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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 (β-sitosterol-3-O-β-D-glucopyranoside (8)), four phenolic compounds (scopoletin (9), gallic acid (10), quercetin-3-O-β-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 μ g / mL ; MBC = 64 ‐ 256 μ g / 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.

The genusCassiais a significant source of secondary metabolites that are physiologically active and come from several chemical classes. The current research deals with the isolation, spectroscopic elucidation (1D and 2D NMR spectroscopy) and enzymatic activity of fifteen known compounds as well as a new unidentified avenasterol derivative namely 21-methylene-24-ethylidene lophenol. The urease andβ-glucosidase inhibitory effects of these compounds were studied for the first time, and molecular docking studies were also performed to verify the structure-activity relationships. All the compounds evaluated towards urease showed higher inhibitory activity (1.224±0.43 < IC50> 6.678±0.11μM) compared to standard thiourea (IC50= 18.61±0.11μM). Molecular docking results revealed that compound7strongly inhibits urease due to the formation of a stable ligand-urease complex via hydrogen bonding, van der Waal and hydrophobic interactions. Formation of a favourable complex of7with the target enzyme gave a more negative docking score (−6.95 kcal/mol) than that of thiourea (−3.13 kcal/mol). Regarding theβ-glucosidase enzyme, all the compounds evaluated did not show activity except compound1which inhibited the latter with a percentage of inhibition of 82.6. These findings imply that this plant may be a contender for developing novel treatments for infectious disorders brought on by urease-producing bacteria.

Eleven previously undescribed arylnaphthalide lignans (

A recent find of a Marasmius species in Northern Thailand led to the isolation of five unprecedented derivatives of the carotane antibiotic fulvoferruginin (1), fulvoferruginins B–F (2–6). The structures of these sesquiterpenoids were elucidated using HRESIMS, 1D and 2D NMR, as well as CD spectroscopy. Assessing the bioactivity, fulvoferruginin emerged as a potent cytotoxic agent of potential pharmaceutical interest.

A previously unreported gallocatechin glycoside, (2

Phytochemical investigation of the methanol extracts from the leaves and bark of

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...

Phytochemical investigation of the seeds of Pentaclethra macrophylla led to the isolation of a mixture of two new aromatic monoterpene glycosides, pentamacrophylloside A (1a) and pentamacrophylloside B (1b), together with six known secondary metabolites: Comososide (2), secopentaclethroside (3), caffeoylputrescine (4), β-sitosterol-3-O-β-D-glucopyranoside (5), 2-hydroxymethyl-5-(2-hydroxypropan-2-yl)phenol (6), and sucrose (7). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR), high-resolution mass spectrometry and by comparison of their spectral data with those of related compounds. The extracts and compounds 3 and 4 were screened for their antimicrobial activity. The n-BuOH fraction showed a weak effect against three microbial strains: Candida albicans (MIC: 256 μg/mL), Enterococcus faecalis (MIC: 512 μg/mL), and Proteus mirabilis (MIC: 512 μg/mL) while no significant inhibition was observed for pure compounds when compared to ketoconazole and ciprofloxacin used as references. Furthermore, the ethnobotany and pharmacology of this plant are reviewed, and the chemophenetic significance of the isolation of the above secondary metabolites is discussed. This is the first report on the isolation of aromatic monoterpenoids from a plant of the genus Pentaclethra.

