A new isoflavone glycoside from Pueraria alopecuroides

A new isoflavone glycoside, (?)-tuberosin-3-O-β-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

A new flavonol glycoside from the florets of Carthamus tinctorius L.

One new flavonol glycoside, 6-hydroxykaempferol-3-O-β-D-glucoside-7-O-β-D-glucuronide (1), together with eight known flavonoids and three known quinochalcones, was isolated from the florets of Carthamus tinctorius L. Their structures were determined by extensive spectroscopic analyses. Their cardioprotective effects against H₂O₂-induced apoptosis in H9c2 cells were also evaluated; compounds 1, 2, 4–5, 7–10 and 12 provided significant protective effects on H₂O₂-induced H9c2 cells at the concentration of 25 μg/mL.     

Chemical constituents from seeds of <Emphasis Type="Italic">Lactuca sativa</Emphasis>

A new flavonol glycoside with a rare structure type, lactucasativoside A (1), was isolated from the seeds of Lactuca sativa, together with three known compounds, japonicin A (2), isoquercitrin (3), and caffeic acid (4). Their structures were established on the basis of extensive spectroscopic analysis. Compound 2 was obtained from the genus Lactuca for the first time.     

β-Hydroxydihydrochalcone and flavonoid glycosides along with triterpene saponin and sesquiterpene from the herbs of Pimpinella rhodantha Boiss.

A new β-hydroxydihydrochalcone glycoside named ziganin (1) and a new acylated flavonol glycoside named isorhamnetin-3-O-α-L-(2″,3″-di-O-trans-coumaroyl)-rhamnopyranoside) (2), along with two known flavonoid glycosides, a β-hydroxydihydrochalcone glycoside, a hydroxybenzoic acid derivative, a trinorguaiane type sesquiterpenoid, a triterpenic saponin and a polyol were isolated from the herbs of Pimpinella rhodantha Boiss. Their structures were elucidated on the basis of spectroscopic analyses including 1D-and 2D-NMR, UV, IR, CD, ESI-MS, APCI-MS, HR-ESI-MS techniques. The isolated compounds were evaluated for their antioxidant capacity through the DPPH free-radical scavenging assay and ferrous ion-chelating power test.     

A new flavonoid glycoside from Elsholtzia bodinieri

A new flavonoid glycoside, eriodictyol 7-O-(6″-caffeoyl)-β-D-glucopyranoside (1), along with 14 known compounds, were isolated from the whole plants of Elsholtzia bodinieri. All of the structures were determined by spectroscopic methods and chemical transformation. Compound 1 and luteolin (9) exhibited potent anti-HCV activities with a selective index of 135.85 and 20.84, respectively.     

Dalvelutinoside,a new isoflavone glycoside from the methanol extract of Dalbergia velutina roots

A new isoflavone glycoside, dalvelutinoside (1), together with one known isoflavone (2) and five known isoflavone glycosides (3–7) were isolated from the methanol extract of the roots of Dalbergia velutina. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines.     

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

Chemical constituents from the fruits of <Emphasis Type="Italic">Ligustrum lucidum</Emphasis>

One new δ-valerolactone (1) and one new natural phenolic glycoside 2, together with four known compounds 3–6, were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated on the basis of spectral data. The chemical transformation from 2 to 3 was observed. The immunomodulatory activities of the compounds were also evaluated.     

New lignan glycosides from Cissus quadrangularis stems

Phytochemical investigation of Cissus quadrangularis stems led to the isolation of one new phenolic glycoside (1) and two new lignan glycosides (7 &; 8) along with twelve known compounds (2–6 &; 9–15). Their chemical structures were determined on the basis of extensive spectroscopic analysis using 1D, 2D NMR, and mass spectrometric analysis. Among the known compounds, 4–6, 9 and 12 were isolated for the first time from the genus Cissus whereas compounds 10, 11 and 13 for the first time from this plant.     

A new methylene bisflavan-3-ol from the branches and leaves of Potentilla fruticosa

Abstract

Dasiphora fruticosa L. (Rosaceae), also known as Potentilla fruticosa L. (syn.), is a hardy deciduous shrub widely distributed in the north temperate regions of the world. Three methylene bisflavan-3-ols (1-3), together with a procyanidin dimer, (-)-afzelechin-(4α→8)-(-)-afzelechin (4) were isolated for the first time from the branches and leaves of the titled plant, in addition to 11 known compounds (5-15). Their structures were elucidated by means of extensive spectroscopic analysis and by comparison with data reported in the literatures. Methylene 6,8-bis(7-O-glucosyl) catechin (1) was determined to be a new dimeric flavan-3-ol glycoside through a methylene linkage between C-8 and C-8 of two units. At a concentration of 128?μg/mL, the known compounds 9 – 13 exhibited antibacterial activities on Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. Compound 12 also showed certain glucose uptake stimulating activity.     

