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1.
Molecules ; 24(17)2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31438610

RESUMO

The resins bled from stems and in seed cones and leaves of Cryptomeria japonica, Glyptostrobus pensilis, Taxodium distichum, and T. mucronatum were characterized to provide an overview of their major natural product compositions. The total solvent extract solutions were analyzed as the free and derivatized products by gas chromatography-mass spectrometry to identify the compounds, which comprised minor mono- and sesquiterpenoids, and dominant di- and triterpenoids, plus aliphatic lipids (e.g., n-nonacosan-10-ol). Ferruginol, 7α-p-cymenylferruginol, and chamaecydin were the major characteristic markers for the Taxodioideae conifer subfamily. The mass spectrometric data can aid polar compound elucidation in environmental, geological, archeological, forensic and pharmaceutical studies.


Assuntos
Cupressaceae/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Taxodium/química , Terpenos/análise
2.
Carbohydr Polym ; 213: 276-285, 2019 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-30879670

RESUMO

The structure and bioactivity of a novel polysaccharide from Platycladus orientalis (L.) Franco leaves (POP2) were investigated in the present study. Structure characterization demonstrated that the average molecular weight of POP2 was 9.69 kDa and consisted of arabinose (14.39%), mannose (10.24%), glucose (63.95%) and galactose (11.42%). The main linkage types of POP2 consisted of (1→4)-linked α-d-Glc and (1→6)-linked α-d-Glc based on methylation and NMR analysis. Bioactivity evaluation showed that POP2 could effectively promote the secretion of inflammatory cytokines (IL-6 and TNF-α), as well as the anti-inflammatory cytokines (IL-10) in LPS-induced cells. Besides, the secretion of NO was significantly inhibited by POP2 in M1 model. POP2 could enhance the level of inflammatory cytokines (NO, IL-6 and TNF-α), while the secretion of the anti-inflammatory cytokine TGF-ß was markedly suppressed in IL-4 induced cells. Our work attempted to elucidate the regulation of macrophage polarization and support the potential application of POP2 as bioactive ingredient for functional foods.


Assuntos
Cupressaceae/química , Macrófagos/efeitos dos fármacos , Polissacarídeos/farmacologia , Animais , Polaridade Celular/efeitos dos fármacos , Células Cultivadas , Macrófagos/metabolismo , Camundongos , Folhas de Planta/química , Polissacarídeos/química , Polissacarídeos/isolamento & purificação , Células RAW 264.7
3.
Phytochemistry ; 161: 86-96, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30822624

RESUMO

A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231 cell line with IC50 value of 20.02 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cupressaceae/química , Diterpenos/farmacologia , Casca de Planta/química , Caules de Planta/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Modelos Moleculares , Conformação Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
4.
J Food Sci ; 84(3): 667-677, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30779137

RESUMO

The polyphenols (PF) from Platycladus Orientalis (L.) Franco leaves were purified by using 10 different macroporous adsorption resins. HPD-722 resin showed the best adsorption and desorption capacities. The static and dynamic adsorption and desorption of PF on HPD-722 resin were studied and the total polyphenols were separated into two fractions, PF-A and PF-B. PF-A and PF-B demonstrated similar scavenging activity of free radical (DPPH, ABTS, hydroxyl radical, superoxide anion). The scavenging activity of PF-A and PF-B on hydroxyl radical and superoxide anion radical reached the equal levels of vitamin C and gallic acid. The IC50 value of PF-A for hydroxyl radical scavenging activity and superoxide anion radical scavenging activity were 0.50 and 0.56 mg/mL, while those of PF-B were 0.61 and 0.64 mg/mL. PF-A and PF-B could reduce the overproduction of inflammatory cytokines (TNF-α, Pro-IL-1ß, and IL-6) induced by lipopolysaccharide and their protein expression in THP-1 cells. PF-B exhibited better anti-inflammatory effect than PF-A in the dosage range of 1.0-4.0 µg/mL. Structural identification of PF-A and PF-B were conducted by HPLC-MS/MS. Ten polyphenol compounds were identified in PF-A and PF-B, respectively, by HPLC-MS/MS, including quercetin, apigenin, myricetin, and so on. Molecular docking studies indicated that apigenin, myricetin, luteolin, kaempferol, and quercetin effectively inhibit xanthine oxidase by forming hydrogen bonds with the amino acid residues and binding to the active site of the enzyme. The results might supply useful information for better understanding the chemical structure, antioxidant, and anti-inflammatory activities of Platycladuso (L.) Franco leaves polyphenols. PRACTICAL APPLICATION: This study demonstrated that polyphenols from P. orientalis (L.) Franco leaves have the potential applications as functional food ingredient for the prevention and treatment of gout and inflammation, hyperuricemia and gout.


