Pyrroloquinolones B-F: Five unusual alkaloids from Vernonia glabra (Steetz) Vatke (Asteraceae).

Five unusual alkaloids featuring a pyrrolo[1,2-a]quinolone skeleton (pyrroloquinolones B-F, 1-5) were isolated from the ethanol extract of the whole plant of Vernonia glabra (Steetz) Vatke, along with sixteen known compounds. Their structures were established by means of spectroscopic (1D and 2D NMR, UV, IR, and ECD) and high resolution mass spectrometric techniques as well as by comparison of their spectroscopic data with those reported in the literature. The ethanol extract and some isolated compounds were assessed for their antibacterial activity against four bacterial strains. The extract was significantly active against Staphylococcus aureus ATCC1026 and S. epidermidis ATCC35984 (MIC = 64 µg/mL). All the tested compounds showed moderate activity against S. epidermidis (16 ≤ MIC ≤ 64 µg/mL). Furthermore, this is the first report on tricyclic pyrrolo[1,2-a]quinolone alkaloids from a plant source. A biosynthetic pathway for the formation of these compounds is also proposed.

Structure elucidation of olasubscorpioside C, a new rotameric biflavonoid glycoside from the stem barks of Olax subscorpioidea (Oliv).

From the n-butanol soluble fraction of the ethanol extract of the medicinal plant Olax subscorpioidea, a previously unreported rotameric biflavonoid glycoside constituted of 4'-O-methylgallocatechin-(4α → 8)-4'-O-methylgallocatechin as aglycone named olasubscorpioside C (1) along with the known 4'-O-methylgallocatechin (2) were isolated. Their structures were determined on the basis of spectrometric and spectroscopic techniques including HRFABMS, 1 H and 13 C NMR, DEPT 135o , HSQC, HMBC, ROESY, and CD followed by comparison with the reported data.

Mimonoside D: a new triterpenoid saponin from Mimosa diplotricha Sauvalle (Fabaceae).

A new triterpenoid saponin (Mimonoside D: 3-O-α-L-arabinopyranosyl-3ß-hydroxyolean-12-en-28-oic acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D- glucopyranoside ester (1)) was isolated from the aerial parts of Mimosa diplotricha Sauvalle together with nine known compounds: 7,4'-dihydroxyflavone (2), kaempferol (3), lupeol (4), betulinic acid (5), ß-sitosterol (6), ß-sitosterol-3-O-ß-D-glucopyranoside (7), lutein (8), 5,2'-dihydroxy-7,4',5'-trimethoxyflavone (9) and vitexin (10). Their structures were elucidated on the basis of spectroscopic (1 D and 2 D nuclear magnetic resonance) and high-resolution mass spectrometric data as well as by comparison of their spectral data with those of related compounds. Compounds 2, 7 and 8 had already been isolated from M. diplotricha, while compounds 3, 4, 5 and 6 have been isolated from other Mimosa species. Compound 2 moderately inhibited Proteus mirabilis (MIC = 32 µg/mL), weakly inhibited Pseudomonas aeruginosa (MIC = 64 µg/mL) and very weakly inhibited Staphylococcus aureus (MIC = 128 µg/mL) and Enterococus faecalis (MIC = 128 µg/mL).

New bioactive flavonoid glycosides with antioxidant activity from the stem bark of Olax subscorpioidea Oliv.

