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Plants harbour a great chemodiversity, that is diversity of specialised metabolites (SMs), at different scales. For instance, individuals can produce a large number of SMs, and populations can differ in their metabolite composition. Given the ecological and economic importance of plant chemodiversity, it is important to understand how it arises and is maintained over evolutionary time. For other dimensions of biodiversity, that is species diversity and genetic diversity, quantitative models play an important role in addressing such questions. Here, we provide a synthesis of existing hypotheses and quantitative models, that is mathematical models and computer simulations, for the evolution of plant chemodiversity. We describe each model's ingredients, that is the biological processes that shape chemodiversity, the scales it considers and whether it has been formalized as a quantitative model. Although we identify several quantitative models, not all are dynamic and many influential models have remained verbal. To fill these gaps, we outline our vision for the future of chemodiversity modelling. We identify quantitative models used for genetic variation that may be adapted for chemodiversity, and we present a flexible framework for the creation of individual-based models that address different scales of chemodiversity and combine different ingredients that bring this chemodiversity about., (© 2024 The Authors. Ecology Letters published by John Wiley & Sons Ltd.)

Several large-scale metabolic profiling studies have been directed to prospect crops with a major focus on yield-related traits and, ultimately, with the definition of specific markers for plant selection in breeding programs. However, some of these technologies are expensive, time-consuming and not easily feasible for a quick approach. Fatty acid profiling was described as reliable biomarkers and as a chemotaxonomic tool allowing to study not only the diversity in germplasm collections but also to discriminate their geographic origin. We have used fatty acids profiling for a preliminary assessment of Lablab purpureus (L.) Sweet (hyacinth bean) diversity and landraces discrimination. Hyacinth bean displays an enormous variability of agro-morphological traits, probably linked to the multi-purpose uses in different regions, i.e. as pulse, or as food with nutraceutical potential (Africa and Asia), forage (Africa and Australia) and ornamental (Europe and USA). Only two forage cultivars are widely marketed, cv. Rongai and cv. Highworth, with several landraces remaining to be addressed in terms of diversity. We show that fatty acids profiling was able to distinguish landraces, which display shared fatty acids with cultivars from the center of hyacinth bean diversity origin (East Africa). We propose that fatty acid profiling is a tool that may be used not only for nutritional value assessment but also as a chemodiversity tool in crop research., (Copyright © 2018 Elsevier Masson SAS. All rights reserved.)

The flora of New Caledonia encompasses more than 3000 plant species and an endemism of almost 80%. New Caledonia is even considered as one of the 34 'hot spots' for biodiversity. Considering the current global loss of biodiversity and the fact that several drugs and pesticides become obsolete, there is an urgent need to increase sampling and research on new natural products. In this context, here, we reviewed the chemical knowledge available on New Caledonian native flora from economical perspectives. We expect that a better knowledge of the economic potential of plant chemistry will encourage the plantation of native plants for the development of a sustainable economy which will participate in the conservation of biodiversity. This review is divided into three parts, and the third part which is presented here summarizes the scientific literature related to the chemistry of endemic santalales, caryophyllales, and asterids. We show that the high rate of endemism is correlated with the originality of phytochemicals encountered in New Caledonian plants. A total of 176 original natural compounds have been identified from these plants, whereas many species have not been investigated so far. We also discuss the economic potential of plants and molecules with consideration of their medicinal and industrial perspectives. This review finally highlights several groups, such as Sapotaceae, that are unexplored in New Caledonia despite the high chemical interest in them. These plants are considered to have priority in future chemical investigations., (© 2016 Verlag Helvetica Chimica Acta AG, Zürich.)

Marine micro- and macroorganisms are well known to produce metabolites with high biotechnological potential. Nearly 40 years of systematic prospecting all around the New Caledonia archipelago and several successive research programs have uncovered new chemical leads from benthic and planktonic organisms. After species identification, biological and/or pharmaceutical analyses are performed on marine organisms to assess their bioactivities. A total of 3582 genera, 1107 families and 9372 species have been surveyed and more than 350 novel molecular structures have been identified. Along with their bioactivities that hold promise for therapeutic applications, most of these molecules are also potentially useful for cosmetics and food biotechnology. This review highlights the tremendous marine diversity in New Caledonia, and offers an outline of the vast possibilities for natural products, especially in the interest of pursuing collaborative fundamental research programs and developing local biotechnology programs.