Assuntos
Cupressaceae/química , Polifenóis/química , Antioxidantes , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Citocinas/genética , Citocinas/metabolismo , Depuradores de Radicais Livres , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Simulação de Acoplamento Molecular , Extratos Vegetais , Folhas de Planta/química , Superóxidos , Espectrometria de Massas em Tandem
5.
Phytomedicine ; 56: 57-63, 2019 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-30668354

RESUMO

BACKGROUND: Tetraclinis articulata is used in traditional medicine and has been reported to possess antibacterial, antifungal, cytotoxic, anti-inflammatory and antioxidant properties. PURPOSE: This study investigated the effects of T. articulata essential oil on memory and brain oxidative stress in amyloid-ß peptide 1-42 (Aß1-42)-induced an Alzheimer's disease amyloidosis model. Moreover, the underlying mechanism for memory enhancement and antioxidant activity was investigated, thus supporting its traditional use with scientific evidence for further studies. METHODS: T. articulata essential oil was administered by inhalation to male Wistar rats once daily for 15 min period at doses of 1% and 3% for 21 days after the intracerebroventricular administration of Aß1-42 right-unilaterally to induce memory deficits. The chemical composition of the essential oil was done by GC-MS and GC-FID. Spatial memory of rats was tested using Y-maze and radial arm maze tests. The possible underlying mechanism for memory improvement exhibited by T. articulata essential oil was investigated by in vivo brain antioxidant effect and acetylcholinesterase (AChE) inhibitory effect. In vitro, experimental evaluations were assessed through DPPH and ABTS tests. RESULTS: The GC-MS and GC-FID data showed that the essential oil has a high percent of monoterpene hydrocarbons. Also, we demonstrated the essential oil reversed the Aß1-42-induced decreasing of the spontaneous alternation in the Y-maze test and the Aß1-42-induced increasing of the working and reference memory errors in the radial arm maze test. Furthermore, the Aß1-42-decreased the acetylcholinesterase activity and the oxidant-antioxidant status in the rat hippocampus was retrieved by the treatment with the essential oil. CONCLUSION: The study demonstrates that the essential oil could be a potent pharmacological agent against dementia by modulating cholinergic activity and promoting antioxidant action in the rat hippocampus.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Encéfalo/efeitos dos fármacos , Transtornos Cognitivos/tratamento farmacológico , Cupressaceae/química , Óleos Voláteis/farmacologia , Doença de Alzheimer/metabolismo , Doença de Alzheimer/fisiopatologia , Peptídeos beta-Amiloides/toxicidade , Amiloidose/induzido quimicamente , Animais , Antioxidantes/farmacologia , Encéfalo/metabolismo , Encéfalo/fisiopatologia , Inibidores da Colinesterase/farmacologia , Transtornos Cognitivos/metabolismo , Disfunção Cognitiva/tratamento farmacológico , Modelos Animais de Doenças , Masculino , Transtornos da Memória/tratamento farmacológico , Óleos Voláteis/química , Estresse Oxidativo/efeitos dos fármacos , Fragmentos de Peptídeos/toxicidade , Ratos Wistar , Memória Espacial/efeitos dos fármacos
6.
Molecules ; 23(12)2018 Dec 19.
Artigo em Inglês | MEDLINE | ID: mdl-30572688

