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1.
Acta Crystallogr C Struct Chem ; 76(Pt 9): 914-920, 2020 09 01.
Artigo em Inglês | MEDLINE | ID: mdl-32887863

RESUMO

The terpenoid (-)-Istanbulin A is a natural product isolated from Senecio filaginoides DC, one of the 270 species of Senecio (Asteraceae) which occurs in Argentina. The structure and absolute configuration of this compound [9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4H,5H-naphtho[2,3-b]-furan-2,8-dione or (4S,5R,8R,10S)-1-oxo-8ß-hydroxy-10ßH-eremophil-7(11)-en-12,8ß-olide, C15H20O4] were determined by single-crystal X-ray diffraction studies. It proved to be a sesquiterpene lactone showing an eremophilanolide skeleton whose chirality is described as 4S,5R,8R,10S. Structural results were also in agreement with the one- and two-dimensional (1D and 2D) NMR and HR-ESI-MS data, and other complementary spectroscopic information. In addition, (-)-Istanbulin A is a polymorph of the previously reported form of (-)-Istanbulin A, form I; thus, the title compound is denoted form II or polymorph II. Structural data and a literature search allowed the chirality of Istanbulin A to be revisited. The antimicrobial and antifungal activities of (-)-Istanbulin A, form II, were evaluated in order to establish a reference for future comparisons and applications related to specific crystal forms of Istanbulins.


Assuntos
Antifúngicos/química , Furanos/química , Sesquiterpenos/química , Cristalografia por Raios X , Ligação de Hidrogênio , Espectroscopia de Ressonância Magnética , Estereoisomerismo
2.
J Nat Med ; 74(4): 750-757, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32621255

RESUMO

Artemisia sieversiana is an annual herbaceous plant distributed throughout Central and East Eurasia and is regarded as an undesirable forage plant in Mongolia. It affects livestock, so information about its chemical composition is needed. We isolated three new sesquiterpenoids (1-3) and known compounds from A. sieversiana and investigated their activities. The absolute configuration of 1 was established using single-crystal X-ray diffraction crystallography, and its configuration differed from those of reported compounds with similar structures. Two additional new sesquiterpenoids (2 and 3) with similar structures were identified, and their configurations were determined. The trypanocidal activities of the isolated compounds (1-18) against Trypanosoma congolense and the pathogen responsible for fatal trypanosomosis in animals were estimated. Flavonoids and lignans were identified as active compounds with IC50 values ranging from 2.9 to 90.2 µM.


Assuntos
Artemisia/química , Flavonoides/química , Lignanas/química , Plantas/química , Sesquiterpenos/química , Estrutura Molecular , Mongólia
3.
J Nat Med ; 74(4): 811-818, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32705519

RESUMO

Investigation of the dried whole plants of Artemisia annua led to the isolation of two new sesquiterpenes, artemanins A (1) and B (2), along with twenty-nine known compounds. The structures of the new compounds were elucidated by spectroscopic and chemical means.


Assuntos
Artemisia annua/química , Espectroscopia de Ressonância Magnética/métodos , Plantas/química , Sesquiterpenos/química , Estrutura Molecular
4.
J Chromatogr A ; 1624: 461155, 2020 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-32540056

RESUMO

The topic in the present paper is to prepare molecularly imprinted polymer (MIP) using the template molecule with low purity. For the first time, a surrounding of macromolecular crowding was established to promote the formation of the complex of the template with functional monomer efficiently thus highly pure template molecule was unnecessary. In this study, the MIP monolith was synthesized using low purity lactucopicrin as template in place of highly pure one, and polystyrene was used as macromolecular crowding agent. 4-Vinylpyridine and ethyleneglycol dimethacrylate were used as functional monomer and crosslinker, respectively. Polymerization parameters, including the ratio of functional monomer/template, various template concentrations, and PS concentration on the affinity of the resulting MIP were systematically investigated. For the lactucopicrin MIP made with the purity of lactucopicrin of 92%, the imprinting factor can be up to 2.2. The resulting MIP was filled in solid phase extraction (SPE) cartridge to purify lactucopicrin from the crude extract of Cichorium glandulosum Boiss. et Huet. After two cycles of MIP SPE for the crude extract, the highest recovery and purity of lactucopicrin was 64.8% and 97.8%, respectively. The results indicated that the use of macromolecular crowding agent is an effective method for improving the performance of the MIP prepared with the template of low purity, particularly valuable to the cases in which the highly pure target molecule is hard to be obtained.