A previously unreported gallocatechin glycoside, (2 R,3S) 4'-O-methyl-gallocatechin-3-O-α-ʟ-rhamnopyranoside (1) and an unseparable mixture of two previously undescribed dihydromyricetin glycosides, (2 R,3R) 4'-O-methyl-dihydromyricetin-3-O-α-ʟ-rhamnopyranoside (2a) and (2 R,3S) 4'-O-methyl-dihydromyricetin-3-O-α-ʟ-rhamnopyranoside (2 b) along with three known compounds were isolated from the n-butanol soluble fraction of the stem bark of Olax subscorpioidea Oliv. Their structures were elucidated by detailed spectroscopic analyses, including 1H NMR, 13C NMR, 1H-1H COSY, HSQC, HMBC, NOESY, HR-ESI-MS and chemical methods. The crude ethanol extract, the fractions, and some of the isolated compounds were screened for their antioxidant and antibacterial activities. They showed significant antioxidant activities with EC50 ranging from 6.29 to 18.19 µg/mL in 2,2-diphenyl-1-picrylhydrazyl (DPPH) method and EC50 ranging from 85.77 to 86.39 mmol FeSO4/g in ferric reducing antioxidant power (FRAP) methods compared with 2.29 µg/mL and 3.52 mmol FeSO4/g for the positive control (ʟ-ascorbic acid). Nevertheless, no inhibition was observed against the tested bacterial strains at a MIC less than 256 µg/mL.

Bioactive Arylnaphthalide Lignans from Justicia depauperata.

Eleven previously undescribed arylnaphthalide lignans (1-11) together with seven known compounds were isolated from the whole plant of Justicia depauperata. The structures of 1-11 were elucidated by spectroscopic analysis and mass spectrometry. Compounds 6 (IC50 = 4.1 µM) and 9 (IC50 = 9.5 µM) displayed cytotoxic activity against the KB-3-1 cervical carcinoma cell line. This report provides an insight into the conformational equilibria occurring in the arylnaphthalide lignan constituents of this plant.

Chemotaxonomy and Antibacterial Activity of the Extracts and Chemical Constituents of Psychotria succulenta Hiern. (Rubiaceae).

The use of natural products for medicinal purposes is becoming more and more common nowadays, as evidenced by the presence in plants of secondary metabolites with different potentials such as antioxidant and antibacterial properties. We evaluated in this work the antimicrobial activities of the extracts and some isolated compounds from the seeds of Psychotria succulenta Hiern. (Rubiaceae), a Cameroonian medicinal plant traditionally used to cure microbial infections. The ethanol extract was prepared by maceration and extracted with ethyl acetate and n-butanol. The EtOAc (m = 168 g) and n-BuOH (m = 20 g) extracts were further fractionated by silica gel column chromatography to isolation of compounds. Their structures were elucidated by spectroscopic analysis and by comparison with published data. The antibacterial activity of extracts and compounds was assessed by evaluating the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against pathogenic bacteria. Thirteen compounds including four alkaloids (veprisine (1), naucleofficine III (2), vepridimerine B (3), and vepridimerine C (4)), three triterpenes (barbinervic acid (5), 3-O-α-L-rhamnopyranosyl quinovic acid (6), and oleanolic acid (7)), one steroid (ß-sitosterol-3-O-ß-D-glucopyranoside (8)), four phenolic compounds (scopoletin (9), gallic acid (10), quercetin-3-O-ß-D-glucopyranoside (11), and kaempferol 3-O-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside (12)), and one iridoid (borreriagenin (13)) were isolated from the EtOAc and n-BuOH extracts. These compounds were identified by 1D and 2D NMR combined analysis as well as by melting point comparison. The EtOH, EtOAc, and n-BuOH extracts exhibited significant antibacterial activities (MIC = 32-128 µg/mL; MBC = 64-256 µg/mL) against Staphylococcus aureus (Gram-positive bacterium), Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumonia (Gram-negative bacteria). Among the isolated compounds, scopoletin (9) showed a moderate activity against Klebsiella pneumoniae with MIC and MBC values of 16 µg/mL and 32 µg/mL, respectively. It appears that, chemotaxonomically, some of the isolated compounds have already been obtained from the genus Psychotria but to the best of our knowledge, this is the first report on the phytochemical investigation of P. succulenta. Although many other studies need to be achieved, our results support the use of P. succulenta in traditional medicine to cure infectious diseases particularly those caused by the tested bacteria.

