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The species Bathysa gymnocarpa K.Schum is a tree belonging to the Rubiaceae family, endemic in Brazil. So far, there are reports neither of phytochemical work nor of biological evaluation of it. The analysis by High Performance Liquid Chromatography coupled to a Diode Array Detector and a tandem Mass Spectrometer with an Electrospray Ionization source (HPLC-DAD-ESI-MS/MS) of its crude extract allowed to characterize in a complex mixture, without isolation, fourteen compounds, being two as cinnamic acid derivatives, and the others as mono-, di- and triglycosilated derivatives of the flavonols quercetin and kaempferol. These compounds are reported for the first time in Bathysa spp.

Continued interest in the bioactive alkaloids led to the isolation of five undescribed alkaloids (1-5), ophiorglucidines A-E, and seven known analogues (6-12) from the water-soluble fraction of Ophiorrhiza japonica. The structures were elucidated based on spectroscopic data and quantum calculations as well as X-ray crystallographic analysis. The structure of 1 was characterized as a hexacyclic skeleton including a double bridge linking the indole and the monoterpene moieties, which is the first report of a single crystal with this type of structure. Moreover, the inhibitory effect of zwitterionic indole alkaloid glycosides on xanthine oxidase was found for the first time. The alkaloids 2 and 3, both of which have a pentacyclic zwitterionic system, were more active than the reference inhibitor, allopurinol (IC 50  = 11.1 μM) with IC 50 values of 1.0 μM, and 2.5 μM, respectively. Structure-activity relationships analyses confirmed that the carbonyl group at C-14 was a key functional group responsible for the inhibitory effects of these alkaloids., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Cordiera myrciifolia is an abundant species in Northeast Brazil that presents metabolites of biological/therapeutic interest. From this perspective, the present study aimed to investigate the chemical constituents and evaluate the in vitro antimicrobial activity of hexane (HECM) and ethanolic (EECM) extracts of C. myrciifolia leaves. The extracts were analyzed by chromatographic techniques (GC and UPLC) coupled with mass spectrometry. The antimicrobial activity of the extracts and the extracts combined with conventional drugs was evaluated by microdilution. The in vitro effect of the treatments on Candida's morphological transition was verified through cultivation in humid chambers. In HECM, 11 constituents including fatty acids, and triterpenes, including phytosterols, alkanes, tocols, and primary alcohols were identified. Triterpenes represented >40% of the identified constituents, with Lupeol being the most representative. In EECM, 13 constituents were identified, of which eight belonged to the class of flavonoids. High antibacterial activity of HECM was detected against Escherichia coli and Staphylococcus aureus, with Minimum Inhibitory Concentrations of 8 and 16 μg/mL, respectively. The combined activity was more effective when combined with Norfloxacin and Imipenem. In anti-Candida activity, the IC 50 of the extracts ranged from 36.6 to 129.1 μg/mL. There was potentiating effect when associated with Fluconazole. Both extracts inhibited the filamentous growth of C. tropicalis at a concentration of 512 μg/mL. C. myrciifolia extracts prove to be candidates for the development of new therapeutic formulations to treat bacterial and fungal infections., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Ethnopharmacological Relevance: Traditionally, the plant Morinda longissima Y.Z.Ruan (Rubiaceae) is used by ethnic people in Vietnam for the treatment of liver diseases and hepatitis., Aim of the Study: The study was designed to assess the efficacy of the 95% ethanolic extract of Morinda longissima roots (MLE) in experimental immune inflammation. The phytochemical variation of root extract and the chemical structures of natural compounds were also investigated using HPLC-DAD-HR-MS analysis., Materials and Methods: Three different doses (100, 200, and 300 mg/kg b.w.) of MLE were chosen to determine anti-inflammatory activity. The mice were given orally extracts and monitored their behavior and mortality for 14 days to evaluate acute toxicity. The volume of the paw and the histopathological evaluation were carried out. The polyphenolic phytoconstituents of MLE extract were identified using LC/MS analysis. The anti-inflammatory efficacy in silico and molecular docking simulations of these natural products were evaluated based on their cyclooxygenase (COX)-1 and 2 inhibitory effects., Results: This investigation showed the 95% ethanolic extract of Morinda longissima roots was found non-toxic up to 2000 mg/kg dose level in an acute study, neither showed mortality nor treatment-related signs of toxicity in mice. Eight anthraquinones and anthraquinone glycosides of Morinda longissima roots were identified by HPLC-DAD-HR-MS analysis. In the in vivo experiments, MLE was found to possess powerful anti-inflammatory activities in comparison with diclofenac sodium. The highest anti-inflammatory activity of MLE in mice was observed at a dose of 300 mg/kg body weight. The in silico analysis showed that seven out the eight anthraquinones and anthraquinone glycosides possess a selectivity index R COX-2/COX-1 lower than 1, indicating that these compounds are selective against the COX-2 enzyme in the following the order: rubiadin-3-methyl ether < morindone morindone-6-methyl ether < morindone-5-methyl ether < damnacanthol < rubiadin < damnacanthol-3-O-β-primeveroside. The natural compounds with the best selectivity against the COX-2 enzyme are quercetin (9), rubiadin-3-methyl ether (7), and morindone (4), with R COX2/COX1 ratios of 0.02, 0.03, and 0.19, respectively. When combined with the COX-2 protein in the MD research, quercetin and rubiadin-3-methyl ether greatly stabilized the backbone proteins and ligands., Conclusion: In conclusion, the anthraquinones and ethanolic extract of Morinda longissima roots may help fight COX-2 inflammation. To develop novel treatments for inflammatory disorders linked to this one, these chemicals should be investigated more in the future., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

To find structurally previously undescribed compounds with pharmacological effects from Prismatomeris tetrandra (Roxb.) K. Schum (Rubiaceae), thirteen undescribed tetrahydroanthraquinones (1⎼13) named prisconnatanones J⎼V and seven known anthraquinones (14⎼20) were isolated and characterized. The structures of these compounds were elucidated by detailed spectroscopic analyses, and their absolute configurations were established by modified Mosher's method and ECD calculations. The antitumor cell proliferative activities of prisconnatanones J⎼V were determined. Among them, prisconnatanones J possessed high antitumor cell proliferation in HGC27 cells (IC 50 , 0.792 μM) by blocking HGC27 cells in the S phase and significantly inducing apoptosis in HGC27 cells. Prisconnatanone J has no cytotoxicity to normal gastric cells line (GES-1) at 10 μM and showed a considerable selectivity for HGC27 cells. Prisconnatanone J can potentially inhibit tumor cell proliferation and should be further investigated., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Nauclea officinalis is a Chinese medicinal material with a high medicinal value, which contains various chemical constituents such as alkaloids, pentacyclic triterpenoids and their saponins, organic phenolic acids and their glycosides, iridoids, and flavonoids. It has antiviral, antibacterial, antipyretic, analgesic, anti-inflammatory, and immunoregulatory functions. This article systematically reviewed the reported chemical constituents and pharmacological effects of N. officinalis. According to the concept of quality markers, the quality markers of N. officinalis were predicted and analyzed from the aspects of plant kinship, specificity of chemical constituents, traditional drug efficacy, measurability of chemical constituents, plasma components, and different producing areas and harvest times, in order to provide a basis for the quality evaluation of N. officinalis.

