A new lignan glycoside from <Emphasis Type="Italic">Juniperus rigida</Emphasis>

A new lignan glycoside, named juniperigiside (1) was isolated from the CHCl₃ soluble fraction of the MeOH extract of stems and leaves of Juniperus rigida S.et Z. Compound 1 was identified by 1D- and 2D-NMR spectroscopy as well as CD analysis as (2R,3S)-2,3-dihydro-7-methoxy-2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol 4′-O-(3-O-methyl)-α-L-rhamnopyranoside. Five known lignans, icariside E4 (2), desoxypodophyllotoxin (3), savinin (4), thujastandin (5), and (−)-nortrachelogenin (6) in addition to five known labdane diterpenes including trans-communic acid (7), 13-epi-torulosal (8), 13-epi-cupressic acid (9), imbricatoric acid (10), and isocupressic acid (11) were also isolated and their structures were characterized by comparing their spectroscopic data with those in the literature. All compounds were isolated for the first time from this plant, and 5 and 6 were first reported from the genus Juniperus. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay. Compounds 3, 4, 7, and 8 showed considerable cytotoxicity against four human cancer cell lines in vitro.     

A new chromone glycoside from <Emphasis Type="Italic">Rhododendron spinuliferum</Emphasis>

A new chromone glycoside, 3,5,7-trihydroxylchromone-3-O-alpha-L-arabinopyranoside (1), together with quercetin (2), (+)-catechin (3), (-)-epi-catechin (4) were isolated from the aerial parts of Rhododendron spinuliferum. The structure of 1 was elucidated on the basis of spectroscopic and 2D-NMR spectral analysis. In addition, 1 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

A new flavonol glycoside from <Emphasis Type="Italic">Hylomecon vernalis</Emphasis>

Purification of a MeOH extract from the aerial parts of Hylomecon vernalis Maxim. (Papaveraceae) using column chromatography furnished a new acetylated flavonol glycoside (1), together with twenty known phenolic compounds (2–21). Structural elucidation of 1 was based on 1D- and 2D-NMR spectroscopy data analysis to be quercetin 3-O-[4‴-O-acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β-D-galactopyranoside (1). The structures of compounds 2–21 were elucidated by spectroscopy and confirmed by comparison with reported data; quercetin 3-O-[2‴-O-acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β -D-galactopyranoside (2), quercetin 3-O-α-L-arabinopyranosyl-(1‴→6″)-β-D-galactopyranoside (3), quercetin 3-O-β -D-galactopyranoside (4), kaempferol 3,7-O-α-L-dirhamnopyranoside (5), diosmetin 7-O-β -D-glucopyranoside (6), diosmetin 7-O-β -D-xylopyranosyl-(1‴→6″)-β-D-glucopyranoside (7), p-hydroxybenzoic acid (8), protocatechuic acid (9), caffeic acid (10), 6-hydroxy-3,4-dihydro-1-oxo-β -carboline (11), (Z)-3-hexenyl-β -D-glucopyranoside (12), (E)-2-hexenyl-β -D-glucopyranoside (13), (Z)-3-hexenyl-α-Larabinopyranosyl-(1″→6′)-β-D-glucopyranoside (14), oct-1-en-3-yl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (15), benzyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside (16), benzyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (17), benzyl-β-D-xylopyranosyl-(1″→6′)-β-Dglucopyranoside (18), 2-phenylethyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (19), 2-phenylethyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside (20), and aryl-β-D-glucopyranoside (21). Compounds 2-21 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.     

One new pregnane glycoside from the seeds of cultivated <Emphasis Type="Italic">Brucea javanica</Emphasis>

A new pregnane glycoside, named (20R)-O-(3)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol (1), and seven known compounds, brusatol (2), bruceine B (3), bruceine D (4), yadanziolide A (5), bruceine E (6), yadanzioside G (7), and yadanzioside B (8), were isolated from the cultivated dry seeds of Brucea javanica. The structure of 1 was elucidated on the basis of 1D- and 2D-NMR spectroscopic analyses. Their inhibitory effects on tumor cells were also tested. Compound 1 was slightly active against HL-60, SMMC-7721, A-549, and MCF-7 tumor cells. Compounds 2 and 3 demonstrated significant inhibitory activities against all tested cells. These results indicate that cultivated B. javanica could replace the wild plant as an antitumor plant resource.     

