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1.
Phytochemistry ; 170: 112216, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31841782

RESUMO

Hyperelodiones A-C, three undescribed monoterpenoid polyprenylated acylphloroglucinols possessing 6/6/6 fused tricyclic core, were isolated from Hypericum elodeoides Choisy. Their gross structures were elucidated by HRESIMS and NMR data. The absolute configurations of hyperelodiones A-C were assigned by their calculated and compared electronic circular dichroism (ECD) spectra combined with their common biosynthetic origin. A fluorescence quenching assay suggested that hyperelodiones A-C could bind to RXRα-LBD, whereas hyperelodione C showed the strongest interaction with a KD of 12.81 µΜ. In addition, hyperelodiones A-C dose-dependently inhibited RXRα transactivation and the growth of HeLa and MCF-7 cells. Among them, hyperelodione C showed the most potent inhibitory activities and dose-dependent PARP cleavage. Molecular docking results suggested that hyperelodione C showed a different interaction mode compared with hyperelodione A and hyperelodione B. Thus, hyperelodione C can be considered as a promising lead compound for cancer therapy, which can bind to RXRα-LBD and induce HeLa and MCF-7 cell apoptosis.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Hypericum/química , Monoterpenos/farmacologia , Compostos Fitoquímicos/farmacologia , Receptor X Retinoide alfa/antagonistas & inibidores , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Células MCF-7 , Conformação Molecular , Simulação de Acoplamento Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Receptor X Retinoide alfa/metabolismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
2.
Chem Biodivers ; 17(2): e1900553, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31869516

RESUMO

The aroma emitted from the different organs of two Salvia verbenaca L. populations from Jordan were extracted by Solid Phase Micro-Extraction (SPME) and then analyzed by GC/MS. The emission profile of the stem, leaf and sepal samples from the Mediterranean zone (Al-Salt) was dominated by monoterpene hydrocarbons (68.0 %, 33.7 %, and 42.2 %, respectively). The emission profile of flowering parts including pre-flowering buds, fully expanded flowers and petals was dominated by oxygenated monoterpenes (58.6 %, 59.3 % and 87.1 %, respectively). The major constituent detected in these organs was trans-sabinene hydrate acetate (range 14.5 %-87.0 %). On the other hand, samples collected from Irano-Turanian zone showed different emission patterns. While the stems, leaves and petal emissions were dominated by sesquiterpene hydrocarbons (54.9 %, 76.8 % and 52.6 %, respectively), monoterpene hydrocarbons dominated the emission profiles of the pre-flowering buds (75.1 %) and fully expanded flowers (73.6 %). Petals emissions were characterized by high concentrations of oxygenated monoterpenes (58.8 %). Notably, trans-sabinene hydrate dominated most organs emissions except for leaves (range 20.0 %-58.8 %). Principle Component Analysis (PCA) and Cluster Analysis (CA) revealed two different clusters related to the two different geographical zones. The current investigation revealed two ecotypes of S. verbenaca that could result in two different chemotypes. Trans-sabinene hydrate acetate and trans-sabinene hydrate are suggested compounds for identifying these two chemotypes.


Assuntos
Salvia/química , Compostos Orgânicos Voláteis/química , /química , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Jordânia , Monoterpenos/química , Monoterpenos/isolamento & purificação , Folhas de Planta/química , Folhas de Planta/metabolismo , Análise de Componente Principal , Salvia/metabolismo , Microextração em Fase Sólida , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/isolamento & purificação
3.
Phytomedicine ; 60: 152977, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31474477

