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1.
Zhongguo Zhong Yao Za Zhi ; 44(11): 2274-2277, 2019 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-31359653

RESUMO

Two sesquiterpenes were isolated from the agarwood originating from Gyrinops salicifolia with various chromatographic techniques, and their structures were determined as 12-hydroxy-dihydrocyperolone(1) and(rel)-4ß,5ß,7ß-eremophil-9-en-12,8α-olide(2), through a combined analysis of physicochemical properties and spectroscopic evidence. Compound 1 was a new compound. Compound 2 showed cytotoxicities against K562 and BEL-7401 cell lines, with IC_(50) values of(17.85±0.04) and(21.82±0.07) mg·L~(-1), respectively [taxol as positive control, with IC_(50) values of(1.97±0.11) and(6.31±0.08) mg·L~(-1)].


Assuntos
Sesquiterpenos/farmacologia , Thymelaeaceae/química , Madeira/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Sesquiterpenos/isolamento & purificação
2.
Fitoterapia ; 137: 104243, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31226283

RESUMO

Two new sesquiterpenoids, leptosphins A (1) and B (2), and a new cyclopiane diterpene, leptosphin C (3), along with four known diterpenes (4-7) were isolated from the solid fermentation cultures of an endophytic fungus Leptosphaeria sp. XL026 isolated from the leaves of Panax notoginseng. Their structures were elucidated by extensive spectroscopic methods and single-crystal X-ray diffraction (data). Compound 1 represents the first sulfur-containing eremophilane sesquiterpene. Compounds 5 and 7 displayed medium antifungal activity against Rhizoctonia cerealis, as well as 6 against Verticillium dahliae Kleb with an MIC value of 12.5 µg/mL. Furthermore, compounds 2, 5, 6 and 7 showed medium antibacterial activity against Bacillus cereus with MIC values of 12.5-6.25 µg/mL, as well as 6 also against Pseudomonas aeruginosa with an MIC value of 12.5 µg/mL.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Ascomicetos/química , Diterpenos/farmacologia , Panax notoginseng/microbiologia , Sesquiterpenos/farmacologia , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , China , Diterpenos/isolamento & purificação , Estrutura Molecular , Folhas de Planta/microbiologia , Sesquiterpenos/isolamento & purificação
3.
Fitoterapia ; 137: 104247, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31247217

RESUMO

A new sesquiterpene glycoside and a new amide have been isolated from the stems of Tinospora sinensis. Their structures were established by 2D NMR spectroscopic techniques (1H,1H-COSY, NOESY, HSQC and HMBC) and mass spectrometry. The isolated compounds were subjected to evaluate neuroprotective activities in vitro. The pre-treatment of two new compounds can significantly ameliorate damage of oxidative stress induced by Aß25-35 and improve PC12 cells survival.


Assuntos
Amidas/farmacologia , Glicosídeos/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Sesquiterpenos/farmacologia , Tinospora/química , Amidas/isolamento & purificação , Animais , Glicosídeos/isolamento & purificação , Estrutura Molecular , Células PC12 , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química , Ratos , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/isolamento & purificação , Tibet
4.
Phytochemistry ; 164: 154-161, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31151062

RESUMO

Oxytropiols A-J, ten undescribed guaiane-type sesquiterpenoids, and the mycotoxin swainsonine (SW) were isolated from the locoweed endophytic fungus Alternaria oxytropis. The chemical structures of these sesquiterpenoids were elucidated on the basis of HR-ESI-MS and NMR data including 1H, 13C, HSQC, 1H-1H COSY, HMBC, and NOESY spectra, and the absolute configurations of these compounds were determined using a modified Mosher's method and X-ray diffraction spectroscopy. A possible biosynthetic pathway of these guaiane-type sesquiterpenoids is discussed, and proposed that post-modification oxidative enzymes might form these highly polyhydroxylated structures. Compound 1 displayed biological effects on the root growth of Arabidopsis thaliana, and SW displayed cytotoxicity against A549 and HeLa cancer cell lines.


