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Article in Chinese | WPRIM | ID: wpr-878981


To compare the effect of hot or warm property of Chinese medicine(CM) on the skin toxicity of essential oils(EOs) as penetration enhancer in vitro and in vivo, and explore the mechanism. EOs were extracted from WIM of Bichengqie(Litseae Fructus), Dingxiang(Flos Syzygii Aromatici), Huajiao(Pericarpium Zanthoxyli Bungeani), and Xiaohuixiang(Fructus Foeniculi) with warm property, and Ganjiang(Rhizoma Zingiberis), Gaoliangjiang(Rhizoma Alpiniae Officinari), Hujiao(Fructus Piperis), and Wuzhuyu(Fructus Evodiae Rutaecarpae) with hot property, respectively. Then the in vitro toxicity was evaluated by human keratinocyte cytotoxicity. In vivo skin irritation potency was also evaluated through pathological observation after topical administration. The components, especially those located in stratum corneum, were analyzed by GC-MS. The main components, namely monoterpenes and sesquiterpenes, of EOs extracted from CM with hot property,were detected for the interaction with keratino-lipid ceramide 3 by molecular simulation technology; and the interaction energy value was calculated based on the optimal conformation. It was found that the skin cell toxicity of EOs from CM with hot property was significantly higher than that of EOs from CM with warm property. However, there was no significant difference between them by in vivo skin irritation evaluation. Whether from CM with hot property or warm property, EOs showed a significant reduced toxicity compared with azone. Sesquiterpenes(33.56%±19.38%) were found to be one of the main components in EOs from CM with hot property, while almost no sesquiterpenes was found in EOs from CM with warm property. After topical administration of EOs from CM with hot property, sesquiterpenes were demonstrated to be prone to locate in stratum corneum. The results of molecular simulation also revealed that the interaction between sesquiterpenes and ceramide 3 was significantly stronger than that of monoterpenes(P<0.01). In conclusion, the location of sesquiterpenes in stratum corneum resulted in the significant difference between in vitro skin cell toxicity and in vivo skin irritation potency. The EOs from CM with hot property shall be taken into account for further development of potent penetration enhancer.

Humans , Monoterpenes/metabolism , Oils, Volatile/toxicity , Sesquiterpenes/metabolism , Skin/metabolism , Skin Absorption
Bol. latinoam. Caribe plantas med. aromát ; 18(4): 435-443, jul. 2019. ilus, tab
Article in English | LILACS | ID: biblio-1008258


Volatiles compounds are involved in defensive induction against insects, playing an important role in insect-plant interaction being induced by response to mechanical damage. However, they could decrease according to the domestication degree in cultivated plants. Currently, it has been established that secondary metabolites are reduced due to the domestication process in murtilla. Hence, the follow question emerges: Are volatile organic compounds induced by mechanical damage reduced in cultivated murtilla plants in relation to wild plants? Two cultivated ecotypes and their respective wild counterparts were sampled. Volatiles compounds were obtained using Porapak-Q columns and analyzed by gas chromatography. Results showed that compounds as 2-hexanone, α-pinene, 2-thujene, 3-thujene and 1,8- cineole were more abundant in wild plants exposed to a mechanical damage than cultivated plants. Hence, these compounds have been associated to induced defense, these results suggest that domestication reduced the induction of defensive volatiles in cultivated murtilla in response to mechanical damage.

Los compuestos volátiles están implicados en la defensa inducida contra insectos, desempeñando un papel importante en esta interacción. Sin embargo, estos compuestos podrían disminuir según el grado de domesticación. Actualmente, se ha reportado que algunos metabolitos secundarios son reducidos en plantas de murtilla domesticadas. Por lo tanto, surge la siguiente pregunta de investigación: ¿Los compuestos orgánicos volátiles inducidos por el daño mecánico son reducidos en plantas cultivadas de murtilla en comparación con plantas silvestres? Para dos ecotipos cultivados y sus respectivas contrapartes silvestres, los compuestos volátiles fueron capturados usando columnas de Porapak-Q y las muestras analizadas por cromatografía gaseosa. Los resultados mostraron que compuestos tales como 2- hexanona, α-pineno, 2-tujeno, 3-tujeno y 1,8-cineol fueron más abundantes en plantas silvestres expuestas a daño mecánico que en cultivadas. Debido a que estos compuestos se han asociado a defensa inducida, estos resultados sugieren que la domesticación reduce la inducción de volátiles en plantas cultivadas sometidas a daño mecánico.

Animals , Oils, Volatile/metabolism , Myrtaceae/metabolism , Myrtaceae/microbiology , Domestication , Insecta/physiology , Sesquiterpenes/analysis , Sesquiterpenes/metabolism , Oils, Volatile/chemistry , Myrtaceae/chemistry , Monoterpenes/analysis , Monoterpenes/metabolism , Wilderness , Larva/physiology , Gas Chromatography-Mass Spectrometry
Biol. Res ; 49: 1-5, 2016. ilus, graf, tab
Article in English | LILACS | ID: biblio-950857


