Chemical constituents of the leaves of <Emphasis Type="Italic">Glochidion obliquum</Emphasis> and their bioactivity

A new flavonoid glycoside, globlin A (1), and eleven known compounds were isolated from methanolic extracts of the leaves of Glochidion obliquum. The structure of this new compound was established with a combination of 2D NMR techniques (COSY, NOESY, HMQC and HMBC) and HR-ESI-MS analyses. Chemical structures of the other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Some of the isolates were examined for their bioactivities. Among the tested compounds, rotundic acid (4) displayed significant cytotoxicity and anti-inflammatory activities.     

<Emphasis Type="Italic">ent</Emphasis>-Abietane diterpenoids from <Emphasis Type="Italic">Isodon xerophilus</Emphasis>

Three new ent-abietanoids, named xerophilusins XIV–XVI, and four known analogues, as well as four known chemical constituents were isolated from the leaves of Isodon xerophilus. Their structures were elucidated by extensive spectroscopic studies, and comparison with literature data. In addition, the cytotoxic activity of the ent-abietanoids against chronic myelogenous leukemia (K562), stomach adenocarcinoma (MKN45), and hepatocellular carcinoma (HepG2) human cell lines was investigated and no activities were observed.     

Genetic and chemical comparison of Boi (<Emphasis Type="Italic">Sinomeni Caulis</Emphasis><Emphasis Type="Italic">et Rhizoma</Emphasis>) and Seifuto (<Emphasis Type="Italic">Caulis Sinomenii</Emphasis>)

Boi and its original plant Sinomenium acutum from Japan were compared with Seifuto and its botanical origins from China in terms of their internal transcribed spacer (ITS) sequences and major chemical components. Boi, Seifuto, and their botanical origins overall showed seven variable sites in the ITS sequence and six genotypes. Japanese S. acutum and Boi had one nucleotide variation at position 593 to show two genotypes (J1 and J2) and their heterozygote (J3). Seifuto samples and their botanical origins, S. acutum and S. acutum var. cinereum from China, showed three genotypes (C1, C2, and C3), which did not agree with the botanical classification, indicating that they cannot be distinguished according to their ITS sequences. All Seifuto samples from Henan market showed the same ITS genotype (C1). The Japanese and Chinese genotypes differed in the nucleotide position 424, which can be used to distinguish the country of origin of these materials. In the HPLC analysis of six major components, sinomenine (1), magnoflorine (2), menisperine (3), 6-O-methyllaudanosoline glucoside (4), liriodendrin (5), and menisdaurin (6), all were detected in Boi, whereas five (all except for menisdaurin) were detected in Seifuto. The main component in the rhizome of Seifuto was sinomenine, whereas magnoflorine was the main component in the rhizome and the climbing stem of Boi. The content of sinomenine in Seifuto was almost twice that in Boi. Although the individual content of alkaloids 1–4 differed between Boi and Seifuto, the total contents of these alkaloids were comparable between them both in the climbing stem and rhizome.     

<Emphasis Type="Italic">In Vitro</Emphasis> hepatoprotective compounds from <Emphasis Type="Italic">Suaeda glauca</Emphasis>

Bioassay-guided fractionation of the MeOH extract of Suaeda glauca yielded four phenolic compounds, methyl 3,5-di-O-caffeoyl quinate (1) and 3,5-di-O-caffeoyl quinic acid (2), isorhamnetin 3-O-beta-D-galactoside (3), and quercetin 3-O-beta-D-galactoside (4). Compounds 1 and 2 were hepatoprotective against tacrine-induced cytotoxicity in human liver-derived Hep G2 cells with the EC(50) values of 72.7+/-6.2 and 117.2+/-10.5 microM, respectively. Silybin as a positive control showed an EC(50) value of 82.4+/-4.1 microM.     

A new <Emphasis Type="Italic">Erythrina</Emphasis> alkaloid from <Emphasis Type="Italic">Erythrina herbacea</Emphasis>

A new Erythrina alkaloid, 10-hydroxy-11-oxoerysotrine (1), has been isolated from the flowers of Erythrina herbacea together with five known compounds: erytharbine (2), 10,11-dioxoerysotrine (3), erythrartine (4), erysotramidine (5) and erysotrine-N-oxide (6). The structure of the new compound was elucidated on the basis of its spectral data, including 2-D NMR and mass (MS) spectra. The new compound is a rare C-10 oxygenated Erythrina alkaloid. The antioxidant activities of the isolated compounds 1–6 were evaluated by scavenging with peroxynitrite.     

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.     