A new <Emphasis Type="Italic">ent</Emphasis>-kaurane type diterpenoid glycoside from <Emphasis Type="Italic">Inula japonica</Emphasis> Thunb.

A new ent-kaurane type diterpenoid glycoside, 17-O-β-D-glucopyranosyl-16α-ent-kauran-19-oic acid (1), together with 17-hydroxy-16α-ent-kauran-19-oic acid (2), 16α,17-dihydroxyl-ent-kauran-19-oic acid (3), and 16α-hydroxy-17-acetoxy-ent-kauran-19-oic acid (4) were isolated from the aerial parts of Inula japonica Thunb. The structure of 1 was determined mainly by use of 1D and 2D NMR spectroscopic techniques including HSQC, ¹H-¹H COSY, HMBC, and NOESY. In addition, 4 exhibited significant inhibitory activity on NO production in LPS-stimulated RAW264.7 cells with IC₅₀ value of 14.3 μg/mL.     

A new <Emphasis Type="Italic">Erythrina</Emphasis> alkaloid from <Emphasis Type="Italic">Erythrina herbacea</Emphasis>

A new Erythrina alkaloid, 10-hydroxy-11-oxoerysotrine (1), has been isolated from the flowers of Erythrina herbacea together with five known compounds: erytharbine (2), 10,11-dioxoerysotrine (3), erythrartine (4), erysotramidine (5) and erysotrine-N-oxide (6). The structure of the new compound was elucidated on the basis of its spectral data, including 2-D NMR and mass (MS) spectra. The new compound is a rare C-10 oxygenated Erythrina alkaloid. The antioxidant activities of the isolated compounds 1–6 were evaluated by scavenging with peroxynitrite.     

A new triterpene glycoside from the stems of <Emphasis Type="Italic">Lagerstroemia indica</Emphasis>

A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2–10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1–10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC₅₀ values ranging from 3.38 to 6.29 μM.     

A new phenylpropane glycoside from the rhizome of <Emphasis Type="Italic">Sparganium stoloniferum</Emphasis>

The purification of the MeOH extract from the rhizome of Sparganium stoloniferum Buch.-Hamil. (Sparganiaceae) using column chromatography furnished one new phenylpropanoid glycoside (7) and known phenolic compounds (1–6, and 8–13). The structural elucidation of 7 was based on 1D- and 2D-NMR spectroscopic data analysis to be β-d-(6-O-trans-feruloyl) fructofuranosyl-α-d-O-glucopyranoside. Compounds 1–6, and 8–13 were elucidated by spectroscopy and confirmed by comparison with reported data; 24-methylenecycloartanol (1), p-hydroxybenzaldehyde (2), ferulic acid (3), p-coumaric acid (4), vanillic acid (5), β-d-(1-O-acetyl-3-O-trans-feruloyl)fructofuranosy-α-d-2′,4′,6′.-O-triacetyglucopyranoisde (6), β-d-(1-O-acetyl-3,6-O-trans-diferuloyl)fructofuranosyl-β-d-2′,4′,6′.-O-triacetylglucopyranoisde (8), hydroxytyrosol acetate (9), hydroxytyrosol (10), isorhamnetin-3-O-rutinoside (11), n-butyl-α-d-fructofuranoside (12), and n-butyl-β-d-fructopyranoside (13). Compounds 3 and 9–13 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.     

A new acylphloroglucinol glycoside from <Emphasis Type="Italic">Solidago altissima</Emphasis> L.

A new acylphloroglucinol glycoside was isolated from the leaves of Solidago altissima L. The chemical structure of the glycoside, which has a phloroglucinol moiety with a butyryl side chain, was elucidated based on the analysis of spectroscopic data.     

