Variety Of Secondary Metabolites Research Articles

Pharmacognostical Profile of Gymnema sylvestre and its Anti-Hyperglycemic Activity

In this paper explored the pharmacognostical profile of gymnema sylvestre and its anti-hyperglycemic activity has been documented well with references. The importance of the species in Ayurveda has been highlighted. The bioactive components like gymnema sylvestre has a variety of secondary metabolites, including oleanane, gymnemic acid, gymnemasides (A-F), gymnemic acid (IXVIII) homologue, gymnemic acid A1 and its derivatives, triterpenoidsaponin, al has been clearly includedin the review kaloid (Conduritol-A), polypeptide (Gurmarin), and gymnemasaponins. This study has provided the groundwork for developing a pharmacognostical profile of medicinal plant growers and collectors. The goal of this review study is to provide a regional profile of the indigenous knowledge system for medicinal plant usage and cultural behaviors related to healing. This study aids in the identification of novel ethnomedicinal plant species in the study region, which may lead to the development of new medicines. The plant toxicity test results indicated that it may be used as an alternative to diabetes therapy with no or little adverse effects. This study confirms the conventional use of indigenous plant-derived natural medicine for treating diabetes mellitus. The study also highlighted the efficacy of "Ayurveda" which is an ancient tradition, used in some parts of India. This ancient concept should be carefully evaluated in the light of modern medical science and can be utilized partially if found suitable. I hope that this kind of research will be useful to future researchers as per their needs.

Comparative Metabolomics of Reproductive Organs in the Genus Aesculus (Sapindaceae) Reveals That Immature Fruits Are a Key Organ of Procyanidin Accumulation and Bioactivity.

Fruit from A. hippocastanum L. are used commercially for chronic venous insufficiency (CVI). The isomeric mixture of pentacyclic triterpenoid saponins (β-aescin) exert anti-inflammatory effects. Hence, research has focused on β-aescin, yet the diversity, accumulation, and bioactivity of organ-specific secondary metabolites represent missed pharmacological opportunities. To this end, we applied an untargeted metabolomics approach by liquid chromatography—tandem mass spectrometry (LC–MS/MS) to the chemical profiles of flowers, immature fruits, and pedicels from 40 specimens across 18 species of Aesculus. Principal component analysis (PCA), orthogonal partial least squares (OPLS-DA), and molecular networking revealed stronger chemical differences between plant organs, than between species. Flowers are rich in glycosylated flavonoids, pedicels in organic acids and flavonoid aglycones, and immature fruits in monomeric flavan-3-ols and procyanidins. Although a high diversity of flavonoids and procyanidins was observed, the relative amounts differed by plant organ. Fruit extracts demonstrated the strongest antifungal (Saccharomyces cerevisiae) and antioxidant activity, likely from the procyanidins. Overall, secondary metabolite profiles are organ-specific, and fruits accumulate antifungal and antioxidant compounds. Due to the chemical similarity between species, similar effects may be achieved between species. This creates incentives for further exploration of the entire genus, in bioprospecting for potential therapeutic leads.

Stemphylium and Ulocladium between Benefit and Harmful

Background: Emerging of microbial resistance, spread of life-threatening diseases, and biological control of pathogens destroying economically important crops, are serious problems that encourage scientists to search for unusual sources for novel compounds with biological activities. Fungi are promising sources for such compounds due to their ability to produce variety of secondary metabolites that could be, if truly investigated, the solution for currently serious problems. Aim: The aim of this review is to highlight the diversity of compounds produced by endophytic Stemphylium and Ulocladium and represents their ability to produce biologically diverse metabolites. Materials and methods: This was a narrative review. A comprehensive literature search was done using PubMed, Google Scholar, Scopus, and EMBASE using the keywords, Stemphylium; Ulocladium; Secondary metabolites; biological activities. Results: Many studies reported that the endophytic Ulocladium especially, Ulocladium atrum Preuss, showed promising biocontrol activity against Botrytis cinerea on crops cultivated in the greenhouse and the field. The endophytic fungus Stemphylium especially, Stemphylium globuliferum was isolated from stem tissues of the Moroccan medicinal plant Mentha pulegium. Extracts of the fungus exhibited significant cytotoxicity when tested in vitro against L5178Y cells. Conclusion: Endophytic fungi are a noble and consistent source of unique natural mixtures with a high level of biodiversity and may also yield several compounds of pharmaceutical significance, which is currently attracting scientific surveys worldwide. Every study conducted on Stemphylium and Ulocladium resulted in discovery of new metabolites or pointing to a possible application, which made Stemphylium and Ulocladium species potential source of pharmaceuticals and attracted attention for further investigations of their biological control.

