Isolation and characterization of a new flavone diglucoside from <Emphasis Type="Italic">Salix denticulata</Emphasis>

A new flavone diglucoside named 7,3′-dihydroxy-4′-methoxyflavone-5-O-β-D-glucopyranosyl (6″ → 1‴)-β-D-glucopyranoside (1), along with four known flavonoids, luteolin (2), isoquercetin (3), catechin (4), and diosmetin (5), has been isolated and characterized from Salix denticulata. The structure of the new flavone diglucoside was characterized by means of high field 1D and 2D NMR and MS spectral analysis.     

A new furostanol glycoside with fatty acid synthase inhibitory activity from <Emphasis Type="Italic">Ophiopogon japonicusa</Emphasis>

A new furostanol glycoside, named ophiopogonin J (1), was isolated from the fibrous root of Ophiopogon japonicas. The structure of the compound was established as (25R)-26-[(O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl)]-20α -hydroxyfurost-5, 22-diene-3-O-α-L-rhamnopyranosyl-(1 → 2)-[β-D-xylopyranosyl(1 → 4)]-β-D-glucopyranoside on the basis of spectroscopic methods, including HR-ESI-MS and 1D and 2D NMR experiments.     

A novel compound from <Emphasis Type="Italic">Flos carthami</Emphasis> and its bioactivity

A novel compound, 4-{1′-hydroxy-1′-mercapto-1′-[1′′-2′′(N→O)-isoquinolyl]}yl-1-benzoic acid (1), together with six known compounds, 6-hydroxykaempferol-3-O-β-D-glucopyranoside (2), rutin (3), quercetin-3-O-β-D-glucopyranoside (4), kaempferol-3-O-β-D-glucopyranoside (5), cartormin (6), hydroxysafflor yellow A (7), were isolated by chromatography from the n-BuOH fraction of 50% ethanol extraction of Flos carthami. Their structures were elucidated on the basis of spectral analysis and comparison with published data. Among them, compound 1 was shown to possess a weak protective effect against cerebral ischemic damage in rats. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 339–341, May–June, 2009.     

Isoflavone glycosides from the bark of Amorpha fruticosa

Four known isoflavone glucosides have been isolated from the bark of Amorpha fruticosa, which is a traditional remedy plant, for the first time. They were elucidated as 3′-hydroxy-4′-methoxyisoflavone-7-O-β-D-glucopyranoside (1), 4′,6-dimethoxyisoflavone-7-O-β-D-glucopyranoside (2), 4′-methoxyisoflavone-7-O-β-D-glucopyranoside (3), and 3′,5-dihydroxy-4′-methoxyisoflavone-7-O-β-D-glucopyranoside (4), based on the UV, FT-IR, EIMS, FABMS, HREIMS, and NMR (¹H and ¹³C, DEPT, COSY, NOESY, HMQC, and HMBC) data. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 336–338, July–August, 2006.     

Ellagic acid derivatives from the stem bark of <Emphasis Type="Italic">Dipentodon sinicus</Emphasis>

Ellagic acid derivatives were isolated from Dipentodon sinicus and their structures were identified as 3,3′,4′-tri-O-methylellagic acid (1), 3,3′-di-O-methylellagic acid (2), 4,4′-di-O-methylellagic acid (3), 3,3′-di-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (4), 3,3′,4′-tri-O-methylellagic acid-4′-O-β-D-glucopyranoside (5), 3,3′-di-O-methylellagic acid-4′-O-β-D-glucopyranoside (6), and ellagic acid (7). All the compounds were isolated for the first time from the title plant. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 106–107, March–April, 2007.     

A new flavonol derivative from <Emphasis Type="Italic">Fagopyrum dibotrys</Emphasis>

A new flavonol derivative 3, 8-dihydroxy-10-methoxy-5-H-isochromeno[4, 3-b]chromen-7-one (1) together with four known compounds, glutinone (2), luteolin (3), acacetin 7-O-α-L-rhamnopyranosyl- (1→6)-β-D-glucopyranoside (4), and rutin (5) were isolated from the dried roots of Fagopyrum dibotrys. Their structures were determined by UV, IR, MS, ¹H, and ¹³C NMR spectroscopic analysis, including 2D NMR. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 567–568, November–December, 2008.     

