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Metabolomics using nontargeted tandem mass spectrometry can detect thousands of molecules in a biological sample. However, structural molecule annotation is limited to structures present in libraries or databases, restricting analysis and interpretation of experimental data. Here we describe CANOPUS (class assignment and ontology prediction using mass spectrometry), a computational tool for systematic compound class annotation. CANOPUS uses a deep neural network to predict 2,497 compound classes from fragmentation spectra, including all biologically relevant classes. CANOPUS explicitly targets compounds for which neither spectral nor structural reference data are available and predicts classes lacking tandem mass spectrometry training data. In evaluation using reference data, CANOPUS reached very high prediction performance (average accuracy of 99.7% in cross-validation) and outperformed four baseline methods. We demonstrate the broad utility of CANOPUS by investigating the effect of microbial colonization in the mouse digestive system, through analysis of the chemodiversity of different Euphorbia plants and regarding the discovery of a marine natural product, revealing biological insights at the compound class level. Unknown metabolites are classified from mass spectrometry data.

This study decisively evaluates the classification of four species of Euphorbia : Euphorbia ammak , Euphorbia fractiflexa , Euphorbia granulata , and Euphorbia hirta , collected from diverse habitats in Jazan region (Saudi Arabia). Our objective is to clearly define the interrelationships among these species by utilizing both traditional morphological analyses and cutting-edge chemotaxonomical methods. The morphological analysis examines various aspects of plant life, encompassing qualitative and quantitative parameters. Phytochemical analysis effectively measures total phenolics, alkaloids, flavonoids, saponins, and tannins. High-Performance Liquid Chromatography (HPLC) is employed to capture the phenolic patterns, thereby validating our chemotaxonomic approach. The HPLC analysis unequivocally identifies eleven phenolic and seven flavonoid compounds in the methanol extracts of the four Euphorbia taxa. The data collected from the studied Operational Taxonomic Units (OTUs) were meticulously organized into a binary matrix, establishing a similarity matrix and phenogram cluster. Duncan’s range test robustly determines the significance of interrelations among the species. The results demonstrate that all examined plant species are rich in phenolic constituents, albeit in varying concentrations. Notably, Euphorbia granulata stands out as the most transitional species among them. Taxonomically, our phenogram, based on taxonomic characteristics, reveals two distinct groups: the first group, at a distance of 1.90, includes Euphorbia ammak and Euphorbia fractiflexa , while the second group, at a distance of 1.52, encompasses the remaining two species. This study strongly recommends considering both adaptation and habitat type when conducting chemotaxonomic analyses of plant species.

Ingenol is a diterpenoid with unique architecture and has derivatives possessing important anticancer activity, including the recently Food and Drug Administration—approved Picato, a first-in-class drug for the treatment of the precancerous skin condition actinic keratosis. Currently, that compound is sourced inefficiently from Euphorbia peplus. Here, we detail an efficient, highly stereocontrolled synthesis of (+)-ingenol proceeding in only 14 steps from inexpensive (+)-3-carene and using a two-phase design. This synthesis will allow for the creation of fully synthetic analogs of bioactive ingenanes to address pharmacological limitations and provides a strategic blueprint for chemical production. These results validate two-phase terpene total synthesis as not only an academic curiosity but also a viable alternative to isolation or bioengineering for the efficient preparation of polyoxygenated terpenoids at the limits of chemical complexity.

The genus Euphorbia is one of the largest genera in the spurge family, with diversity in range, distribution, and morphology. The plant species in this genus are widely used in traditional medicine for the treatment of diseases, ranging from respirational infections, body and skin irritations, digestion complaints, inflammatory infections, body pain, microbial illness, snake or scorpion bites, pregnancy, as well as sensory disorders. Their successes have been attributed to the presence of diverse phytochemicals like polycyclic and macrocyclic diterpenes with various pharmacological properties. As a result, Euphorbia diterpenes are of interest to chemists and biochemists with regard to drug discovery from natural products due to their diverse therapeutic applications as well as their great structural diversity. Other chemical constituents such as triterpenoids have also been reported to possess various pharmacological properties, thus supporting the traditional uses of the Euphorbia species. These triterpenoids can provide potential leads that can be developed into pharmaceutical compounds for a wide range of medicinal applications. However, there are scattered scientific reports about the anticancer activities of these constituents. Harnessing such information could provide a database of bioactive pharmacopeia or targeted scaffolds for drug discovery. Therefore, this review presents an updated and comprehensive summary of the ethnomedicinal uses, phytochemistry, and the anticancer activities of the triterpenoids of Euphorbia species. Most of the reported triterpenoids in this review belong to tirucallane, cycloartanes, lupane, oleanane, ursane, and taraxane subclass. Their anticancer activities varied distinctly with the majority of them exhibiting significant cytotoxic and anticancer activities in vitro. It is, therefore, envisaged that the report on Euphorbia triterpenoids with interesting anticancer activities will form a database of potential leads or scaffolds that could be advanced into the clinical trials with regard to drug discovery.