Rare Glutamic Acid Methyl Ester Peptaibols from Sepedonium ampullosporum Damon KSH 534 Exhibit Promising Antifungal and Anticancer Activity.

Fungal species of genus Sepedonium are rich sources of diverse secondary metabolites (e.g., alkaloids, peptaibols), which exhibit variable biological activities. Herein, two new peptaibols, named ampullosporin F (1) and ampullosporin G (2), together with five known compounds, ampullosporin A (3), peptaibolin (4), chrysosporide (5), c(Trp-Ser) (6) and c(Trp-Ala) (7), have been isolated from the culture of Sepedonium ampullosporum Damon strain KSH534. The structures of 1 and 2 were elucidated based on ESI-HRMSn experiments and intense 1D and 2D NMR analyses. The sequence of ampullosporin F (1) was determined to be Ac-Trp1-Ala2-Aib3-Aib4-Leu5-Aib6-Gln7-Aib8-Aib9-Aib10-GluOMe11-Leu12-Aib13-Gln14-Leuol15, while ampullosporin G (2) differs from 1 by exchanging the position of Gln7 with GluOMe11. Furthermore, the total synthesis of 1 and 2 was carried out on solid-phase to confirm the absolute configuration of all chiral amino acids as L. In addition, ampullosporin F (1) and G (2) showed significant antifungal activity against B. cinerea and P. infestans, but were inactive against S. tritici. Cell viability assays using human prostate (PC-3) and colorectal (HT-29) cancer cells confirmed potent anticancer activities of 1 and 2. Furthermore, a molecular docking study was performed in silico as an attempt to explain the structure-activity correlation of the characteristic ampullosporins (1–3).

Research progress on plant biosynthetic gene cluster

<p indent=0mm>Plants produce a wide variety of structurally and functionally diverse metabolites, many of which play an indispensable role in plant growth and development and in the response to abiotic and biotic stresses. In recent years, plant biosynthetic gene clustering has attracted extensive attention from scientists, and the rapid development of multi-omics technologies such as genome, transcriptome and metabolome makes it possible to efficiently mine plant metabolic gene clusters. Further, the studies of plant biosynthetic gene clusters will provide new insights to explore and utilize the diversity of plant secondary metabolites. Here, we not only systematically summarize the structural characteristics and regulatory models of plant biosynthetic gene clusters, but also review the application of new technologies in the discovery and identification of biosynthetic gene clusters.

Chemoprevention of NCI-H322 Lung Cancer Cells Proliferation and Tumor Regression in Murine Ascites Model by Dietary Flavonoid Quercetin

