RESUMO
Fifteen compounds including nine new diterpenes were isolated from the roots of Croton yunnanensis. By HRESIMS, NMR, ECD data, and X-ray diffraction analysis, the new compounds were characterized as eight neo-clerodane diterpenes (compounds 1-8) and one 15,16-dinor-ent-pimarane diterpene (9). All diterpenes were assayed for their hypoglycemic activities. Compounds 1-4, 6, 7, and 10 promoted glucose uptake activity in insulin-resistant 3T3-L1 adipocytes. Compounds 1 and 6 showed insulin sensitizing activity, potentiating conspicuously their glucose uptake activity at a concentration of 20 µM when treated synergistically with low-concentration insulin at 1 nM.
Assuntos
Croton , Diterpenos Clerodânicos , Diterpenos , Insulinas , Croton/química , Hipoglicemiantes/farmacologia , Diterpenos/farmacologia , Diterpenos/química , Diterpenos Clerodânicos/química , Glucose , Estrutura MolecularRESUMO
Eight compounds were isolated from ethyl acetate fraction of 80% ethanol extract of the hulls of Garcinia mangostana by silica gel, Sephadex LH-20 column chromatography, as well as prep-HPLC methods. By HR-ESI-MS, MS, 1D and 2D NMR spectral analyses, the structures of the eight compounds were identified as 16-en mangostenone E(1), α-mangostin(2), 1,7-dihydroxy-2-(3-methy-lbut-2-enyl)-3-methoxyxanthone(3), cratoxyxanthone(4), 2,6-dimethoxy-para-benzoquinone(5), methyl orselinate(6), ficusol(7), and 4-(4-carboxy-2-methoxyphenoxy)-3,5-dimethoxybenzoic acid(8). Compound 1 was a new xanthone, and compound 4 was a xanthone dimer, compound 5 was a naphthoquinone. All compounds were isolated from this plant for the first time except compounds 2 and 3. Cytotoxic bioassay suggested that compounds 1, 2 and 4 possessed moderate cytotoxicity, suppressing HeLa cell line with IC_(50) va-lues of 24.3, 35.5 and 17.1 µmol·L~(-1), respectively. Compound 4 also could suppress K562 cells with an IC_(50) value of 39.8 µmol·L~(-1).
Assuntos
Antineoplásicos , Garcinia mangostana , Garcinia , Xantonas , Humanos , Garcinia mangostana/química , Células HeLa , Espectroscopia de Ressonância Magnética , Xantonas/farmacologia , Garcinia/química , Extratos Vegetais/química , Estrutura MolecularRESUMO
Nine compounds were isolated from the 90% ethanol extract of Salacia polysperma by silica gel, Sephadex LH-20 column chromatography, together with preparative HPLC methods. Based on HR-ESI-MS, MS, 1D and 2D NMR spectral analyses, the structures of the nine compounds were identified as 28-hydroxy wilforlide B(1), wilforlide A(2), 1ß,3ß-dihydroxyurs-9(11),12-diene(3),(-)-epicatechin(4),(+)-catechin(5),(-)-4'-O-methyl-ent-galloepicatechin(6), 3-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)propan-1-one(7),(-)-(7S,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7,9-diol-7'-aldehyde(8), and vanillic acid(9). Compound 1 is a new oleanane-type triterpene lactone. Compounds 1, 3, 4, 7-9 were isolated from the Salacia genus for the first time. All compounds were assayed for their α-glucosidase inhibitory activity. The results suggested that compound 8 exhibited moderate α-glucosidase inhibitory activity, with an IC_(50) value of 37.2 µmol·L~(-1), and the other compounds showed no α-glucosidase inhibitory activity.
