New isoflavone glycosides from <Emphasis Type="Italic">Iris spuria</Emphasis> L. (Calizona) cultivated in Egypt

Two new isoflavone glycosides, tectorigenin 7-O-β-d-glucopyranoside-4′-O-[β-d-glucopyranosyl-(1″″ → 6′′′)-β-d-glucopyranoside] (1) and iristectorigenin B 4′-O-[β-d-glucopyranosyl-(1′′′ → 6″)-β-d-glucopyranoside] (2), together with 11 known compounds, including six isoflavones, tectorigenin 7-O-β-d-glucopyranoside-4′-O-β-d-glucopyranoside (3), tectorigenin 4′-O-[β-d-glucopyranosyl-(1′′′ → 6″)-β-d-glucopyranoside] (4), tectorigenin 7-O-β-d-glucopyranoside (5), genistein 7-O-β-d-glucopyranoside (6), tectorigenin 4′-O-β-d-glucopyranoside (7), and tectorigenin (8); two phenolic acid glycosides, vanillic acid 4-O-β-d-glucopyranoside (9) and glucosyringic acid (10); a phenylpropanoid glycoside, E-coniferin (11); an auronol derivative, maesopsin 6-O-β-d-glucopyranoside (12); and a pyrrole derivative, 4-(2-formyl-5-hydroxymethylpyrrol-1-yl) butyric acid (13), were isolated from fresh Iris spuria (Calizona) rhizomes. The structures of these compounds were established on the basis of spectroscopic and chemical evidence. Inhibitory effects on the activation of Epstein–Barr virus early antigen were examined for compounds 1–8 and 12.     

Glycosides from whole plants of Glechoma hederacea L.

From dried whole plants of Glechoma hederacea L. (Labiatae), seven known glycosides were isolated and identified: (6R,7E,9R)-megastigma-4,7-dien-3-one 9-O-β-d-glucopyranoside (1), apigenin 7-O-neohesperidoside (2), chrysoeriol 7-O-neohesperidoside (3), (+)-pinoresinol 4,4′-bis-O-β-d-glucopyranoside (4), (+)-syringaresinol 4,4′-bis-O-β-d-glucopyranoside (5), (+)-lariciresinol 4,4′-bis-O-β-d-glucopyranoside (6), and (7R,8R)-threo-7,9,9′-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan 4-O-β-d-glucopyranoside (7).     

Constituents of the flowers of <Emphasis Type="Italic">Platycodon grandiflorum</Emphasis> with inhibitory activity on advanced glycation end products and rat lens aldose reductase <Emphasis Type="Italic">in vitro</Emphasis>

In an ongoing project directed toward the discovery of novel treatments for diabetic complications from traditional herbal medicines, fifteen compounds, apigenin (1), apigenin-7-O-β-d-glucopyranoside (2), apigenin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (3), luteolin (4), luteolin-7-O-β-d-glucopyranoside (5), luteolin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (6), isorhamnetin-3-Oneohesperidoside (7), 4-O-caffeoylquinic acid (8), chlorogenic acid methyl ester (9), 4-O-β-d-glucopyranosylcaffeic acid (10), lobetyolin (11), cordifolioidyne C (12), isomultiflorenyl acetate (13), β-sitosterol glucoside (14), and α-spinosterol (15), were isolated from an EtOAc-soluble fraction of the flowers of Platycodon grandiflorum (balloonflower; Campanulaceae). The structures of the compounds were identified by physical and spectroscopic methods, as well as by comparison of their data with literature values. All the isolates were evaluated in vitro for inhibitory activity on the formation of advanced glycation end products and rat lens aldose reductase.     

Five new glycosides from <Emphasis Type="Italic">Hypericum erectum</Emphasis> Thunb.

Five new glycosides, quercetin 3′-O-β-d-galactopyranoside (1), quercetin 3-O-(2″-acetyl)-β-d-glucopyranoside (2), 4,6-dihydroxy-2-methoxyphenyl 1-O-β-d-glucopyranoside (3), 4-hydroxy-2,6-dimethoxyphenyl 1-O-α-l-rhamnopyranosyl (1 → 6)-β-d-glucopyranoside (4) and 3-methyl-but-2-en-1-yl β-d-glucopyranosyl (1 → 6)-β-d-glucopyranoside (5), were isolated from Hypericum erectum Thunb. Their structures were established on the basis of spectral and chemical data.     

Two new neolignan glycosides from leaves of <Emphasis Type="Italic">Osmanthus heterophyllus</Emphasis>

Two new neolignan glycosides, (7R, 8R)-threo-guaiacylglycerol-8-O-4′-sinapyl ether 7-O-β-d-glucopyranoside (1) and (7S, 8R)-5-methoxydehydrodiconiferyl alcohol 4-O-β-d-glucopyranoside (2), and four known ones (3–6), were isolated from the leaves of Osmanthus heterophyllus. The structures of compounds 1–6 were established on the basis of spectral and chemical data.     

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.     