Prunus cerasus L (Sour cherries) contain diverse secondary metabolites which exhibit various biological activities, including anticancer, antioxidant, and anti-inflammatory properties. The present study aimed to determine the anticancer efficacy of four compounds, quercetin, daidzin, rutin, and chlorogenic acid, isolated from Prunus cerasus fruit. The antiproliferative activity of four cherry isolates was determined against five different cancer cell lines (NCI-H322, A549, THP-1, MCF-7, and PC-3) by Tetrazolium bromide assay, followed by apoptosis Cell cycle analyses, mitochondrial membrane potential, cell migration test, and in vivo Ehrlich Ascites Carcinoma studies using potent bioactive lead. The cytotoxicity profile of the four molecules demonstrated that quercetin induced significant cell growth inhibition in all cancer cell lines with paramount 79% cytotoxicity against NCI-H322 lung cancer cells (IC50 value 24μM). Incubation of NCI-H322 cells with quercetin showed a concentration-dependent increase in hypo-diploid sub G0/G1 DNA fraction, exhibited consequential changes in nuclear morphology, and caused mitochondrial transmembrane potential loss of 60.3% augmented at 30 µM. Pertaining to in vivo potency, quercetin manifested 89% tumor inhibition at 50 mg/kg body weight in EAC-bearing mice. The current studies raise the potential usefulness of quercetin in chemoprevention against lung cancer cells and support its empirical use as a promising nutraceutical agent.

Extraction and characterization of microalgae-derived phenolics for pharmaceutical applications: A systematic review.

Microalgae are regarded as a rich trove of diverse secondary metabolites that exert remarkable biological activities. In particular, microalgae-derived bioactive phenolic compounds (MBPCs) are a boon to biopharmaceutical and nutraceutical industries due to their diverse bioactivities, including antimicrobial, anticancer, antiviral, and immunomodulatory activities. The state-of-the-art green technologies for extraction and purification of MBPCs, along with the modern progress in the identification and characterization of MBPCs, have accelerated the discovery of novel active pharmaceutical compounds. However, several factors regulate the production of these bioactive phenolic compounds in microalgae. Furthermore, some microalgae species produce toxic phenolic compounds that negatively impact the aquatic ecosystem, animal, and human life. Therefore, the focus of this review paper is to bring into light the current innovations in bioprospection, extraction, purification, and characterization of MBPCs. This review is also aimed at a better understanding of the physicochemical factors regulating the production of MBPCs at an industrial scale. Finally, the present review covers the recent advances in toxicological evaluation, diverse applications, and future prospects of MBPCs in biopharmaceutical industries.

Sulochrins and alkaloids from a fennel endophyte Aspergillus sp. FVL2

The fungal endophyte Aspergillus sp. strain FVL2, isolated from the traditional medicinal fennel plant, Foeniculum vulgare, was investigated for secondary metabolites. Fermentation on rice medium followed by chromatographic separation delivered three new natural products, 7-demethyl-neosulochrin (1), fumigaclavine I (3) and N-benzoyl-tryptophan (6) together with further 14 known metabolites, 1-O-methyl-sulochrin-4'-sulfate, questin, laccaic acid, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumitremorgin C, fumigaquinazoline C, tryptoquivaline J, trypacidin, 3'-O-demethyl-sulochrin, 1-O-methyl-sulochrin, protocatechuic acid, and vermelone. The chemical structures of the new metabolites were determined by NMR spectroscopy and ESI HR mass spectrometry. For fumigaclavine I, we observed the partial deuterium transfer from the solvent to the enol form with a remarkable high stereo selectivity. The discovery of the new seco-anthraquinone 7-demethyl-neosulochrin (1) revealed a second type of ring cleavage by a questin oxygenase. The discovery of diverse secondary metabolites broadens the chemical space of Aspergillus.

Evaluation of Antihelminthic Activity of Bixa orellana

Intestinal worms are common problems in remote and rural areas of India. The communities of remote areas use some wild plants to treat intestinal worms. Among them, Bixa orellana is a monogenic plant of family Bixaceae, popularly known as lipstick tree or Annatto and locally called as Sinduri. It is traditionally used to kill the intestinal worms, results revealed that seeds of B. orellana possess diverse secondary metabolites such as tannin and phenolic compounds which might be responsible to kill the worms. Antihelminthic activity showed that seed extracts (aqueous, acetone, methanol, and ethanol) were effective against Eisenia fetida. Keeping the traditional uses of Sinduri against stomach worm and to reduce the side effects of synthetic drugs, the present experiment has been designed.

