Three new amides from Microlepia pilosissima

Phytochemical investigation of 70% EtOH extract of the dry fronds of Microlepia pilosissima has resulted in isolation of three new amides, (7E)-N-(3′-hydroxyl-4′-methoxy)-phenylethyl-4-hydroxyl-cinnamamide (1), (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-hydroxyl-cinnamamide (2), and (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-methoxy-cinnamamide (3). Their structures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS.     

Four new glycosides from Pleurospermum franchetianum

Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides I, II, III and IV were elucidated to be 16 g , 21 g , 23, 28-tetrahydroxyolean-12-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 2)- g - d -glucopyranoside, 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 4)-[ g - d -glucopyranosyl-(1 M 2)]- g - d -fucopyranoside, 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 4)-[ g - d -fucopyranosyl-(1 M 2)]- g - d -glucopyranoside and 13 g , 28-epoxy-16 g , 23-dihydroxyolean-11-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 3)-[ g - d -glucopyranosyl-(1 M 2)]- g - d -glucopyranoside. The known compounds identified were octadecyl caprate, g -sitosterol, (22 E , 20 S , 24 R )-5 f , 8 f -epidioxy-ergosta-6, 22-dien-3- g -ol, daucosterol, f -spinasterol-3- O - g - d -glucopyranoside, quercetin-3, 7-di- O - g - d -glucopyranoside, kaempferol-3, 7-di- O - f - l -rhamnopyranoside and kaempferol-3- O - g - d -glucopyranosyl-7- O - f - l -rhamnopyranoside, respectively.     

Four new glycosides from Pleurospermum franchetianum

Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides 1, II, III and IV were elucidated to be 16beta, 21beta, 23, 28-tetrahydroxyolean-12-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-fucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-fucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside and 12beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside. The known compounds identified were octadecyl caprate, beta-sitosterol, (22E, 20S, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3-beta-ol, daucosterol, alpha-spinasterol-3-O-beta-D-glucopyranoside, quercetin-3, 7-di-O-beta-D-glucopyranoside, kaempferol-3, 7-di-O-alpha-L-rhamnopyranoside and kaempferol-3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside, respectively.     

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.     

Four new phenolic glycosides from Baoyuan decoction

Four new phenolic glycosides, including two flavonoid glycosides (1 and 2) and two lignan glycosides (3 and 4), were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods. Furthermore, the sources of the four new compounds were determined by the UPLC-Qtrap-MS method, which proved that 1 and 2 are originated from Glycyrrhiza uralensis, and 3 and 4 are from Cinnamomum cassia.     

Four new cucurbitane glycosides from Hemsleya jinfushanensis

A phytochemical study of the tubers of Hemsleya jinfushanensis L. T. Shen resulted in the isolation of four new cucurbitane glycosides, jinfushanosides A-D (1- 4), as well as four known compounds 5-8. Compounds 1-7 were tested for bioactivity against rabbit platelet aggregation induced by PAF, ADP, or AA. Among them, compounds 1, 5, 6 and 7 weakly inhibited PAF-induced platelet aggregation.     

Iridoid and phenylpropanoid glycosides from Pedicularis artselaeri

Six new compounds, an iridoid glucoside, 6- O-methyl-epiaucubin, three iridoids, artselaenins A, B, C, a phenylethanoid glycoside, artselaeroside A, and a phenylpropanoid glycoside, artselaeroside B, as well as fourteen known compounds, nine iridoid glycosides and five phenylpropanoid glycosides were isolated from the whole plants (including roots, stems, leaves and flowers) of Pedicularis artselaeri. Their structures were identified mainly by spectral evidence.     

Smilasides M and N, two new phenylpropanoid glycosides from Smilax riparia

Two new phenylpropanoid glycosides, smilasides M and N, together with the known compound 2',6'-diacetyl-3,6-diferuloylsucrose, were isolated and characterized from the roots and rhizomes of Smilax riparia A. DC. The structures of the new compounds were elucidated as 2',6'-diacetyl-3-Z-feruloyl-6-feruloylsucrose (1) and 2',6'-diacetyl-3-feruloyl-6-Z-feruloylsucrose (2) on the basis of extensive analysis of HR-ESI-MS, UV, IR, and 1D and 2D NMR spectroscopic data.     

Pharmacological effects of three phenylpropanoid glycosides from Mussatia

The phenylpropanoid glycosides 1 (4-cinamoylmussatioside), 2 (4-dimethylcaffeoylmussatioside), and 3 (4-p-methoxycinnamoylmussatioside) isolated from the methanolic extract of Mussatia sp. showed inhibitory action on ADP-induced rat platelet aggregation. The order of activity was 1 greater than 2 greater than 3. This antiplatelet effect is likely to be related to the reported inhibition of cAMP-phosphodiesterase. On the other hand, compounds 1-3 had no effect on blood pressure and heart rate, on microbial growth, or on prostaglandin biosynthesis.     

HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum

Seven phenylpropanoid glycosides named acteoside (1), acteoside isomer (2), leucosceptoside A (3), plantainoside C (4), jionoside D (5), martynoside (6), and isomartynoside (7) were isolated from Clerodendron trichotomum. Compounds 1 and 2 showed potent inhibitory activities against HIV-1 integrase with IC50 values of 7.8 +/- 3.6 and 13.7 +/- 6.0 microM, respectively.     