RESUMO

BACKGROUND: Intrigued by testimonies of Saxon borreliosis self-help groups concerning considerabl improvements of their symptoms by ingestion of Cistus creticus L. (Cistaceae) leaf preparations, we recently reported on the growth inhibiting activity of extracts with different polarities and its volatile oil against Borrelia burgdorferi sensu stricto (Bbss) in vitro, determined by a bioassay guided procedure. The most active volatile oil (only about 0.10% in leaves) was found to be dominated by labdane-type manoyloxides as well as carvacrol, determined via GC-MS. HYPOTHESIS: These terpenes are major active constituents of the old pharmaceutical oleoresin labdanum, which is secreted from the leaf surface of C. creticus and traditionally harvested, e.g., on Crete by brushing the shrubs. METHODS: In order to elucidate the definite anti-Borrelia active principles of C. creticus, preparative scale separation of the diethyl­ether soluble fraction of Cretan labdanum was achieved by combined silica gel 60-and RP-18 CC and analysed by novel TLC-Extractor/ES-MS as well as by 1d/2d-1H/13C-NMR data. For the antispirochaetal activity tests against Bbss in vitro, all samples were solubilised in water with addition of polysorbate 80, the effect of which on bacterial growth was examined and found to be negligible. RESULTS: This led to isolation and identification of the monoterpene carvacrol as well as of the four major manoyloxides manoyloxide (A), 3-acetoxy-manoyloxide (B), 3­hydroxy-manoyloxide (C), and epi­manoyloxide (D). Additionally, 2-keto-manoyloxide (E) and sclareol (F) were identified via GC/EI-MS. In subsequent microbiological tests of the isolated compounds, epi­manoyloxide (D) exhibited by far the strongest individual antispirochaetal effect, equal to the positive control amoxicilline. Furthermore, manoyloxide (A), carvacrol, and the diethyl­ether soluble fraction of labdanum as a whole contribute to the strong antispirochaetal activity, while the other labdanes were less active. Isolated manoyloxides were further used as external standards for a GC-MS screening of labdanum samples from different origins, revealing exceptionally high contents of all analysed manoyloxides in the samples of Cretan labdanum from C. creticus, while their contents in other commercial available labdanum samples were lower by several orders of magnitude. Especially in Spanish labdanum samples, declared as Cistus ladanifer L., mainly simple alkanes and at most traces of epi­manoyloxide (D) and of manoyloxide (A) could be detected. CONCLUSION: The application of C. creticus preparations by Lyme disease self-help groups may be considered as a reasonable therapy approach. For the first time, isolated epi­manoyloxide and carvacrol could be evaluated as most promising candidates for drug development and labdanum based phytomedicine development, respectively. They should serve as vital active markers for quality assessments of C. creticus preparations.


Assuntos
Antibacterianos/farmacologia , Borrelia/efeitos dos fármacos , Cistus/química , Diterpenos/farmacologia , Antibacterianos/isolamento & purificação , Diterpenos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Grécia , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Terpenos/isolamento & purificação , Terpenos/farmacologia
4.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470602

RESUMO

The promising antimicrobial activity of essential oils (EOs) has led researchers to use them in combination with antimicrobial drugs in order to reduce drug toxicity, side effects, and resistance to single agents. Mentha x piperita, known worldwide as "Mentha of Pancalieri", is produced locally at Pancalieri (Turin, Italy). The EO from this Mentha species is considered as one of the best mint EOs in the world. In our research, we assessed the antifungal activity of "Mentha of Pancalieri" EO, either alone or in combination with azole drugs (fluconazole, itraconazole, ketoconazole) against a wide panel of yeast and dermatophyte clinical isolates. The EO was analyzed by GC-MS, and its antifungal properties were evaluated by minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) parameters, in accordance with the CLSI guidelines, with some modifications. The interaction of EO with azoles was evaluated through the chequerboard and isobologram methods. The results suggest that this EO exerts a fungicidal activity against yeasts and a fungistatic activity against dermatophytes. Interaction studies with azoles indicated mainly synergistic profiles between itraconazole and EO vs. Candida spp., Cryptococcus neoformans, and Trichophyton mentagrophytes. Thus, the "Mentha of Pancalieri" EO may act as a potential antifungal agent and could serve as a natural adjuvant for fungal infection treatment.


