Flavonoids from<Emphasis Type="Italic">Spatholobus suberectus</Emphasis>

Two pterocarpans [(6aR,11aR)-maackiain, (6aR,11aR)-medicarpin], one flavanone [(2S)-7-hydroxy-6-methoxy-flavanone], one isoflavan (sativan) and two isoflavones (pseudobaptigenin, genistein) were isolated from the Spatholobus suberectus (Leguminosae). Their chemical structures were determined by comparison of their spectroscopic parameters of CD, EIMS, 1D-NMR and 2D-NMR with those reported in the literatures. All of these compounds are reported for the first time from this plant through the present study.     

The inhibitory principle of lipopolysaccharide-induced nitric oxide production from<Emphasis Type="Italic">inula britannica</Emphasis> var.<Emphasis Type="Italic">chinensis</Emphasis>

A sesquiterpene lactone, 1-O-acetyl-4R,6S-britannilactone (1) isolated from the flowers of Inula britannica L. var. chinensis (Rupr.) Reg. (Compositae), was found as an iNOS inhibitory constituent for the first time with an IC50 value of 22.1 microM which is more potent than the positive control, L-N6-(1-iminoethyl)lysine (IC50 = 33.7 microM). Structure of compound 1 was identified by 1D and 2D NMR experiments and by comparison with the reference standard.     

New ceramide from<Emphasis Type="Italic">Alocasia macrorrhiza</Emphasis>

A new ceramide alomacrorrhiza A was isolated from the ethanolic extract of the plant Alocasia macrorrhiza (L.) Schott. Its chemical structure was elucidated as (2S,3S,4R)-2N-[(2'R)-2'-hydroxy-hexacosanoyl]-tetradecane-1,3,4-triol based on extensive 1D, 2D NMR, EI-MS, FAB-MS, HR-FAB-MS spectroscopic data and chemical degradation studies.     

Characteristics of chitosanases from<Emphasis Type="Italic">Aspergillus fumigatus</Emphasis> KB-1

Two chitosanases produced by Aspergillus fumigatus KB-1 were purified by ion exchange and size exclusion chromatographies. Molecular weights of chitosanases were 111.23 kDa (chitosanase I) and 23.38 kDa (chitosanase II). The N-terminal amino acid sequence of chitosanase II was determined as follows: YNLPNNLKQIYDKHKGKXSXVLAKGFTN. The optimum pH of the chitosanase I and II was 6.5 and 5.5, respectively. The optimum temperatures were 60 degrees C for chitosanase land 70 degrees C for chitosanase II. Hydrolysis products of two chitosanases were analyzed by HPLC and GPC. Chitosanase I hydrolyzed substrate to glucosamine. Chitosanase II produced chitooligosaccharides.     

Essential oil compounds from<Emphasis Type="Italic">Agastache rugosa</Emphasis> as antifungal agents against<Emphasis Type="Italic">Trichophyton</Emphasis> species

The antifungal activities of the essential oil from Agastache rugosa and its main component, estragole, combined with ketoconazole, one of the azole antibiotics commonly used to treat infections caused by Trichophyton species, were evaluated in this study. The combined effects were measured by the checkerboard microtiter and the disk diffusion tests, against T. erinacei, T. mentagrophytes, T. rubrum, T. schoenleinii and T. soudanense. Susceptibility of the five Trichophyton species to the oil alone, or ketoconazole alone, differed distinctly. The fractional inhibitory concentration indices (FICI) of ketoconazole combined with estragole or A. rugosa essential oil, against the tested Trichophyton species, were between 0.05 and 0.27, indicating synergistic effects. These drug combinations exhibited the most significant synergism against T. mentagrophytes, with FICIs of 0.05 and 0.09 for estragole and the essential oil fraction from A. rugosa, respectively. Isobolograms based on the data from checkerboard titer tests also indicated significant synergism between ketoconazole and the Agastache oil fraction or estragole, against the Trichophyton species evaluated. Trichophyton susceptibility to ketoconazole was significantly improved by combination with the Agastache rugosa oil fraction or its main component, estragole.     