Assuntos
Alternaria/química , Antineoplásicos/farmacologia , Micotoxinas/farmacologia , Sesquiterpenos/farmacologia , Swainsonina/farmacologia , Células A549 , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Modelos Moleculares , Conformação Molecular , Micotoxinas/química , Micotoxinas/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade , Swainsonina/química , Swainsonina/isolamento & purificação
5.
Fitoterapia ; 137: 104185, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31150768

RESUMO

Six new and one known dihydroagarofuran sesquiterpenoids esterified with organic acids were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques (UV, IR, MS, NMR, ORD and CD) were used for the structure elucidation of the compounds. The structures of compounds 1 and 2 were confirmed by X-ray single crystallographic analyses. The inhibitory effects on NO production in LPS-induced macrophages of 1-7 were conducted. At 10 µmol/L, compounds 1, 2 and 7 showed moderate inhibitory effects on NO production in LPS-induced macrophages with inhibitory rate at 31.2 ±â€¯3.6, 40.9 ±â€¯4.3, and 66.79 ±â€¯3.1%, respectively.


Assuntos
Macrófagos/efeitos dos fármacos , Sesquiterpenos/farmacologia , Tripterygium/química , Animais , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
6.
Phytochemistry ; 165: 112047, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31203102

RESUMO

Four undescribed lignans and two undescribed sesquiterpenic acids, together with three known compounds (hypochoeroside C, hypochoeroside D, and 5-O-caffeoylshikimic acid) were isolated from the roots of Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae). The lignans were identified as 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranosyl-2'-O-methacrylate, (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one, and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid. The two sesquiterpenic acids were identified as the ring open precursors of hypochoerosides C and D. Structures were elucidated using NMR and HRMS. Absolute configurations of (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid were determined using electronic circular dichroism (ECD) spectroscopy. 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside was evaluated for its anti-proliferative activity against myeloma cell lines MM1S, U266, and NCI-H929 and showed cytotoxicity at 100 mM against MM1S strain. No neurotoxicity was observed for major compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, hypochoeroside C, and hypochoeroside D in a fluorescence assay measuring neurite outgrowth in dorsal root ganglion (DRG) neurons. Additionally, compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, hypochoeroside C, hypochoeroside D, and hypochoerosidic acid D were quantified in unstressed and drought-stressed plants using HPLC-DAD. Drought-stressed plants were found to contain lower concentrations of the lignan 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside and sesquiterpene lactone hypochoeroside C.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Lactonas/farmacologia , Lignanas/farmacologia , Mieloma Múltiplo/tratamento farmacológico , Sesquiterpenos/farmacologia , 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 , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Lignanas/química , Lignanas/isolamento & purificação , Estrutura Molecular , Mieloma Múltiplo/patologia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
7.
J Chromatogr A ; 1602: 188-198, 2019 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-31147156

RESUMO

A liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS)-based dereplicative method was developed for identifying oplopane- and bisabolane-type sesquiterpenoids from buds of Tussilago farfara L. The analysis of these chemical analogues, sesquiterpene esters, is challenging by MS-based nontargeted metabolomic approaches because of their in-source fragmentation and structural diversity. To profile these sesquiterpenoids, four diagnostic ions (m/z 215.143, 217.158, 229.123, and 231.138) were suggested in the positive ion mode and the developed method utilized two sequential MS/MS scan modes to identify common skeletons and investigate the fragmentation patterns of their parent molecules. Precursor ion scan by triple quadrupole MS/MS provided the parent molecular ions from their diagnostic ions, and product ion scan by quadrupole time-of-flight MS/MS confirmed their fragmentation behaviors. Under the optimized UHPLC-MS/MS method, 74 sesquiterpenoids were characterized from the Farfarae Flos and 11 compounds were isolated for the method validation. Among those compounds, three sesquiterpenoids were newly separated from the Farfarae Flos. Furthermore, the diagnostic ions and the MS/MS fragment behaviors were applied to the accurate quantification of the 8 isolated sesquiterpenoids. Therefore, the developed LC-MS/MS-based method highlighted the chemical composition of the Farfarae Flos and could be extended to the screening and quantification of other sesquiterpene esters.


Assuntos
Técnicas de Química Analítica/métodos , Espectrometria de Massas , Sesquiterpenos/química , Tussilago/química , Cromatografia Líquida , Íons/química , Sesquiterpenos/isolamento & purificação
8.
Chem Biodivers ; 16(8): e1900278, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31207097