Assuntos
Salacia , Triterpenos , Salacia/química , alfa-Glucosidases , Triterpenos/farmacologia , Espectroscopia de Ressonância Magnética , Etanol , Estrutura MolecularRESUMO
Thirty-five tigliane diterpenoids and two ent-kaurane diterpenoids were isolated from the leaves of Croton damayeshu, and, among them, compounds 1-10 were characterized as new tigliane diterpenoids. The structures of compounds 1-10 were determined by analysis of their HRESIMS, NMR, and ECD data and by chemical methods. The isolates were assayed for their larvicidal, antifungal, and α-glucosidase inhibitory activities, and compounds 8-10 were found to possess larvicidal activities against Plutella xylostella with LC50 values of 0.19, 0.16, and 0.26 µM, respectively, comparable to the LC50 of 0.14 µM for the positive control, flubendiamide.
Assuntos
Croton , Diterpenos do Tipo Caurano , Diterpenos , Forbóis , Antifúngicos/farmacologia , Croton/química , Diterpenos/química , Diterpenos do Tipo Caurano/farmacologia , Estrutura Molecular , alfa-GlucosidasesRESUMO
Two new isopimarane diterpenoids, named 1α-hydroxy-7-oxoisopimara-8, 15-diene (1), 11ß-hydroxy-7-oxoisopimara-8(14), 15-diene (2), together with six known compounds (3-8), were isolated from the medicinal plant Salacia cochinchinensis. All isolates were assayed for their cytotoxicity and α-glucosidase inhibitory activity. Results suggested compounds 1, 3 possessed significant cytotoxic activity against HepG2, HL60, and Hela cell lines with IC50 values ranging from 0.23 to 0.35 µM, and compounds 7, 8 exhibited noticeable α-glucosidase inhibitory ability with IC50 values of 0.25 and 0.31 µM, respectively.
Assuntos
Diterpenos , Salacia , Células HeLa , Humanos , Estrutura Molecular , alfa-GlucosidasesRESUMO
Five sesquiterpenoids were isolated from 90% ethanol extract of Croton yunnanensis by silica gel,Sephadex LH-20 column chromatography,as well as prep-HPLC methods. Based on MS,1 D and 2 D NMR spectral analyses,the structures of the five compounds were identified as 11-methoxyl alismol(1),6ß,7ß-epoxy-4α-hydroxyguaian-10-ene(orientalol C,2),multisalactone D(3),arvestonol(4),and 4,5-dihydroblumenol A(5). Compound 1 was a new guaiane-type sesquiterpenoid. Compounds 2-4 were isolated from the Croton genus for the first time,and compound 5 was obtained from this plant for the first time.
Assuntos
Croton , Sesquiterpenos de Guaiano , Sesquiterpenos , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Four new diterpene glucosides, namely perovskiaditerpenosides A - D (1 - 4), were isolated from the BuOH extract of Perovskia atriplicifolia. Their structures were well elucidated by chemical methods and comprehensive spectroscopic analyses including MS, IR, and NMR (1D and 2D). The newly isolated compounds were screened for their cytotoxic activity against HepG2, NB4, HeLa, K562, MCF7, PC3, and HL60. The obtained results indicated that the new compounds possessed considerable cytotoxic activity.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Glucosídeos/isolamento & purificação , Lamiaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Butanóis , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Extratos Vegetais , Análise EspectralRESUMO
Five new diterpenoids (1-5) were isolated from the roots of Aralia melanocarpa, together with four known compounds, 7ß-hydroxy-ent-pimara-8(14),15-diene-19-oic acid (6), 18-norpimara-8(14),15-dien-4-ol (7), ent-16ßH,17-isovalerate-kauran-19-oic acid (8), and ent-16α,17-dihydroxykauran-19-oic acid (9). Based on the MS, IR, and NMR spectral analysis, the structures of the five new diterpenoids (1-5) were elucidated. The cytotoxic activities of compounds 1-9 were assayed, and compounds 1 and 2 showed cytotoxicity in four cancer cell lines with IC50s from 4.2 to 8.2 µM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Aralia/química , Diterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Linhagem Celular , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Estrutura Molecular , Raízes de Plantas/químicaRESUMO
Five new icetexane diterpenoids, namely, perovskatones B-D (1, 3, 4), 1α-hydroxybrussonol (2), and 1α-hydroxypisiferanol (5), were isolated from Perovskia atriplicifolia, together with a new natural product (6) and two known compounds, przewalskin E (7) and brussonol (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D, and 2D NMR data. Compounds 1-8 were assayed for their inhibitory hepatitis B virus activities in the HepG 2.2.15 cell line. The results suggested that compounds 1 and 2 possessed noticeable anti-hepatitis B virus activity in vitro, suppressing the replication of hepatitis B virus DNA with selectivity index values of 154.3 and 137.7, respectively.