Assuntos
Impressão Molecular , Polímeros/química , Asteraceae/química , Reagentes para Ligações Cruzadas/química , Lactonas/química , Lactonas/isolamento & purificação , Metacrilatos/química , Polimerização , Poliestirenos/química , Piridinas/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Extração em Fase Sólida
5.
J Nat Med ; 74(4): 689-701, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32535872

RESUMO

From the methanolic extract of the aerial parts of Petasites japonicus, six new eremophilane-type sesquiterpenoids, petasitesterpenes I-VI were isolated together with eight known compounds including S-japonin and eremophilenolide. The chemical structures of the isolated new compounds were elucidated based on chemical/physicochemical evidence. For petasitesterpenes I and II, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Among the isolated compounds, petasitesterpenes I, II, VI, and S-japonin showed cytotoxic activity against both human astrocytoma U-251MG cancer cells (non-CSCs) and their cancer stem cells (CSCs) isolated by sphere formation. In addition, cytotoxic activities of these compounds against breast cancer MDA-MB-231 were evaluated, supporting that petasitesterpene II has more effective than other isolated compounds.


Assuntos
Células-Tronco Neoplásicas/química , Petasites/química , Plantas Medicinais/química , Sesquiterpenos/química , Humanos , Estrutura Molecular
6.
Int J Nanomedicine ; 15: 3087-3098, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32431503

RESUMO

Purpose: Aldo-ketoreductase (AKR) 1C3 is crucial for testosterone synthesis. Abnormally high expression/activity of AKR1C3 can promote castration-resistant prostate cancer (CRPC). A mansonone derivative and AKR1C3 inhibitor, 6e, was combined with 4D5 (extracellular fragment of the monoclonal antibody of human epidermal growth factor receptor-2)-modified chitosan to achieve a nanodrug-delivery system (CS-4D5/6e) to treat CRPC. Materials and Methods: Morphologies/properties of CS-4D5/6e were characterized by atomic force microscopy, zeta-potential analysis, and Fourier transform-infrared spectroscopy. CS-4D5/6e uptake was measured by immunofluorescence under confocal laser scanning microscopy. Testosterone in LNCaP cells overexpressing human AKR1C3 (LNCaP-AKR1C3) and cell lysates was measured to reflect AKR1C3 activity. Androgen receptor (AR) and prostate-specific antigen (PSA) expression was measured by Western blotting. CS-4D5/6e-based inhibition of AKR1C3 was evaluated in tumor-xenografted mice. Results: CS-4D5/6e was oblate, with a particle size of 200-300 nm and thickness of 1-5 nm. Zeta potential was 1.39±0.248 mV. 6e content in CS-4D5/6e was 7.3±1.4% and was 18±3.6% for 4D5. 6e and CS-4D5/6e inhibited testosterone production significantly in a concentration-dependent manner in LNCaP-AKR1C3 cells, and a decrease in expression of AKR1C3, PSA, and AR was noted. Half-maximal inhibitory concentration of CS-4D5/6e on LNCaP-AKR1C3 cells was significantly lower than that in LNCaP cells (P<0.05). CS-4D5/6e significantly reduced growth of 22Rv1 tumor xenografts by 57.00% compared with that in the vehicle group (P<0.01). Conclusion: We demonstrated the antineoplastic activity of a potent AKR1C3 inhibitor (6e) and its nanodrug-delivery system (CS-4D5/6e). First, CS-4D5/6e targeted HER2-positive CRPC cells. Second, it transferred 6e (an AKR1C3 inhibitor) to achieve a reduction in intratumoral testosterone production. Compared with 6e, CS-4D5/6e showed lower systemic toxicity. CS-4D5/6e inhibited tumor growth effectively in mice implanted with tumor xenografts by downregulating testosterone production mediated by intratumoral AKR1C3. These results showed a promising strategy for treatment of the CRPC that develops invariably in prostate-cancer patients.