Natural cross-linkers are extensively employed due to their low toxicity and biocompatibility benefits. Genipin acts as a precursor for producing blue colorants. The formation of these colorants involves the cross-linking reaction between genipin and primary amines present in amino acids, peptides, and proteins. Genipin is extracted from Gardenia jasminoides and Genipa americana. This article explains the cross-linking mechanism of genipin with proteins/polysaccharides to provide an overall understanding of its properties. Furthermore, it explores new sources of genipin and innovative methodologies to make the genipin recovery process efficient. Genipin increases food products' texture, gel strength, stability, and shelf life. The antibacterial, anti-inflammatory, and antioxidant properties of chitosan, gelatin, alginate, and hyaluronic acid increased after genipin cross-linking. Lastly, drawbacks, toxicity, and directions regarding the genipin cross-linking have also been addressed. The review article covers how to recover and cross-link genipin with biopolymers for industrial applications., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

Background: Chemotherapies target the PfEMP-1 and PfPKG proteins in Plasmodium falciparum, the parasite that causes malaria, in an effort to prevent the disease's high fatality rate. This work identified the phytochemical components of Nauclea latifolia roots and docked the chemical compounds against target proteins, and examined the in vivo antiplasmodial effect of the roots on Plasmodium berghei-infected mice., Methods: Standard protocols were followed for the collection of the plant's roots, cleaning, and drying of the roots, extraction and fraction preparation, assessment of the in vivo antiplasmodial activity, retrieval of the PfEMP-1 and PfPKG proteins, GCMS, ADME, and docking studies, chromatographic techniques were employed to separate the residual fraction's components, and the Swis-ADME program made it possible to estimate the drug's likeness and pharmacokinetic properties. The Auto Dock Vina 4.2 tool was utilized for molecular docking analysis., Results: The residual fraction showed the best therapeutic response when compared favorably to amodiaquine (80.5%) and artesunate (85.1%). It also considerably reduced the number of parasites, with the % growth inhibition of the parasite at 42.8% (D2) and 83.4% (D5). Following purification, 25 compounds were isolated and characterized with GCMS. Based on their low molecular weights, non-permeation of the blood-brain barrier, non-inhibition of metabolizing enzymes, and non-violation of Lipinski's criteria, betulinic and ursolic acids were superior to chloroquine as the best phytochemicals. Hence, they are lead compounds., Conclusion: In addition to identifying the bioactive compounds, ADME, and docking data of the lead compounds as candidates for rational drug design processes as observed against Plasmodium falciparum target proteins (PfEMP-1 and PfPKG), which are implicated in the pathogenesis of malaria, the study has validated that the residual fraction of N. latifolia roots has the best antiplasmodial therapeutic index., (© 2024. The Author(s).)

Two new indole alkaloids, naucleamide H ( 1 ) and (±)-19- O -butylangustoline ( 8 ), along with seven known alkaloids, 3,14-dihydroangustine ( 2 ), (-)-naucleofficine D ( 3a ), (+)-naucleofficine D ( 3b ), nauclefine ( 4 ), angustidine ( 5 ),19- O -ethylangustoline ( 6 ) and angustine ( 7 ) were isolated from the water extract of Nauclea officinalis . The structures of these compounds were established by spectroscopic analysis. Among them, the cytotoxicity of 1 , 2 , 6 and 8 were evaluated against six human cancer cell lines (HepG-2, SKOV3, HeLa, SGC 7901, MCF-7 and KB) in vitro for the first time with 5-fluorouracil as a positive control drug. The new compound 1 had a strong inhibitory effect on the proliferation of HepG-2 with an IC 50 value of 19.59 μg/mL. The new compound 8 had a strong inhibitory effect on HepG-2, SKOV3, HeLa, MCF-7 and KB, IC 50 value was 5.530, 23.11, 31.30, 32.42 and 37.26 μg/mL, respectively.

Two new anthraquinone derivatives sapranquinones A and B ( 1 and 2 ) together with two known biogenetically related anthraquinone derivatives ( 3 and 4 ) were isolated from the stems of Saprosma crassipes H. S. Lo. The structures of these compounds were elucidated using comprehensive spectroscopic methods. Compounds 1 - 4 were evaluated for their antibacterial activities and compounds 1 and 3 had a broad spectrum antibacterial activity against Staphylococcus albus , Escherichia coli , Bacillus cereus , Micrococcus tetragenus , and Micrococcus luteus with MIC values ranging from 1.25 to 5 μg/mL.

Genipa americana is a native plant of Brazil with potential applications in folk medicine. Whereas most of the phytochemical and pharmacological studies on this plant have focused on its fruits, the crude extracts of its leaves contain chemical metabolites that may have toxicity to organisms, which have yet to be investigated. This study aimed to determine the main groups of secondary metabolites in the aqueous extract of the leaves of G. americana by phytochemistry and qualitative HPLC, and to evaluate the possible toxicological effects and histopathological changes caused by this extract in zebrafish (Danio rerio) adults, through micronucleus test, nuclear abnormalities and histopathological analyses of gills and liver. While three metabolites of high intensity (phenolic compounds, flavonoids and triterpenes) were found in the phytochemical evaluation, the HPLC showed results compatible with flavonoids and iridoids, all belonging to common classes for this species and the Rubiaceae family. The acute toxicity test did not induce mortality or genotoxicity in zebrafish, but after exposure for 96 h, it was possible to observe injuries to the fish gill tissue, such as lamellar fusion, vasodilation and telangiectasia; in the liver, necrosis was visualized at 40 mg/L, and at higher concentrations (80 and 100 mg/L) induced sinusoidal widening was identified. In conclusion, the results demonstrated the toxic potential of this plant for aquatic species., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

Eight previously undescribed iridoid glycosides together with 20 known congeners were isolated from the aerial parts of Paederia scandens (Lour.) Merrill (Rubiaceae). Their structures incorporating absolute configurations were elucidated based on the comprehensive analyses of NMR data, HR-ESI-MS spectrometry, and ECD data. The potential anti-inflammatory activities of the isolated iridoids were evaluated in lipopolysaccharide-stimulated RAW 264.7 macrophages. Compound 6 significantly inhibited the production of nitric oxide with an IC 50 value of 15.30 μM. The results of immunoblotting, qPCR, and immunofluorescence staining assays revealed that compound 6 exhibited anti-inflammatory activity by suppressing nuclear translocation of NF-κB and reducing the expression of COX-2, iNOS, IL-1β, and IL-6. These results provide a basis for further development and utilization of P. scandens as a natural source of potential anti-inflammatory agents., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

A new glycoside, recurvataside ( 1 ) and six known compounds, quinovic acid ( 2 ), quinovic acid 28- O - β -D-glucopyranosyl ester ( 3 ), 3- O - β -D-glucopyranosylquinovic acid ( 4 ), 3- O - β -D-glucopyranosylquinovic acid 28- O - β -D-glucopyranosyl ester ( 5 ), pomolic acid ( 6 ), and ursolic acid ( 7 ) were isolated from aerial parts of Mussaenda recurvata . The structure of compound 1 was identified from its spectroscopic data and by comparison with the literature. Recurvataside represents the first occurrence of δ -oleanolic acid saponin bearing two D-glucose units at C-3 and C-28 in nature. This is the first time δ -oleanane-type saponin reported in the genus Mussaenda . Compounds 1-7 were evaluated the cytotoxicity against two cancer cell lines MCF-7 and HepG2. Among them, only compound 7 exhibited moderate activity against MCF-7 and HepG2 cell lines with IC 50 value of 16.97 ± 1.55 and 20.28 ± 1.00 μM, respectively. Compounds 1 - 7 were also tested for their inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 3 , 5 , and 7 showed significant reduction of nitrite accumulation in LPS-stimulated RAW 264.7 cells with the IC 50 values of 8.81 ± 0.48, 13.42 ± 0.84, and 18.37 ± 0.67 μM, respectively.

