A new pyrazine from Hypecoum erectum L / 药学学报

Four pyrazines were isolated from the n-butanol fraction of Hypecoum erectum L. by using various chromatographic methods, including MCI gel, ODS, silica gel and semi-preparative HPLC. The structures of the isolated compounds were identified as hyperectpyrazin A (1), 1′S-(6-methylpyrazin-2-yl)-ethane-1′,2′-diol (2), 2-hydroxymethyl-6-methylpyrazin (3) and pyrazine-2-carboxylic acid (4) by spectroscopy methods (1D NMR, 2D NMR, UV, IR, MS, etc.). The absolute configuration of compound 2 was determined by using the Mo2(OAc)4 induced CD analysis for the first time. Compound 1 was a new compound, compounds 2-4 were isolated from H. erectum for the first time. Compounds 1-4 were evaluated for their inhibition against acetylcholinesterase and nitric oxide generation induced by lipopolysaccharide-RAW264.7 macrophage cells. At a concentration of 50 μmol·L-1, compounds 2 and 4 displayed inhibitory effects on acetylcholinesterase with the inhibition rates of 44.40% and 43.99%, respectively.

Chemical profile, acetylcholinesterase, butyrylcholinesterase, and prolyl oligopeptidase inhibitory activity of Glaucium corniculatum subsp. refractum

Abstract Papaveraceae is one of the prominent alkaloid-containing families, and plants of the genus Glaucium (Papaveraceae) are known for their bioactive alkaloids. Glaucium species have been used in traditional medicine in Turkey as an analgesic, narcotic, sedative, and antitussive. In this study, it was planned to evaluate the inhibitory activity of an alkaloidal extract of Glaucium corniculatum subsp. refractum on acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and prolyl oligopeptidase (POP), as well as exploring the chemical profile of the plant by using Gas Chromatography-Mass Spectrometry (GC-MS). The AChE, BuChE and POP inhibition activities of the alkaloidal extract of G. corniculatum subsp. refractum were determined spectrophotometrically. A rapid GC-MS method was used to identify alkaloids that could be responsible for these inhibition activities. In total, eleven alkaloids were identified in the alkaloid extract of the plant by GC-MS. Allocyptopine (52.92%) and protopine (25.38%) were found as the major constituents. The alkaloidal extract of G. corniculatum subsp. refractum showed potent AChE inhibitory activity (IC50:1.25 µg/mL) and BuChE inhibitory activity (IC50: 7.02 µg/mL). The extract also showed a remarkable inhibitory effect on POP with an IC50 value of 123.69 µg/mL. This study presents the first GC-MS investigation and POP inhibitory activity of G. corniculatum subsp. refractum.

Study on chemical constituents of sponge-associated Aspergillus terreus / 药学实践杂志

Objective To study the chemical constituents of Aspergillus terreus from sponge epiphytic fungal. Methods Sephadex LH-20 column chromatography, silica gel column chromatography and high performance liquid chroma-tography were used to separate and purify the compounds. The structures of compounds were identified by spectroscopic data. The α-glucosidase inhibitory activity and antioxidant activity of the compounds were tested by PNPG and DPPH methods, respectively. Results Eight compounds were isolated from Aspergillus terreus and identified as methyl-3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate (1), terrelumamide A (2), emeheterone (3), (8R,9S)-dihydroisoflavipucine (4), (8S,9S)-dihydroisoflavipucine (5), cyclo(S-Pro-S-Phe) (6), brevianamide F (7), terrein (8). Compound 3 showed strong inhibitory activity against α-glucosidase and the IC50 value was 14.28 μmol/L. Conclusion Compounds 3, 4, 5, and 7 were obtained from Aspergillus terreus for the first time.

