Variety Of Secondary Metabolites Research Articles

Terpenoids of plants from Chloranthaceae family: chemistry, bioactivity, and synthesis.

Covering: 1976 to December 2023Chloranthaceae is comprised of four extant genera (Chloranthus, Sarcandra, Hedyosmum, and Ascarina), totaling about 80 species, many of which have been widely used as herbal medicines for diverse medical purposes. Chloranthaceae plants represent a rich source of structurally interesting and diverse secondary metabolites, with sesquiterpenoids and diterpenoids being the predominant structural types. Lindenane sesquiterpenoids and their oligomers, chemotaxonomical markers of the family Chloranthaceae, have shown a wide spectrum of bioactivities, attracting significant attention from organic chemists and pharmacologists. Recent achievements also demonstrated the research value of two unique structural types in this plant family, sesquiterpenoid-monoterpenoid heterodimers and meroterpenoids. This review systematically summarizes 682 structurally characterized terpenoids from 22 Chloranthaceae plants and their key biological activities as well as the chemical synthesis of selected terpenoids.

The dichapetalins and dichapetalin-type compounds: structural diversity, bioactivity, and future research perspectives.

Covering mainly from 2013 up to 2023 with relevant references to work done before 2013First reported in 1995, the dichapetalins and analogous compounds constitute a novel class of natural dammarane-type merotriterpenoids characterized by their unique 2-phenylpyrano moiety annellated to ring A of the dammarane skeleton. They have been reported from only two genera: Dichapetalum (Dichapetalaceae) and Phyllanthus (Phyllanthaceae). About 100 novel dichapetalins and dichapetalin-type compounds, including the acutissimatriterpenes and their antitumour and other bioactivities have been reported. In the present review, we cover the distribution, ethnobotanical and medicinal importance and the diversity of secondary metabolites reported from the two genera Dichapetalum and Phyllanthus from 2013 to date, with appropriate reference to relevant information prior to 2013. We also propose and discuss possible biosynthetic pathways, antitumour activity against a broad range of human and murine cancer cell lines, structure activity relationships, and other biological activities and mechanisms of action. Finally, the review deals with future perspectives which include expansion of the structural diversity and bioactivity scope, possible simplification of the structural complexity of the compounds to enhance their drug-likeness, in silico studies, and continuation of the search for new dichapetalins and dichapetalin-type compounds from the over 200 Dichapetalum and over 1200 Phyllanthus species yet to be investigated. It is envisaged that the present review will stimulate further multidisciplinary and interdisciplinary studies.

New cytotoxic indole derivatives with anti-FADU potential produced by the endophytic fungus Penicillium oxalicum 2021CDF-3 through the OSMAC strategy.

Fungi possess well-developed secondary metabolism pathways that are worthy of in-depth exploration. The One Strain Many Compounds (OSMAC) strategy is a useful method for exploring chemically diverse secondary metabolites. In this study, continued chemical investigations of the marine red algae-derived endophytic fungus Penicillium oxalicum 2021CDF-3 cultured in PDB media yielded six structurally diverse indole derivatives, including two new prenylated indole alkaloids asperinamide B (1) and peniochroloid B (5), as well as four related derivatives (compounds 2-4 and 6). The chemical structures of these compounds, including the absolute configurations of 1 and 5, were determined by extensive analyses of HRESIMS, 1D and 2D NMR spectroscopic data, and TDDFT-ECD calculations. Compound 1 was found to possess an unusual 3-pyrrolidone dimethylbenzopyran fused to the bicyclo[2.2.2]diazaoctane moiety, which was rare in previously reported prenylated indole alkaloids. In vitro cytotoxic experiments against four human tumor cell lines (HeLa, HepG2, FADU, and A549) indicated that 1 strongly inhibited the FADU cell line, with an IC50 value of 0.43 ± 0.03 μM. This study suggested that the new prenylated indole alkaloid 1 is a potential lead compound for anti-FADU drugs.

