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Phytochemical investigation of the EtOAc soluble fraction from leaves of Trichilia dregeana Sond. (Meliaceae) afforded naturally rare four new pentacyclic triterpenoids (1-4), together with five known pentacyclic analogs (5-8, and 11) and two steroids (9 and 10). Their structures were elucidated by extensive spectroscopic techniques such as 1D and 2D NMR and HRESIMS data analyses. The absolute configuration of 1 was determined by using the single-crystal X-ray diffraction analysis. The nitric oxide (NO) production inhibitory assay indicated that the EtOAc fraction as well as 4 and 7 inhibited the NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with the IC 50 values of 83.53 μg/mL and 81.31 and 85.71 μM, respectively. Compounds 1-4 are rare 19(10 → 9)abeo-euphane-type triterpenoids bearing a 3,10-ether bridge. To the best of our knowledge, this study is the first isolation of triterpenoids with the 3,10-ether bridge in their skeleton from the genus Trichilia, providing new insights into the chemodiversity of the terpenoids in T. dregeana., Competing Interests: Declaration of competing interest The authors declare no competing financial interest., (Copyright © 2024 Elsevier B.V. All rights reserved.)

In the search of cytotoxic dihydrochalcones, this investigation led to the isolation of seven compounds ( 1 - 7 ) from Eriosema glomeratum and the preparation of eight derivatives ( 8 - 15 ). The cytotoxicity of samples was evaluated against lung (A549), breast (MCF-7), and cervical (HeLa) human cancer cells. The CH 2 Cl 2 /MeOH extract of the aerial part had strong cytotoxicity against all cells [IC 50 11.2 (MCF-7), 8.4 (HeLa) and 13.1 (A549) μg/mL]. A strong activity was also displayed by the n -hexane fraction on MCF-7 (IC 50 11.2 μg/mL). The precursor 3 and the derivative 8 were specifically found as strong cytotoxic agents toward MCF-7 (7.6 μM) and HeLa (3.1 μM), respectively and were more effective than the positive control. Derivatives 8 (3.1 μM) and 9 (21.3 μM) against HeLa were most potent than their precursor 3 (23.7 μM). This is the first preparation of 8 - 14 as well as the cytotoxicity of 3 , 4 , 8 - 15 , fractions, and extract.