Antioxidative constituents from<Emphasis Type="Italic">Buddleia officinalis</Emphasis>

Four flavonoids (1-4), a phenylethyl glycoside (5), and a phenylpropanoid glycoside (6) were isolated from the flowers of Buddleia officinalis (Loganiaceae). Their structures were determined by chemical and spectral analysis. Among the isolated compounds, luteolin (1) and acteoside (6) exhibited the most potent antioxidative activity on the NBT superoxide scavenging assay. In addition, compounds 1-6 revealed weak antifungal activity, and no hemolytic activity.     

<Emphasis Type="Italic">Pulsatilla</Emphasis> saponin D: The antitumor principle from<Emphasis Type="Italic">Pulsatilla koreana</Emphasis>

By bioassay-guided separation, an already known saponin, Pulsatilla saponin D was isolated from the root of Pulsatilla koreana Nakai as a antitumor component when evaluated by in vivo antitumor activity as well as in vitro cytotoxic activity test. It showed potent inhibition rate of tumor growth (IR, 82%) at the dose of 6.4 mg/kg on the BDF1 mice bearing LLC cells.     

Continentalic acid from <Emphasis Type="Italic">Aralia continentalis</Emphasis> induces growth inhibition and apoptosis in HepG2 cells

In this study, we investigated the effects of continentalic acid (CA, (-)-pimara-8(14), 15-diene-19-oic acid), a diterpenic acid, isolated from Aralia continentalis, on the proliferation and apoptosis induction of HepG2 cells. In 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, the inhibitory effect became gradually stronger with the passage of time, 24, 48 and 72 h after treatment with CA, and the most significant effect was observed at 72 h. CA treatment for 72 h induced DNA fragmentation in a dose-dependent manner. Furthermore, flow cytometric analysis of HepG2 cells exposed to CA showed that apoptotic cells increased in a dose-dependent manner. The induction of apoptosis in HepG2 cells by CA was mediated through the activation of caspase-3, Bak, and Bax, and then through the cleavage of peroxisome proliferator-activated receptor (PARP) and the down-regulation of Bcl-2. These results demonstrate that CA efficiently induces apoptosis and is a good candidate for further evaluation as an effective chemotherapeutic agent.     

Antimicrobial phenolic derivatives from<Emphasis Type="Italic">Dendranthema zawadskii</Emphasis> var.<Emphasis Type="Italic">latilobum</Emphasis> kitamura (Asteraceae)

A phytochemical study on the root ofDendranthema zawadskii var.latilobum Kitamura, using a series of silica gel column chromatography and reversed phase C-18 HPLC chromatography, led to the isolation of (1S, 2S)-1, 2, 3-trihydroxy-1-(3, 4-methylenedioxyphenyl)propane (1), 4-methoxycinnamic acid (2), acacetin (3) and caffeic acid methyl ester (4). The structures of these compounds were determined using spectroscopic analyses (UV, IR, HRTOFMS and NMR), with comparison of their spectral data with previously reported values. Compound1 was isolated for the first time, with compounds2 and4 from this plant reported for the first time. The antibacterial and antifungal activities of the isolated compounds were measured using the disc diffusion method. Also, their cytotoxicities against the cancer cell lines, A549, B16F1 and SK-Mel-2, and brine shrimp lethalities were evaluated.     

Antibacterial coumarins from<Emphasis Type="Italic">Angelica gigas</Emphasis> roots

Systematic fractionation of Angelica gigas roots led to the isolation of linear furano(pyrano)coumarins such as bergapten (1), decursinol angelate (2), decursin (3), nodakenetin (4) and nodakenin (5). The antibacterial activities of those compounds against pathogenic bacteria were investigated. Among the compounds tested, decursinol angelate (2) and decursin (3) exhibited significant antibacterial activity against Bacillus subtilis with the minimum inhibitory concentrations (MICs) of 50 and 12.5 microg/mL, respectively.     