Assuntos
Antifúngicos/farmacologia , Azóis/farmacologia , Mentha piperita/química , Monoterpenos/farmacologia , Óleos Voláteis/química , Animais , Antifúngicos/química , Antifúngicos/isolamento & purificação , Arthrodermataceae/efeitos dos fármacos , Arthrodermataceae/crescimento & desenvolvimento , Arthrodermataceae/isolamento & purificação , Candida/efeitos dos fármacos , Candida/crescimento & desenvolvimento , Candida/isolamento & purificação , Cryptococcus/efeitos dos fármacos , Cryptococcus/crescimento & desenvolvimento , Cryptococcus/isolamento & purificação , Combinação de Medicamentos , Sinergismo Farmacológico , Fluconazol/farmacologia , Guias como Assunto , Humanos , Itraconazol/farmacologia , Cetoconazol/farmacologia , Testes de Sensibilidade Microbiana , Monoterpenos/química , Monoterpenos/isolamento & purificação , Óleos Voláteis/isolamento & purificação
5.
Fitoterapia ; 138: 104290, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31398448

RESUMO

Six new monoterpene glycosides, named 6'-O-nicotinoylalbiflorin (1), 4'-O-vanillylalbiflorin (2), paeonidanin L (3), paeoniflorigenin-1-O-ß-d-xyloside (4), 6'-(2-hydroxypropanoyl)-paeoniflorin (5), oxylactiflorin (6), together with 16known ones (7-22) were isolated from the 70% ethanol extract of Paeoniae Radix. Their structures were elucidated based on spectroscopic analysis (1D and 2D NMR, HRESIMS, IR and UV), chemical evidences and comparison with literatures. The inhibitory effects of all the isolates were evaluated against lipopolysaccharide (LPS) stimulated PGE2 production in RAW 264.7 macrophages.


Assuntos
Anti-Inflamatórios/farmacologia , Glicosídeos/farmacologia , Monoterpenos/farmacologia , Paeonia/química , Raízes de Plantas/química , Animais , Anti-Inflamatórios/isolamento & purificação , China , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/isolamento & purificação , Camundongos , Estrutura Molecular , Monoterpenos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7
6.
Chem Pharm Bull (Tokyo) ; 67(7): 675-689, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31257323

RESUMO

An Orobanchaceae plant Cistanche tubulosa (SCHENK) WIGHT (Kanka-nikujuyou in Japanese), which is one of the authorized plant resources as Cistanches Herba in both Japanese and Chinese Pharmacopoeias, is a perennial parasitic plant growing on roots of sand-fixing plants. The stems of C. tubulosa have traditionally been used for treatment of impotence, sterility, lumbago, and body weakness as well as a promoting agent of blood circulation. In recent years, Cistanches Herba has also been widely used as a health food supplement in Japan, China, and Southeast Asian countries. Here we review our recent studies on chemical constituents from the stems of C. tubulosa as well as their bioactivities such as vasorelaxtant, hepatoprotective, and glucose tolerance improving effects.


Assuntos
Produtos Biológicos/química , Cistanche/química , Animais , Aorta Torácica/efeitos dos fármacos , Aorta Torácica/metabolismo , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Cistanche/metabolismo , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Caules de Planta/química , Caules de Planta/metabolismo , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Vasodilatadores/química , Vasodilatadores/isolamento & purificação , Vasodilatadores/farmacologia
7.
Molecules ; 24(12)2019 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-31234360

RESUMO

Volatile terpenes represent the largest group of Cannabis sativa L. components and they are responsible for its aromatic properties. Even if many studies on C. sativa have been focused on cannabinoids, which are terpenophenolics, little research has been carried out on its volatile terpenic compounds. In the light of all the above, the present work was aimed at the chemical characterization of seventeen essential oils from different fibre-type varieties of C. sativa (industrial hemp or hemp) by means of GC-MS and GC-FID techniques. In total, 71 compounds were identified, and the semi-quantitative analysis revealed that α- and ß-pinene, ß-myrcene and ß-caryophyllene are the major components in all the essential oils analysed. In addition, a GC-MS method was developed here for the first time, and it was applied to quantify cannabinoids in the essential oils. The antibacterial activity of hemp essential oils against some pathogenic and spoilage microorganisms isolated from food and food processing environment was also determined. The inhibitory effects of the essential oils were evaluated by both the agar well diffusion assay and the minimum inhibitory concentration (MIC) evaluation. By using the agar diffusion method and considering the zone of inhibition, it was possible to preliminarily verify the inhibitory activity on most of the examined strains. The results showed a good antibacterial activity of six hemp essential oils against the Gram-positive bacteria, thus suggesting that hemp essential oil can inhibit or reduce bacterial proliferation and it can be a valid support to reduce microorganism contamination, especially in the food processing field.