Four out of five individuals rely on traditional medicine for their primary healthcare needs. Medicinal plants are endowed with diverse bioactive compounds to treat multidrug-resistant (MDR) microbes. So far, a less thorough examination has been made in this regard. This study aimed to evaluate antimicrobial activity and phytochemical screening of selected medicinal plants against MDR microbes. In vitro experimental study was carried out to evaluate antimicrobial effects and phytochemical screening of Rumex abyssinicus, Cucumis pustulatus, Discopodium penninervium, Lippia adoensis, Euphorbia depauperata, Cirsium englerianum, and Polysphaeria aethiopica against MDR bacteria and fungi. Aqueous and 80% methanolic extraction methods were employed for extraction. The susceptibility test, minimum inhibitory concentration, and minimum bactericidal or fungicidal concentration were measured using disc diffusion or broth micro-dilution as per the CLSI protocols. The 80% methanolic extraction method was a preferred method to aqueous. The phytochemical constituents identified were alkaloids, flavonoids, saponins, phenolic, tannins, terpenoidss, and cardiac glycosides. The hydroalcoholic extract demonstrated an appreciable antimicrobial role against MDR microbes with an MIC value of 1.0-128.0μg/ml and 11-29mm inhibition zone (IZ) in diameter. Extracts obtained from C. englerianum and E. depauperata showed a significant IZ ranged of 26-29mm on MRSA and Streptococcus pyogenes. MDR E. coli and K. pneumoniae showed 12-25mm and 23-28mm IZ in diameter, respectively. T. mentagraphytes was susceptible to all tested extracts. Moreover, S. pyogenes and K. pneumoniae were found the most susceptible bacteria to C. englerianum. Cirsium englerianum, L. adoensis, D. penninervium, and R. abyssinicus demonstrated remarkable antifungal effect against C. albicans and T. mentagrophytes, while R. abyssinicus showed the leading antifungal effect with 32 to 64μg/ml MIC values. The plant extracts have shown appreciable antimicrobial activities comparable to the currently prescribed modern drugs tested. Accordingly, further studies on clinical efficacy trial, safety, toxicity and affordability analyses have to be instigated promptly, so as to head to the final step to synthesize precursor molecules for new effective antimicrobials.

The seed oil of Euphorbia lathyris L. contains a series of macrocyclic diterpenoids known as Euphorbia factors. They are the current industrial source of ingenol mebutate, which is approved for the treatment of actinic keratosis, a precancerous skin condition. Here, we report an alcohol dehydrogenase-mediated cyclization step in the biosynthetic pathway of Euphorbia factors, illustrating the origin of the intramolecular carbon–carbon bonds present in lathyrane and ingenane diterpenoids. This unconventional cyclization describes the ring closure of the macrocyclic diterpene casbene. Through transcriptomic analysis of E. lathyris L. mature seeds and in planta functional characterization, we identified three enzymes involved in the cyclization route from casbene to jolkinol C, a lathyrane diterpene. These enzymes include two cytochromes P450 from the CYP71 clan and an alcohol dehydrogenase (ADH). CYP71D445 and CYP726A27 catalyze regio-specific 9-oxidation and 5-oxidation of casbene, respectively. When coupled with these P450-catalyzed monooxygenations, E. lathyris ADH1 catalyzes dehydrogenation of the hydroxyl groups, leading to the subsequent rearrangement and cyclization. The discovery of this nonconventional cyclization may provide the key link to complete elucidation of the biosynthetic pathways of ingenol mebutate and other bioactive macrocyclic diterpenoids.

Five previously undescribed tigliane diterpenes (1–4 and 7), along with three known tiglianes (5, 6, and 8) were isolated from the root extract of Euphorbia nicaeensis using chromatographic techniques. The structures of the isolated compounds were determined using spectroscopic techniques. The isolated compounds were tested for anti-HIV activity against HIV-1 NL4.3 and HIV-2 ROD strains. Two derivatives (2 and 8) exhibited significant anti-HIV activity, with IC50 values ranging from 1.10 to 7.47 µM. This study highlights the potential of E. nicaeensis root as a source of novel bioactive tigliane derivatives, warranting further investigation for possible use in HIV treatment.