The root extract of Nauclea xanthoxylon (A.Chev.) Aubrév. displayed significant 50 % inhibition concentration (IC 50 s) of 0.57 and 1.26 μg/mL against chloroquine resistant and sensitive Plasmodium falciparum (Pf) Dd2 and 3D7 strains, respectively. Bio-guided fractionation led to an ethyl acetate fraction with IC 50 s of 2.68 and 1.85 μg/mL and subsequently, to the new quinovic acid saponin named xanthoxyloside (1) with IC 50 s of 0.33 and 1.30 μM, respectively against the tested strains. Further compounds obtained from ethyl acetate and hexane fractions were the known clethric acid (2), ursolic acid (3), quafrinoic acid (4), quinovic acid (5), quinovic acid 3-O-β-D-fucopyranoside (6), oleanolic acid (7), oleanolic acid 3-acetate (8), friedelin (9), β-sitosterol (10a), stigmasterol (10b) and stigmasterol 3-O-β-D-glucopyranoside (11). Their structures were characterised with the aid of comprehensive spectroscopic methods (1 and 2D NMR, Mass). Bio-assays were performed using nucleic acid gel stain (SYBR green I)-based fluorescence assay with chloroquine as reference. Extracts and compounds exhibited good selectivity indices (SIs) of >10. Significant antiplasmodial activities measured for the crude extract, the ethyl acetate fraction and xanthoxyloside (1) from that fraction can justify the use of the root of N. xanthoxylon in ethnomedicine to treat malaria., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Neolamarckia cadamba is an Indian traditional medicinal plant having various therapeutic potentials. In the present study, we did solvent-based extraction of Neolamarckia cadamba leaves. The extracted samples were screened against liver cancer cell line (HepG2) and bacteria (Escherichia coli). MTT cytotoxic assay was performed for in vitro analysis of extracted samples against the HepG2 cell lines and the normal human prostate PNT2 cell line. Chloroform extract of Neolamarckia cadamba leaves showed better activity with IC50 value 69 μg/ml. DH5α strain of Escherichia coli (E. coli) was cultured in Luria Bertani (LB) broth media and minimum inhibitory concentration (MIC) and Minimum bactericidal concentration (MBC) were calculated. Solvent extract chloroform showed better activity in MTT analysis and antibacterial screening and it was taken for characterization of phytocomposition by Fourier transform infrared (FTIR) and gas chromatography mass spectrometry (GC-MS). The identified phytoconstituents were docked with potential targets of liver cancer and E. coli. The phytochemical 1-(5-Hydroxy-6-hydroxymethyl-tetrahydropyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione shows highest docking score against the targets PDGFRA (PDB ID: 6JOL) and Beta-ketoacyl synthase 1(PDB ID: 1FJ4) and their stability was further confirmed by molecular dynamics simulation studies., (© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

From the Lasianthus bidoupensis stems, two new compounds, including one new 9,10-anthraquinone, lasibidoupin A ( 1 ), and one new 6,7-benzocoumarin, lasibidoupin B ( 2 ), together with one known compound, 11- O -methyldamnacanthol ( 3 ) were isolated using chromatographic method. Their structures were determined by extensive HRMS, and NMR assignments. Compound 3 was reported for the first time from this species. New compounds ( 1 & 2 ) were tested for the cytotoxicity against three human cancer cell lines (MCF-7, HeLa, and NCI-H460) by SRB assay. As results, 1 & 2 exhibited significant cytotoxic activity against all cancer cell lines (IC 50 ranged from 0.058   ± 0.003 to 0.177 ± 0.014 μM).

This article records for the first time the isolation of Ursolic acid from the leaves of Neolamarckia cadamba (Roxb.) Bosser (Family: Rubiaceae) using ultrasonic waves. This bioactive triterpenic acid was isolated without its isomer, oleanolic acid, in a very convenient way with good yield. The structure was identified by means of one dimensional Nuclear Magnetic Resonance (NMR) spectroscopic techniques like 1 H NMR, 13 C NMR, distortionless enhancement by polarization transfer (DEPT) and two dimensional NMR spectroscopic method for example, heteronuclear single quantum coherence (HSQC). It was also assayed for antidiabetic and antioxidant potencies. About 71.5 mg of pure ursolic acid was isolated from 2.6 grams of ethyl acetate soluble fraction using sono-maceration as an extraction technique.

Cyclotides are an intriguing class of structurally stable circular miniproteins of plant origin with numerous potential pharmaceutical and agricultural applications. To investigate the occurrence of cyclotides in Sri Lankan flora, 50 medicinal plants were screened, leading to the identification of a suite of new cyclotides from Geophila repens of the family Rubiaceae. Cycloviolacin O2-like (cyO2-like) gere 1 and the known cyclotide kalata B7 (kB7) were among the cyclotides characterized at the peptide and/or transcript level together with several putative enzymes, likely involved in cyclotide biosynthesis. Five of the most abundant cyclotides were isolated, sequenced, structurally characterized, and screened in antimicrobial and cytotoxicity assays. All gere cyclotides showed cytotoxicity (IC 50 of 2.0-10.2 μM), but only gere 1 inhibited standard microbial strains at a minimum inhibitory concentration of 4-16 μM. As shown by immunohistochemistry, large quantities of the cyclotides were localized in the epidermis of the leaves and petioles of G. repens . Taken together with the cytotoxicity and membrane permeabilizing activities, this implicates gere cyclotides as potential plant defense molecules. The presence of cyO2-like gere 1 in a plant in the Rubiaceae supports the notion that phylogenetically distant plants may have coevolved to express similar cytotoxic cyclotides for a specific functional role, most likely involving host defense.

Introduction: Sarcocephalus latifolius is one of the most used plants in West African traditional medicine to treat malaria., Objective: The aim is to establish a strategy to control the quality of herbal preparations made from S. latifolius., Method: A UHPLC-PDA method was developed for the determination and quantification of the two main bioactive compounds (angustoline and strictosamide) in various parts of the plant. Additionally, an LC-QToF with electrospray ionization method is described for the identification and confirmation of compounds in samples of different parts of the plant., Results: With the UHPLC-PDA method, separation was achieved within 5 min using a C18 column stationary phase at a temperature of 45°C and a gradient system with a mobile phase of water and acetonitrile, both containing 0.1% formic acid. The method was validated for linearity, accuracy, precision (repeatability and intermediate precision), limit of detection (LOD), and limit of quantification (LOQ). The LOD and LOQ of angustoline were found to be 0.3 and 0.8 μg/ml, respectively, and those of strictosamide were found to be 0.1 and 0.3 μg/ml, respectively. Using the LC-QToF method, 90 secondary metabolites, including four isolated compounds from the plant's roots, were identified from leaf, bark, and root samples of S. latifolius., Conclusion: This work is the first to propose a strategy to control the quality of herbal preparations made from S. latifolius. The developed method allows the quantification of the main bioactive compounds and the established chemical profile allows to distinguish the plant from any other species., (© 2022 John Wiley & Sons Ltd.)

Four new leucine-derived cytochalasans, possessing a 5,6,5,8-ring ( 1 ) and a 5,6,11-ring core ( 2 - 4 ), were isolated from a cultivated endophytic fungus Xylaria sp. strain WH2D4 (Xylariaceae). This fungus was isolated from leaves of the neotropical tree species Palicourea elata (Sw.) Borhidi (Rubiaceae) collected in Costa Rica. The chemical structures were determined by employing IR, MS as well as 1D- and 2D-NMR experiments. The stereochemistry at C-15 of compound 4 was determined by quantum calculations. The isolated compounds did not affect germination and growth of Trichoderma reesei and the opportunistic human fungal pathogen T. longibrachiatum .