Medicinal plants are known as sources of potential antibacterial compounds including alkaloids. The aim of the present study was to evaluate the antibacterial activities of the extract, fractions, and some secondary metabolites isolated from the leaves of Crinum glaucum A. Chev. (Amaryllidaceae). The antibacterial activities were performed with the ethanol (EtOH) extract, as well as with ethyl acetate (EtOAc) and n-butanol (n-BuOH) fractions. Repeated column chromatography of the fractions led to the isolation of several compounds and their structures were elucidated mainly by means of extensive spectroscopic analysis [(one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), mass spectrometry)] and the comparison with published data. This includes eleven alkaloids: (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1), lycorine (2), ungeremine (3), ambelline (4), macronine (5), 5,6-dihydrobicolorine (6), trisphaeridine (7), hippadine (8), adenosine (9), arolycoricidine (10), pratorimine (11); two steroids: β-sitosterol (12), β-sitosterol-3-O-β-D-glucopyranoside (14) and one triterpene: oleanolic acid (13). Apart from lycorine (2), all these secondary metabolites are isolated from C. glaucum for the first time. The in vitro antibacterial activity of the EtOH extract, and the n-BuOH and EtOAc fractions as well as compounds 2, 3, 6 and 9 against pathogenic bacteria was performed. All extracts and fractions showed varying levels of antibacterial properties against at least one of the bacteria strains tested. The n-BuOH fraction was the most active extract with the lowest minimal inhibitory concentration (MIC) value of 64 µg/mL against Enterococcus faecalis. For pure compounds, the best MIC (8 µg/mL) was obtained with ungeremine (3) against Enterococcus faecalis and Pseudomonas aeruginosa. Our results show the antimicrobial potential of C. glaucum and scientifically validate its uses in traditional medicine against infectious diseases including cough and sexually transmitted infections. Ungeremine seems to be the antimicrobial active ingredient of this medicinal plant.

Phytochemical studies on Momordica foetida led to the isolation and characterization of Momordin (23,24,25,26,27-pentanorcucurbitacin) (3), a new pentanor cucurbitane along with the known β-sitosterol 3-O-β-D-glucopyranoside (4), β-sitosterol (5) and kaempferol-7-O-s-D-glucopyranoside (6). In adition to those components, two previously unreported cucurbitane glucosides, namely 3β-hydroxy-7-oxo-23(R)-cucurbita-5,24-diene-23-O-β-D-glucopyranoside (Momordiside A) (1) and 3β-hydroxy-7β-methoxy-23(R)-cucurbita-5,24-diene-23-O-β-D-glucopyranoside (Momordiside B) (2) were also obtained. The structures were elucidated by HR-ESI-MS and spectroscopic analysis including 1D- and 2D-NMR. Compounds 1 and 2 showed significant antioxidant potential in DPPH radical scavenging assay. In addition, compound 2 further revealed significant inhibitory potential against the enzyme urease in vitro as well as moderate activity against oral cancer cell line CAL-27.

Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside: apigenin-8-C-[6''-(E)-feruloyl]-β-D-glucopyranoside] (1), together with sixteen known compounds including quercetin-3-O-α-L-rhamnoside (2), vitexin (3), isovitexin (4), quercetin-3-O-β-D-glucopyranoside (5), quercetin-3-O-β-D-arabinopyranoside (6), quercetin (7), kaempferol (8), methyl inositol (9), sucrose (10), betulinic acid (11), vanillic acid (12), stigmastane-3β,6α-diol (13), aurantiamide acetate (14), robinetinidol (15), catechin (16) and epicatechin (17). The structures of these compounds were established on the basis of their spectroscopic (1 D and 2 D NMR) and mass spectrometric (ESI-TOF-MS) data. The methanol extracts, fractions and some of the isolated compounds were screened for their antimicrobial properties against five microbial strains. The methanol extract and the ethyl acetate fraction from the bark showed very weak antifungal activity against C. glabrata with the same MIC value of 128 μg/mL. Compound 7 was weakly active against C. albicans with MIC of 32 μg/mL.

Drug resistance due to the extensive abuse and over-use of antibiotics has become an increasingly serious problem and researchers started to use plants as an alternative source of new antibiotics. The aim of the present study was to assess the antimicrobial properties of secondary metabolites isolated from A. liebrechtsiana. A new secoiridoid derivative, anthocleistenolide B (1), along with three known compounds, the monoterpene diol, djalonenol (2), the xanthone O-glycoside, decussatin 1-O-β-D-glucopyranoside and the fatty acid, dotriacontanoic acid (4) was isolated from the leaves and bark of this plant. Their structures were elucidated by extensive analysis of spectroscopic (1D and 2D NMR) and mass spectrometric data. The isolated compounds were screened for their antimicrobial properties against five strains of bacteria (two gram positive: Staphylococcus aureus 29213, Enterococcus faecalis ATCC 25922 and three gram negative: Escherichia coli ATCC51299, Proteus mirabilis (isolate), and Pseudomonas aeruginosa QC76110), but all were inactive.