RESUMO

The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been reported. Results show that diterpenoids were the most abundant components and callitrisic acid was present in the resin extracts of all Callitris species analyzed. Significant amounts of 4-epi-pimaric and sandaracopimaric acids, with lesser communic, ozic, and lambertianic acids, were also in the mixtures. Phenolic diterpenoids, for example, ferruginol, hinokiol, were found in trace quantities in some samples. Thus, callitrisic acid and 4-epi-pimaric acid are the characteristic diterpenoids of Callitris species that are amenable to molecular biomarker analyses in geological or environmental applications.


Assuntos
Cupressaceae/química , Resinas Vegetais/química , Terpenos/química , Cromatografia Gasosa-Espectrometria de Massas
7.
J Opt Soc Am A Opt Image Sci Vis ; 35(10): 1769-1779, 2018 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-30462098

RESUMO

Conceptually, biological cells are dielectric, photonic resonators that are expected to show a rich variety of shape resonances when exposed to electromagnetic radiation. For spheroidal cells, these shape resonances may be predicted and analyzed using the Mie theory of dielectric spheres, which predicts that a special class of resonances, i.e., whispering gallery modes (WGMs), causes ripples in the absorbance spectra of spheroidal cells. Indeed, the first tentative indication of the presence of Mie ripples in the synchrotron Fourier transform infrared (SFTIR) absorbance spectra of Juniperus chinensis pollen has already been reported [Analyst140, 3273 (2015)ANLYAG0365-488510.1039/C5AN00401B]. To show that this observation is no isolated incidence, but a generic spectral feature that can be expected to occur in all spheroidal biological cells, we measured and analyzed the SFTIR absorbance spectra of Cunninghamia lanceolata, Juniperus chinensis, Juniperus communis, and Juniperus excelsa. All four pollen species show Mie ripples. Since the WGMs causing the ripples are surface modes, we propose ripple spectroscopy as a powerful tool for studying the surface properties of spheroidal biological cells. In addition, our paper draws attention to the fact that shape resonances need to be taken into account when analyzing (S)FTIR spectra of isolated biological cells since shape resonances may distort the shape or mimic the presence of chemical absorption bands.


Assuntos
Pólen/química , Espectroscopia de Infravermelho com Transformada de Fourier/instrumentação , Síncrotrons , Cupressaceae/química
8.
Org Biomol Chem ; 16(46): 9059-9063, 2018 11 28.
Artigo em Inglês | MEDLINE | ID: mdl-30444234

RESUMO

Biogenesis-inspired chemical research of the leaves of Taiwania cryptomerioides afforded four unprecedented dimeric diterpenes, featuring a tetracyclic [7. 75, 9. 4. 05, 10. 08, 9] octodecane core: taiwanoids A-D (1-4). The structures of these compounds were determined on the basis of comprehensive spectral analysis, chemical conversions and X-ray crystallography. A possible biosynthetic pathway for compounds 1-4 was proposed. Compounds 2 and 3 exerted a 5.37 and 6.26-fold potentiation effect on bortezmib (BTZ) susceptibility at a tested concentration of 20 µM, respectively.