Phenolic compound and antioxidant activity of two slightly consumed wild mushrooms (Lentinus squarrosulus and Auricularia politrich) in three regions from center Ivory Coast

Mushrooms contain a variety of secondary metabolites, including various phenolic compounds, which have been shown to act as excellent antioxidants. In this study, the contents of total phenolic, flavonoids and tannins of mushrooms methanolic extracts were evaluated by colorimetric assays to ranges of 277.36±0.66 to 420.86±0.90 mg (GAE)/100g DW; 31.99±0.90 to 90.90±0.07mg (QE)/100g DW and 150.61±0.16 to 220.47±1.01mg (TAE)/100g DW respectively. HPLC-profiles of methanolic extracts indicated that the individual phenolic compounds found to the samples of the species of mushrooms that are Lentinus squarrosulus and Auricularia politrich revealed us that gallic acid, catechin, acid ρ-hydroxybenzoїc, acid ellagique and naringerin were presented to the level of the two species. With respect to organic acids, the results showed that citric acid and fumaric acid was the major organic acid in all the samples of both mushrooms species. The methanolic extracts of the two mushrooms exhibited the high DPPH radical scavenging activities ranging from 34.10±1.12 to 58.95±0.52%. These data indicated that these mushrooms could constitute a potential good source of natural antioxidant for the local population.

Hidden Diversity in an Antarctic Algal Forest: Metabolomic Profiling Linked to Patterns of Genetic Diversification in the Antarctic Red Alga Plocamium sp.

The common Antarctic red alga Plocamium sp. is rich in halogenated monoterpenes with known anticancer and antimicrobial properties and extracts of Plocamium sp. have strong ecological activity in deterring feeding by sympatric herbivores. Plocamium sp. collected near Anvers Island, Antarctica showed a high degree of secondary metabolite diversity between separate individuals. GC/MS results revealed 15 different combinations of metabolites (chemogroups) across individuals, which were apparent at 50% or greater Bray–Curtis similarity and also clearly distinguishable by eye when comparing chromatographic profiles of the secondary metabolomes. Sequencing of the mitochondrial cox1 gene revealed six distinct haplotypes, of which the most common two had been previously reported (now referred to as Haplotypes 1 and 2). With the exception of one individual, three of the chemogroups were only produced by individuals in Haplotype 1. All the other 12 chemogroups were produced by individuals in Haplotype 2, with five of these chemogroups also present in one of the four new, less common haplotypes that only differed from Haplotype 2 by one base pair. The functional relevance of this metabolomic and genetic diversity is unknown, but they could have important ecological and evolutionary ramifications, thus potentially providing a foundation for differential selection.

Three chromosome-scale Papaver genomes reveal punctuated patchwork evolution of the morphinan and noscapine biosynthesis pathway

For millions of years, plants evolve plenty of structurally diverse secondary metabolites (SM) to support their sessile lifestyles through continuous biochemical pathway innovation. While new genes commonly drive the evolution of plant SM pathway, how a full biosynthetic pathway evolves remains poorly understood. The evolution of pathway involves recruiting new genes along the reaction cascade forwardly, backwardly, or in a patchwork manner. With three chromosome-scale Papaver genome assemblies, we here reveal whole-genome duplications (WGDs) apparently accelerate chromosomal rearrangements with a nonrandom distribution towards SM optimization. A burst of structural variants involving fusions, translocations and duplications within 7.7 million years have assembled nine genes into the benzylisoquinoline alkaloids gene cluster, following a punctuated patchwork model. Biosynthetic gene copies and their total expression matter to morphinan production. Our results demonstrate how new genes have been recruited from a WGD-induced repertoire of unregulated enzymes with promiscuous reactivities to innovate efficient metabolic pathways with spatiotemporal constraint.

Metagenomic Sequencing of Multiple Soil Horizons and Sites in Close Vicinity Revealed Novel Secondary Metabolite Diversity.

