RESUMO
A simple and effective method was established for separation and characterization of flavonoid constituents in Radix Astragali (RA) by combination of ultra-high-pressure liquid chromatography with LTQ-Orbitrap tandem mass spectrometry (u-HPLC-LTQ-Orbitrap-MS(n)). For three major structural types of flavonoids, the proposed fragmentation pathways and major diagnostic fragment ions of isoflavones, pterocarpans and isoflavans were investigated to trace isoflavonoid derivatives in crude plant extracts. Based on the systematic identification strategy, 48 constituents were rapidly detected and characterized or tentatively identified, many of which were first reported in RA. The u-PHLC-LTQ-Orbitrap MS(n) platform was proved as an effective tool for rapid qualitative analysis of secondary metabolite productions from natural resources.
Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Flavonoides/análise , Espectrometria de Massas em Tandem/métodos , Astragalus propinquus , Flavonoides/químicaRESUMO
AIM: Huperzine A isolated from the Chinese herb Huperzia serrata (Thunb) Trev is a novel reversible and selective AChE inhibitor. The aim of this study was to evaluate the pharmacokinetics and tolerance of single and multiple doses of ZT-1, a novel analogue of huperzine A, in healthy Chinese subjects. METHODS: This was a double-blinded, placebo-controlled, randomized, single- and multiple-dose study. For the single-dose study, 9 subjects were randomly divided into 3 groups receiving ZT-1 (0.5, 0.75 or 1 mg, po) according to a Three-way Latin Square Design. For the multiple-dose study, 9 subjects receiving ZT-1 (0.75 mg/d, po) for 8 consecutive days. In the tolerance study, 40 subjects were randomly divided into 5 groups receiving a single dose of ZT-1 (0.5, 0.75, 1, 1.25 or 1.5 mg, po). Plasma and urine concentrations of ZT-1 and Hup A were determined using LC-MS/MS. Pharmacokinetic parameters, including Cmax, AUC0-72 h and AUC0-∞ were calculated. Tolerance assessments were conducted throughout the study. RESULTS: ZT-1 was rapidly absorbed and converted into huperzine A, thus the plasma and urine concentrations of ZT-1 were below the limit of quantification (<0.05 ng/mL). After single-dose administration of ZT-1, the mean tmax of huperzine A was 0.76-0.82 h; the AUC0-72 h and Cmax of huperzine A showed approximately dose-proportional increase over the dose range of 0.5-1 mg. After the multiple-dose administration of ZT-1, a steady-state level of huperzine A was achieved within 2 d. No serious adverse events were observed. CONCLUSION: ZT-1 is a pro-drug that is rapidly absorbed and converted into huperzine A, and ZT-1 is well tolerated in healthy Chinese volunteers.
Assuntos
Alcaloides/farmacocinética , Doença de Alzheimer , Inibidores da Colinesterase/farmacocinética , Pró-Fármacos/farmacocinética , Sesquiterpenos/farmacocinética , Alcaloides/administração & dosagem , Alcaloides/efeitos adversos , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/metabolismo , Inibidores da Colinesterase/administração & dosagem , Inibidores da Colinesterase/efeitos adversos , Estudos Cross-Over , Método Duplo-Cego , Humanos , Masculino , Pró-Fármacos/administração & dosagem , Pró-Fármacos/efeitos adversos , Sesquiterpenos/administração & dosagem , Sesquiterpenos/efeitos adversos , Resultado do Tratamento , Adulto JovemRESUMO
Seven new diglycosidic constituents, named pteleifosides A-G (1-7), along with ten known glycosides, were isolated from the roots and rhizomes of Melicope pteleifolia (Champ. ex Benth.) T. Hartley. The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry.
Assuntos
Glicosídeos/isolamento & purificação , Raízes de Plantas/química , Rizoma/química , Rutaceae/química , Glicosídeos/química , Espectrometria de Massas , Conformação Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Two new arylnaphthalene lignan glycosides, named reticulatusides A (1) and B (2), together with eight known compounds were isolated from the 95% EtOH extract of the whole plant of Phyllanthus reticulatus. The structures of the new compounds were elucidated by spectroscopic methods.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lignanas/isolamento & purificação , Naftalenos/isolamento & purificação , Phyllanthus/química , Medicamentos de Ervas Chinesas/química , Glicosídeos/química , Lignanas/química , Estrutura Molecular , Naftalenos/química , Ressonância Magnética Nuclear BiomolecularRESUMO
A method for qualitative analysis of constituents in Panax notoginseng by UPLC-LTQ-Orbitrap mass spectrometry was established. Based on the high-resolution mass information, MS/MS fragmentation behaviors and chemical components from literatures, 43 compounds were identified or tentatively characterized. New type saponin aglycone, combined with malonyl-substituted and acetyl-substituted saponins were discovered and plausibly identified in this study. This work could be helpful for the quality control and further phytochemical studies of Panax notoginseng, and provided a good example for the analysis of chemical constituents in traditional Chinese medicine.