Assuntos
Abietanos/química , Cupressaceae/química , Abietanos/farmacologia , Antineoplásicos/farmacologia , Bortezomib/farmacologia , Linhagem Celular Tumoral , Cristalografia por Raios X , Dimerização , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Humanos , Modelos Moleculares , Neoplasias/tratamento farmacológico , Extratos Vegetais/química , Extratos Vegetais/farmacologia
9.
Chem Biodivers ; 15(8): e1800148, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29790302

RESUMO

A comprehensive phytochemical study of Juniperus turbinata (Cupressaceae) collected from La Maddalena Archipelago (Sardinia, Italy) is reported. Both the essential oil and the ethanolic extract obtained from the aerial parts were analyzed. The essential oil appears to belong to a new chemotype compared to other Mediterranean juniper accessions, as it was favored by geographic isolation of the isles. It showed a low content of monoterpene hydrocarbons and α-terpineol, ent-manoyl oxide, 1,10-di-epi-cubenol as the major constituents. The ethanolic fraction contained mainly diterpenoids. Among these, 15-formyloxyimbricatolic acid (7) is a new natural product since it has hitherto been obtained only by synthetic route. The phenolic fraction contained biflavonoids: cupressuflavone (9), followed by minor amounts of amentoflavone (10) and hinokiflavone (11). The essential oil and six purified compounds (1 - 4, 8 and 9) were assessed for biological activities, namely antioxidant (assessed by DPPH· , ABTS·+ and FRAP methods) and cytotoxic effects towards selected human tumor cell lines (MDA-MB 231, A375 and HCT116 cells). Compound 3 exhibited higher radical scavenging activity against ABTS·+ radical than the reference Trolox. Noteworthy, compound 8 showed powerful effects towards tumor cell lines, with IC50 values in the range of 0.060 - 0.201 µm, which make it a promising anticancer drug candidate.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Cupressaceae/química , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Radicais Livres/antagonistas & inibidores , Humanos , Itália , Conformação Molecular , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Relação Estrutura-Atividade
10.
J Pharm Biomed Anal ; 152: 271-278, 2018 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-29448222

RESUMO

Helicobacter pylori is a major infective etiological agent of the upper gastrointestinal tract diseases. The bacterium exhibits resistance to various conventional antibiotics, being usually challenging for eradication. Since there is an urge to consider alternative therapeutic strategies, the aim of the study was to examine selected essential oils of plants belonging to families Cupressaceae (Juniperus communis) and Lamiaceae (Hyssopus officinalis, Salvia officinalis, Melissa officinalis, Lavandula angustifolia, Ocimum basilicum and Thymus serpyllum) against H. pylori, using an improved microdilution broth method. The oils were examined in concentration range from 0.03 to 4 µL/mL. The method comprises Brain-heart infusion broth supplemented with yeast extract, horse serum and IsoVitaleX. After 3 day incubation, an equal volume of double strengthen Christensen's urea was added into each well and incubated for additional 4 h. In wells with present H. pylori, the medium changed color from yellow to purple, allowing MIC determination even without a microtitre plate reader. The microtitre format method is convenient as it is less expensive, easier to perform and requires less amount of an anti-H. pylori agent. The improved method enhances specificity to H. pylori, as fast urease activity is almost an exclusive property of this bacterium. The application of the second step incubation with Christensen's urea decreases the possibility of false positive/negative results due to contaminant growth or commonly poor H. pylori growth. Among the examined oils, J. communis, H. officinalis and O. basilicum were not active with the highest applied concentrations, while the most active was T. serpyllum, with MIC 2.0-4.0 µL/mL. This is the first report on essential oils activity of T. serpyllum and H. officinalis against H. pylori.


Assuntos
Anti-Infecciosos/farmacologia , Helicobacter pylori/efeitos dos fármacos , Colorimetria/métodos , Meios de Cultura/farmacologia , Cupressaceae/química , Lamiaceae/química , Testes de Sensibilidade Microbiana , Óleos Voláteis/farmacologia , Óleos Vegetais/farmacologia
11.
J Asian Nat Prod Res ; 20(11): 1075-1080, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28944690

RESUMO

A new diterpenoid, 17-methyl-8, 13-labdadien-15, 16-olid-19-oic acid methyl ester (1), along with two known compounds 2 and 3, were isolated from the leaves of Platycladus orientalis (L.) Franco. The structures were confirmed based on the analysis of HR-MS, 1D-NMR, and 2D-NMR spectra and the configuration of 1 was confirmed by the single-crystal X-ray diffraction.