The NO inhibitory constituents from Illigera rhodantha / 药学学报

Sixteen compounds were isolated from the ethanol extract of Illigera rhodantha by silica gel, ODS, and Sephadex LH-20 column chromatographies. These compounds were identified as (2R,3R)-2,3-dihydroxy-2-methylbutane-1,4-diyldibenzoate (1), p-hydroxyphenethyl trans-ferulate (2), 4-O-benzoyl-2-C-methyl-D-erythritol (3), N-trans feruloyl-3-methyldopamine (4), tribulusamide A (5), cryptomeridiol (6), teuclatriol (7), oleanolic acid (8), icario A2 (9), vanillic acid (10), p-hydroxybenzoic acid (11), gallic acid (12), ethyl gallate (13), chrysophanol (14), D-1-O-methyl-inositol (15), and hexadecanoic acid (16) based on their spectral data and physico-chemical properties. Compound 1 is an undescribed compound, of which its absolute configurations were determined by Mosher and ROESY methods; all the compounds except 10, 11 and 14 were isolated from Illigera genus for the first time. Compared with the positive control indomethacin, compounds 4-6, 8 and 9 inhibited significantly against the NO production in LPS-induced RAW 264.7 cells.

Phytochemical analysis and biological activities of ethanolic extract of Curcuma longa rhizome / Análise fitoquímica e atividades biológicas do extrato etanólico do rizoma de Curcuma longa

Abstract Curcuma longa is an important dietary plant which possess several pharmacological activities, including antioxidant, antimicrobial, anti-inflamatory, anticancer and anti clotting etc. The aim of the present study was to determine the phenolic profile of Curcuma longa and in vitro antioxidant and antidiabetic activities. In HPLC chromatogram of Curcuma longa rhizome extract 15 phenolic compounds were identified namely Digalloyl-hexoside, Caffeic acid hexoside, Curdione, Coumaric, Caffeic acid, Sinapic acid, Qurecetin-3-D-galactoside, Casuarinin, Bisdemethoxycurcumin, Curcuminol, Demethoxycurcumin, and Isorhamnetin, Valoneic acid bilactone, Curcumin, Curcumin-O-glucuronide respectively. The ethanolic extract displayed an IC50 value of 37.1±0.3 µg/ml against alpha glucosidase. The IC50 value of DPPH radical scavenging activity was 27.2 ± 1.1 μg/mL. It is concluded that ethanolic extract of Curcuma long is rich source of curcumin and contain several important phenolics. The in vitro antioxidant and alpha glucosidase inhibitory effect of the plant justifies its popular use in traditional medicine.

Resumo A Curcuma longa é uma importante planta presente na dieta da população, pois possui diversas atividades farmacológicas, incluindo antioxidante, antimicrobiana, anti-inflamatória, anticancerígena, anticoagulante etc. O objetivo do presente estudo foi elucidar o perfil fenólico da Curcuma longa e determinar as atividades antioxidante e antidiabética in vitro do extrato. No cromatograma por HPLC do extrato de rizoma de Curcuma longa, foram identificados 15 compostos fenólicos: digaloil-hexosídeo, hexosídeo de ácido cafeico, curdiona, cumárico, ácido cafeico, ácido sinápico, quercetina-3-D-galactosídeo, casuarinina, bisdemetoxicurcumina, curcuminol, demetoxicurcumina, isoramnetina, bilactona de ácido valônico, curcumina e curcumina-O-glicuronídeo. O extrato etanólico apresentou um valor de IC50 de 37,1 ± 0,3 µg / mL em relação à alfa-glucosidase. O valor de IC50 da atividade de eliminação de radicais DPPH foi de 27,2 ± 1,1 μg / mL. Conclui-se que o extrato etanólico de Curcuma longa é uma rica fonte de curcumina e contém várias substâncias fenólicas importantes. O efeito antioxidante in vitro e inibidor da alfa-glucosidase da planta justifica seu uso popular na medicina tradicional.

Chemical evaluation and anticholinesterase activity of Hippeastrum puniceum (Lam. ) Kuntz bulbs (Amaryllidaceae)