Genome mining and AntiSMASH analysis of an Endophytic Talaromyces sp. reveal biosynthetic pathway gene clusters for novel bioactive compounds

Medicinal plants and their endophytes are one of the efficient producers of diverse secondary metabolites with therapeutic importance. In the present study, an endophytic fungus Talaromyces spp. isolated from Syzygium samarangense was subjected to whole-genome sequencing and Antibiotics and Secondary Metabolite Analysis Shell (AntiSMASH) annotation to identify biosynthetic gene clusters (BGCs) of secondary metabolites and their biosynthetic pathways. The Funannotate results revealed that the Talaromyces isolate has a total of 30.5Mb genome consisting of 372 contigs, 372 scaffolds and 47.64% GC content. In addition, 114 tRNA, 12722 functional mRNA, 12721 CDS transcripts, and 12721 protein-coding sequences were predicted and annotated using various BLAST databases. AntiSMASH revealed the presence of 76 BGCs, including 28 T1 Polyketide synthase (T1 PKS), 10 Nonribosomal peptide synthetases (NRPSs), 9 terpene, 1 Indole, 12 NRPs like, 4 T1 PKS and NRPs like, 2 T1 PKS Indole, 1 NRPs like terpene, 3 NRPs T1 PKS, 1 Indole NRPs, 2 betalactone, 1 phosphonate, 1 fungal-RiPP T1 PKS and 1 Other type. The analysis also predicted the occurrence of enzymes involved in the biosynthesis of some of the important secondary metabolites such as Pyranonigrin, Squalestatin -S, Azanigerone -A, Asperterpenoid -A, Napthopyrone, Clavaric acid, and Fusarin.

In- Vitro antioxidant activity of Primula denticulata aerial parts extracts

Abstract- In this study, we identify the anti-oxidant impact of ethanolic and aqueous extract of aerial parts of Primula denticulata and to evaluate the anti-oxidant effect of ethanolic and aqueous extract and compare to it with ascorbic acid and BHT by DPPH Radical Scavenging Assay methods because there is no scientific data available on the anti-oxidant activity of plant. The current investigation also showed that Primula denticulata aerial portions contain a variety of secondary metabolites. These phytochemicals may be a significant source of pharmacological compounds, meaning that the plant species may have enormous potential for use as a treatment for a range of chronic illnesses. The species' crude extract exhibits encouraging antioxidant potential as well, supporting the traditional use of this plant with scientific evidence.

GC-MS Analysis of Phytocomponents of Methanolic Bark Extract of Sterculia foetida

Species of the genus Sterculia have been shown to have a variety of secondary metabolites. However, there has not been the subject of significant research. This study is conducted to determine the phytocomponents in the methanolic bark extract of Sterculia foetida by GC-MS using a Shimadzu QP 2010 Ultra comprising an equipped with MS, ECD, and FID detector. This analysis revealed that the methanol extract of Sterculia foetida (bark) contained a total of 34 phytoconstituents and out of that Lupeol (63.81%), Lup-20(29)-en-3-one (5.54%) n-Hexadecenoic acid (5.73), and Vanillic acid (1.22%) were found to be in higher concentration. Lupeol has been reported to possess antiprotozoal, antimicrobial, anti-inflammatory, antioxidant, antidiabetic, antitumor, chemopreventive, and wound healing activity, while no activity was reported in Lup-20(29)-en-3-one. Vanillic acid exhibits anti-inflammatory, neuroprotective, Anti-Alzheimer, antiglycation, antibacterial, and hepatoprotective effects. From the results, it is evident that S. foetida contains various bioactive compounds and is recommended as a plant of pharmaceutical importance.

