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.

New 21-nordammarane saponins with anti-inflammatory and cytotoxic activities from Lavigeria macrocarpa Oliv.

Chemical investigation of the ethanol extract from the stems and roots of the medicinal plant Lavigeria macrocarpa led to the isolation and structure elucidation of three previously unreported 21-nordammarane-type saponins namely 6α,27-dihydroxy-3,20-dioxo-21-nordammar-24-(Z)-ene 27-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside] (1), 6α,27-dihydroxy-3-oxo-21-nordammar-24-(Z)-ene 27-O-β-D-glucopyranoside (2), and 2α,3β,6α,27-tetrahydroxy-21-nordammar-24-(Z)-ene 27-O-β-D-glucopyranoside (3) trivially named lavigemacrocarposide A-C, along with eight known secondary metabolites. Acid hydrolysis of lavigemacrocarposide A yielded a new prosapogenin namely 6α,27-dihydroxy-3,20-dioxo-21-nordammar-24-(Z)-ene 27-O-β-D-glucopyranoside (1a) and the previously unreported artefactual aglycones 1b and 1c. Their structures were elucidated by spectroscopic analyses including mass spectrometry, 1D and 2D NMR as well as chemical evidence.

Desmoarylcoumarin and episoyasapogenol B: two new compounds from (Poir.) DC (Fabaceae).

A new 3-arylcoumarin, 7-hydroxy-6-(1,1-dimethylallyl)-2',5'-dihydroxy-4'-(3,3dimethylprenyl)-3-arylcoumarin (desmoarylcoumarin) , a previously unreported oleanane-type triterpenoid, 3,22,23-trihydroxyolean-12-en (episoyasapogenol B) , together with five known flavonoids including darbergioidin (), isoferreirin (), quercetin (), vitexin (), swertizin (), and one carbohydrate, sucrose () were isolated from the methanolic extract of the roots of . Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D) and mass spectrometric (HRFAB-MS) data. The methanolic extract, EtOAc and -BuOH fractions as well as some isolated compounds were assessed for their antibacterial and antioxidant activities.

A New Chalcone and Antimicrobial Chemical Constituents of .

Microbial infections are leading causes of death and morbidity all over the world due to the development of the resistance to antibiotics by certain microorganisms. In this study, the chemical exploration of the ethanol (EtOH) extract of the aerial part of (Dracaenaceae) led to the isolation of one previously unreported chalcone derivative, i.e.

Siamoside A: a new -glycosylated flavone from (Lam.) H. S. Irwin & Barneby (Caesalpiniaceae).

Phytochemical investigation of the methanol extracts from the leaves and bark of resulted in the isolation of one new flavone -glycoside: apigenin-8--[6''-feruloyl]---glucopyranoside] (), together with sixteen known compounds including quercetin-3----rhamnoside (), vitexin (), isovitexin (), quercetin-3----glucopyranoside (), quercetin-3----arabinopyranoside (), quercetin (), kaempferol (), methyl inositol (), sucrose (), betulinic acid (), vanillic acid (), stigmastane-3,6-diol (), aurantiamide acetate (), robinetinidol (), catechin () and epicatechin (). 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.

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.

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

A new triterpenoid saponin (Mimonoside D: 3---L-arabinopyranosyl-3-hydroxyolean-12-en-28-oic acid 28---D-xylopyranosyl-(1→2)--D- glucopyranoside ester ()) was isolated from the aerial parts of Sauvalle together with nine known compounds: 7,4'-dihydroxyflavone (), kaempferol (), lupeol (), betulinic acid (), -sitosterol (), -sitosterol-3---D-glucopyranoside (), lutein (), 5,2'-dihydroxy-7,4',5'-trimethoxyflavone () and vitexin (). Their structures were elucidated on the basis of spectroscopic (1D and 2D nuclear magnetic resonance) and high-resolution mass spectrometric data as well as by comparison of their spectral data with those of related compounds. Compounds , and had already been isolated from , while compounds , , and have been isolated from other species.

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

The polar fraction of the MeOH extract of the roots of subsp. (Pourr.) Briq.

Manniosides B-F, five new triterpenoid saponins from the leaves of Schefflera mannii (Hook.f.) Harms.

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.

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.

A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga.

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.

Steroidal saponins from the aerial parts of Cordyline fruticosa L. var. strawberries.

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.

Antioxidant C-glycosylflavones of Drymaria cordata (Linn.) Willd.

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).

Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae).

Three new triterpenoid saponins, elucidated as 3-O-β-D-glucopyranosyloleanolic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (parkioside A, 1), 3-O-[β-D-apifuranosyl-(1→3)-β-D-glucopyranosyl]oleanolic acid 28-O-[β-D-apifuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)β-D-xylopyranoside (parkioside B, 2) and 3-O-β-D-glucuronopyranosyl-16α-hydroxyprotobassic acid 28-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (parkioside C, 3), were isolated from the n-BuOH extract of the root bark of Butyrospermum parkii, along with the known 3-O-β-D-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities.

Novel 3-oxo- and 3,24-dinor-2,4-secooleanane-type triterpenes from Terminalia ivorensis A. Chev.

Two new oleanane-type triterpenes named ivorengenin A (=3-oxo-2α,19α,24-trihydroxyolean-12-en-28-oic acid; 1) and ivorengenin B (=4-oxo-19α-hydroxy-3,24-dinor-2,4-secoolean-12-ene-2,28-dioic acid; 2), together with five known compounds, arjungenin, arjunic acid, betulinic acid, sericic acid, and oleanolic acid, were isolated from the barks of Terminalia ivorensis A. Chev. (Combretaceae).

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 β-carotene test) than aqueous extract.

Dimeric antioxidant and cytotoxic triterpenoid saponins from Terminalia ivorensis A. Chev.

Three saponins, including two dimeric triterpenoid glucosides possessing an unusual skeleton, ivorenosides A and B, and a monomeric triterpenoid saponin (ivorenoside C), together with the known sericoside, were isolated from the bark of Terminalia ivorensis. Their structures were established on the basis of 1D and 2D NMR data, chemical methods and tandem MS-MS spectrometry as a dimer of β-D-glucopyranosyl-18,19-seco-2α,3β,19,19,24-pentahydroxyolean-12-en-28-oate and β-D-glucopyranosyl-2α,3β,19α,24-tetrahydroxyolean-12-en-28-oate (ivorenoside A, 1), a dimer of β-D-glucopyranosyl-18,19-seco-24-carboxyl-2α,3β,19,19-tetrahydroxyolean-12-en-28-oate and β-D-glucopyranosyl-2α,3β,19α,24-tetrahydroxyolean-12-en-28-oate (ivorenoside B, 2) and β-D-glucopyranosyl-2α,3β,19β,24-tetrahydroxyolean-11-oxo-olean-12-en-28-oate (ivorenoside C, 3). Ivorenosides A and B are the first examples in nature of dimeric triterpenoid saponins with a 18,19-seco E ring of one of the two units.