<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.     

Biological activity of <Emphasis Type="Italic">Entada phaseoloides</Emphasis> and <Emphasis Type="Italic">Entada rheedei</Emphasis>

The aim of our study is to find functional compounds from natural resources. We focus on plants grown in tropical areas, especially Madagascar and Thailand, because they have unique flora and are expected to contain interesting compounds. We review the functional compounds of the seed kernels of Entada phaseoloides and E. rheedei and their biological activities such as anti-proliferation and melanogenesis inhibitory properties, etc.     

<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.     

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.     

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.     

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.     

<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.     

Three new <Emphasis Type="Italic">C</Emphasis>-glycosyflavones with acetyl substitutions from <Emphasis Type="Italic">Swertia mileensis</Emphasis>

Three new acetylated C-glycosylflavones, 3″,6″-di-O-acetylswertiajaponin (1), 4″,6″-di-O-acetylswertiajaponin (2), and 6″-O-acetylswertiajaponin (3), together with six known compounds were isolated from the whole herb of Swertia mileensis. Their structures were elucidated on extensive NMR experiments and mass spectrometry studies. ¹H and ¹³C NMR data exhibited doublet signals at room temperature. Variable temperature ¹H NMR experiments were carried out to investigate the presence of rotational isomerism of C-glycosylflavones. All compounds showed potential antioxidant activities against apoptosis of H₂O₂-induced human embryo liver L02 cells.     

Chemical composition and antimicrobial activity of the volatile oils of <Emphasis Type="Italic">Geranium sanguineum</Emphasis> L. and <Emphasis Type="Italic">G</Emphasis>. <Emphasis Type="Italic">robertianum</Emphasis> L. (Geraniaceae)

Abstract  

Volatile compounds of Geranium sanguineum and G. robertianum were isolated by hydrodistillation, analyzed in detail by GC and GC/MS and screened for their in vitro antibacterial and antifungal activity in a microdilution assay. In total, 304 constituents were identified, representing more than 90% of the isolated oils. The volatiles of G. sanguineum have been studied for the first time in this study. The antimicrobial assay showed a strong activity of the G. robertianum oil against Escherichia coli and Aspergillus fumigatus. Micrococcus flavus and A. fumigatus were the most susceptible strains to G. sanguineum oil.     

<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.     

Identification of medicinal <Emphasis Type="Italic">Dendrobium</Emphasis> species by phylogenetic analyses using <Emphasis Type="Italic">matK</Emphasis> and <Emphasis Type="Italic">rbcL</Emphasis> sequences

Species identification of five Dendrobium plants was conducted using phylogenetic analysis and the validity of the method was verified. Some Dendrobium plants (Orchidaceae) have been used as herbal medicines but the difficulty in identifying their botanical origin by traditional methods prevented their full modern utilization. Based on the emerging field of molecular systematics as a powerful classification tool, a phylogenetic analysis was conducted using sequences of two plastid genes, the maturase-coding gene (matK) and the large subunit of ribulose 1,5-bisphosphate carboxylase-coding gene (rbcL), as DNA barcodes for species identification of Dendrobium plants. We investigated five medicinal Dendrobium species, Dendrobium fimbriatum, D. moniliforme, D. nobile, D. pulchellum, and D. tosaense. The phylogenetic trees constructed from matK data successfully distinguished each species from each other. On the other hand, rbcL, as a single-locus barcode, offered less species discriminating power than matK, possibly due to its being present with little variation. When results using matK sequences of D. officinale that was deposited in the DNA database were combined, D. officinale and D. tosaense showed a close genetic relationship, which brought us closer to resolving the question of their taxonomic identity. Identification of the plant source as well as the uniformity of the chemical components is critical for the quality control of herbal medicines and it is important that the processed materials be validated. The methods presented here could be applied to the analysis of processed Dendrobium plants and be a promising tool for the identification of botanical origins of crude drugs.     

Novel cycloartane-type triterpenoid from the fruits of <Emphasis Type="Italic">Nandina</Emphasis><Emphasis Type="Italic">domestica</Emphasis>

A novel cycloartane-type triterpenoid was isolated from the fruits of Nandina domestica (Berberidaceae). The structure was characterized as 24-methylene-3-oxocycloartane 13-carboxylic acid on the basis of NMR spectroscopic data.     

Safety of an injection with a mixture of extracts from <Emphasis Type="Italic">Herba Artemisiae annuae</Emphasis>, <Emphasis Type="Italic">Fructus Gardeniae</Emphasis> and <Emphasis Type="Italic">Flos Lonicerae</Emphasis>

Objective This study aimed to evaluate the safety for an injection with a mixture of extracts from Herba Artemisiae annuae, Fructus Gardeniae and Flos Lonicerae and to determine the risk factors that may affect its adverse drug reactions. Methods A drug-oriented prospective observational study was performed. Physicians filled in clinical observation forms with detailed information of the patients including general information, drug information, therapeutic effects and adverse drug events. The adverse drug reaction factors were analyzed by both mono-factor and multiple-factor logistic regression methods. Results From April to July 2007, we collected 12,427 observation forms from 46 hospitals in Jiangsu Province of China. Among the 11,707 observation forms we analyzed, 8,074 patients were children younger than 14 years old (69%). Among 51 reported adverse drug events, 45 cases were adverse drug reactions. The total adverse drug reaction incidence of the injection was 0.38%. While most adverse drug reactions were previously known (e.g., rash, pruritus, vomiting and diarrhea), we observed three new ADR symptoms: shiver, phlebitis and anhelation. All the adverse drug reactions were controlled very well through the follow-up therapy, and none of them was life threatening. The mono-factor analysis showed that adverse drug reactions of the injection were significantly correlated with total medication dose (P = 0.0049) and combination medication (P = 0.0143), especially with antimicrobial drugs (P = 0.0079) and macrolides (P = 0.0017). The multiple factor analysis confirmed these results: medication dosage and combination medication had a crucial impact on adverse drug reactions of the injection; the risk was increased by 24.8% (the estimated value of relative risk was 1.248, 95% confidence interval: 1.054–1.479) and 89% (1.890, 1.001–3.566), respectively. Conclusion The total adverse drug reaction incidence of the injection was 0.38% and lower than we expected. Moreover, we observed three new adverse drug reactions, none of which was severe.     