Hippeastrum puniceum is a species that belongs to the Amaryllidaceae family. A particular characteristic of this family is the consistent and very specific presence of isoquinoline alkaloids, which have demonstrated a wide range of biological activities such as antioxidant, antiviral, antifungal, antiparasitic, and acetylcholinesterase inhibitory activity, among others. In the present work, fifteen alkaloids were identified from the bulbs of Hippeastrum puniceum (Lam.) Kuntz using a GC-MS approach. The alkaloids 9-O-demethyllycoramine, 9-demethyl-2α-hydroxyhomolycorine, lycorine and tazettine were isolated through chromatographic techniques. The typical Amaryllidaceae alkaloids lycorine and tazettine, along with the crude and ethyl acetate extract from bulbs of the species were evaluated for their inhibitory potential on α-amylase, α-glucosidase, tyrosinase and acetylcholinesterase activity. Although no significant inhibition activity was observed against α-amylase, α-glucosidase and tyrosinase from the tested samples, the crude and ethyl acetate extracts showed remarkable acetylcholinesterase inhibitory activity. The biological activity results that correlated to the alkaloid chemical profile by GC-MS are discussed herein. Therefore, this study contributed to the knowledge of the chemical and biological properties of Hippeastrum puniceum (Lam.) and can subsidize future studies of this species

New oligomeric neolignans from the leaves of Magnolia officinalis var. biloba / 中国天然药物

Six new oligomeric neolignans including two trimeric neolignans (1 and 2) and four dimeric neolignans (3-6) were isolated from the leaves of Magnolia officinalis var. biloba. Their structures were determined based on HR-ESIMS and NMR data, as well as electronic circular dichroism (ECD) calculations. Compound 1 is formed from two obovatol moieties directly linked to an aromatic ring of the remaining obovatol moiety, which is an unprecedented type of linkage between monomers. All isolates were assessed for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophage cells. Compounds 1 and 3 showed significantly inhibitory activities with IC

Bioactive sesquineolignans from the twigs of Litsea cubeba / 中国天然药物

In a continuing search for biological natural products with structure diversity from traditional Chinese herbs, five new sesquineolignans (1-5) were isolated from an ethyl acetate extract of the twigs of Litsea cubeba. Their structures were elucidated based on MS, 1D and 2D NMR spectroscopic data, as well as experimental electronic circular dichroism (ECD) spectra. Compounds 1-5 showed moderate inhibitory effects against LPS-induced NO production in RAW264.7 macrophages, with IC

One new coumarin from seeds of Herpetospermum pedunculosum / 中国中药杂志

This paper aims to investigate the chemical constituents of the seeds of Herpetospermum pedunculosum. One new coumarin and two known lignans were isolated from the ethanolic extract of the seeds of H. pedunculosum with thin layer chromatography(TLC), silica gel column chromatography, Sephedax LH-20 chromatography, Semi-preparative high performance liquid chromatography and recrystallization, etc. Their structures were elucidated as herpetolide H(1), phyllanglaucin B(2), and buddlenol E(3) by analysis of their physicochemical properties and spectral data. Among them, compound 1 was a new compound, and compounds 2 and 3 were isolated from this genus for the first time. In vitro anti-inflammatory activity test showed that herpetolide H had certain NO inhibitory activity for LPS-induced RAW 264.7 cells, with its IC_(50) value of(46.57±3.28) μmol·L~(-1).

Synthesis and Antitumor Activities of N-hydroxy-5-(3-substituted ureido)-1H-indole-2-carboxamide Derivatives / 中国药学杂志

OBJECTIVE: To design and synthesize N-hydroxy-5-(3-substituted urea)-1H-indole-2-amide derivatives and investigate their anti-tumor activity in vitro. METHODS: A series of new N-hydroxy-5-(3-substituted ureido)-1H-indole-2-carboxamide derivatives (7a-7n)were designed and prepared from p-nitrophenylhydrazine and ethyl pyruvate. Their antitumor activities against Hela (breast cancer) lines, cervical cancer cell (MCF7) and human hepatoma cell lines (HepG2) were evaluated by methyl thiazolyl (MTT) method. RESULTS: Target compounds indicated certain antitumor activities, especially compound 7h showed the strongest cytotoxicity to Hela cells with a half inhibition concentration (IC50) of 7.31 μmol•L-1. CONCLUSION: The series of compounds show preferable antitumor activities, which are worthy of further study.