RESUMO

Using synthetic chemicals in industry and agriculture has led to several environmental problems. Thus, plant products derived from volatile oils (VOs) could be a potential green source for bioherbicides. Little is known about the VOs of Lactuca serriola. Hence, the present study aimed to characterize the VOs chemical composition from the aerial parts of L. serriola, assessment of antioxidant activity, and evaluate allelopathic potential against the noxious weed Bidens pilosa. The VOs were extracted by hydrodistillation and analyzed by GC/MS. The VOs from the Egyptian ecospecies of L. serriola were found to comprise 34 compounds mainly oxygenated sesquiterpenes and diterpenes. The major compounds were isoshyobunone (64.22 %), isocembrol (17.35 %), and alloaromadendrene oxide-1 (7.32 %). So, L. serriola can be considered as a good source for isoshyobunone, considering that it has a much higher concentration than any other plants. Also, this plant has a high content of the oxygenated diterpene compound, isocembrol, which is rarely found in the VOs of most plants. The VOs expressed strong antioxidant activity. Also, for the first time, our results showed a strong allelopathic activity of VOs from L. serriola on germination and seedling growth of the noxious weed, B. pilosa. We suppose that the activity of the VOs from L. serriola could be attributed to these previously mentioned major compounds, as they represent about 89 % of the total identified oil constituents. Nevertheless, to evaluate these compounds as new allelochemicals, further study is needed to test the allelopathic activity of authenticated standard of these compounds either singular or in combination on several weeds as well as evaluate the safety, and improve the efficacy and stability at the field scale.


Assuntos
Antioxidantes/química , Asteraceae/química , Diterpenos/química , Óleos Voláteis/química , Sesquiterpenos/química , Asteraceae/metabolismo , Bidens/crescimento & desenvolvimento , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Germinação/efeitos dos fármacos , Óleos Voláteis/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
9.
Microb Pathog ; 135: 103604, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31247257

RESUMO

The present study describes the possibility of using some essential oils and monoterpens as bioagents against the growth of Ralstonia solanacearum, a causal bacterium of potato brown rot disease. Eight isolates of the bacterium were recovered from infected potato tubers, showing typical symptoms of the disease, Isolates were identified as R.solanacearum phylotype II, based on biochemical and physiological characteristics, as well as, at the molecular level through PCR analysis. Three essential oils extracted from Corymbia citriodora (leaves), Cupressus sempervirens (aerial parts), and Lantana camara (aerial parts) were evaluated for their antibacterial activity against eight isolates of R. solanacearum phylotype II. Results demonstrated that L. camara essential oil (concentration 5000 µg/mL) had the highest effects against the RsMo2, RsSc1 and Rs48, with inhibition zone (IZ) values of 17.33, 16.33, and 17.50 mm, respectively, also against Rs2 (IZ 14.33 mm), and RsIs2 (IZ 16 mm). C. citriodora oil showed the highest activity against RsBe2 (IZ 14 mm), RsFr4 (IZ 13.66 mm) and RsNe1 (IZ 13.66 mm). Gas Chromatography-Mass Spectrometry (GC-MS-FID) analyzed the chemical composition of these essential oils. It was proved that L. camara leaves contains mainly trans-caryophyllene (16.24%) and α-humulene (9.55%), in C. citriodora oil were α-citronellal (56.55%), α-citronellol (14.89%), and citronellol acetate (13.04%), and in Cup. sempervirens aerial parts were cedrol (22.17%), and Δ3-carene (18.59%). Five monoterpenes were evaluated against the most resistance Ralstonia isolate RsFr5 to the three studied essential oils and found that limonene had the highest effect against it compared with the lowest thymol. The results proved the strong bio effects of the essential oil from L. camara leaves as a natural product contained monoterpenes that can inhibit the growth of tested R. solanacearum phylotype II isolates.


Assuntos
Antibacterianos/farmacologia , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Ralstonia solanacearum/efeitos dos fármacos , Solanum tuberosum/microbiologia , Aldeídos/isolamento & purificação , Aldeídos/farmacologia , Antibacterianos/isolamento & purificação , Cupressus/química , DNA Bacteriano/análise , Cromatografia Gasosa-Espectrometria de Massas , Lantana/química , Testes de Sensibilidade Microbiana , Monoterpenos/isolamento & purificação , Myrtaceae/química , Octanóis/isolamento & purificação , Octanóis/farmacologia , Óleos Voláteis/isolamento & purificação , Doenças das Plantas/microbiologia , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Ralstonia solanacearum/crescimento & desenvolvimento , Ralstonia solanacearum/isolamento & purificação , Ralstonia solanacearum/fisiologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
10.
Molecules ; 24(9)2019 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-31035334