This paper reports a pharmacophylogenetic study of a medicinal plant family, Ranunculaceae, investigating the correlations between their phylogeny, chemical constituents, and pharmaceutical properties. Phytochemical, ethnopharmacological, and pharmacological data were integrated in the context of the systematics and molecular phylogeny of the Ranunculaceae. The chemical components of this family included several representative metabolic groups: benzylisoquinoline alkaloids, ranunculin, triterpenoid saponin, and diterpene alkaloids, among others. Ranunculin and magnoflorine were found to coexist in some genera. The pharmacophylogenetic analysis, integrated with therapeutic information, agreed with the taxonomy proposed previously, in which the family Ranunculaceae was divided into five sub-families: Ranunculoideae, Thalictroideae, Coptidoideae, Hydrastidoideae, and Glaucidioideae. It was plausible to organize the sub-family Ranunculoideae into ten tribes. The chemical constituents and therapeutic efficacy of each taxonomic group were reviewed, revealing the underlying connections between phylogeny, chemical diversity, and clinical use, which should facilitate the conservation and sustainable utilization of the pharmaceutical resources derived from the Ranunculaceae., (Copyright © 2015 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)

Fungi have a unique metabolic plasticity allowing them to produce a wide range of natural products. Since the discovery of penicillin, an antibiotic of fungal origin, substantial efforts have been devoted globally to search for fungal-derived natural bioactive products. Andean region forests represent one of the few undisturbed ecosystems in the world with little human intervention. While these forests display a rich biological diversity, mycological and chemical studies in these environments have been scarce. This review aims to summarise all the efforts regarding the chemical or bioactivity analyses of Agaricomycetes (Basidiomycota) from southern South America environments. Overall, herein we report a total of 147 fungal species, 21 of them showing chemical characterisation and/or biological activity. In terms of chemical cores, furans, chlorinated phenol derivatives, polyenes, lactones, terpenes and himanimides have been reported. These natural products displayed a range of biological activities including antioxidant, antimicrobial, antifungal, neuroprotective and osteoclast-forming suppressing effects. [ABSTRACT FROM AUTHOR]

The ecologically and economically important genus Chrysanthemum contains around 40 species and many hybrids and cultivars. The dried capitulum of Chrysanthemum morifolium (CM) Ramat. Tzvel, i.e., Flos Chrysanthemi, is frequently used in traditional Chinese medicine (TCM) and folk medicine for at least 2,200years. It has also been a popular tea beverage for about 2,000years since Han Dynasty in China. However, the origin of different cultivars of CM and the phylogenetic relationship between Chrysanthemum and related Asteraceae genera are still elusive, and there is a lack of comprehensive review about the association between biodiversity and chemodiversity of Chrysanthemum. This article aims to provide a synthetic summary of the phylogeny, biodiversity, phytometabolites and chemodiversity of Chrysanthemum and related taxonomic groups, focusing on CM and its wild relatives. Based on extensive literature review and in light of the medicinal value of chrysanthemum, we give some suggestions for its relationship with some genera/species and future applications. Mining chemodiversity from biodiversity of Chrysanthemum containing subtribe Artemisiinae, as well as mining therapeutic efficacy and other utilities from chemodiversity/biodiversity, is closely related with sustainable conservation and utilization of Artemisiinae resources. There were eight main cultivars of Flos Chrysanthemi, i.e., Hangju, Boju, Gongju, Chuju, Huaiju, Jiju, Chuanju and Qiju, which differ in geographical origins and processing methods. Different CM cultivars originated from various hybridizations between multiple wild species. They mainly contained volatile oils, triterpenes, flavonoids, phenolic acids, polysaccharides, amino acids and other phytometabolites, which have the activities of antimicrobial, anti-viral, antioxidant, anti-aging, anticancer, antiinflammatory, and closely related taxonomic groups could also be useful as food, medicine and tea. Despite some progresses, the genetic/chemical relationships among varieties, species and relevant genera have yet to be clarified; therefore, the roles of pharmacophylogeny and omics technology are highlighted. [ABSTRACT FROM AUTHOR]

