RESUMO
Dracaena cambodiana Pierre ex Gagnep. is well known as a medicinal plant and widely distributed in Vietnam. Phytochemical investigation on the trunks of D. cambodiana lead to the isolation of four undescribed compounds (1-4) together with seven known ones (5-11). Their structures were determined to be pennogenin-24-yl-O-ß-D-glucopyranoside (1), 17α-hydroxycambodianoside C (2), (25R)-27-hydroxypenogenin 3-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (3), (3ß,25R)-17α,22α-dihydroxy-furost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (4), dracagenin A (5), 1-O-ß-D-glucopyranosyl-2-hydroxy-4-allylbenzene (6), 1-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-2-hydroxy-allylbenzene (7), 2-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-1-hydroxy-allylbenzene (8), cinnamrutinoside A (9), icariside D1 (10), and seco-isolariciresinol 9-O-ß-glucopyranoside (11) by extensive spectroscopic investigation, HR-ESI-MS, 1D and 2D NMR spectra. The anti-inflammatory activity of the isolated compounds was evaluated on macrophages. Compounds 1-6 significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Among them, compound 1 showed the best inhibitory activity with an IC50 value of 8.90±0.56â µM.
Assuntos
Derivados de Alilbenzenos , Dracaena , Saponinas , Lipopolissacarídeos/farmacologia , Estrutura Molecular , Óxido Nítrico , Saponinas/farmacologia , Saponinas/química , Glucosídeos/química , Glucosídeos/farmacologiaRESUMO
Three previously undescribed compounds named rauvolphyllas A-C (1-3), along with thirteen known compounds, 18ß-hydroxy-3-epi-α-yohimbine (4), yohimbine (5), α-yohimbine (6), 17-epi-α-yohimbine (7), (E)-vallesiachotamine (8), (Z)-vallesiachotamine (9), 16S-E-isositsirikine (10), Nb -methylisoajimaline (11), Nb -methylajimaline (12), ajimaline (13), (+)-lyoniresinol 3α-O-ß-D-glucopyranoside (14), (+)-isolarisiresinol 3α-O-ß-D-glucopyranoside (15), and (-)-lyoniresinol 3α-O-ß-D-glucopyranoside (16) were isolated from the aerial parts of Rauvolfia tetraphylla L. Their chemical structures were elucidated based on the extensive spectroscopic interpretation of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configurations of 2 and 3 were determined by experimental ECD spectra. Compounds 5, 6, 7, and 11-13 exhibited nitric oxide production inhibition activity in LPS-activated RAW 264.7 cells with the IC50 values of 79.10, 44.34, 51.28, 33.54, 37.67, and 28.56â µM, respectively, compared to that of the positive control, dexamethasone, which showed IC50 value of 13.66â µM. The other isolates were inactive with IC50 values over 100â µM.
Assuntos
Alcaloides , Anisóis , Lignanas , Naftalenos , Rauwolfia , Animais , Camundongos , Lignanas/química , Células RAW 264.7 , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Alcaloides/análise , Espectroscopia de Ressonância Magnética , Componentes Aéreos da Planta/química , Ioimbina , Estrutura MolecularRESUMO
Four previously undescribed compounds named phyllancosides A and B (1 and 2), and phyllancochines A and B (3 and 4) together with ten known compounds (5-14) were isolated from the aerial parts of Phyllanthus cochinchinensis Spreng. Their chemical structures were elucidated on the basis of comprehensive analysis of IR, HR-ESI-MS, 1D and 2D NMR spectra. The absolute configurations of 1 and 2 were determined by electronic circular dichroism (ECD) spectra. Compounds 3, 4, and 10 showed antimicrobial activity against E. faecalis, S. aureus, and B. cereus with the MIC values in range of 32-256â µg/mL. Compound 11 inhibited E. faecalis and B. cereus, and 7 inhibited S. aureus with the MIC values in range of 64-128â µg/mL. In addition, compounds 1, 3, 4, 8, and 9 showed significantly NO production inhibitory activity in LPS activated RAW 264.7 cells with IC50 values ranging from 36.57 to 56.34â µM.