Assuntos
Cupressaceae/química , Diterpenos/química , Folhas de Planta/química , Modelos Moleculares , Estrutura Molecular
12.
J Chromatogr Sci ; 56(1): 41-48, 2018 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-28977346

RESUMO

Platycladi cacumen (dried twigs and leaves of Platycladus orientalis (L.) Franco) is a frequently utilized Chinese medicinal herb. To evaluate the quality of the phytomedcine, an ultra-performance liquid chromatographic method with diode array detection was established for chemical fingerprinting and quantitative analysis. In this study, 27 batches of P. cacumen from different regions were collected for analysis. A chemical fingerprint with 20 common peaks was obtained using Similarity Evaluation System for Chromatographic Fingerprint of Traditional Chinese Medicine (Version 2004A). Among these 20 components, seven flavonoids (myricitrin, isoquercitrin, quercitrin, afzelin, cupressuflavone, amentoflavone and hinokiflavone) were identified and determined simultaneously. In the method validation, the seven analytes showed good regressions (R ≥ 0.9995) within linear ranges and good recoveries from 96.4% to 103.3%. Furthermore, with the contents of these seven flavonoids, hierarchical clustering analysis was applied to distinguish the 27 batches into five groups. The chemometric results showed that these groups were almost consistent with geographical positions and climatic conditions of the production regions. Integrating fingerprint analysis, simultaneous determination and hierarchical clustering analysis, the established method is rapid, sensitive, accurate and readily applicable, and also provides a significant foundation for quality control of P. cacumen efficiently.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Cupressaceae/química , Medicamentos de Ervas Chinesas , Análise por Conglomerados , Medicamentos de Ervas Chinesas/análise , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/normas , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos Testes
13.
Environ Sci Pollut Res Int ; 24(36): 27746-27754, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29098586

RESUMO

The sandarac resin (Tetraclinis articulata) has been long used for its properties, mostly as a varnish component. Called juniper resin until the nineteenth century, the real botanical origin of sandarac is still unclear. The first approach to this issue is the review of the evolution of the etymology, terminology, and botanical description of sandarac through time. It seems that sandarac was mainly coming from T. articulata but the use of some juniper resins before the twentieth century is not to be excluded. The second approach is a chemical one; we used gas chromatography coupled to mass spectrometry to characterise the resin. As sandarac was the main component of the famous Italian varnish Vernice liquida, its characterisation is important for old paintings studies. However, although we could hope to differentiate sandarac, Juniperus communis and Juniperus oxycedrus resins by looking at their chemical composition, it appears that these resins are very similar. Besides, we notice a lack of old varnishes containing sandarac which complicates our work.


Assuntos
Cupressaceae/química , Pintura/análise , Resinas Vegetais/análise , Resinas Vegetais/química , Cromatografia Gasosa-Espectrometria de Massas , Juniperus/química , Terminologia como Assunto , Thuja/química
14.
DNA Repair (Amst) ; 60: 89-101, 2017 12.
Artigo em Inglês | MEDLINE | ID: mdl-29112893

