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1.
Molecules ; 26(7)2021 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-33805102

RESUMO

Three new helvolic acid derivatives (named sarocladilactone A (1), sarocladilactone B (2) and sarocladic acid A (3a)), together with five known compounds (6,16-diacetoxy-25-hy- droxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (3b), helvolic acid (4), helvolinic acid (5), 6-desacetoxy-helvolic acid (6) and 1,2-dihydrohelvolic acid (7)), were isolated from the endophytic fungus DX-THL3, obtained from the leaf of Dongxiang wild rice (Oryza rufipogon Griff.). The structures of the new compounds were elucidated via HR-MS, extensive 1D and 2D NMR analysis and comparison with reported data. Compounds 1, 2, 4, 5, 6 and 7 exhibited potent antibacterial activities. In particular, sarocladilactone B (2), helvolinic acid (5) and 6-desacetoxy-helvolic acid (6) exhibited strongly Staphylococcus aureus inhibitory activity with minimum inhibitory concentration (MIC) values of 4, 1 and 4 µg/mL, respectively. The structure-activity relationship (SAR) of these compounds was primarily summarized.


Assuntos
Antibacterianos , Ácido Fusídico/análogos & derivados , Hypocreales/química , Oryza/microbiologia , Staphylococcus aureus/crescimento & desenvolvimento , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Ácido Fusídico/química , Ácido Fusídico/isolamento & purificação , Ácido Fusídico/farmacologia
2.
Chin J Nat Med ; 16(7): 509-512, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30080650

RESUMO

The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC50 values ranging from 8.67 to 98.89 µmol·L-1.


Assuntos
Alcaloides/química , Alcaloides/toxicidade , Clausena/química , Extratos Vegetais/química , Folhas de Planta/química , Caules de Planta/química , Células A549 , Alcaloides/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/toxicidade , Carbazóis/química , Carbazóis/isolamento & purificação , Carbazóis/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Células HeLa , Humanos , Estrutura Molecular , Extratos Vegetais/toxicidade , Plantas Medicinais/química
3.
Pak J Pharm Sci ; 28(6): 2191-8, 2015 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-26639511

RESUMO

The extraction, fractionation and recognition of flavonoids from the ethanolic extract of young twigs and leaves of C. bonduc were carried out. In addition, cytotoxic study of the flavonoids on two cancer cell lines, BGC-823 and HeLa was carried our using sulphorhodamine B assay. Seven flavonoids, six of which are being reported for the first time in this plant, were isolated. Their structures were identified by MS and NMR spectroscopic methods. Petroleum ether, ethyl acetate and water fractions exhibited moderate cytotoxic activity against HeLa cells. Five compounds showed cytotoxic activity against HeLa cell in comparison with Paclitaxel, while only one compound showed a good degree of cytotoxic activity against BGC-823 cell in comparison to Paclitaxel. The results obtained showed a structure - activity relationship.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Caesalpinia , Flavonoides/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta , Caules de Planta , Antineoplásicos Fitogênicos/isolamento & purificação , Caesalpinia/química , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Sobrevivência Celular/efeitos dos fármacos , Fracionamento Químico , Flavonoides/isolamento & purificação , Células HeLa , Humanos , Concentração Inibidora 50 , Espectrometria de Massas , Estrutura Molecular , Paclitaxel/farmacologia , Fitoterapia , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Caules de Planta/química , Plantas Medicinais , Espectroscopia de Prótons por Ressonância Magnética , Solventes/química , Relação Estrutura-Atividade
4.
Zhongguo Zhong Yao Za Zhi ; 40(8): 1503-7, 2015 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-26281588

RESUMO

Five flavone C-glycosides were isolated from the methanol extract of the degrease seeds of Ziziphus jujuba var. spinosa though various column chromatography methods including silica gel, MPLC, and HPLC. The structures were elucidated as 6"-feruloyl- 6'''-vanillylspinosin(1), 6",6'"-diferuloylspinosin(2), spinosin(3), swertisin(4) and isoswertisin(5) based on the NMR and MS spectral data. 1 is a new compound.


Assuntos
Medicamentos de Ervas Chinesas/química , Flavonas/química , Glicosídeos/química , Sementes/química , Ziziphus/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Flavonas/isolamento & purificação , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular
5.
J Asian Nat Prod Res ; 15(3): 215-20, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-23327112

RESUMO

Two new coumarins, clauexcavatins A (1) and B (2), along with seven known ones (3-9), were isolated from the roots of Clausena excavata Burm. f. (Rutaceae). Their structures were elucidated on the basis of spectral data.