Assuntos
Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Cannabis/química , Óleos Voláteis/farmacologia , Antibacterianos/química , Bactérias/patogenicidade , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/isolamento & purificação , Canabinoides/química , Cromatografia Gasosa-Espectrometria de Massas , Testes de Sensibilidade Microbiana , Monoterpenos/química , Monoterpenos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Terpenos/química
8.
Phytochemistry ; 164: 236-242, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31185420

RESUMO

Mangiterpenes A-C and 2',3'-seco-manginoid C, four undescribed sesquiterpene/monoterpene-shikimate-conjugated meroterpenoids with spiro ring systems, were isolated from Guignardia mangiferae. The structures and absolute configurations of these compounds were established by comprehensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Mangiterpenes A-C represent the first examples of sesquiterpene-shikimate-conjugated spirocyclic meroterpenoids, and 2',3'-seco-manginoid C features an unexpected 2',3'-seco-manginoids skeleton. Mangiterpene C strongly inhibited the production of NO inducted by LPS, with an IC50 value of 5.97 µM. It showed an anti-inflammatory effect by means of blocking in the NF-κB signaling pathway and decreasing the expression of inflammatory mediators.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Monoterpenos/farmacologia , Ácido Chiquímico/farmacologia , Compostos de Espiro/farmacologia , Terpenos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Relação Dose-Resposta a Droga , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , NF-kappa B/antagonistas & inibidores , NF-kappa B/metabolismo , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Ácido Chiquímico/química , Ácido Chiquímico/isolamento & purificação , Transdução de Sinais/efeitos dos fármacos , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificação
9.
Planta Med ; 85(11-12): 941-946, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31163460

RESUMO

Targeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3',4'-trihydroxy-5,5'-diisopropyl-2,2'-dimethylbiphenyl (1: ), together with two known p-cymene derivatives (2: and 3: ), as well as five known compounds, namely, thymol (4: ), oleanolic acid (5: ), ursolic acid (6: ), cirsimaritin (7: ), and xanthomicrol (8: ). The structural elucidation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2: and 3: showed negligible activity on tyrosinase, while compound 1: effectively inhibited the enzyme with 35% (± 0.3) inhibitory activity, higher than the inhibition of the reference compound kojic acid (18.6 ± 0.02).


Assuntos
Cromatografia Gasosa-Espectrometria de Massas/métodos , Espectroscopia de Ressonância Magnética/métodos , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monoterpenos/isolamento & purificação , Extratos Vegetais/química , Thymus (Planta)/química , Flavonas/farmacologia , Monoterpenos/farmacologia , Ácido Oleanólico/farmacologia , Timol/farmacologia , Triterpenos/farmacologia
10.
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
11.
J Oleo Sci ; 68(7): 671-677, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-31178467

RESUMO

Conifer resins are used as chemical raw materials for daily necessities. There have been many reports on the aroma components of turpentine oil from rosin, but there has been no reports on fluctuations in the aroma components through spring to late autumn. We speculated that the aroma components in the essential oils of deciduous coniferous larches might fluctuate during maturation of the foliage. In this study, we focused on the aroma components of larch essential oils and we clarified by multivariate analysis how the aroma components fluctuate during leaf maturation. The results of analysis showed that there was a drastic seasonal fluctuation of the chemical components in larch essential oils, especially in senescent leaves in late autumn. Cryptone and linalool were identified as the characteristic aroma components in essential oil from senescent larch leaves.