RESUMO

As part of our continual efforts to exploit 'Tujia Ethnomedicine' for their pharmacophoric functionalities, we herein investigated Kadsura heteroclita collected from a deep Wulin mountain area in northern Hunan province. The current study resulted in the isolation of three new sesquiterpenes: 6α,9α,15-trihydroxycadinan-4-en-3-one (1), (+)-3,11,12-trihydroxycalamenene (2), (-)-3,10,11,12-tetrahydroxy-calamenene (3), along with four known sesquiterpenes (4-7), and a cytochalasin H (8). Their chemical structures were elucidated by 1D-, and 2D-NMR spectroscopy, and HRESI-MS, CD spectrometry. The antioxidant, and cytotoxic activities of the compounds were evaluated. Compound 8 exhibited a strong antioxidant effect with an IC50 value of 3.67 µM on isolated human polymorphonuclear cells or neutrophils.


Assuntos
Kadsura/química , Extratos Vegetais/química , Caules de Planta/química , Sesquiterpenos/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
11.
Mar Drugs ; 17(5)2019 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-31035351

RESUMO

Seven previously unreported cyclonerane derivatives, namely, 3,7,11-trihydroxycycloneran-10-one, cycloneran-3,7,10,11-tetraol, cycloneran-3,7,11-triol, 11,12,15-trinorcycloneran-3,7,10-triol, 7,10S-epoxycycloneran-3,15-diol, 7,10R-epoxycycloneran-3,15-diol, and (10Z)-15-acetoxy-10-cycloneren-3,7-diol, were isolated in addition to the known (10Z)-cyclonerotriol, (10E)-cyclonerotriol, catenioblin C, and chokol E from the culture of Trichoderma asperellum A-YMD-9-2, an endophytic fungus obtained from the marine red alga Gracilaria verrucosa. The structures of previously unreported compounds were established by spectroscopic techniques, including 1D/2D NMR, MS, and IR. The isolation of these new cyclonerane derivatives greatly adds to the structural diversity of unusual cyclonerane sesquiterpenes, and several isolates exhibit potent inhibition against some marine phytoplankton species.


Assuntos
Endófitos/química , Gracilaria/microbiologia , Sesquiterpenos/química , Trichoderma/química , Animais , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fitoplâncton/efeitos dos fármacos , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Zooplâncton/efeitos dos fármacos
12.
Fitoterapia ; 136: 104170, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31085308

RESUMO

A total of thirteen sesquiterpenoids with diverse skeletons including four new sesquiterpenoids, glandulosines A - D (1-4), a new natural product, glandulosine E (5), and eight known sesquiterpene lactones (6-13) were isolated from the roots of Cichorium glandulosum Boiss. et Huet (Asteraceae). Their structures were determined by extensive spectroscopic experiments including NMR, electronic circular dichroism (ECD), calculated ECD, Rh2(OCOCF3)4-induced ECD, and single-crystal X-ray diffraction analysis, as well as chemical methods. This is the first report of the crystal structure of 11ß,13-dihydrolactucin (11). Thirteen isolated sesquiterpenoids (1-13) were evaluated for their anti-inflammatory activities in vitro, and three guaiane sesquiterpene lactones, glandulosine E (5), scorzoside (9), and lactucin (10) showed moderate inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages.


Assuntos
Anti-Inflamatórios/farmacologia , Asteraceae/química , Raízes de Plantas/química , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , China , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
13.
Fitoterapia ; 137: 104151, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30999024

RESUMO

The norbisabolane-type sesquiterpenoids bearing a spiroketal functionality have been found in Phyllanthus spp. and showed anti-HBV activities. As part of an ongoing effort to search for promising anti-HBV sesquiterpenes from Phyllanthus plants, we report four new norbisabolane-type sesquiterpenoids, phyacidusin A (1), phyacidusin B (2), phllanthacidoid A1 (3) and phllanthacidoid N1 (4), from stem of P. acidus collected in Xishuangbanna, Yunnan province, China. The absolute configuration of new compounds was established by coupling constants and ROESY correlations, as well as comparation of NMR data with those of known compounds. The absolute configuration of new compounds 1 and 2 was further confirmed by X-ray diffraction. Compound 2 showed effect to HBsAg with an IC50 value of 11.2 ±â€¯0.01 µM, while compound 3 inhibited HBeAg secretion with an IC50 value of 57.1 ±â€¯0.02 µM. The results enriched the diversity of anti-HBV norbisabolane sesquiterpenes.


