wallr, is a perennial alpine plant and a member of the Asteraceae family, typically found at altitudes above 1000 meters in the Italian Alps. Although previously utilized primarily as a local delicacy, recent studies have revealed strong antiparasitic activity through in vitro experiments. In Europe, numerous chemical drugs employed to combat nematodes — helminths that infest the digestive tract of livestock — are banned due to their environmental harm or show only reduced efficiency because of the development of resistance. Consequently, there is a growing demand for new alternative anthelmintic treatments in agricultural practices. Specialized metabolites found in the extracts of C. alpina could offer a sustainable and biological alternative to chemical drugs, specifically for nematode control. For this purpose, a unique germplasm collection originating from eight distinct natural populations in the Italian Alps was analyzed for its chemical diversity using state-of-the-art targeted LC-MS/MS spectrometry, including quantification based on multiple reaction monitoring. The predominant metabolites identified from the species were the caffeic acid derivatives chicoric acid, chlorogenic acid, and 3. 5-dicaffeoylquinic acid, the sesquiterpene lactone derivative 8-O-acetyl-15-ß-D-glucopyranosyl lactucin and the flavone glycosides, apigenin-7-O-glucoside and luteolin-7-O-glucoside, alongside their precursors apigenin and luteolin, respectively. Additionally, the genetic diversity of eighty individual plants within the germplasm collection was evaluated using ten DNA molecular markers (Simple Sequence Repeats), successfully transferred from two closely related species (Cichorium intybus and Tanacetum parthenium). This investigation unveiled a significant range of genetic diversity within the examined populations, resulting in the establishment of three distinct genetic groups. The findings were further correlated with the original ecological environment and local climate conditions spanning a biennial period, indicating substantial variations among the different accessions and the intricate interplay between genetic background and environmental factors. These results could serve as a basis for future domestication of the species through plant breeding programs ensuring product quality, but also facilitating the cultivation of C. alpina in more diverse geographic regions.

Objectives: The ocean is a huge ecosystem with diverse marine life. Scientists have found a large number of natural products with unique structural features and excellent biological activity from these organisms. Marine-derived sulphur-containing alkaloids are a significant family of natural products with diverse structures and bioactivities. In this paper, the chemical and biological diversity of 972 sulfur-containing alkaloids derived from marine organisms reported from 1982 to 2022 were reviewed, and the structure–activity relationship was briefly analyzed, in order to provide reference for the discovery, synthesis, biological activity research and drug development of such compounds. Key findings: A total of 972 marine-derived sulphur-containing alkaloids have been collected. Among them, 80.36% of sulphur-containing alkaloids are from marine sponges, fungi, tunicates and bacteria. Moreover, cytotoxicity is their most significant property, About 1/3 sulphur-containing organisms are reported to be cytotoxic. Aming them, discorhabdins, curacins, tanjungides, leptosins, and latrunculins exhibit better cytotoxicity. In addition, the structure–activity relationships of the cytotoxicity of these compounds have been summarized for further investigation. Summary: In this paper, the chemical and bioactivity diversity of marine-derived sulphur-containing alkaloids were reviewed, which are a significant family of natural products with diverse structures and bioactivities. 972 sulphur-containing alkaloids were obtained from marine algae, sponges, cnidarians, tunicates, echinoderms, molluscs, bryozoans, dinoflagellates, cyanobacteria, bacteria and fungi, which possessed a wide spectrum of pharmacology including cytotoxicity, antibacterial, antifungal, antimitotic, antiviral, and other activities.

Cannabis sativa L. is a plant with a wide range of potential medicinal applications. In recent years, polyploidy has gained attention as a potential strategy for rapidly improving C. sativa, which, unlike other modern crops, has not yet benefitted from this established biotechnological application. Currently, no reports on high THCA and CBDA drug-type polyploid cultivars have been published. Moreover, it still needs to be clarified if different cultivars react similarly to polyploidization. For these reasons, we set out to evaluate and compare the phenotype and chemotype of three high Δ9-tetrahydrocannabinolic acid (THCA) and one high cannabidiolic acid (CBDA) drug-type cultivars in their diploid, triploid and tetraploid state through agronomic and metabolomic approaches. Our observations on plant morphology revealed a significant increase in plant height and leaf size with increasing ploidy levels in a cultivar-dependent manner. In contrast, cannabinoids were negatively affected by polyploidization, with the concentration of total cannabinoids, THCA, CBDA and cannabigerolic acid (CBGA) decreasing significantly in higher ploidy levels across all four cultivars. Headspace analysis of volatiles revealed that total volatile content decreased in triploids. On the other hand, tetraploids reacted differently depending on the cultivars. Two THCA dominant cultivars showed an increase in concentrations, while in the other two cultivars, concentrations decreased. Additionally, several rare compounds not present in diploids appeared in higher ploidy levels. Moreover, in one high THCA cultivar, a couple of elite tetraploid genotypes for cannabinoid and volatile production were identified, highlighting the role of cultivar and genotypic variability as an important factor in Cannabis sativa L. polyploids. Overall, our observations on plant morphology align with the giga phenotype observed in polyploids of other plant species. The decrease in cannabinoids and volatiles production in triploids have relevant implications regarding their commercial use. On the other hand, this study found that tetraploidization is a suitable approach to improve Cannabis sativa L. medicinal potential, although the response is cultivar and genotype-dependent. This work lays the ground for further improving, evaluating and harnessing Cannabis sativa L. chemical diversity by the breeding, biotechnological and pharmaceutical sectors. [ABSTRACT FROM AUTHOR]