Biologically active <Emphasis Type="Italic">C</Emphasis>-alkylated flavonoids from <Emphasis Type="Italic">Dodonaea viscosa</Emphasis>

A new C-alkylated flavonoid (5,7-dihydroxy-3′-(4″-acetoxy-3″-methylbutyl)-3,6,4′-trimethoxyflavone (1), along with two known C-alkylated flavonoids (5,7-dihydroxy-3′-(3-hydroxymethylbutyl)-3,6,4′-trimethoxyflavone (2), 5,7,4′-trihydroxy-3′-(3-hyroxymethylbutyl)-3,6-dimethoxyflavone (3) and two new source C-alkylated flavonoids (5,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-3,6,4′-trimethoxyflavone (4), 5,7,4′-trihydroxy-3,6-dimethoxy-3′-isoprenyl-flavone (5) were isolated from the aerial parts of Dodonaea viscosa. The structures of all compounds were established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry. The isolated compounds were evaluated for their inhibitory effect on urease and α-chymotrypsin enzyme. All the compounds (1–5) exhibited mild inhibition against urease but remained recessive in case of α-chymotrypsin.     

Lignan constituents from <Emphasis Type="Italic">Chloranthus japonicus</Emphasis> Sieb.

A new coumarinolignan glucoside named yinxiancaoside C, along with five known benzofuran lignans, have been isolated from the whole plant of Chloranthus japonicus Sieb. The structures of compounds 1–6 were elucidated by chemical and spectroscopic methods including 1D-NMR, 2D-NMR, ESI-MS and HR-ESI-MS. Five known benzofuran lignans were firstly discovered in the Chloranthaceae. In addition, the cytotoxic activity of the isolated compounds against human hepatoma (Hepg-2), ovarian carcinoma (OV420), and breast cancer (MCF-7) cells was investigated by MTT method.     

Cytotoxic constituents of <Emphasis Type="Italic">Amanita subjunquillea</Emphasis>

As part of our systematic study of Korean toxic mushrooms, we have investigated the constituents of Amanita subjunquillea. The column chromatographic separation of the MeOH extract of A. subjunquillea led to the isolation of four ergosterols, two cerebrosides and four cyclopeptides. Their structures were determined by spectroscopic methods to be (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9,22-triene-3beta-ol (1), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (2), (22E,24R)-5alpha,6alpha-epoxyergosta-8,22-diene-3beta,7beta-diol (3), (24S)-ergost-7-en-3beta-ol (4), 8,9-dihydrosoyacerebroside I (5), soyacerebroside I (6), beta-amanitin (7), phalloin (8), alpha-amanitin (9), and phalloidin (10). The compounds 1-6 and 8 were isolated for the first time from this mushroom. The isolated compounds were evaluated for the cytotoxicity against A549, SK-OV-3, SK-MEL-2 and HCT15 cells. Compound 9 exhibited significant cytotoxic activity against A549, SK-OV-3, SK-MEL-2 and HCT15 with ED(50) values of 1.47, 0.26, 1.57 and 1.32 microM, respectively.     

<Emphasis Type="Italic">In Vitro</Emphasis> antioxidant and anti-inflammatory activities of Jaceosidin from <Emphasis Type="Italic">Artemisia princeps</Emphasis> Pampanini <Emphasis Type="Italic">cv.</Emphasis> Sajabal

Oxidized low-density lipoprotein (oxLDL) plays a key role in the inflammatory processes of atherosclerosis. Jaceosidin isolated from the methanolic extracts of the aerial parts of Artemisia princeps Pampanini cv. Sajabal was tested for antioxidant and anti-inflammatory activities. Jaceosidin inhibited the Cu²⁺-mediated LDL oxidation with IC₅₀ values of 10.2 μM in the thiobarbituric acid-reactive substances (TBARS) assay as well as the macrophage-mediated LDL oxidation. The antioxidant activities of jaceosidin were exhibited in the conjugated diene production, relative electrophoretic mobility, and apoB-100 fragmentation on copper-mediated LDL oxidation. Jaceosidin also inhibited the generation of reactive oxygen species (ROS) concerning in regulation of NF-κB signaling. And jaceosidin inhibited nuclear factor-kappa B (NF-κB) activity, nitric oxide (NO) production, and suppressed expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages.     

Preliminary phytochemical investigation of <Emphasis Type="Italic">Lychnis flos-cuculi</Emphasis> herbs

Five polyphenolic compounds were identified from the diethyl ether and ethyl acetate extracts of the herb of ragged robin, Lychnis flos-cuculi L. (Caryophyllaceae). The identified and isolated compounds were established as a caffeic acid, luteolin, apigenin, apigenin 8-C-β-d-glucopyranoside (vitexin) and luteolin 8-C-β-d-glucopyranoside (orientin) by means of extensive spectroscopic studies, including UV and NMR, and confirmed by their chromatographic behavior—TLC and HPLC analyses. This is the first report of occurrence of these compounds in L. flos-cuculi.     