Chemical Composition of the Essential Oils of the Flowers Asphodelus aestivus Brot. Grown Wild in Jordan

Recent technological developments and methodological advances in GC-MS have become a common tool for investigating the quantity, quality, and chemical diversity of plant secondary metabolites. The flower parts of Asphodelus aestivus Brot. were studied, leading to the isolation and identification of various secondary metabolites, primarily essential oils: alcohol (26.9%); aldehyde (23%); alkanes, acetate derivatives, and aliphatic derivatives (19.2%); ketones (7.7%); and epoxides (3.8%). The principal oil components were 18.79% vetocitral C (trans), 17.27% hexadecyl acetate, 14.5% hexanal (2E), and 9.6% sabinene hydrate (trans). The identification of oil components was performed by matching their spectra with the mass spectra data bank.

Inhibitory Potential of Actinobacteria Isolated from Neelum Valley, Kashmir, Pakistan Against Typhoidal Salmonella

Given the emerging antimicrobial resistance (AMR), finding new antimicrobials and chemotherapeutics is a need of the hour. The under-explored habitats harbouring untapped microbial diversity are considered attractive targets to look for new potent bioactive compounds. In this study, N=32 actinobacteria strains were recovered from the soil of Neelum Valley, Kashmir, Pakistan, to screen their inhibitory activity and metabolomic potential against MDR typhoidal Salmonella. The TLC pattern and HPLC-UV-MS analysis of the extracts of isolated strains showed the presence of a variety of bioactive compounds. The actinobacteria strains B6, D13, B11.2 and others were found to be the most prolific producers of diverse secondary metabolites. In the screening for inhibitory activity against MDR typhoidal Salmonella, the extracts of strains B6, B16, B21 and D13 were found to be the most active exhibiting up to 20 mm zone of inhibition. Similarly, the cytotoxicity potential of the extracts against Artemiasalina by determining %larval mortality, the extract of strain Kel 1311A showed 91% mortality followed by the extracts of strains AzB1, kel 1391, B13, B8, and B4 showed % mortality up to 87.3%. 90%, 88% and 85.41% respectively. The HPLC-UV/MS analysis revealed the presence of a varietyof compounds with molecular weights of 400, 510 and 519 Daltons in the extract of strain B4 and 651, 356, 378 and 400 Daltons in the extracts of strain D13. The study suggested that actinobacteria living in the soil of Neelum Valley Kashmir are a rich source of novel bio-active, cytotoxic and anti-microbial compounds.

New prenylated indole-benzodiazepine-2,5-diones with α-glucosidase inhibitory activities from the mangrove-derived Aspergillus spinosus

Mangrove-derived fungi have been demonstrated to be promising source of structurally diverse and widely active secondary metabolites. During our search for new bioactive compounds, eight new indole-benzodiazepine-2,5-dione derivatives asperdinones A–H (1–8) and two known congeners (9 and 10) were isolated from the culture extracts of the mangrove-derived fungus Aspergillus spinosus WHUF0344 guided by one strain many compounds (OSMAC) and the heteronuclear 1H, 13C single-quantum coherence (HSQC) based small molecule accurate recognition technology (SMART) strategies. The structures and absolute configurations of the new compounds were elucidated by detailed spectroscopic analyze and electronic circular dichroism (ECD) calculations. The putative biosynthetic pathway of these compounds was proposed. Compounds 1–10 were evaluated for their antibacterial and α-glucosidase inhibitory activities. None of compounds showed antibacterial activity. Compounds 2–6 and 8 exhibited moderate inhibitory effects against α-glucosidase with IC50 values in the range of 24.65–312.25 μM. Besides, both 3 and 4 inhibited α-glucosidase variedly. Furthermore, the molecular docking study showed that compounds 2–4 were perfectly docking into the active sites of α-glucosidase. This study not only enriched the chemical diversity of secondary metabolites from the mangrove-derived fungi, but also provided potential hit compounds for further development of α-glucosidase inhibitors.

Taxonomic and functional assembly cues enrich the endophytic tobacco microbiota across epiphytic compartments.

