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Variability in biogenic volatile organic compound (BVOC) emissions across species and seasons poses challenges for accurate regional emission estimates and effective ozone (O3) control policies. To address this issue, we conducted in-situ measurements of emission factors for six dominant tree species in Beijing across four seasons. Subsequently, we developed monthly dynamic standard emission factors (SER-MDs) to model monthly BVOC emissions and their impacts on O3 formation at citywide and district levels. Our observations revealed pronounced seasonal differences in the BVOC composition and emission rates, as well as their responsiveness to monthly average temperature. By introducing the SER-MDs, we estimated BVOC emissions from the dominant tree species in Beijing to be 38.2 Gg yr-1, with monoterpenes and isoprene contributing 49% and 11%, respectively. This calculation reduced the overestimation associated with constant standard emission factors by 31%-38% at district level. The estimates also revealed regional differences in plant compositions rather than simple feedback from regional temperature and photosynthetically active radiation periods. Under these conditions, the maximum monthly BVOC-induced O3 concentration occurred in August and ranged from 4 to 17 µg m-3 across districts, with isoprene being the dominant contributor. Quercus mongolica and Populus tomentosa played significant roles in the formation of BVOC-induced O3 due to their strong isoprene emitting potential in July-August. These results indicate the necessity of introducing species-specific rhythms of BVOC emissions from dominant species in the development of urban BVOC emission inventories. This approach could inform the development of air pollution management policies that are consistent with the local vegetation composition and O3 pollution characteristics. For Beijing and other similar northern cities, reducing the use of tree species emitting substantial amounts of isoprene during periods of regional peak ambient O3 concentrations could constitute an effective nature-based solution for improving urban air quality in the future.
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[This corrects the article DOI: 10.3389/fpls.2022.1072931.].
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(-)-Carvone, a ketone monoterpene, is the main component of essential oils from several medicinal plants and has been reported to have anti-arthriric, anticonvulsive, antidiabetic, anti-inflammatory, anticancer, and immunomodulatory effects. Therefore, this study aimed to investigate the spasmolytic activity of (-)-carvone in rodent models. The isolated virgin rat uterus was mounted in an organ bath apparatus, and the relaxing effect of ( -)-carvone and its mechanism of action were evaluated in tonic contractions induced by carbachol, KCl, PGF2α, or oxytocin. The animal model of primary dysmenorrhea was replicated with the injection of estradiol benzoate in female mice for three consecutive days, followed by intraperitoneal administration of oxytocin. Non-clinical acute toxicity evaluation was also performed. (-)-Carvone potency and effectiveness were larger in carbachol (pEC50 = 5.41 ± 0.14 and Emax = 92.63 ± 1.90% at 10-3 M) or oxytocin (pEC50 = 4.29 ± 0.17 and Emax = 86.69 ± 1.56% at 10-3 M) contractions. The effect of ( -)-carvone was altered in the presence of 4-aminopyridine, glibenclamide, L-NAME, or methylene blue. Mice pre-treated with (-)-carvone at a dose of 100 mg/kg showed a significant reduction in the number of writhing after oxytocin administration. No toxicity was observed after oral administration of 1 g/kg ( -)-carvone. Taken together, we showed that (-)-carvone reduced writhing by a spasmolytic effect, probably through the participation of KV and KATP channels and the nitric oxide pathway.
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Although ozone (O3) pollution affects plant growth and monoterpene (MT) emissions, the responses of MT emission rates to elevated O3 and the related mechanisms are not entirely understood. To gain an insight into these effects and mechanisms, we evaluated physiological (leaf MT synthesis ability, including precursor availability and enzyme kinetics) and physicochemical limiting factors (e.g. leaf thickness of the lower and upper epidermis, palisade and spongy tissue, and size of resin ducts and stomatal aperture) affecting MT emissions simultaneously from two broad-leaved and two coniferous species after one growing season of field experiment. The effects of elevated O3 on MT emissions and the related mechanisms differed between plant functional types. Specifically, long-term moderate O3 exposure significantly reduced MT emissions in broad-leaved species, primarily attributed to a systematic decrease in MT synthesis ability, including reductions in all MT precursors, geranyl diphosphate content, and MT synthase protein levels. In contrast, the same O3 exposure significantly enhanced MT emissions in coniferous species. However, the change in MT emissions in coniferous species was not due to modifications in leaf MT synthesis ability but rather because of alterations in leaf anatomical structure characteristics, particularly the size of resin ducts and stomatal aperture. These findings provide an important understanding of the mechanisms driving MT emissions from different tree functional groups and can enlighten the estimation of MT emissions in the context of O3 pollution scenarios as well as the development of MT emission algorithms.