Assuntos
Anti-Infecciosos , Lipopolissacarídeos , Animais , Camundongos , Células RAW 264.7 , Estrutura Molecular , Lipopolissacarídeos/farmacologia , Staphylococcus aureus , Óxido Nítrico , Componentes Aéreos da Planta/química , Anti-Infecciosos/análiseRESUMO
Eight furostanol glycosides including five undescribed compounds, named tribufurostanosides A-E (1-5), and three known ones (6-8) were isolated from the fruits of Tribulus terrestris L. Their chemical structures were determined by the IR, HR-ESI-MS, 1D-, and 2D-NMR spectra. Furostanols 1-8 significantly inhibited nitric oxide production in LPS activated RAW 264.7â cells with IC50 values ranging from 14.2 to 64.7â µM, compared to that of the positive control compound, dexamethazone (IC50 13.6â µM).
RESUMO
In this study, two undescribed compounds (1 and 2), together with eight known compounds (3-10) were isolated from the aerial parts of Piper samentosum by various chromatography methods. Their chemical structures were determined to be 7'''-oxolyciumamide N (1), vitexin 2''-O-ß-D-(6'''-feruloyl)-glucopyranoside (2), 1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis-[2-(-hydroxyphenyl)ethyl]-2,3-napthalene dicarboamide (3), vitexin 6''-O-ß-D-glucopyranoside (4), vitexin 2''-O-α-L-rhamnopyranoside (5), methyl 2-hydroxybenzoate-2-O-ß-D-apiofuranosyl-(1â2)-O-ß-D-glucopyranoside (6), ficuside G (7), methyl 2-O-ß-D-glucopyranosylbenzoate (8), methyl 2,5-dihydroxybenzoate-5-O-ß-D-glucopyranoside (9), and 3,7-dimethyloct-1-ene-3,6,7-triol 6-O-ß-D-glucopyranoside (10) by spectroscopic data analysis including HR-ESI-MS, 1D-, and 2D-NMR spectra. Compoundsâ 1-5 inhibited nitric oxide production in LPS-stimulated RAW264.7 macrophages with the IC50 values of 27.62, 74.03, 38.54, 70.39, and 44.95â µM, respectively. The NMR data of 9 were firstly reported herein.
Assuntos
Flavonas , Glucosídeos , Lipopolissacarídeos , Óxido Nítrico , Piper , Componentes Aéreos da Planta , Células RAW 264.7 , Camundongos , Animais , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Lipopolissacarídeos/farmacologia , Lipopolissacarídeos/antagonistas & inibidores , Componentes Aéreos da Planta/química , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Glucosídeos/química , Piper/química , Flavonas/isolamento & purificação , Flavonas/farmacologia , Flavonas/química , Amidas/química , Amidas/farmacologia , Amidas/isolamento & purificação , Estrutura MolecularRESUMO
Phytochemical investigation of the methanol extract of the aerial parts of Lysimachia laxa led to the isolation of four new oleanane-type saponins, lysimosides A-D (1-4) and one known compound, lysimachigenoside B (5). Their structures were elucidated using a combination of HR-ESI-MS, 1D and 2D-NMR spectral data, chemical methods, and comparison with previous literature. The cytotoxic activity of these compounds was evaluated against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines. All compounds exhibited cytotoxic activity against A-549 and MCF-7 cell lines with IC50 values ranging from 6.1 to 16.0 µM, comparable to the positive control, mitoxantrone. Interestingly, oleanane-type saponins with an acetyl group (2-4) exhibited increased cytotoxic activities compared to those without an acetyl group (1).
RESUMO
Phytochemical study on the methanol extract of the stems of Tinospora crispa (L.) Hook.f. & Thomson led to the isolation of thirteen compounds including three undescribed cis-clerodane-type furanoditerpenoids (1-3) and ten known ones (4-13). Their chemical structures were determined by IR, HR-ESI-MS, 1D-, and 2D-NMR spectra. Compounds 2-6 and 8 inhibited moderately NO production in LPS activated RAW 264.7 cell with the IC50 values of 83.5, 57.6, 75.3, 78.1, and 74.7 µM, respectively.