Assuntos
Antivirais/farmacologia , Diterpenos/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Lamiaceae/química , Extratos Vegetais/farmacologia , Antivirais/química , Antivirais/isolamento & purificação , Antivirais/uso terapêutico , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/uso terapêutico , Células Hep G2 , Hepatite B/tratamento farmacológico , Hepatite B/virologia , Humanos , Estrutura Molecular , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/uso terapêuticoRESUMO
A phytochemical investigation on the stems of Garcinia bracteata collected from Xishuangbanna resulted in the isolation of a new flavone. By analysis of the HRESIMS, IR, UV, 1D and 2D NMR spectra, the structure of the new compound was determined as 7-methoxy-4',6-dihydroxy-8-isobutyryl-flavone(1). Compound 1 was also tested for its anti-tobacco mosaic virus(TMV) activity. Results suggested the 1 possessed remarkable anti-TMV activity, with an inhibition rate of 28.2%.
Assuntos
Antivirais/química , Antivirais/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Flavonas/química , Flavonas/farmacologia , Garcinia/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Flavonas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Folhas de Planta/química , Vírus do Mosaico do Tabaco/crescimento & desenvolvimentoRESUMO
An investigation on the chemical constituents of the 90% EtOH extract of Perovskia atriplicifolia led to the isolation of fifteen compounds from the EtOAc fraction. Based on the detailed spectral analysis (MS, 1D and 2D NMR), as well as comparison with the literatures, the structures of compounds 1-15 were determined as cirsimaritin (1), salvigenin (2), syringaldehyde (3), vinyl caffeate (4), 2α, 3α-dihydroxyolean-12-en-28-oicacid (5), 2α, 3α-dihydroxyurs-12-en-28-oicacid (6), niga-ichigoside F1 (2α, 3ß, 19α, 23- tetrahydroxyurs - 12-en-28-oicacid- O-ß-D- glucopyranoside, 7), sericoside (8), 4-epi-niga-ichigoside F1 (2α, 3ß, 19α, 24-tetrahydroxyurs-12-en-28-oicacid O-ß-D-glucopyranoside, 9), 2α, 3ß, 24-trihydroxyolean-12-en-28-oicacid O-ß-D-glucopyranosyl-(1 --> 2) - ß-D-glucopyranoside (10), pruvuloside A (11), asteryunnanoside A [2α, 3ß, 23-trihydroxyolean-12-en-28-oicacid O-ß-D-glucopyranosyl-(1 --> 2)-ß- D- glucopyranoside,12], rosmarinic acid methyl ester (13), ß-sitosterol (14), and daucosterol (15), respectively. Compounds 1-13 were isolated from the Perovskia genus for the first time. All the compounds were obtained from P. atriplicifolia for the first time.
Assuntos
Medicamentos de Ervas Chinesas/química , Lamiaceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Four new clerodane diterpenes, namely sagittatayunnanosides A-D (1-4), were isolated from the roots of Tinospora sagittata var. yunnanensis, together with two known compounds, tinospinoside C (5) and tinospinoside E (6). The structures of the four new compounds were well elucidated by extensive analyses of the MS, IR, and 1D and 2D NMR data. The cytotoxic and antifouling activities of compounds 1-6 were evaluated.