An extraordinarily high intraspecific chemical diversity, i.e. chemodiversity, has been found in several plant species, of which some are of major ecological or economic relevance. Moreover, even within an individual plant there is substantial chemodiversity among tissues and across seasons. This chemodiversity likely has pronounced ecological effects on plant mutualists and antagonists, associated foodwebs and, ultimately, biodiversity. Surprisingly, studies on interactions between plants and their herbivores or pollinators often neglect plant chemistry as a level of diversity and phenotypic variation. The main aim of this Research Unit (RU) is to understand the emergence and maintenance of intraspecific chemodiversity in plants. We address the following central questions:1) How does plant chemodiversity vary across levels, i.e., within individuals, among individuals within populations, and among populations?2) What are the ecological consequences of intraspecific plant chemodiversity?3) How is plant chemodiversity genetically determined and maintained?By combining field and laboratory studies with metabolomics, transcriptomics, genetic tools, statistical data analysis and modelling, we aim to understand causes and consequences of plant chemodiversity and elucidate its impacts on the interactions of plants with their biotic environment. Furthermore, we want to identify general principles, which hold across different species, and develop meaningful measures to describe the fascinating diversity of defence chemicals in plants. These tasks require integrated scientific collaboration of experts in experimental and theoretical ecology, including chemical and molecular ecology, (bio)chemistry and evolution.

Phenolic compounds (PCs) are a family of secondary metabolites with recognized biological activities making them attractive for the biomedical "red" biotechnology. The development of the eco-sustainable production of natural bioactive metabolites requires using easy cultivable organisms, such as microalgae, which represents one of the most promising sources for biotechnological applications. Microalgae are photosynthetic organisms inhabiting aquatic systems, displaying high levels of biological and functional diversities, and are well-known producers of fatty acids and carotenoids. They are also rich in other families of bioactive molecules e.g. phenolic compounds. Microalgal PCs however are less investigated than other molecular components. This study aims to provide a state-of-art picture of the actual knowledge on microalgal phenolic compounds, reviewing information on the PC content variety and chemodiversity in microalgae, their environmental modulation, and we aim to report discuss data on PC biosynthetic pathways. We report the challenges of promoting microalgae as a relevant source of natural PCs, further enhancing the interests of microalgal "biofactories" for biotechnological applications (i.e. nutraceutical, pharmacological, or cosmeceutical products). [ABSTRACT FROM AUTHOR]

An extraordinarily high intraspecific chemical diversity, i.e. chemodiversity, has been found in several plant species, of which some are of major ecological or economic relevance. Moreover, even within an individual plant there is substantial chemodiversity among tissues and across seasons. This chemodiversity likely has pronounced ecological effects on plant mutualists and antagonists, associated foodwebs and, ultimately, biodiversity. Surprisingly, studies on interactions between plants and their herbivores or pollinators often neglect plant chemistry as a level of diversity and phenotypic variation. The main aim of this Research Unit (RU) is to understand the emergence and maintenance of intraspecific chemodiversity in plants. We address the following central questions: 1) How does plant chemodiversity vary across levels, i.e., within individuals, among individuals within populations, and among populations? 2) What are the ecological consequences of intraspecific plant chemodiversity? 3) How is plant chemodiversity genetically determined and maintained? By combining field and laboratory studies with metabolomics, transcriptomics, genetic tools, statistical data analysis and modelling, we aim to understand causes and consequences of plant chemodiversity and elucidate its impacts on the interactions of plants with their biotic environment. Furthermore, we want to identify general principles, which hold across different species, and develop meaningful measures to describe the fascinating diversity of defence chemicals in plants. These tasks require integrated scientific collaboration of experts in experimental and theoretical ecology, including chemical and molecular ecology, (bio)chemistry and evolution. [ABSTRACT FROM AUTHOR]

