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Natural product research

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a State Key Laboratory of Natural and Biomimetic Drugs and Department of Natural Medicines , School of Pharmaceutical Sciences, Peking University Health Science Center , Beijing , 100191 , China.
In this study, a simple, sensitive and reliable fingerprint analysis method by high-performance liquid chromatography coupled with diode array detection was developed for raw materials of Hedysari Radix, which is a famous traditional Chinese medicine and widely used as a restorative food. Then the developed method was subsequently applied to analyse 48 samples collected or purchased from different origins. Twenty-six common fingerprint peaks, including six definitely identified peaks, were found in total, and were involved for further characterisation and quality evaluation of Hedysari Radix. The chemical quality of commercial samples and samples collected in spring varied obviously, while those of the cultivated samples collected in autumn were relatively stable, indicating that it is better to harvest Hedysari Radix in autumn and that more attention should be paid to the standardisation of the process of harvesting, manufacturing and storage of Hedysari Radix.
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a Dipartimento di Biotecnologie per il Monitoraggio Agro-Alimentare ed Ambientale (BIOMAA), Facoltà di Agraria - Salita Melissari , Università Mediterranea di Reggio Calabria , I-89124 , Reggio Calabria , RC , Italy.
Foliar volatiles and essential oils of Calamintha nepeta (L.) Savi, a Mediterranean plant species belonging to the Labiatae family, were investigated for their phytotoxic activities on seed germination and root growth of crops (Lactuca sativa L. and Raphanus sativus L.) and weed species (Lolium perenne L. and Amaranthus retroflexus L.). Foliar volatiles of C. nepeta (L.) Savi strongly inhibited both germination and root growth of lettuce, and its essential oils, especially at 125, 250 and 500 μL/L, inhibited both processes in lettuce, radish and A. retroflexus L. species, while displaying a little effect on L. perenne L. By GC-MS, 28 chemicals were identified: 17 monoterpenes, 8 sesquiterpenes, 1 diterpene and 2 miscellaneous. Pulegone was the main constituent of the C. nepeta (L.) Savi essential oils. The terpenic components of essentials oils were probably responsible for the phytotoxic activities.
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a Ethnic Pharmaceutical Institute of College of Southwest University for Nationalities , Chengdu , 610041 , P. R. China.
A series of polyketide metabolites (1-6), including a new chlorinated diphenyl ether (4-chloro-7,4'-dihydroxy-5,2'-dimethoxy-2-methylformate-6'-methybenzophone, 1), were isolated from the solid-fermented rice culture of Penicillium griseofulvum cib-119. The structure of compound 1 was determined on the basis of NMR spectra and single-crystal X-ray diffraction analyses. In addition, compound 1 showed weak cytotoxic activity against prostatic carcinoma cell (PC-3). Compounds 3-5 exhibited significant antimicrobial activities against Staphylococcus aureus and Bacillus subtilis.
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a College of Food and Bioengineering, Henan University of Science and Technology , Luoyang , 471003 , China.
The purpose of this study was to evaluate the sedative and hypnotic effects of Eucommiol, a monomer compound extracted from male Eucommia flowers using a system solvent method. Eucommiol shows significant effects in mice, including reduced spontaneous activity, and increased the sleep ratio or lengthened the sleep time with a subthreshold or superthreshold dose of pentobarbital sodium, respectively. In addition, could effectively shorten sleep latency, reduce convulsion rate and prolong convulsion latency. These findings intensely indicated that Eucommiol has excellent sedative and hypnotic effects.
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a Department of Pharmacognosy , Faculty of Pharmacy, Suez Canal University , 41522 , Ismailia , Egypt.
Some Egyptian plants were screened against highly pathogenic avian influenza strain H5N1 using plaque inhibition assay in Madin-Darby canine kidney. The results indicated that the extracts of Red Sea grass Thallasodendron ciliatum possessed potent antiviral activity (100% inhibition at the concentration of 1 μg mL(- 1)). The bioactivity-guided fractionations led to the isolation of a new diglyceride ester (1) along with asebotin (2) for the first time from the plant. The two isolates showed reduction of virus titre by 67.26% and 53.81% inhibition at concentration of 1 ng mL(- 1), respectively.
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a Department of Chemistry and Materials Science , Tokyo Institute of Technology , Meguro , Tokyo , 152-8551 , Japan.