Assuntos
Diterpenos Clerodânicos/isolamento & purificação , Tinospora/química , Linhagem Celular Tumoral , Diterpenos Clerodânicos/química , Humanos , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria InfravermelhoRESUMO
In the screening search for Hepatitis B virus inhibitory agents from medicinal plants, the ethanol extract of Piper longum Linn. was found to possess superior anti-HBV activity in vitro. Bioassay-guided fractionation coupled with repeated purification resulted in the isolation of four new compounds, involving two new glycosides longumosides A (1) and B (2) and two new amide alkaloids erythro-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (3), threo-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (4), as well as two compounds 3ß,4α-dihydroxy-2-piperidinone (5), 5,6-dihydro-2(1H)-pyridinone (6) from natural source for the first time. The structures of the four new compounds were determined by extensive analyses of the MS, IR, 1D and 2D NMR data. Besides, the compounds 2-6, together with the known compounds 7-11 obtained previously, were assayed for their anti-HBV activity by using Hep G 2.2.15 cell line in vitro. Results suggested the compound piperine (7) possessed remarkable inhibitory HBV activity, against the secretion of hepatitis B virus surface antigen (HBsAg) and hepatitis B virus e antigen (HBeAg) with the Selectivity Index (SI) values of 15.7 and 16.8, respectively.
Assuntos
Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Piper/química , Extratos Vegetais/farmacologia , Antivirais/química , Antivirais/isolamento & purificação , Relação Dose-Resposta a Droga , Células Hep G2 , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Relação Estrutura-AtividadeRESUMO
A new oxepinochromenone, rugosachromenone A (1), seven new flavonoids, rugosaflavonoids A-G (2-8), and 11 known compounds (9-19) were isolated from the flower buds of Rosa rugosa. Compound 1 is found from Nature for the first time. Compound 2 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cells with IC50 values of 2.2, 2.5, and 2.3 µM, respectively, and 3 was toxic to A549 and MCF7 cells with IC50 values of 1.2 and 2.8 µM, respectively.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Cromonas/isolamento & purificação , Cromonas/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Rosa/química , Antineoplásicos Fitogênicos/química , Cromonas/química , Medicamentos de Ervas Chinesas/química , Feminino , Flavonoides/química , Flores/química , Humanos , Concentração Inibidora 50 , Células MCF-7 , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Eight new C-4-alkylated deoxybenzoins (1-8), three new diphenylethylenes (9-11), and five known diphenylethylenes were isolated from Arundina graminifolia. The structures of 1-11 were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. Compounds 9-11 are the first naturally occurring diphenylethylenes possessing a hydroxyethyl unit. Compounds 1-11 were evaluated for cytotoxicity against five human tumor cell lines. Compounds 4, 5, and 9-11 showed significant cytotoxicity against five cancer cell lines, with IC50 values ranging from 1.8 to 8.7 µM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Benzoína/análogos & derivados , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Etilenodiaminas/isolamento & purificação , Etilenodiaminas/farmacologia , Orchidaceae/química , Antineoplásicos Fitogênicos/química , Benzoína/química , Benzoína/isolamento & purificação , Benzoína/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Etilenodiaminas/química , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estilbenos/químicaRESUMO
Two new flavanes, (2R)-4'-hydroxy-2',5,7-trimethoxyflavane (1) and (2R,4R)-2',4'-dihydroxy-5,7-dimethoxyflavan-4-ol (2), were isolated from Uraria clarkei, together with two known compounds 5,7-dimethoxy-4'-hydroxyflavan (3) and 5,7,4'-trimethoxyflavan (4). The structures of the new flavanes were characterized by analyses of the MS, IR, UV, CD, 1D, and 2D NMR data. Cytotoxicity test suggested that compounds 1-4 possessed slight activity against K-562 and Hela cell lines, with the IC50 values ranging from 26.6 to 56.3 µM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Fabaceae/química , Flavonoides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/farmacologia , Células HeLa , Humanos , Concentração Inibidora 50 , Células K562 , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Two new sphingolipids, pipercerebrosides A (1) and B (2), were isolated from the leaves of Piper betle L. Their structures, including absolute configurations, were determined by spectroscopic analysis and chemical degradation. These two compounds did not show significant cytotoxic activity against the cancer cell lines K562 and HL-60 in a MTT assay.