Study on apoptosis mechanism of leukemia cells induced by bisindolylmaleimide derivative L6 / 中草药

Objective: To investigate the effect of bisindolylmaleimide derivative L6 on inducing apoptosis of leukemia cells and its molecular mechanism. Methods: MTT assay was used to determinate the killing effect of L6 on HELL, K562, and KG1a cells. Flow cytometry was used to detect the effects of L6 on apoptosis, cell cycle, and differentiation of HEL cells. Western blotting was used to detect the expression of apoptosis-related protein. Finally, the effect of L6 on leukemia mouse was studied in vivo. Results: MTT assay showed that L6 had a stronger inhibitory activity against HEL, K562, and KG1a cell lines than the positive control PKC412 compound, with IC50 of (0.05 ± 0.03), (0.32 ± 0.01), and (0.19 ± 0.10) μmol/L, respectively. L6 could induce the apoptosis, G2/M arrest, megakaryocyte differentiation of HEL cells with a dose effect. Western blotting revealed that L6 mainly performed apoptosis by activating Caspase-3, which is an apoptotic executive protein. Hematoxylin-eosin (HE) staining of liver tissue of mice showed a reduction in HEL cell infiltration, but the more significant reduction in group L6 was observed, indicating that L6 could delay the metastasis of leukemia, and its effect was better than that of PKC412. Conclusion: Bisindolylmaleimide derivative L6 has a strong anti-leukemia activity, providing new hope for the development of new leukemia drugs.

Secondary metabolites of endophytic fungus Aspergillus ochraceus SX-C7 from Selaginella stauntoniana / 中草药

Objective: To study the secondary metabolites of endophytic fungus Aspergillus ochraceus SX-C7 from Setaginella stauntoniana. Methods: The compounds were isolated and purified by silica gel, Sephadex LH-20, C-18 reversed phase column chromatography, and their structures were identified by MS and NMR analyses. Antibacterial activity and inhibitory activity against acetylcholinesterase were studied by doubling dilution and Ellman methods. Results: Ten known compounds were isolated from the secondary metabolites of A. ochrateus SX-C7, and identified as: semivioxanthin (1), 6-hydroxy-p-menth-4 (5)-en-3-one (2), flavacol (3), magnolin (4), preussin B (5), circumdatins D (6), isofucosterol (7), sclerotiamide (8), 3β-hydroxyergosta-8,24(28)-dien-7-one (9), and 3-O-β-D-glucopyranosyl stigmasta-5(6),24(28)-diene (10). Conclusion: Compounds 1, 2, 4, 7, and 10 were isolated from A. ochraceus SX-C7 for the first time. The results of the bioactivity assay showed that compound 10 possessed obvious inhibitory activity against Bacillus subtilis with a MIC value of 2 μg/mL, which was at the same grade with positive control. Compound 1 exhibited potent inhibitory activity against acetylcholinesterase with an inhibitory rate of 62.3% (the final concentration was 50 μmol/L.

Study on in vitro Inhibitory Activity of the Extracts from 9 Kinds of TCM for Dredging Collaterals and Dispelling Wind on Xanthine Oxidase / 中国药房

OBJECTIVE：To study in vi tro inhibitory act ivities of 9 kinds of TCM for dredging collaterals and dispelling wind on xanthine oxidase （XO），and to screen TCM with outstanding activity. METHODS ：Using xanthine as substrate and xanthinase as reaction enzyme ，allopurinol as positive control ，with water extract and methanol extract （hereinafter referred to as “ethanol extract”）from the stem and leaves of Hedera nepalensis ，the whole plant of Piper wallichii ，the fruits of Rubus corchorifolius ，the root of Caragana sinica ，the root of Wisteria sinensis ，the root of Rubus crataegifolius ，the bark of Catalpa ovata ，the root of Campsis grandiflora ，the stem of P. hancei （hereinafter referred to by plant name ）and petroleum ether ，dichloromethane，ethyl acetate，n-butanol and water fraction of active extract as the objects ，inhibition rate of each sample to XO was detected by spectrophotometry；IC50values were calculated with Graphpad prism 6.0 software to screen active extract/fraction. Double reciprocal method was used to determine the type of enzyme inhibition. RESULTS ：Among 9 kinds of TCM and 18 kinds of the extracts ，the inhibitory rates to XO of 500 μg/mL extracts from each TCM（except for ethanol extract of P. wallichii ），250 μg/mL water extract and ethanol extract of H. nepalensis ，P. wallichii ，R. corchorifolius and P. hancei ，250 μg/mL water extract of C. ovata ，250 μ g/mL ethanol extract of C. sinica ，R. crataegifolius and C. grandiflora ，125 μ g/mL ethanol extract of C. sinica and R. crataegifolius，62.5 μg/mL ethanol extract of C. sinica were more than 50％. The IC 50 value of the ethanol extract from C. sinica was 43.43 μg/mL，which was lower than the extracts of other TCM ，and which was the active extract. The IC 50 values of petroleum ether，dichloromethane，ethyl acetate ，n-butanol and water fracti on of ethanol extract from C. sinica were ＞200，193.35，7.67， 14.80 and ＞200 μg/mL，respectively. The IC 50 value of ethyl XO was competitive-noncompetitive inhibition ， which was different from competi tive inhibition of positive control. CONCLUSIONS：The ethanol extracts of C. sinica ，R. crataegifolius ，P. wallichii ，R. corchorifolius ，P. hancei ，H. nepalensis and the water extracts of H. nepalensis ，P. wallichii ，C. ovata show certain inhibitory activity in vitro to XO ，especially ethanol extract of C. sinica . The ethyl acetate fraction of the ethanol extract of C. sinica has similar inhibitory activity to allopurinol but their inhibition types are different.

