Three new phenylpropanoid glucosides and a new tyramine-type alkamide from Piper puberulum.

Three new phenylpropanoid glycosides, piperpubelide (1), 1-propionyl-3-hydroxy-phenyl-4-O-ß-D-glucopyranoside (2), and 1-propionyl-4-hydroxy-phenyl-3-O-ß-D-glucopyranoside (3), a new tyramine-type alkamide, puberulumine L (4), together with thirteen known compounds (5-17) were isolated from Piper puberulum (Benth.) Maxim. Their structures were elucidated by analysis of spectroscopic data involving NMR, IR, UV, and HRESIMS data. Calculated and experimental ECD was used to confirm the configuration of compound 1. Compounds 14, 16, and 17 exhibited relatively positive DPPH radical scavenging activities, with corresponding EC50 of 10.23, 24.12, and 21.83 µM, respectively. In addition, compound 5 inhibited LPS-induced NO production in BV-2 microglia with an IC50 value of 18.05 µM.

New lignans and phenylethanoid with antioxidant activity from aerial parts of Forsythia suspensa (Thunb.) Vahl.

Two new lignans, phillyroside A(1) and phillyroside B(2), together with three new phenylethanoid glycoside, forsythoside K(3), forsythoside L(5) and forsythol L (4), while compounds 4 was an aglycon of forsythoside L(5), were isolated from the aerial parts of Forsythia suspensa (Thunb.) Vahl. Their structures were elucidated by comprehensive analyses of standard spectroscopic data (MS, IR, and NMR) and the in vitro antioxidant activity of five new compounds were evaluated in DPPH and ABTS radical scavenging experiment and ferric reducing ability of plasma (FRAP) experiment. Compounds 4 and 5 exhibited antioxidant activity with IC50 values ranging from 112.49 to 153.58 µM in DPPH experiment and 45.43 to 64.09 µM in ABTS experiment.

Constituents of Tinospora sinensis and their nitric oxide inhibitory activities.

One new phenylpropanoid glycoside, tinosinen A (1) and 13 known compounds, tinosinen (2), citrusin B (3), picraquassioside C (4), erythro-guaiacylglycerol-ß-O-4'-coniferyl alcohol (5), erythro-guaiacylglycerol-8-O-4'-(sinapyl alcohol) ether (6), erythro-syringylglycerol-8-O-4'-(sinapyl alcohol) ether (7), seco-isolariciresinol 9-O-D-ß-glucopyranoside (8), tinosposide A (9), pinoresinol-4'-O-ß-D-glucopyranoside (10), syringaresinol-4'-O-ß-D-glucopyranoside (11), pinoresinol (12), syringaresinol (13), and lirioresino-ß-dimethyl ether (14) were isolated from the stems of Tinospora sinensis (Lour.) Merr. Their structures were established by detailed spectroscopic studies and comparisons with those reported in the literature. Compound 13 showed significant inhibitory NO production (IC50 value of 38.53 ± 1.90 µM) in RAW264.7 macrophages, LPS-stimulated. Compounds 3-7, 11, 12, and 14 inhibited NO production with IC50 values ranging from 38.53 to 99.07 µM.

One new phenylpropanoid glycoside from Myxopyrum smilacifolium with α-glucosidase inhibitory activity.

One new phenylpropanoid glycoside, myxosmoside I (1) and six known compounds, arenarioside (2), verbacoside (3), 3-formylindole (4), 5-hydroxymethyl furfural (5), D-manitol (6), and glycerol monooleate (7) were isolated from the roots of Myxopyrum smilacifolium (Wall.) Blume. Their chemical structures were determined by 1D-, 2D-NMR, and mass spectra, chemical methods, and compared with those reported in the literature. All compounds were evaluated for α-glucosidase inhibitory effect. Among them, phenylpropanoid glycosides 1-3 significantly inhibited α-glucosidase activity with IC50 values of 30.0 ± 0.9, 66.6 ± 2.3, and 36.9 ± 2.0 µM, respectively.

Flavonol glycosides and phenylpropanoid glycosides with inhibitory effects on microglial nitric oxide production from Neoshirakia japonica.