A new phenolic glycoside syringate from the bark of <Emphasis Type="Italic">Juglans mandshurica</Emphasis> MAXIM. var. <Emphasis Type="Italic">sieboldiana</Emphasis> MAKINO

A new phenolic glycoside syringate, 4′-hydroxy-2′,6′-dimethoxyphenol 1-O-β-d-(6-O-syringoyl) glucopyranoside (1), together with two known ones, 2′-hydroxy-4′-methoxyphenol 1-O-β-d-(6-O-syringoyl) glucopyranoside (2) and 4′-hydroxy-2′-methoxyphenol 1-O-β-d-(6-O-syringoyl) glucopyranoside (3), were isolated from the bark of Juglans mandshurica MAXIM. var. sieboldiana MAKINO. Their structures were established on the basis of spectral and chemical data.     

A new isoflavone glycoside from the stem bark of <Emphasis Type="Italic">Sophora japonica</Emphasis>

A new isoflavone glycoside, 6-methoxy-7-hydroxy-4′-O-β-d-glucosyl isoflavone, glycitein-4′-O-β-d-glucoside (10), along with nine known flavonoids, were isolated from the stem bark of Sophora japonica. The structures of these compounds were determined by analysis of spectroscopic data (1D -, 2D - NMR and HRMS). The inhibitory effects of all the isolated compounds on aldose reductase were evaluated in vitro. Among these compounds, daidzein (1), puerol A (4), and paratensein-7-O-glucoside (9) exhibited potent inhibitory effects, with IC₅₀ values of 3.2, 6.4, and 1.9 μM, respectively.     

Antiplasmodial indole alkaloids from <Emphasis Type="Italic">Leuconotis griffithii</Emphasis>

A new indole alkaloid, leucoridine A N-oxide (1), consisting of two units of a strychnan type of skeleton, was isolated from the leaves of Leuconotis griffithii. Its structure was elucidated by various spectroscopic means such as NMR and MS, and also by chemical means. Antiplasmodial activity against Plasmodium falciparum 3D7 of indole alkaloids isolated from L. griffithii was investigated.     

<Emphasis Type="Italic">ent</Emphasis>-Abietane diterpenoids from <Emphasis Type="Italic">Isodon xerophilus</Emphasis>

Three new ent-abietanoids, named xerophilusins XIV–XVI, and four known analogues, as well as four known chemical constituents were isolated from the leaves of Isodon xerophilus. Their structures were elucidated by extensive spectroscopic studies, and comparison with literature data. In addition, the cytotoxic activity of the ent-abietanoids against chronic myelogenous leukemia (K562), stomach adenocarcinoma (MKN45), and hepatocellular carcinoma (HepG2) human cell lines was investigated and no activities were observed.     

A new lignan glycoside from the fruits of <Emphasis Type="Italic">Cornus kousa</Emphasis> Burg.

A new lignan glycoside, (7'S, 8'R)-dihydrodehydrodiconiferyl alcohol-4'-O-beta-D-xylopyranoside (1), named cornuskoside A, was isolated from the fruits of Cornus kousa. The structure of the compound was determined by spectroscopy, including FABMS, UV, IR, (1)H-and 13C-NMR, DEPT and 2D-NMR (COSY, HSQC, and HMBC). This new lignan glycoside, along with its aglycone, (7'S, 8'R)-dihydrodehydrodiconiferyl alcohol (3), and another lignan with a similar skeleton, (-)-balanophonin (2), which have been previously isolated from this plant, were evaluated for cytotoxicity in human cancer cell lines such as HeLa, MCF-7, SK-MEL-5, and SK-OV-3. Compounds 2 and 3 showed cytotoxicity against HeLa [IC50 = 29.1 microM (2), 45.5 microM (3)], MCF-7 [IC50 = 29.2 microM (2), 28.2 microM (3)], SK-MEL-5 [IC50 = 31.3 microM (2), 32.3 microM (3)], and SK-OV-3 [IC50 = 33.4 microM (2), 43.4 microM (3)] cell lines.     