Assuntos
Larix/química , Odorantes/análise , Óleos Voláteis/química , Folhas de Planta/química , Estações do Ano , Terebintina/química , Monoterpenos/isolamento & purificação , Óleos Voláteis/isolamento & purificação , Folhas de Planta/crescimento & desenvolvimento , Resinas Vegetais
12.
J Chem Ecol ; 45(5-6): 455-463, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31140030

RESUMO

The spherical mealybug Nipaecoccus viridis is a pest of several major crops including soybeans, grapes and citrus varieties. Sessile virgin females of N. viridis release two volatiles, 2,2,3,4-tetramethyl-3-cyclopentene-1-methanol (γ-necrodol) and γ-necrodyl isobutyrate, on a circadian rhythm with peak at 17:00 (11 hr of photophase) as determined by automated, sequential solid phase micro extraction with gas chromatography-mass spectrometry analysis. The females increased the released amounts with age by about seven-fold from 5 to 6 d to 10-12 d of age. trans-3,4,5,5-Tetramethyl-2-cyclopentene-1-methanol (trans-α-necrodol) and trans-α-necrodyl acetate, found in essential oil of Spanish lavender, Lavandula luisieri, were rearranged to γ-necrodol and then used to synthesize γ-necrodyl isobutyrate. GC-MS and NMR data confirmed the identifications. In a petri dish bioassay, N. viridis males were significantly attracted to filter paper discs impregnated with γ-necrodyl isobutyrate but not to γ-necrodol or controls. A mixture of the two compounds was not more attractive than γ-necrodyl isobutyrate alone. Similar results were obtained with trapping flying adults, suggesting that the sex pheromone consists only of γ-necrodyl isobutyrate. This compound has not been reported previously in insects. Conversion of α-necrodol in lavender essential oil simplifies the synthesis of the sex pheromone and should allow its use in management of this cosmopolitan invasive pest.


Assuntos
Hemípteros/química , Atrativos Sexuais/química , Animais , Ciclopentanos/química , Ciclopentanos/isolamento & purificação , Ciclopentanos/farmacologia , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Hemípteros/fisiologia , Isomerismo , Espectroscopia de Ressonância Magnética , Masculino , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Atrativos Sexuais/isolamento & purificação , Atrativos Sexuais/farmacologia , Comportamento Sexual Animal/efeitos dos fármacos , Microextração em Fase Sólida
13.
Mar Drugs ; 17(4)2019 Apr 17.
Artigo em Inglês | MEDLINE | ID: mdl-30999651

RESUMO

The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (2-5) as well as undescribed compounds of the same class, anverenes B-D (6-8). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy and negative chemical ionization mass spectrometry. Compounds 1-9 show moderate cytotoxicity against cervical cancer (HeLa) cells.


Assuntos
Monoterpenos/química , Monoterpenos/farmacologia , Plocamium/química , Regiões Antárticas , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Células HeLa , Humanos , Hidrocarbonetos Halogenados/química , Hidrocarbonetos Halogenados/isolamento & purificação , Hidrocarbonetos Halogenados/farmacologia , Concentração Inibidora 50 , Conformação Molecular , Monoterpenos/isolamento & purificação , Ressonância Magnética Nuclear Biomolecular
14.
Chem Biodivers ; 16(6): e1900059, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30969463

RESUMO

Seseli libanotis is an aromatic umbelliferous plant distributed sporadically on dry grassland edges in Europe and Western Asia. The essential oil composition in the different plant parts was studied from plants collected on nine sites in Austria and one site in Alto Adige, Italy. Monoterpenes such as α-pinene, sabinene and ß-myrcene and the sesquiterpene germacrene D were present in all essential oils from the aerial parts. Inflorescences and fruits had the highest essential oil contents. These essential oils from four sites were rich in acorenone B, while from other three sites they had carotol as a major component. Osthole as furocoumarin occurred in some oils. The root essential oils were dominated by α-pinene. The essential oil variability has been studied by principal component analysis (PCA) and discriminant analysis (DA) with plant parts or sampling site as a priori groups. PCA could well separate inflorescence and fruit essential oil samples from leaf and stem essential oil samples. DA differentiated well between the plant parts and most of the sampling sites.