Bioassay-guided isolation of fatty acid synthase inhibitory diterpenoids from the roots of <Emphasis Type="Italic">Salvia miltiorrhiza</Emphasis> Bunge

Fatty acid synthase (FAS) is considered as a novel drug target for the development of anticancer and anti-obesity agents. Bioassay-guided fractionation of a n-hexane-soluble extract prepared from the roots of Salvia miltiorrhiza Bunge (Labiatae), using an in vitro enzyme assay, led to the isolation of five abietane diterpenoids: 15,16-dihydrotanshinone I (1), cryptotanshinone (2), tanshinone I (3), tanshinone IIA (4), and dansenspiroketallactone (5). Compounds 1–5 were tested for their in vitro FAS inhibitory activity and, except for compound 5 (IC₅₀ > 100 μM), compounds 1–4 inhibited the enzyme activity with IC₅₀ values ranging from 12.0 to 30.3 μM. Our findings may be partially related to the anticancer activity of abietane diterpenoids from the plant, suggesting a further study on the anticancer potential of tanshinone derivatives.     

Anti-inflammatory and anticholinesterase activity of six flavonoids isolated from <Emphasis Type="Italic">Polygonum</Emphasis> and <Emphasis Type="Italic">Dorstenia</Emphasis> species

This study was aimed at investigating the anti-inflammatory and anticholinesterase activity of six naturally occurring flavonoids: (?) pinostrobin (1), 2′,4′-dihydroxy-3′,6′-dimethoxychalcone (2), 6-8-diprenyleriodictyol (3), isobavachalcone (4), 4-hydroxylonchocarpin (5) and 6-prenylapigenin (6). These compounds were isolated from Dorstenia and Polygonum species used traditionally to treat pain. The anti-inflammatory activity was determined by using the Griess assay and the 15-lipoxygenase inhibitory activity was determined with the ferrous oxidation-xylenol orange assay. Acetylcholinesterase inhibition was determined by the Ellman’s method. At the lowest concentration tested (3.12 µg/ml), compounds 2, 3 and 4 had significant NO inhibitory activity with 90.71, 84.65 and 79.57 % inhibition respectively compared to the positive control quercetin (67.93 %). At this concentration there was no significant cytotoxicity against macrophages with 91.67, 72.86 and 70.86 % cell viability respectively, compared to 73.1 % for quercetin. Compound 4 had the most potent lipoxygenase inhibitory activity (IC₅₀ of 25.92 µg/ml). With the exception of (?) pinostrobin (1), all the flavonoids had selective anticholinesterase activity with IC₅₀ values ranging between 5.93 and 8.76 µg/ml compared to the IC₅₀ 4.94 µg/ml of eserine the positive control. These results indicate that the studied flavonoids especially isobavachalcone are potential anti-inflammatory natural products that may have the potential to be developed as therapeutic agents against inflammatory conditions and even Alzheimer’s disease.     

Two new antibacterial norabietane diterpenoids from cyanobacteria, <Emphasis Type="Italic">Microcoleous </Emphasis><Emphasis Type="Italic">lacustris</Emphasis>

Two abietane diterpenes were isolated from cyanobacteria Microcoleous lacustris, 20-nor-3α-acetoxyabieta-5,7,9,11,13-pentaene and 20-nor-3α-acetoxy-12-hydroxy-abieta-5,7,9,11,13-pentaene. These compounds were assayed against Staphylococcus aureus, Staphylococcus epidermidis, Salmonella typhi, Vibrio cholerae, Bacillus subtilis, Bacillus cereus, Escherichia coli, and Klebsiella pneumoniae. Both compounds showed activity against S. aureus, S. epidermidis, S. typhi, and V. cholerae, but not against the other bacteria.     

Antioxidant <Emphasis Type="Italic">C</Emphasis>-glycosylflavones of <Emphasis Type="Italic">Drymaria cordata</Emphasis> (Linn.) Willd

A new C-glycosylflavone, drymaritin E (6-C-(3-keto-β-digitoxopyranosyl)-4′-O-(β-d-glucopyranosyl)-7-methoxyl-5,4′-dihydroxylflavone) 1 was isolated from the oily upper phase (SU) of the MeOH extract from aerial parts of Drymaria cordata together with two known compounds (cassiaoccidentalin A 2 and anemonin 3) and an inseparable mixture of two known C-glycosylflavones 5,4′-dihydroxy-7-methoxyflavone-6-C-(2′′-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside 4a and 5,7,3′,4′-tetrahydroxyflavone-6-C-(2′′-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside 4b. The alkaline hydrolysis of 3 led to a new hemisynthetic derivative, sodium anemonate (sodium 2-((1’E) 2′-sodium-carboxylate-vinyl)-5-oxo-cyclohex-1-ene carboxylate) 3a. The chemical structures were determined by spectroscopic methods (¹H NMR, ¹³C NMR, ¹H-¹H COSY, HMBC, HSQC, and NOESY) and mass spectrometry (ESI–MS). C-glycosylflavones had significant free radical-scavenging activities on the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, SU and compounds 3 and 3a exhibited no activity. In particular, compound 1 exhibited a concentration-dependent radical scavenging activity on DPPH with EC₅₀ of 31.43 µg/mL.