RESUMO

Investigation of natural products is an attractive strategy to identify novel compounds for cancer prevention and treatment. Numerous studies have shown the efficacy and safety of natural products, and they have been widely used as alternative treatments for a wide range of illnesses, including cancers. However, it remains unknown whether natural products affect homologous recombination (HR)-mediated DNA repair and whether these compounds can be used as sensitizers with minimal toxicity to improve patients' responses to radiation therapy, a mainstay of treatment for many human cancers. In this study, in order to systematically identify natural products with an inhibitory effect on HR repair, we developed a high-throughput image-based HR repair screening assay and screened a chemical library containing natural products. Among the most interesting of the candidate compounds identified from the screen was ß-thujaplicin, a bioactive compound isolated from the heart wood of plants in the Cupressaceae family, can significantly inhibit HR repair. We further demonstrated that ß-thujaplicin inhibits HR repair by reducing the recruitment of a key HR repair protein, Rad51, to DNA double-strand breaks. More importantly, our results showed that ß-thujaplicin can radiosensitize cancer cells. Additionally, ß-thujaplicin sensitizes cancer cells to PARP inhibitor in different cancer cell lines. Collectively, our findings for the first time identify natural compound ß-thujaplicin, which has a good biosafety profile, as a novel HR repair inhibitor with great potential to be translated into clinical applications as a sensitizer to DNA-damage-inducing treatment such as radiation and PARP inhibitor. In addition, our study provides proof of the principle that our robust high-throughput functional HR repair assay can be used for a large-scale screening system to identify novel natural products that regulate DNA repair and cellular responses to DNA damage-inducing treatments such as radiation therapy.


Assuntos
Monoterpenos/uso terapêutico , Neoplasias/tratamento farmacológico , Rad51 Recombinase/efeitos dos fármacos , Radiossensibilizantes/uso terapêutico , Reparo de DNA por Recombinação/efeitos dos fármacos , Tropolona/análogos & derivados , Antineoplásicos/farmacologia , Antineoplásicos/uso terapêutico , Linhagem Celular Tumoral , Cupressaceae/química , DNA/metabolismo , Quebras de DNA de Cadeia Dupla , Quimioterapia Combinada , Feminino , Ensaios de Triagem em Larga Escala , Humanos , Monoterpenos/farmacologia , Monoterpenos/toxicidade , Neoplasias/enzimologia , Neoplasias/genética , Extratos Vegetais , Inibidores de Poli(ADP-Ribose) Polimerases/uso terapêutico , Rad51 Recombinase/metabolismo , Radiossensibilizantes/farmacologia , Radiossensibilizantes/toxicidade , Tropolona/farmacologia , Tropolona/uso terapêutico , Tropolona/toxicidade
15.
Molecules ; 22(6)2017 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-28574456

RESUMO

The main objective of this study was to determine the chemical composition of essential oils (EOs) obtained from leaf, old branches, and young branches of a coniferous species Calocedrus decurrens acclimated to Corsica. The analytical investigation was conducted by GC(RI), GC-MS, pc-GC, and NMR. C. decurrens leaf, old branches, and young branches EOs contained α-pinene (11.2; 56.6; 22.3%), myrcene (13.4; 8.4; 9.7%), Δ-3-carene (31.3; 5.2; 11.1%), limonene (6.4; 5.1; 5.5%), terpinolene (6.9; 1.5; 3.2%), and pin-2-en-8-ol (4.2; 4.5; 10.4%) as major components, respectively. Special attention was paid to purifying and identifying four unusual pinane derivatives: pin-2-en-8-ol, pin-2-en-8-yl Acetate, pin-2-en-8-al, and methyl pin-2-en-8-oate. The last two are reported for the first time.


Assuntos
Cupressaceae/química , Óleos Voláteis/química , Óleos Vegetais/química , Terpenos/química , Monoterpenos Bicíclicos , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Cromatografia Gasosa-Espectrometria de Massas , Folhas de Planta/química
16.
Anal Bioanal Chem ; 409(15): 3719-3729, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28401286