An aliphatic alkene namely pentapentacontene ( 4 ) was isolated for the first time from a natural source, Gardenia aqualla , along with fourteen other compounds including nonacosanol ( 1 ), tetratriacontanol ( 2 ), octatriacontanol ( 3 ), β -sitosterol ( 5 ) and stigmasterol ( 6 ), daucosanol ( 7 ), ursolic acid ( 8 ), uvaol ( 9 ), 3 β ,19 α ,23 β ,24 α -tetrahydroxyurs-12-en-28-oic acid ( 10 ), lupenone ( 11 ), oleanolic acid ( 12 ), vanillin ( 13 ), vanillic acid ( 14 ) and D-mannitol ( 15 ). α -glucosidase inhibitory assay revealed that MeOH and EtOAc extracts of leaves had the best activity with IC 50 of 9.65 and 20.03 µg/ml respectively. All the tested compounds showed dose dependent inhibition of α -glucosidase and some of them were found to be comparable to acarbose. Compound 10 was the most potent with IC 50 = 1.72 μM. It also showed the most interesting antibacterial activity, against the isolate strain of S. typhi and P. aeruginosa and also exhibited the most significant antifungal activities against all the tested yeasts.

There is a previously neglected influence of geochemical conditions on plant phytochemistry. In particular, high concentrations of dissolved salts can affect their biosynthesis of natural products. Detoxification is most likely an important aspect for the plant, but additional natural products can also give it an expanded range of bioactivities. During the phytochemical analysis a Palicourea luxurians plant collected in a sulfate-rich environment (near the Río Sucio, Costa Rica) showed an interesting natural product in this regard. The structure of this compound was determined using spectroscopic and computational methods (NMR, MS, UV, IR, CD, optical rotation, quantum chemical calculations) and resulted in a megastigmane sulfate ester possessing a β-ionone core structure, namely blumenol C sulfate ( 1 , C 13 H 22 O 5 S). The levels of sulfur and sulfate ions in the leaves of the plant were determined using elemental analysis and compared to the corresponding levels in comparable plant leaves from a less sulfate-rich environments. The analyses show the leaves from which we isolated blumenol C sulfate ( 1 ) to contain 35% more sulfur and 80% more sulfate than the other samples. Antimicrobial and antioxidant activities of compound 1 were tested against Escherichia coli , E. coli ampR and Bacillus subtilis as well as measured using complementary in vitro FRAP and ATBS assays, respectively. These bioactivities are comparable to those determined for structurally related megastigmanes. The sulfur and sulfate content of the plant leaves from the sulfate-rich environment was significantly higher than that of the other plants. Against this background of salt stress, we discuss a possible biosynthesis of blumenol C sulfate ( 1 ). Furthermore, there appears to be no benefit for the plant in terms of extended bioactivities. Hence, the formation of blumenol C sulfate ( 1 ) probably primarily serves the plant detoxification process.

The methanolic extract of Mussaenda pubescens Dryand leaves exhibited significant anti-osteoclastogenic activity. Chemical investigation of M. pubescens led to the isolation of one new cycloartane saponin, mussaendoside X ( 1 ) along with eight known compounds: heinsiagenin A 3- O -[ α -L-rhamnopyranosyl-(1→2)- O - β -D-glucopyranosyl-(1→2)]- O - β -D-glucopyranoside ( 2 ), mussaendoside O ( 3 ), heinsiagenin A 3- O -[ α -L-rhamnopyranosyl-(1→2)- O - β -D-glucopyranosyl-(1→2)]- O - β -D-glucopyranosyl-(1→4)- O - β -D-glucopyranoside ( 4 ), mussaendoside G ( 5 ), mussaendoside U ( 6 ), shanzhiside methyl ester ( 7 ), barlerin ( 8 ) and musaenoside ( 9 ). Their structures were elucidated by extensive spectroscopic methods including 1D- and 2D-NMR as well as MS analysis and comparison with the literature. Cycloartane saponins 1 - 6 positively suppressed osteoclast formation in an anti-osteoclastogenic screening assay. Consequently, treatment of RANKL-stimulated RAW 264.7 cells with compounds 1 - 4 significantly decreased the number of osteoclasts in a concentration-dependent manner. Six compounds from M. pubescens , with the new cycloartane, mussaendoside X, were shown for the first time as potential effective inhibitors of osteoclastogenesis.

Ophiorrhiza plants (Family Rubiaceae) are known to produce diverse monoterpenoid indole alkaloids including camptothecin with potent antitumor activity. This review contains a summary of recent chemical studies reported over the past 10 years regarding alkaloids (monoterpenoid indole and tetrahydroisoquinoline alkaloids, and cyclopeptide) in Ophiorrhiza plants. In addition, the alkaloid biosynthetic pathways based on their reported structures were proposed., (© 2022. The Author(s).)

Ophiorrhiza japonica Bl. is a traditional Chinese materia medica widely used to treat several diseases. Chemical and pharmacological studies on O . japonica have been carried out; however, neither of them has been fully explored. In this study, an array of compounds was isolated from the title plant, including a new anthraquinone, ophiorrhizaquinone A ( 1 ), three alkaloids 2 - 4 and seven other compounds 5 - 11 with diverse structural types. Additionally, compounds 2 , 5 , 7 , 8 , 10 and 1 1 were isolated from the genus of Ophiorrhiza for the first time. Antioxidant bioassays in vitro using DPPH and ABTS were performed, and the results showed that compound 3 exhibited modest antioxidant activity with IC 50 values of 0.0321 mg/mL and 0.0319 mg/mL, respectively. An in silico study of PPARα agonistic activities of compounds 2 and 3 was conducted by molecular docking experiments, revealing that both of them occupied the active site of PPARα via hydrogen bonds and hydrophobic interactions effectively. This study enriched both the phytochemical and pharmacological profiles of O . japonica .

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called “yellow twig” Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a 1H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants’ defense strategy.

A pair of new diastereoisomers neolignans (1-2) and a new alkaloid (7) were isolated from the stems of Nauclea officinalis: naucleaoxyneolignoside A (1), naucleaoxyneolignoside B (2), (2S,3S)-javaniside (7), together with nine known compounds, 2S-3,3-di-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol (3), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol (4), nauclefine (5), angustidine (6), naucleoxoside A (8), naucleoxoside B (9), angustoline (10), (3S,19S)-3,14-dihydroangustoline (11), and (3S,19R)-3,14-dihydroangustoline (12).The structures of 1, 2 and 7 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparison of their data with those reported in the literature. The absolution configurations of 1, 2, 7,11 and 12 were confirmed by the quantum chemical CD calculation method. Compounds 1-9 showed weak to moderate inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro with IC 50 values comparable to that of dexamethasone. In addition, compounds 1-9 were evaluated for the antibacterial and cytotoxic effects, and the results revealed that these compounds showed no anti-bacterial activity, and compounds 3-6 showed modest cytotoxic activity., (Copyright © 2022. Published by Elsevier B.V.)