Assuntos
Membro C3 da Família 1 de alfa-Ceto Redutase/antagonistas & inibidores , Antineoplásicos/química , Antineoplásicos/farmacologia , Terapia de Alvo Molecular/métodos , Neoplasias de Próstata Resistentes à Castração/tratamento farmacológico , Animais , Anticorpos Monoclonais/química , Antineoplásicos/administração & dosagem , Linhagem Celular Tumoral , Quitosana/química , Sistemas de Liberação de Medicamentos/métodos , Humanos , Masculino , Camundongos Endogâmicos BALB C , Nanoestruturas/administração & dosagem , Nanoestruturas/química , Naftoquinonas/química , Antígeno Prostático Específico/metabolismo , Neoplasias de Próstata Resistentes à Castração/metabolismo , Neoplasias de Próstata Resistentes à Castração/patologia , Receptor ErbB-2/imunologia , Receptores Androgênicos/metabolismo , Sesquiterpenos/química , Testosterona/metabolismo , Ensaios Antitumorais Modelo de Xenoenxerto
7.
PLoS One ; 15(4): e0229925, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32251434

RESUMO

Basidiomycete fungi are a rich source of natural products with a diverse array of potentially exploitable bioactivities. Two dimeric sesquiterpenes, bovistol B (1) and D (2), and one monomeric sesquiterpene, strossmayerin (7), were isolated from the culture filtrate of the basidiomycete fungus Coprinopsis strossmayeri. The structures were determined through a combination of MS and 1D/2D NMR spectroscopic techniques. Likely monomeric precursors, identified on the basis of HRMS analysis, allow a plausible biosynthetic pathway to be proposed for the biosynthesis of 1 and 2, involving the dimerisation of the monomer through a hetero-Diels-Alder mechanism. A gene cluster, including a putative sesquiterpene 1-11 cyclase, was identified through phylogenetic and RNA-seq analysis, and is proposed to be responsible for the biosynthesis of 1 and 2.


Assuntos
Agaricales/química , Basidiomycota/química , Redes e Vias Metabólicas , Sesquiterpenos/química , Agaricales/ultraestrutura , Basidiomycota/ultraestrutura , Produtos Biológicos/química , Filtração , Espectroscopia de Ressonância Magnética , Estrutura Molecular
8.
Zhongguo Zhong Yao Za Zhi ; 45(1): 37-51, 2020 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-32237409

RESUMO

The genus Carpesium plants contain many kinds of sesquiterpenes. Up to now, more than 201 sesquiterpene compounds have been isolated and identified, including 86 germacranolides, 30 eudesmanolides, 29 guaianolides, 23 sesquiterpene dimers, 9 pseudoguaianes, 9 carabranolides, 7 xanthanolides, 6 sesquiterpenes without lactone, 1 eremophilane and 1 tricyclo dodecane sesquiterpene. The reported sesquiterpenes possess a series of pharmacological properties, such as anti-tumor, anti-inflammatory, antibacterial, antiparasitic, insecticidal, and antiviral activities. This paper summarizes the 201 chemical structures and biological activities of sesquiterpenes in genus Carpesium, and provides the scientific basis for the further development and utilization.


Assuntos
Asteraceae/química , Sesquiterpenos/farmacologia , Antibacterianos , Anti-Inflamatórios , Lactonas , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Sesquiterpenos/química
9.
Biomed Res Int ; 2020: 6892961, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32149121

RESUMO

Inflammatory mediators and inflammatory cells in the inflammatory microenvironment promote the transformation of normal cells to cancer cells in the early stage of cancer, promote the growth and development of cancer cells, and induce tumor immune escape. The monomeric active ingredient ß-elemene is extracted from the traditional Chinese medicine Curcuma wenyujin and has been proven to have good anti-inflammatory and antitumor activities in clinical applications for more than 20 years in China. Recent studies have found that this traditional Chinese medicine plays a vital role in macrophage infiltration and M2 polarization, as well as in regulating immune disorders, and it even regulates the transcription factors NF-κB and STAT3 to alter inflammation, tumorigenesis, and development. In addition, ß-elemene regulates not only different inflammatory factors (such as TNF-α, IFN, TGF-ß, and IL-6/10) but also oxidative stress in vivo and in vitro. The excellent anti-inflammatory and antitumor effects of ß-elemene and its ability to alter the inflammatory microenvironment of tumors have been gradually elaborated. Although the study of monomeric active ingredients in traditional Chinese medicines is insufficient in terms of quality and quantity, the pharmacological effects of more active ingredients of traditional Chinese medicines will be revealed after ß-elemene.


Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Sesquiterpenos/farmacologia , Microambiente Tumoral/efeitos dos fármacos , Animais , Carcinogênese/efeitos dos fármacos , Linhagem Celular Tumoral , China , Curcuma/química , Humanos , Doenças do Sistema Imunitário/tratamento farmacológico , Macrófagos/efeitos dos fármacos , Medicina Tradicional Chinesa , NF-kappa B , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase/metabolismo , Estresse Oxidativo , Fator de Transcrição STAT3/efeitos dos fármacos , Sesquiterpenos/química , Fatores de Transcrição/efeitos dos fármacos
10.
Org Biomol Chem ; 18(12): 2252-2263, 2020 03 25.
Artigo em Inglês | MEDLINE | ID: mdl-32149317

RESUMO

Glycoconjugates, due to their diverse functions, are widely regarded as biologically important molecules. Artemisinic acid 1 occurs naturally in the plant Artemisia annua and is considered to be the biogenetic precursor of the antimalarial drug, artemisinin 2. We report herein the design and synthesis of diverse artemisinic acid derived glycoconjugates. We have synthesized 12-O-artemisinic acid-glycoconjugates (7a-k) and 12-N-artemisinic acid-glycoconjugates (8a-k) by utilizing Cu(i)-catalyzed azide-alkyne cycloaddition reactions (Click chemistry) with various synthesized sugar azides (6a-k) in good to excellent yields along with two fluorescently labeled compounds, 12-O-artemisinic acid-glycoconjugate 11 and 12-N-artemisinic acid-glycoconjugate 12, to investigate the mode of action of these compounds in biological systems. All the synthesized artemisinic acid glycoconjugates were assayed for their efficacy against the MCF7 cell line. Our anticancer studies indicated that all the synthesized compounds inhibited the growth of MCF7 cells in a dose dependent manner, barring compounds 4 and 7d. However, these compounds exhibit moderate cytotoxicity, as is evident from their IC50 values.


Assuntos
Antineoplásicos/síntese química , Artemisininas/química , Glicoconjugados/síntese química , Antineoplásicos/química , Antineoplásicos/farmacologia , Azidas/química , Química Click , Reação de Cicloadição , Desenho de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Glicoconjugados/farmacologia , Humanos , Concentração Inibidora 50 , Células MCF-7 , Sesquiterpenos/química
11.
Chem Commun (Camb) ; 56(10): 1517-1520, 2020 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-31919484

RESUMO

The pseudoguaianelactones A (1) and B (2), two novel sesquiterpene lactones with an unprecedented [5,7,7] ring system featuring an α-methylene-γ-lactone moiety, together with a new pseudoguaianelactone C (3) were isolated from the roots of Lindera glauca. Pseudoguaianelactones A-C (1-3) inhibited nitric oxide (NO) production, with IC50 values ranging from 1.38 to 4.00 µM. Moreover, all compounds significantly suppressed the production of pro-inflammatory mediators (TNF-α, IL-6, IL-1ß and PGE2) and the protein expression of the enzymes iNOS and COX-2.


Assuntos
Anti-Inflamatórios/química , Ciclo-Oxigenase 2/metabolismo , Lindera/química , Óxido Nítrico Sintase Tipo II/metabolismo , Sesquiterpenos/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cristalografia por Raios X , Citocinas/metabolismo , Lindera/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
12.
Artigo em Inglês | MEDLINE | ID: mdl-31911205