Constituents from ripe figs of Ficus vallis-choudae Delile (Moraceae) with antiplasmodial activity.

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 IC50 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 (IC50 = 24.6 ± 1.5 µM) and Dd2 (IC50 = 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 IC50 values of 13.86 and 8.18 µg/mL, respectively. • Wighteone was the most active compound against PfDd2 (IC50 = 11.9 ± 2.4 µM).

Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq.

The polar fraction of the MeOH extract of the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was investigated for its constituents and two previously unreported monodesmosides triterpene saponins, telephiifoliosides A and B (1 and 2), along with the known bonushenricoside A (3) were isolated. Their structures were elucidated by combined spectroscopic and spectrometric techniques (1H NMR, 13C NMR, HSQC, 1H-1H COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods. The structures of the new saponins were established as; 3-O-α-L-arabinopyranosyljaligonic acid (1), and 3-O-α-L-arabinopyranosylphytolaccagenin ester (2). Upon evaluation of the antiproliferative activity on human malignant epithelial (HeLa) cells, none of the isolated compounds was efficient at the concentration of 33 µM. [Formula: see text]HighlightsThis is the first phytochemical study on Corrigiola litoralis subsp. telephiifolia.Two new saponins were isolated from the roots of Corrigiola litoralis subsp. telephiifolia.The isolated compounds were tested for their antiproliferative activity.

Cameroonian medicinal plants as potential candidates of SARS-CoV-2 inhibitors.

Coronavirus disease 2019 (COVID-19) is an ongoing pandemic instigated by Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) which changed the daily train of the world's population and cause several dead. Despite the significant efforts made in developing vaccines and therapeutic drugs, there is currently no available effective treatment against this new coronavirus infection, hence the need to continue research which is aimed at limiting the progression of this virus. The present study which has as objective to carry out in silico studies on the metabolites of some Cameroonian medicinal plants of the Asteraceae family with a view to propose potential molecules to fight against COVID-19. The selected plants are commonly used to treat respiratory infectious diseases, and for this reason they may contain some constituents which could exhibit an antiviral activity against SARS-CoV-2. In this work, a set of 74 naturally occurring compounds are computed with SARS-CoV-2 main protease protein (PDB ID: 6lu7) and spike protein (PDB ID: 6m0j) for their affinity and stability using binding energy analysis and molecular docking. Chrysoeriol-7-O-ß-D-glucuronopyranoside (compound 16) has showed promising results including excellent Absorption, Distribution, Metabolism and Excretion (ADME) parameters as well as insignificant toxicity. Finally, the stability of this compound is complex with the two proteins validated through molecular dynamics (MD) simulation, they displayed stable trajectory and molecular properties with consistent interaction profile in molecular dynamics simulations. These findings call for further in vitro and in vivo challenges of phytoconstituents against the COVID-19 as a potential agent to fight the spread of this dramatic pandemic.Communicated by Ramaswamy H. Sarma.

Botanicals and phytochemicals from the bark of Hypericum roeperianum (Hypericaceae) had strong antibacterial activity and showed synergistic effects with antibiotics against multidrug-resistant bacteria expressing active efflux pumps.

