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1.
Mol Nutr Food Res ; 68(8): e2300831, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38602198

RESUMO

SCOPE: The excretion of dietary odorants into urine and milk is evaluated and the impact of possible influencing factors determined. Furthermore, the metabolic relevance of conjugates for the excretion into milk is investigated. METHODS AND RESULTS: Lactating mothers (n = 20) are given a standardized curry dish and donated one milk and urine sample each before and 1, 2, 3, 4.5, 6, and 8 h after the intervention. The concentrations of nine target odorants in these samples are determined. A significant transition is observed for linalool into milk, as well as for linalool, cuminaldehyde, cinnamaldehyde, and eugenol into urine. Maximum concentrations are reached within 1 h after the intervention in the case of milk and within 2-3 h in the case of urine. In addition, the impact of glucuronidase treatment on odorant concentrations is evaluated in a sample subset of twelve mothers. Linalool, eugenol, and vanillin concentrations increased 3-77-fold in milk samples after treatment with ß-glucuronidase. CONCLUSION: The transfer profiles of odorants into milk and urine differ qualitatively, quantitatively, and in temporal aspects. More substances are transferred into urine and the transfer needs a longer period compared with milk. Phase II metabolites are transferred into urine and milk.


Assuntos
Acroleína/análogos & derivados , Monoterpenos Acíclicos , Benzaldeídos , Eugenol , Leite Humano , Odorantes , Humanos , Leite Humano/química , Feminino , Odorantes/análise , Eugenol/urina , Eugenol/metabolismo , Eugenol/análogos & derivados , Adulto , Benzaldeídos/urina , Monoterpenos Acíclicos/urina , Glucuronidase/metabolismo , Lactação , Acroleína/urina , Acroleína/metabolismo , Monoterpenos/urina
2.
J Chromatogr A ; 1722: 464896, 2024 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-38631224

RESUMO

In this study, a novel magnetic bead-based ligand fishing method was developed for rapid discovery of monoterpene indoles as monoamine oxidase A inhibitors from natural products. In order to improve the screening efficiency, two different magnetic beads, i.e. amine and carboxyl terminated magnetic beads, were comprehensively compared in terms of their ability to immobilize monoamine oxidase A (MAOA), biocatalytic activity and specific adsorption rates for affinity ligands. Carboxyl terminated magnetic beads performed better for MAOA immobilization and demonstrated superior performance in ligand fishing. The MAOA immobilized magnetic beads were applied to screen novel monoamine oxidase inhibitors in an alkaloid-rich plant, Hunteria zeylanica. Twelve MAOA affinity ligands were screened out, and ten of them were identified as monoterpene indole alkaloids by HPLC-Obitrap-MS/MS. Among them, six ligands, namely geissoschizol, vobasinol, yohimbol, dihydrocorynanthenol, eburnamine and (+)-isoeburnamine which exhibited inhibitory activity against MAOA with low IC50 values. To further explore their inhibitory mechanism, enzyme kinetic analysis and molecular docking studies were conducted.


Assuntos
Simulação de Acoplamento Molecular , Inibidores da Monoaminoxidase , Monoaminoxidase , Inibidores da Monoaminoxidase/química , Inibidores da Monoaminoxidase/farmacologia , Inibidores da Monoaminoxidase/isolamento & purificação , Monoaminoxidase/metabolismo , Monoaminoxidase/química , Ligantes , Indóis/química , Monoterpenos/química , Monoterpenos/isolamento & purificação , Cinética , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão/métodos , Enzimas Imobilizadas/química , Enzimas Imobilizadas/metabolismo , Enzimas Imobilizadas/antagonistas & inibidores , Humanos , Extratos Vegetais/química
3.
Zhongguo Zhong Yao Za Zhi ; 49(5): 1369-1377, 2024 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-38621985