RESUMO

Due to the biological features of sesquiterpene coumarins and incomparable interest in therapeutics application of natural products, extraction of sesquiterpene coumarins from asafoetida have gained highly attention. One of the most important problems is removal of sulfur containing compounds which are co-existed with sesquiterpene coumarins. So employment of new methods for selective extraction and cleanup of sesquiterpene coumarins is very substantial. In this study using dummy molecularly imprinting technique, 7-hydroxycoumarin-imprited polymer was synthesized and after evaluation of binding properties of polymers, the optimum one was used as sorbent in solid phase extraction. Afterwards dummy molecularly imprinting solid phase extraction (DMISPE) method was calibrated for simultaneous extraction of galbanic acid, 7-isopentenyloxy coumarin and auraptene from aqueous media before high performance liquid chromatography with UV detector (HPLC-UV) analysis. The recovery was in the range of 68.32%-84.69%, which were in the acceptable range compared to previous works. Finally, the calibrated DMISPE method was used for extraction and cleanup of sesquiterpene coumarins from asafetida plant. The concentration of isosamarcandin, kellerin and farnesiferol in asafoetida extract was obtained 0.8, 2.7, and 5 µg/mL, respectively, using standard addition method.


Assuntos
Cumarínicos/isolamento & purificação , Ferula/química , Impressão Molecular/métodos , Sesquiterpenos/isolamento & purificação , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão , Cumarínicos/análise , Cumarínicos/química , Extratos Vegetais/química , Reprodutibilidade dos Testes , Sesquiterpenos/análise , Sesquiterpenos/química
13.
Artigo em Inglês | MEDLINE | ID: mdl-31931331

RESUMO

Ptaquiloside (PTA) is an illudane glycoside partly responsible for the carcinogenicity of bracken ferns (Pteridium sp.). The PTA analogues ptesculentoside (PTE) and caudatoside (CAU) have similar biochemical reactivity. However, both compounds are highly under-investigated due to the lack of analytical standards and appropriate methods. This study presents a robust method for preparation of analytical standards of PTE, CAU, PTA, the corresponding hydrolysis products: pterosins G, A and B, and an LC-MS based method for simultaneous quantification of the six compounds in bracken. The chromatographic separation of analytes takes 5 min. The observed linear range of quantification was 20-500 µg/L for PTA and pterosin B, and 10-250 µg/L for the remaining compounds (r > 0.999). The limits of detection were 0.08-0.26 µg/L for PTE, CAU and PTA and 0.01-0.03 µg/L for the pterosins, equivalent to 2.0-6.5 µg/g and 0.25-0.75 µg/g in dry weight, respectively. The method was applied on 18 samples of dried fern leaves from 6 continents. Results demonstrated high variation in concentrations of PTE, CAU and PTA with levels prior to hydrolysis up to 3,900, 2,200 and 2,100 µg/g respectively. This is the first analytical method for simultaneous and direct measurement of all six compounds. Its application demonstrated that bracken ferns contain significant amounts of PTE and CAU relative to PTA.


Assuntos
Cromatografia Líquida/métodos , Glicosídeos , Indanos , Pteridium/química , Sesquiterpenos , Glicosídeos/análise , Glicosídeos/química , Indanos/análise , Indanos/química , Limite de Detecção , Modelos Lineares , Espectrometria de Massas/métodos , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/química , Extratos Vegetais/química , Sesquiterpenos Policíclicos/análise , Sesquiterpenos Policíclicos/química , Reprodutibilidade dos Testes , Sesquiterpenos/análise , Sesquiterpenos/química
14.
Org Biomol Chem ; 18(4): 642-645, 2020 01 28.
Artigo em Inglês | MEDLINE | ID: mdl-31916553

RESUMO

Photeroids A (1) and B (2), two structurally fascinating meroterpenoids, were isolated from the deep-sea-derived fungus Phomopsis tersa FS441. Their structures were sufficiently established by a comprehensive interpretation of the spectroscopic data, NMR spectra, and ECD calculation. Photeroids A and B represented the first phenolic sesquiterpene meroterpenoids featuring a highly fused 6/6/6/6 tetracyclic ring system derived through a rarely-occurring hetero-Diels-Alder reaction via an orthoquinone methide intermediate. Additionally, they were also evaluated for their cytotoxic activities against four human cancer cells, wherein compounds 1 and 2 exhibited moderate cytotoxic activities.