ABSTRACTDiscovery of novel antibiotics is crucial for combating rapidly spreading antimicrobial resistance and new infectious diseases. Most of the clinically used antibiotics are natural products—secondary metabolites produced by soil microbes that can be cultured in the lab. Rediscovery of these secondary metabolites during discovery expeditions costs both time and resources. Metagenomics approaches can overcome this challenge by capturing both culturable and unculturable hidden microbial diversity. To be effective, such an approach should address questions like the following. Which sequencing method is better at capturing the microbial diversity and biosynthesis potential? What part of the soil should be sampled? Can patterns and correlations from such big-data explorations guide future novel natural product discovery surveys? Here, we address these questions by a paired amplicon and shotgun metagenomic sequencing survey of samples from soil horizons of multiple forest sites very close to each other. Metagenome mining identified numerous novel biosynthetic gene clusters (BGCs) and enzymatic domain sequences. Hybrid assembly of both long reads and short reads improved the metagenomic assembly and resulted in better BGC annotations. A higher percentage of novel domains was recovered from shotgun metagenome data sets than from amplicon data sets. Overall, in addition to revealing the biosynthetic potential of soil microbes, our results suggest the importance of sampling not only different soils but also their horizons to capture microbial and biosynthetic diversity and highlight the merits of metagenome sequencing methods.IMPORTANCE This study helped uncover the biosynthesis potential of forest soils via exploration of shotgun metagenome and amplicon sequencing methods and showed that both methods are needed to expose the full microbial diversity in soil. Based on our metagenome mining results, we suggest revising the historical strategy of sampling soils from far-flung places, as we found a significant number of novel and diverse BGCs and domains even in different soils that are very close to each other. Furthermore, sampling of different soil horizons can reveal the additional diversity that often remains hidden and is mainly caused by differences in environmental key parameters such as soil pH and nutrient content. This paired metagenomic survey identified diversity patterns and correlations, a step toward developing a rational approach for future natural product discovery surveys.

Bioactive PI3-kinase/Akt/mTOR Inhibitors in Targeted Lung Cancer Therapy.

One of the central signaling pathways with a regulatory effect on cell proliferation and survival is Akt/mTOR. In many human cancer types, for instance, lung cancer, the overexpression of Akt/mTOR has been reported. For this reason, either targeting cancer cells by synthetic or natural products affecting the Akt/mTOR pathway down-regulation is a useful strategy in cancer therapy. Direct inhibition of the signaling pathway or modulation of each related molecule could have significant feedback on the growth and proliferation of cancer cells. A variety of secondary metabolites has been identified to directly inhibit the AKT/mTOR signaling, which is important in the field of drug discovery. Naturally occurring nitrogenous and phenolic compounds can emerge as two pivotal classes of natural products possessing anticancer abilities. Herein, we have summarized the alkaloids and flavonoids for lung cancer treatment together with all the possible mechanisms of action relying on the Akt/mTOR pathway down-regulation. This review suggested that in search of new drugs, phytochemicals could be considered as promising scaffolds to be developed into efficient drugs for the treatment of cancer. In this review, the terms "Akt/mTOR", "Alkaloid", "flavonoid", and "lung cancer" were searched without any limitation in search criteria in Scopus, PubMed, Web of Science, and Google scholar engines.

Berkchaetoazaphilone B has antimicrobial activity and affects energy metabolism

Antimicrobial resistance has become one of the major threats to human health. Therefore, there is a strong need for novel antimicrobials with new mechanisms of action. The kingdom of fungi is an excellent source of antimicrobials for this purpose because it encompasses countless fungal species that harbor unusual metabolic pathways. Previously, we have established a library of secondary metabolites from 10,207 strains of fungi. Here, we screened for antimicrobial activity of the library against seven pathogenic bacterial strains and investigated the identity of the active compounds using ethyl acetate extraction, activity-directed purification using HPLC fractionation and chemical analyses. We initially found 280 antimicrobial strains and subsequently identified 17 structurally distinct compounds from 26 strains upon further analysis. All but one of these compounds, berkchaetoazaphilone B (BAB), were known to have antimicrobial activity. Here, we studied the antimicrobial properties of BAB, and found that BAB affected energy metabolism in both prokaryotic and eukaryotic cells. We conclude that fungi are a rich source of chemically diverse secondary metabolites with antimicrobial activity.