A new steroid derivative, (24S)-3β-hydroxy-7β-methoxyergost-5-ene (1), was isolated along with eleven known compounds: 7α-hydroxysterol (2), β-sitosterol (3), oleanolic acid (4), betulinic acid (5), lupeol (6), swertiaperennin (7), decussatin (8), tetracosanoic acid (9) β-sitosterol-3-O-β- d -glucopyranoside (10), (2R,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-5-(2-formylvinyl)-7-hydroxybenzofuran (11) and acacetin 6-C-β- d -glucopyranoside (12) from the tree bark and leaves of Anthocleista liebrechtsiana De Wild & T. Durand. Their structures were elucidated on the basis of spectroscopic (1D and 2D NMR) and mass spectrometric data. Compounds 2 and 7–10 have already been isolated from the genus Anthocleista and 3–6 from the Loganiaceae family. The isolated secondary metabolites were screened for their antimicrobial properties but only compound 12 showed moderate activity against Pseudomonas aeruginosa. Furthermore, the chemotaxonomic significance among Anthocleista species is discussed.

The polar fraction of the MeOH extract of the roots of

Submerged mycelial cultures of the ascomycete Colpoma&nbsp, quercinum CCTU A372 were found to produce five previously undescribed tetramic acids, for which we propose the trivial names colposetins A–C (1–3) and colpomenoic acids A and B (4 and 5), along with the known compounds penicillide (6) and monodictyphenone (7). The planar structures of 1–5 were determined by high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and extensive 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Their absolute configurations were determined by the combination of electronic circular dischroism (ECD) analysis, J-based configurational analysis, and a rotating-frame Overhauser effect spectroscopy (ROESY) experiment. Colposetin B displayed weak antimicrobial activity against Bacillus subtilis and Mucor hiemalis (MIC 67 µg/mL).

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-1β 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), β-sitosterol 3-O-β- d -glucopyranosyl (6) and β-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.

A new triterpenoid saponin (Mimonoside D: 3-O-��-L-arabinopyranosyl-3��-hydroxyolean-12-en-28-oic acid 28-O-��-D-xylopyranosyl-(1���2)-��-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), ��-sitosterol (6), ��-sitosterol-3-O-��-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 ��g/mL), weakly inhibited Pseudomonas aeruginosa (MIC = 64 ��g/mL) and very weakly inhibited Staphylococcus aureus (MIC = 128 ��g/mL) and Enterococus faecalis (MIC = 128 ��g/mL).

Eight diketopiperazines including five previously unreported derivatives were isolated from an endophytic fungus cultured from the medicinal plant Globularia alypum collected in Algeria. The strain was characterised by means of morphological studies and molecular phylogenetic methods and was found to represent a species of a new genus in the Chaetomiaceae, for which we propose the name Batnamyces globulariicola. The taxonomic position of the new genus, which appears phylogenetically related to Stolonocarpus and Madurella, was evaluated by a multi-locus genealogy and by morphological studies in comparison to DNA sequence data reported in the recent monographs of the family. The culture remained sterile on several culture media despite repeated attempts to induce sporulation, and only some chlamydospores were formed. After fermentation in submerged culture and extraction of the cultures with organic solvents, the major secondary metabolites of B. globulariicola were isolated and their chemical structures were elucidated by extensive spectral analysis including nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionisation mass spectrometry (HRESIMS), and electronic circular dichroism (ECD) measurements. The isolated compounds were tested for their biological activities against various bacteria, fungi, and two mammalian cell lines, but only three of them exhibited weak cytotoxicity against KB3.1 cells, but no antimicrobial effects were observed.