RESUMO

General emissions of volatile organic compounds from wood are well investigated, but only limited information is available on the odor-active substances contained therein. To close this gap, we aimed at specifically elucidating the odorous constituents of wood from incense cedar [Calocedrus decurrens (Torr.) Florin]; this material is commonly used for the production of a range of products such as pencils and interior accessories. Targeted odorant analysis requires specialized techniques combining modern odorant analytical tools with human-sensory evaluation. Following this concept, the odor profile of the wood sample was first evaluated by human-sensory analyses. Then, the most potent wood odorants were characterized by means of gas chromatography-olfactometry and ranked according to their odor potency via aroma extract dilution analysis. With use of this approach, more than 60 odorous substances were detected, and the 22 most potent odorants were successfully identified by gas chromatography-mass spectrometry/olfactometry and two-dimensional gas chromatography-mass spectrometry/olfactometry. Among the main odorants found were a series of terpenes, several degradation products of fatty acids, and a number of odorants with a phenolic core moiety. Five odorants are reported here for the first time as wood odorants, such as γ-octalactone and 3-phenylpropanoic acid; thymoquinone was demonstrated for the first time to have a pencil-like odor quality.


Assuntos
Cupressaceae/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Olfatometria/métodos , Madeira/química , Adulto , Benzoquinonas/análise , Feminino , Humanos , Masculino , Pessoa de Meia-Idade , Compostos Orgânicos Voláteis/análise , Adulto Jovem
17.
Food Funct ; 8(1): 86-95, 2017 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-28059416

RESUMO

The flavonoids (POFs) from the leaves of Platycladus orientalis (L.) Franco were purified using six different macroporous adsorption resins including polar resins NKA-9 and ADS-F8, semi-polar resins ADS-17 and AB-8, and non-polar resins D101 and ADS-5. Among semi-polar resins, AB-8 demonstrated the best adsorption and desorption capacities with an adsorption ratio of 86% and a desorption ratio of 52%. According to the Simultaneous Thermogravimetry-Differential Scanning Calorimetry (STA/TG-DSC) analysis, POFs showed three thermally decomposed temperatures (347.6 °C, 437.5 °C and 494.8 °C). The main flavonoids in POFs were identified as esculin, amentoflavone, glabridin, and afromosin. Meanwhile, POFs in the dosage range of 25 to 400 µg mL-1 showed a significant anti-inflammatory effect on lipopolysaccharide (LPS)-induced RAW 264.7 mouse macrophage cells, which could inhibit the secretion of NO, IL-6, and TNF-α through the inhibition of inflammatory-related gene expressions.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cupressaceae/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Adsorção , Animais , Anti-Inflamatórios/química , Varredura Diferencial de Calorimetria , Flavonoides/química , Interleucina-6/imunologia , Macrófagos/imunologia , Camundongos , Óxido Nítrico/imunologia , Extratos Vegetais/química , Porosidade , Células RAW 264.7 , Resinas Sintéticas/química
18.
Planta Med ; 83(6): 574-581, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-27776375

RESUMO

Podophyllotoxin, a lignan still extracted from the rhizomes of Podophyllum hexandrum (Berberidaceae), is the starting molecule for the semisynthesis of widely used anticancer drugs such as etoposide. However, this source is threatened by the over-collection of P. hexandrum. Plants belonging to the Linaceae and Cupressaceae families could be attractive alternative sources with species that contain the lignan podophyllotoxin or its precursors and derivatives. Wild flax species, such as Linum flavum, as well as some Juniperus and Callitris species were investigated for their lignan content, and the in vitro antiproliferative capacity of their extracts was assayed on four tumor cell lines. Some of the lignans were detected by LC-HRMS for the first time in these extracts.In addition, lignans purified from these plants and compounds semisynthesized from commercially available podophyllotoxin were tested in terms of their in vitro antiproliferative activity. The genus Juniperus was the most promising given its in vitro antiproliferative effects, which were also observed with extracts from L. flavum and Callitris species.The in vitro antiproliferative effect of the plant extracts studied here appears to correlate well with the contents of the aryltetralin lignan podophyllotoxin and its glycoside as well as with deoxypodophyllotoxin and 6-methoxypodophyllotoxin. The strongest correlation between the lignan content of the extracts and the antiproliferative activity was observed for 6-methoxypodophyllotoxin. Regarding the possibility of producing large renewable amounts of 6-methoxypodophyllotoxin, this molecule could be of interest to produce new anticancer drugs and to bypass the resistance mechanisms against podophyllotoxin-derived drugs.


