Bio-Guided Fractionation of (Forssk.) Webb & Berthel Polar Extracts.

The fractionation of the methanolic extract (MeOH-E) of (Forssk.) Webb & Berthel and further analysis by thin layer chromatography resulted in four fractions (F1, F2, F3 and F4) that, in parallel with the MeOH-E, were screened for antioxidant, cytotoxic, antidiabetic and antibacterial properties. In addition, chemical characterization of their bioactive molecules was performed using LC-DAD-ESI/MS.

Phenolic Extract from L. Rhizomes Inhibits Cellular Oxidative Stresses.

UV-B and IR-A radiation are important inducers of biological changes in skin involving ROS generation. The overloading of antioxidant defense mechanisms by ROS production could lead to photoaging and photocarcinogenesis processes. Various traditional usages are reported for L.

The genus Daphne: A review of its traditional uses, phytochemistry and pharmacology.

The genus Daphne belongs to the Thymeleaceae family and contains over 90 species that are distributed in Asia, Europe and parts of North Africa. The species of the genus Daphne are used in the traditional medicine of China, Tibet, Korea, and the Middle East for the treatment of various conditions. A broad range of studies has shown the significant biological potential of these species as sources of biologically and pharmacologically active compounds.

Chemical composition and anti-herpes simplex virus type 1 (HSV-1) activity of extracts from Cornus canadensis.

Background: Many plants of boreal forest of Quebec have been used by Native Americans to treat a variety of microbial infections. However, the antiviral activities of these plants have been seldom evaluated on cellular models to validate their in vitro efficiencies. In this study, Cornus canadensis L.

Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds.

There is nowadays an urgent need for developing novel generations of antibiotic agents due to the increased resistance of pathogenic bacteria. As a rich reservoir of structurally diverse compounds, plant species hold promise in this regard. Within this framework, we isolated a unique series of antibacterial flavonoids, named balsacones N-U, featuring multiple cinnamyl chains on the flavan skeleton.

DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea.

Eight non-carotenoid tetraterpenoids, abibalsamins C-J (3-10), were isolated from the oleoresin of Abies balsamea. Their chemical structures were determined based on analysis of 1D/2D NMR and MS data. The assignment of their relative configurations was accomplished using homonuclear coupling constants in tandem with ROESY data.

Dirchromones: Cytotoxic Organic Sulfur Compounds Isolated from Dirca palustris.

Eight novel organic sulfur compounds featuring an unprecedented structure among natural organosulfur molecules are reported. The identified compounds, named dirchromones (1-8), were isolated from a dichloromethane extract of the roots, bark, and wood of Dirca palustris, an endemic shrub of eastern North America. Their identification was based on thorough NMR, IR, and HRMS spectroscopic data interpretation.

Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds.

A phytochemical investigation of buds from the hardwood tree Populus balsamifera led to the isolation of six new cinnamoylated dihydrochalcones as pairs of racemates and one as a racemic mixture along with the known compound iryantherin-D (2), the absolute configuration of which was determined for the first time. The structures of balsacones J (1), K (3), L (4), and M (5) were elucidated on the basis of spectroscopic data (1D and 2D NMR, IR, and MS). Chiral HPLC separations were carried out, and the absolute configuration of the isolated enantiomers unambiguously established via X-ray diffraction analyses and electron circular dichroism spectroscopic data.

Isolation of a new disaccharide nucleoside from Helleborus caucasicus: structure elucidation and total synthesis of hellecaucaside A and its β-anomer.

Hellecaucaside A, a new disaccharide nucleoside featuring a 2'-O-α-D-ribofuranosyluridine skeleton and a 4-hydroxybenzoyl group at the 5' position, was isolated from the underground part of Helleborus caucasicus. The structure of the compound was elucidated by means of chemical degradation and spectroscopic analyses, such as 1D/2D NMR, chiral-GC, and HRMS. The total synthesis of hellecaucaside A and its β-anomer was accomplished, unequivocally confirming the structure of the natural product.

A new flavonol glycoside from the medicinal halophyte Suaeda fruticosa.

A new flavonol glycoside, namely 3-(α-rhamnopyranosyl-(1 → 2)-[β-xylopyranosyl-(1 → 6)]-β-glucopyranosyloxy) isorhamnetin was reported from methanol extracts of aerial parts of Suaeda fruticosa for the first time. In this work, liquid chromatography coupled to atmospheric pressure chemical ionisation mass spectrometry, high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy were used to identify this new compound. Structure was elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC and (1)H-(1)H COSY.

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin.

Phytochemical analysis of A. balsamea oleoresin led to the isolation of three new 3,4-seco-lanostane triterpenoids 1-3, one new cycloartane triterpenoid 4 along with fourteen known terpenoids. Structure determinations were based on extensive 1D/2D NMR, IR and MS spectroscopic analyses, and comparison with literature data.

Abibalsamins A and B, two new tetraterpenoids from Abies balsamea oleoresin.

Abibalsamins A (1) and B (2), two unprecedented tetraterpenoids featuring a 3,4-seco-rearranged lanostane system fused with a β-myrcene lateral chain via a [4 + 2] Diels-Alder cycloaddition, were isolated from the oleoresin of Abies balsamea. Their structures were elucidated by means of extensive 2D NMR, IR, and MS spectroscopy analyses. The absolute configuration of 1 was determined by single-crystal X-ray diffraction.

Antioxidant and anti-inflammatory activities of quercetin 7-O-β-D-glucopyranoside from the leaves of Brasenia schreberi.

Brasenia schreberi Gmel. (Cabombaceae) is an aquatic plant that grows in eastern Asia, Australia, Africa, and North and Central America. B.