Study on the secondary metabolites of grasshopper-derived fungi Arthrinium sp. NF2410 / 中国天然药物

Two new 2-carboxymethyl-3-hexyl-maleic anhydride derivatives, arthrianhydride A (1) and B (2), along with three known compounds 3-5, were isolated from the fermentation broth of a grasshopper-associated fungus Arthrinium sp. NF2410. The structures of new compounds 1 and 2 were determined based on the analysis of the HR-ESI-MS and NMR spectroscopic data. Furthermore, compounds 1 and 2 were evaluated on inhibitory activity against the enzyme SHP2 and both of them showed moderate inhibitory activity against SHP2.

New furo3,2-hisochroman from the mangrove endophytic fungus Aspergillus sp. 085242 / 中国天然药物

Four new compounds, asperisocoumarin G (1), asperisocoumarin H (2), (±)-asperisocoumarin I [(±)-3], along with the known pergillin (4) and penicisochroman L (5) were isolated from a mangrove endophytic fungus Aspergillus sp. 085242 by further chemical investigation. The structures of the new compounds, including their absolute configurations, were established by analysis of HR-ESI-MS and NMR spectroscopic data, and ECD calculation. Asperisocoumarins G-I (1-3) were new isocoumarins belonging to the class of furo[3, 2-h]isocoumarins which are rarely found in natural sources. All of the isolated compounds were evaluated for their α-glucosidase inhibitory effects, and compounds 1 and 4 showed moderate α-glucosidase inhibitory activity, respectively. In an antimicrobial test, the racemate of 3 showed antibacterial activity against Salmonella.

Selective BuChE inhibitory activity, chemical composition, and enantiomer content of the volatile oil from the Ecuadorian plant Clinopodium brownei

ABSTRACT This paper describes the chemical composition and the enantiomer content of the volatile oil hydrodistilled from Clinopodium brownei (Sw.) Kuntze, Lamiaceae. The plant was collected in the South of Ecuador. Thirty one components were identified by GC-MS, which accounted for the 96.15% of the volatile oil. The major components were pulegone (48.44%), menthone (34.55%) and β-acorenol (3.41%). Oxygenated monoterpenes (86.06%), followed by oxygenated sesquiterpenes (5.36%) constituted the most abundant fractions. The enantiomeric compositions of β-pinene, sabinene, 3-octanol, menthone, pulegone and menthyl acetate were determined by enantioselective GC-MS. (-)-Menthone showed the highest enantiomeric excess (ee = 83.4%). In in vitro tests, the volatile oil showed high selective inhibitory activity for butyrylcholinesterase with an IC50, 13.4 ± 1.8 µg/ml. In contrast, it was weakly active against acetylcholinesterase with an IC50 >250 µg/ml.