Five new flavonol glycosides (1-5), one new phenylpropanoid glycoside (6), and nine known glycosides (7-15) were isolated from the stems and leaves of Neoshirakia japonica. The structures of the new compounds were determined by detailed analysis of spectroscopic data (HRESIMS, 1D and 2D NMR) and acid hydrolysis experiment. The antineuroinflammatory effects of all the isolates were evaluated by inhibiting NO production against LPS-induced BV-2 microglial cells. Compounds 1, 8, and 9 showed more potent inhibitory activities with IC50 values of 2.7, 5.5, and 4.1 µM, respectively, than that of the positive control minocycline (IC50 = 15.6 µM), while compounds 7 (IC50 = 17.0 µM) and 10 (IC50 = 24.3 µM) also displayed inhibitory activities to a certain degree.

Triterpenoid saponins and phenylpropanoid glycoside from the roots of Ardisia crenata and their cytotoxic activities.

Two new triterpenoid saponins, ardisicrenoside R and S (1 and 2), and one new phenylpropanoid glycoside, ardicrephenin (3), along with five known compounds (4-8), were isolated from roots of Ardisia crenata. Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods. Compounds 2-7 were evaluated for their cytotoxic activities against A549, MCF-7, HepG2 and MDA-MB-231 cell lines by MTT assay. Ardicrenin (6) showed significant cytotoxicity, with IC50 values of 1.17 ± 0.01, 1.19 ± 0.06, 3.52 ± 0.23, and 16.61 ± 1.02 µmol·L-1, respectively.

New and known phenylpropanoid glycosides from mountain cultivated ginseng.

Two new phenylpropanoid glycosides elucidated as 2,6-dimethoxyphenyl-4-propylene-1-O-ß-D-apiofuranosyl-(1-6)-ß-D-glucopyranoside (1) and 2-methoxyphenyl-4-propylene-1-O-ß-D-apiofuranosyl-(1-6)-ß-D-glucopyranoside (2), along with three known phenylpropanoid glycosides (3-5) were isolated from Mountain Cultivated Ginseng. The structures of compounds 1-5 were elucidated on the basis of comprehensive spectroscopic data including 1D, 2D NMR spectra, and MS. In addition, in vitro cytotoxicity of all the isolated compounds was evaluated against HELA cell.

Triterpenoid saponins and phenylpropanoid glycoside from the roots of Ardisia crenata and their cytotoxic activities / 中国天然药物

Two new triterpenoid saponins, ardisicrenoside R and S (1 and 2), and one new phenylpropanoid glycoside, ardicrephenin (3), along with five known compounds (4-8), were isolated from roots of Ardisia crenata. Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods. Compounds 2-7 were evaluated for their cytotoxic activities against A549, MCF-7, HepG2 and MDA-MB-231 cell lines by MTT assay. Ardicrenin (6) showed significant cytotoxicity, with IC

A new neolignan glycoside from Dolomiaea souliei.

One new neolignan glycoside, dolomiside A (1), together with 11 known phenylpropanoid glycosides were isolated from Dolomiaea souliei (Franch.) Shih. The structures of these isolates were determined by UV, CD, HR-ESI-TOFMS, 1D and 2D NMR analysis.

A new phenylpropanoid glycoside from leaves of Platycladus orientalis / 中草药

Objective: To study the chemical constituents from the leaves of Platycladus orientalis, as well as their antioxidant and α-glucosidase inhibitory activities. Methods: The compounds were isolated and purified by silica gel, MCI, polyamide, and prep-HPLC chromatography, their structures were elucidated by spectral analysis. DPPH and ABTS methods were used to study the antioxidant activity, and pNPG method was used to study the α-glucosidase inhibitory activity. Results: Eleven compounds (1-11) were isolated from the 80% ethanol extract of the leaves of P. orientalis, and identified as 4-O-(1’,3’-dihydroxypropan-2’-yl)- dihydroconiferyl alcohol 9-O-β-D-glucopyranoside (1), myricetrin (2), 5,8,3’,4’-tetrahydroxy-flavone-7-O-β-D-xylopyranoside (3), isomassonianoside B (4), (-)-isopramine 9’-O-β-D-glucopyranoside (5), (7R,8S,7’S,8’R)-4,9,4’,7’-tetrahydroxy-3,3’-dimethoxy- 7,9’-epoxylignan 4-O-β-D-glucopyranoside (6), sugiol (7), totarol (8), 5,6-dehydrosugiol methyl ether (9), isopimara-8,15-dien-7-one (10) and ethanol α-L-rhamnopyranoside (11). Conclusion: Compound 1 is a new compound, named as platycloside A; In the known compounds, seven compounds (4-7, 9-11) are isolated from this plant for the first time, six compounds (4-6, 9-11) are isolated from the family Thujoideae for the first time, and four compounds (5, 6, 10, 11) are isolated from the family Cupresaceae for the first time. The compounds 2-6 showed a degree of antioxidant activities. The compounds 2 and 3 showed the α-glucosidase inhibitory activities.