A new fructofuranoside glycerol, dryoptkirbioside (1), along with thirteen known compounds (2-14), was isolated from the MeOH extract of Dryopteris kirbi rhizomes by silica gel column chromatography, Sephadex LH-20 column chromatography, and semipreparative HPLC. The structure of the new compound was determined by analyses of its spectroscopic data including nuclear magnetic resonance (NMR), and high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and chemical conversions. The hexane-soluble portion and the EAF A fraction showed strong activities against lung (A549), breast (MCF-7), and cervical (HeLa) human cancer cell lines (IC 50 values ranging from 4.0 to 8.8 μg/mL). Aspidinol P (5) and aspidinol B (6) exhibited moderate to low cytotoxicity on the three cell lines (IC 50 values ranging from 20.4 to 58.7 μM). The MeOH extract and hexane-soluble portion had excellent activities against Staphylococcus aureus and Bacillus subtilis (MICs 11.7 and 23.4 μg/mL), whereas the AcOEt- and BuOH-soluble portions were significantly active on S. aureus (MICs 46.9 and 93.8 μg/mL). The main fractions EAF B , EAF C and nBF B displayed excellent activity against S. aureus (MICs 11.7 and 23.4 μg/mL). Aspidinol B (6) had significant activity, while aspidinol P (5) was moderately active against S. aureus and B. subtilis (MICs 42.0 and 89.5 μM)., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Background: Dacryodes edulis is a plant that belongs to the Burseraceae family. It is widely used traditionally alone or in association with other plants in Cameroonian folk medicine to cure wounds, fever, headaches, and malaria. The aim of this work was to investigate the leaves and stem bark of D. edulis with an emphasis on the antiplasmodial and cytotoxic effects of extracts, fractions, and isolated compounds., Methods: Extracts, fractions, and some isolated compounds were subjected to antiplasmodial activity screening in vitro against chloroquine-sensitive 3D7 and multidrug resistant Dd2 strains of Plasmodium falciparum using a SyBr Green fluorescence-based assay. The cytotoxicity of active extracts, fractions, and compounds was tested against mammalian Raw cell lines using an in vitro resazurin-based viability assay. The structures of the compounds were determined based on their NMR and MS data. The in vivo toxicity using female BALB/c mice was performed on the most active extract according to the protocol of OECD (2002), guideline 423., Results: The hydroethanolic extract from the leaves of D. edulis displayed good antiplasmodial activity with IC 50 values of 3.10 and 3.56 μg/mL respectively on sensitive (3D7) and multiresistant (Dd2) strains of P. falciparum. Of the sixteen compounds isolated, 3,3',4-tri-O-methylellagic acid (4) exhibited the highest antiplasmodial activity against PfDd2 strains with an IC 50 value of 0.63 μg/mL. All extracts, fractions, and isolated compounds demonstrated no cytotoxicity against Raw cell lines with CC 50  > 250 μg/mL. In addition, the most active extract on both strains of P. falciparum was nontoxic in vivo, with a LD 50 greater than 2000 and 5000 mg/kg. A phytochemical investigation of the stem bark and leaves of D. edulis afforded sixteen compounds, including two xanthones (1-2), three ellagic acid derivatives (3-5), one phenolic compound (6), one depside (7), one triglyceride (8), one auranthiamide acetate (9), one gallic acid derivative (10), four triterpenoids (11-14), and two steroids (15-16). Compounds 1, 2, 5, 7, 8, and 9 were herein reported for the first time from the Burseraceae family., Conclusion: This work highlights the good in vitro antiplasmodial potency of the hydroethanolic extract of the leaves of this plant and that of two isolated constituents (3,3',4-tri-O-methylellagic acid and ethylgallate) from the plant. These biological results support the use of D. edulis in traditional medicine against malaria., (© 2023. The Author(s).)

The phytochemical investigation of the MeOH and CH 2 Cl 2 -MeOH (1:1) extracts from the flowers and twigs of Helichrysumfoetidum (L.) Moench (Asteraceae), which showed antileishmanial and antiplasmodial activities during the preliminary screening, led to the isolation of four undescribed compounds, including two ent-beyer-15-ene-type diterpenoids, foetidumins A (1) and B (2), one flavonoid, foetidumin C (3) and one chalcopyrone, foetidumin D (4). Additionally, fourteen known compounds comprising, two ent-beyer-15-ene-type diterpenoids (5-6), six flavonoids (7-12), two steroids (13-14), three triterpenoids (15-17), and one glyceryl monostearate (18) were also isolated. The chemical structures of foetidumins A-D were fully elucidated by analyses of their spectroscopic data. The structure and the stereochemistry of foetidumin A (1) were confirmed by SC-XRD analyses. Among the tested compounds, foetidumin C (3), erythroxylol A (6), and kaempferol (7) displayed the highest antileishmanial potency with IC 50 values of 13.0, 11.8, and 11.1 μM, respectively. Foetidumin C (3) had no cytotoxicity toward Vero cells with the selectivity index > 3.59. Meanwhile, extracts of flowers and twigs had higher activity against Plasmodium falciparum chloroquine-sensitive (Pf3D7) strain with IC 50 values of 3.66 and 10.52 μg/mL, respectively., 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.)

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.)