ETHNOPHARMACOLOGICAL RELEVANCE: Infections due to multidrug-resistant (MDR) bacteria constitute a real problem in the public health worldwide. Hypericum roeperianum Schimp. ex A. Rich (Hypericaceae) is used traditionally for treatment of various ailments such as abdominal pains, constipation, diarrhea, indigestion, nausea, and bacterial diseases. AIM OF THE STUDY: This study was aimed at investigating the antibacterial and antibiotic-modifying activity of the crude methanol extracts (HRB), ethyl-acetate soluble fraction (HRBa), residual material (HRBb), and 11 compounds from the bark of Hypericum roeperianum against multi-drug resistant (MDR) bacteria expressing active efflux pumps. MATERIALS AND METHODS: The antibacterial activity, the efflux pump effect using the efflux pump inhibitor (EPI), phenylalanine-arginine-ß-naphthylamide (PAßN), as well as the antibiotic-modifying activity of samples were determined using the broth micro-dilution method. Spectrophotometric methods were used to evaluate the effects of HRB and 8,8-bis(dihydroconiferyl) diferulate (11) on bacterial growth, and bacterial membrane damage, whereas follow-up of the acidification of the bacterial culture was used to study their effects on bacteria proton-ATPase pumps. RESULTS: The crude extract (HRB), HRBa, and HRBb had selective antibacterial activity with MICs ranging from 16 to 512 µg/mL. Phytochemical 11 displayed the best antibacterial activity (0.5 ≤ MIC ≤ 2 µg/mL). The activity of HRB and 11 in the presence of EPI significantly increased on the tested bacteria strains (up to 32-fold). The activity of cloxacillin (CLO), doxycycline (DOX), and tetracycline (TET), was considerably improved (up to 64-fold) towards the multidrug-resistant Enterobacter aerogenes EA-CM64 strain. The crude extract (HRB) and 11 induced the leakage of bacterial intracellular components and inhibited the proton-ATPase pumps. CONCLUSIONS: The crude extract (HRB) and 8,8-bis(dihydroconiferyl)diferulate from the bark of Hypericum roeperianum are good antibacterial candidates that deserve further investigations to achieve antibacterial drugs to fight infections involving MDR bacteria.

Hepatoprotective effects of extracts, fractions and compounds from the stem bark of Pentaclethra macrophylla Benth: Evidence from in vitro and in vivo studies.

AIM: To identify the bioactive hepatoprotective components of the ethanol extract of Pentaclethra macrophylla stem bark using in vitro and in vivo approaches. METHODS: The bioguided-fractionation of the ethanol extract was based on the substances' capacity to prevent in vitro, the lipid peroxidation of hepatocytes' membranes induced by hydrogen peroxide. For the in vivo hepatoprotective test, mice were treated orally with the ethyl acetate (EtOAc) fraction of the ethanol extract at doses of 50 and 75 mg/kg/day for one week and subjected to d-galactosamine/lipopolysaccharide (GaIN/LPS)-induced hepatotoxicity. Blood samples were collected for alanine aminotransferase (ALAT), aspartate aminotransferase (ASAT), TNF-α and IL-1ß assays. The liver was harvested for histological and biochemical (proteins, glutathione (GSH), catalase and superoxide dismutase (SOD)) analysis. RESULTS: The ethanol extract and fractions induced concentration-dependent inhibition of lipid peroxidation (IC50: 3.21-48.90 µg/mL) greater than that of silymarin (IC50: 117.4 µg/mL). The purification of the sub-fractions of EtOAc fraction yielded: (7R)-7-hydroxyhexacosanoic acid (1), (7R)-1-(7-hydroxyhexacosanoyl) glycerol (2), bergenin (3), 11-O-galloylbergenin (4), 2-hydroxymethyl-5-(2-hydroxypropan-2-yl)phenol (5), ß-sitosterol 3-O-ß-d-glucopyranosyl (6) and ß-sitosterol (7)), among which 11-O-galloylbergenin (IC50:1.8 µg/mL) was the most effective. The EtOAc fraction significantly reduced the serum level of ALAT, ASAT and TNF-α in vivo. This EtOAc fraction increased the liver protein content and protected the liver against structural damages, but did not boost the endogenous antioxidant parameters. CONCLUSION: The stem bark of Pentaclethra macrophylla possesses hepatoprotective effects that may result from its capacity to inhibit lipid peroxidation and could be attributed to its active components 3, 4 and 2.

Acaricidal activity, mode of action, and persistent efficacy of selected essential oils on the poultry red mite (Dermanyssus gallinae).