RESUMO
Two undescribed triterpenes, syzyfolium A (1) and syzyfolium B (2), together with twelve known compounds, terminolic acid (3), actinidic acid (4), piscidinol A (5), threo-dihydroxydehydrodiconiferyl alcohol (6), lariciresinol-4-O-ß-D-glucoside (7), icariol A2 (8), 14ß,15ß-dihydroxyklaineanone (9), garcimangosone D (10), (+)-catechin (11), myricetin-3-O-α-L-rhamnopyranoside (12), quercitrin (13), and 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-ß-D-glucopyranoside (14) were isolated from the leaves of Syzygium myrsinifolium. Their chemical structures were determined by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 3 and 4 inhibited significantly α-glucosidase with IC50 values of 23.99 and 36.84, respectively, and compounds 1 and 2 inhibited significantly α-amylase with IC50 values of 35.48 and 43.65â µM, respectively.
Assuntos
Syzygium , Triterpenos , Syzygium/química , alfa-Glucosidases , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , alfa-Amilases , Inibidores de Glicosídeo Hidrolases/farmacologia , Inibidores de Glicosídeo Hidrolases/químicaRESUMO
Seven steroidal saponins including three new 16,23-cyclocholestanes (1-3) and one new pregane (4) were isolated from the roots of Dracaena cambodiana Pierre ex Gagnep. Their chemical structures were elucidated to be (23R,25R)-26-O-ß-D-glucopyranosyl-16,23-cyclocholesta-5,17(20)-dien-22-one-3ß,16α,26-triol-3-O-α-L-rhamnopyranosyl-(1â2)-[α-L-rhamnopyranosyl-(1â3)]-ß-D-glucopyranoside (1), (23R,25R)-26-O-ß-D-glucopyranosyl-16,23-cyclocholesta-5,17,20(22)-trien-3ß,22,26-triol-3-O-α-L-rhamnopyranosyl-(1â3)-ß-D-glucopyranoside (2), (23R,25R)-16,23-cyclocholesta-5,16,20(22)-trien-3ß,22,26-triol-3-O-α-L-rhamnopyranosyl-(1â3)-ß-D-glucopyranoside (3), 3ß-[(O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-gluco-pyranosyl)oxy]-pregna-5,17(20)-diene-16-one-20-carboxylic acid 4''''-O-ß-D-glucopyranosylisopentyl ester (4), cambodianoside A (5), diosbulbiside C (6), and diosbulbiside D (7), by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1 and 4-7 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW 264.7 cells with IC50 values ranging from 19.03±1.84 to 67.92±3.81â µM, whereas compounds 2 and 3 were inactive with IC50 values over 100â µM.
Assuntos
Dracaena , Lipopolissacarídeos , Saponinas , Camundongos , Animais , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Células RAW 264.7 , Trientina , Saponinas/farmacologia , Saponinas/química , Estrutura MolecularRESUMO
Hericium erinaceus is a species of mushroom with high nutritional value that is used mainly as food in tropical countries. Phytochemical study of H. erinaceus led to the isolation of an undescribed compound, named as hericium VN (1), together with nine known compounds, 1-(2-formyl-1-pyrrolyl)butanoic acid (2), herierin III (3), 5'-(methylthio)adenosine (4), adenosine (5), nicotinic acid (6), (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3ß-ol (7), 5α,8α-peroxycerevisterol (8), (22E,24R)-5α,8α-epidioxy-egosta-6,22-diene 3-O-ß-D-glucopyranoside (9), and cerevisterol (10) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configuration of compound 1 was determined by experimental combined with calculated electronic circular dichroism spectra. Compound 7 exhibited cytotoxic effects against brain tumor cell line CCF-STTG1 with the IC50 value of 15.50 µM, compared to that of the positive control compound, doxorubicin, which showed IC50 value of 15.84 µM.
Assuntos
Astrocitoma , Ensaios de Seleção de Medicamentos Antitumorais , Hericium , Humanos , Estrutura Molecular , Astrocitoma/tratamento farmacológico , Hericium/química , Neoplasias Encefálicas/tratamento farmacológico , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Ressonância Magnética Nuclear BiomolecularRESUMO
One new bithiophene derivative, 5-(but-3-en-1-yn-1-yl)-5'-(methoxymethyl)-2,2'-bithiophene (1), along with twelve known compounds, senecioester (2), tiglinsaureester (3), 5-acetoxymethyl-2'-(but-3-en-1-yn-1-yl)-2,5'-bithiophene (4), 5-(4-isovaleroyloxybut-1-ynyl)-2,2'-bithiophene (5), 5-hydroxymethyl-(2,5':2',5'')-terthienyl tiglate (6), 5-hydroxymethyl-(2,5':2',5'')-terthienyl agelate (7), 5- hydroxymethyl-2,5':2',5''-terthiophene dimethylacrylate (8), 5-methoxymethyl-2,2':5',2''-terthiophene (9), α-terthiophene (10), 1,3,8,9-tetrahydroxycoumestan 3-sulfate (11), demethylwedelolactone (12), and wedelolactone (13) were isolated from the methanol extract of aerial parts of Eclipta prostrata (L.) L. All isolated compounds were evaluated for the protective ability on the HepG2 cells. At the concentration of 100 µM, compounds 11-13 showed the highest hepatoprotective effects, with HepG2 cell viability ranging from 38.68% to 48.54%. Bithiophenes showed higher hepatoprotective cell viability than terthiophenes.