Chemical investigation of the glandular trichome exudate of Verbascum blattaria f. erubescens (Scrophulariaceae) led to the isolation of four new glycerides, 1-O-acetyl-2-O-[(R)-3-hydroxytetradecanoyl]-sn-glycerol, 1-O-acetyl-2-O-[(R)-3-hydroxyhexadecanoyl]-sn-glycerol, 2-O-[(R)-3-hydroxytetradecanoyl]glycerol and 2-O-[(R)-3-hydroxyhexadecanoyl]glycerol. Their structures, including the configurations at the stereogenic centres, were elucidated from spectral evidence and chemical transformations.
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a Department of Microbiology and Immunology , Biosciences Institute, UNESP , Botucatu , SP , 18618-970 , Brazil.
A possible immunomodulatory/anti-inflammatory effect of Baccharis dracunculifolia (Bd) and its major compound - caffeic acid (Ca)- on cytokines production (IL-1β, IL-6 and IL-10) by murine macrophages was investigated. Cells were incubated with Bd and Ca, and the inhibitory concentrations were tested before or after macrophages challenge with LPS. Bd and Ca stimulated IL-1β and inhibited IL-6 and IL-10 production. In LPS-challenge protocols, Bd prevented LPS action either before or after LPS challenge, whereas Ca prevented LPS effects only after LPS addition. Bd modulatory action on cytokines production may be at least in part mediated by Ca, since it has been shown to inhibit the transcription factor NF-κB. Further studies are still needed to evaluate Bd efficacy in inflammatory diseases, in order to explore its antiinflammatory activity in vivo.
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a Faculty of Pharmaceutical Sciences, Center for Research and Development of Herbal Health Products, Khon Kaen University , 123 Mitrapap Rd., Khon Kaen , 40002 , Thailand.
From mycelia of Lentinus polychrous, a Thai local edible mushroom cultured under solid-state fermentation, a new compound, 6-methylheptane-1,2,3,4,5-pentaol (1), and five ergostanoids, namely (22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (2), 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (3), ergosta-4,6,8(14),22-tetraen-3-one (4),(3β,5α,8α,22E)-5,8-diepoxy-ergosta-6,22-dien-3-ol (5) and 5,8-epidioxy-(3β,5α,8α,22E)-ergosta-6,9(11),22-trien-3-ol (6), was isolated and characterised. The compounds were determined for their oestrogenic and anti-oestrogenic activities by using human breast cancer T47D cells. All compounds had no oestrogenic activity but exhibited suppressive effect on oestradiol-enhanced cell proliferation. Among these compounds, only 4 significantly competed with oestradiol in the binding to oestrogen receptors (ERs) with higher selectivity to ERα than ERβ. These results may suggest that most compounds suppressed this oestradiol-enhanced T47D proliferation via other mechanisms rather than ER binding.
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a Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing , 100193 , P.R. China.
A new cyclohexylacetic acid derivative, named 2-{4-hydroxy-7-oxabicyclo [2.2.1] heptanyl}-acetic acid (1), was isolated from Emilia sonchifolia, together with a known analogue, 2-(1,4-dihydroxy cyclohexanyl)-acetic acid (2). Their structures were determined on the basis of spectroscopic techniques including IR, NMR, HR-ESI-MS and X-ray diffraction.
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a Department of Pharmacognosy , School of Pharmacy, Second Military Medical University , Shanghai 200433 , P.R. China.
Two new triterpenoid saponins celosin I (1) and celosin II (2) were isolated from the seeds of Celosia argentea L.(Amaranthaceae). The structures of the two new compounds were elucidated based on chemical analysis and spectral methods (IR, 1-D and 2-D NMR, ESI-MS, HR-ESI-MS). They exhibited significant hepatoprotective effect on carbon tetrachloride-induced and N,N-dimethylformamide-induced hepatotoxicity in mice.
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a Fujian Key Laboratory of Screening for Novel Microbial Products , Fujian Institute of Microbiology , Fuzhou , P.R. China.
A new 20-membered macrolide named as levantilide C was isolated from the Micromonospora strain FIM07-0019 recovered from shallow coastal waters near the island of Chiloe, Chile. The chemical structure of levantilide C was elucidated on the basis of one- and two-dimensional NMR analysis. Two known indole derivatives were also isolated from this strain. Levantilide C exhibited moderate antiproliferative activity against several tumour cell lines.
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a School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Box 79, Wenhua Road 103, Shenhe District , Shenyang , Liaoning Province , 110016 , PR China.