The plant microbiome plays a critical role in plant growth, development, and health, with endophytes being recognized as essential members due to their close interactions with host plants. However, knowledge gaps remain in understanding the mechanisms driving the colonization and establishment of endophytic communities. To address this issue, we investigated the microbiota of tobacco roots and leaves, including both epiphytic and endophytic microorganisms. We found that Actinobacteria and Alphaproteobacteria were significantly enriched in the root endosphere. Additionally, we identified higher abundances of functional traits involved in antibiotic synthesis, plant cell wall degradation, iron metabolism, secretion systems, and nicotine degradation enzymes in the endosphere. We further studied metagenome-assembled genomes from the rhizosphere and root endosphere, revealing a greater diversity of secondary metabolites in bacteria within the root endosphere. Together, this study provides insights into the taxonomic and functional assembly cues that may contribute to shaping the endophytic plant microbiota.IMPORTANCEThe presence of diverse microorganisms within plant tissues under natural conditions is a well-established fact. However, due to the plant immune system's barrier and the unique microhabitat of the plant interior, it remains unclear what specific characteristics bacteria require to successfully colonize and thrive in the plant endosphere. Recognizing the significance of unraveling these functional features, our study focused on investigating the enriched traits in the endophytic microbiota compared to the epiphytes. Through our research, we have successfully identified the taxonomic and functional assembly cues that drive the enrichment of the endophytic microbiota across the epiphytic compartments. These findings shed new light on the intricate mechanisms of endophyte colonization, thereby deepening our understanding of plant-microbe interactions and paving the way for further advancements in microbiome manipulation.

Germplasm Resources and Metabolite Marker Screening of High-Flavonoid Tartary Buckwheat (Fagopyrum tataricum).

Tartary buckwheat is an annual minor cereal crop with a variety of secondary metabolites, endowing it with a high nutritional and medicinal value. Flavonoids constitute the primary compounds of Tartary buckwheat. Recently, metabolomics, as an adjunct breeding method, has been increasingly employed in crop research. This study explores the correlation between the total flavonoid content (TFC) and antioxidant capacity in 167 Tartary buckwheat varieties. Ten Tartary buckwheat varieties with significant differences in flavonoid content and antioxidant capacity were selected by cluster analysis. With the use of liquid chromatography-mass spectrometry, 58 flavonoid compounds were identified, namely, 42 flavonols, 10 flavanols, 3 flavanones, 1 isoflavone, 1 anthocyanidin, and 1 proanthocyanidin. Different samples were clearly separated by employing principal component analysis and partial least-squares discriminant analysis. Eight differential flavonoid compounds were further selected through volcano plots and variable importance in projection. Differential metabolites were highly correlated with TFC and antioxidant capacity. Finally, metabolic markers of kaempferol-3-O-hexoside, kaempferol-7-O-glucoside, and naringenin-O-hexoside were determined by the random forest model. The findings provide a basis for the selection and identification of Tartary buckwheat varieties with high flavonoid content and strong antioxidant activity.

Phytochemical Assessment, Antioxidant Activity, and in vitro Wound Healing Potential of Polygonum minus Huds

The increasing prevalence of chronic wounds, associated with aging, obesity, and diabetes, is compounded by bacterial resistance and adverse effects associated with commercial wound care products. Therefore, treatment modalities to accelerate the healing process are constantly being sought. This study aimed to investigate the phytochemical composition, antioxidant, and wound healing potential of the aqueous extract derived from the stems and leaves of Polygonum minus. The extract was subjected to phytochemical evaluation to assess the diversity of secondary metabolites. The total phenolic content (TPC) and total flavonoid content (TFC) were measured using the Folin-Ciocalteu colorimetric and aluminium chloride methods, respectively. The antioxidant activity was determined using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and ferric-reducing antioxidant power (FRAP) assays. The wound healing effects were evaluated using proliferation and migration assays on human epidermal keratinocyte (HaCaT) cells. The phytochemical evaluation of the aqueous extract revealed the presence of flavonoids, terpenoids, alkaloids, saponins, tannins, steroids, and cardiac glycosides. Furthermore, the extract exhibited high TPC (137.74 ± 0.75 µg/mL GAE) and TFC (177.08 ± 3.16 µg/mL QE) values, as well as radical scavenging activity at 79.50% in the DPPH assay and a FRAP value of 1485.67 ± 0.05 µM/g Fe2+. At the lowest concentration of 7.81 μg/mL, the extract significantly stimulated cell proliferation and migration within 24 hours of treatment. The stimulation of cell migration was comparable with that of allantoin, which was used as a positive control. This study indicated that the P. minus aqueous extract contains a high concentration of phenolic compounds, which could contribute significantly to its antioxidant activity and promote the proliferation and migration of keratinocytes. The findings suggest that the extract may merit further investigation for potential applications in topical therapy related to wound healing.