Assuntos
Antineoplásicos/farmacologia , Cupressaceae/química , Linho/química , Juniperus/química , Lignanas/farmacologia , Extratos Vegetais/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Vias Biossintéticas , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sinergismo Farmacológico , Humanos , Lignanas/química , Lignanas/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Podofilotoxina/análogos & derivados , Podofilotoxina/química , Podofilotoxina/isolamento & purificação , Podofilotoxina/farmacologia
19.
Chem Biodivers ; 14(2)2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-27583773

RESUMO

The impact of phenological stages (vegetative, flowering and fruiting stages) on chemical composition, antioxidant, and antimicrobial activities of Tetraclinis articulata (Vahl) Mast. parts essential oils were investigated for the first time. GC and GC/MS analyses pointed to a quantitative variability of components; terpene hydrocarbons derivatives, represented by α-pinene (16.38 ± 0.19 - 31.78 ± 0.35%) and limonene (3.41 ± 0.07 - 9.49 ± 0.14%) as major components, predominate at the vegetative stage, whereas oxygenated derivatives, represented by camphor (16.11 ± 0.23 - 26.17 ± 0.29%) and bornyl acetate (15.21 ± 0.21 - 27.33 ± 0.33%) as major components, predominate at the fruiting stage. Furthermore, our findings showed that the plant parts collected at the fruiting stage possess the highest antioxidant activity and the best antimicrobial activity against the tested microorganisms, than plant parts collected at the vegetative and flowering stages. This highlighted variability reflects the high impact of phenological cycle on chemical composition and biological activities, which led to conclude that we should select essential oils to be investigated carefully depending on phenological stage, in order to have the highest effectiveness of essential oil in terms of biological activities for human health purposes.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Cupressaceae/química , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Anti-Infecciosos/química , Antioxidantes/química , Bactérias/efeitos dos fármacos , Compostos de Bifenilo/química , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Óleos Voláteis/química , Picratos/química
20.
Environ Toxicol Pharmacol ; 46: 270-276, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27522546

RESUMO

Although numerous hypotheses have been proposed to prevent chemotherapy-induced alopecia (CIA), effective pharmaceuticals have yet to be developed. In our study, the back hairs of C57BL/6 mice were factitiously removed. These mice were then treated with cedrol or minoxidil daily. Mice with early-stage anagen VI hair follicles were treated with cyclophosphamide (CYP, 125mg/kg) to induce alopecia. The CYP-damaged hair follicles were observed and quantified by using a digital photomicrograph. The results demonstrated that the minoxidil-treated mice suffered from complete alopecia similar to the model 6days after CYP administration. Simultaneously, the cedrol-treated (200mg/kg) mice manifested mild alopecia with 40% suppression. Histological observation revealed that anagen hair follicles of the cedrol-pretreated mice (82.5%) likely provided from damage compared with the sparse and dystrophic hair follicles of the model mice (37.0%). Therefore, the use of topical cedrol can prevent hair follicle dystrophy and provide local protection against CIA.


Assuntos
Alopecia/prevenção & controle , Antineoplásicos Alquilantes/toxicidade , Ciclofosfamida/toxicidade , Terpenos/uso terapêutico , Alopecia/induzido quimicamente , Animais , Cupressaceae/química , Dermatite de Contato/etiologia , Dermatite de Contato/imunologia , Modelos Animais de Doenças , Feminino , Folículo Piloso/efeitos dos fármacos , Folículo Piloso/crescimento & desenvolvimento , Folículo Piloso/patologia , Camundongos Endogâmicos C57BL , Folhas de Planta/química , Sesquiterpenos Policíclicos , Pele/efeitos dos fármacos , Pele/imunologia , Terpenos/administração & dosagem , Terpenos/isolamento & purificação , Terpenos/toxicidade , Testes de Toxicidade Aguda
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