Assuntos
Apiaceae/química , Óleos Voláteis/química , Apiaceae/metabolismo , Análise Discriminante , Europa (Continente) , Frutas/química , Frutas/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/química , Monoterpenos/isolamento & purificação , Análise de Componente Principal
15.
Biosci Biotechnol Biochem ; 83(6): 986-995, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30836860

RESUMO

Our previous work has reported an anti-proliferative compound from moutan cortex, paeoniflorigenone which can induce cancer-selective apoptosis. However, its anti-proliferative mechanism is still unknown. According to morphology changes (hypertrophy and flattening), we hypothesized that PFG can induce senescence or inhibit cell mitosis. Here we show that PFG can induce cellular senescence, evidenced by the expression of senescence-associated ß-galactosidase, G0/G1 cell cycle arrest and permanent loss of proliferative ability, in normal TIG-1 diploid fibroblast but not cancerous HeLa cells. In cancerous HeLa cells, PFG inhibited proliferation by inducing S and G2/M cell cycle arrest and mitosis inhibition. DNA damage response was activated by PFG, interestingly the reactive oxygen species level was suppressed instead of escalated. To sum up, we report 3 new roles of PFG as, 1. inducer of premature senescence in normal TIG-1 cells, 2. inhibitor of mitosis in cancerous HeLa cells, 3. ROS scavenger. Abbreviations: PFG: Paeoniflorigenone; ROS: reactive oxygen species; ATM: ataxia telangiectasia mutated; t-BHP: tert-butyl hydroperoxide; SA-ß-gal: senescence-associatedß-galactosidase; DNA-PKcs: DNA-dependent protein kinase; γ-H2AX: H2AX phosphoryla-tion at Ser-139.


Assuntos
Senescência Celular/efeitos dos fármacos , Diploide , Fibroblastos/efeitos dos fármacos , Mitose/efeitos dos fármacos , Monoterpenos/farmacologia , Paeonia/química , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Células Cultivadas , Dano ao DNA/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ativação Enzimática , Fibroblastos/citologia , Fibroblastos/enzimologia , Citometria de Fluxo , Imunofluorescência , Depuradores de Radicais Livres/farmacologia , Células HeLa , Humanos , Monoterpenos/administração & dosagem , Monoterpenos/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , beta-Galactosidase/metabolismo
16.
Chem Biodivers ; 16(5): e1900051, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30875445

RESUMO

The genus Euphorbia attracted the attention of many researchers worldwide from natural products, bioactivity, and ecological perspective. The essential oils (EOs) of Euphorbia heterophylla are poorly studied. Therefore, the present study aimed to provide a detailed profile of the E. heterophylla EOs as well as to determine their antioxidant and allelopathic activities. The EOs from aerial parts of E. heterophylla were extracted using hydrodistillation and analyzed via GC/MS. The antioxidant activity was determined based on scavenging of the free radical, 1,1-diphenyl-2-picrylhydrazyl and H2 O2 . Various concentrations of the EOs were tested against the noxious weed, Cenchrus echinatus. Thirty-five compounds were identified representing 100 % of the total mass. Four classes of components were characterized, among which terpenoids were the main components (88.70 %). Monoterpenes represented the main class (69.48 %), followed by sesquiterpenes (18.63 %), and only one diterpenoid, kaur-16-ene, was identified. 1,8-Cineole (32.03 %), camphor (16.54 %), ß-elemene (5.92 %), endo-borneol (4.94 %), limonene (4.27 %), pentatriacontane (3.91 %), and α-pinene (3.89 %) were the major compounds. The EOs composition of Egyptian E. heterophylla ecospecies was comparable to that of other reported Euphorbia species, although it showed no correlation with Nigerian E. heterophylla ecospecies. The EOs from E. heterophylla aerial parts exhibited significant antioxidant activity. Moreover, a concentration of 100 µL L-1 of the EOs reduced the germination, root, and shoot growth of C. echinatus by about 93.95 %, 84.6 %, and 57.8 %, respectively. Therefore, the EOs from E. heterophylla could be integrated into the control of this weed, as eco-friendly biocontrol method. Further study is needed to characterize their allelopathic activity under field conditions as well as to evaluate their durability and biosafety.