A phytochemical study of the methanol extract of the fruit of Maesa lanceolata resulted in the isolation of a new alkenylbenzoquinone ( 1 ), alongside the known compounds ( Z )-2,5-dihydroxy-6-methyl-3-(pentadec-10'-enyl)-1,4-benzoquinone ( 2 ), 2,5-dihydroxy-6-methyl-3-(nonadec-14'-enyl)-1,4-benzoquinone ( 3 ), 2,5-dihydroxy-6-methyl-3-(tridecyl)-1,4-benzoquinone ( 4 ), (2 S ,3 S ,4 R ,2' R ,9E)-[2'-hydroxytetraeicosanoyl]-2-aminooctadec-9-ene-1,3,4-triol ( 5 ), monopalmitin (glyceryl palmitate) ( 6 ), lupeol ( 7 ), and 3- O -( β -D-glucopyranoside)- β -sitosterol ( 8 ). The structures of the compounds were established by the means of spectroscopic (1 D- and 2 D-NMR) and spectrometric techniques (MS). The isolated compounds were assessed for their antibacterial, cytotoxic, and antiradical activities. Compound 2 showed moderate activity against Staphylococcus warneri (DSMZ 20036), while the other compounds were inactive. The two quinones 1 and 2 were significantly cytotoxic, with IC 50 values of 0.005  µ M and 12.5  µ M respectively, and were weakly active towards DPPH radical (IC 50 >250  µ g/mL).

Ripe figs, barks, and wood of Ficus vallis-choudae are used in traditional medicine against several conditions including nausea and malaria. However, its use is still to be scientifically documented and validated. Hence, the aim of the present work was to evaluate the antiplasmodial activity of the dichloromethane-methanol (DCM-MeOH (1:1)) crude extract, their hexane, dichloromethane, ethyl acetate, and methanoli fractions, as well as the isolated chemical constituents. The chemical study of the DCM-MeOH (1:1) crude extract of F. vallis-choudae figs led to the isolation of fifteen (15) known compounds identified based on their spectroscopic data [one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), mass spectrometry] and by comparison of these data with those reported in the literature. Some of the isolated compounds were assessed in vitro for their antiplasmodial activity against Plasmodium falciparum chloroquine-sensitive 3D7 (Pf3D7) and multidrug-resistant Dd2 strains. The dichloromethane fraction exhibited very good antiplasmodial activity against both strains with IC 50 values of 13.86 μg/mL and 8.18 μg/mL, respectively. Among the tested compounds, wighteone (2) was the most active against P. falciparum 3D7 (IC 50  = 24.6 ± 1.5 μM) and Dd2 (IC 50  = 11.9 ± 2.4 μM) strains. The obtained results could justify the traditional uses of F. vallis-choudae against malaria. Wighteone appears to be the most active ingredient. However, further consideration of this compound as starting point for antimalarial drug discovery will depend upon its selectivity of action towards Plasmodium parasites. HIGHLIGHTS: • 15 (fifteen) compounds were isolated from the dichloromethane-methanol extract of Ficus vallis-choudae. • Their structures were determined on the basis of their spectroscopic data. • The dichloromethane fraction showed promising activities on the Pf3D7 and PfDd2 strains with IC 50 values of 13.86 and 8.18 µg/mL, respectively. • Wighteone was the most active compound against PfDd2 (IC 50  = 11.9 ± 2.4 μM)., (© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

The phytochemical investigation of the methanol extract of the stem bark of Gilbertiodendron dewevrei led to the isolation of two new secondary metabolites, 5,7-dihydroxy-4'-methoxyisoflavan-2,4-dione ( 1 ) and 23-hydroxy-2-tricosanone ( 2 ) along with 19 known compounds ( 3-21 ). The structure of these compounds were established by interpretation of their spectral data, mainly HR-TOFESIMS, 1 D NMR ( 1 H, 13 C and DEPT) and 2 D NMR ( 1 H- 1 H COSY, HSQC, HMBC, and NOESY), and by comparison with those reported in the literature. The methanol extract and some isolates were screened for their antiradical, antibacterial, and inhibitory properties against acetylcholinesterase.