In this work, the essential oils (EOs) from Litchi chinensis, Clausena anisata, Heracleum sphondylium, Pimpinella anisum, Lippia alba, Crithmum maritimum and Syzygium aromaticum were tested for their contact toxicity against the poultry red mite, Dermanyssus gallinae, a deleterious ectoparasite of aviary systems. In addition, in order to give insights on their mode of action and effectiveness, the vapor phase and residual toxicity tests were also performed. Results showed that amongst all the tested EOs, that of S. aromaticum demonstrated the highest contact toxicity, with a LC50 value of 8.9 µg/mL, followed by C. maritimum and L. chinensis EOs, with LC50 values of 23.7 and 24.7 µg/mL, respectively. L. chinensis and C. anisata EOs showed higher vapor toxicity than the other EOs. L. chinensis and S. aromaticum EOs showed promising toxic effects up to 4 days post-application. Taken together, these results highlighted L. chinensis and S. aromaticum as two promising sources of biopesticides, able to cause severe contact, vapor and residual toxicity in the poultry red mites. Given the wide plant cultivation and uses in foodstuffs, cosmetics, flavour and fragrances, these EOs may be considered cheap and ready-to-use products as valid, eco-friendly alternatives to pesticides currently used in the aviary systems.

Acute and sub-acute toxicity of the aqueous extract from the stem bark of Tetrapleura tetrapteura Taub. (Fabaceae) in mice and rats.

ETHNOPHARMACOLOGICAL RELEVANCE: Tetrapleura tetrapteura Taub. is a leguminous multipurpose tree (Fabaceae) indigenous to tropical Africa. Fruits, seeds and stem bark infusions or decoctions of Tetrapleura tetrapteura Taub. are used to treat many diseases, such as gastric ulcer, rheumatism, malaria, hypertension and hyperlipidemia. AIM OF THE STUDY: This work was conducted to evaluate the acute and sub-acute toxicity of the aqueous extract of Tetrapleura tetrapteura Taub. (AETT) stem barks. MATERIALS AND METHODS: For the study of acute toxicity, single oral doses of 2000 mg/kg and 5000 mg/kg of AETT were administrated to male and female Balb/c mice, followed by observation of mice for 14 days. In the study of sub-acute toxicity, 48 albino wistar rats of both genders were randomly divided into six groups of 8 animals and they were daily and orally administrated for twenty eight days. The animal's test groups and satellite test group were administrated with the extract (AETT) at the doses of 100, 200 and 400 mg/kg and 400 mg/kg respectively. On the 29th day, the satellite group (control 2 and satellite 400 mg/kg) were observed during two more weeks. General behavior changes, mortality, body weight of animal, water and food intake were recorded during the study period. At the end of each treatment period, biochemical and hematological parameters were measured and histological examinations of liver and kidneys sections performed. RESULTS: Up to 5000 mg/kg single dose administration of AETT for fourteen days registered no death animal. In sub-acute study, no mortality was recorded in various experimental groups. Significant reductions in body weight, water and food intake were recorded in all treated animals. Relative weights of liver, kidneys, stomach, spleen, lungs, and heart of treated animals remained unchanged. Significant increases in the number of platelets as well as in serum ALAT level were recorded in rats, treated with 400 mg/kg of AETT. Female rat liver histology showed, at a higher dose of AETT, a slight congestion of portal vein. CONCLUSION: AETT is safe after therapeutic (200 mg/kg) or acute administration. Higher dose (400 mg/kg) administered for longer period showed signs of liver toxicity.

Clausena anisata and Dysphania ambrosioides essential oils: from ethno-medicine to modern uses as effective insecticides.

