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.     

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.     

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.     

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.     

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.     

Two new dihydrofuranoisoflavanones from the leaves of <Emphasis Type="Italic">Lespedeza maximowiczi</Emphasis> and their inhibitory effect on the formation of advanced glycation end products

Two new dihydrofuranoisoflavanones, 2′,4′,5-trihydroxy-[5″-(1,2-dihydroxy-1-methylethyl)-dihydrofurano(2″,3″:7,8)]-(3S)-isoflavanone (1) and 2′, 4′, 5-trihydroxy-[5″-(1,2-dihydroxy-1-methylethyl)-dihydrofurano(2″,3″:7,8)]-(3R)-isoflavanone (2) as well as one already-known compound, (+)-catechin (3), were isolated from an n-BuOH soluble fraction from the leaves of Lespedeza maximowiczi. Spectroscopic data was used to elucidate the structures of compounds 1 and 2. All of the isolates were evaluated in vitro for their inhibitory activity on the formation of advanced glycation end products (AGEs). Among these, compounds 1, 2, and 3 exhibited inhibitory activity against AGEs formation with IC₅₀ values of 20.6, 18.4, and 5.6 μM, respectively.     

A new ceramide from <Emphasis Type="Italic">Ramaria botrytis</Emphasis> (Pers.) Ricken

A new ceramide, (2S,2′R,3R,4E,8E)-N-2′-hydroxyoctadecanoyl-2-amino-9-methyl-4,8-heptadecadiene-1,3-diol (1), was isolated together with four known sterols, 5α,6α-epoxy-3β-hydroxy-(22E)-ergosta-8(14),22-dien-7-one (2), ergosterol peroxide (3), cerevisterol (4) and 9α-hydroxycerevisterol (5), from the fruiting bodies of Ramaria botrytis (Pers.) Ricken (Ramariaceae). The structure of the new compound was elucidated based on spectral data.     

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.     

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.     

(<Emphasis Type="Italic">Z</Emphasis>)-3-Hexenyl diglycosides from <Emphasis Type="Italic">Spermacoce laevis</Emphasis> Roxb.

A new (Z)-3-hexenyl O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside was isolated from the aerial part of Spermacoce laevis, along with 17 known compounds: (6S,9R)-roseoside, (Z)-3-hexenyl O-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-β-d-glucopyranoside, phenyethyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-β-d-xylopyranosyl-(1→6)-β-d-glucopyranoside, asperuloside, 6α-hydroxyadoxoside, asperulosidic acid, kaempferol 3-O-β-d-glucopyranoside, kaempferol 3-O-rutinoside, quercetin 3-O-β-d-galactopyranoside, quercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside, and rutin. The structure determinations were based on physical data and spectroscopic evidence.     

Phenolic constituents of <Emphasis Type="Italic">Acorus gramineus</Emphasis>

The purification of a MeOH extract from the rhizome of Acorus gramineus (Araceae) using column chromatography furnished two new stereoisomers of phenylpropanoid, acoraminol A (1) and acoraimol B (2). It also furnished 17 known phenolic compounds, β-asarone (3), asaraldehyde (4), isoacoramone (5), propioveratrone (6), (1′R,2′S)-1′,2′-dihydroxyasarone (7), (1′S,2′S)-1′,2′-dihydroxyasarone (8), 3′,4′-dimethoxycinnamyl alcohol (9), 3′,4′,5′-trimethoxycinnamyl alcohol (10), kaempferol 3-methyl ether (11), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol (12), hydroxytyrosol (13), tyrosol (14), (2S,5S)-diveratryl-(3R,4S)-dimethyltetrahydrofuran (15), (7S,8R)-dihydrodehydrodiconiferyl alcohol (16), 7S,8S-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (17), 7S,8R-erythro-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (18), and dihydroyashsbushiketol (19). The structures of the new compounds were elucidated by analysis of spectroscopic data including 1D and 2D NMR data. The absolute configurations of 1 and 2 were determined using the convenient Mosher ester procedure. Compounds 5–19 were isolated for the first time from this plant source. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamine B (SRB) bioassay.     