A new carbamic acid from Dryopteris wallichiana

A new carbamic acid, (1,7a-dihydro-1H-inden-2(7aH)-ylidene)methylcarbamic acid (1), along with three known ones, 12-ursen-28-oic acid-3-O-β-D-glucopyranoside (2), 12-ursen-3-O-β-D-glucopyranoside (3), and 3,7,11,15-tetramethyl-2-hexadecen-1-ol (4), was isolated and identified from Dryopteris wallichiana.     

New glycosidic and other constituents from hulls of <Emphasis Type="Italic">Oryza sativa</Emphasis>

Three new compounds, 4-hydroxymethylene-7-(9,9,13-trimethylcyclohexyl)-heptanyl-3′,7′,7′-trimethylcyclohexa-2′,4′-dien-1′-oate (1), 1-(n-hexadec-7-enoxy)-6-(n-octadecanoxy)-β-D-glucopyranoside (2), and (Z)-12-hydroxy-9-octadecenoic acid-12-β-D-glucopyranoside (3), along with the known compound hexacosanoic acid (4), were isolated and identified from the rice hulls of Oryza sativa. Their structures were elucidated by 1D and 2D NMR spectroscopic techniques (¹H-¹H COSY, ¹H-¹³C HETCOR, DEPT) aided by EIMS, FABMS, HRFABMS, and IR spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 344–347, July–August, 2007.     

A new cerebrogalactoside from <Emphasis Type="Italic">Juglans mandshurica</Emphasis>

A new cerebrogalactoside, Juglans cerebroside A (1), together with five known compounds, quercetin-3-O-β-D-galactopyranoside (2), myricetin-3-O-β-D-galactopyranoside (3), 2″E-quercetin-3-O-β-D-(6″″-O-[3″(4′″-hydroxyphenyl) propylene acyl]) glucopyranoside (4), gallic acid (5), and 2-methyl-1-hexadecanol (6) were isolated from the leaves of Juglans mandshurica Maxim. The structures of these compounds were determined by 1D, 2D NMR, and MS techniques.     

A new flavonoid glycoside from <Emphasis Type="Italic">Galium verum</Emphasis>

A new flavonoid glycoside, an apigenin 7-O-(3,4-di-O-acetyl)-α-L-rhamnopyranosyl-(1 → _6)-β-D- glucopyranoside (1), was isolated from the 95% ethanol extract of Galium verum L. Its structure was elucidated by spectroscopic analysis.     

A new stilbene glycoside from the <Emphasis Type="Italic">n</Emphasis>-butanol fraction of <Emphasis Type="Italic">Veratrum dahuricum</Emphasis>

A new stilbene glycoside, 5-methylresveratrol-3,4′-O-β-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-β-D-glycoside (2), 4′-methylresveratrol-3-O-β-D-glycoside (3), oxyresveratrol-4′-O-β-D-glycoside (4), oxyresveratrol-3-O-β-D-glycoside (5), and oxyresveratrol-3,4′-O-β-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of 1D and 2D NMR data. Compounds 1–6 showed platelet aggregation inhibition, and compound 1 had an IC₅₀ value of 383.6 μM against platelet aggregation induced by AA. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 279–282, May–June, 2009.     

Flavonol glycosides of <Emphasis Type="Italic">Pseudodrynaria coronans</Emphasis> and their antioxidant activity

A new flavonol glycoside and four known flavonol glycosides were isolated from the whole plant of Pseudodrynaria coronans. By means of spectroscopic analysis, their structures were established as kaempferol3-O-(6' -O-feruloyl-4' -O-acetyl)-β-D-glucopyranoside (1), kaempferol-3-O-(6' -O-feruloyl)-β-Dglucopyranoside (2), kaempferol-3-O-(6' -O-acetyl)-β-D-glucopyranoside (3), astragalin (4), and isoquercitrin (5). The DPPH radical scavenging activities of these compounds were also assayed.     

Acylated flavonol glycosides from Sedum aizoon

A new acylated flavonol glycoside (1) and a known compound (2) have been isolated from the whole plant of Sedum aizoon L. Their structures have been established as quercetin 3-O-[β-D-(2‴-O-(E)-feruloyl)-xylopyranosyl]-(1 → 6)-β-D-glucopyranoside (1) and rutin (2) by means of spectroscopic analysis and chemical methods.     