Two new antibacterial norabietane diterpenoids from cyanobacteria, <Emphasis Type="Italic">Microcoleous </Emphasis><Emphasis Type="Italic">lacustris</Emphasis>

Two abietane diterpenes were isolated from cyanobacteria Microcoleous lacustris, 20-nor-3α-acetoxyabieta-5,7,9,11,13-pentaene and 20-nor-3α-acetoxy-12-hydroxy-abieta-5,7,9,11,13-pentaene. These compounds were assayed against Staphylococcus aureus, Staphylococcus epidermidis, Salmonella typhi, Vibrio cholerae, Bacillus subtilis, Bacillus cereus, Escherichia coli, and Klebsiella pneumoniae. Both compounds showed activity against S. aureus, S. epidermidis, S. typhi, and V. cholerae, but not against the other bacteria.     

A new lignan from <Emphasis Type="Italic">Aphanamixis polystachya</Emphasis>

A new lignan, polystachyol (1), two lignan glycosides, lyoniside (2) and nudiposide (3), and a sterol, ergosta-4,6,8(14),22-tetraen-3-one (4), with stigmasterol, and oleic and linoleic acids, have been isolated from an MeOH extract of the dried bark of Aphanamixis polystachya. The structures of the isolated compounds were elucidated by analysis of 1D and 2D NMR and mass spectroscopic data. The compounds did not have growth inhibitory activity against HeLa cells.     

Three new <Emphasis Type="Italic">C</Emphasis>-glycosyflavones with acetyl substitutions from <Emphasis Type="Italic">Swertia mileensis</Emphasis>

Three new acetylated C-glycosylflavones, 3″,6″-di-O-acetylswertiajaponin (1), 4″,6″-di-O-acetylswertiajaponin (2), and 6″-O-acetylswertiajaponin (3), together with six known compounds were isolated from the whole herb of Swertia mileensis. Their structures were elucidated on extensive NMR experiments and mass spectrometry studies. ¹H and ¹³C NMR data exhibited doublet signals at room temperature. Variable temperature ¹H NMR experiments were carried out to investigate the presence of rotational isomerism of C-glycosylflavones. All compounds showed potential antioxidant activities against apoptosis of H₂O₂-induced human embryo liver L02 cells.     

<Emphasis Type="Italic">In Vitro</Emphasis> hepatoprotective compounds from <Emphasis Type="Italic">Suaeda glauca</Emphasis>

Bioassay-guided fractionation of the MeOH extract of Suaeda glauca yielded four phenolic compounds, methyl 3,5-di-O-caffeoyl quinate (1) and 3,5-di-O-caffeoyl quinic acid (2), isorhamnetin 3-O-beta-D-galactoside (3), and quercetin 3-O-beta-D-galactoside (4). Compounds 1 and 2 were hepatoprotective against tacrine-induced cytotoxicity in human liver-derived Hep G2 cells with the EC(50) values of 72.7+/-6.2 and 117.2+/-10.5 microM, respectively. Silybin as a positive control showed an EC(50) value of 82.4+/-4.1 microM.     

A new triterpenoid from <Emphasis Type="Italic">Brucea javanica</Emphasis>

A new triterpenoid, bruceajavanin C (1), together with bruceosides A and B (2 and 3), bruceines D and E (4 and 5), yadanziosides A and G (6 and 7), (20R)-O-(3)-α-L-arabinopyranosylpregn-5-ene-3β,20-diol (8), and α-D-glucopyranoside, (3β, 20R)-3-hydroxypregn-5-en-20-yl (9) were isolated from the aerial parts of Brucea javanica. The structure of 1 was elucidated on the basis of 2D-NMR spectroscopic analysis. In addition, compounds 1, 3, 4, 5, and 6 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

A new sesquiterpene from <Emphasis Type="Italic">Artemisia vulgaris</Emphasis>

The dichloromethane extract of the air-dried leaves of Artemisia vulgaris afforded a new sesquiterpene 1, caryophyllene oxide, phytyl fatty acid esters, squalene, stigmasterol and sitosterol. The structure of 1 was elucidated by extensive one- and two-dimensional nuclear magnetic resonance spectroscopy.