Background Different parts of the tree Calophyllum inophyllum L. (nuts, leaves, roots, bark, fruits, nut oil and resin) are used as traditional medicines and cosmetics in most of the Pacific Islands. The oil efficiency as a natural cure and in traditional cosmetics has been largely described throughout the South Pacific, which led us to investigate C. inophyllum’s chemical and genetic diversity. A correlative study of the nut resin and leaf DNA from three distinct archipelagos in the South Pacific was carried out in order to identify diversity patterns in C. inophyllum across the South Pacific. Methods Calophyllum inophyllum plants were sampled from French Polynesia, New Caledonia and Fiji. We extracted tamanu oil (nut oil) resin for chemo-diversity studies and sampled leaf tissues for genetic studies. We applied an analysis method designed for small quantities (at a microscale level), and used High Performance Liquid Chromatography (HPLC) to establish the chemo-diversity of tamanu oil resin. In-house standards were co-eluted for qualitative determination. Genetic diversity was assessed using chloroplast barcoding markers (the Acetyl-CoA carboxylase (accD) gene and the psaA-ycf3 intergenic spacer region). Results Our HPLC analysis revealed 11 previously known tamanu oil constituents, with variability among plant samples. We also isolated and characterized two new neoflavonoids from tamanu oil resin namely, tamanolide E1 and E2 which are diastereoisomers. Although genetic analysis revealed low genetic variation, our multivariate analysis (PCA) of the tamanu oil resin chemical profiles revealed differentiation among geographic regions. Conclusion We showed here that chromatographic analysis using formalized in-house standards of oil resin compounds for co-elution studies against oil resin samples could identify patterns of variation among samples of C. inophyllum, and discriminate samples from different geographical origins.

In plant ecology, biochemical analyses of bryophytes and vascular plants are often conducted on dried herbarium specimen as species typically grow in distant and inaccessible locations. Here, we present an automated in silico compound classification framework to annotate metabolites using an untargeted data independent acquisition (DIA)–LC/MS–QToF-sequential windowed acquisition of all theoretical fragment ion mass spectra (SWATH) ecometabolomics analytical method. We perform a comparative investigation of the chemical diversity at the global level and the composition of metabolite families in ten different species of bryophytes using fresh samples collected on-site and dried specimen stored in a herbarium for half a year. Shannon and Pielou’s diversity indices, hierarchical clustering analysis (HCA), sparse partial least squares discriminant analysis (sPLS-DA), distance-based redundancy analysis (dbRDA), ANOVA with post-hoc Tukey honestly significant difference (HSD) test, and the Fisher’s exact test were used to determine differences in the richness and composition of metabolite families, with regard to herbarium conditions, ecological characteristics, and species. We functionally annotated metabolite families to biochemical processes related to the structural integrity of membranes and cell walls (proto-lignin, glycerophospholipids, carbohydrates), chemical defense (polyphenols, steroids), reactive oxygen species (ROS) protection (alkaloids, amino acids, flavonoids), nutrition (nitrogen- and phosphate-containing glycerophospholipids), and photosynthesis. Changes in the composition of metabolite families also explained variance related to ecological functioning like physiological adaptations of bryophytes to dry environments (proteins, peptides, flavonoids, terpenes), light availability (flavonoids, terpenes, carbohydrates), temperature (flavonoids), and biotic interactions (steroids, terpenes). The results from this study allow to construct chemical traits that can be attributed to biogeochemistry, habitat conditions, environmental changes and biotic interactions. Our classification framework accelerates the complex annotation process in metabolomics and can be used to simplify biochemical patterns. We show that compound classification is a powerful tool that allows to explore relationships in both molecular biology by “zooming in” and in ecology by “zooming out”. The insights revealed by our framework allow to construct new research hypotheses and to enable detailed follow-up studies.