RESUMO

A total of 11 active ingredients including psoralen, isopsoralen, bakuchiol, bavachalcone, bavachinin, corylin, coryfolin, isobavachalcone, neobavaisoflavone, bakuchalcone, and corylifol A from Psoraleae Fructus in the plasma samples of diabetic and normal rats were simultaneously determined by UHPLC-MS/MS. The pharmacokinetic parameters were calculated to elucidate the pharmacokinetic profiles of coumarins, flavonoids, and monoterpene phenols in normal and diabetic rats. The rat model of type 2 diabetes mellitus(T2DM) was induced by a high-sugar and high-fat diet combined with injection of 1% streptozotocin every two days. The plasma samples were collected at different time points after the rats were administrated with Psoraleae Fructus. The proteins in the plasma samples were precipitated by ethyl acetate, and the plasma concentrations of the 11 components of Psoraleae Fructus were determined by UHPLC-MS/MS. The pharmacokinetic parameters were calculated by DAS 3.0. The results showed that the pharmacokinetic beha-viors of 8 components including psoralen, isopsoralen, bakuchiol, and bavachinin from Psoraleae Fructus in both female and male mo-del rats were significantly different from those in normal rats. Among them, the coumarins including psoralen, isopsoralen, and corylin showed lowered levels in the blood of both female and male model rats. The flavonoids(bavachinin, corylifol A, and bakuchalcone) and the monoterpene phenol bakuchiol showed decreased levels in the female model rats but elevated levels in the male model rats. It is suggested that the dosage of Psoraleae Fructus should be reasonably adjusted for the patients of different genders at the time of clinical administration.


Assuntos
Diabetes Mellitus Experimental , Diabetes Mellitus Tipo 2 , Medicamentos de Ervas Chinesas , Furocumarinas , Fenóis , Psoralea , Humanos , Ratos , Feminino , Masculino , Animais , Medicamentos de Ervas Chinesas/farmacocinética , Espectrometria de Massas em Tandem/métodos , Diabetes Mellitus Experimental/tratamento farmacológico , Flavonoides/farmacologia , Ficusina , Cumarínicos , Monoterpenos
4.
Int J Mol Sci ; 25(7)2024 Mar 31.
Artigo em Inglês | MEDLINE | ID: mdl-38612715

RESUMO

Breast cancer (BC) represents one of the most prevalent malignant threats to women globally. Tumor relapse or metastasis is facilitated by BC stemness progression, contributing to tumorigenicity. Therefore, comprehending the characteristics of stemness progression and the underlying molecular mechanisms is pivotal for BC advancement. Hinokitiol (ß-thujaplicin), a tropolone-related compound abundant in the heartwood of cupressaceous plants, exhibits antimicrobial activity. In our study, we employed three BC cell lines (MDA-MB-231, MCF-7, and T47D) to assess the expression of stemness-, apoptosis-, and autophagy-related proteins. Hinokitiol significantly reduced the viability of cancer cells in a dose-dependent manner. Furthermore, we observed that hinokitiol enhances apoptosis by increasing the levels of cleaved poly-ADP-ribose polymerase (PARP) and phospho-p53. It also induces dysfunction in autophagy through the upregulation of LC3B and p62 protein expression. Additionally, hinokitiol significantly suppressed the number and diameter of cancer cell line spheres by reducing the expression of cluster of differentiation44 (CD44) and key transcription factors. These findings underscore hinokitiol's potential as a therapeutic agent for breast cancer, particularly as a stemness-progression inhibitor. Further research and clinical studies are warranted to explore the full therapeutic potential of hinokitiol in the treatment of breast cancer.


Assuntos
Neoplasias da Mama , Monoterpenos , Tropolona , Tropolona/análogos & derivados , Humanos , Feminino , Tropolona/farmacologia , Neoplasias da Mama/tratamento farmacológico , Recidiva Local de Neoplasia , Apoptose , Autofagia , Células MCF-7 , Receptores de Hialuronatos , Fatores de Transcrição SOXB1
5.
J Appl Microbiol ; 135(4)2024 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-38587823