A polyacetylene and flavonoids from<Emphasis Type="Italic">cirsium rhinoceros</Emphasis>

Cirsium rhinoceros Nakai (Compositae) is a herbaceous perennial native to Korea, whole plant of which has been used in folklore medicine. C. rhinoceros was extracted by a standard extraction procedure. Its n-hexane, CHCl3 and n-BuOH extracts were fractionated by column chromatography to provide a polyacetylene, a coumarin and five flavonoids. Ciryneol C, scopoletin, acacetin, cirsimarin were isolated for the first time from this plant.     

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.     

Total synthesis of norneolignans from<Emphasis Type="Italic">Krameria</Emphasis> species

The total synthesis of nomeolignans isolated from Krameria species, 2-aryl-5-(E)-propenylbenzofurans (5, 11), is described. The key step involves the one-pot reaction for 2-arylbenzofurans (2, 7) from 4-hydroxyphenylacetone with 4'-acetoxy-2-chloro-2-(methylthio)acetophenone (1) and 2-chloro-2-methylthio-(2',4',6'-trimethoxy)acetophenone (6) under Friedel-Crafts reactionconditions.     

Isolation of fatty acids with anticancer activity from<Emphasis Type="Italic">Protaetia brevitarsis</Emphasis> Larva

In this study, biologically active compounds were isolated from Protaetia brevitarsis larva (PBL) by dichloromethane extraction. The dichloromethane extract from PBL was highly cytotoxic to various cancer cells. From a silica gel column chromatograpy of this extract, we obtained four fractions (F-2, F-4, F-5 and F-7) having apoptosis-inducing activity. These fractions induced DNA ladder and caspase-3 activation during apoptosis in colon 26 tumor cells. In 1H and 13C NMR and mass spectral analysis of the fraction F-2 showing the highest apoptosis-inducing activity, we found that the fraction was composed of three free fatty acids such as palmitic acid, (Z)-9-octadecenoic acid and octadecenoic acid. These results indicate that the dichloromethane extract of PBL includes anticancer components composed of at least three fatty acids, and apoptosis-inducing activity of the extract was mediated by caspase-3 activation in tumor cells.     

Antidiabetic coumarin and cyclitol compounds from<Emphasis Type="Italic">Peucedanum japonicum</Emphasis>

The antidiabetic activity-guided fractionation and isolation of the 80% EtOH extracts from Peucedani Radix (Peucedanum japonicum, Umbelliferae) led to the isolation and characterization of a coumarin and a cyclitol as active principles, that is, peucedanol 7-O-beta-D-glucopyranoside (1) and myo-inositol (2). Their structures were identified by spectroscopic methods. Compound 1 showed 39% inhibition of postprandial hyperglycemia at 5.8 mg/kg dose, and compound 2 also significantly inhibited postprandial hyperglycemia by 34% (P<0.05).     

A new sesquiterpene lactone from<Emphasis Type="Italic">Artemisia rubripes</Emphasis> nakai

The chromatographic separation of a methylene chloride extract of Artemisia rubripes led to the isolation of a new sesquiterpene lactone (3), together with four known compounds, a coumarin (2) and three terpenes (1, 4, and 5). Their structures were characterized to be 1beta,6alpha-dihydroxy-4(15)-eudesmene (1), scopoletin (2), 1alpha,4beta-dihydroxy-8alpha-acetoxy-guaia-2,10(14), 11(13)-triene-6,12-olide (3), 1alpha,4beta-dihydroxy-8alpha-acetoxy-guaia-2,9,11(13)-triene-6,12-olide (4), and beta-sitosterol-3-O-beta-D-glycoside (5) by spectroscopic means.     