Ellagic acid glycosides from the stem bark of <Emphasis Type="Italic">Aphananthe aspera</Emphasis>

Five ellagic acid glycosides were isolated from Aphananthe aspera and their structures were identified as 3-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (1), 3-O-methylellagic acid-4′-O-β-D-xylopyranoside (2), 3,3′-di-O-methylellagic acid-4′-O-β-D-xylopyranoside (3), 3,3′, 4-tri-O-methylellagic acid-4′-O-β-D-glucopyranoside (4), and 3,3′-di-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (5) on the basis of spectroscopic analysis. Compound 1 is new, and all the compounds were isolated for the first time from the title plant. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 458–459, September–October, 2007.     

A new flavone glycoside from the aerial part of <Emphasis Type="Italic">Scutellaria schachristanica</Emphasis>

The new flavone glycoside schachristanoside was isolated from the aerial part of Scutellaria schachristanica Zuz. (Lamiaceae). Spectral data and chemical transformations found that schachristanoside had the structure chrysin-7-O-[α-L-arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside.     

Flavonoid oligosides from georgian <Emphasis Type="Italic">Astragalus falcatus</Emphasis>

New flavonoid oligosides were isolated from leaves and flowers of Astragalus falcatus Lam. It was found on the basis of chemical transformations, UV, IR, PMR, ¹³ C NMR, HMBC, HSQC, 1D-TOCSY, and mass spectral properties that falcoside C had the structure quercetin 3-O-[β-D-glucopyranosyl(1 → 3)-α-Lrhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-β-D-glucopyranoside; falcoside D, isorhamnetin 3-O-[β-D-xylopyranosyl(1 → 3)-α-L-rhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-α-Lrhamnopyranoside.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. XC. Askendoside K from <Emphasis Type="Italic">Astragalus taschkendicus</Emphasis>

A new triterpene cycloartane glycoside called askendoside K was isolated from roots of Astragalus taschkendicus Bunge (Leguminosae). The structure of this glycoside was established using chemical and biochemical transformations and spectral data. Askendoside K was a bisdesmoside of cycloorbigenin C and had the structure 23R,24R-cycloartan-3β,6α,16β,23,24,25-hexaol 3-O-[(α-L-arabinopyranosyl)(1 → 2)-β-D-xylopyranoside],23-O-[(β-D-glucuronopyranosyl)(1 → 2)-β-D-glucopyranoside].     

A novel kaempferol triglycoside from flower buds of <Emphasis Type="Italic">Panax quinquefolium</Emphasis>

Three kaempferol glycosides were isolated from the flower buds of Panax quinquefolium L. together with kaempferol (1). By means of chemical and spectroscopic methods (NMR, ESI-MS, 2D NMR), their structures were established as trifolin (2), panasenoside (3), and kaempferol-3-O-β-D-glucosyl(1→2)-β-D-galactoside-7-O-α-L-rhamnoside (4).Compound 4 is a new compound.     

Phenolic constituents from the stems of <Emphasis Type="Italic">Acanthopanax senticosus</Emphasis>

A new phenolic glycoside was isolated from the stems of Acanthopanax senticosus together with sixteen known compounds. The structure of the new compound was determined to be 2,6-dimethoxy-4-[(1E)-3,3-dimethoxy-1-propenyl]phenyl β-D-glucopyranoside (1) by means of physical, chemical, and spectroscopic methods. Of the known compounds, salvadoraside (7), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4,9′-di-O-β-D-glucopyranoside (8), 3-(4-O-β-D-glucopyranosylferuloyl)quinic acid (15), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (16), and lycoperodine-l (17) were first reported from the title plant. The inhibitory activities of the isolated compounds against α-glucosidase from rat intestine were also reported.     

Two new myricetin glycosides from pine needles of <Emphasis Type="Italic">Cedrus deodara</Emphasis>

Two new myricetin glycosides, myricetin-3-O-(6″-O-E-p-coumaroyl)-α-D-glucocopyranoside (1) and 3′,5′-di-O-methylmyricetin-3-O-(6″-O-acetyl)-α-D-glucopyranoside (2), and three known flavonoids, myricetin (3), cedrin (4), and 2R,3R-dihydromyricetin (5), were isolated from the pine needles of Cedrus deodara. Their structures were elucidated on the basis of extensive spectroscopic analysis and chemical evidence.