Dysphania ambrosioides (L.) Mosyakin & Clemants (Amaranthaceae) and Clausena anisata (Willd.) Hook. f. ex Benth. (Rutaceae) are two aromatic species traditionally used in Cameroon to repel and kill insects. The present work was carried out to substantiate this traditional use and to evaluate the possible incorporation in commercial botanical insecticides of their essential oils (EOs). The EOs were distilled from leaves of C. anisata and aerial parts of D. ambrosioides and analyzed by gas chromatography-mass spectrometry (GC-MS). The insecticidal activity of both EOs was investigated against the filariasis vector, Culex quinquefasciatus, and the housefly, Musca domestica. As possible mode of action, the inhibition of acetylcholinesterase (AChE) by the two EOs was investigated as well. The D. ambrosioides EO was characterized by the monoterpene peroxide ascaridole (61.4%) and the aromatic p-cymene (29.0%), whereas the C. anisata EO was dominated by the phenylpropanoids (E)-anethole (64.6%) and (E)-methyl isoeugenol (16.1%). The C. anisata EO proved to be very toxic to third instar larvae of C. quinquefasciatus showing LC50 of 29.3 µl/l, whereas D. ambrosioides EO was more toxic to adults of M. domestica showing a LD50 of 51.7 µg/adult. The mixture of both EOs showed a significant synergistic effect against mosquito larvae with LC50 estimated as 19.3 µl/l, whereas this phenomenon was not observed upon application to M. domestica adults (LD50 = 75.9 µg/adult). Of the two EOs, the D. ambrosioides one provided a good inhibition of AChE (IC50 = 77 µg/ml), whereas C. anisata oil was not effective. These findings provide new evidences supporting the ethno-botanical use of these two Cameroonian plants, and their possible application even in synergistic binary blends, to develop new eco-friendly, safe and effective herbal insecticides.

Traditional herbal remedies and dietary spices from Cameroon as novel sources of larvicides against filariasis mosquitoes?

In Cameroon, many dietary spices are used by traditional healers to cure several diseases such as cancer and microbial infections. Aframomum daniellii, Dichrostachys cinerea and Echinops giganteus are Cameroonian spices widely used as flavourings and as food additives. Moreover, they are traditionally herbal remedies employed to treat several diseases, as well as to control populations of insect pests. In this research, we analysed the chemical composition of A. daniellii, D. cinerea and E. giganteus essential oils and we evaluated their larvicidal potential against larvae of the filariasis and West Nile virus vector Culex quinquefasciatus. The essential oils were obtained from different plant parts by hydrodistillation and their composition was analysed by GC-MS. The three spices exhibited different volatile chemical profiles, being characterized by 1,8-cineole, sabinene and ß-pinene (A. daniellii), geraniol and terpinen-4-ol (D. cinerea), and silphiperfol-6-ene and presilphiperfolan-8-ol (E. giganteus). Results showed that the highest larvicidal toxicity on Cx. quinquefasciatus was exerted by D. cinerea essential oil (LC50 = 39.1 µL L-1), followed by A. daniellii (pericarp essential oil: LC50 = 65.5 µL L-1; leaves: LC50 = 65.5µL L-1; seeds: LC50 = 106.5µL L-1) and E. giganteus (LC50 = 227.4 µL L-1). Overall, the chance to use the D. cinerea essential oil against Cx. quinquefasciatus young instars seems promising, since it is effective at moderate doses and could be an advantageous alternative to build newer mosquito control tools.

Antimicrobial and antioxidant flavonoids from the leaves of Oncoba spinosa Forssk. (Salicaceae).