The development and spread of resistance to currently available antibiotics is a major drawback in the treatment of microbial infections. Salmonellosis for example remains among the most common cause of morbidity and mortality in developing countries. This study aimed to evaluate the antisalmonellal potential of extracts, fractions, isolated compounds and semi-synthetic flavonoids from Tristemma hirtum P. Beauv. Bioguided fractionation by column chromatography of the EtOAc and n -BuOH fractions led to the isolation of eleven compounds including two new esterified glucuronide flavonoids namely: luteolin-3′-O-β-D-glucuronopyranosylbutyl ester (1), a mixture of compound 1 and quercetin-3-O-β-D-glucuronopyranosylbutyl ester (2). Chemical transformation mainly based on the prenylation of 6-hydroxyapigenin-7-O-β-D-glucopyranoside (5) afforded four new semi-synthetic flavonoid derivatives namely: 6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5a), 8-C-prenyl-6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5b), 8-C-prenyl-4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5c), 4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5d). The chemical structures of these compounds were assigned using NMR techniques, mass spectrometry and by comparison of their data with reported ones. The antisalmonellal activity was assessed by determining the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) using serial microdilution methods. The results showed that the MeOH extract and EtOAc fraction were active against all the bacteria tested with MICs ranging from 24 to 1536 µg/mL. Seven isolated compounds and three semi-synthetic compounds tested showed MIC values ranging from 16 to 256 µg/mL. Compounds 1, 3, 5a, 5c and 11 displayed the most potent antisalmonellal properties but were generally less potent than those of reference drugs. The activity of extracts and isolated compounds could be used as the starting point for the development of alternative phytodrugs against salmonellosis.

The new cyclic lipodepsipeptide ophiotine (1), two new arthrichitin derivatives named arthrichitins B (4) and C (5), a new xanthocillin-like alkaloid, xanthomide Z (2), and the previously described arthrichitin (3) were isolated from the liquid culture broth of a nematode-associated fungus with affinities to the genus Ophiosphaerella. The structural elucidation and determination of the absolute configuration of the new molecules were accomplished using a combination of spectroscopic and chemical techniques, including 1D and 2D NMR, HRMS, and Marfey's analysis. Opiotine (1) displayed moderate nematicidal activity against the host nematode ( Heterodera filipjevi), while xanthomide Z (2) exhibited very weak activity. Arthrichitin C (5) showed very weak cytotoxic effects on several cancer cell lines, with IC50 values in the range of 24-33 μM. Xanthomide Z is among few xanthocillin derivatives that comprise formamide functions instead of the cyano functions that are usually observed in this class of fungal alkaloids.

Two new metabolites possessing the unusual 1-oxa-7-azaspiro[4.4]non-2- ene-4,6-dione core (2, 3) along with the recently described pseurotin A3 (1) were isolated from the pathogenic fungus Wilsonomyces carpophilus (previously named Stigmina carpophila). The producer organism was obtained from Prunus armeniaca collected in Iran and was identified by morphological and molecular phylogenetic methods. The structures of the isolated compounds were elucidated on the basis of extensive NMR spectroscopic analysis, high-resolution mass spectrometry and ECD analysis. The compounds were screened for their antimicrobial, cytotoxic, nematicidal and biofilm inhibition activities but, no significant effect was observed. To the best of our knowledge, this is the first report on the isolation of secondary metabolites produced by W. carpophilus.