Cyanobacteria are a well-known source of bioproducts which renders culturable strains a valuable resource for biotechnology purposes. We describe here the establishment of a cyanobacterial culture collection (CC) and present the first version of the strain catalog and its online database (http://lege.ciimar.up.pt/). The LEGE CC holds 386 strains, mainly collected in coastal (48%), estuarine (11%), and fresh (34%) water bodies, for the most part from Portugal (84%). By following the most recent taxonomic classification, LEGE CC strains were classified into at least 46 genera from six orders (41% belong to the Synechococcales), several of them are unique among the phylogenetic diversity of the cyanobacteria. For all strains, primary data were obtained and secondary data were surveyed and reviewed, which can be reached through the strain sheets either in the catalog or in the online database. An overview on the notable biodiversity of LEGE CC strains is showcased, including a searchable phylogenetic tree and images for all strains. With this work, 80% of the LEGE CC strains have now their 16S rRNA gene sequences deposited in GenBank. Also, based in primary data, it is demonstrated that several LEGE CC strains are a promising source of extracellular polymeric substances (EPS). Through a review of previously published data, it is exposed that LEGE CC strains have the potential or actual capacity to produce a variety of biotechnologically interesting compounds, including common cyanotoxins or unprecedented bioactive molecules. Phylogenetic diversity of LEGE CC strains does not entirely reflect chemodiversity. Further bioprospecting should, therefore, account for strain specificity of the valuable cyanobacterial holdings of LEGE CC. [ABSTRACT FROM AUTHOR]

The central aim in ecometabolomics and chemical ecology is to pinpoint chemical features that explain molecular functioning. The greatest challenge is the identification of compounds due to the lack of constitutive reference spectra, the large number of completely unknown compounds, and bioinformatic methods to analyze the big data. In this study we present an interdisciplinary methodological framework that extends ultra-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC/ESI-QTOF-MS) with data-dependent acquisition (DDA-MS) and the automated in silico classification of fragment peaks into compound classes. We synthesize findings from a prior study that explored the influence of seasonal variations on the chemodiversity of secondary metabolites in nine bryophyte species. Here we reuse and extend the representative dataset with DDA-MS data. Hierarchical clustering, heatmaps, dbRDA, and ANOVA with post-hoc Tukey HSD were used to determine relationships of the study factors species, seasons, and ecological characteristics. The tested bryophytes showed species-specific metabolic responses to seasonal variations (50% vs. 5% of explained variation). Marchantia polymorpha, Plagiomnium undulatum, and Polytrichum strictum were biochemically most diverse and unique. Flavonoids and sesquiterpenoids were upregulated in all bryophytes in the growing seasons. We identified ecological functioning of compound classes indicating light protection (flavonoids), biotic and pathogen interactions (sesquiterpenoids, flavonoids), low temperature and desiccation tolerance (glycosides, sesquiterpenoids, anthocyanins, lactones), and moss growth supporting anatomic structures (few methoxyphenols and cinnamic acids as part of proto-lignin constituents). The reusable bioinformatic framework of this study can differentiate species based on automated compound classification. Our study allows detailed insights into the ecological roles of biochemical constituents of bryophytes with regard to seasonal variations. We demonstrate that compound classification can be improved with adding constitutive reference spectra to existing spectral libraries. We also show that generalization on compound classes improves our understanding of molecular ecological functioning and can be used to generate new research hypotheses.

Despite huge efforts by academia and pharmaceutical industry, cancer remains the second cause of disease-related death in developed countries. Novel sources and principles of anticancer drug discovery are in urgent demand. Marine-derived natural products represent a largely untapped source of future drug candidates. This review focuses on the anticancer drug discovery potential of marine invertebrates from the North-West Pacific. The issues of biodiversity, chemodiversity, and the anticancer pharmacophore diversity this region hides are consecutively discussed. These three levels of diversity are analyzed from the point of view of the already discovered compounds, as well as from the assessment of the overall, still undiscovered and enormous potential. We further go into the predictions of the economic and societal benefits the full-scale exploration of this potential offers, and suggest strategic measures to be taken on the national level in order to unleash such full-scale exploration. The transversal and multi-discipline approach we attempt to build for the case of marine invertebrate-based anticancer drug discovery from a given region can be applied to other regions and disease conditions, as well as up-scaled to global dimensions.