Assuntos
Medicamentos de Ervas Chinesas/química , Piper betle/química , Folhas de Planta/química , Esfingolipídeos/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Células HL-60 , Humanos , Células K562 , Metilação , Estrutura Molecular , Oxirredução , Esfingolipídeos/isolamento & purificação , Esfingolipídeos/farmacologiaRESUMO
OBJECTIVE: To investigate the application of tunica dartos flap coverage to the prevention of urinary fistula in tubularized incised plate (TIP) urethroplasty. METHODS: This study included 140 cases of hypospadias following TIP urethroplasty, aged 1.9-22 (mean 5.6) years. Of the total number, 85 cases of the distal type were treated by coverage of the neourethra with the longitudinal ventrolateral pedicled-dartos penile skin flap, while the other 55 cases of the proximal type with the pedicled-dartos flap of arteriae scrotales anteriories. RESULTS: Urethrocutaneous fistula occurred in 12 of the patients, including 7 cases of distal and 6 cases of proximal hypospadias. CONCLUSION: For distal hypospadias, the longitudinal ventrolateral pedicled-dartos penile skin flap can be used, while for proximal urethroplasty, the pedicled-dartos flap of arteriae scrotales anteriories can be applied in coverage of the neourethra, which can effectively reduce the incidence of fistula.
Assuntos
Hipospadia/cirurgia , Procedimentos de Cirurgia Plástica/métodos , Tela Subcutânea/transplante , Uretra/cirurgia , Procedimentos Cirúrgicos Urológicos Masculinos/métodos , Adolescente , Criança , Pré-Escolar , Humanos , Lactente , Masculino , Escroto/irrigação sanguínea , Retalhos Cirúrgicos/irrigação sanguínea , Fístula Urinária/prevenção & controle , Fístula Urinária/cirurgia , Adulto JovemRESUMO
Two new cycloartane triterpenoid glycosides, named curculigosaponin N and curculigosaponin O, were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated on the basis of comprehensive spectroscopic analysis including IR, MS, 1D, and 2D NMR (HSQC and HMBC).
Assuntos
Curculigo/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Rizoma/química , Saponinas/química , Triterpenos/químicaRESUMO
OBJECTIVE: To investigate the diagnosis and treatment of epididymal obstructive azoospermia (OA) by microsurgery. METHODS: We performed surgical scrotal exploration for 57 cases of OA whose obstruction was suspected to be in the epididymis. Those confirmed to be epididymal OA cases and with motile sperm in the epididymis underwent longitudinal-2-suture intussusceptive vasoepididymostomy (LIVES). And for those with sperm in the epididymal head only or with bilateral obstruction or absence of the vas deferens in the distal epididymis, the sperm were collected and subjected to cryopreservation for intracytoplasmic sperm injection (ICSI). After surgery, the patients were followed up for observation of the semen parameters and the rate of pregnancy. RESULTS: Of the total number of patients, 53 (92.9%) were diagnosed with epididymal OA by scrotal exploration, 47 (82.5%) underwent microsurgery, and the other 10 (17.5%) received sperm cryopreservation. At 1 to 18 months after surgery, motile sperm were found in the ejaculate in 46.8% of the cases (22/47), natural pregnancy in 10.6% (5/47), and ICSI pregnancy in 18.5% (6/32). CONCLUSION: With the development of microsurgery, non-invasive means should be the first choice for the diagnosis of OA. And surgical exploration can be employed to determine the location of obstruction and the option for treatment.