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Contaminantes Atmosféricos , Monoterpenos , Ozono , Hojas de la Planta , Tracheophyta , Contaminantes Atmosféricos/toxicidad , Monoterpenos/metabolismo , Hojas de la Planta/efectos de los fármacos , Tracheophyta/efectos de los fármacos , Tracheophyta/fisiologíaRESUMEN
Monoterpenoids are the main components of Mentha canadensis essential oil. Monoterpene biosynthetic pathways have been explored, but the regulatory mechanisms remain unclarified. We identified an abscisic acid (ABA)-inducible A-type basic leucine zipper (bZIP) transcription factor McbZIP1 that was localized in the nucleus and positively regulates monoterpene synthesis. McbZIP1 was expressed in most M. canadensis tissues and was induced under ABA, mannitol, and NaCl treatments. McbZIP1 had transcriptional activity in yeast and the N terminus (amino acids 75-117) was sufficient for transactivation. Yeast one-hybrid and Dual-Luciferase assays showed that McbZIP1 binds to ABA-responsive elements in the promoter region of limonene synthase gene. Yeast two-hybrid and biomolecular fluorescence complementation assays revealed that McbZIP1 interacts with McSnRK2.4. Overexpression of McbZIP1 in peppermint resulted in dramatically up-regulated monoterpene biosynthesis gene levels and increased menthol contents. The results support a transcriptional regulation mechanism in which McbZIP1 serves as a positive regulator of menthol biogenesis. These findings contribute to the molecular mechanism of monoterpenoid biogenesis, which may have uses in genetic engineering and menthol production.
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Regulación de la Expresión Génica de las Plantas , Mentha , Monoterpenos , Proteínas de Plantas , Mentha/metabolismo , Mentha/genética , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Monoterpenos/metabolismo , Ácido Abscísico/metabolismo , Factores de Transcripción con Cremalleras de Leucina de Carácter Básico/metabolismo , Factores de Transcripción con Cremalleras de Leucina de Carácter Básico/genética , Regiones Promotoras Genéticas , Plantas Modificadas GenéticamenteRESUMEN
Kaempferia subglobosa is a perennial medicinal plant in the Zingiberaceae family, identified as a new species in January 2024. To uncover the biological benefits of K. subglobosa and its compounds, investigation of the metabolites of the roots and rhizomes, yielded three new monoterpene-chalcone conjugates, the globosones A-C, representing a rare metabolite group within the Zingiberaceae, along with six known compounds. The biogenetic pathway for the globosones involves an oxidative [3+2] cycloaddition between α-phellandrene and 4'-methoxy-4,2',6'-trihydroxychalcone. Biological testing revealed potent xanthine oxidase (XO) inhibition by globosones A and B, with IC50 values of 7.0 ± 1.0 and 3.0 ± 0.2 µM, respectively, surpassing the positive control drug allopurinol (IC50 7.2 ± 0.1 µM). Globosones A-C also showed good aromatase inhibition (IC50 3.0-3.5 µM). Molecular docking studies indicated that globosones A and B may inhibit xanthine oxidase through binding at the FAD domain site. The physicochemical properties of these isolates suggest that they possess characteristics suitable for additional biological assessment in more advanced test systems. This study enhances an understanding of monoterpene-chalcone conjugate inhibitors of XO, and offers preliminary insights into the metabolites and bioactivities of K. subglobosa, uncovering potent biological activities associated with this newly discovered plant species.