Cytotoxic activity of withanolides isolated from Tunisian Datura metel L.

Withanolide-type steroids, withametelin Q (1) and 12α-hydroxydaturametelin B (2) along with three known withanolides, were isolated from leaves of Datura metel L. (Solanaceae). The respective structures, characterized mainly by NMR spectroscopy, were identified as (20R,22R,24R)-21,24-epoxy-1α,3β-dihydroxywitha-5,25(27)-dienolide-3-O-β-D-glucopyranoside (1) and (20R,22R,24R)-12α,21,27-trihydroxy-1-oxowitha-2,5,24-trienolide-27-O-β-D-glucopyranoside (2).

New triterpenoid saponins from Leontice smirnowii.

Three new triterpene saponins, leonticins I (1), J (2) and L (3) were isolated from the tubers of Leontice smirnowii. On the basis of spectroscopic methods, including 2D NMR experiments (DEPT, gs-COSY, gs-HMQC, gs-HMBC and gs-HSQC-TOCSY), mass spectrometry (HR-ESI-MS) and chemical degradation, the structures of the new compounds were elucidated as 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-1 → 2)]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (2) and 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)]-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid (3), respectively. The aglycone 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid was observed for the first time in Leontice species.

Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins.

The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural lupane- and oleanane-type saponins were evaluated and the structure-activity relationships were established. It was shown that lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 microM) independently of the nature of the sugar moieties.

Cytotoxic steroidal saponins from the flowers of Allium leucanthum.

Allium leucanthum C. Koch is an endemic Caucasian species that grows in Georgia. The flowers are used in traditional medicine.

Isolation and identification of cytotoxic compounds from the wood of Pinus resinosa.

Methanol extracts of wood from Pinus resinosa were found to be selectively cytotoxic against human lung carcinoma cells, A549 (IC50 41 +/- 6 microg/mL), human colorectal adenocarcinoma cells, DLD-1 (IC50 47 +/- 4 microg/mL) in comparison with healthy cells, WS1 (IC50 130 +/- 11 microg/mL). Five known compounds were isolated and identified by 1H, 13C NMRspectroscopy and HR-ESI-MS mass spectrometry as, pinosylvin monomethyl ether (1), pinosylvin (2), pinosylvin dimethyl ether (3), pinobanksin (4) and (-)-norachelogenin (5). Compound 4 was isolated for the first time in P.

Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera.

Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC(50) values ranging from 10.

Antioxidant, anti-inflammatory and anticancer activities of methanolic extracts from Ledum groenlandicum Retzius.

Labrador tea (Ledum groenlandicum Retzius) is an ericaceae widely distributed in North America. The leaves and twigs were used in Native American traditional medicine to treat several inflammatory pathologies such as asthma, rheumatisms and burns. Reactive oxygen species as well as reactive nitrogen species such as nitric oxide (NO) contribute significantly to these pathologies.

New labdane diterpenes from the stem bark of Larix laricina.

Two new labdane diterpenes, cis-19-hydroxyabienol (1) and 8alpha-hydroxy-12Z,14-labdadien-19-al (2), along with another labdane described for the first time in the genus Larix, 19-acetoxy-13S-hydroxy-8(17),14-labdadiene (3) and a stilbene, 3-methoxy-3,3',5'-trihydroxystilbene (4), were isolated from the stem bark of Larch (Larix laricina). Their structures were established by standard chemical and spectroscopic methods. Compounds 2 and 3 were shown to be moderately cytotoxic against A-549, DLD-1 and normal skin fibroblast cell lines, WS1.

The antioxidant activity of a triterpenoid glycoside isolated from the berries of Hedera colchica: 3-O-(beta-D-glucopyranosyl)-hederagenin.

The antioxidant activity of a triterpenoid glycoside [3-O-(beta-D-glucopyranosyl)-hederagenin; OGH] isolated from the berries of Hedera colchica, an ivy species endemic in Georgia, was investigated. The antioxidant properties of OGH were evaluated using different antioxidant assays: 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH.) scavenging, total antioxidant activity, reducing power, superoxide anion radical (O2*-)) scavenging, hydrogen peroxide (H2O2) scavenging and metal chelating activities.

Triterpenoid saponins from leaves of Hedera pastuchowii.

Five new triterpenoid saponins, pastuchoside A (1), B (3), C (5), D (7) and E (9), were isolated from the leaves of Hedera pastuchowii. They have oleanolic acid or hederagenin as aglycone. The structures were established by NMR spectroscopy including gs (gradient selected)-COSY, gs-HSQC, gs-HSQC-TOCSY and gs-HMBC experiments, and mass spectrometry (ESI-HR-MS).

Acute and chronic antiinflammatory effects of Hedera colchica in rats.

Hedera helix and Hedera colchica are the members of Araliaceae family. In the present study, we tested the possible antiinflammatory effects of crude (CSE) and purified (SPE) extracts of Hedera colchica in carrageenan- and cotton pellet-induced acute and chronic inflammation models in rats. Both CSE and SPE of Hedera colchica were found to have antiinflammatory effects.

Antioxidant activity of saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F.

The antioxidant activities of alpha-hederin and hederasaponin-C from Hedera helix, and hederacolchisides-E and -F from Hedera colchica were investigated, in this study. The antioxidant properties of the saponins were evaluated using different antioxidant tests: 1,1-di-phenyl-2-picryl-hydrazyl (DPPH.) free radical scavenging, total antioxidant activity, reducing power, superoxide anion radical scavenging, hydrogen peroxide scavenging, and metal chelating activities.