Hemp (Cannabis sativa L.) is a widely researched industrial crop with a variety of applications in the pharmaceutical, nutraceutical, food, cosmetic, textile, and materials industries. Although many of these applications are related to its chemical composition, the chemical diversity of the hemp metabolome has not been explored in detail and new metabolites with unknown properties are likely to be discovered. In the current study, we explored the chemical diversity of the hemp seed metabolome through an untargeted metabolomic study of 52 germplasm accessions to 1) identify new metabolites and 2) link the presence of biologically important molecules to specific accessions on which to focus on in future studies. Multivariate analysis of mass spectral data demonstrated large variability of the polar chemistry profile between accessions. Five main groups were annotated based on their similar metabolic fingerprints. The investigation also led to the discovery of a new compound and four structural analogues, belonging to a previously unknown chemical class in hemp seeds: cinnamic acid glycosyl sulphates. Although variability in the fatty acid profiles was not as marked as the polar components, some accessions had a higher yield of fatty acids, and variation in the ratio of linoleic acid to a-linolenic acid was also observed, with some varieties closer to 3:1 (reported as optimal for human nutrition). We found that that cinnamic acid amides and lignanamides, the main chemical classes of bioactive metabolites in hemp seed, were more concentrated in the Spanish accession Kongo Hanf (CAN58) and the French accession CAN37, while the Italian cultivar Eletta Campana (CAN48) demonstrated the greatest yield of fatty acids. Our results indicate that the high variability of bioactive and novel metabolites across the studied hemp seed accessions may influence claims associated with their commercialization and inform breeding programs in cultivar development. [ABSTRACT FROM AUTHOR]

Enzymatic terpene functionalization is an essential part of plant secondary metabolite diversity. Within this, multiple terpene-modifying enzymes are required to enable the chemical diversity of volatile compounds essential in plant communication and defense. This work sheds light on the differentially transcribed genes within Caryopteris × clandonensis that are capable of functionalizing cyclic terpene scaffolds, which are the product of terpene cyclase action. The available genomic reference was subjected to further improvements to provide a comprehensive basis, where the number of contigs was minimized. RNA-Seq data of six cultivars, Dark Knight, Grand Bleu, Good as Gold, Hint of Gold, Pink Perfection, and Sunny Blue, were mapped on the reference, and their distinct transcription profile investigated. Within this data resource, we detected interesting variations and additionally genes with high and low transcript abundancies in leaves of Caryopteris × clandonensis related to terpene functionalization. As previously described, different cultivars vary in their modification of monoterpenes, especially limonene, resulting in different limonene-derived molecules. This study focuses on predicting the cytochrome p450 enzymes underlying this varied transcription pattern between investigated samples. Thus, making them a reasonable explanation for terpenoid differences between these plants. Furthermore, these data provide the basis for functional assays and the verification of putative enzyme activities. [ABSTRACT FROM AUTHOR]

Marine algal-derived endophytic fungi (MAEF) have proven to be unabated sources of novel secondary metabolites with remarkable scaffold diversity, structural complexity, and significant bioactivity. The growing trend in the discovery of new secondary metabolites from MAEF has continued increasing over the last few years. Our previous review summarized a total of 182 secondary metabolites isolated from MAEF covering from 2002 to mid-2015. To update the latest studies of intriguing secondary metabolites of MAEF, this present review covered 196 newly-discovered metabolites of MAEF from the beginning of 2016 to the end of 2021, which were categorized into terpenes and steroids (including bisabolane-type sesquiterpenes, cyclonerane-type sesquiterpenes, diterpenes, sesterterpenes, meroterpenoids, and steroids), nitrogenated compounds (including diketopiperazines, peptides, and other N-containing compounds), polyketides (including azaphilones, tetramic acid derivatives, chromenes, and chromone derivatives), phenolic compounds, and carboxylic acids derivatives based on their putative biogenetic origins. Crucial insights into their chemical diversity and biological activities are provided herein. [ABSTRACT FROM AUTHOR]

Plants produce diverse chemical defenses with contrasting effects on different insect herbivores. Deploying herbivore‐specific responses can help plants increase their defensive efficiency. Here, we explore how variation in induced plant responses correlates with herbivore species, order, feeding guild, and level of specialization. In a greenhouse experiment, we exposed 149 plants of Salix fragilis (Linnaeus, 1753) to 22 herbivore species naturally associated with this host. The insects belonged to four orders (Coleoptera, Lepidoptera, Hemiptera, and Hymenoptera), three feeding guilds (external leaf‐chewers, leaf‐tying chewers, and sap‐sucking), and included both dietary specialists and generalists. Following herbivory, we quantified induced changes in volatiles and nonvolatile leaf metabolites. We performed multivariate analyses to assess the correlation between herbivore order, feeding guild, dietary specialization, chewing damage by herbivores, and induced responses. The volatile composition was best explained by chewing damage and insect order, with Coleoptera and Lepidoptera eliciting significantly different responses. Furthermore, we recorded significant differences in elicited volatiles among some species within the two orders. Variation in nonvolatile leaf metabolites was mainly explained by the presence of insects, as plants exposed to herbivores showed significantly different metabolites from controls. Herbivore order also played a role to some extent, with beetles eliciting different responses than other herbivores. The induction of volatile and nonvolatile leaf metabolites shows different levels of specificity. The specificity in volatiles could potentially serve as an important cue to specialized predators or parasitoids, increasing the efficacy of volatiles as indirect defenses. By contrast, the induction of nonvolatile leaf metabolites was largely unaffected by herbivore identity. Most nonvolatile metabolites were downregulated, possibly indicating that plants redirected their resources from leaves in response to herbivory. Our results demonstrate how diverse responses to herbivores can contribute to the diversity of plant defensive strategies. [ABSTRACT FROM AUTHOR]