RESUMO
From marine sponge-associated fungus Hamigera avellanea, thirteen secondary metabolites including a pair of undescribed alkaloid enantiomers (+)-hamiavemin A (4S) (+)-1 and (-)-hamiavemin A (4R) (-)-1. Compound 1 was enantiomers resolved by the Chiralpak AS-3 column, using a hexane/isopropanol mobile phase. Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configuration of (+)-1 and (-)-1 were assigned tentatively by ECD calculations. Among the isolates, compound 6 showed strongest antibacterial activity against Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Escherichia coli, Salmonella enterica, and Candida albicans with the MIC values of 2, 2, 16, 32, 64, and 16â µg/mL, respectively, which were stronger than that of the positive control compound, kanamycin (MIC values ranging from 4 to 128â µg/mL). In addition, compounds 1, 2, and 9 showed moderate cytotoxic activity against three cancer cell lines, HepG2, A549, and MCF-7 with the IC50 values ranging from 55.35±1.70 to 83.02±2.85â µg/mL.
Assuntos
Alcaloides , Anti-Infecciosos , Antineoplásicos , Poríferos , Animais , Anti-Infecciosos/química , Poríferos/microbiologia , Antibacterianos/química , Fungos/química , Antineoplásicos/farmacologia , Antineoplásicos/química , Alcaloides/farmacologia , Testes de Sensibilidade MicrobianaRESUMO
A phytochemical investigation of the methanolic extract of the Macropanax membranifolius C.B. Shang leaves led to the isolation of three new flavans, (2R,3R)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (1), (2S,3S)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (2), (2S,3R)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (3), one new triterpene glycoside 3-O-ß-D-xylopyranosyl-(1â6)-[ß-D-xylopyranosyl-(1â2)]-ß-D-glucopyranosyl-oleanolic acid 28-O-ß-D-glucopyranoside (4), together with nine known compounds (5-13). Their chemical structures were elucidated based on HR-ESI-MS, NMR spectroscopic data. The absolute configurations of compounds 1-3 were established by electronic circular dichroism (ECD) spectra. At concentration of 20â µM, compounds 1-13 showed the percentages of dead cell in the range of 2.14 % to 33.61 % against KB, HepG2, HL60, P388, HT29, and MCF7 cancerous cell lines by SRB assay.
Assuntos
Antineoplásicos , Saponinas , Triterpenos , Saponinas/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Triterpenos/farmacologia , Triterpenos/química , Estrutura MolecularRESUMO
From the fruits of Schisandra cauliflora, five new dimethylbutyrylated dibenzocyclooctadiene lignans, named schisandracaurins A-E, were isolated using separation and chromatographic techniques. Their structures were determined by extensive analyses of HR-ESI-MS, NMR, and ECD spectra. The schisandracaurins A-E potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values from 21.4 to 30.3â µM.
Assuntos
Lignanas , Schisandra , Schisandra/química , Lipopolissacarídeos/farmacologia , Estrutura Molecular , Frutas/química , Lignanas/química , Ciclo-Octanos/farmacologia , Ciclo-Octanos/análise , Ciclo-Octanos/químicaRESUMO
Vitex trifolia L. is a medicinal plant and widely distributed in the northern mountainous areas of Vietnam. Phytochemical study on the fruits of this plant led to the isolation of nine iridoid derivatives (1-9) including three undescribed compounds (1-3). Their structures were elucidated to be 3''-hydroxyscrophuloside A1 (1), 3''-hydroxycallicoside D (2), 2'-p-hydroxybenzoylaucubin (3), 6'-p-hydroxybenzoylmussaenosidic acid (4), nishindaside (5), agnuside (6), 10-O-vanilloylaucubin (7), 6'-O-p-hydroxybenzoyl-gardoside (8), and buddlejoside B (9) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1, 2, 4, and 8 significantly posessed anti-barterial activity against Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa strains with MIC values in range of 16-64â µg/mL. At concentration of 20â µM, compounds 1-9 did not show cytotoxic effects against human lung cancer cells (PC9).