Iridoid glucoside, (3<Emphasis Type="Italic">R</Emphasis>)-oct-1-en-3-ol glycosides,and phenylethanoid from the aerial parts of <Emphasis Type="Italic">Caryopteris incana</Emphasis>

Eleven compounds of interest were isolated from the aerial parts of Caryopteris incana, specifically a new acyl derivative (3) of 8-O-acetylharpagide, two new (3R)-oct-1-en-3-ol glycosides (5, 6), and 6-O-caffeoylphlinoside A (11) along with seven known compounds, 8-O-acetylharpagide (1), 6′-O-p-coumaroyl-8-O-acetylharpagide (2), (3R)-oct-1-en-3-ol (matsutake alcohol) O-α-l-arabinopyranosyl-(1″ → 6′)-O-β-d-glucopyranoside (4), apigenin 7-O-neohesperidinoside (7), 6′-O-caffeoylarbutin (8), and two phenylethanoids, leucosceptoside A (9) and phlinoside A (10). This paper deals with structural elucidation of the new compounds.     

Four new glucosides from the aerial parts of Mediasia macrophylla

As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1′S)-(4-hydroxyphenyl) ethane-1′,2′-diol 2′-O-β-glucopyranoside (1), 3-(4′-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.     

Anticomplementary activity of stilbenes from medicinal plants

The anticomplementary activity of stilbenes from medicinal plants in Korea was investigatedin vitro. 3,5-Dihydroxy-4′-methoxystilbene (3) was most potent with IC₅₀ value of 1.5×10⁻⁴ M followed by rhapontigenin (4), oxyresverastrol (2), 2,3,4′,5-tetrahydroxystilbene-2-O-β-glucoside (9), rhaponticin (8), resverastrol (1), and piceid (7). The activity was found to be increased by a methylation on a hydroxy group of C-4′ of1, but decreased by further methylation on hydroxy groups of C-3 and C-5 and glucosylation on any hydroxy group of1. Addition of hydroxy group on C-2′ of1 or C-3′ of3 was little affected on the anticomplementary activity but the activity was increased byO-glucosylation on C-2 of1.     

Lignan and flavonoid glycosides from <Emphasis Type="Italic">Urtica laetevirens</Emphasis> Maxim.

A new compound named pinoresinol 4-O-α-l-rhamnopyranosyl (1 → 2)-β-d-glucopyranoside (1) together with six known compounds, isolariciresinol 9-O-β-D-glucopyranoside (2), apigenin 6,8-di-C-β-d-glucopyranoside (3), luteolin 7-O-neohesperidoside (4), luteolin 7-O-β-d-glucopyranoside (5), 5-methoxyluteolin 7-O-β-d-glucopyranoside (6), and rutin (7), were isolated from the aerial parts of Urtica laetevirens Maxim. All of the above compounds were isolated from this plant for the first time.     

Anti-inflammatory phenylpropanoid glycosides from <Emphasis Type="Italic">Clerodendron trichotomum</Emphasis> leaves

The chromatographic separation of MeOH extract from Clerodendron trichotomum Thunberg leaves led to the isolation of three phenylpropanoid compounds. Using spectroscopic methods, the structures of these compounds were determined as β-(3′, 4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-(4-O-caffeoyl)-glucopyranoside, acteoside (verbascoside) (1), β-(3′, 4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-(6-O-caffeoyl)-glucopyranoside, isoacteoside (2), β-(3′, 4′-dihydroxyphenyl) ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-glucopyranoside, and decaffeoylacteoside (3). We measured the anti-inflammatory activity of these three phenylpropanoid compounds both in vitro (DPPH Reduction Assay, TBARS Assay on Cu ²⁺-induced oxidized LDL, PGE₂ assay) and in vivo (acetic acidinduced vascular permeability in mice and carrageenan-induced hind paw edema in rats). 80% methanol fraction and acteoside had the activity.     

Chemical and biologically active constituents of <Emphasis Type="Italic">Pteris multifida</Emphasis>

A new compound, 4-caffeoyl quinic acid 5-O-methyl ether (2), together with 12 known compounds—identified as (2R,3R)-pterosin L 3-O-β-d-glucopyrannoside (3), β-sitosterol β-d-glucopyranoside (4), apigenin 7-Ο-β-d-glucopyranoside (5), luteolin 7-Ο-β-d-glucopyranoside (6), sucrose (7), caffeic acid (8), pterosin C 3-Ο-β-d-glucopyranoside (9), pteroside C (10), 4,5-dicaffeoyl quinic acid (11), pteroside A (12), wallichoside (13) and (2S)-5,7,3′,5′-tetrahydroxyflavanone (14)—were isolated from Pteris multifida. The structure of the new compound was determined by means of physical, chemical and spectroscopic evidence. Compounds 5 and 6 were the main constituents of the plant, with yields of 0.19% and 0.16%, respectively. The cytotoxic activities of 2, 3, and 9–13 were evaluated against a human cell line (KB cells). Among the isolated compounds, pterosin C 3-Ο-β-d-glucopyrannoside (9) and 4,5-dicaffeoylquinic acid (11) showed a significant selective cytotoxicity (IC₅₀ 2.35 and 5.38, respectively), while moderate activity was observed for compound 2 (IC₅₀ 12.3). The chemosystematics of Pteris species is also discussed.     