Characterization of evolutionarily distinct rice BAHD-Acyltransferases provides insight into their plausible role in rice susceptibility to Rhizoctonia solani.

Plants produce diverse secondary metabolites in response to different environmental cues including pathogens. The modification of secondary metabolites, including acylation, modulates their biological activity, stability, transport, and localization. A plant-specific BAHD-acyltransferase (BAHD-AT) gene family members catalyze the acylation of secondary metabolites. Here we characterized the rice (Oryza sativa L.) BAHD-ATs at the genome-wide level and endeavor to define their plausible role in the tolerance against Rhizoctonia solani AG1-IA. We identified a total of 85 rice OsBAHD-AT genes and classified them into five canonical clades based on their phylogenetic relationship with characterized BAHD-ATs from other plant species. The time-course RNA sequencing (RNA-seq) analysis of OsBAHD-AT genes and qualitative real-time polymerase chain reaction (qRT-PCR) validation showed higher expression in sheath blight susceptible rice genotype. Furthermore, the DNA methylation analysis revealed higher hypomethylation of OsBAHD-AT genes that corresponds to their higher expression in susceptible rice genotype, indicating epigenetic regulation of OsBAHD-AT genes in response to R. solani AG1-IA inoculation. The results shown here indicate that BAHD-ATs may have a negative role in rice tolerance against R. solani AG1-IA possibly mediated through the brassinosteroid (BR) signaling pathway. Altogether, the present analysis suggests the putative functions of several OsBAHD-AT genes, which will provide a blueprint for their functional characterization and to understand the rice-R. solani AG1-IA interaction.

Diversity and Biosynthesis of Volatile Terpenoid Secondary Metabolites in the Chrysanthemum Genus

Chrysanthemum is a significant genus belonging to one of the largest plant families, the Asteraceae. Among the over 40 recognized species, C. morifolium is best-known for its long history of cultivation and countless varieties. Like some other genera of this family, many Chrysanthemum species are producers of high levels of secondary metabolites. This review focuses on the largest class of plant secondary metabolites, namely terpenoids produced by Chrysanthemum species. An extensive literature search revealed a total of 390 terpenoids from these species, which include 183 monoterpenoids and 207 sesquiterpenoids. While some terpenes are produced by almost all of the investigated varieties/species of Chrysanthemum, many terpenoids show specificity to certain varieties or species, indicating species-specific functions. The enzymes and genes participating in the pathways for terpene biosynthesis are also described. In addition to a general overview, in this review we focus on isoprenyl diphosphate synthases and terpene synthases, two enzyme classes pivotal for generating the chemical diversity of terpenes, as established by our analysis of two sequenced genomes of Chrysanthemum. While our knowledge about the biological functions of terpenoids in Chrysanthemum is limited, we discuss their functions in chemical defenses against insects and microbial pathogens. Finally, we present the prospects of understanding the molecular basis of terpene biosynthesis in Chrysanthemum and elucidating its biological significance, as well as the prospects of translational research on terpene-based applications.

Effects of BrMYC2/3/4 on Plant Development, Glucosinolate Metabolism, and Sclerotinia sclerotiorum Resistance in Transgenic Arabidopsis thaliana.