Antibacterial phenylpropanoid glycosides fromPaulownia tomentosa Steud

The butanol extract of Paulownia tomentosa stem showed antibacterial activity against Staphylococcus aureus (SG511, 285 and 503), Streptococcus pyogenes (A308 and A77) and Streptococcus faecium MD8b etc. The most active compound of the extract was identified to be campneoside I, which had a minimal inhibitory concentration (MIC) of 150 micrograms/ml against Streptococcus and Staphylococcus species. From such antibacterial activity, the methoxy group of campneoside I was postulated to be the essential element for the antibacterial activity.     

Four new N-contained iridoid glycosides from flower buds of Lonicera japonica

Four new N-contained iridoid glycosides, lonijapospiroside A (1), l-phenylalaninosecologanin B (2), l-phenylalaninosecologanin C (3), and dehydroprolinoylloganin A (4), were isolated from the flower buds of Lonicera japonica Thunb. Their structures were established on the basis of UV, IR, MS, and NMR spectral data.     

A phenylpropanoid glycoside with antioxidant activity from picria tel-ferae

A phytochemical study on Picria tel-ferae resulted in the isolation of a phenylpropanoid glycoside (1), which was reported for the first time from this plant. The structure of compound 1 was identified as 1-O-3,4-(dihydroxyphenyl)- ethyl-beta-D- apiofuranosyl- (1-->4)-alpha-L-rharmnopyranosyl- (1-->3)-4-O-caffeoyl- beta-D-glucopyranoside on the basis of spectroscopic analyses. In addition, it was found that 1 exhibited a remarkable inhibitory effect on lipid peroxidation initiated by either a free radical [AAPH; 2,2'-azobis-(2-amidinopropane)dihydrochloride] or generated hydroxyl radical (Fe2+/ascorbate). These findings, together with those of previous studies, suggest that P. tel-ferae possesses abundant phenylpropanoid glycosides, and the plant might be used beneficially in the treatment of oxidative stress-related human diseases.     

Anticomplement and antioxidant activities of new acetylated flavonoid glycosides from Centaurium spicatum

In addition to the three acetylated flavonol glycosides, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-beta-galactopyranoside, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3-acetyl-beta-galactopyranoside, and quercetin 3- O-[(2,3,4- triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-4-acetyl-beta-galactopyranoside, which have recently been isolated from Centaurium spicatum (L.) Fritsch (Gentianaceae), a new pentaacetylated flavonoid glycoside was isolated from the same plant. Structure elucidation, especially the localization of the acetyl groups, and complete (1)H- and (13)C-NMR assignments, was carried out using one- and two-dimensional NMR methods, including (1)H- and (13)C-NMR, DEPT-135 and DEPT-90, and gradient-assisted experiments such as DQF-COSY, TOCSY, HSQC and HMBC. The structure of the new flavonoid glycoside was established as quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3,4-diacetyl-beta-galactopyranoside. The anticomplement and antioxidant activities of these compounds were evaluated. The triacetylated flavonoid glycoside showed the highest activity in the two assays.     

Four new C10-polyacetylene glycosides from the rhizomes of Atractylodes lancea

An ongoing phytochemical investigation of the rhizomes of Atractylodes lancea resulted in the isolation of four new C₁₀-type polyacetylene glycosides (1?4). Their structures were elucidated on the basis of extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of compounds 2?4 were determined by comparing the specific rotations of their aglycones. Notably, compounds 2 and 3 exhibited significant hepatoprotective activities against APAP-induced HepG2 cell injury at a concentration of 10 μM. Compounds 2 and 3 showed weak anti-inflammatory effects on LPS-induced NO production in microglia BV2 cells at a concentration of 10 μM.     

Lignan and phenylpropanoid glycosides from Lancea tibetica and their antitumor activity.

A new lignan glucoside, the first 7,9'-monoepoxyte-trahydrofuran type lignan with the cis-relationship of H-7 and H-8, named tibeticoside (1), as well as ten known compounds have been isolated from the medicinal plant (roots, stems and leaves) Lancea tibetica. The structure of tibeticoside (1) has been elucidated on the basis of chemical and spectral evidence, especially by 2D-NMR (1H-1H COSY, HMQC, HMBC, NOESY). In addition, sylvatesmin (6) exhibited effective antitumor activity on B16 cells.     

Pharmacological activities and mechanisms of natural phenylpropanoid glycosides

The pharmacological activities and mechanisms of action of natural phenylpropanoid glycosides extracted from a variety of plants are summarized in this review, such as antitumor, antivirus, anti-inflammation, antibacteria, antiartherosclerosis, anti-platelet-aggregation, antihypertension, antifatigue, analgesia, hepatoprotection, immunosuppression, protection of sex and learning behavior, protection of neurodegeneration, reverse transformation of tumor cells, inhibition of telomerase and shortening telomere length in tumor cells, effects on enzymes and cytokines, antioxidation, free radical scavenging and fast repair of oxidative damaged DNA. Molecular modeling is discussed as well as structure-activity relationships.