Two new compounds (triterpenoid saponin and heterocyclic compound), 2α,3β, 19α,23,30-pentahydroxyurs-12-en-28-oic acid-28-O-β-d-glucopyranosyl ester (1) and N-hydroxyl-hexahydroazepin-2,4-diones (2), with 11 known compounds, picein (3),(7S,8R)-dihydrodehydrodiconiferyl alcohol-9'-O-β-d-glucopyranoside (4),(+)-1-hydroxy-2-epipinoresinol-1-β-d-glucoside (5),(+)-1-hydroxypinoresinol-1-β-d-glucoside (6),(+)-1-hydroxypinoresinol-4'-β-d-glucoside (7), schaftside (6-C-β-d-glucopyranosyl-8-C-α-l-arabinosyl apigenin)(8), isoschaftside (6-C-α-l-arabinosyl-8-C-β-d-glucopyranosyl apigenin)(9), isorhamnetin-3-O-β-d-glucopyranoside (10), quercetin-3-O-β-glucuronide (11), 8-O-methylherbacetin-3-O-sophoroside (12) and kaempferol (13), were isolated from Potentilla multicaulis Bunge. The structure of the compounds was elucidated by chemical and spectral evidence.
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a Department of Plant Biochemistry, Faculty of Biology , University of Warsaw , ul. Miecznikowa 1 , 02-096 , Warszawa , Poland.
Analysis of the main triterpenoid profile of chloroform-soluble cuticular waxes of heather flowers and leaves by GC-MS revealed the following composition: five triterpene acids - betulinic, oleanolic, ursolic, 3-oxo-olean-12-en-28-oic and 3-oxo-ursan-12-en-28-oic; eight monohydroxyalcohols - α-amyrin, β-amyrin, cycloartanol, 24-methylenecycloartanol, friedelinol, germanicol, lupeol and taraxasterol; three dihydroxyalcohols - betulin, erythrodiol and uvaol; two aldehydes - oleanolic and ursolic; four ketones - α-amyrenone, 4-epi-friedelin, friedelin and taraxerone and seven steroids - campesterol, cholesterol, sitostanol, sitosterol, stigmasterol, stigmasta-3,5-dien-7-one and stigmastane-3,6-dione. Triterpenoids accounted for 20% and 65% by mass of flower and leaf waxes, respectively, which suggest that heather leaves represent a very promising source of these compounds. Ursolic acid was the principal triterpenoid in the cuticular wax of both organs, whereas among the neutral triterpenes, friedelin and uvaol were the most abundant in flowers and leaves, respectively. This report provides the first thorough overview of the triterpenoid composition of cuticular waxes of heather.
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a National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University , MS 38677 , USA.
Ethyl acetate extracts of Armillaria tabescens (strain JNB-OZ344) showed significant fungistatic and bacteristatic activities against several major human pathogens including Candida albicans, Cryptococcus neoformans, Escherichia coli and Mycobacterium intracellulare. Chemical analysis of these extracts led to the isolation and identification of four new compounds, emestrin-F (1), emestrin-G (2), 6-O-(4-O-methyl-β-D-glucopyranosyl)-8-hydroxy-2,7-dimethyl-4H-benzopyran-4-one (3) and cephalosporolide-J (4), along with five other previously known compounds, emestrin (5), cephalosporolide-E (6), decarestrictine-C(2)(7), ergosterol and brassicasterol. Structural elucidation of all compounds was carried out by NMR and MS analyses. Antimicrobial assays revealed that compounds 1 and 5 were responsible for the observed growth inhibitory activities of the fungal extracts against the human pathogens tested.
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a Department of Pharmacology , School of Pharmacy , 41012 Sevilla , Spain.
Sideritis perezlarae is a plant widely used in folk medicine in the South of Andalusia (Cádiz, Spain). In this work, a phytochemical analysis has led to the isolation and identification of the flavonoid 7-O- β -glucosyl-luteolin from a methanol extract. The total phenol content estimated by Folin-Ciocalteau assay and expressed as gallic acid equivalent per gram of dried fraction, was 102.54 ± 2.10 mg phenols per gram dry residue. The flavonoid content, investigated by AlCl(3) reagent, was 23.49 ± 0.90 mg flavonoids gram dry residue. The methanol extract has been evaluated for antioxidant (DPPH and TEAC assays) and cytotoxic (SRB assay) properties. In the DPPH radical scavenging assay, the IC(50) was 360 µg mL(-1). In the total antioxidant activity, calculated by the Trolox equivalent antioxidant activity (TEAC, mg g(-1) of dried fraction), the extract showed a high antioxidant capacity (TEAC value of 0.59 ± 0.02 mg g(-1)). The cytotoxic activity of the extract against a human adenocarcinoma cell line HT-29 presented an IC(50) = 69.47 ± 4.64 µg mL(-1).