Three new polycyclic phenol derivatives, 2-acetyl-4-hydroxy-6H-furo [2,3-g]chromen-6-one ( 1 ), 2-(1',2'-dihydroxypropan-2'-yl)-4-hydroxy-6H-furo [2,3-g][1]benzopyran-6-one ( 2 ) and 3,8,10-trihydroxy-4,9-dimethoxy-6H-benzo[c]chromen-6-one ( 8 ), along with seven known ones ( 3 - 7 , 9 and 10 ) were isolated for the first time from the leaves of Spermacoce latifolia . Their structures were determined by spectroscopic analysis and comparison with literature-reported data. These compounds were tested for their in vitro antibacterial activity against four Gram-(+) bacteria: Staphyloccocus aureus ( SA ), methicillin-resistant Staphylococcus aureus ( MRSA ), Bacillus cereus ( BC ), Bacillus subtilis ( BS ), and the Gram-(-) bacterium Escherichia coli . Compounds 1 , 2 , 5 and 8 showed antibacterial activity toward SA , BC and BS with MIC values ranging from 7.8 to 62.5 µg/mL, but they were inactive to MRSA . Compound 4 not only showed the best antibacterial activity against SA , BC and BS , but it further displayed significant antibacterial activity against MRSA (MIC 1.95 µg/mL) even stronger than vancomycin (MIC 3.9 µg/mL). No compounds showed inhibitory activity toward E. coli . Further bioassay indicated that compounds 1 , 4 , 5 , 6 , 8 and 9 showed in vitro α -glucosidase inhibitory activity, among which compound 9 displayed the best α -glucosidase inhibitory activity with IC 50 value (0.026 mM) about 15-fold stronger than the reference compound acarbose (IC 50 0.408 mM). These results suggested that compounds 4 , 8 and 9 were potentially highly valuable compounds worthy of consideration to be further developed as an effective anti- MRSA agent or effective α -glucosidase inhibitors, respectively. In addition, the obtained data also supported that S. latifolia was rich in structurally diverse bioactive compounds worthy of further investigation, at least in searching for potential antibiotics and α -glucosidase inhibitors.

Objectives: This study aimed to evaluate the potential of aqueous extract from Mitracarpus frigidus aerial parts (MFAq) in the treatment of inflammation and oxidative stress, as well as to characterize its chemical constituents., Methods: Total phenolic and flavonoid contents were determined, and phytoconstituents were detected by ultra-fast liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry (UFLC-QTOF-MS). The antioxidant activity was evaluated by DPPH, TAC and β-carotene/linoleic acid assays. In-vitro anti-inflammatory activity, cell viability and cell cycle were performed in J774A.1 cell line. In-vivo anti-inflammatory activity was investigated by two ear oedema assays (croton oil and phenol)., Key Findings: Chlorogenic acid, clarinoside, quercetin-hexosylpentoside, rutin, kaempferol-3-O-rutinoside, kaempferol-rhamnosylhexoside, quercetin-pentosylrhamnosylhexoside, harounoside, 2-azaanthraquinone and sucrose were identified by UFLC-QTOF-MS. MFAq showed antioxidant activity, which was positively correlated to the content of phenolic compounds. MFAq significantly inhibited the production of nitric oxide, did not decrease viability in MTT assay (all concentrations) and showed no changes in membrane permeability and cell cycle of J774A.1 cell line. Furthermore, MFAq showed a reduction in ear oedema in all tested doses., Conclusion: MFAq was effective in some antioxidant and inflammatory parameters, in the experimental conditions that were used in the study. This is the first report of chemical composition and bioactivities from this extract., (© The Author(s) 2022. Published by Oxford University Press on behalf of the Royal Pharmaceutical Society. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.)

Phytochemical investigation of the roots of Rothmannia wittii led to the isolation of three new iridoid glucosides, named rothmanniosides A-C ( 1 - 3 ), and nine known compounds ( 4 - 12 ). Their structures, including their absolute configurations, were elucidated by thorough analysis of mass spectrometric and NMR spectroscopic data, together with CD calculations. Compounds 4 and 11 are reported from the Rubiaceae family for the first time.

Continued interest in bioactive alkaloids led to the isolation of two undescribed alkaloids, ophiorrhines F ( 1 ) and G ( 2 ), from the aerial parts of Ophiorrhiza japonica. Their structures were elucidated based on spectroscopic methods, electronic circular dichroism, and calculated NMR with DP4+ analysis. These two alkaloids represent key biological genetic intermediates in the formation of ring C in the ophiorrhines. Compound 1 exhibited good inhibition on LPS-induced B cell proliferation with an IC 50 value of 0.38 μM and showed significant selective inhibitory activity on a B cell proliferation response with a selective index of 548.42. A preliminary study indicated that 1 may have a new mechanism of immunosuppression.

The therapeutic efficacy of anthracycline antibiotic, doxorubicin (Dox), is hampered due to the dose-dependent cardiotoxicity. The objective of the study was to explore the counteraction of aqueous bark extract of Nauclea orientalis in Dox-induced cardiotoxicity in Wistar rats. The acute and subchronic toxicity study performed with 2.0 g/kg of the plant extract revealed biochemical and haematological parameters to be within the physiological range, and no histological alterations were observed in any organs isolated. Screening of plant extract for the protection of the myocardium from Dox-induced oxidative stress, inflammation, and apoptosis was performed on five groups of rats: control, plant extract control, Dox control (distilled water (D.H 2 O) 2 weeks + on the 11 th day single injection of Dox, 18 mg/kg), plant + Dox (2.0 g/kg plant extract 2 weeks + on the 11 th day Dox, 18 mg/kg), and positive control, dexrazoxane. A significant increase in cardiac biomarkers and lipid peroxidation ( p < 0.001) and a significant decrease in antioxidant parameters ( p < 0.001) were observed in the Dox control group. All these parameters were reversed significantly ( p < 0.05) in the plant-pretreated group. The histopathological assessment of myocardial damage provided supportive evidence for the biochemical results obtained. Inflammatory markers, myeloperoxidase, expression of TNF α and caspase-3, and DNA fragmentation (TUNEL positive nuclei) were significantly elevated ( p < 0.05), and expression of Bcl-2 was significantly decreased ( p < 0.05) in the Dox control; however, all these parameters were significantly reversed in the plant extract-treated group. In conclusion, the aqueous bark extract of Nauclea orientalis (2.0 g/kg) has the ability to attenuate the Dox-induced oxidative stress, inflammation, apoptosis, and DNA fragmentation in Wistar rats., Competing Interests: The authors declare that there is no conflict of interest regarding the publication of this paper., (Copyright © 2022 Jayasinghe A. N. Sandamali et al.)

α -Amylase is an enzyme involved in the breaking down of large insoluble starch molecules into smaller soluble glucose molecules. Catunaregam spinosa (Thunb.) Tirveng. (syn. Randia dumetorum (Retz.) Lam., Family: Rubiaceace) has been used as traditional medicine for the treatment of gastrointestinal problems, skin diseases, and diabetes. In this context, we studied the in vitro α -amylase inhibiting properties of methanol extracts of leaves and bark of C. spinosa . The methanol extract of bark was further fractionated into hexane, dichloromethane and ethyl acetate, and water-soluble fractions, and their α -amylase inhibitory activity was evaluated. In silico molecular docking and ADMET analysis of several compounds previously reported from the bark of C. spinosa were also performed. The in vitro α -amylase inhibition activity assay of the dichloromethane fraction of extract of bark (IC 50 : 77.17 ± 1.75  μ g/mL) was more potent as compared to hexane and ethyl acetate fractions. The in silico molecular docking study showed that previously reported compounds from the stem bark such as balanophonin, catunaregin, β -sitosterol, and medioresinol were bounded well with the active catalytic residue of porcine pancreatic α -amylase indicating better inhibition. The ADMET analysis showed the possible drug-likeness and structure-activity relationship of selected compounds. These compounds should be studied further for their potential α -amylase inhibition in animal models., Competing Interests: The authors declare no potential conflict of interest., (Copyright © 2021 Deepak Timalsina et al.)