MYC2/3/4, known as a basic helix–loop–helix (bHLH) transcription factor, directly activate the genes involved in diverse plant development and secondary metabolites biosynthesis. In this study, we identified and cloned five MYC paralogs (BrMYC2/3-1/3-2/4-1/4-2) from Chinese cabbage (Brassica rapa ssp. pekinensis). In-silico analyses for the physicochemical properties suggested that BrMYC2/3-1/3-2/4-2/4-3 are unstable hydrophobic and acidic proteins, while BrMYC4-1 is an unstable hydrophobic and basic protein. BrMYC2/3/4 belong to the bHLH superfamily and are closely related to AthMYC2/3/4 orthologs that mediate the regulation of various secondary metabolites. It was demonstrated that BrMYC2/3/4-GFP fusion protein localized in the nucleus and expression levels of five BrMYC2/3/4 homologous genes all elevated relative to control (Ctrl). When expressed in Arabidopsis under the control of 35S promoter, each of the BrMYC2/3-1/3-2/4-1/4-2 transgenes differentially influenced root and shoot elongation, vegetative phase change, flowering time, plant height and tiller number after flowering, and seed production. Despite the variation of phenotypes between the transgenic lines, all the lines except for BrMYC4-2 exhibited shorter seed length, less seed weight, higher accumulation of glucosinolates (GSs), and resistance to Sclerotinia sclerotiorum than Ctrl. Notably, BrMYC2 overexpression (OE) line significantly reduced the lengths of root and hypocotyl, seed length, and weight, along with faster bolting time and strikingly higher accumulation of total GSs. Accumulation of GSs at the highest levels in the BrMYC2OE line conferred the highest resistance to S. sclerotiorum. Unlike BrMYC3OE and BrMYC4OE, BrMYC2OE stimulated the growth of plant height after fluorescence. The results of this study point to the BrMYC2 overexpression that may provide a beneficial effect on plant growth and development via plant resistance to the fungal pathogen.

Genome Mining and Molecular Networking-Based Metabolomics of the Marine Facultative Aspergillus sp. MEXU 27854.

The marine-facultative Aspergillus sp. MEXU 27854, isolated from the Caleta Bay in Acapulco, Guerrero, Mexico, has provided an interesting diversity of secondary metabolites, including a series of rare dioxomorpholines, peptides, and butyrolactones. Here, we report on the genomic data, which consists of 11 contigs (N50~3.95 Mb) with a ~30.75 Mb total length of assembly. Genome annotation resulted in the prediction of 10,822 putative genes. Functional annotation was accomplished by BLAST searching protein sequences with different public databases. Of the predicted genes, 75% were assigned gene ontology terms. From the 67 BGCs identified, ~60% belong to the NRPS and NRPS-like classes. Putative BGCs for the dioxomorpholines and other metabolites were predicted by extensive genome mining. In addition, metabolomic molecular networking analysis allowed the annotation of all isolated compounds and revealed the biosynthetic potential of this fungus. This work represents the first report of whole-genome sequencing and annotation from a marine-facultative fungal strain isolated from Mexico.

Comparative Metabolomics of Fruits and Leaves in a Hyperdiverse Lineage Suggests Fruits Are a Key Incubator of Phytochemical Diversification.

Interactions between plants and leaf herbivores have long been implicated as the major driver of plant secondary metabolite diversity. However, other plant-animal interactions, such as those between fruits and frugivores, may also be involved in phytochemical diversification. Using 12 species of Piper, we conducted untargeted metabolomics and molecular networking with extracts of fruits and leaves. We evaluated organ-specific secondary metabolite composition and compared multiple dimensions of phytochemical diversity across organs, including richness, structural complexity, and variability across samples at multiple scales within and across species. Plant organ identity, species identity, and the interaction between the two all significantly influenced secondary metabolite composition. Leaves and fruit shared a majority of compounds, but fruits contained more unique compounds and had higher total estimated chemical richness. While the relative levels of chemical richness and structural complexity across organs varied substantially across species, fruit diversity exceeded leaf diversity in more species than the reverse. Furthermore, the variance in chemical composition across samples was higher for fruits than leaves. By documenting a broad pattern of high phytochemical diversity in fruits relative to leaves, this study lays groundwork for incorporating fruit into a comprehensive and integrative understanding of the ecological and evolutionary factors shaping secondary metabolite composition at the whole-plant level.