(<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.     

New triterpene saponins from <Emphasis Type="Italic">Stenocereus eruca</Emphasis> (Cactaceae)

Two new triterpene saponins, named stellatoside B (1) and erucasaponin A (2), were isolated from a cactaceous plant, Stenocereus eruca A. C. Gibson & K. E. Horak (Machaerocereus eruca Br. & R.). The structures of 1 and 2 were elucidated as 3-O-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranosyl stellatogenin and 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→3)]-β-d-glucuronopyranosyl betulinic acid 28-O-α-l-rhamnopyranosyl ester, respectively, on the basis of their spectroscopic data.     

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.     

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.     

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.     

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.     

Monoterpene glycoside and flavonoids from <Emphasis Type="Italic">Blumea lacera</Emphasis>

The dichloromethane extract of air-dried leaves of Blumea lacera (Asteraceae) afforded α-pinene-7β-O-β-d-2,6-diacetylglucopyranoside (1), 5,4′-dihydroxy-6,7,3′-trimethoxyflavone (2), and 3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone (3). Compounds 1–3 showed moderate activity against Candida albicans, low activity against Trichophyton mentagrophytes, and were inactive against Aspergillus niger. Compounds 1 and 3 indicated low activity against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus and were inactive against Bacillus subtilis, while 2 was inactive against all four bacteria tested.     

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.     

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 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.     

Chromone and flavonol glycosides from <Emphasis Type="Italic">Delphinium hybridum</Emphasis> cv. “Belladonna Casablanca”

One new chromone and six known flavonol glycosides were isolated from the stems and leaves of Delphinium hybridum cv. “Belladonna Casablanca” (Ranunculaceae). The new chromone glycoside was elucidated as 2-methyl-chromone-5,7-diol 7-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (1). The six known flavonol glycosides were designated as compounds 2–5, being kaempferol-type glycosides, and compounds 6 and 7, being quercetin-type glycosides. The structures of these glycosides were determined by two-dimensional nuclear magnetic resonance (2D NMR) spectroscopic analysis and chemical evidence.     

Prenylated xanthones from <Emphasis Type="Italic">Hypericum ascyron</Emphasis>

Three new prenylated xanthones, 1,3,5-trihydroxy-6,7-[2′-(1-methylethenyl)-dihydrofurano]-xanthone (1), 1,3,5-trihydroxy-6,7-[2′-(1-hydroxy-1-methylethyl)-dihydrofurano]-xanthone (2), and 1,3,5-trihydroxy-6-O-prenyl-xanthone (3), together with eight known compounds were isolated from the leaves of Hypericum ascyron. Compound 3 has an O-prenyl moiety, and therefore represents the first reported xanthone to have an O-prenyl moiety from genus Hypericum. The structures of the isolated compounds were established based on spectroscopic data and on a comparison with values for previously identified analogues.     

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.     

Two new triterpenoid saponins from rhizome of <Emphasis Type="Italic">Anemone raddeana</Emphasis> Regel

Two new 27-hydroxyoleanolic acid-type triterpenoid saponins, raddeanoside Ra (1) and raddeanoside Rb (2), were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated to be 27-hydroxyoleanolic acid 3-O-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranoside (1) and 27-hydroxyoleanolic acid 3-O-α-l-arabinopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α- l-arabinopyranoside (2) on the basis of chemical and spectral evidence.     

Flavonol glycosides from the aerial parts of<Emphasis Type="Italic">Aceriphyllum rossii</Emphasis> and their antioxidant activities

The methanol extract obtained from the aerial parts ofAceriphyllum rossii (Saxifragaceae) was fractionated into ethyl acetate (EtOAc),n-BuOH and H₂O layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc andn-BuOH layers afforded six flavonol glycosides. They were identified as kaempferol 3-O-β-D-glucopyranoside (astragalin,1), quercetin 3-O-β-D-glucopyranoside (isoquercitrin,2), kaempferol 3-O-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside (3), quercetin 3-O-α-L-rhamnopyranosyl (1→6)-β-D-glucopyrano-side (rutin,4), kaempferol 3-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside] (5) and quercetin 3-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside] (6) on the basis of several spectral data. The antioxidant activity of the six compounds was investigated using two free radicals such as the ABTS free radical and superoxide anion radical. Compound1 exhibited the highest antioxidant activity in the ABTS2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging method. 100 mg/L of compound1 was equivalent to 72.1±1.4 mg/L of vitamin C, and those of compounds3 and5 were equivalent to 62.7±0.5 mg/L and 54.3±1.3 mg/L of vitamin C, respectively. And in the superoxide anion radical scavenging method, compound5 exhibited the highest activity with an IC₅₀ value of 17.6 ± 0.3 μM. In addition, some physical and spectral data of the flavonoids were confirmed.     

Leeaoside,a new megastigmane diglycoside from the leaves of <Emphasis Type="Italic">Leea thorelii</Emphasis> Gagnep

A new megastigmane diglycoside, leeaoside, was isolated along with four known compounds; benzyl O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside, quercetin 3-O-α-l-rhamnopyranoside, myricetin 3-O-α-l-rhamnopyranoside and citroside A from the leaves of Leea thorelli. The structure determinations were based on physical data and spectroscopic evidence.     

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.     

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.     

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.     

Polygosumic acid,a new cadinane sesquiterpene from <Emphasis Type="Italic">Polygonum viscosum</Emphasis>, inhibits the growth of drug-resistant <Emphasis Type="Italic">Escherichia coli</Emphasis> and <Emphasis Type="Italic">Staphylococcus aureus</Emphasis> (MRSA) in vitro

Three new sesquiterpenes, 6-hydroxy-7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid methyl ester (1, named viscozulenic acid methyl ester), 7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid 1-methyl ester (2, named viscoazucinic acid) and 3-oxo-1-epi-sclerosporin (3, named polygosumic acid), have been isolated from the chloroform extract of the aerial parts of Polygonum viscosum by reversed-phase preparative high performance liquid chromatography (HPLC). The structures of these compounds were established conclusively by ultraviolet (UV), mass spectrometry (MS) and a series of 1D and 2D nuclear magnetic resonance (NMR) analyses. The anti-bacterial properties of 1–3 against 12 pathogenic bacterial strains have also been assessed by the rapid and robust microtitre-plate-based serial dilution method incorporating resazurin as an indicator of cell growth. Polygosumic acid was the most active among the sesquiterpenes and inhibited the growth of penicillin-resistant Escherichia coli (minimum inhibitory concentration, MIC=0.05 mg/ml) and methicillin-resistant Staphylococcus aureus (MRSA) (MIC=0.10 mg/ml).