Assuntos
Clausena/química , Cumarínicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Carbazóis/química , Carbazóis/isolamento & purificação , Cumarínicos/química , Medicamentos de Ervas Chinesas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química
6.
Eur J Med Chem ; 59: 243-52, 2013 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-23231968

RESUMO

Bigelovin is a sesquiterpene lactone isolated from the plant Inula helianthus-aquatica which was traditionally used in cancer treatment in Yunnan, China. The potent apoptotic activities of bigelovin in human leukemia U937 cells were shown in our previous study. The present study investigated the anti-angiogenic and immunomodulatory effects of bigelovin using transgenic zebrafish Tg(fli1a:EGFP)y1 with fluorescent blood vessels and human peripheral blood mononuclear cells (PBMCs), respectively. Furthermore, the inhibitory activities of bigelovin on the human endothelial cell adhesion molecules (CAMs) were also examined. Our results showed that the growth of subintestinal vessels of the bigelovin-treated zebrafish embryos was significantly inhibited and the gene expressions in angiogenesis signaling pathways (e.g. Ang2 and Tie2) of the zebrafish were down-regulated after bigelovin treatment. Besides, the proliferation and Th1 cytokines productions (e.g. IFN-γ, IL-2 and IL-12) were suppressed in bigelovin-treated PBMCs. On the other hand, bigelovin was shown to significantly inhibit the human monocyte adhesion to human endothelial cells and the gene expressions of inflammation-related CAMs (e.g. ICAM-1, VCAM-1 and E-selectin) were significantly down-regulated in bigelovin-treated human endothelial cells. In summary, our data provide the first evidence that bigelovin possesses anti-angiogenic and immunomodulatory activities, suggesting bigelovin may exert multi-target functions against cancer in animal models.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Helianthus/química , Fatores Imunológicos/química , Fatores Imunológicos/farmacologia , Lactonas/farmacologia , Neovascularização Fisiológica/efeitos dos fármacos , Extratos Vegetais/farmacologia , Sesquiterpenos/farmacologia , Animais , Animais Geneticamente Modificados , China , Embrião não Mamífero/efeitos dos fármacos , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Células U937 , Peixe-Zebra
7.
Zhongguo Zhong Yao Za Zhi ; 37(19): 2898-901, 2012 Oct.
Artigo em Chinês | MEDLINE | ID: mdl-23270229

RESUMO

Chemical constituents in ethyl acetate and butanol fractions of ethanol extracts from Acorus tatarinowii were separated by column chromatography. Bufo skeletal muscle fatigue model was established to study the anti-fatigue activity of separated compounds. Five compounds were separated and identified by spectroscopic analysis as acoramone(1),cycloartenone(2),2,4,5-trimethoxyl-2'-butoxy-1,2-phenyl propandiol(3),5-hydroxymethyl furfural(4), and 5-butoxymethyl furfural(5). Compound 3 was a new compound, and compounds 2 and 5 were separated from this plant for the first time. Compound 4 exhibited a notable anti-fatigue activity.


Assuntos
Acorus/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Bufonidae , Fadiga/tratamento farmacológico , Músculo Esquelético/efeitos dos fármacos
8.
Phytochemistry ; 83: 63-9, 2012 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-22959532

RESUMO

Labdane diterpene glycosides cathargyroside A and cathargyroside B, monoterpene glycosides vervenone-10-O-ß-D-glucopyranoside and vervenone-10-O-ß-D-apiofuranosyl-(1″→6')-ß-D-glucopyranoside, as well as lignan glycosides cedrusinin-4-O-α-L-rhamnopyranoside and (+)-cyclo-olivil-9'-O-ß-D-xylopyranoside, along with 39 known compounds, were obtained from the methanol extract of the twigs and leaves of Cathaya argyrophylla. These compounds were identified mainly by analyzing their NMR and MS data. Almost all of these compounds were hitherto unknown in this genus. The isolated compounds were screened against Candida albicans and Staphylococcus aureus for antimicrobial assay, and against K562, HT-29, BEL-7402, SGC-7901, B16, BGC-823, U251 and A549 cancer cell lines for cytotoxic activities. One compound showed antimicrobial activity against C. albicans, and four of them displayed cytotoxicity. Similarity analysis on the chemical constituents of the genera Cathaya, Picea and Pinus supported their close phylogenetic relationships.


Assuntos
Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Candida albicans/efeitos dos fármacos , Glicosídeos/farmacologia , Pinaceae/química , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Lignanas/química , Testes de Sensibilidade Microbiana , Conformação Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Caules de Planta/química , Relação Estrutura-Atividade , Terpenos/química
9.
Bioorg Med Chem Lett ; 22(20): 6377-80, 2012 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-22989532

RESUMO

Zizimauritic acids A-C (1-3), three novel nortriterpenes with a unique A-nor-E-seco spiro-lactone ceanothane-type triterpene skeleton, together with 3 known triterpenes ceanothenic acid (4), betulinic acid (5), and ceanothic acid (6), were isolated from the roots of Ziziphus mauritiana. Compounds 1-4 showed cytotoxicities with the IC(50) values ranging from 5.05 to 11.94 µg/ml, and compounds 1 and 3 showed an inhibitory effect on the growth of Staphylococcus aureus with the IC(50) values 2.17 and 12.79 µg/ml. A plausible biosynthetic pathway of compounds 1-3 was proposed.


Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Triterpenos/química , Triterpenos/farmacologia , Ziziphus/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Neoplasias/tratamento farmacológico , Raízes de Plantas/química , Infecções Estafilocócicas/tratamento farmacológico , Staphylococcus aureus/efeitos dos fármacos , Triterpenos/isolamento & purificação
10.
J Nat Prod ; 74(12): 2571-5, 2011 Dec 27.
Artigo em Inglês | MEDLINE | ID: mdl-22148241

RESUMO

Six novel Ia3-type cyclopeptide alkaloids (1-6) were isolated from stems of Ziziphus apetala. Compound 5 and the known compounds mauritine A (7) and mauritine F (8) were isolated from the roots. Their structures were determined by spectroscopic analyses and chemical methods. The total alkaloids from the roots and the isolated cyclopeptide alkaloids were tested for antidepressant behavior on mice, cytotoxicity, and 11ß-hydroxysteroid dehydrogenase (11ß-HSD) inhibition in vitro. Only mauritine A (7) showed inhibitory activity on 11ß-HSD1, with IC50 values of 52.0 (human) and 31.2 µg/mL (mouse).


Assuntos
11-beta-Hidroxiesteroide Desidrogenases/antagonistas & inibidores , Alcaloides/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Peptídeos Cíclicos/isolamento & purificação , Ziziphus/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Antidepressivos , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Feminino , Humanos , Concentração Inibidora 50 , Camundongos , Peptídeos Cíclicos/química , Peptídeos Cíclicos/farmacologia
11.
J Nat Prod ; 74(10): 2069-80, 2011 Oct 28.
Artigo em Inglês | MEDLINE | ID: mdl-21973054

RESUMO

Twelve new arborinane-type triterpenoids (1-12) and four new anthraquinones (13-16), together with 50 known compounds, were isolated from the roots of Rubia yunnanensis. The structures of 1-16 were elucidated by spectroscopic data analysis and chemical methods. All compounds were evaluated for their cytotoxic, antibacterial, and antifungal activities. Rubiyunnanol C (5) is the first example of an arborinane-type triterpenoid with a double bond at C-8-C-9.


Assuntos
Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Rubia/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Antraquinonas/química , Anti-Infecciosos/química , Antineoplásicos Fitogênicos/química , Candida albicans/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Células HeLa , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Raízes de Plantas/química , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade , Triterpenos/química
12.
Fitoterapia ; 80(6): 361-3, 2009 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-19433133

RESUMO

A new norlignan, (2R,3R,4S,5S)-2,4-bis(4-hydroxyphenyl)-3,5-dihydroxy-tetrahydropyran (1), together with 9 known compounds were isolated from the branches and leaves of Taxodium ascendens. Their structures were mainly determined on the basis of MS, IR, 1D and 2D NMR spectral evidences. Methanol extract showed inhibitory activity on carbonic anhydrase II with an IC(50) value of 4.27 microg/ml, acetone extract and methanol extract inhibited activity of cathepsin B with IC(50) values of 2.12 and 3.71 microg/ml, respectively.


Assuntos
Inibidores da Anidrase Carbônica/isolamento & purificação , Lignanas/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Taxodium/química , Inibidores da Anidrase Carbônica/química , Inibidores da Anidrase Carbônica/farmacologia , Catepsinas/antagonistas & inibidores , Concentração Inibidora 50 , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Folhas de Planta , Caules de Planta
13.
Phytother Res ; 23(6): 885-91, 2009 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-19107858

RESUMO

Inula helianthus-aquatica C. Y. Wu is a traditional medicinal plant used to treat some cancers in folk herbal medicine of Yunnan, China. Bigelovin, a sesquiterpene lactone isolated from this herb, potently inhibits the growth of a panel of eight cancer cell lines, especially in human monoblastic leukemia U937 cells with an IC(50) value of 0.47 microM. Characteristic morphological features of apoptosis were observed in U937 cells treated with bigelovin. Annexin V and nuclear DNA content distribution assays showed that the percentage of Annexin V positive cells increased to 8.86% (24 h) with 1 microM bigelovin treatment, and cells treated with bigelovin at this concentration apparently arrested at G(0)/G(1) phase compared with the control. These data suggested that cytotoxic effect of bigelovin on U937 cells involves induction of apoptosis, and the cell cycle is arrested at G(0)/G(1) phase.


Assuntos
Apoptose/efeitos dos fármacos , Inula/química , Lactonas/farmacologia , Sesquiterpenos/farmacologia , Anexina A5 , Antineoplásicos Fitogênicos/farmacologia , Ciclo Celular/efeitos dos fármacos , Proliferação de Células , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Células U937
14.
Chem Biodivers ; 5(7): 1364-8, 2008 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-18649302

RESUMO

DNA Topoisomerase I can cause DNA breaks and play a key role during cell proliferation and differentiation. It is an important target for anticancer agents. While screening for anticancer compounds, seven natural compounds, 1-7, showed potent cytotoxicities against a panel of ten cancer cell lines. Moreover, an inhibition assay demonstrated that they are also DNA topoisomerase I inhibitors, in which inhibitors 1-5 are new ones.


Assuntos
Antineoplásicos/farmacologia , Inibidores Enzimáticos/farmacologia , Inibidores da Topoisomerase I , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50
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