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Aging is one of the risk factors involved in the development of erectile dysfunction (ED). Growing evidence suggests that oxidative stress is the critical mediator of changes in endothelial function and penile vascular tone in the aging process. Thus, reducing reactive oxygen species (ROS) levels may preserve the bioactivity of the penile vasculature. Antioxidant compounds, such as carvacrol, limit the damage caused by ROS and, therefore, benefit the treatment of ED. Thus, this study aims to evaluate the effects of carvacrol on ED using the D-( +)-galactose aging model. The animals were divided into five groups: control, D-( +)-galactose 150 mg/kg, carvacrol 50 mg/kg or 100 mg/kg, and sildenafil 1.5 mg/kg treated daily for 8 weeks. The physiological, functional, and morphological characteristics of aging-associated ED were evaluated after treatment with carvacrol. Carvacrol prevented ED in a D-( +)-galactose-induced aging model by reducing hypercontractility, enhancing endothelial dysfunction in the rat corpus cavernosum, and improving endothelial health of rat cavernous endothelial cells. In addition, carvacrol prevented the destruction of erectile components essential for penile erection and promoted a reduction of penile tissue senescence, probably through mechanisms that involve the harmful modulation of oxidative stress. Carvacrol significantly improved the erectile function of rats in a D-( +)-galactose-induced aging model and has excellent potential as a new therapeutic alternative in treating erectile dysfunction.
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BACKGROUND: Limonene has a variety of applications in the foods, cosmetics, pharmaceuticals, biomaterials, and biofuels industries. In order to meet the growing demand for sustainable production of limonene at industry scale, it is essential to find an alternative production system to traditional plant extraction. A promising and eco-friendly alternative is the use of microbes as cell factories for the synthesis of limonene. RESULTS: In this study, the oleaginous yeast Yarrowia lipolytica has been engineered to produce D- and L-limonene. Four target genes, l- or d-LS (limonene synthase), HMG (HMG-CoA reductase), ERG20 (geranyl diphosphate synthase), and NDPS1 (neryl diphosphate) were expressed individually or fused together to find the optimal combination for higher limonene production. The strain expressing HMGR and the fusion protein ERG20-LS was the best limonene producer and, therefore, selected for further improvement. By increasing the expression of target genes and optimizing initial OD, 29.4 mg/L of L-limonene and 24.8 mg/L of D-limonene were obtained. We also studied whether peroxisomal compartmentalization of the synthesis pathway was beneficial for limonene production. The introduction of D-LS and ERG20 within the peroxisome improved limonene titers over cytosolic expression. Then, the entire MVA pathway was targeted to the peroxisome to improve precursor supply, which increased D-limonene production to 47.8 mg/L. Finally, through the optimization of fermentation conditions, D-limonene production titer reached 69.3 mg/L. CONCLUSIONS: In this work, Y. lipolytica was successfully engineered to produce limonene. Our results showed that higher production of limonene was achieved when the synthesis pathway was targeted to the peroxisome, which indicates that this organelle can favor the bioproduction of terpenes in yeasts. This study opens new avenues for the efficient synthesis of valuable monoterpenes in Y. lipolytica.
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Leishmaniases, a group of neglected tropical diseases caused by an intracellular parasite of the genus Leishmania, have significant impacts on global health. Current treatment options are limited due to drug resistance, toxicity, and high cost. This study aimed to develop nanostructured lipid carriers (NLCs) for delivering Citrus sinensis essential oil (CSEO) and its main constituent, R-limonene, against leishmaniasis. The influence of surface-modified NLCs using chitosan was also examined. The NLCs were prepared using a warm microemulsion method, and surface modification with chitosan was achieved through electrostatic interaction. These nanocarriers were characterized by differential scanning calorimetry (DSC), X-ray diffraction (XRD), transmission electron microscopy, and dynamic light scattering (DLS). In vitro cytotoxicity was assessed in L929 and RAW 264.7 cells, and leishmanicidal activity was evaluated against promastigote and amastigote forms. The NLCs were spherical, with particle sizes ranging from 97.9 nm to 111.3 nm. Chitosan-coated NLCs had a positive surface charge, with zeta potential values ranging from 45.8 mV to 59.0 mV. Exposure of L929 cells to NLCs resulted in over 70 % cell viability. Conversely, surface modification significantly reduced the viability of promastigotes (93 %) compared to free compounds. Moreover, chitosan-coated NLCs presented a better IC50 against the amastigote forms than uncoated NLCs. Taken together, these findings demonstrate the feasibility of using NLCs to overcome the limitations of current leishmaniasis treatments, warranting further research.