A new phenolic glycoside from Saprosma merrillii

A new phenolic glycoside derivative, saproglucoside (1), along with five known phenolic glycoside derivatives (2–6) were isolated from the stems of Saprosma merrillii. The structure of the new compound 1 was determined by 1D and 2D NMR as well as by HRESIMS and hydrolysis. The inhibitory activities of all compounds against seven pathogenic bacteria and two cancer cell lines were evaluated.     

Iridoid,phenylethanoid and flavonoid glycosides from Forsythia suspensa

Abstract

As part of our continuing efforts to explore bioactive compounds from natural resources, a new iridoid glycoside, adoxosidic acid-6′-oleuroperic ester (1), together with one known phenylethanoid glycoside (2) and two known flavonoid glycosides (3–4) were isolated from the fruit of Forsythia suspensa. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data and HR-ESIMS. Interestingly, compound 1 was a monoterpene ester of one iridoid glycoside. Compounds 2–4 were identified as calceolarioside A (2), kaempferol-3-O-rutinoside (3), kampferol-3-O-robinobioside (4) on the basis of NMR spectroscopic data analyses and comparison with the data reported in the literature. The antiviral activity aganisist influenza A (H5N1) virus of compound 1 was studied as well.     

A new dihydrochalcone glycoside from the stems of Homalium stenophyllum

A new dihydrochalcone glycoside, phloretin-4-O-β-D-glucopyranoside (1), together with seven known flavonoids (2–8), were isolated from the stems of Homalium stenophyllum. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. The known compounds (2–8) were isolated from the genus Homalium for the first time. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro.     

A new phenolic glycoside and two new monoterpenoid furocoumarins from Aurantii Fructus Immaturus

A new phenolic glycoside, citrauranoside A (1), and two new monoterpenoid furocoumarins, citraurancoumarin A (2) and citraurancoumarin B (3), along with four known compounds (4–7) were isolated from the young fruit of Citrus aurantium L. The structures were elucidated by their comprehensive analysis including 1D, 2DNMR, IR and mass spectra.     

A new antiviral pregnane from a gorgonian-derived Cladosporium sp. fungus

A new pregnane, 3α-hydroxy-7-ene-6,20-dione (1), and five known steroids (2–6), along with one known steroidal glycoside (7) were obtained from the fungus Cladosporium sp. WZ-2008-0042 cultured from a gorgonian Dichotella gemmacea collected from the South China Sea. The structure and absolute configuration of the new compound (1) were elucidated by comprehensive spectroscopic data and X-ray diffraction data. The compound has a rare configuration of 3α-OH that is different from most of pregnanes. All of the isolated compounds were evaluated for their antiviral activities against respiratory syncytial virus (RSV). Among them, 1 exhibited potential antiviral activity with the IC₅₀ value of 0.12 mM.     

A new phenylethanoid glycoside from Orobanche cernua Loefling

A novel phenylethanoid glycoside, 3′-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1–3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3′-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC₅₀ values of 71.89, 36.97 μg/mL and 32.32, 34.58 μg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively.     

A new antifungal eudesmanolide glycoside isolated from Sphaeranthus indicus Linn. (Family Compositae)

A new antifungal eudesmanolide glycoside 11,13-dihydro-3-O-(β-digitoxopyranose)-7α-hydroxy eudasman-6,12-olide (2) in addition to known compounds 1 and 3, has been isolated from Sphaeranthus indicus Linn. Its structure was determined by spectral analysis (UV, IR, 1D and 2D NMR and mass spectrum).     

A new flavanone glycoside isolated from Tournefortia sibirica

A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and four known compounds (2–5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1?D and 2?D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1–5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1–5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.     

A new phenolic glycoside from the Idesia polycarpa Maxim. leaves

Phytochemical investigation on the ethyl acetate extract of Idesia polycarpa Maxim. Leaves led to the isolation of four phenolic glycoside isomers (1–4). Compound 2 appeared to be new reported phenolic glycoside, while compound 1 was the first time isolated from the titled species. Their structures were established by IR, UV, HRESI-MS and 1D and 2D NMR spectroscopies analysis and comparison of spectral data with previously reported data. The compounds 3 and 4 showed stronger activity of scavenging the DPPH free radical than the other two compounds, while the compounds 1 and 2 showed a significant activity of scavenging the ABTS free radical. Compounds 2 and 4 exhibited stronger cytotoxicity against HepG2 cell lines compared to compounds 1 and 3. Moreover, compound 3 presented the highest cytotoxicity against MCF cell lines with IC₅₀ value of 37.17?±?0.26?μg/mL than compounds 1, 2 and 4.