Assuntos
Ginsenosídeos/análise , Panax notoginseng/química , Saponinas/análise , Espectrometria de Massas em Tandem , Cromatografia Líquida de Alta Pressão , Análise de Fourier , Raízes de Plantas/química , Plantas Medicinais/química , Controle de Qualidade , Saponinas/classificaçãoRESUMO
OBJECTIVE: To study the chemical constituents of the ethyl acetate extract from Blumea aromatica. METHODS: Column chromatographic techniques were used for the isolation and purification. Spectroscopic techniques were used for the identification of structures. RESULTS: Seven compounds were isolated from the ethyl acetate extract of 80% alcohol extract of the whole plant, and their structures were identified as xanthoxylin(1), dibutyl phthalate(2), luteolin-3',4',7-trimethyl ether(3), rubiadin(4), eriodictyol(5), kaempherol(6), luteolin 7,3'-dimethyl ether(7). CONCLUSION: All the compounds are isolated from this plant for the first time. Among them, compounds 2,4 and 7 are isolated from this genus for the first time.
Assuntos
Antraquinonas/isolamento & purificação , Asteraceae/química , Dibutilftalato/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Luteolina/isolamento & purificação , Acetatos , Antraquinonas/química , Cromatografia Líquida de Alta Pressão , Dibutilftalato/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Quempferóis/química , Quempferóis/isolamento & purificação , Luteolina/química , Estrutura Molecular , Solventes/químicaRESUMO
Two new lignans (R-biar)-12-angeloyloxy-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7-dibenzo[a,c]cyclooctenol (1) and (R-biar)-12-benzoyloxy-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7-dibenzo[a,c]cyclooctenol (2) were isolated from the stems of Celastrus flagellaris Rupr. Their structures were elucidated on the basis of spectroscopic methods including HR-EI-MS, 1D and 2D NMR, HMQC, NOESY, and CD.
Assuntos
Celastrus/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Lignanas/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Lignanas/química , Estrutura Molecular , Caules de Planta/químicaRESUMO
A rapid and effective method was developed for separation and identification of diester-diterpenoid alkaloids (DDA) in the roots of Aconitum carmichaeli by ultra-high-pressure liquid chromatography coupled with high resolution LTQ-Orbitrap tandem mass spectrometry (UHPLC-LTQ-Orbitrap-MS(n)). According to accurate mass measurement and the characteristic neutral loss filtering strategy, a total of 42 diester-diterpenoid alkaloids (DDA) were rapidly detected and characterized or tentatively identified. Meanwhile, the proposed fragmentation pathways and the major diagnostic fragment ions of aconitine, mesaconitine and hypaconitine were investigated to trace DDA derivatives in crude plant extracts. 23 potential new compounds were successfully screened and characterized in Aconitum carmichaeli, including 16 short chain fatty acyls DDA, 4 N-dealkyl DDA and several isomers of aconitine, mesaconitine and hypaconitine.
Assuntos
Aconitum/química , Alcaloides/análise , Diterpenos/análise , Ésteres/análise , Filtração/métodos , Raízes de Plantas/química , Espectrometria de Massas em Tandem/métodos , Aconitina/análogos & derivados , Aconitina/análise , Aconitina/química , Alcaloides/química , Cromatografia Líquida de Alta Pressão , Diterpenos/química , Ésteres/química , Ácidos Graxos/análise , Isomerismo , Padrões de ReferênciaRESUMO
Lamiolactone (1), a new iridoid lactone, together with five known iridoids, were isolated from the 95% EtOH extract of the roots of Lamiophlomis rotata. The structure of 1 was elucidated to be methyl antirrhinolide-4-carboxylate on the basis of spectroscopic analysis.