Draft genome sequence of endophytic fungus Talaromyces purpureogenus strain YAFEF302, isolated from Juglans sigillata.

Here, we report a draft genome sequence of endophytic fungus Talaromyces purpureogenus strain YAFEF302, isolated from Juglans sigillata. The genome resource will support future research into potential secondary metabolite diversity of this fungus.

Draft genome sequence of the endophytic fungus Phoma sp. strain YAFEF320, isolated from Gerbera jamesonii.

Here, we report a draft genome sequence of endophytic fungus Phoma sp. strain YAFEF320, isolated from the roots of Gerbera jamesonii. The genome size of Phoma sp. YAFEF320 was 32,542,820 bp with 52.08% GC content. The genome resource will support future research into potential secondary metabolite diversity of this fungus.

Morphological, phytochemical and genetic characterization of Centella asiatica accessions collected throughout Vietnam and Laos

Pennywort (Centella asiatica L.) is commonly grown in the tropical world for its nutritional and medicinal values. Valuable saponins in pennywort are extensively investigated for their anti-tumour activities. The diversity in morphology, phytochemical contents and genetics among pennywort accessions has been extensively studied to identify elite landraces for large-scale production. While pennywort is widely consumed in Vietnam, a systematic characterization of their diverse morphology, secondary metabolites and genetics is lacking. In this work, 26 pennywort accessions were collected across Vietnam and Laos. Their morphological features and yields were characterized under uniform agro-climatic conditions at Hue city in central Vietnam. The highest yield was obtained with HUIB_CA20 (478 g per tray), compared to the lowest yield in HUIB_CA19 (107 g per tray). Furthermore, a range of phytochemical markers, including vitamin C, reducing sugar, carotenoid, tannin, phenolic, flavonoid and saponin contents, were determined. Based on yield, phenolic and flavonoid contents, HUIB_CA20 and HUIB_CA27 were determined to be elite cultivars in this germplasm. Finally, microsatellite analysis was performed to explore the genetic diversity within the germplasm. Using fourteen SSR primer pairs, a total of 47 alleles were identified with 45 alleles (96 %) being polymorphic. These results will be useful for breeding programs aiming to create elite pennywort cultivars with enhanced properties.

Chitosan extracted from Cricket (Gryllus bimaculatus) induced bioactive compound and pigment content in Centella asiatica

Pegagan (Centela asiatica) is a plant contains a diversity of secondary metabolites. Chitosan, which is primarily derived from crustaceans and some certain insects, has been proposed as an active elicitor that enhances plant bioactive compounds. This study aimed to investigate the effect of chitosan application extracted from cricket (Grylus bimaculatus) and commercial chitosan to induce bioactive compound and pigment content in C. asiatica. The experiment was laid out in a completely randomized design (CRD) with three replications. Chitosan treatments were CN (without chitosan as control), CR (cricket chitosan at 50 ppm), and CM (commercial chitosan at 50 ppm), which were applied by spraying the leaves daily for 7 days. The changes in morphology, physiology, and biochemistry of the plants were analyzed after treatment. The result showed that foliar spray using cricket chitosan with 50 ppm doses induced the plants to have the highest bioactive compounds and pigment content. The enhancement levels of its bioactive compound and pigment content might contribute to the enhancement of its antioxidant activity levels of C. asiatica extract. This result highlights the remarkable potential of cricket (G. bimaculatus) as a promising alternative source of chitosan that can be used to stimulate bioactive compounds in C. asiatica.