Lipid peroxidation plays a pivotal role in the pathogenicity and maintenance of hepatitis. Thus, substances protecting hepatocyte membranes from lipid peroxidation are of great importance in the management of hepatotoxicity and hepatitis. The present work deals with the in vitro hepatoprotective activity of the methanol extract of Desmodium uncinatum, its sub-fractions, the major isolated compounds and some of their semi-synthetic derivatives in order to study structure activity relationships. Using hydrogen peroxide (H2O2)-induced lipid peroxidation of hepatocyte membranes as a model, the hepatoprotective-guided phytochemical survey of the methanol extract of aerial parts of D. uncinatum was carried out by successive column chromatography. One of the most active compounds (Isovitexin) was chemically transformed to yield new semi-synthetic. The identification of isolated and semi-synthetic compounds was performed using NMR techniques, mass spectrometry and by comparison of their data with those reported in the literature. The n-butanol fraction was the most effective (IC50: 22.9 μg/mL) compared to the crude methanol extract (IC50: 43.6 μg/mL) and other fractions. The n-butanol sub-fractions FA (containing non-phenolic compounds) and FB (mainly containing phenolic compounds) exhibited respective IC50 of 14.36 and 128.2 μg/ml. Purification of FA yielded 3-O-β-D-glucopyranosyl-β-sitosterol (1), 3-O-β-D- 2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (2), (2S, 3S, 4R, 7R, 8Z)-1-O-β-D-glucopyranosyl-2-[(R)-2'-hydroxyarachidoylamino]-docosan-8-ene-3,4,7-triol (4), spiraeamide (5), mannitol (6), while FB afforded essentially three C-glycosylflavonoids namely isovitexin (7), vitexin (8) and vicenin-3 (9). Chemical transformations (methylation, allylation and prenylation) of isovitexin afforded five new semi-synthetic derivatives: 4',5,7-O- trimethyli-sovitexin (10), 4'-O-allylisovitexin (11), 4',7-O-diallylisovitexin (12), 4'-O-prenylisovitexin (13) and 8-C-prenyl-4',7-O-diprenylisovitexin (14). The screening of these derivatives revealed that allylation did not significantly affect the hepatoprotective activity while methylation, prenylation, number and position of sugar moieties on the A ring of flavonoids significantly reduced it. Results demonstrated that the n-butanol fraction obtained from the methanol extract of Desmdium uncinatum may possess hepatoprotective activity due to its content in C-glycosylflavonoids and cerebrosides. Hydroxyl groups in C-glycosylflavonoids are important for their lipid peroxidation inhibitory activity.

The MeOH extract of Dracaena viridiflora was found to display significant cytotoxicity against some cancer cell lines. Systematic phytochemical investigation of this extract led to the isolation and structure elucidation of ten secondary metabolites including five spirostane (1-5) and one furostane (6) steroidal saponins. Furthermore, some acetylated spirostane analogues and three previously unreported derivatives with the 22,26-epoxycholesta-5,22-diene skeleton (15-17) were prepared from trillin (1), prosapogenin A of dioscin (2) and dioscin (4) by reaction with ZnCl 2/Ac 2O. Among the isolated and semisynthetic compounds, dioscin showed the most potent cytotoxicity against A549, Jurkat and Skov-3 cells with IC 50 values of 0.42, 1.70 and 1.90 µg/mL, respectively. It was noteworthy that acetylation of the bioactive compounds led to semisynthetic derivatives which unfortunately did not present any activity. This is the first report on the phytochemical and pharmacological investigation of Dracaena viridiflora.

Phytochemical investigation of the aerial parts of Sansevieria trifasciata, one of the most common Dracaenaceae plants, has resulted in the isolation of a new dihydrochalcone derivative named trifasciatine C (1), four previously unreported steroidal saponins as two pairs of inseparable regioisomers: trifasciatosides K/L (2/3), M/N (4/5), together with the known 1,2-(dipalmitoyl)-3-O-β-D-galactopyranosylglycerol (6), aconitic acid (7), and 1-methyl aconitic acid (8). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D nuclear magnetic resonance) and high-resolution electronspray ionization-mass spectrometry, as well as chemical methods and comparison of their spectral data with those of related compounds. Compounds 2/3 and 4/5 were evaluated for their antiproliferative activity on Hela cells, and no significant effect was observed.

From extracts of the plant associated fungus Chaetosphaeronema achilleae collected in Iran, a previously unreported isoindolinone named chaetosisoindolinone (1) and a previously undescribed indanone named chaetosindanone (2) were isolated in addition to five known metabolites, 2-(2-acetyl-3,5-dihydroxyphenyl) acetic acid (3), vulculic acid (4), 2-(2-acetyl-3-hydroxy-5-methoxyphenyl)acetic acid (5), curvulin (6), and curvulol (7). Their structures were elucidated on the basis of extensive spectroscopic analysis and high-resolution mass spectrometry. The isolated compounds were tested for their antimicrobial, anti-biofilm, and nematicidal activities. Compound 2 exhibited cytotoxicity against the human breast adenocarcinoma MCF-7 cells with an IC50 value of 1.5 μg/mL. Furthermore, compounds 4 and 7 almost completely inhibited biofilm formation in Staphylococcus aureus at 256 μg/mL. Weak antimicrobial activities were also observed for some of the isolated compounds against Mucor hiemalis, Rhodoturula glutinis, Chromobacterium violaceum, and Staphylococcus aureus.