Thai pigmented rice bran extracts inhibit production of superoxide, nitric oxide radicals and inducible nitric oxide synthase in cellular models

Objective: To study the inhibitory effect of rice bran extracts of Thai black Kam Muang and red Hawm Dawk Mali Deang on oxidative stress factors including superoxide (O

Chemical Constituents of Hypericum uralum and the Analgesic and Antimalarial Activities / 中国药学杂志

OBJECTIVE: To study the chemical constituents of Hypericum uralum were isolated and identified and test the analgesic activity and β-hematin formation inhibitory activity of some selected compounds. METHODS: The compounds were isolated and purified by column chromatography padded with the separating material including silica gel and Sephadex LH-20, and their structures were elucidated based on the analyses of modern spectrum technology. Analgesic and antimalarial activities of selected compounds from H. uralum were evaluated by acetic acid-induced writhing, hot water tail-flick test in mice, and β-hematin formation inhibition method, respectively. RESULTS: Thirteen compounds were isolated from ethyl acetate portion of 95% ethanol extract of H. uralum and identified as (-)-eriodictyol (1), 3,4,5-trihydroxyxanthone (2), 1,7-dihydroxyxanthone (3), 4-hydroxy-2,3-dimethoxyxanthone (4), toxyloxanthone B (5), 1,3,6,7-tetrahydroxyxanthone (6), 2,3-dimethoxyxanthone (7), 1,5,6-trihydroxy-3-methoxyxanthone (8), hyperielliptone HD (9), 3,3′,4,4′-tetrahydroxybiphenyl (10), shikimic acid (11), quercetin-3-O-(4″-methoxy)-α-L-rahmnopyranosyl (12), and proanthocyanidin A-2 (13). The analgesic activity test indicated that compounds 3 and 12 had certain peripheral analgesic activity, while compound 1 exhibited strong β-hematin formation inhibitory activity. CONCLUSION: All the compounds are obtained from this plant for the first time.The analgesic and antimalarial activities of H. uralum have corresponding material basis.

Chemical constituents and their bioactivities from seeds of Clausena lansium / 中草药

Objective To study the chemical constituents and their biological activities of the seeds of Clausena lansium. Methods The compounds were isolated by various column chromatographic techniques including silica gel, Sephadex LH-20, semi-preparative HPLC, et al., and their structures were identified through a combined analysis of physicochemical properties, as well as NMR and MS data. The in vitro α-glucosidase inhibitory activity and nematicidal activity against Panagrellus redivivusl were screened by PNPG and Berman funnel methods, respectively. Results Eleven compounds were isolated and identified as (4R*,6R*)-6-hydroxypiperitone (1), (4S*,6R*)-6-hydroxypiperitone (2), (1S*,2S*,4R*)-1-methyl-4-(prop-l-en-2-yl) cyclohexane-1,2-diol (3), subamone (4), methyl (1R*,2R*,2’Z)-2-(5’-hydroxy-pent-2’-enyl)-3-oxo-cyclopentane acetate (5), 5-hydroxy-4-phenyl-5H-furan-2-one (6), loliolide (7), xylogranatinin (8), 2,6-dihydroxyhumula-3(12),7(13),9(E)-triene (9), xanthoxol (10), and ligballinol (11). Conclusion Compounds 1-8 are isolated from the genus for the first time, and compound 9 is first isolated from this species. Compound 8 showed strong α-glucosidase inhibitory activity, and compound 5 exhibited potent nematicidal activity.

Metabolites from Cercospora lagenariae MT-45, an endophytic fungus isolated from Huperzia serrata / 中草药

Objective: To investigate the chemical metabolites from Cercospora lagenariae MT-45, an endophytic fungus isolated from Huperzia serrata (Thunb.) Trev. Methods: The compounds were isolated and purified by using silica gel column chromatography and semi-preparative liquid chromatography. The structures were established using physicochemical properties and MS and NMR. The anti-inflammatory activities of all the isolates were also preliminarily investigated by using in vitro model. Results: Nine polyketide derivatives including cercolagenlic acid A (1), alternariol (2), alternariol 9-methyl ether (3), (+)-nigrosporaol A (4), alternarienonic acid B (5), 2-methyl-5-carboxymethyl-7-hydroxychromone (6), 2,5-dimethyl-7-hydroxychromone (7), 1-deoxy- rubralactone (8), and (-)-alternarlactam (9) were isolated from C. lagenariae MT-45 fermented on brown rice solids. Conclusion: Compound 1 is a new compound, and compound 6 can exhibit a certain inhibition on the nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells with an IC50 value of (57.5 ± 1.2) μmol/L.