BACKGROUND: Naturally occurring flavonoids have been reported to possess various pharmacological properties. The aim of this study was to evaluate the antimicrobial and antioxidant activities of the MeOH extract and flavonoids from the leaves of Oncoba spinosa, a plant used for the treatment of syphilis, wounds and sexual impotence. METHODS: The plant extract was prepared by maceration in methanol and sequentially fractionated by column chromatography. The structures of isolated compounds were elucidated on the basis of spectral studies and comparison with published data. The MeOH extract and its isolated compounds were evaluated for their antibacterial and antifungal activities by broth microdilution method. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) and trolox equivalent antioxidant capacity (TEAC) assays were used to detect the antioxidant activity. The samples were tested spectrophotometrically for their hemolytic properties against human red blood cells. RESULTS: The fractionation of the MeOH extract afforded five known flavonoids including kaempferol (1), quercetin (2), apigenin-7-O-ß-D-glucuronopyranoside (3), quercetin 3-O-ß-D-galactopyranoside (4) and quercetin 3-O-α-L-rhamnopyranosyl (1 → 6) ß-D-glucopyranoside (5). The MeOH extract displayed weak to moderate antimicrobial activities (MIC = 256-2048 µg/ml). Quercetin 3-O-α-L-rhamnopyranosyl (1 → 6) ß-D-glucopyranoside (5) and quercetin (2) were respectively the most active compounds against bacteria (MIC = 8-64 µg/ml) and fungi (MIC = 64 - 128 µg/ml). These tested samples also showed high radical-scavenging activities (EC50 = 5.08 - 70.56 µg/ml) and gallic acid equivalent antioxidant capacities (TEAC = 53.76 - 89.86 µg/ml) when compared with vitamin C (EC50 = 4.72 µg/ml). The MeOH extract and compounds 2-5 were non-toxic to human red blood cells indicating their high selectivity to be used as antimicrobial and antioxidant drugs. CONCLUSION: The MeOH extract of O. spinosa as well as compounds 2 - 5 could be a potential source of natural antimicrobial and antioxidant products.

Steroidal saponins from the flowers of Dioscorea bulbifera var. sativa.

Eleven steroidal saponins, dioscoreanosides A-K, along with five known congeners, were isolated from the flowers of Dioscorea bulbifera var. sativa. Their structures were established by extensive NMR experiments in conjunction with mass spectrometry. The isolated compounds were tested for cytotoxicity against urinary bladder carcinoma cells (ECV-304 cells). Our results revealed a moderate activity for spiroconazol A (15), pennogenin 3-O-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-ß-d-glucopyranoside (12), and 26-O-ß-d-glucopyranosyl-(25R)-5-en-furost-3ß,17α,22α,26-tetraol-3-O-α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-ß-d-glucopyranoside (13).

Antibacterial activities of the extracts, fractions and compounds from Dioscorea bulbifera.

BACKGROUND: Dioscorea bulbifera is an African medicinal plant used to treat microbial infections. In the present study, the methanol extract, fractions (DBB1 and DBB2) and six compounds isolated from the bulbils of D. bulbifera, namely bafoudiosbulbins A (1), B (2), C (3), F (4), G (5) and 2,7-dihydroxy-4-methoxyphenanthrene (6), were tested for their antimicrobial activities against Mycobacteria and Gram-negative bacteria involving multidrug resistant (MDR) phenotypes expressing active efflux pumps. METHODS: The microplate alamar blue assay (MABA) and the broth microdilution methods were used to determine the minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of the above samples. RESULTS: The results of the MIC determinations indicated that when tested alone, the crude extract, fractions DBB1 and DBB2 as well as compounds 2 to 5 were able to prevent the growth of all the fifteen studied microorganisms, within the concentration range of 8 to 256 µg/mL. The lowest MIC value for the methanol extract and fractions (16 µg/mL) was obtained with DBB1 and DBB2 on E, coli AG100A and DBB2 on Mycobacterium tuberculosis MTCS2. The lowest value for individual compounds (8 µg/mL) was recorded with compound 3 on M. smegmatis and M. tuberculosis ATCC and MTCS2 strains respectively. The activity of the samples on many MDR bacteria such as Enterobacter aerogenes EA289, CM64, Klebsiella pneumoniae KP63 and Pseudomonas aeruginosa PA124 was better than that of chloramphenicol. When tested in the presence of the efflux pump inhibitor against MDR Gram-negative bacteria, the activity of most of the samples increased. MBC values not greater than 512 µg/mL were recorded on all studied microorganisms with fraction DBB2 and compounds 2 to 5. CONCLUSIONS: The overall results of the present investigation provided evidence that the crude extract D. bulbifera as well as some of the compounds and mostly compounds 3 could be considered as potential antimicrobial drugs to fight against MDR bacteria.