Methanolic extracts of liana of Caesalpinia welwitschiana and leaves of C. bonduc were found to possess moderate antifeedant and ovicidal activities against Tuta absoluta . Bioassay-guided isolation of constituents from the most active fraction of C. welwitschiana led to the identification of four known compounds [isobonducellin 1a and bonducellin 1 b , intricatinol 2 , (-)-epigallocatechin-3- O -gallate 4 ] and one new constituent [welwitschianic acid 3 ]. The most active fraction of C. bonduc afforded two known constituents neocaesalpin L 5 and neocaesalpin A 6 . The isolated structures were elucidated on the basis of their MS, UV, IR and 1 & 2 D NMR spectra and by comparison with literature data. Compounds 2 , 4 - 6 were showed antifeedant and ovicidal properties against T. absoluta, some comparable to that of azadirachtin at 50, 100 and 200 ng/µl. Overall, the present study, conclude that the two species of the plant could be a promising source of eco-friendly botanical constituents.

A new alkaloid, manniindole 1 , together with four known compounds: aristolactam AII 2 , aristolactam BII 3 , piperolactam D 4 and polycarpol 5 were isolated from the crude extract EtOH-H 2 O (8:2) of the roots of Anonidium mannii by chromatographic separation. The structure elucidation was performed on the basis of a spectroscopic analysis (IR, HRESI MS, 1D and 2D NMR) as well as a comparison of their spectral data with those reported in the literature. For the first time, the crude extract and those isolated compounds were evaluated for their anti-schistosomal activity against Schistosoma mansoni and for cytotoxicity activity against Huh7 and A549 cells. Furthermore, they were also tested in vitro on the recent characterized Schistosoma mansoni NAD + catabolizing enzyme ( Sm NACE) for their impact on this enzyme which is localized on the outer surface of the adult parasite. Compound 2 displayed quite good worm killing capability, while 4 showed significant inhibition of Sm NACE.

The phytochemical investigation of the methanol extract of the bark of Croton oligandrus Pierre ex Hutch yielded a new clerodane-type diterpenoid crotoliganfuran ( 1 ) along with ten other compounds including 12-epicrotocorylifuran ( 2 ), lupeol ( 3 ), syringic acid ( 4 ), aleuritolic acid acetate ( 5 ), aleuritolic acid ( 6 ), scopoletin ( 7 ), geddic acid ( 8 ), β -sitosterol ( 9 ), vanilic acid ( 10 ) and stigmastane-3,6-dione ( 11 ). Their structures were established by spectroscopic means. The extract and all the isolates were screened for their inhibitory properties against butyrylcholinesterase and urease enzymes, respectively. The extract and compounds 1 , 4 and 7 displayed the most potent urease inhibitory properties with IC 50 values, 22.2, 26.7 and 28.5  µ M, respectively. Compound 9 was the most active of all the tested compounds against butyrylcholinesterase enzyme with an IC 50 value of 36.3  µ M.[Formula: see text].

Three previously undescribed indole alkaloids, named latifolianine A ( 1 ) and latifoliaindoles A and B ( 2 and 3 ), along with 10 known compounds ( 4 - 13 ), were isolated from the heartwood of Nauclea latifolia . Their structures were elucidated based on the analysis of their NMR and MS data. Latifolianine A ( 1 ) represents an unusual and unprecedented monoterpene indole alkaloid unit condensed with an ursane-type pentacyclic triterpenoid moiety. Plausible biogenetic routes toward latifolianine A ( 1 ) and latifoliaindoles A and B ( 2 and 3 ) were proposed. All the isolates were assessed in vitro for their inhibitory effects on Haemophilus influenzae . Naucleidinal ( 7 ) exhibited potent antibacterial activity (MIC value of 3.1 μg/mL) as compared to a reference drug, ciprofloxacin (MIC value of 1.6 μg/mL).