Prenylated flavonoid glucoside and two aliphatic alcohol glycosides from the leaves of Euodia meliaefolia (Hance) Benth.

A new prenylated flavonoid (1) and two new aliphatic glycosides (2, 3) have been isolated from leaves of Euodia meliaefolia (Hance) Benth., together with three known compounds, (2R,3R)-5,7,4′-trihydroxy-8-(3-methylbut-2-enyl)dihydroflavonol 7-O-β-d-glucopyranoside (phellamurin) (4), (2R,3R)-dihydroquercetin 3′-O-β-d-glucopyranoside (5), and (7R,8S)-dihydrodiconiferyl alcohol 4-O-β-d-glucopyranoside (6). Their structures were determined on the basis of the results of spectroscopic analysis.     

Two new phenolic glycosides from <Emphasis Type="Italic">Syringa reticulata</Emphasis>

Two new phenolic glycosides—3′-O-β-d-glucopyranosysalidroside (1) and cis-echinacoside (2)—together with four known ones—forsythoside B (3), decaffeoylacteoside (4), osmanthuside F (5) and (−)-olivil-4′-O-β-d-glucopyranoside (6)—were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of spectral and chemical 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.     

Aromatic glycosides from the flower buds of Lonicera japonica

Six new glycosides (1–6) have been isolated from the flower buds of Lonicera japonica. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as ( ? )-2-hydroxy-5-methoxybenzoic acid 2-O-β-d-(6-O-benzoyl)-glucopyranoside (1), ( ? )-4-hydroxy-3,5-dimethoxybenzoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (2), ( ? )-(E)-3,5-dimethoxyphenylpropenoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (3), ( ? )-(7S,8R)-(4-hydroxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (4), ( ? )-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (5), and ( ? )-4-hydroxy-3-methoxyphenol β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (6), respectively.     

Novel phenolic glycosides,adenophorasides A–E,from Adenophora roots

Five novel phenolic glycosides, adenophorasides A (1), B (2), C (3), D (4), and E (5), were isolated from commercial Adenophora roots, together with vanilloloside (6), 3,4-dimethoxybenzyl alcohol 7-O-β-d-glucopyranoside (7), and lobetyolin (8). The structures of the new compounds (1–5) were characterized as 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-d-glucopyranoside (1), 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (2), 4-hydroxy-3-methoxyphenylacetonitrile 4-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (3), 4-hydroxyphenylacetonitrile 4-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), and 4-hydroxy-3-methoxybenzyl alcohol 4-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (5), respectively, by means of spectroscopic and chemical analyses.     

Isolation of 3-O-(4′-Hydroxybenzyl)-β-sitosterol and 4-[4′-(4″-Hydroxybenzyloxy)benzyloxy]benzyl methyl ether from fresh tubers ofGastrodia elata

Two new 4-hydroxybenzyl alcohol derivatives (1 and2) were isolated from the methanol extract obtained from fresh tubers ofGastrodia elata together with 4-hydroxybenzyl methyl ether, 4-hydroxybenzyl alcohol, bis(4-hydroxyphenyl)methane, 4-hydroxybenzaldehyde, β-sitosterol and palmitic acid.1 and2 were identified as 3-O-(4′-hydroxybenzyl)-β-sitosterol and 4-[4′-(4″-hydroxybenzyloxy) benzyloxy)benzyl methyl ether, respectively, according to the spectroscopic data.     

Lignan and neolignan glucosides,and tachioside 2′-<Emphasis Type="Italic">O</Emphasis>-4″-<Emphasis Type="Italic">O</Emphasis>-methylgallate from the leaves of <Emphasis Type="Italic">Glochidion rubrum</Emphasis>

Thirteen compounds (1–13) were isolated from a MeOH extract of leaves of Glochidion rubrum. The structures of four new compounds were elucidated to be (−)-isolariciresinol 2a-O-β-d-glucopyranoside (1), (7R,8S)- and (7R,8R)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan 7-O-β-d-glucopyranosides (2 and 3, respectively), and tachioside 2′-O-4″-O-methylgallate (4) on detailed inspection of one- and two-dimensional NMR spectral data.     

Carboxymethyl flavonoids and a monoterpene glucoside from <Emphasis Type="Italic">Selaginella moellendorffii</Emphasis>

A new dihydroflavone, 5-carboxymethyl-7,4′-dihydroxyflavonone (1), and its glucoside 5-carboxymethyl-7,4′-dihydroxyflavonone-7-O-β-d-glucopyranoside (2), and one new monoterpene glucoside, (4Z,6E)-2,7-dimethyl-8-hydroxyocta-4,6-dienoic acid 8-O-β-d-glucopyranoside (3), were isolated from the whole plants of Selaginella moellendorffii. Their structures were determined by spectroscopic methods and chemical transformation. Compound 2 was evaluated for the ability to enhance glucose consumption in normal and insulin-resistant L6 muscle cells induced by high concentrations of insulin and glucose. Glucose consumption in insulin-resistant cells (but not in normal cells) was increased 15.2 ± 3.3% (p < 0.01) by compound 2 at a concentration of 0.1 μM in the presence of insulin (1 nM).