Genomic Characterization of the Mycoparasite Pestalotiopsis sp. Strain cr013 from Cronartium ribicola.

The Pestalotiopsis sp. strain cr013 is a mycoparasite of Cronartium ribicola, a potential biocontrol fungus for Armand pine (Pinus armandii) blister rust. A previous study showed that the strain cr013 has great potential to produce new compounds. However, there has been no report of the whole-genome sequence of the mycoparasite Pestalotiopsis sp. In this study, the BGISEQ-500 and Oxford Nanopore GridION X5 sequencing platforms were used to sequence the strain cr013 isolates and assemble the reads to obtain the complete genome. We first report the whole-genome information of the mycoparasite Pestalotiopsis sp. strain cr013 (GenBank accession number: JACFXT010000000, BioProject ID: PRJNA647543, BioSample ID: SAMN15589943), and the genomic components and gene functions related to the mycoparasitism process were analyzed. This study provides a theoretical basis for understanding the lifestyle strategy of the mycoparasite Pestalotiopsis sp. and reveals the mechanisms underlying secondary metabolite diversity in the strain cr013.

Draft genome sequence of endolichenic fungus Dothichiza sp. strain YAFEF048, isolated from Usnea longissima on Haba Snow Mountain.

In this study, we report a draft genome sequence of the endolichenic fungus Dothichiza sp. strain YAFEF048, isolated from the lichen Usnea longissima on Haba Snow Mountain. The genome resource will support future research into the endolichenic lifestyle and potential secondary metabolite diversity of this fungus.

Inhibitory Activity of Enzyme Α-Glucosidase Ethanol Extract Combination Of Mareme Plant (Glochidion arborescens (Müll. Arg.) Boerl.) Leaves And Sala Plant (Cynometra ramiflora Linn) Leaves

Diabetes Mellitus (DM) is still one of the world's major health problems, contributing to many complications leading to increased morbidity and mortality. Different approaches have been performed to enhance the patient's quality of life. Over the past decade, due to a trend in herbal medicines, numerous plants have been claimed to be advantageous in alleviating DM features in pre-clinical research, including Mareme and Sala plants. Mareme and Sala leaves contain flavonoid compounds which are potential as antidiabetic agents. This study aimed to determine the in vitro inhibitory activity of the ethanolic extracts of both plants on the α-glucosidase enzyme that plays a pivotal role in diabetic pathophysiology. The inhibition potential of the combination of Mareme and Sala leaf ethanol extracts and the positive control, namely acarbose, were measured using an ELISA reader at 450 nm based on the formation of p-nitrophenol. The ELISA reader measurements showed that the combination of Mareme leaves and Sala leaf ethanol extract could not inhibit α-glucosidase activity in vitro, indicated by the IC50 calculation of 374.47 ppm. Nevertheless, our research revealed the presence of diverse secondary metabolites, including flavonoids, in both extracts, which could potentially be responsible for further pharmacological activities.

Insights into the Potential Role of Gordonia alkanivorans Strains in Biotechnologies

Members of many species of the genus Gordonia are known for their significant metabolic potential, including the ability to utilize compounds of different structures. The aim of the work was to study the ability of nine G. alkanivorans strains to degrade persistent organic pollutants and to analyze the genomic peculiarities of these strains. The genomes of nine Gordonia alkanivorans strains were sequenced and assembled. The utilization of these strains as alkane and benzoate degraders in environmental biotechnologies, coupled with their capacity to potentially produce diverse secondary metabolites, holds promising prospects for both environmental and pharmaceutical applications.