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Supervivencia Celular , Quitosano , Citrus sinensis , Portadores de Fármacos , Limoneno , Lípidos , Nanopartículas , Aceites Volátiles , Aceites Volátiles/administración & dosificación , Aceites Volátiles/química , Aceites Volátiles/farmacología , Animales , Ratones , Limoneno/química , Limoneno/administración & dosificación , Limoneno/farmacología , Portadores de Fármacos/química , Células RAW 264.7 , Supervivencia Celular/efectos de los fármacos , Quitosano/química , Quitosano/administración & dosificación , Lípidos/química , Lípidos/administración & dosificación , Nanopartículas/química , Nanopartículas/administración & dosificación , Citrus sinensis/química , Antiprotozoarios/administración & dosificación , Antiprotozoarios/farmacología , Antiprotozoarios/química , Leishmaniasis/tratamiento farmacológico , Tamaño de la Partícula , Línea Celular , Leishmania/efectos de los fármacos , Terpenos/química , Terpenos/farmacología , Terpenos/administración & dosificación , Nanoestructuras/química , Nanoestructuras/administración & dosificaciónRESUMEN
The chemical composition and physical properties of secondary organic aerosol (SOA) generated through OH-initiated oxidation of mixtures containing ß-myrcene, an acyclic monoterpene, and d-limonene, a cyclic monoterpene, were investigated to assess the extent of the chemical interactions between their oxidation products. The SOA samples were prepared in an environmental smog chamber, and their composition was analyzed offline using ultraperformance liquid chromatography coupled with electrospray ionization high-resolution mass spectrometry (UPLC-ESI-HRMS). Our results suggested that SOA containing ß-myrcene showed a higher proportion of oligomeric compounds with low volatility compared to that of SOA from d-limonene. The formula distribution and signal intensities of the mixed SOA could be accurately predicted by a linear combination of the mass spectra of the SOA from individual precursors. Effects of cross-reactions were observed in the distribution of isomeric oxidation products within the mixed SOA, as made evident by chromatographic analysis. On the whole, ß-myrcene and d-limonene appear to undergo oxidation by OH largely independently from each other, with only subtle effects from cross-reactions influencing the yields of specific oxidation products.
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The market demand for essential oil containing citral is increasing. Our research group identified a rare chemotype of Camphora officinarum whose leaves are high in citral content by examining over 1000 wild trees across the entire native distribution area of C. officinarum in China. Because C. officinarum is suitable for large-scale cultivation, it is therefore seen as a promising source of natural citral. However, the molecular mechanism of citral biosynthesis in C. officinarum is poorly understood. In this study, transcriptomic analyses of C. officinarum with different citral contents revealed a strong positive correlation between the expression of a putative geraniol synthase gene (CoGES) and citral content. The CoGES cDNA was cloned, and the CoGES protein shared high similarity with other monoterpene synthases. Enzymatic assays of CoGES with geranyl diphosphate (GPP) as substrate yielded geraniol as the single product, which is the precursor of citral. Further transient expression of CoGES in Nicotiana benthamiana resulted in a higher relative content of geranial and the appearance of a new substance, neral. These findings indicate that CoGES is a geraniol synthase-encoding gene, and the encoded protein can catalyze the transformation of GPP into geraniol, which is further converted into geranial and neral through an unknown mechanism in vivo. These findings expand our understanding of citral biosynthesis in Lauraceae plants. Supplementary Information: The online version contains supplementary material available at 10.1007/s12298-024-01463-4.
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This study was conducted to determine the sea fennel essential oil (SFEO) yield, composition, and antioxidant activity of leaves, stem, inflorescences, and umbels from seeds of wild sea fennel (SF) (Crithmum maritimum L.) from the Montenegro coast. The chemical composition of isolated essential oil was determined by GC/MS and GC/FID analyses. The antioxidant activity was determined using the DPPH assay. The maximum SFEO yield was found in umbels with seeds (4.77 mL/100 g p.m.). The leaves contained less EO (0.52 mL/100 g p.m.) than immature inflorescence (0.83 mL/100 g p.m.) The minimum EO content was found in the stem (0.08%). Twenty components were isolated from SFEO leaves, twenty-four from inflorescence, thirty-four components from the stem, and twenty-one components from umbels with seeds. Limonene (62.4-72.0%), γ-terpinene (9.5-14.0%), α-pinene (1.4-5.8%), and sabinene (1-6.5%) were found to be the main components of the SFEO from monoterpene hydrocarbons as dominant grouped components (86% to 98.1%). SF plant parts showed differences in chemical profiles, especially in specific and low-represented ingredients. (E)-anethole (4.4%), fenchone (0.5%), and trans-carveol (0.2%) were present only in umbel with seeds, while the ß-longipipene (0.5%), (E)-caryophyllene (0.5%), and (2E)-decenal (0.2%) were found only in the stems. The degree of DPPH radical neutralization increased with incubation time. The SFEO isolated from the stems showed stronger antioxidant activity during the incubation times of 20 and 40 min (EC50 value of 5.30 mg/mL and 5.04 mg/mL, respectively) in comparison to the SFEO isolated from the other plant parts. The lowest antioxidant activity was obtained with the SFEO leaves (155.25 mg/mL and 58.30 mg/mL, respectively). This study indicates that SFEO possesses significant antioxidant activities and is animportant component in the food and pharmaceutical industries. It is important to preserve the existing gene pool and biodiversity with rational use SF for the extraction of high-quality essential oils.