The stems of Nauclea officinalis have been utilized as a crude drug in China, so other parts of the plant are abandoned, resulting in a waste of traditional Chinese medicine resources. To determine the distribution and content of the alkaloids, phenolic acids and iridoid in different organs (stem, branch, leaf and bark) of this plant, a reliable method has been established using LC-MS/MS. Nine constituents, namely strictosamide, vincosamide, chlorogenic acid, sweroside, naucleamide B, protocatechuic acid, pumiloside, vanillic acid and cryptochlorogenic acid, were simultaneously determined in 6 min. Meanwhile, the antipyretic, anti-inflammatory and analgesic activities were evaluated for comparative analysis of the pharmacological activity of different parts of N. officinalis. The results showed that the content of active components in other organs of N. officinalis was higher than that in stems, and the pharmacological effects of branches and leaves were also better. The established approach could be helpful for the quality control of N. officinalis, and also provide necessary information for the rational utilization of resources., (© 2021 John Wiley & Sons, Ltd.)

Breonadia salicina (Vahl) Hepper and J.R.I. Wood is widely used in South Africa and some other African countries for treatment of various infectious diseases such as diarrhea, fevers, cancer, diabetes and malaria. However, little is known about the active constituents associated with the biological activities. This study is aimed at exploring the metabolomics profile and antioxidant constituents of B. salicina . The chemical profiles of the leaf, stem bark and root of B. salicina were comprehensively characterized using proton nuclear magnetic resonance ( 1 H-NMR) spectroscopy and ultra-performance liquid chromatography with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). The antioxidant activities of the crude extracts, fractions and pure compounds were determined using the DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging and reducing power assays. A total of 25 compounds were tentatively identified using the UPLC-QTOF-MS. Furthermore, the 1 H-NMR fingerprint revealed that the different parts of plant had differences and similarities among the different crude extracts and fractions. The crude extracts and fractions of the root, stem bark and leaf showed the presence of α-glucose, β-glucose, glucose and fructose. However, catechin was not found in the stem bark crude extracts but was found in the fractions of the stem bark. Lupeol was present only in the root crude extract and fractions of the stem bark. Furthermore, 5- O -caffeoylquinic acid was identified in the methanol leaf extract and its respective fractions, while the crude extracts and fractions from the root and dichloromethane leaf revealed the presence of hexadecane. Column chromatography and preparative thin-layer chromatography were used to isolate kaempferol 3- O -(2″- O -galloyl)-glucuronide, lupeol, d-galactopyranose, bodinioside Q, 5- O -caffeoylquinic acid, sucrose, hexadecane and palmitic acid. The crude methanol stem bark showed the highest antioxidant activity in the DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity with an IC 50 value of 41.7263 ± 7.6401 μg/mL, whereas the root crude extract had the highest reducing power activity with an IC 0.5 value of 0.1481 ± 0.1441 μg/mL. Furthermore, the 1 H-NMR and UPLC-QTOF-MS profiles showed the presence of hydroxycinnamic acids, polyphenols and flavonoids. According to a literature survey, these phytochemicals have been reported to display antioxidant activities. Therefore, the identified hydroxycinnamic acid (caffeic acid), polyphenol (ellagic acid) and flavonoids (catechin and (epi) gallocatechin) significantly contribute to the antioxidant activity of the different parts of plant of B. salicina . The results obtained in this study provides information about the phytochemistry and phytochemical compositions of Breonadia salicina , confirming that the species is promising in obtaining constituents with medicinal potential primarily antioxidant potential.

Capirona (Calycophyllum spruceanum (Benth.) K. Schum.) and Bolaina (Guazuma crinita Lam.) are fast-growing Amazonian trees with increasing demand in timber industry. Therefore, it is necessary to determine the content of cellulose, hemicellulose, holocellulose and lignin in juvenile trees to accelerate forest breeding programs. The aim of this study was to identify chemical differences between apical and basal stem of Capirona and Bolaina to develop models for estimating the chemical composition using Fourier transform infrared (FTIR) spectra. FTIR-ATR spectra were obtained from 150 samples for each species that were 1.8 year-old. The results showed significant differences between the apical and basal stem for each species in terms of cellulose, hemicellulose, holocellulose and lignin content. This variability was useful to build partial least squares (PLS) models from the FTIR spectra and they were evaluated by root mean squared error of predictions (RMSEP) and ratio of performance to deviation (RPD). Lignin content was efficiently predicted in Capirona (RMSEP = 0.48, RPD > 2) and Bolaina (RMSEP = 0.81, RPD > 2). In Capirona, the predictive power of cellulose, hemicellulose and holocellulose models (0.68 < RMSEP < 2.06, 1.60 < RPD < 1.96) were high enough to predict wood chemical composition. In Bolaina, model for cellulose attained an excellent predictive power (RMSEP = 1.82, RPD = 6.14) while models for hemicellulose and holocellulose attained a good predictive power (RPD > 2.0). This study showed that FTIR-ATR together with PLS is a reliable method to determine the wood chemical composition in juvenile trees of Capirona and Bolaina., Competing Interests: The authors have declared that no competing interests exist.

Spermacoce verticillata (L.) G. Mey. is commonly used in the folk medicine by various cultures to manage common diseases. Herein, the chemical and biological profiles of S. verticillata were studied in order to provide a comprehensive characterization of bioactive compounds and also to highlight the therapeutic properties. The in vitro antioxidant activity using free-radical scavenging, phosphomolybdenum, ferrous-ion chelating and reducing power assays, and the inhibitory activity against key enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), tyrosinase, α-amylase and α-glucosidase of S. verticillata extracts (dichloromethane, ethyl acetate, methanol and water) were investigated. The highest total phenolic and flavonoid content were observed in the methanolic and aqueous extracts. Exhaustive 2DNMR investigation has revealed the presence of rutin, ursolic and oleanoic acids. The methanolic extract, followed by aqueous extract have showed remarkable free radical quenching and reducing ability, while the dichloromethane extract was the best source of metal chelators. The tested extracts showed notable inhibitory activity against cholinesterases (AChE: 1.63-4.99 mg GALAE/g extract and BChE: 12.40-15.48 mg GALAE/g extract) and tyrosinase (60.85-159.64 mg KAE/g extract). No inhibitory activity was displayed by ethyl acetate and aqueous extracts against BChE and tyrosinase, respectively. All the tested extracts showed modest α-amylase inhibitory activity, while only the ethyl acetate and aqueous extracts were potent against α-glycosidase. This study further validates the use of S. verticillata in the traditional medicine, while advocating for further investigation for phytomedicine development., (© 2021 Wiley-VHCA AG, Zurich, Switzerland.)

Lyaline ( 1 ) is a monoterpene indole alkaloid that was isolated in 1974 from Pauridiantha lyallii (Rubiaceae) in our laboratory and has not been reported elsewhere since then. Its structure was proposed on the basis of a very limited set of spectroscopic data (viz., 1 H NMR and EIMS) as a structurally bizarre harman-1,4-dihydropyridine derivative. A total synthesis of this proposed structure 30 years later proved this product to be highly unstable, and inconsistencies with the original limited spectroscopic data indicated that the structure proposed for lyaline was incorrect. Having in our laboratory the initial and unique lyaline sample, we decided to reinvestigate it using modern spectroscopic techniques, 47 years after its isolation. Our new spectroscopic data confirmed that the initially assigned harman-1,4-dihydropyridine structure was incorrect, instead establishing lyaline as the first naturally occurring nacycline analogue. This structure revision substantiates a type of chemical reactivity of strictosidine first reported in 1975.

Chemical and biological investigation of the Madagascar endemic plant Saldinia proboscidea led to the isolation of an isomer of artemisinin, (-)-6-epi-artemisinin ( 2 ). Its structure was elucidated using a combination of NMR and mass spectrometry. The absolute configuration was established by chemical syntheses of compound 2 as well as a new stereoisomer ( 3 ). The comparable bioactivities of artemisinin ( 1 ) and its isomer (-)-6-epi-artemisinin ( 2 ) revealed that this change in configuration was not critical to their biological properties. Bioactivity was assessed using an apoptosis induction assay, a SARS-CoV-2 inhibitor assay, and a haematin polymerization inhibitory activity (HPIA) assay. This is the first report of an artemisinin-related compound from a genus not belonging to Artemisia and it is the first isolation of an artemisinin-related natural product that is the opposite enantiomeric series relative to artemisinin from Artemisia annua .