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.     

Potential anthelmintics: polyphenols from the tea plant <Emphasis Type="Italic">Camellia sinensis</Emphasis> L. are lethally toxic to <Emphasis Type="Italic">Caenorhabditis elegans</Emphasis>

A novel gallate of tannin, (−)-epigallocatechin-(2β→O→7′,4β→8′)-epicatechin-3′-O-gallate (8), together with (−)-epicatechin-3-O-gallate (4), (−)-epigallocatechin (5), (−)-epigallocatechin-3-O-gallate (6), and (+)-gallocatechin-(4α→8′)-epigallocatechin (7), were isolated from the tea plant Camellia sinensis (L.) O. Kuntze var. sinensis (cv., Yabukita). The structure of 8, including stereochemistry, was elucidated by spectroscopic methods and hydrolysis. The compounds, along with commercially available pyrogallol (1), (+)-catechin (2), and (−)-epicatechin (3), were examined for toxicity towards egg-bearing adults of Caenorhabditis elegans. The anthelmintic mebendazole (9) was used as a positive control. Neither 2 nor 3 were toxic but the other compounds were toxic in the descending order 8, 7 ≈ 6, 9, 4, 5, 1. The LC₅₀ (96 h) values of 8 and 9 were evaluated as 49 and 334 μmol L⁻¹, respectively. These data show that many green tea polyphenols may be potential anthelmintics.     

New flavonol glycosides from leaves ofSymplocarpus renifolius

A study was carried out to evaluate flavonol glycosides in leaves ofSymplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, kaempferol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-7-O-β-D-glucopyranoside, quercetin-3-O-β-D-glucopyranosy-l-(1→2)-β-D-glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses as quercetin-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-7-O-β-D-glucopyranoside, isorhamnetin-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-7-O-β-D-glucopyranoside, and quercetin-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-7-O-(6^IIII-trans-caffeoyl)-β-D-glucopyranoside.     

Inhibitory effects of compounds isolated from fruit of <Emphasis Type="Italic">Juglans mandshurica</Emphasis> on pancreatic lipase

The water extract of Juglans mandshurica fruit has been shown to strongly inhibit pancreatic lipase in vitro in a dose-dependent manner. The extract was observed to inhibit the normal elevation in the level of plasma triacylglycerol in rats 2–4 h after oral administration of a lipid emulsion. Fourteen compounds isolated from J. mandshurica fruit were evaluated for their inhibitory activity against pancreatic lipase. Of these, 1,4,8-trihydroxynaphthalene-1-O-β-d-[6′-O-(3″,4″,5″-trihydroxybenzoyl)]glucopyranoside (1) showed the strongest inhibitory activity.     

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.     

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.     

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).     

Megastigmane glucoside from <Emphasis Type="Italic">Asystasia gangetica</Emphasis> (L.) T. Anderson

A 5,11-epoxymegastigmane glucoside (asysgangoside) was isolated from the aerial parts of Asystasia gangetica together with the known compounds, salidroside, benzyl β-d-glucopyranoside, (6S,9R)-roseoside, ajugol, apigenin 7-O-β-d-glucopyranoside, apigenin 7-O-neohesperidoside, and apigenin 7-O-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside. The structure elucidations were based on spectroscopic evidence.     

Ginsenoside Rs3, a genuine dammarane-glycoside from Korean red ginseng

A genuine dammarane-glycoside, named as ginsenoside Rs₃, was isolated from the MeOH extracts of Korean red ginseng (Panax ginseng C.A. Meyer) through repeated silica gel column chromatographies and its chemical structure was determined as (20S)-protopanaxadiol 3-O-[6″-O-acetyl-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside on the basis of several spectral and physical evidences including HMBC and FAB-MS.