Antinociceptive and anti-inflammatory activities of iridoid glycosides extract of Lamiophlomis rotata (Benth.) Kudo

Lamiophlomis rotata (Benth.) Kudo is a perennial herb (Labiatae) used as the Tibetan traditional medicine with the effects of alleviating pain, detumescence, hemostasis, promoting blood circulation to remove blood stasis and reinforcing marrow. In this study, we investigated the antinociceptive and anti-inflammatory activities of iridoid glycosides extract of L. rotata (IGLR) in mice. Our results showed that the iridoid glycosides extract could decrease acetic-acid-induced writhings times and formalin-induced lickings times, inhibit carrageenan-induced hind paw edema and xylene-induced ear swelling, and suppress peritoneal capillary permeability and leukocyte infiltration also induced by acetic acid in mice. All of these results suggested that the iridoid glycosides extract possesses the significant antinociceptive and anti-inflammatory activities.     

Insecticidal activity of Vitex mollis

Organic extracts from the leaves of Vitex mollis were assessed for their toxic effect on fall armyworm neonate larvae (Spodoptera frugiperda), an important insect pest of corn. The extracts showed insecticidal and insect growth regulatory activity, being CHCl(3)-MeOH (1:1) extract the most active, also found to be toxic in the Artemia salina test.     

A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis

A new phenylpropanoid glycosides, 2-feruloyl-O-alpha-D-glucopyranoyl-(1'-->2)-3,6-O-feruloyl-beta-D-fructofuranoside, was isolated from the root of Paris polyphylla var. yunnanensis. The structure of the new glycoside was elucidated by spectroscopic methods. Cytotoxicity test showed that it has cytotoxic effect in a dose-dependent manner against the mice lung adenocarcinoma cell line (LA795).     

A new iridoid glycoside from Linaria genestifolia

A new iridoid glycoside named genestifolioside (1) was isolated from the ethanol extract of Linaria genestifolia. Its structure was defined by spectral analysis.     

An iridoid and a flavonoid from Sideritis lanata L

A new iridoid diglucoside, 10-O-(E)-p-coumaroylmelittoside (1) and a new flavone glucoside, O-(6'-O-Acetyl-)-beta-glucopyranosylchrysoeriol (2), together with four known flavone glycosides, were isolated from the aerial parts of Sideritis lanata. The structures of the new compounds were elucidated by spectroscopic methods, 2D NMR and MS.     

Sulfur-containing iridoid glucosides from Paederia scandens

A new sulfur-containing iridoid glucoside, named paederoside B, was isolated from the stems of Paederia scandens. The structure of the new compound was elucidated as paederosidyl paederosidate by spectral evidence.     

Antiproliferative steroidal glycosides from Digitalis ciliata

Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5–7) and cardenolide (8–10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1–10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC₅₀ values ranging from 8.3 to 20 μM. The effects of compounds 1–10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G₂/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G₂/M phase of the cell cycle.     

Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana

From the MeOH extract of Sideritis trojana, a new iridoid glycoside, 10-O-(E)-feruloylmelittoside (1) was obtained in addition to four known iridoid glycosides [melittoside (2), 10-O-(E)-p-coumaroylmelittoside (3), stachysosides E (4) and G (5)]. Moreover, five phenylethanoid glycosides [verbascoside (6), isoacteoside (7), lamalboside (8), leonoside A (9), isolavandulifolioside (10), three flavone glycosides (isoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (11), 4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (12), 3'-hydroxy-4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (13) and a benzylalcohol derivative (di-O-methylcrenatin) were obtained and identified. The structures were elucidated on the basis of NMR and HRMS data. All compounds were tested for their antioxidant activity by in vitro TEAC assay and some of them exhibited moderate activity (0.97-1.44 mM) when compared with the reference compound (quercetin 1.86 mM). Glycosides 6-13, the most active compounds in the TEAC assay, were also tested by flow cytometry to evaluate their ability to affect the levels of reactive oxygen species (ROS) in human prostate cancer cells (PC3).     

Two new iridoid glucosides from Hedyotis diffusa

Two new iridoid glucosides, named diffusosides A and B, were isolated from the aerial part of Hedyotis diffusa Willd. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis and HRESIMS. These two compounds showed no cytotoxic activity against SMMC-7721, SW480, SW620, Bel7402, and HepG2 cells.     

Antioxidative and radical scavenging effects of phenolics from Vicia sativum

An acetone extract of Vicia sativum seeds and fractions, comprising low molecular-weight phenolics and tannins, displayed good antioxidant activity.     

New coumarin glycosides from Rhododendron lepidotum

Two new coumarin glycosides, named Rhodonin (1) and Rhodonetin (2) were isolated from the aerial parts of Rhododendron lepidotum.     

New flavonol glycosides from Aconitum burnatii Gáyer and Aconitum variegatum L.

Six flavonol glycosides, compounds 1-3 from A. burnatii Gáyer and 4-6 from A. variegatum L., were obtained from their methanol extracts of aerial parts. The identified structures were quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-p-coumaroyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (1), quercetin 3-O-β-d-glucopyranoside-7-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (2), quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-caffeoyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (3), kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-arabinopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), and kaempferol 3-O-β-d-glucopyranoside (6). Compounds 1, 2 and 4 were isolated for the first time. The antioxidant potential of the methanol extracts and pure compounds was tested with different assays.     

Radical scavenging capacity of Agrimonia eupatoria and Agrimonia procera

The antioxidant activity of Agrimonia eupatoria (Agrimony) and Agrimonia procera (Fragrant agrimony) extracts was assessed by measuring in DPPH radical scavenging and ABTS(+) radical decolourisation reaction systems. Radical scavenging capacity of agrimony extracts varied in a wide range (9.1-97.5% in DPPH reaction and 6.7-79.5% in ABTS reaction) depending on the polarity of the solvent used to obtain the extract.     