Assuntos
Iridoides/química , Lactonas/química , Lamiaceae/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Raízes de Plantas/químicaRESUMO
C9-iridoid glycosides, wallichiisides A-C, and four dimers, wallichiisides D-G, together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Their structures were elucidated by spectroscopic methods and comparison with literature values. Four of these compounds showed moderate DPPH free radical scavenging activity.
Assuntos
Glicosídeos Iridoides/química , Lamiaceae/química , Extratos Vegetais/química , Dimerização , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Glicosídeos Iridoides/isolamento & purificação , Medicina Tradicional Tibetana , Estrutura Molecular , Plantas Medicinais/química , TibetRESUMO
A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC(50)=0.4 and <1 µM, respectively) and low cytotoxicity (CC(50)=40.6 and >25 µM, respectively).
Assuntos
Antivirais/química , Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Hepatite B/tratamento farmacológico , Triptaminas/química , Triptaminas/farmacologia , Sobrevivência Celular/efeitos dos fármacos , DNA Viral/metabolismo , Células Hep G2 , Humanos , Relação Estrutura-AtividadeRESUMO
A new dammarane-type triterpenoid saponin, (20R)-ginsenoside ST(2) (1), along with five known saponins was isolated from the hongshen extract of Shenmai injection. The structure of 1 was elucidated to be (20R)-dammar-23(E)-ene-3ß,6α,12ß,20,25-pentol 6-O-ß-D-glucopyranoside by means of spectroscopic methods.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Ginsenosídeos/isolamento & purificação , Panax/química , Plantas Medicinais/química , Triterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Ginsenosídeos/química , Ginsenosídeos/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacologia , DamaranosRESUMO
A new lycopodane-type Lycopodium alkaloid, 6α-hydroxy-5,15-oxide-lycopodane (1), and seven known alkaloids were isolated from the whole plants of Huperzia serrata. Their structures were elucidated by means of spectroscopic methods. 12-Deoxyhuperzine O (2) was reported as a naturally occurring alkaloid for the first time, and showed an antagonist effect on the N-methyl-d-aspartate receptor with an IC(50) value of 0.92 µM.
Assuntos
Alcaloides/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Huperzia/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Córtex Cerebral/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ratos , Ratos Sprague-Dawley , Receptores de N-Metil-D-Aspartato/antagonistas & inibidores , Membranas Sinápticas/efeitos dos fármacosRESUMO
A new cinnamic acid-derived bisamide 1 and a new oplopanone-type sesquiterpenoid diglycoside 2, together with 11 known compounds, were isolated from the 95% ethanolic extract of the leaves of Aglaia perviridis. Their structures were elucidated by chemical and spectroscopic methods.
Assuntos
Aglaia/química , Cinamatos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Cinamatos/química , Medicamentos de Ervas Chinesas/química , Glicosídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Sesquiterpenos/química , EstereoisomerismoRESUMO
OBJECTIVE: To study the chemical constituents of the peels collected from Citrus changshan-huyou Y. B. Chang, and further screen the bioactive components as the lead structures. METHODS: These compounds were isolated by repeated flash column chromatography on silica gel and Sephadex LH-20. The structures of isolated compounds were elucidated by using IR, EIMS, and NMR analyses. RESULTS: One novel compound along with nine known compounds were obtained and identified as huyoujiasu(I), 3-hydroxy-4-methoxybenzoic acid(II), 3, 4-dihydroxybenzoic acid(III), fatty acid(IV), glyceride(V), 6, 7-dimethoxycoumarin(VI), 6', 7'-dihydroxybergamottin(VII), daucossterol A(VIII), daucossterol B(IX) and huyou-triterpenoid(X). CONCLUSION: One new compound, Huyoujiasu, was obtained from these peels by repeated column chromatography, and the other known compounds were isolated from this fruit for the first time as well.
Assuntos
Citrus/química , Frutas/química , Hidroxibenzoatos/isolamento & purificação , Fenóis/isolamento & purificação , Cromatografia/métodos , Citrus/classificação , Cumarínicos/química , Cumarínicos/isolamento & purificação , Hidroxibenzoatos/química , Fenóis/química , Sitosteroides/química , Sitosteroides/isolamento & purificaçãoRESUMO
Two new Lycopodium alkaloids, N-oxidehuperzine E (1) and N-oxidehuperzine F (2), along with two known alkaloids, huperzines E (3) and F (4), were isolated from Huperzia serrata (Thunb.) Trev. Their structures were elucidated by spectroscopic and chemical transformations.