Natural compounds are widely explored in industries, as a lead compound. Evaluating their toxicity is of utmost importance, as they may cause other side effects. The major hassles in evaluating the toxicity of compounds through in vivo and in vitro methods such as time, money, workforce, and use of animal models can be overcome by computational methods. Quantitative structure-activity relationship (QSAR) models predict the toxicity from the structure of a compound. In the present study, the methanolic extracts of three plants, namely, Carissa carandas, Canthium angustifolium, and Epiphyllum oxypetalum, were subjected to Gas Chromatography-Mass Spectrometry (GC-MS), in which 27 different compounds were identified. The compounds were evaluated for their toxicity through QSAR-Toxicity Estimation Software Tool (TEST) against multispecies - Daphnia magna , Pimephales promelas, Tetrahymena pyriformis, and rat (Oral). The study revealed that the order of toxicity of the natural compounds was D. magna > T. pyriformis > P. promelas > Rat (Oral). All the compounds were non-bioaccummulative, while most of them were developmental toxicants. Only one compound (Dasycarpidan-1-methanol, acetate (ester)) was a mutagen. Further studies of the compounds on in vivo models are recommended after in silico analysis, for exploration in different industries.

A new indole alkaloid, namely naucleofficine H ( 1 ), was obtained from the aqueous extract of Nauclea officinalis , together with four known alkaloids, vincosamide ( 2 ), strictosamide ( 3 ), angustoline ( 4 ) and pumiloside ( 5 ). Their structures were characterized by analyzing their physicochemical data including NMR, and HRMS. In addition, five compounds were tested for their proliferation activities. The expression of vascular endothelial growth factor (VEGF), extra-cellular signal-regulated protein kinase 1 and 2 (ERK) and phosphorylation of ERK 1/2 (p-ERK) were also detected in HUVEC treated withbioactive compounds using western blotting. The result showed that these compounds could promote HUVEC cell proliferation. Compounds 3 and 5 could up-regulate VEGF and p-ERK in HUVEC.

In Rwanda, the roots of Pentas longiflora Oliv. (Rubiaceae) have been used for a long time to treat Pityriasis versicolor. However, many people reported the use of leaves instead of roots. This research was conducted to compare the phytochemical composition and establish chromatographic methods for the standardization of roots and leaves extracts of P. longiflora. During this process, three new pentalongin glycosides (pentalonginoside A, pentalonginoside B, and pentalonginoside C) and two known glycosides of the same type (harounoside and clarinoside), as well as rutin, luteolin-7-rutinoside were isolated from methanol extract of leaves. In addition, pentalongin and psychorubrin, previously isolated from ethylacetate roots extract, were also identified in Pentas longiflora ethylacetate leaves extract. The presence of the antifungal compound pentalongin in leaves may explain the traditional use of leaves in the treatment of Pytiriasis versicolor. Furthermore, harounoside, psychorubrin, and pentalongin were selected as markers for HPLC fingerprints of MeOH extract. The accuracy and risk profile demonstrated the reliability of the validated method. In general, considerable variations of concentration in plant metabolites, including pentalongin, were observed between samples from different sites. The content in pentalongin (expressed as juglone) in collected samples ranged between 1.7 and 70.0 mg/100 g. The highest concentration (70.0 ± 17 mg/100 g) was registered in the cultivated samples from Mukoni. This important variation of pentalongin concentrations according to sampling sites, shows that in order to guarantee equivalent efficacy, finished products with P. longiflora should be standardized based on their pentalongin content., (Copyright © 2021. Published by Elsevier B.V.)

Medicinal plants are a potential source of new antifungal agents to combat the development of drug-resistant fungi. This study aims to investigate the aerial parts of Alternanthera sessilis (Amaranthaceae) and Ipomoea aquatica (Convolvulaceae), and the leaves of Catunaregam spinosa (Rubiaceae) and Tradescantia spathacea (Commelinaceae) for antifungal activity and cytotoxicity. The plant materials were extracted sequentially using hexane, chloroform, ethyl acetate, ethanol, methanol, and distilled water. The antifungal activity was evaluated against four species of yeasts and two species of filamentous fungi using a colorimetric broth microdilution method. The toxicity of the extracts was assessed using African monkey kidney epithelial (Vero) cells. All 24 extracts from the four medicinal plants showed inhibitory activity against all fungal species, except Aspergillus fumigatus, with a minimum inhibitory concentration range of 0.04-2.50 mg/mL. The antifungal activity of these plants was more prominent on the yeasts than the filamentous fungi. Generally, the less polar extracts (hexane, chloroform, and ethyl acetate) of the plants had stronger antifungal activity than the more polar extracts (ethanol, methanol, and water). In contrast, toxicity assessment revealed that the less polar extracts showed relatively higher toxicity towards the Vero cells than the more polar extracts. The lowest median cytotoxic concentration was shown by the chloroform extract of A. sessilis (17.4 ± 0.4 μg/mL). All water extracts, the methanol extract of I. aquatica, and the ethyl acetate, ethanol, and methanol extracts of T. spathacea did not show significant toxicity (P>0.05) towards the Vero cells. The results suggested that Tradescantia spathacea has the most promising potential for pharmaceutical developments due to its broad spectrum and selective activity against human fungal pathogens.

Ethnopharmacological Relevance: Ophiorrhiza rugosa var. prostrata is a traditional medicinal plant used by the indigenous and local tribes (Chakma, Marma and Tanchangya) of Bangladesh for the management of chest pain, body ache, and earache. However, the knowledge of anti-nociceptive and anti-inflammatory potentials of this plant is scarce., Aim of the Study: Therefore, we scrutinized the anti-nociceptive and anti-inflammatory properties of O. rugosa leaves along with its possible mechanism(s) of action using chemical and heat-induced pain models., Methods and Materials: O. rugosa was extracted using 100% ethanol (EEOR) followed by exploring phytochemicals and assessing acute toxicity. To determine anti-nociceptive potentials, chemical-induced (acetic acid and formalin) and heat-induced (hot plate and tail immersion) nociceptive models were followed. To investigate the possible involvement of opioid receptors during formalin, hot plate, and tail immersion tests, naltrexone was administered whereas methylene blue and glibenclamide were used to explore cGMP involvement and ATP-sensitive K + channel pathways, respectively. Moreover, the anti-inflammatory potential was assessed using the carrageenan-induced paw edema test model. Motor behaviours of EEOR were assessed by the open-field test. Finally, bioactive constituents (identified by GC-MS) from O. rugosa were subjected to molecular docking and ADME/t analysis to evaluate its potency and safety., Results: During chemical-induced and heat-induced pain models, EEOR exhibited significant and effective nociception suppression at all experimental doses (200 and 400 mg/kg). Also, the administration of naltrexone corroborated the association of opioid receptors with the anti-nociceptive activity by EEOR. Similarly, cGMP and ATP-sensitive K + channel pathways were also found to be involved in the anti-nociceptive mechanism. Furthermore, significant and dose-dependent inhibition of inflammation induced by carrageenan was recorded for EEOR. Both doses of EEOR did not affect the animal's locomotor capacity in the open-field test. Besides, in silico test identified the key compounds (loliolide, harman, squalene, vitamin E, and gamma-sitosterol) that inhibited some particular receptors regarding pain and inflammation., Conclusion: This research exposes central and peripheral pain intervention as well as anti-inflammatory activity of O. rugosa. Also, the identified compounds from this plant support its activities by effectively inhibiting anti-nociceptive and anti-inflammatory receptors. Overall, these outcomes valorize the ethnomedicinal efficacy of O. rugosa in managing various painful conditions., (Copyright © 2021 Elsevier B.V. All rights reserved.)