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The chemical composition of extracts (CEs) and essential oils (EOs) from Tetradenia riparia leaves, flower buds, and stems was analyzed. Antiproliferative activity against tumor cell lines, NO production inhibition, and antioxidant and antiviral activities were assessed. The CEs contained flavonoids, phenolic acids, coumarins, and saturated fatty acids. The EOs included monoterpenes, oxygenated sesquiterpenes, and diterpenes. NO production inhibition ranged from 76 to 247 µg mL-1, and antiproliferative activity exhibited GI50 between 20 and >204 µg mL-1, with low cytotoxicity (SI: 1.08 to 4.75). Reactive oxygen species inhibition ranged from 45 to 82%. Antioxidant activity varied when determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay (IC50: 0.51 to 8.47 mg mL-1) and ferric reducing antioxidant power (0.35 to 0.81 µM ferrous sulfate per mg). The reduction in ß-carotene-linoleic acid co-oxidation varied between 76.13 and 102.25%. The total phenolic content of CEs and EOs was 10.70 to 111.68 µg gallic acid mg-1. Antiviral activity against herpes simplex virus type 1 (HSV-1) showed an EC50 between 9.64 and 24.55 µg mL-1 and an SI between 8.67 and 15.04. Leaf EOs exhibited an EC50 of 9.64 µg mL-1 and an SI of 15.04. Our study unveils the diverse chemical composition and multifaceted pharmacological properties of T. riparia, demonstrating its potential as a valuable source of bioactive compounds for therapeutic applications.
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In the Azores archipelago (Portugal), forest operations and wood industry generate large amounts of Cryptomeria japonica biomass residues (CJBR), which can be used to produce valuable essential oils (EOs). In this study, we evaluated the chemical composition and antioxidant activities of EOs from Azorean C. japonica sawdust (CJS) and resin-rich bark (CJRRB). The CJS and CJRRB EOs, obtained via hydrodistillation, showed different yield values (0.27% vs. 0.80% v/w, dry weight) and also different chemical profiles, as assessed using GC/MS. A total of 64 and 85 components were identified in CJS and CJRRB EOs, representing 95.7% and 96.9% of the total composition, respectively. The major components in CJS EO were oxygenated sesquiterpenes (mainly α+ß-eudesmol, 1-epicubenol, and cubebol), while in CJRRB EO, the major components were monoterpene hydrocarbons, including α-pinene, δ-3-carene, and limonene (66.6% vs. 6.4% for oxygenated sesquiterpenes and 0% vs. 64% for monoterpene hydrocarbons, respectively). Antioxidant activity was estimated using (i) two radical-based assays, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity, and (ii) a lipid model assay, ß-carotene-linoleic acid bleaching activity (BCBA). Both CJS and CJRRB EOs exhibited concentration-dependent antioxidant activities, and their DPPH, ABTS, and BCBA EC50 values were 1107 vs. 1275 µg/mL, 260 vs. 498 µg/mL, and 1764 vs. 662 µg/mL, respectively. The results indicate that both EOs were able to exert antioxidant activity via different mechanisms of action. Therefore, Azorean CJS and CJRRB may be sustainable sources for antioxidant compounds. This study expands the chemical and biological knowledge of CJBR EOs and, consequently, adds more value to the C. japonica EO industry.