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a Anhui Key Laboratory of Modernized Chinese Materia Medica , Anhui University of Traditional Chinese Medicine , Hefei 230031 , China.
A new lignan bombasinol A (1), together with three known compounds was obtained from the ethanol (95%) extract of roots of Bombax ceiba L. through its being subjected to silica gel and Sephadex LH-20 chromatography. Their structures were elucidated as 4-(4-(3,5-dimethoxyphenyl)hexahydrofuro[3,4-c]furan-1-yl)-2-methoxy-phenol (1), 5,6-dihydroxymatairesinol (2),(+)-pinoresinol (3) and matairesinol (4) on the basis of spectroscopic methods, including 1-D and 2-D NMR (HSQC and HMBC) experiments and by comparison of the data with those previously reported literatures. All these compounds were the first reported from Bombacaceae. The anti-Hepatitis B Virus (HBV) activity of all compounds isolated from B. ceiba in the research was evaluated. From the results of the HBV assay, these tested compounds showed inhibitory activity against HepG2 2.2.15 cell lines. Compounds 1-4 showed relative differences in their abilities to inhibit HBsAg secretion, with IC(50) values of 118.3, 123.7, 118.9 and 218.2 mM, respectively.
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[My paper] Cinzia Barbieri
a University of Torino , Department of Economics 'S. Cognetti de Martiis', Via Po 53 , 10124 Torino , Italy.
This study analysed particular regulations on the cultivation and collection of medicinal and aromatic plants (MAPs) in the European Union, Italy and several of its regions. Piedmont and Valle d'Aosta (Northwest), Tuscany (Central) and Sicily (South). The analysis should emphasise to private and/or public institutions the information to further develop and improve MAP cultivation, both in the considered context and beyond it.
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a Division of Organic Chemistry, National Chemical Laboratory , Pune 411008 , Maharashtra , India.
A new substituted 2,2-diphenylpropane (1) and two new ethoxylated aromatic monoterpene alcohols (2 and 4) have been isolated from the acetone extract of the aerial parts of Lavandula gibsoni, along with the known compounds 8-hydroxycarvacrol (3), 8-hydroxythymol (5), coumarin (6), 4-methylresorcinol (7), 7,4'-dimethylapigenin (8), salvigenin (9), β-sitosteryl-3-O-β-D-glucopyranosyl-6'-O-palmitate (10) and euscaphic acid D (11). The structures of the isolated compounds were assigned on the basis of their (1)H- and (13)C-NMR spectra and two-dimensional NMR techniques, which included COSY, HSQC, HMBC and NOESY experiments and comparison with the reported literature.
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a Program of Post-Graduation in Pharmaceutical Sciences, Federal University of Santa Maria - UFSM , Campus Camobi , Santa Maria , RS 97105-900 , Brazil.
This study is designed to examine the chemical composition of the essential oil obtained from Buddleja thyrsoides Lam leaves from south Brazil. Gas chromatography/mass spectrometry analysis resulted in the detection of 12 components, representing 91.4% of the total oil composition. Germacrene D (27.16%), 1,10-di-epi-Cubenol (13.37%), α-Cadinol (12.95%), Bicyclogermacrene (9.00%), Globulol (8.59%) and caryophylene E (5.26%) were the main components. To the best of our knowledge, this is the first study of the composition of essential oil of the B. thyrsoides collected in Brazil.
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a Department of Pharmacal Sciences , Harrison School of Pharmacy, Auburn University , 4306B Walker Building , Auburn , AL 36849 , USA.
Olean-12-en-3β-24 diol (A), auranamide (B), aurantiamide acetate (C), 2α,3β-dihydroxy-olean-12-en-28-oic acid (D) and quindoline (E) were isolated from the dichloromethane (CH(2)Cl(2)) extract of the stems of Justicia secunda (Acanthaceae). Liquid chromatography with ultraviolet and mass spectrometric detection was used to acquire more knowledge of the chemical composition of this extract and to monitor variations in profiles of both the isolated and the other non-identified compounds in Justicia refractifolia and Justicia graciliflora. The compound classes, phenolic and olefinic amides, feruloyltyramine amides, 2,5-diaryl-3,4-dimethyltetrahydrofuranoid lignans, peptide alkaloids, phenylalanine derivatives, conjugated ynones, indolquinoline alkaloids, triterpenes and pigments, were tentatively identified based on the LC-DAD-APCI-MS analysis. The most frequently encountered compound among the species was auranamide while the distribution of quindoline was limited to J. secunda. Moreover, the acetylcholinesterase inhibitory activity of the isolated compounds was determined.


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2013-06-20 05:24:55 © BioInfoBank Institute