A new saponin, 3-O-β-d-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (1), was isolated from the methanol extract of stem bark of Crossopteryx febrifuga together with the known 3β-d-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (2), shanzhiside methyl ester (3), shanzhiside (4), β-sitosterol (5), β-sitosterol-3-O-β-d-glucopyranoside (6), ursa-12,20(30)-diene-27,28-dioic acid (7), hederagenin (8), and oleanolic acid (9). The structures were established by comprehensive interpretation of their spectral data 1D- (1H and 13C), 2D-NMR (1H-1H COSY, HMQC, HMBC), spectroscopic, and electrospray ionisation time-of-flight mass spectrometry analysis. The isolated compounds and extracts were screened for their antibacterial properties. Although the EtOAc and n-BuOH extracts exhibited considerable antibacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration (MIC) value of 32 μg/mL, compounds 2 and 8 showed moderate activity against Enterococcus faecalis with MIC values of 256 and 128 μg/mL, respectively. The new compound (1) exhibited a moderate antibacterial activity against Staphylococcus aureus with an MIC value of 512 μg/mL.

A new sulfated steroidal derivative (fruticogenin A: 1-sulfo-australigenin-3-sodium sulphate, 1) and three new steroidal saponins named fruticoside K (3-sulfo-spirostan-25(27)-ene-1β,3β-diol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-fucopyranoside], 2), fruticoside L (3-sulfo-spirostan-25(27)-ene-1β,3β,6α-triol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-fucopyranoside], 3) and fruticoside M (spirostan-25(27)-ene-1β,3α-diol-1-O-[α-L-rhamnopyranosyl-(1 → 2)-α-L-rhamnopyranoside], 4) were isolated from the aerial parts of Cordyline fruticosa L. var. strawberries. Their structures were established on the basis of 1D and 2D NMR data, mass spectrometry and chemical methods. Compounds 2 and 4 exhibited weak cytotoxicity against melanoma (A375), breast adenocarcinoma (MDA-MB-231), and colon carcinoma (HCT116) human tumor cell lines.

Chemical analysis of extracts from cultures of the plant pathogenic fungus Cytospora sp. strain CCTU A309 collected in Iran led to the isolation of two previously unreported heptanedioic acid derivatives namely (2R,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (1) and (2S,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (2) as diastereomers, four previously undescribed prenylated p-terphenyl quinones 3–6 in addition to five known metabolites. Their structures were elucidated on the basis of extensive spectroscopic analysis and high-resolution mass spectrometry. For metabolites 1 and 2, the absolute configurations at C-2 were deduced from comparison of the 1H NMR difference of their (S)- and (R)-phenylglycine methyl ester derivatives while the relative configurations were tentatively assigned by a J-based analysis and confirmed by comparison of 13C chemical shifts to literature data. The isolated compounds were tested for their cytotoxic, antimicrobial (including biofilm inhibition), antiviral, and nematicidal activities. While only moderate antimicrobial effects were observed, the terphenyl quinone derivatives 3–6 and leucomelone (10) exhibited significant cytotoxicity against the mouse fibroblast L929 and cervix carcinoma KB-3-1 cell lines with IC50 values ranging from 2.4 to 26 μg/mL. Furthermore, metabolites 4–6 showed interesting antiviral activity against hepatitis C virus (HCV).

Fifteen triterpenoid saponins including five new compounds (Mannioside B: 3β-[(β- d -glucopyranosyl)oxy]urs-12-en-28-oic acid α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl ester (1), mannioside C: 3β-[(β- d -glucopyranosyl)23-dioxy]urs-12-en-28-oic acid α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl ester (2), mannioside D: 3β,23-dihydroxyurs-12-en-28-oic acid β- d -glucopyranosyl-(1 → 6)- β- d -glucopyranosyl ester (3), mannioside E: 3β-hydroxy-23-oxolup-20(29)-en-28-oic acid α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl ester (4) and mannioside F: (22S)-27β-[(β- d -glucopyranosyl)oxy]-22-hydroxyprotosta-12,24-dien-3β-yl β- d -glucopyranoside (5)) were isolated from the leaves of Schefflera mannii (Hook.f.) Harms. Their structures were established on the basis of 1D and 2D NMR data, mass spectrometry and chemical methods. The major isolated compounds were tested for their antiproliferative activity on human malignant epithelial (HeLa) cells but were not efficient at the concentration of 33 mM.

Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including (1)H-NMR, (13)C-NMR, (1)H-(1)H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells.

The ethyl acetate extract from the whole plant of Crinum biflorum Rottb. Showed a moderate activity against Enterococcus faecalis. Its phytochemical investigation led to the isolation of a new flavan-3-ol derivative namely (2R,3R)-3-hydroxy-7-methoxy-3′,4′-methylenedioxyflavan, together with (2S)-7-hydroxy-3′,4′-methylenedioxyflavan, (2R,3R)-7-methoxy-flavan-3-ol, (2S)-7-hydroxy-3′,4′-dimethoxyflavan, 3′,7-dihydroxy-4′-methoxyflavan, 4′,7-dimethoxy-3′-hydroxyflavan, farrerol, β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside, oleanolic acid, kaempferol, pancratistatin, lupeol, aurantiamide acetate, Narciprimine and 2,3-dihydroxypropyl palmitate. Their structures were elucidated mainly by extensive spectroscopic analysis and comparison with published data. The absolute configuration of the new metabolite was determined by electronic circular dichroism (ECD) analysis and comparison of optical rotation. Some of the isolated compounds were tested for their antimicrobial activity but no inhibition was observed.

Two new sappanin-type homoisoflavonoids, (3 R )-7-hydroxy-8-methoxy-3′,4′-methylenedioxyhomoisoflavanone (trifasciatine A) 1 and (3 R )-3,7-dihydroxy-8-methoxy-3′,4′-methylenedioxyhomoisoflavanone (trifasciatine B) 2 were isolated as minor components from the EtOAc soluble fraction of the methanol extract of Sansevieria trifasciata collected in Cameroon together with the known 1-(stearoyl)-glycerol 3 and spirosta-5,25(27)-dien-1β,3β-diol-1- O -α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranoside 4 . Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR) and HRESIMS. Compounds 1 and 2 were screened for their antiproliferative activity on HeLa cells and no significant effect was observed when compare to 5-FU (fluorouracil) used as positive control.

From the EtOAc fraction of the methanol extract of the stem barks of Baillonella toxisperma (Sapotaceae), eight compounds were isolated using column chromatography techniques. Their structures were established on the basis of 1D and 2D-NMR data and comparison with data published in the literature. The MeOH extract, n-BuOH and EtOAc fractions together with some pure compounds (4, 5, 7, 8) were screened for their radical scavenging activity using the2,2-diphenyl-1- picryl-hydrazyl-hydrate (DPPH) free radical in order to get preliminary information about the antiradical capacities of this plant.Keywords: Baillonella toxisperma;Sapotaceae; DPPH; Antiradical activity

Phytochemical investigation of the roots of Furcraea bedinghausii Koch. Led to the isolation of a mixture of two new homoisoflavones, 5,7-dihydroxy-3-(3,4-methylenedioxybenzyl)-chromone (4a) and 5,7-dihydroxy-3-(4-methoxybenzyl)-chromone (4b), together with the known β-sitosterol (1), 7,4'-dihydroxyhomoisoflavane (2), dihydrobonducellin (3), kaempferol (5), 5,7-dihydroxy-3-(4-hydroxybenzyl)-chromone (6), 1-linoleylglycerol (7), 6’-linoleyl-3-O-β-D-glucopyranosyl-β-sitosterol (8), trans-3,3’,5,5’-tetrahydroxy-4’-methoxystilbene (9), yuccaol C (10), yuccaol D (11), 3-O-b-D-glucopyranosyl-b-sitosterol (12), 4-[6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-β-D-glucopyranosyloxy]-3-methoxybenzoic acid (13) and two pairs of steroidal saponins: (25R)-2α-3β–dihydroxy-5α-spirostan-12-one 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (14a) and (25R)-2α-3β–dihydroxy-5α-spirost-9-en-12-one 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (14b), (25R)-3β–hydroxy-5α-spirostan-12-one 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (15a) and (25R)-3β–hydroxy-5α-spirost-9-en-12-one 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (15b). Their structures were elucidated by interpretation of spectral data and by comparison with literature.