Assuntos
Ascomicetos/química , Fenóis/farmacologia , Sesquiterpenos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Humanos , Fenóis/química , Fenóis/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
15.
Chin J Nat Med ; 18(1): 75-80, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31955826

RESUMO

Purpurolides D-F (1-3), three new polyoxygenated bergamotanes bearing a 6/4/5/5 tetracyclic ring system, were isolated from the endophytic fungus Penicillium purpurogenum IMM 003. Their structures were unambiguously elucidated based on extensive spectroscopic data analyses, 13C NMR chemical shifts calculations coupled with the DP4+ probability method, and the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1-3 showed significant inhibitory activity against pancreatic lipase (PL). The result highlights that the presence of 3-hydroxylated decanoic acid moiety at C-14 is important for increasing the inhibition potency against PL.


Assuntos
Lipase/antagonistas & inibidores , Penicillium/química , Penicillium/isolamento & purificação , Sesquiterpenos/química , Linhagem Celular Tumoral , Humanos , Estrutura Molecular
16.
Int J Mol Sci ; 21(2)2020 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-31963614

RESUMO

Doxorubicin represents a valuable choice for different cancers, although the severe side effects occurring at the high effective dose limits its clinical use. In the present study, potential strategies to potentiate low-dose doxorubicin efficacy, including a metronomic schedule, characterized by a short and repeated exposure to the anticancer drug, and the combination with the natural chemosensitizing sesquiterpenes ß-caryophyllene and ß-caryophyllene oxide, were assessed in human hepatoma HepG2 cells. The involvement of P-glycoprotein (P-gp) in the HepG2-chemosensitization to doxorubicin was evaluated. Also, the direct interaction of caryophyllene sesquiterpenes with P-gp was characterized by molecular docking and dynamic simulation studies. A metronomic schedule allowed us to enhance the low-dose doxorubicin cytotoxicity and the combination with caryophyllane sesquiterpenes further potentiated this effect. Also, an increased intracellular accumulation of doxorubicin and rhodamine 123 induced by caryophyllane sesquiterpenes was found, thus suggesting their interference with P-gp function. A lowered expression of P-gp induced by the combinations, with respect to doxorubicin alone, was observed too. Docking studies found that the binding site of caryophyllane sesquiterpene was next to the ATP binding domain of P-gp and that ß-caryophyllene possessed the stronger binding affinity and higher inhibition potential calculated by MM-PBSA. Present findings strengthen our hypothesis about the potential chemosensitizing power of caryophyllane sesquiterpenes and suggest that combining a chemosensitizer and a metronomic schedule can represent a suitable strategy to overcome drawbacks of doxorubicin chemotherapy while exploiting its powerful activity.


Assuntos
Membro 1 da Subfamília B de Cassetes de Ligação de ATP/metabolismo , Apoptose , Carcinoma Hepatocelular/patologia , Doxorrubicina/farmacologia , Neoplasias Hepáticas/patologia , Sesquiterpenos Policíclicos/química , Sesquiterpenos/química , Membro 1 da Subfamília B de Cassetes de Ligação de ATP/genética , Antibióticos Antineoplásicos/farmacologia , Carcinoma Hepatocelular/tratamento farmacológico , Carcinoma Hepatocelular/metabolismo , Simulação por Computador , Relação Dose-Resposta a Droga , Humanos , Técnicas In Vitro , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/metabolismo , Células Tumorais Cultivadas
17.
J Chem Ecol ; 46(1): 1-9, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31840210

RESUMO

The rice stalk stink bug, Tibraca limbativentris, is an important rice pest in Brazil with a high invasive potential for Mexico and the USA. The sex pheromone of this species was previously identified as a combination of two stereoisomers of 1,10-bisaboladien-3-ol (zingiberenol), but the absolute configurations of these sesquiterpenes were not determined, neither were their effect(s) on T. limbativentris behavior evaluated. In this study, using two chiral columns, we compared retention times of the two natural 1,10-bisaboladien-3-ol stereoisomers from air-entrainment samples of male T. limbativentris with those of synthetic stereoisomers of 1,10-bisaboladien-3-ol. The results showed that T. limbativentris males produce (3S,6S,7R)-1,10-bisaboladien-3-ol (1) and (3R,6S,7R)-1,10-bisaboladien-3-ol (5) as their sex pheromone. Two new minor, male-specific components were also identified as cis and trans isomers of 2,10-bisaboladien-1-ol (sesquipiperitol). Y-tube olfactometer bioassays showed that the major (3S,6S,7R) isomer 1 was essential for attraction of T. limbativentris females, but the minor (3R,6S,7R) isomer 2 was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1S,6S,7R) and (1R,6S,7R) stereoisomers of sesquipepiritol also attracted T. limbativentris females.