Assuntos
Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Phyllanthus/química , Sesquiterpenos/farmacologia , Antivirais/isolamento & purificação , China , Células Hep G2 , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química , Sesquiterpenos/isolamento & purificação
14.
Molecules ; 24(8)2019 Apr 18.
Artigo em Inglês | MEDLINE | ID: mdl-31003442

RESUMO

Objective: To develop an accurate and rapid ultra-performance liquid chromatography (UPLC) coupled with a photodiode array (PDA) method for the simultaneous determination of artemisinin (Art), arteannuin B (Art B), arteannuin C (Art C), dihydroartemisinic acid (DHAA) and artemisinic acid (AA) in Artemisia annua L. Methodology: Chromatography separation was performed on an ACQUITY UPLC BEH C18 Column with isocratic elution; the mobile phase was 0.1% formic acid aqueous solution (A) and acetonitrile (B) (A:B = 40:60, v/v). Data were recorded at an ultraviolet (UV) wavelength of 191 nm for Art, Art C, DHAA and AA, and 206 nm for Art B. Results: The calibration curves of the five sesquiterpene components were all linear with correlation coefficients more than 0.9990. The linear ranges were 31.44-1572 µg/mL, 25.48-1274 µg/mL, 40.56-2028 µg/mL, 31.44-1572 µg/mL and 26.88-1396 µg/mL for Art, Art B, Art C, DHAA and AA, respectively. The precision ranged from 0.08% to 2.88%, the stability was from 0.96% to 1.66%, and the repeatability was all within 2.42% and had a mean extraction recovery of 96.5% to 100.6%. Conclusion: The established UPLC-PDA method would be valuable for improving the quantitative analysis of sesquiterpene components in Artemisia annua L.


Assuntos
Artemisia annua/química , Bioensaio/métodos , Cromatografia Líquida de Alta Pressão/métodos , Óptica e Fotônica/instrumentação , Sesquiterpenos/análise , Sesquiterpenos/isolamento & purificação , Ultrassom/métodos , Extratos Vegetais/análise , Análise de Regressão , Reprodutibilidade dos Testes
15.
Org Lett ; 21(9): 3286-3289, 2019 05 03.
Artigo em Inglês | MEDLINE | ID: mdl-31008606

RESUMO

Rhodatin (1), a meroterpenoid featuring a unique pentacyclic scaffold with both spiro and spiroketal centers, and five unusual acorane-type sesquiterpenoids, named rhodocoranes A-E (2-6, respectively), are the first natural products isolated from the basidiomycete Rhodotus palmatus. Their structures were elucidated by two-dimensional NMR experiments and HRESIMS, while the absolute configuration of the substance family was determined by Mosher's method utilizing 2. Rhodatin strongly inhibited hepatitis C virus, whereas 4 displayed cytotoxicity and selective antifungal activity.


Assuntos
Antivirais/isolamento & purificação , Basidiomycota/química , Terpenos/isolamento & purificação , Antivirais/farmacologia , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Hepacivirus/efeitos dos fármacos , Humanos , Estrutura Molecular , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Compostos de Espiro/química , Compostos de Espiro/farmacologia , Terpenos/farmacologia
16.
Fitoterapia ; 135: 79-84, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30995565

RESUMO

Six 8,12-epoxyguaiane sesquiterpenes (1-6), together with two known 2-(2-phenylethyl)chromone derivatives (7-8) were isolated from agarwood originating from Aquilaria filaria. Their structures were established by spectroscopic methods including IR, HRESIMS, 1D, and 2D NMR, and comparison with the published data. The absolute configuration of compound 1 was unambiguously determined by quantum chemical calculation of the electronic circular dichroism (ECD) spectrum. All compounds were tested for their α-glucosidase inhibitory activity and cytotoxicity. Compound 5 showed significant α-glucosidase inhibitory activity with IC50 value of 253.2 ±â€¯9.7 µM (Acarbose, 743. 4 ±â€¯3.3 µM). Compounds 2-4 displayed weak cytotoxicity against K562 tumor cell lines.