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Five undescribed monoterpene-chalcone conjugates (1-5), one undescribed hypothetical precursor of diarylheptanoid (6), two undescribed diarylheptanoids (7-8), and fourteen known compounds (9-22) were isolated from the seeds of Alpinia katsumadai. Their structures were elucidated through the interpretation of HRESIMS, NMR, ECD, and X-ray diffraction data. MTT assays on human cancer cell lines (HepG2, A549, SGC7901, and SW480) revealed that compounds 3-8, 11, and 13 exhibited broad-spectrum antiproliferative activities with IC50 values ranging from 3.59 to 21.78 µM. B cell lymphoma 2 was predicted as the target of sumadain C (11) by network pharmacology and verified by homogeneous time-resolved fluorescence assay and molecular docking.
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Alpinia , Antineoplásicos Fitogénicos , Proliferación Celular , Diarilheptanoides , Ensayos de Selección de Medicamentos Antitumorales , Monoterpenos , Semillas , Alpinia/química , Humanos , Diarilheptanoides/química , Diarilheptanoides/farmacología , Diarilheptanoides/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Semillas/química , Estructura Molecular , Proliferación Celular/efectos de los fármacos , Monoterpenos/química , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacología , Relación Estructura-Actividad , Chalconas/química , Chalconas/farmacología , Chalconas/aislamiento & purificación , Chalcona/química , Chalcona/farmacología , Chalcona/aislamiento & purificación , Línea Celular Tumoral , Relación Dosis-Respuesta a Droga , Simulación del Acoplamiento MolecularRESUMEN
BACKGROUND: Monoterpenes are among the most important volatile aromatic compounds contributing to the flavor and aroma of grapes and wine. However, the molecular basis of monoterpene biosynthesis has not yet been fully elucidated. RESULTS: In our study, transcriptomics and gas chromatography-mass spectrometry (GC-MS) were used to mine candidate genes and transcription factors involved in monoterpene biosynthesis between high-monoterpene and zero-monoterpene table grape cultivars. We found that monoterpene biosynthesis was positively correlated by the expression of five genes encoding 1-deoxy-D-xylulose-5-phosphate synthase (VvDXSs), one encoding 4-hydroxy-3-methylbut-2-enyl diphosphate reductase (VvHDR), three hydroxy-3-methylglutaryl-CoA synthases (VvHMGSs) and one mevalonate kinase (VvMVK), whereas the expression of one isopentenyl diphosphate isomerase (VvIDI) and one 3-hydroxy-3-methylglutaryl-CoA reductase (VvHMGR) negatively correlated monoterpene biosynthesis. Of these genes, VvIDI was selected to validate its function in monoterpene accumulation through a transient overexpression experiment, and was shown to inhibit the biosynthesis of grape linalool and α-terpineol. Meanwhile, we found that a 64-amino acid extension sequence at the N-terminus can guide the VvIDI protein to target the chloroplast. CONCLUSIONS: The findings of this study should help to guide future functional analysis of key genes as well as mining the potential regulatory mechanism of monoterpene biosynthesis in grapes and grape products.
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Isomerasas de Doble Vínculo Carbono-Carbono , Monoterpenos , Vitis , Vitis/genética , Vitis/enzimología , Vitis/metabolismo , Monoterpenos/metabolismo , Isomerasas de Doble Vínculo Carbono-Carbono/metabolismo , Isomerasas de Doble Vínculo Carbono-Carbono/genética , Transcriptoma , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Regulación de la Expresión Génica de las Plantas , Cromatografía de Gases y Espectrometría de Masas , Odorantes , HemiterpenosRESUMEN
With climate warming and economic globalization, insect-microbe assemblages are becoming increasingly responsible for various devastating forest diseases worldwide. Japanese larch (Larix kaempferi) is extensively cultivated in China because of its high survival rate, rapid maturation and robust mechanical properties. Endoconidiophora fujiensis, an ophiostomatoid fungus associated with Ips subelongatus, has been identified as a lethal pathogen of L. kaempferi in Japan. However, there is a dearth of research on the pathogenicity of E. fujiensis in larches in China. Therefore, we investigated the pathogenicity of E. fujiensis in introduced L. kaempferi and indigenous larch (Larix olgensis) trees and compared the induced resistance responses to the pathogen in both tree species in terms of physiology and gene expression. Five-year-old saplings and 25-year-old adult trees of L. olgensis and L. kaempferi were inoculated in parallel during the same growing season. Endoconidiophora fujiensis exhibited high pathogenicity in both larch species, but particularly in L. kaempferi compared with L. olgensis adult trees; adult L. olgensis was more resistant to E. fujiensis than adult L. kaempferi, which was reflected in higher accumulation of defensive monoterpenes, such as myrcene, 3-carene and limonene and the earlier induction of defense genes catalase (CAT) and pathogenesis-related protein 1 (PR1). This study contributes to our understanding of the interactions between bark beetle-associated ophiostomatoid fungi and host larches, from phenotypic responses to alterations in secondary metabolites via defense- and metabolism-related gene activation, providing a valuable foundation for the management of larch diseases and pests in the future.