Assuntos
Antioxidantes/química , Euphorbia/química , Herbicidas/química , Óleos Voláteis/química , Cânfora/química , Cânfora/isolamento & purificação , Cânfora/farmacologia , Cenchrus/efeitos dos fármacos , Cenchrus/crescimento & desenvolvimento , Análise por Conglomerados , Euphorbia/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Herbicidas/farmacologia , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
17.
Mini Rev Med Chem ; 19(11): 902-912, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30864526

RESUMO

BACKGROUND: In this study, the essential oil composition and cytotoxic activities of five Artemisia species were determined. METHODS: The collected plants were water-distilled separately to obtain oils which were then subjected to gas chromatography (GC) and gas chromatography/mass spectrometry GC/MS analyses to identify their compositions. Cancer cells were exposed to different concentrations of samples and cell viability was measured using AlamarBlue® assay. Apoptotic cells were analyzed by propidium iodide (PI) staining and flow cytometry. RESULTS & CONCLUSION: To study the amount of pro-apoptotic proteins and the apoptosis mechanism, Western blot method was used. Although all samples were cytotoxic at the highest concentration, the oil of A. kulbadica showed the strongest activity among other plants. Carvacrol (IC50 21.11 µg/ml) had the most cytotoxic effects among other components. Carvacrol, 1,8-cineole and 4-terpineole caused an increase in the amount of Bax protein and cleaved peroxisome proliferator-activated receptors (PPAR) and caspase proteins in DU 145 cells.


Assuntos
Artemisia/química , Óleos Voláteis/análise , Apoptose/efeitos dos fármacos , Artemisia/metabolismo , Caspases/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Receptores Ativados por Proliferador de Peroxissomo/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Proteína X Associada a bcl-2/metabolismo
18.
Fitoterapia ; 134: 435-442, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30898726

RESUMO

Sapium baccatum has been traditionally used as therapeutic remedies. To support its medicinal benefits, our current phytochemical investigation attempted to further discover novel bioactive compounds from S. baccatum. Eight new phenolic compounds, namely, seven coumarins (1-7) and one monoterpene galloylglycoside (8), together with 23 (9-31) known compounds were isolated. Their structures were determined by extensive spectroscopic methods and comparison with literatures. The three pairs of enantiomers of 1, 2 and 7 were confirmed on the basis of HPLC chiral analysis, electronic circular dichroism data and optical rotations. Two coumarins (1-2) were proven to be artifacts through HPLC analysis. The inhibitory effects on TNF-α secretion were examined biologically in LPS-induced BV2 microglia cells and all of the tested compounds exhibited significant inhibitory activity, especially new compound 1 possessed stronger inhibitory effects compared to the positive control quercetin. In addition, compounds 14 and 15 showed weak antifungal activity against Candida albicans SC5314 with MIC values both at 64 µg/mL. The results laid a solid foundation for additional research on S.baccatum related to its anti-inflammatory and antifungal medicinal value.


Assuntos
Cumarínicos/farmacologia , Monoterpenos/farmacologia , Sapium/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Linhagem Celular , China , Cumarínicos/isolamento & purificação , Camundongos , Estrutura Molecular , Monoterpenos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Casca de Planta/química
19.
Phytochem Anal ; 30(4): 456-463, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30859657

