Aromatic compounds and triterpenoidal saponins fromClematis koreana var.umbrosa

From the methanolic extract of aerial parts ofClematis koreana var.umbrosa, one new triterpenoidal saponin, 3-O-β-D-xylopyranosyl(1–3)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl(1–4)-β-D-glucopyranosyl(1–6)-β-D-glucopyranosyl ester, along with five known aromatic compounds and two known triterpenoidal saponins were isolated.     

New triterpenoid saponins from <Emphasis Type="Italic">Argania spinosa</Emphasis>

Five new triterpene saponins, arganine L (1), O (2), P (3), Q (4) and R (5), were isolated from the barks of Argania spinosa (L.) Skeels. Arganines L-P and R are bidesmosidic saponins. The structures of 1–5 were elucidated as 3-O-[β-d-xylopyranosyl-(1–4)-β-d-glucuronopyranosyl]-28-O-[β-d-apiofuranosyl-(1–3)-β-d-xylopyranosyl-(1–4)-α-l-rhamnopyranosyl-(1–2)-α-l-arabinopyranosyl] bayogenin, 3-O-[β-d-xylopyranosyl-(1–4)-β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1–4)-α-l-arabinopyranosyl] bayogenin, 3-O-[β-d-xylopyranosyl-(1–4)-β-d-glucuronopyranosyl]-28-O-[α-l-arabinopyranosyl] bayogenin, 3-O-[β-d-xylopyranosyl-(1–4)-β-d-glucuronopyranosyl] bayogenin, and 3-O-[β-d-apiofuranosyl-(1–4)-β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1–4)-α-l-rhamnopyranosyl-(1–2)-α-l-arabinopyranosyl] bayogenin, respectively, mainly on the basis of their spectroscopic data.     

Isolation and identification of chondroitin sulfates from the mud snail

Chondroitin sulfates were isolated from the mud snail. For the quantitative analysis of enzymatic digestion products of isolated chondroitin sulfates, strong anion exchange-high performance liquid chromatography (SAX-HPLC) was performed. By the action of chondroitinase ABC, three unsaturated disaccharides 2-acetamide-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-D-galactose (ΔDi-OS), 2-acetamide-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-6-O-sulfo-D-galactose (ΔDi-6S) and 2-acetamide-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose (ΔDi-4S) were produced from the mud snail chondroitin sulfates. The analysis showed that relative proportion of ΔDi-OS/ΔDi-6S/ΔDi-4S was 58.7/3.1/38.2. The immunomodulating activity of chondroitin sulfate was examined by cell proliferation assay and these results suggest that it might be a immunosuppressant.     

Lignan glycosides from the leaves of <Emphasis Type="Italic">Osmanthus heterophyllus</Emphasis>

Seven known lignan glycosides were isolated from the leaves of Osmanthus heterophyllus: (+)-syringaresinol 4-O-β-d-glucopyranoside, (+)-syringaresinol 4, 4′-O-di-β-d-glucopyranoside, (+)-medioresinol 4, 4′-O-di-β-d-glucopyranoside, (+)-medioresinol 4-O-β-d-glucopyranoside, (+)-pinoresinol 4, 4′-O-β-d-glucopyranoside, (+)-epipinoresinol 4-O-β-d-glucopyranoside and phillyrin. Their structures were determined on the basis of 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.     

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.     

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.     

Lignan glycosides and flavonoids from <Emphasis Type="Italic">Saraca asoca</Emphasis> with antioxidant activity

Five lignan glycosides, lyoniside, nudiposide, 5-methoxy-9-β-xylopyranosyl-(−)-isolariciresinol, icariside E₃, and schizandriside, and three flavonoids, (−)-epicatechin, epiafzelechin-(4β→8)-epicatechin and procyanidin B₂, together with β-sitosterol glucoside, were isolated from a methyl alcohol (MeOH) extract of Saraca asoca dried bark. Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) and mass spectroscopic analysis. Antioxidant activities were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay.     

Chemical constituents of the Thai medicinal plant, <Emphasis Type="Italic">Dioecrescis erythroclada</Emphasis> (Kurz) Tirveng

Six compounds were isolated from the leaves and branches of Dioecrescis erythroclada and identified as apodanthoside, mussaenoside, gardenoside, benzyl alcohol O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside, phenethyl alcohol O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside, and oct-1-en-3-ol α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside. The structures were determined based on physical data and spectroscopic evidence.     

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.     

Saponins from the fructus ofKochia scoparia

Two new triterpenoidal saponins,B(1) andC(2) were isolated from the fruccus ofKochia scoparia. On the basis of chemico-spectral evidences, the structures of1 and2 were elucidated as oleanolic acid 3-O-β-D-ribopyranosyl-(1→2)-β-D-glucuronopyranoside and 3-O-β-D-xylopyranosyl-(1→3)-β-D-glucuronopyranosyl-olean-12-en-28-O-β-D-glucopyranosyl ester, respectively.     

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.     

Two new secoiridoid glycosides from the rhizomes of Gentiana scabra Bunge

Two new secoiridoid glycosides, 4‴-O-β-D-glucopyranosyltrifloroside 1 and 4‴-O-β-D-glucopyranosylscabraside 2, along with three known secoiridoids were isolated from the rhizomes of Gentiana scabra (Gentianaceae) in our recent phytochemical study. Their chemical structures were determined by spectroscopic data including 1D and 2D NMR spectra. The chemotaxonomic significance of the secoiridoid glycosides is briefly discussed.     

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.     

A new phenolic glucoside from an Uzbek medicinal plant, Origanum tyttanthum

A new phenolic glucoside was isolated from the aerial parts of Origanum tyttanthum, an Uzbek medicinal plant, together with 12 known compounds. The structure of the new compound was elucidated as 4-O-β-d-glucopyranosylbenzyl-3′-hydroxyl-4′-methoxybenzoate (1) based on the spectral and chemical evidence.     

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.     

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.     

(<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.     

Constituents of the leaves and roots of Ligularia stenocephala MATSUM. et KOIDZ.

Constituents of the leaves and roots of Ligularia stenocephala MATSUM. et KOIDZ. (Compositae) were investigated. Three compounds, (2E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-ol, (3E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyl-3,6,10,14,18,22-tetracosahexaen-2-ol and neophytadiene, were isolated from the leaves of L. stenocephala. Six compounds, 5-acetyl-6-hydroxy-2α-isopropenyl-3β-methoxy-2,3H-benzofuran, 3β-acetoxy-6-acetyl-5-hydroxy-2α-isopropenyl-2,3H-benzofuran, p-hydroxybenzaldehyde, vanillin, 4-hydroxyacetophenone and 4-hydroxy-3-methoxyacetophenone, were isolated from the roots of L. stenocephala. The structures were determined on the basis of spectral 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).