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Ascomicetos , Resistencia a la Enfermedad , Larix , Enfermedades de las Plantas , Larix/microbiología , Enfermedades de las Plantas/microbiología , Ascomicetos/fisiología , Ascomicetos/patogenicidad , China , VirulenciaRESUMEN
Four new monoterpene rhamnosides, graphiumisides A-D (1-4), along with four known steroid compounds (5-8) were isolated from the fermentation extract of animal-derived endophytic fungus, Graphium sp. GD-11. The chemical structures of all compounds were elucidated using 1D and 2D NMR, HRESIMS spectroscopic analyses, and other spectroscopic methods. Compounds 1-4 exhibit a distinctive structure connected by one p-menthane type monoterpene and one L-rhamnose. This is the first report of monoterpene glycosides from Graphium sp. All compounds (1-8) were tested for cytotoxic activities against four cancer cell lines (HepG2, SMMC7721, SW480, and A549), and only compound 1 showed weak anti-tumor activity against SMMC7721 cells.
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Antineoplásicos , Ensayos de Selección de Medicamentos Antitumorales , Glicósidos , Monoterpenos , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Humanos , Monoterpenos/química , Monoterpenos/farmacología , Monoterpenos/aislamiento & purificación , Línea Celular Tumoral , Animales , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Estructura Molecular , Conformación Molecular , Relación Estructura-ActividadRESUMEN
A highly effective enantioselective monobenzoylation of 1,3-diols has been developed for the synthesis of 1,1-disubstituted tetrahydro-ß-carbolines. The chemistry has been successfully applied to the asymmetric total synthesis of (+)-alstrostine G, which also features a cascade Heck/hemiamination reaction enabling facile construction of the pivotal pentacyclic core.
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BACKGROUND: (-)-Fenchone is a naturally occurring monoterpene found in the essential oils of Foeniculum vulgare Mill., Thuja occidentalis L., and Peumus boldus Molina. Pharmacological studies have reported its antinociceptive, antimicrobial, anti-inflammatory, antidiarrheal, and antioxidant activities. METHODS: The preventive antiulcer effects of (-)-Fenchone were assessed through oral pretreatment in cysteamine-induced duodenal lesion models. Gastric healing, the underlying mechanisms, and toxicity after repeated doses were evaluated using the acetic acid-induced gastric ulcer rat model with oral treatment administered for 14 days. RESULTS: In the cysteamine-induced duodenal ulcer model, fenchone (37.5-300 mg/kg) significantly decreased the ulcer area and prevented lesion formation. In the acetic acid-induced ulcer model, fenchone (150 mg/kg) reduced (p < 0.001) ulcerative injury. These effects were associated with increased levels of reduced glutathione (GSH), superoxide dismutase (SOD), interleukin (IL)-10, and transforming growth factor-beta (TGF-ß). Furthermore, treatment with (-)-Fenchone (150 mg/kg) significantly reduced (p < 0.001) malondialdehyde (MDA), myeloperoxidase (MPO), interleukin-1 beta (IL-1ß), tumor necrosis factor-alpha (TNF-α), and nuclear transcription factor kappa B (NF-κB). A 14-day oral toxicity investigation revealed no alterations in heart, liver, spleen, or kidney weight, nor in the biochemical and hematological parameters assessed. (-)-Fenchone protected animals from body weight loss while maintaining feed and water intake. CONCLUSION: (-)-Fenchone exhibits low toxicity, prevents duodenal ulcers, and enhances gastric healing activities. Antioxidant and immunomodulatory properties appear to be involved in its therapeutic effects.