Assuntos
Alcaloides/química , Huperzia/química , Extratos Vegetais/química , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Callianthones A ( 1) and B ( 2), a pair of new isomeric alpha-tetralones, together with a known alpha-tetralone ( 3) and four known flavonoids ( 4 - 7) were isolated from the 50 % EtOH extract of Pyrola calliantha. The structures and absolute configurations of the two new isomers were established to be (2 S,4 R) - and (2 S,4 S)-2,4-dihydroxy-2,7-dimethyl-3,4-dihydronaphthalen-1(2 H)-one ( 1 and 2, respectively) on the basis of spectral analysis, including 2 D NMR, model studies, and CD spectra.
Assuntos
Extratos Vegetais/isolamento & purificação , Pyrola/química , Tetralonas/isolamento & purificação , Isomerismo , Modelos Estruturais , Estrutura Molecular , Extratos Vegetais/química , Tetralonas/químicaRESUMO
"Danshen" has been used for the treatment of various cardiovascular diseases in the People's Republic of China for many years. Two different forms of "Danshen" exist, with the roots of Salvia miltiorrhiza being the traditional form and the roots of Salvia przewalskii being a surrogate used in the western areas of mainland China. The most abundant lipophilic diterpene quinones present in S. miltiorrhiza and S. przewalskii roots, tanshinone IIA (1) and cryptotanshinone (2), inhibited contraction of the isolated porcine coronary artery to the thromboxane A(2) analogue, U46619. Przewaquinone A (3), a lipophilic diterpene quinone present only in S. przewalskii, induced a similar but greater inhibitory action on vascular contraction than 1 and 2. This effect of 3 was endothelium-independent and reversible. The present results suggest that 3 is more potent than 1 and 2 and may contribute to a great extent to the ability of S. przewalskii roots to inhibit vascular contractions.
Assuntos
Abietanos/farmacologia , Diterpenos/farmacologia , Medicamentos de Ervas Chinesas/uso terapêutico , Lipídeos/química , Medicina Tradicional Chinesa , Fenantrenos/farmacologia , Fenantrolinas/uso terapêutico , Quinonas/farmacologia , Salvia miltiorrhiza/química , Animais , Vasos Coronários/efeitos dos fármacos , Humanos , Estrutura Molecular , Raízes de Plantas/química , Sus scrofaRESUMO
OBJECTIVE: To study the effects of soil microbes of habitats, endophytic fungi and root surface fungi of Huperzia serrata on rooting rate of the cuttings and on several physiological and biochemical indexes. METHOD: The cuttings of H. serrata were planted on soil I of primary habitat, the soil II had been inoculated endophytic fungi and root surface fungi, the soil III had been auto-claved, rooting rate was examined, and soluble protein and soluble sugar contents, activities of PPO and POD, flavonoids and huperzine A contents were determined. RESULT: Compared with the H. serrata that were planted on soil III, soil I and soil II were found to increase the rooting rate by 10% and 16%, soil II increased the soluble protein contents of stem of H. serrata (P < 0.05), Soil I increased the soluble sugar contents of leaves and stem of H. serrata (P < 0.05), soil I and Soil II increased the flavonoids contents of H. serrata (P < 0.05). CONCLUSION: Soil microbes from primary habitat, endophytic fungi and root surface fungi promote rooting, they also increase plant metabolism level of H. serrata.
Assuntos
Huperzia/crescimento & desenvolvimento , Huperzia/microbiologia , Raízes de Plantas/crescimento & desenvolvimento , Raízes de Plantas/microbiologia , Metabolismo dos Carboidratos , Flavonoides/metabolismo , Huperzia/metabolismo , Proteínas de Plantas/química , Proteínas de Plantas/metabolismo , Raízes de Plantas/metabolismo , Microbiologia do Solo , SolubilidadeRESUMO
Two new pregnanes, 2alpha,3alpha,20-trihydroxy-16beta-acetoxy-20(R)-pregnane (1) and 2alpha,3alpha,15beta-trihydroxy-16beta-acetoxy-pregnane-20(R)-methacrylate (2), along with five known compounds, were isolated from the ethanolic extract of the twigs of Aglaia perviridis Hiern using chromatographic methods. The structures of 1 and 2 were elucidated on the basis of spectral data.