Two new tryptophan derivatives, N-sulfonyl-L-tryptophan (tryptorheedei A) (1) and 3-(N-sulfonylindolyl)-D-lactic acid (tryptorheedei B) (2) together with the known 5-O-β-D-glucopyranosyl-2-hydroxyphenylacetic acid (3), 1-O-methylglucopyranoside, entadamide A, homogentisic acid and 3-O-β-D-glucopyranosyl-β-sitosterol, were isolated from the seed kernels of Entada rheedei (Mimosaceae). Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry and by comparison with spectroscopic data reported in the literature. Compounds 1 and 2 showed no toxicity to TZM and Human PBMC cells. Both compounds 1 and 2 were found to promote early infection events in HIV, likely by inhibiting the enzyme indolamine 2,3-dioxygenase (IDO) and preventing tryptophan depletion. Inhibition of IDO acutely in HIV infection inhibits viral replication, but chronic activation of IDO leads to immune impairment in AIDS. IDO is also the gatekeeper enzyme for kynurenine metabolism, a pathway involved in serotonin and melatonin biosynthesis and the regulation of glutamate and dopamine levels in the brain. Therefore inhibition of IDO might explain both the reported medicinal and neuropsychiatric effects of E. rheedei.

A new C-glycosylflavone, drymaritin E (6-C-(3-keto-β-digitoxopyranosyl)-4'-O-(β-D-glucopyranosyl)-7-methoxyl-5,4'-dihydroxylflavone) 1 was isolated from the oily upper phase (SU) of the MeOH extract from aerial parts of Drymaria cordata together with two known compounds (cassiaoccidentalin A 2 and anemonin 3) and an inseparable mixture of two known C-glycosylflavones 5,4'-dihydroxy-7-methoxyflavone-6-C-(2''-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside 4a and 5,7,3',4'-tetrahydroxyflavone-6-C-(2''-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside 4b. The alkaline hydrolysis of 3 led to a new hemisynthetic derivative, sodium anemonate (sodium 2-((1'E) 2'-sodium-carboxylate-vinyl)-5-oxo-cyclohex-1-ene carboxylate) 3a. The chemical structures were determined by spectroscopic methods ((1)H NMR, (13)C NMR, (1)H-(1)H COSY, HMBC, HSQC, and NOESY) and mass spectrometry (ESI-MS). C-glycosylflavones had significant free radical-scavenging activities on the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, SU and compounds 3 and 3a exhibited no activity. In particular, compound 1 exhibited a concentration-dependent radical scavenging activity on DPPH with EC50 of 31.43 µg/mL.

From the bulbils of Dioscorea bulbifera L. var. sativa, three new clerodane diterpenoids, bafoudiosbulbin C (=methyl (2β,8α,12S)-17-oxo-2,19 : 8,19 : 12,17 : 15,16-tetraepoxycleroda-3,13(16), 14-triene-18-carboxylate; 1), bafoudiosbulbin D (=methyl (2β,6β,12R)-17,19-dioxo-2,19 : 6,17 : 8,12 : 15,16-tetraepoxycleroda-13(16),14-diene-18-carboxylate; 2), and bafoudiosbulbin E (=methyl (2β,3α,4α,6β,12R)-17,19-dioxo-2,19 : 3,4 : 6,17 : 8,12 : 15,16-pentaepoxycleroda-13(16),14-diene-18-carboxylate; 3) were isolated, together with the known compounds bafoudiosbulbins A and B, 3-O-β-D-glucopyranosyl-β-sitosterol, and 6′-stearoyl-3-O-β-D-glucopyranosyl-β-sitosterol. Their structures were established by high-field NMR techniques (1H,1H-COSY, 13C-DEPT, HSQC, HMBC, and NOESY), MS analyses, as well as by comparison of their spectral data with those of related compounds.