RESUMO

INTRODUCTION: Calcium channel blockers (CCBs) are currently the most commonly used drugs for the treatment of hypertension. Moutan Cortex (MC), a traditional Chinese herb, has been found to have an anti-hypertensive effect. However, its potential mechanisms in the regulation of intracellular calcium concentration ([Ca2+ ]i ) remain poorly understood. OBJECTIVE: The main objective of this work was to identify the potential calcium antagonists from MC and study their molecular mechanisms. METHODS: Ultra-high performance liquid chromatography-quadrupole-time-of-fight-mass spectrometry (UHPLC-QTOF-MS) analysis combined with a dual-luciferase reporter assay was utilised to systematically screen the calcium antagonistic active ingredients in the methanol extract of MC. Additionally, the molecular mechanism of these compounds was further studied using live-cell imaging analysis with the calcium ion (Ca2+ ) probe dye fluo-4/AM to monitor changes in [Ca2+ ]i . RESULTS: Three monoterpenoids (paeoniflorin, benzoylpaeoniflorin and mudanpioside C), one phenolic acid (paeonol) and one gallotannin (1,2,3,4,6-O-pentagalloylglucose) were screened out as potential calcium antagonists in MC. Among them, the calcium antagonistic activity of benzoylpaeoniflorin, mudanpioside C and 1,2,3,4,6-O-pentagalloylglucose is first reported. Additionally, paeoniflorin, benzoylpaeoniflorin, mudanpioside C and paeonol can effectively block voltage-operated Ca2+ channels (VOCCs) to exert calcium antagonism, while 1,2,3,4,6-O-pentagalloylglucose plays a role in blocking inositol 1,4,5-trisphosphate receptors (IP3Rs). CONCLUSION: This work indicated that the anti-hypertensive efficacy of MC acted through multiple components selectively antagonising multiple cell signalling pathways to regulate [Ca2+ ]i . Furthermore, they could be considered as a reference standard for controlling the quality of Chinese medicinal materials.


Assuntos
Bloqueadores dos Canais de Cálcio/isolamento & purificação , Cálcio/metabolismo , Medicamentos de Ervas Chinesas/química , Hipertensão/tratamento farmacológico , Monoterpenos/química , Paeonia/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Animais , Bloqueadores dos Canais de Cálcio/química , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Genes Reporter , Humanos , Receptores de Inositol 1,4,5-Trifosfato/metabolismo , Medicina Tradicional Chinesa , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Ratos , Espectrometria de Massas em Tandem
20.
Artigo em Inglês | MEDLINE | ID: mdl-30739881

RESUMO

A general method for efficient and selective extraction of a target compound from complex natural products remains elusive, despite decades of research. By introducing a functional amido group on the surface of dispersity-enhanced magnetic nanoparticles, a nanoparticle receptor to selectively recognize Sibiskoside (a monoterpene) from the aerial portion of Sibiraea angustata by hydrogen bond interaction was synthesized. The superparamagnetic Fe3O4 nanoparticles were successively modified with tetraethyl orthosilicate (TEOS), amino and amido functional groups, and 4-vinylbenzoic acid (VBZA) was used as the functional monomer. A thin layer of poly (VBZA) imprinted with Sibiskoside was immobilized on the surface of magnetic carriers. Attributing to the amido group introduced into the magnetic particles, the template could attract and bind to the surface and promote the formation of a hydrogen bond system between the carrier, template molecules and functional monomer. High-density molecular recognition sites grew on the surface of magnetic substrate. The adsorption reached equilibrium at approximately 150 min, while fast adsorption occurred during the first 60 min. The maximum adsorption capacity has been found to be 13.75 mg g-1 according to calculation with the Langmuir isotherm. The selectivity coefficients of Molecular imprinting polypers (MIPs) for Sibiskoside with respect to Andrographolide, Loganin, Gastrodin, geraniol-1-O-[α-l-rhamnopyranosyl-(1 → 6)-1-ß-d-glucopyranoside] (GRG), Sibiscolacton and Sibiraic acid were 2.26, 1.43, 1.701.56, 1.05, 0.73 and, respectively. The results indicated that the MIPs possessed good specific adsorption capacity and selectivity toward Sibiskoside and had the potential to be a candidate for the separation and purification of monoterpenes from Sibiraea angustata, which is of great significance to obesity management.


Assuntos
Glicosídeos/isolamento & purificação , Nanopartículas de Magnetita/química , Impressão Molecular/métodos , Monoterpenos/isolamento & purificação , Rosaceae/química , Cromatografia Líquida de Alta Pressão , Glicosídeos/análise , Monoterpenos/análise , Extratos Vegetais/química , Propriedades de Superfície
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