Bioefficacy of essential and vegetable oils of Zanthoxylum xanthoxyloides seeds against Acanthoscelides obtectus (Say) (Coleoptera: Bruchidae).

Experiments were conducted in the laboratory to evaluate the bioefficacy of essential and vegetable oils of Zanthoxylum xanthoxyloides (Rutaceae) against Acanthoscelides obtectus (Coleoptera: Bruchidae). The chemical composition of the essential oil and the fatty acid composition of the vegetable oil extracted from the seeds of Z. xanthoxyloides were determined. The insecticidal activities of these oils and the associated aromatized clay powder were evaluated against A. obtectus. Both oils were strongly repellent (100% repellency at 0.501 µl/cm² essential oil and 3.144 µl/cm² vegetable oil) and highly toxic (LC50 = 0.118 µl/cm² for essential oil) to this beetle after contact on filter paper. The vapors of the essential oil were highly toxic to adult insects (LC50 = 0.044 µl/cm³), and the aromatized powder made from clay and essential oil was more toxic (LD50 = 0.137 µl/g) than the essential oil alone (LD50 = 0.193 µl/g) after 2 days of exposure on a common bean. Both oils greatly reduced the F1 insect production and bean weight loss and did not adversely affect the bean seed viability. In general, the results obtained indicate that these plant oils can be used for control of A. obtectus in stored beans.

A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.

The aerial part of Rubus rigidus var. camerunensis (Rosaceae) is used to treat respiratory and cardiovascular disorders in the Cameroonian traditional medicine. The ethanol extract exhibited more potent antioxidant activity (E(max)s of 119% and 229% activity on DPPH and ß-carotene test) than aqueous extract. Bioactivity-guided fractionation of the ethanol extract based on free radical-scavenging assay (DPPH assay) afforded five flavonoid glycosides (four flavonol glycosides and an anthocyanin) and three glucosides of 19α-hydroxyursane-type triterpenoid (two monomeric and one dimeric triterpenoids). The flavonoids were identified as kaempferol 3-O-(2″-O-E-p-coumaroyl)-ß-D-glucopyranoside (1), kaempferol-3-O-ß-D-glucopyranoside (astragalin, 2), kaempferol-3-O-α-L-arabinofuranoside (juglanin, 3), quercetin-3-O-ß-D-glucopyranoside (isoquercitrin, 4), pelargonidin-3-O-ß-D-glucopyranoside (callistephin, 5). The three triterpenoids were 2α, 3ß, 19α, 23-tetrahydroxyurs-12-ene-28-O-ß-D-glucopyranosyl ester (nigaichigoside F(1), 6), 2α, 3ß, 19α-trihydroxyurs-12-ene-23-carboxyl-28-O-ß-D-glucopyranosyl ester (suavissimoside R(1), 7) as monomeric triterpenoids and coreanoside F(1) (8) as a dimeric triterpenoid. The flavonoids exhibited potent antioxidant activities (66 to 93.56% against DPPH radical) and they were also active on ß-carotene test. Coreanoside F(1) exhibited a 63% antioxidant activity, meanwhile the other two triterpenoids showed a weak activity. Three important facts on structure-activity relationship were observed: Compound 8, a dimeric triterpenoid glycoside, strongly enhanced antioxidant activity of its monomers, compound 3 with 3-O-α-L-arabinofuranyl has much more potent activity than compound 2 with 3-O-ß-D-glucopyranosyl, and antocyanin (5) is more potent than its corresponding flavonol glycosides.