An unusual, new anthracene natural product named filamentos A ( 1 ), two new anthraquinone derivatives named filamentos B ( 2 ) and C ( 3 ), together with sixteen known compounds ( 4 - 19 ), were isolated from the roots of the tree Prismatomeris filamentosa . Their structures were identified by analysis of mass and spectroscopic data (IR, 1D and 2D NMR). Twelve metabolites ( 1 - 6 , 9 , 12 - 14 , 16 - 17 ) showed moderate antibacterial activities against a wide range of Gram-positive and Gram-negative bacteria such as B . subtilis , B . cereus , S . aureus , E . coli , P . aeruginosa and S . sonnei .

In this study, we performed an anatomical analysis of the polysporangiate anthers and the development of pollen in Isertia laevis (Rubiaceae) with the aim to elucidate the internal structure of these atypical anthers. For this purpose, flowers in successive stages of development were dissected and the anthers were processed for conventional anatomical analysis. The material was examined using light microscopy and scanning electron microscopy. The present study shows that the anthers of Isertia laevis have two thecae divided into multiple microsporangia. This division is due to the presence of transverse and longitudinal septa formed of parenchyma and idioblasts with crystals. The septa appear together with the microsporangia and remain in the mature anther, even developing fibrous thickening. As the anther matures, the idioblasts in the septa accumulate crystals until they break, facilitating the separation of the septa from the outer wall of the theca, and thus apparently assisting the process of dehiscence. The mature anther opens through the longitudinal dehiscence of each theca. In addition to the anatomy of the anther, the development and morphology of the pollen, and the presence of orbicules are described. The structure of the anthers of I. laevis is discussed with other polysporangiate species in the Rubiaceae and angiosperms.

Background: antibiotic resistance encourages the development of new therapies, or the discovery of novel antibacterial agents. Previous research revealed that Myrmecodia pendans (Sarang Semut) contain potential antibacterial agents. However, specific proteins inhibited by them have not yet been identified as either proteins targeted by antibiotics or proteins that have a role in the quorum-sensing system. This study aims to investigate and predict the action mode of antibacterial compounds with specific proteins by following the molecular docking approach., Methods: butein ( 1 ), biflavonoid ( 2 ), 3″-methoxyepicatechin-3- O -epicatechin ( 3 ), 2-dodecyl-4-hydroxylbenzaldehyde ( 4 ), 2-dodecyl-4-hydroxylbenzaldehyde ( 5 ), pomolic acid ( 6 ), betulin ( 7 ), and sitosterol-(6'- O -tridecanoil)-3- O - β -D-glucopyranoside ( 8 ) from M. pendans act as the ligand. Antibiotics or substrates in each protein were used as a positive control. To screen the bioactivity of compounds, ligands were analyzed by Prediction of Activity Spectra for Substances (PASS) program. They were docked with 12 proteins by AutoDock Vina in the PyRx 0.8 software application. Those proteins are penicillin-binding protein (PBP), MurB, Sortase A (SrtA), deoxyribonucleic acid (DNA) gyrase, ribonucleic acid (RNA) polymerase, ribosomal protein, Cytolysin M (ClyM), FsrB, gelatinase binding-activating pheromone (GBAP), and PgrX retrieved from UniProt. The docking results were analyzed by the ProteinsPlus and Discovery Studio software applications., Results: most compounds have Pa value over 0.5 against proteins in the cell wall. In nearly all proteins, biflavonoid ( 2 ) has the strongest binding affinity. However, compound 2 binds only three residues, so that 2 is the non-competitive inhibitor., Conclusion: compound 2 can be a lead compound for an antibacterial agent in each pathway.

The hydro-distilled volatile constituents from the stem with leaf and flower of Neanotis lancifolia (Hook.f.) W.H.Lewis (Rubiaceae) were investigated for the first time by using gas chromatography equipped with a flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC-MS). Forty-two and twelve compounds were identified from the stem with leaf and flower parts oils, respectively, representing 98.5% and 97.1% of the total oil constituents, respectively. The major constituents were identified as linalool (35.9% stem with leaf; 23.3% flower) and borneol (15.0% stem with leaf; 29.2% flower). The volatile oils of both parts of the plant N. lancifolia were found to be rich in oxygenated monoterpene type of constituents.

Objectives: Evaluation of the in-vivo anti-inflammatory activity of the methanolic extract obtained from the aerial parts of Mitracarpus frigidus (MFM) in the infection caused by two Salmonella strains and its chemical fingerprint by UFLC-quadrupole time of flight-MS., Methods: The efficacy of MFM was investigated in a classical in-vivo Salmonella infection mouse model. A Salmonella reference strain (ATCC 13311) and a clinical isolate were used to infect mice and then MFM was orally administered during 14 days. At the end of the treatment with MFM, the infection and inflammatory levels were assayed., Key Findings: MFM treatment showed a significant reduction in mice mortality by Salmonella infection and, also, did not cause alterations in the liver function. Inhibitions of inflammatory and oxidative stress mediators [malondialdehyde (MDA), catalase, and metalloproteinase] were possibly involved in the observed effects. Chlorogenic acid, clarinoside, quercetin-pentosylhexoside, rutin, kaempferol-3O-rutinoside, kaempferol-rhamnosylhexoside and 2-azaanthraquinone were identified in MFM., Conclusions: MFM was effective in some inflammatory parameters, in the experimental conditions that were used in the study. The results presented in this study and the previous in-vitro anti-Salmonella activity reported by our research group reinforce the importance of MFM studies to considerer it as an alternative treatment for salmonellosis., (© The Author(s) 2020. Published by Oxford University Press on behalf of Royal Pharmaceutical Society. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.)

Ethnopharmacological Relevance: The leaf of Sarcocephalus latifolius is known to be used traditionally by the Fulanis in Nigeria to deworm animals. As helminthosis remains a major constraint to profitable livestock production worldwide, a precarious situation aggravated by the advent of resistant parasites, the discovery of new anthelmintics is a priority, necessitating exploration of medicinal plants for their anthelmintic principles., Aim of the Study: To identify and characterise compounds with anthelmintic activity from the leaf of Sarcocephalus latifolius., Materials and Methods: Powdered S. latifolius leaves were extracted by successive maceration with n-hexane, chloroform and acetone. The dried extracts were evaluated for anthelmintic activity against Haemonchus placei adult worms, and the most active extract was subjected to bioassay-guided chromatographic separations. The isolated compounds were evaluated for cytotoxicity against the mammalian HeLa and MC3T3-E1 cell lines, using alamar blue and CellTitreGlo TM to quantify cell viability. LC 50 values were computed from the in vitro anthelmintic activity data by fitting to a non-linear regression equation (variable slope). Isolated compounds were characterized using spectroscopic and mass spectrometric analyses., Results: Anthelmintic activity LC 50 values for n-hexane, chloroform and acetone extracts were 47.85, 35.76 and 5.72 (mg/mL), respectively. Chromatographic separation of acetone extract afforded two bioactive epimers, identified as vincosamide (LC 50 14.7 mg/mL) and strictosamide (LC 50 12.8 mg/mL). Cytotoxicity evaluation showed that, below 200 μg/mL (400 μM), neither compound was toxic to the HeLa or MC3T3-E1 cells., Conclusion: Vincosamide and strictosamide could serve as novel scaffolds for the development of anthelmintic derivatives with improved potency and helminth selectivity., (Copyright © 2020 Elsevier B.V. All rights reserved.)