Assuntos
Anti-Infecciosos , Antineoplásicos , Vitex , Humanos , Iridoides/química , Vitex/química , Frutas/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/análise , Extratos Vegetais/análiseRESUMO
Gnetum latifolium var. funiculare Markgr. is a medicinal plant and widely distributed in mountainous areas of Vietnam. Phytochemical investigation on the trunks of this plant afforded eight stilbene derivatives (1-8) including for new compounds (1-4). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. Among the isolates, compounds 1-3 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with the IC50 values ranging from 46.81 to 68.10â µM, compounds 4 and 6 showed weak effects with the IC50 values of 96.57 and 79.46â µM, respectively, compared to that of the positive control compound, dexamethasone (IC50 14.20â µM).
RESUMO
Five asterosaponins (1-5), including one new compound named protonodososide (1), were isolated from the methanol extract of the starfish Protoreaster nodosus, after subjecting to various chromatographic separations. The structural elucidation was confirmed by careful analysis of the 1D, 2D NMR, and HR ESI QTOF mass spectra. The cytotoxicity of isolated compounds was evaluated on five human cancer cell lines including HepG2, KB, MCF7, LNCaP, and SK-Mel2.
Assuntos
Antineoplásicos , Estrelas-do-Mar , Animais , Humanos , Estrelas-do-Mar/química , Espectroscopia de Ressonância Magnética , Linhagem Celular Tumoral , Espectrometria de Massas por Ionização por Electrospray , Antineoplásicos/química , Estrutura MolecularRESUMO
Three new chromanes, malloapeltas J-L (1-3), and one new flavone C-glycoside, malloflavoside (4), together with four known compounds, apigenin 6-C-ß-D-xylopyranosyl-8-C-α-L-arabinopyranoside (5), apigenin 6-C-ß-D-glucopyranosyl-8-C-α-L-arabinopyranoside (6), apigenin 7-O-ß-D-apiofuranosyl-(1â2)-ß-D-glucopyranoside (7), and acantrifoside E (8) were isolated from the methanol extract of the leaves of Mallotus apelta. Their chemical structures were determined using spectroscopic methods, including 1D, 2D NMR, and HR-ESI-MS methods. All the isolated compounds were evaluated their cytotoxic activity against human prostate cancer (PC-3) and human breast cancer (MCF-7) cells, but none of them showed cytotoxicities on both human cancer cell lines.
Assuntos
Flavonas , Mallotus (Planta) , Humanos , Apigenina , Glicosídeos/farmacologia , Glicosídeos/química , Flavonas/farmacologiaRESUMO
Five new seco-labdane-type diterpenoids, caesalatisics A-E (1-5), were isolated from the leaves of Caesalpinia latisiliqua (Cav.) Hattink. Their chemical structures were determined using 1D and 2D NMR, mass spectra, and circular dichroism spectroscopies.
Assuntos
Caesalpinia , Diterpenos , Caesalpinia/química , Diterpenos/análise , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta/químicaRESUMO
Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together with 6-methoxycomaparvin-5-methylether-8-O-sodium sulfate (6), 6-methoxycomaparvin-8-O-sodium sulfate (7), comaparvin-8-O-sodium sulfate (8), and 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone-6-O-sodium sulfate (9) were isolated from the Vietnamese crinoid Comanthus delicata. Their chemical structures were elucidated by extensive analysis of the one dimensional (1D) and 2D-NMR, high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra as well as calculation of optical rotation. In addition, significant cytotoxicity was observed for 6 against LNCaP (prostate cancer) cell line with IC50 value of 20.29 ± 2.43 µM, whereas moderate or weak cytotoxic effects were observed for 1-3 and 5-8 on SK-Mel-2 (melanoma) cell line and 7 and 8 against LNCaP cell line, with IC50 values ranging from 49.96 ± 1.74 to 76.92 ± 5.85 µM.