[A new phenylpropanoid glycoside from fruit of Cornus officinalis].

To investigate the chemical compounds from the ripe fruit of Cornus officinalis, a new phenylpropanoid glycoside 1-O-(6'-O-p-hydroxybenzoyl-ß-D-glucopyranosyl)-p-phenylpropanol, named cornuphenylpropanoid A (1), were separated and purified by D101 macroporous resin, silica gel and ODS column chromatography. Its structure was extensively determined on basis of ¹H-NMR, ¹³C-NMR, DEPT, HSQC, HMBC and HR-ESI-MS spectroscopic data.

Hypolipidemic activity and mechanisms of the total phenylpropanoid glycosides from Ligustrum robustum (Roxb.) Blume by AMPK-SREBP-1c pathway in hamsters fed a high-fat diet.

The aim of this study was to evaluate the hypolipidemic effect and mechanisms of total phenylpropanoid glycosides extracted from Ligustrum robustum (Roxb.) Blume (LRTPG) in hamsters fed a high-fat diet and to discover bioactive components in HepG2 cell model induced by oleic acid. LRTPG of high (1.2 g/kg), medium (0.6 g/kg), and low (0.3 g/kg) doses was administrated daily for 21 consecutive days in hamsters. We found that in hamsters fed a high-fat diet, LRTPG effectively reduced the concentrations of plasma triglycerides (TG), free fatty acid, total cholesterol, low-density lipoprotein cholesterol, and hepatic TG and total cholesterol. And the compounds acteoside, ligupurpuroside A, ligupurpuroside C, and ligupurpuroside D significantly inhibited lipid accumulation in HepG2 cell at the concentration of 50 µmol/L. Mechanism research demonstrated that LRTPG increased the levels of phospho-AMP-activated protein kinase and phospho-sterol regulatory element binding protein-1c in liver, further to suppress the downstream lipogenic genes as stearoyl-CoA desaturase 1, glycerol-3-phosphate acyltransferase, 1-acylglycerol-3-phosphate O-acyltransferase 2, and diacylglycerol acyltransferase 2. In addition, LRTPG increased the hydrolysis of circulating TG by up-regulating lipoprotein lipase activities. These results indicate that LRTPG prevents hyperlipidemia via activation of hepatic AMP-activated protein kinase-sterol regulatory element binding protein-1c pathway.

First total synthesis of a new phenylpropanoid glycoside: natural cytotoxic compound from Cirsium japonicum.

Phenylpropanoid glycoside compound 1, the natural anti-tumor compound isolated from the erial parts of Cirsium japonicum, was first totally synthesized using easily available materials in short, convenient route with overall yield of 13.9%.

Characterization of binding interactions between selected phenylpropanoid glycosides and trypsin.

Phenylpropanoid glycosides (PPGs) are important bioactive polyphenolic compounds that are widely distributed in plants. In this paper, the inhibitory effects of four selected PPGs against trypsin were investigated. The interactions between these PPGs and trypsin were further investigated by multiple spectroscopic methods and molecular docking studies. The results showed that the binding of each of these PPGs to trypsin induced changes in the natural conformation of trypsin, which inhibited the enzyme in the following order: acteoside>syringalide A 3'-α-l-rhamnopyranoside>lipedoside A-I>osmanthuside B. The binding constant (Ka) values followed the same trend. The hydrogen bond force played an important role in the interaction between each PPG and trypsin. Interestingly, the binding affinity and inhibitory effect increased as the number of phenolic hydroxyl groups increased. In addition, the effect of the phenolic hydroxyl group on the A ring had a greater effect than one on the B ring.