Assuntos
Inibidores de Glicosídeo Hidrolases/farmacologia , Sesquiterpenos de Guaiano/farmacologia , Sesquiterpenos/farmacologia , Thymelaeaceae/química , Sobrevivência Celular/efeitos dos fármacos , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Humanos , Células K562 , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação , Madeira/química
17.
Fitoterapia ; 135: 27-32, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30946944

RESUMO

Five new compounds, including one bisabolane-type sesquiterpenoids, namely aspergillusene D (1), two new xanthones (2 and 3), and two new catecholderivatives (4 and 5), together with fourteen known compounds (6-19), were isolated and identified from the fungus Aspergillus sydowiiSCSIO 41,301 from the sponge Phakellia fusca. Their structures and absolute configurations were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. Most of the isolated compounds (1-3, and 6-19) were evaluated for their antiviral, cytotoxic, and antibacterial activities. Among them, new compounds 2 and 3 displayed obvious selective inhibitory activities against two influenza A virus subtypes, including A/Puerto Rico/8/34 (H1N1) and A/FM-1/1/47 (H1N1), with IC50 values ranging from 2.17 ±â€¯1.39 to 4.70 ±â€¯1.11 µM.


Assuntos
Antibacterianos/farmacologia , Antivirais/farmacologia , Aspergillus/química , Policetídeos/farmacologia , Poríferos/microbiologia , Sesquiterpenos/farmacologia , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antivirais/química , Antivirais/isolamento & purificação , Vírus da Influenza A Subtipo H1N1/efeitos dos fármacos , Estrutura Molecular , Policetídeos/química , Policetídeos/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
18.
Fitoterapia ; 135: 22-26, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30946945

RESUMO

Four new sesquiterpenoids,including three nor-cinalbicane type sesquiterpenoids, named Jasminol A, G, H (1-3) and one eremophilene-type sesquiterpenoid, named Jasminol B (4) together with nine known compounds (5-13) were isolated from the stems of Jasminum officinale L. The structures of new compound were elucidated on the base of IR, HR-ESI-MS, 1D NMR, 2D NMR and DEPT analysis, and the absolute configurations were determined by single-crystal X-ray diffraction analysis. In addition, the anti-inflammatory activity of isolated compounds was evaluated using lipopolysaccharide (LPS)-induced murine macrophage RAW264.7, and compounds 1-4 exhibited a moderate inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 cells with IC50 values of 20.56 ±â€¯1.31, 30.12 ±â€¯0.89, 30.35 ±â€¯2.72 and 31.60 ±â€¯1.69 µM, respectively, and CC50 values >200 uM.


Assuntos
Anti-Inflamatórios/farmacologia , Jasminum/química , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Caules de Planta/química , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
19.
Anaerobe ; 57: 99-106, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30953693

RESUMO

Enterotoxigenic Bacteroides fragilis (ETBF) can form biofilms in the colon mucosal membrane and may promote chronic infection and tumor formation. The objective of this study was to determine the effect of zerumbone extracted from Zingiber zerumbet (L.) Smith, on B. fragilis biofilm formation. Inhibitory effects of zerumbone on planktonic cell growth and biofilm formation were examined by crystal-violet biofilm assays and XTT metabolic assays. Results showed that zerumbone significantly inhibited biofilm formation and eradicated established biofilms. Furthermore, B. fragilis biofilms inhibited by zerumbone were observed by confocal laser scanning microscopy. qRT-PCR was used to support the phenotypic results and to investigate the expression levels of an efflux pump-related gene (bmeB). Specifically, among the efflux pump-related genes, zerumbone significantly suppressed the expression level of bmeB12. These results indicate that zerumbone might be a promising candidate as an anti-biofilm and antimicrobial agent to treat and prevent biofilm-related infections caused by B. fragilis.


Assuntos
Antibacterianos/farmacologia , Bacteroides fragilis/efeitos dos fármacos , Biofilmes/efeitos dos fármacos , Sesquiterpenos/farmacologia , Antibacterianos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Perfilação da Expressão Gênica , Proteínas de Membrana Transportadoras/análise , Testes de Sensibilidade Microbiana , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Sesquiterpenos/isolamento & purificação , Zingiberaceae/química
20.
Nat Commun ; 10(1): 1892, 2019 04 23.
Artigo em Inglês | MEDLINE | ID: mdl-31015442

RESUMO

The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C, D, I, chlorajaponilide C, multistalide B, sarcandrolide J and sarglabolide I. In particular, we present a unified dimerization strategy utilizing a base-mediated thermal [4 + 2] cycloaddition between a common furyl diene, generated in situ, and various types of dienophiles. Accordingly, all the three types of lindenane [4 + 2] dimers with versatile biological activities are accessible, which would stimulate future probing of their pharmaceutical potential.


Assuntos
Técnicas de Química Sintética , Magnoliopsida/química , Sesquiterpenos/síntese química , China , Reação de Cicloadição , Dimerização , Magnoliopsida/metabolismo , Estrutura Molecular , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação
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