Assuntos
Comportamento Animal/efeitos dos fármacos , Heterópteros/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Atrativos Sexuais/química , Atrativos Sexuais/farmacologia , Animais , Cromatografia Gasosa , Feminino , Heterópteros/metabolismo , Masculino , Estereoisomerismo , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química
18.
Chem Biodivers ; 17(2): e1900544, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31840372

RESUMO

Geranium species are widely used in traditional medicine of Balkan. The aim of this work was to investigate and compare chemical composition of volatile fractions obtained by hydrodistillation from aerial parts of G. macrorrhizum, G. phaeum, G. sanguineum, G. robertianum, G. palustre, G. pyrenaicum, G. columbinum and G. lucidum as well as from underground parts of G. macrorrhizum and G. phaeum, originated from Vlasina plateau in South Eastern Serbia. The volatiles were analyzed using GC/MS and GC-FID. G. palustre volatiles have been studied for the first time with ß-selinene (18.6 %) as a characteristic compound. The cluster analysis revealed separation of volatiles into two main groups. Volatile fractions of G. macrorrhizum were separated from all other samples due to high sesquiterpene content (92.3 % in aerial and 94.6 % in underground parts). The volatile fractions of other samples were mainly composed of sesquiterpenes (10.8-61.8 %), diterpenes (12.9-43.0 %) and fatty acids and their derivatives (6.6-21.6 %) with the exception of volatile fraction of G. phaeum underground parts which was dominated only by fatty acids and their derivatives (76.6 %). The results presented in this article contribute to the knowledge on the chemistry of this genus and advances the knowledge on flora of southeast Serbia.


Assuntos
Geranium/química , Compostos Orgânicos Voláteis/química , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Geranium/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Sérvia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Compostos Orgânicos Voláteis/análise
19.
J Nat Med ; 74(1): 119-126, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31392565

RESUMO

Five eudesmane-type sesquiterpene glycosides, named sonneratiosides A-E (1-5), were isolated from the leaves of Sonneratia alba (Lythraceae). The aglycone of sonneratioside A was identified as cryptomeridiol also known as proximadiol. X-ray crystallographic analysis of sonneratioside A confirmed its structure and its absolute stereochemistry. Eudesmol ß-D-glucopyranoside (6) was also isolated from nature for the first time. The tyrosinase inhibitory activity was assayed for the new compounds together with seven known compounds. Among them, arbutin (12) showed the expected activity and luteolin 7-O-rutinoside (10) showed comparable activity to arbutin.


Assuntos
Lythraceae/química , Sesquiterpenos de Eudesmano/química , Arbutina/química , Glicosídeos/química , Estrutura Molecular , Monofenol Mono-Oxigenase/antagonistas & inibidores , Naftalenos/química , Folhas de Planta/química , Sesquiterpenos/química
20.
Biomed Chromatogr ; 34(1): e4717, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31634986

RESUMO

A sensitive ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method was established to analyze furanodienone in rat plasma. In the process of chromatographic separation, selected reaction monitoring transitions for furanodienone and patchouli alcohol (internal standard, IS) were m/z 231.1 → 83.2 and m/z 205.1 → 95.1, respectively. Great linearity of furanodienone in plasma samples was found in the corresponding concentration range (r > 0.995). Intra- and inter-day precisions (RSD, %) were <11.3% in plasma, and the accuracy (RE, %) was within ±10.7%. This method was used to the furanodienone study on rat pharmacokinetics after a single oral dose of 10 mg/kg of furanodiene. The results indicated that the maximum observed plasma concentration was 52.4 ± 19.1 ng/ml at 1.2 ± 0.7 h with an elimination half-life of 2.2 ± 0.7 h. The obtained data indicated that furanodienone could be moderately distributed and eliminated.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Furanos/sangue , Sesquiterpenos/sangue , Espectrometria de Massas em Tandem/métodos , Animais , Estabilidade de Medicamentos , Furanos/química , Furanos/farmacocinética , Modelos Lineares , Masculino , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Sesquiterpenos/química , Sesquiterpenos/farmacocinética
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