Neuraminidase Inhibitors from<Emphasis Type="Italic">Reynoutria elliptica</Emphasis>

In the course of screening neuraminidase inhibitors from herbal medicines, Reynoutria elliptica exhibited high inhibitory activity. Four active compounds were isolated from the ethyl acetate soluble fraction by consecutive purification using sillica gel, Sephadex LH-20 chromatography, and recrystallization. The chemical structures of these compounds were identified as 1,3,8-trihydroxy-6-methylanthraquinone (emodin) 1,8-dihydroxy-3-methoxy-6-methylanthraquinone (emodin 3-methyl ether; physcion), 1,3,8-trihydroxy-6-hydoxymethylanthraquinone (omega-hydroxyemodin), and 3,5,4'-trihydroxystilbene (trans-resvertrol) by spectral data including MS, 1H-, and 13C-NMR. The IC50 values of emodin, emodin 3-methyl ether, omega-hydroxyemodin, and trans-resvertrol were 2.81, 74.07, 10.49, and 8.77 microM, respectively. They did not inhibit other glycosidase such as glucosidase, mannosidase, and galactosidase, indicating that they were relatively specific inhibitors of neuraminidase.     

<Emphasis Type="Italic">Perilla frutescens</Emphasis> var. <Emphasis Type="Italic">frutescens</Emphasis> in northern Laos

Twenty-eight samples of mericarps of Perilla frutescens var. frutescens were collected through fieldwork performed in Phongsali and Xieng Khouang provinces in northern Laos. No perilla samples were collected from Savannakhet province in the south although more than 20 sites were investigated. Perilla plants are mostly grown mixed with dry-paddy rice by slash-and-burn cultivation in Laos. The most popular local name for perilla mericarps in the area was “Ma Nga Chan”. Weight of 1,000 grains and hardness of the mericarps were measured, and all mericarps were found to be large (weight of 1,000 grains around 2 g) and soft (limit load weight under 300 g), which were preferred for culinary use in Laos. The composition of the essential oils obtained from the herbaceous plants raised from the mericarps was divided into five types, perillaketone, elemicine plus myristicine, shisofuran, piperitenon, and myristicine, and GC–MS analysis of these Laotian perilla samples showed that they were similar to those of corresponding types of known Japanese perilla strains. One of the shisofuran-type perilla contained large amounts of putative α-naginatene, which is likely to be an intermediate of the biosynthesis of naginataketone. The farmers' indifference to the oil type of the leaf seems to leave Laotian perilla as a good genetic resource for studies of the biosynthesis of oil compounds.     

New Aconitine-Type C<Subscript>19</Subscript>-Diterpenoid Alkaloids from<Emphasis Type="Italic">Aconitum hemsleyanium</Emphasis> var.<Emphasis Type="Italic">circinacum</Emphasis>

Two new aconitine-type C19-diterpenoid alkaloids, hemsleyanines C (1) and D (2), were isolated from the roots of Aconitum hemsleyanium var. circinacum, their structures were determined by the chemical evidence and spectral analyses.     

Antimycobacterial and antioxidant flavones from<Emphasis Type="Italic">Limnophila geoffrayi</Emphasis>

The chloroform extract of the aerial part of Limnophila geoffrayi showed antimycobacterial and antioxidant activities. Bioassay-guided fractionation has led to the isolation of the flavones nevadensin (5,7-dihydroxy-6,8,4'-trimethoxyflavone, 1) and isothymusin (6,7-dimethoxy-5,8,4'-trihydroxyflavone, 2). Both compounds 1 and 2 exhibited inhibition activity against Mycobacterium tuberculosis, with equal MIC value of 200 microg/mL. Only compound 2 exhibited antioxidant activity against the radical scavenging ability of DPPH, with the IC50 value of 7.7 microg/mL. The crude hexane, chloroform and methanol extracts as well as the pure compounds 1 and 2 did not exhibit mutagenic activity in the Bacillus subtilis recassay.