Background : Pathogenic yeasts resistance to current drugs emphasizes the need for new, safe, and cost-effective drugs. Also, new inhibitors are needed to control the effects of enzymes that are implicated in metabolic dysfunctions such as cancer, obesity, and epilepsy. Methods: The anti-yeast extract from Terminalia mantaly (Combretaceae) was fractionated and the structures of the isolated compounds established by means of spectroscopic analysis and comparison with literature data. Activity was assessed against Candida albicans , C. parapsilosis and C. krusei using the microdilution method, and against four enzymes of metabolic significance: glucose-6-phosphate dehydrogenase, human erythrocyte carbonic anhydrase I and II, and glutathione S -transferase. Results: Seven compounds, 3,3'-di- O -methylellagic acid 4'- O -α-rhamnopyranoside; 3- O -methylellagic acid; arjungenin or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid; arjunglucoside or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid glucopyranoside; 2α,3α,24-trihydroxyolean-11,13(18)-dien-28-oïc acid; stigmasterol; and stigmasterol 3- O -β-d-glucopyranoside were isolated from the extract. Among those, 3,3'-di- O -methylellagic acid 4'- O -α-rhamnopyranoside, 3- O -methylellagic acid, and arjunglucoside showed anti-yeast activity comparable to that of reference fluconazole with minimal inhibitory concentrations (MIC) below 32 µg/mL. Besides, Arjunglucoside potently inhibited the tested enzymes with 50% inhibitory concentrations (IC 50 ) below 4 µM and inhibitory constant (Ki) <3 µM. Conclusions: The results achieved indicate that further SAR studies will likely identify potent hit derivatives that should subsequently enter the drug development pipeline.

Phytochemical investigation of the seeds of Salacia longipes var. camerunensis led to the isolation of four sesquiterpenoid derivatives, salaterpene A (1) (1α,2β,8β-triacetoxy-6β,9β-dibenzoyloxy-4β-hydroxy-dihydro-β-agarofuran), salaterpene B (2) (1α,2β,8β-triacetoxy-9β-benzoyloxy-6β-cinnamoyloxy-4β-hydroxy-dihydro-β-agarofuran), salaterpene C (3) (1α,2β-diacetoxy-6β,9β-dibenzoyloxy-4β-hydroxy-dihydro-β-agarofuran) and salaterpene D (4) (2β-acetoxy-1α,6β-dibenzoyloxy-4β-hydroxy-9β-nicotinoyloxy-dihydro-β-agarofuran) together with two known compounds (5 and 6). The structures of the compounds were established by means of NMR spectroscopy. Compounds 1-4 and 6 were tested in vitro for their antiplasmodial activity against Plasmodium falciparum chloroquine-resistant strain W2. All the tested compounds exhibited a moderate potency with IC50 below 2.7 μM., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Phytochemical investigation of the figs of Ficus mucuso led to the isolation of three new isoflavone dimer derivatives, mucusisoflavones A-C (1-3), together with 16 known compounds. Some of the isolates were tested in vitro for their inhibitory properties toward β-glucuronidase and Plasmodium falciparum enoyl-ACP reductase (PfENR) enzymes. Compound 1 (IC₅₀) 0.68 μM) showed inhibitory activity on β-glucuronidase enzyme, while 3 (IC₅₀) 7.69 μM) exhibited a weak inhibitory activity against P. falciparum enoyl-ACP reductase (PfENR).

Two new sphingolipids mucusamide (1) and mucusoside (2) have been isolated from methanol soluble part of the stem bark of Ficus mucuso WELW., together with fifteen known secondary metabolites including cellobiosylsterol (3), β-sitosterol (4), stigmasterol (5), β-sitosterol 3-O-β-D-glucopyranoside (6), lupeol acetate (7), ursolic acid (8), procatechuic acid (9), 2-methyl-5,7-dihydroxychromone 8-C-β-D-glucoside (10), apigenin (11), (-)-epicatechin (12), (+)-catechin (13), N-benzoyl-L-phenylalanilol (14), α-acetylamino-phenylpropyl α-benzoylamino-phenylpropionate (15), asperphenamate (16) and bejaminamide (17). Structures of compounds 1 and 2 were elucidated by spectroscopic analysis and chemical methods.