New monoterpene glycosides from Paeonia lactiflora

Three new monoterpene glycosides named 4-O-methyl-paeoniflorin (1), isopaeoniflorin (2), and isobenzoylpaeoniflorin (3), together with two known monoterpene glycosides, paeoniflorin (4) and benzoylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora. Their structures were established on the basis of spectral and chemical evidence.     

Antimicrobial and free radical scavenging activities of Teucrium montanum

The antimicrobial and free radical scavenging activities of petroleum ether, chloroform, ethyl acetate, n-butanol and water extracts of Teucrium montanum were investigated. Ethyl acetate, chloroform and n-butanol extracts expressed a wide range of inhibiting activity against both Gram (+) and Gram (-) bacteria. n-Butanol extract possessed potent DPPH free radical scavenging activity.     

Potent antiviral flavone glycosides from Ficus benjamina leaves

Crude ethanol extracts from Ficus benjamina leaves strongly inhibit Herpes Simplex Virus 1 and 2 (HSV-1/2) as well as Varicella Zoster Virus (VZV) cell infection in vitro. Bioassay-guided fractionation of the crude extract demonstrated that the most efficient inhibition of HSV-1 and HSV-2 was obtained with the flavonoid fraction. The present study was aimed to further isolate, purify and identify substances with potent antiviral activity from the flavonoid fraction of F. benjamina extracts. Flavonoids were collected from the leaf ethanol extracts through repeated purification procedure and HPLC analysis. The antiviral activity of each substance was then evaluated in cell culture. Three known flavone glycosides, (1) quercetin 3-O-rutinoside, (2) kaempferol 3-O-rutinoside and (3) kaempferol 3-O-robinobioside, showing highest antiviral efficiency were selected and their structure was determined by spectroscopic analyses including NMR and mass spectrometry (MS). These three flavones were highly effective against HSV-1 reaching a selectivity index (SI) of 266, 100 and 666 for compound 1, 2 and 3, respectively, while the SI of their aglycons, quercetin and kaempferol amounted only in 7.1 and 3.2, respectively. Kaempferol 3-O-robinobioside showed similar SI to that of acyclovir (ACV), the standard anti-HSV drug. Although highly effective against HSV-1 and HSV-2, these flavone glycosides did not show any significant activity against VZV.     

Antioxidant activity of Pyrrosia petiolosa

The ethanol extract of Pyrrosia petiolosa showed an antioxidant activity as determined by free radical scavenging, superoxide radical scavenging, lipid peroxidation, and hydroxyl radical-induced DNA strand scission assays.     

Acylated flavonol glycosides from Epimedium elatum, a plant endemic to the Western Himalayas

Herba Epimedii is a well-known Botanical preparation used over long time in traditional Chinese medicine. The extracts and chemical constituents from Epimedium species are aphrodisiac as well as to treat many ailments. Chemical investigation of lonely species growing in Kashmir Himalaya Epimedium elatum was undertaken to evaluate its chemical profile. Two unusual substituted acylated flavonol glycosides named Elatoside A (1) and Elatoside B (2) have been isolated from the ethanolic extract of E. elatum along with 23 previously known ones (3-25). All isolates were evaluated for antimicrobial and PPAR-γ ligand binding activity, and some of them appeared to be modestly active.     

Isolation and structural characterization of glycosides from an anti-angiogenic extract of Monnina obtusifolia H.B.K.

Angiogenesis, the growth of new blood vessels from the pre-existing vasculature is of physiological and pathological importance. Substantial data over the last decade has implicated uncontrolled angiogenesis with various pathological states. Vascular endothelial growth factors (VEGFs) play a critical role in its regulation, and have become one of the most interesting anti-angiogenesis targets. We have investigated the anti-angiogenic potential of plant extracts in a preliminary ELISA screening. The n-BuOH extract obtained from the leaves of Monnina obtusifolia (Polygalaceae) demonstrated an inhibition of VEGF-A or Placental Growth Factor interaction with Flt-1 (VEGF receptor 1), with an inhibition over 50% in particular for VEGF-A/Flt-1 interaction at a concentration of 500 μg/mL. Successively fractionation of the bioactive n-BuOH extracts of M. obtusifolia aerial parts led to the isolation of six new compounds, 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (1), 1-O-(isopentenyl)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (2), 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(isovaleroyl)-glucopyranose (3), 1-O-(3-methylbut-3enyl)-6-O-β-d-(isovaleroyl)-glucopyranose (4), two new sucrose esters, 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(p-coumaroyl)-glucopyranoside (5), and 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(caffeoyl)-glucopyranoside (6), together with known flavonoids. Their structures were established on the basis of detailed spectral analysis. Since none of the isolated compounds showed a relevant inhibition of VEGFs, the biological activity observed for the butanolic extract might be due to the presence of a combination of compounds acting synergistically.     

Radical scavenging activity and composition of raspberry (Rubus idaeus) leaves from different locations in Lithuania

Raspberry (Rubus idaeus) leaves, collected in different locations of Lithuania were extracted with ethanol and the extracts were tested for their antioxidant activity (AA) by using ABTS(.)(+) decolourisation and DPPH(.) scavenging methods. All extracts were active, with radical scavenging capacity at the used concentrations from 20.5 to 82.5% in DPPH(.) reaction system and from 8.0 to 42.7% in ABTS(.)(+) reaction. The total amount of phenolic compounds in the leaves varied from 4.8 to 12.0 mg of gallic acid equivalents (GAE) in 1 g of plant extract. Quercetin glucuronide, quercetin-3-O-glucoside and rutin were identified in the extracts.