The genus Antirrhinum comprises about 28 species with a center of origin in the Iberian Peninsula. They show an important diversity of growing niches. We have performed a comprehensive analysis of scent profiles in eight wild species, Antirrhinum linkianum, A. tortuosum, A. cirrigherum, A. latifolium, A. meonanthum, A. braun-blanquetii, A. barrelieri, and A. graniticum. We used also two laboratory inbred lines A. majus, 165E and Sippe50. We identified 63 volatile organic compounds (VOCs) belonging to phenylpropanoids, benzenoids, mono- and sesquiterpenes, nitrogen-containing compounds, and aliphatic alcohols previously described in plants. Twenty-four VOCs were produced at levels higher than 2% of total VOC emission, while other VOCs were emitted in trace amounts. The absolute scent emission varied during flower maturation and species. The lowest emitting was A. meonanthum while A. tortuosum had the largest emissions. Species were clustered according to their scent profiles and the resulting dendrogram matched the current species phylogeny. However, two accessions, A. majus Sippe 50 and A. braun-blanquetii, showed development-specific changes in their VOC composition, suggesting a precise control and fine tuning of scent profiles. Cluster analysis of the different scent components failed to identify a specific synthesis pathway, indicating a key role of scent profiles as blends. There is considerable degree of chemodiversity in scent profiles in Antirrhinum. The specific developmental stage plays an important role in scent quantitative emissions. The relative robustness of the bouquets could be an adaptation to local pollinators. [ABSTRACT FROM AUTHOR]

Phytoextraction is widely used for the reclamation of degraded sites, particularly to remove trace metals from contaminated soils. Whereas this technique demonstrates several advantages, the biomass resulting from phytoextraction processes is highly enriched in metallic elements and constitutes therefore a problematic waste. We show here that this biomass can be used for the preparation of novel polymetallic extracts, with high potential as catalysts or reagents in organic synthesis. This new concept of ecocatalysis constitutes an innovative recycling of metallic elements whose current known reserves could be exhausted in the coming decades. The ecocatalysts Eco-Zn and Eco-Ni prepared respectively from Zn and Ni hyperaccumulating plants display two distinct chemical reactivities, starting from the same substrates. Eco-Zn led to the formation of esters of commercial interest for the fragrance industry, following a hydro-acyloxy-addition reaction pathway. In contrast, Eco-Ni afforded chlorinated products thank to the hydrochlorination of alkenes. Both ecocatalysts allowed the synthesis of valuable products in high yields through methodologies in line with the spirit of sustainable chemistry. [ABSTRACT FROM AUTHOR]

The central aim in ecometabolomics and chemical ecology is to pinpoint chemical features that explain molecular functioning. The greatest challenge is the identification of compounds due to the lack of constitutive reference spectra, the large number of completely unknown compounds, and bioinformatic methods to analyze the big data. In this study we present an interdisciplinary methodological framework that extends ultra-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC/ESI-QTOF-MS) with data-dependent acquisition (DDA-MS) and the automated in silico classification of fragment peaks into compound classes. We synthesize findings from a prior study that explored the influence of seasonal variations on the chemodiversity of secondary metabolites in nine bryophyte species. Here we reuse and extend the representative dataset with DDA-MS data. Hierarchical clustering, heatmaps, dbRDA, and ANOVA with post-hoc Tukey HSD were used to determine relationships of the study factors species, seasons, and ecological characteristics. The tested bryophytes showed species-specific metabolic responses to seasonal variations (50% vs. 5% of explained variation). Marchantia polymorpha, Plagiomnium undulatum, and Polytrichum strictum were biochemically most diverse and unique. Flavonoids and sesquiterpenoids were upregulated in all bryophytes in the growing seasons. We identified ecological functioning of compound classes indicating light protection (flavonoids), biotic and pathogen interactions (sesquiterpenoids, flavonoids), low temperature and desiccation tolerance (glycosides, sesquiterpenoids, anthocyanins, lactones), and moss growth supporting anatomic structures (few methoxyphenols and cinnamic acids as part of proto-lignin constituents). The reusable bioinformatic framework of this study can differentiate species based on automated compound classification. Our study allows detailed insights into the ecological roles of biochemical constituents of bryophytes with regard to seasonal variations. We demonstrate that compound classification can be improved with adding constitutive reference spectra to existing spectral libraries. We also show that generalization on compound classes improves our understanding of molecular ecological functioning and can be used to generate new research hypotheses. [ABSTRACT FROM AUTHOR]