BACKGROUND: α-Farnesene is a volatile sesquiterpene synthesized by the plant mevalonate (MVA) pathway through the action of α-farnesene synthase. The α-farnesene synthase 1 (MdAFS1) gene was isolated from apple peel (var. white winterpearmain), and transformed into tobacco (Nicotiana tabacum NC89). The transgenic plants had faster stem elongation during vegetative growth and earlier flowering than wild type (WT). Our studies focused on the transgenic tobacco phenotype. RESULTS: The levels of chlorophyll and soluble protein decreased and a lower seed biomass and reduced net photosynthetic rate (Pn) in transgenic plants. Reactive oxygen species (ROS) such as hydrogen peroxide (H2O2) and superoxide radicals (O2._) had higher levels in transgenics compared to controls. Transgenic plants also had enhanced sensitivity to oxidative stress. The transcriptome of 8-week-old plants was studied to detect molecular changes. Differentially expressed unigene analysis showed that ubiquitin-mediated proteolysis, cell growth, and death unigenes were upregulated. Unigenes related to photosynthesis, antioxidant activity, and nitrogen metabolism were downregulated. Combined with the expression analysis of senescence marker genes, these results indicate that senescence started in the leaves of the transgenic plants at the vegetative growth stage. CONCLUSIONS: The antioxidative defense system was compromised and the accumulation of reactive oxygen species (ROS) played an important role in the premature aging of transgenic plants.

Tobacco/physiology , Plants, Genetically Modified/physiology , Antioxidants/physiology , Photosynthesis/physiology , Sesquiterpenes/analysis , Sesquiterpenes/metabolism , Time Factors , Tobacco/genetics , Genetic Markers , Gene Expression/physiology , Plants, Genetically Modified/genetics , Reactive Oxygen Species/analysis , Reactive Oxygen Species/metabolism , Superoxides/analysis , Superoxides/metabolism , Plant Leaves/physiology , Oxidative Stress/physiology , Gene Expression Regulation, Plant/physiology , Real-Time Polymerase Chain Reaction , Hydrogen Peroxide/analysis , Hydrogen Peroxide/metabolism
Braz. j. microbiol ; 44(4): 1285-1290, Oct.-Dec. 2013. ilus, tab
Article in English | LILACS | ID: lil-705269


Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.

Anti-Infective Agents/metabolism , Flammulina/metabolism , Sesquiterpenes/metabolism , Biosynthetic Pathways , /metabolism
Article in English | WPRIM | ID: wpr-49339


Matrix metalloproteinase-9 (MMP-9) may play an important role in emphysematous change in chronic obstructive pulmonary disease (COPD), one of the leading causes of mortality and morbidity worldwide. We previously reported that simvastatin, an inhibitor of HMG-CoA reductase, attenuates emphysematous change and MMP-9 induction in the lungs of rats exposed to cigarette smoke. However, it remained uncertain how cigarette smoke induced MMP-9 and how simvastatin inhibited cigarette smoke-induced MMP-9 expression in alveolar macrophages (AMs), a major source of MMP-9 in the lungs of COPD patients. Presently, we examined the related signaling for MMP-9 induction and the inhibitory mechanism of simvastatin on MMP-9 induction in AMs exposed to cigarette smoke extract (CSE). In isolated rat AMs, CSE induced MMP-9 expression and phosphorylation of ERK and Akt. A chemical inhibitor of MEK1/2 or PI3K reduced phosphorylation of ERK or Akt, respectively, and also inhibited CSE-mediated MMP-9 induction. Simvastatin reduced CSE-mediated MMP-9 induction, and simvastatin-mediated inhibition was reversed by farnesyl pyrophosphate (FPP) or geranylgeranyl pyrophosphate (GGPP). Similar to simvastatin, inhibition of FPP transferase or GGPP transferase suppressed CSE-mediated MMP-9 induction. Simvastatin attenuated CSE-mediated activation of RAS and phosphorylation of ERK, Akt, p65, IkappaB, and nuclear AP-1 or NF-kappaB activity. Taken together, these results suggest that simvastatin may inhibit CSE-mediated MMP-9 induction, primarily by blocking prenylation of RAS in the signaling pathways, in which Raf-MEK-ERK, PI3K/Akt, AP-1, and IkappaB-NF-kappaB are involved.

Phosphatidylinositol 3-Kinase/metabolism , Alkyl and Aryl Transferases/metabolism , Animals , Anticholesteremic Agents/pharmacology , Cells, Cultured , Enzyme Inhibitors/metabolism , Extracellular Signal-Regulated MAP Kinases/metabolism , Gene Expression Regulation, Enzymologic/drug effects , I-kappa B Kinase/antagonists & inhibitors , Macrophages, Alveolar/cytology , Matrix Metalloproteinase 9/genetics , Mitogen-Activated Protein Kinase Kinases/metabolism , Polyisoprenyl Phosphates/metabolism , Proto-Oncogene Proteins c-akt/metabolism , Rats , Sesquiterpenes/metabolism , Signal Transduction/physiology , Simvastatin/pharmacology , Smoke/adverse effects , Tobacco/adverse effects
Indian J Exp Biol ; 2000 Oct; 38(10): 1050-3
Article in English | IMSEAR | ID: sea-56555


Phenolics, anthocyanin and alpha-bisabolol production from poplar (Populus delotides) in tissue culture was determined. A number of phenolic acids were identified by HPLC. PAL activity in response to phytohormones, cells growth and anthocyanin production showed a positive correlation. A component, alpha-bisabolol, was identified using gas chromatography and UV spectroscopy. In vitro production of said metabolites was influenced by phytohormones.

Ammonia-Lyases/metabolism , Anthocyanins/metabolism , Cells, Cultured , Sesquiterpenes/metabolism , Trees/cytology