The silver nanoparticles (AgNPs) were synthesized via green synthesis approach using Euporbia serpens Kunth aqueous extract. The synthesized AgNPs were characterized by UV-visible spectroscopy and Furrier Transformer Infra-Red spectroscopy to justify the reduction and stabilization of AgNPs from its precursors. AgNPs characteristic absorption peak was observed at 420 nm in the UV-visible spectrum. The SEM and TEM analysis demonstrated the spherical shape of the synthesized nanoparticles with particle sizes ranging from 30 nm to 80 nm. FTIR transmission bands at 2920 cm-1, 1639 cm-1, 1410 cm-1, 3290 cm-1, and 1085 cm-1 were attributed to C-H, C=O, C-C, N-H, and C-N functional groups, respectively. XRD peaks could be attributed to (111), (200), (220), and (311) crystalline plane of the faced-centered cube (FCC) crystalline structure of the metallic silver nanoparticles. The AgNPs showed good antibacterial activity against all the tested bacteria at each concentration. The particles were found to be more active against Escherichia coli (E. coli) with 20±06 mm and Salmonella typhi (S. typhi) with 18±0.5 mm zone of inhibition in reference to standard antibiotic amoxicillin with 23±0.3 mm and 20±0.4 mm zone of inhibition, respectively. Moderate antifungal activities were observed against Candida albicans (C. albicans) and Alternaria alternata (A. alternata) with zone of inhibitions 16.5 mm and 15 mm, respectively, compared to the standard with 23 mm of inhibition. Insignificant antifungal inhibition of 7.5 mm was observed against Fusarium gramium (F. gramium). All the tested concentrations of AgNPs showed comparable % RSA with the standard reference ascorbic acid in the range sixty percent to seventy five percent. The percent motility at 3 hours postincubation showed quick response and most Tetramorium caespitum were found deceased or paralyzed. Similarly, the percent mortality showed a linear response at concentration and time. It was observed that 1 μg/mL to 2 μg/mL concentration of AgNPs displayed a significant cytotoxic activity against Artemia salina with LD50 of 5.37 and 5.82, respectively.

Euphorbia is a large genus of the Euphorbiaceae family. Around 250 species of the Euphorbia genus have been studied chemically and pharmacologically; different compounds have been isolated from these species, especially diterpenes and triterpenes. Several reports show that several species have anti-inflammatory activity, which can be attributed to the presence of diterpenes, such as abietanes, ingenanes, and lathyranes. In addition, it was found that some diterpenes isolated from different Euphorbia species have anti-cancer activity. In this review, we included compounds isolated from species of the Euphorbia genus with anti-inflammatory or cytotoxic effects published from 2018 to September 2023. The databases used for this review were Science Direct, Scopus, PubMed, Springer, and Google Scholar, using the keywords Euphorbia with anti-inflammatory or cytotoxic activity. In this review, 68 studies were collected and analyzed regarding the anti-inflammatory and anti-cancer activities of 264 compounds obtained from 36 species of the Euphorbia genus. The compounds included in this review are terpenes (95%), of which 68% are diterpenes, especially of the types ingenanes, abietanes, and triterpenes (approximately 15%).

Psoriasis, an immune-mediated inflammatory skin disorder, seriously affects the quality of life of nearly four percent of the world population. Euphorbia helioscopia L. is the monarch constituent of Chinese ZeQi powder preparation for psoriasis, so it is necessary to illustrate its active ingredients. Thus, twenty-three diterpenoids, including seven new ones, were isolated from the whole herb of E. helioscopia L. Compounds 1 and 2, each featuring a 2,3-dicarboxylic functionality, are the first examples in the ent-2,3-sceo-atisane or the ent-2,3-sceo-abietane family. Extensive spectroscopic analysis (1D, 2D NMR, and HRMS data) and computational methods were used to confirm their structures and absolute configurations. According to the previous study and NMR data from the jatropha diterpenes obtained in this study, some efficient 1H NMR spectroscopic rules for assigning the relative configurations of 3α-benzyloxy-jatroph-11E-ene and 7,8-seco-3α-benzyloxy-jatropha-11E-ene were summarized. Moreover, the hyperproliferation of T cells and keratinocytes is considered a key pathophysiology of psoriasis. Anti-proliferative activities against induced T/B lymphocytes and HaCaT cells were tested, and IC50 values of some compounds ranged from 6.7 to 31.5 μM. Compounds 7 and 11 reduced the secretions of IFN-γ and IL-2 significantly. Further immunofluorescence experiments and a docking study with NF-κB P65 showed that compound 13 interfered with the proliferation of HaCaT cells by inhibiting the NF-κB P65 phosphorylation at the protein level.