Chemical constituents from <Emphasis Type="Italic">Lobelia chinensis</Emphasis> and their anti-virus and anti-inflammatory bioactivities

In total, forty six compounds, including the novel compound lobechine (1), were characterized from the methanol extracts of Lobelia chinensis. The chemical structures of known metabolites were identified by comparing their spectroscopic and physical data with compounds reported in the literature. The structure of lobechine (1) was comprehensively established with the aid of 1D and 2D NMR spectroscopic analyses. In addition, selected isolates were screened for their inhibition of HSV-1 replication, superoxide anion generation, and elastase release. Among the tested compounds, scoparone (10) exhibited significant inhibition of superoxide anion generation with IC₅₀ of 6.14 ± 1.97 μM and lobechine (1) exhibited moderate inhibition of elastase release with IC₅₀ of 25.01 ± 6.95 μM, respectively.     

MDMA induces <Emphasis Type="Italic">Per1</Emphasis>, <Emphasis Type="Italic">Per2</Emphasis> and <Emphasis Type="Italic">c-fos</Emphasis> gene expression in rat suprachiasmatic nuclei

Rationale  

±3,4-Methylenedioxymethamphetamine (MDMA, ‘ecstasy’) is a psychoactive drug that has marked effects on the serotonergic system. Serotonergic agonists are known to interact with the circadian pacemaker located in the suprachiasmatic nuclei (SCN).     

Study of constituents of <Emphasis Type="Italic">Veronicastrum villosulum</Emphasis>

We investigated the constituents of Veronicastrum villosulum (Miquel) Yamazaki (Scrophulariaceae), an endangered species belonging to the IA group. From the aerial parts of this plant cultivated at the botanical garden of Sojo University, we isolated two new cucurbitacine-type glycosides, 3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosides of 3β,25-dihydroxycucurbit-5,23(E)-diene-7-one-25-methyl ether and 3β,23-dihydroxycucurbit-5,24-diene-7-one-23-methyl ether.     

Biological activity of chemical constituents from <Emphasis Type="Italic">Clausena harmandiana</Emphasis>

The activity guided fractionation of the Clausena harmandiana root extracts led to the isolation of a coumarin, a ferulate, and eight carbazoles. This is the first report of the isolation of compounds 2–4 and 6–10 from this species, and this is the first time 10 was isolated from this genus. Compound 4 showed strong cytotoxicity against NCI-H187 cells with an IC₅₀ value of 1.63 μg/mL. Compound 5 demonstrated strong cytotoxicity against MCF-7 and KB cell lines with IC50 values of 2.21 and 1.74 μg/mL, respectively. Compounds 3 and 4 exhibited moderate cytotoxicity against the MCF-7 cell line, and 8 showed moderate cytotoxicity against NCIH187 and KB cell lines. Compounds 3 and 5 showed antiplasmodial activity with IC₅₀ values of 3.27 and 2.94 μg/mL, respectively.     

Antioxidant activity of red pigments from the lichens <Emphasis Type="Italic">Lethariella sernanderi</Emphasis>, <Emphasis Type="Italic">L. cashmeriana</Emphasis>, and <Emphasis Type="Italic">L. sinensis</Emphasis>

A yellow and new dark red pigments were isolated from Lethariella sernanderi, L. cashmeriana, and L. sinensis as antioxidant components. The yellow pigment was identified as canarione (1), and the others were determined to be 1,2-quinone derivatives, rubrocashmeriquinone (2) and 7-chlororubrocashmeriquinone (3), and 7-chlorocanarione (4) by analysis of their spectroscopic data.     

Two new phenolic constituents of<Emphasis Type="Italic">Humulus japonicus</Emphasis> and their cytotoxicity test<Emphasis Type="Italic">In Vitro</Emphasis>

Two new phenolic constituents (4 and 6), together with four known constituents, methyl ferulate (1), eugenyl-beta-D-glucopyranoside (2), apigenin-7-O-beta-D-glucopyranoside (3), and (E)-resveratrol-3-O-beta-D-glucopyranoside (5) were isolated from the MeOH extract of the aerial part sof Humulus japonicus. The structures of the new compounds were determined by spectroscopic methods to be divarin-3-O-beta-glucopyranoside (4), and lariciresinol-9-O-beta-xylopyranoside (6). Compounds 1 and 3 exhibited moderate cytotoxicity against two human cancer cell lines (SK-OV-3 and HCT15) with ED50 values ranging from 8.84 to 8.79 microM.     

A new iridoid and other chemical constituents from<Emphasis Type="Italic">pedicularis kansuensis</Emphasis> forma<Emphasis Type="Italic">albiflora</Emphasis> Li.

A new iridoid (1) and thirteen known compounds 2-14 were isolated from Pedicularis kansuensis forma albiflora Li., and their structures were elucidated by spectroscopic methods including 2D-NMR techniques.