Two pairs of unusual melibiose and raffinose esters from Scrophularia ningpoensis.

A pair of unusual melibiose esters (1α/1ß) and a pair of unusual raffinose esters (2α/2ß), were isolated from Scrophularia ningpoensis. Structures of them were established by detailed spectroscopic analyses to be 6-O-(E)-cinnamoyl-α-d-galactopyranosyl-(1→6)-α(ß)-d-glucopyranose (1α/1ß) and 6-O-(E)/(Z)-cinnamoyl-α-d-galactopyranosyl-(1→6)-α-d-glucopyranosyl-(1→2)-ß-d-fructofuranose (2α/2ß), respectively. All these compounds were evaluated for antifouling activity against the settlement of Balanus amphitrite larvae, along with the cytotoxic effect against the proliferation of HeLa cell lines.

A new phenylpropanoid glycoside from fruit of Cornus officinalis / 中国中药杂志

To investigate the chemical compounds from the ripe fruit of Cornus officinalis, a new phenylpropanoid glycoside 1-O-(6'-O-p-hydroxybenzoyl-β-D-glucopyranosyl)-p-phenylpropanol, named cornuphenylpropanoid A (1), were separated and purified by D101 macroporous resin, silica gel and ODS column chromatography. Its structure was extensively determined on basis of ¹H-NMR, ¹³C-NMR, DEPT, HSQC, HMBC and HR-ESI-MS spectroscopic data.

New Phenylpropanoid and Coumarin Glycosides from the Stems of Hydrangea paniculata Sieb.

A new phenylpropanoid glycoside (1), and two new coumarin glycosides (2, 3), together with two known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 µM) exhibited significant hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays.

A new lignan glycoside from the stems of Zanthoxylum armatum DC.

A new lignan glycoside, (7S,8R)-guaiacylglycerol-ferulic acid ether-7-O-ß-D-glucopyranoside (1), along with five known phenylpropanoids (2-6) and seven phenylpropanoid glycosides (7-13), were isolated from the stems of Zanthoxylum armatum DC. Their structures were elucidated by spectroscopic analysis. Compounds 2-8 and 11-13 were first isolated from Rutaceae and the others were isolated for the first time from Z. armatum.

Hypolipidemic activity of total phenylpropanoid glycosides fromLigustrum robustum(Roxb.) Blume and its mechanisms on AMPK pathway / 中国药理学通报

Aim To evaluate the hypolipidemic effect of total phenylpropanoid glycoside extracted from Ligustrum robustum(Roxb.)Blume(CNTG)and its mecha-nisms.Methods The 60 hamsters were randomly divided into six groups,namely the control group,the model group,the positive control group(fenofibrate,150 mg·kg-1),the high(1 200 mg·kg-1),medium(600 mg·kg-1)and low(300 mg·kg-1)doses of CNTG groups.Only the control group was given control diet and other groups received high-fat diet.The changes of serum lipid were measured and analyzed in 1st week to ensure the successful establishment of the model.The drugs were administered daily for four weeks and the concentrations of lipids were determined in the 2nd week,3rd week and 4th week respectively.Quantitative real-time PCR and Western blot were used to assay the mRNA and protein expression of related signaling enzymes and proteins.Results Compared with the model group,the concentrations of serum TG,TC,LDL-C(P<0.05,P<0.01)and hepatic TG,TC(P<0.01)were effectively reduced in hamsters in CNTG-treated groups.Mechanism research found that CNTG increased the levels of phospho-AMPKα,LKB1 and phospho-LKB1 in liver(P<0.05).Conclusion CNTG prevents hyperlipidemia via activation of hepatic LKB1-AMPK pathway.

Cytotoxic phenylpropanoid glycosides from Cirsium japonicum.

Three new phenylpropanoid glycosides 1-3, along with nine known phenylpropanoid glycosides 4-12, were isolated from the aerial parts of Cirsium japonicum. The structures of isolated compounds were elucidated by chemical and spectroscopic methods. Compounds 1, 3, 6, 8, and 11 showed moderate cytotoxicities against MCF-7, U87, HCT116, and A549 cell lines with IC50 values in the range of 1.35-11.32 µM. The known compounds 4-12 were obtained from this plant for the first time.