RESUMO

AIM: In this study, it was aimed to examine the antibacterial activity of the essential oil components (EOCs), carvacrol (CAR), cinnamaldehyde (CIN), thymol (TH), alpha pinene (α-PN), eucalyptol (EU), limonene (LIM), and the antibiotics, linezolid (LZD), vancomycin (VAN), gentamicin (GEN), ciprofloxacin (CIP), clindamycin (CLN), and penicillin (PEN) against 50 multidrug resistant Corynebacterium striatum strains, and the synergistic interactions of CAR and CIN with the antibiotics against 10 randomly selected Coryne. striatum strains to explore synergistic interactions to determine if their combined use could enhance antibiotic activity and potentially reduce resistance. METHODS AND RESULTS: The activity of the EOCs and the antibiotics against Coryne. striatum strains isolated from clinical specimens, was examined by broth microdilution method. The synergistic interactions of the EOCs with the antibiotics against 10 randomly selected Coryne. striatum strains were determined by checkerboard method. EOCs, CIN, and CAR and antibiotics, LZD, VAN, GEN, CIP, and CLN were detected to have antibacterial activity against Coryne. striatum strains alone and either synergistic interactions were observed in combinations of the antibiotics with EOCs. CONCLUSIONS: All Coryne. striatum strains were determined to be susceptible to VAN and LZD and resistant to GEN, PEN, CIP, and CLN. Synergistic interactions were observed in all combinations of antibiotics tested with CAR and CIN.


Assuntos
Acroleína , Acroleína/análogos & derivados , Antibacterianos , Corynebacterium , Farmacorresistência Bacteriana Múltipla , Sinergismo Farmacológico , Testes de Sensibilidade Microbiana , Monoterpenos , Óleos Voláteis , Antibacterianos/farmacologia , Corynebacterium/efeitos dos fármacos , Óleos Voláteis/farmacologia , Farmacorresistência Bacteriana Múltipla/efeitos dos fármacos , Acroleína/farmacologia , Monoterpenos/farmacologia , Cimenos/farmacologia , Ciprofloxacina/farmacologia , Gentamicinas/farmacologia , Vancomicina/farmacologia , Linezolida/farmacologia , Limoneno/farmacologia , Eucaliptol/farmacologia , Timol/farmacologia , Clindamicina/farmacologia , Humanos , Penicilinas/farmacologia , Terpenos/farmacologia , Cicloexenos/farmacologia , Infecções por Corynebacterium/microbiologia
6.
PLoS One ; 19(4): e0299218, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38662654

RESUMO

To enhance the yield of the one-step synthesis of terpinyl acetate from α-pinene and acetic acid, this study evaluated α-hydroxycarboxylic acid (HCA)-boric acid composite catalysts based on orthogonal experimental design. The most important factor affecting the terpinyl acetate content in the product was the HCA content. The catalytic performance of the composite catalyst was related to the pKa1 of HCA. The tartaric acid-boric acid composite catalyst showed the highest catalytic activity. The α-pinene conversion reached 91.8%, and the terpinyl acetate selectivity reached 45.6%. When boric acid was replaced with B2O3, the HCA composite catalyst activity was enhanced, which reduced the use of HCA. When the lactic acid and B2O3 content accounted for 10% and 4% of the α-pinene mass content, respectively, the α-pinene conversion reached 93.2%, and the terpinyl acetate selectivity reached up to 47.1%. In addition, the presence of water was unfavorable to HCA-boric acid composite catalyst. However, a water content less than 1% of the α-pinene mass content improved the catalytic activity of HCA-B2O3. When the tartaric acid-B2O3 was used as catalyst, and the water content was 1% of the α-pinene mass content, the α-pinene conversion was 89.6%, and the terpinyl acetate selectivity was 47.5%.


Assuntos
Monoterpenos Bicíclicos , Ácidos Bóricos , Monoterpenos , Catálise , Monoterpenos Bicíclicos/química , Ácidos Bóricos/química , Monoterpenos/química , Tartaratos/química , Acetatos/química , Ácidos Carboxílicos/química , Terpenos/química , Terpenos/síntese química
7.
Sci Rep ; 14(1): 5752, 2024 03 08.
Artigo em Inglês | MEDLINE | ID: mdl-38459176

RESUMO

Herbal spices are widely consumed as food additives owing to their distinct aroma and taste as well as a myriad of economic and health value. The aroma profile of four major spices including bay leaf, black pepper, capsicum, and fennel was tested using HS-SPME/GC-MS and in response to the most widely used spices´ processing methods including autoclaving and γ-radiation at low and high doses. Additionally, the impact of processing on microbial contamination of spices was tested using total aerobic count. GC-MS analysis led to the identification of 22 volatiles in bay leaf, 34 in black pepper, 23 in capsicum, and 24 in fennel. All the identified volatiles belonged to oxides/phenols/ethers, esters, ketones, alcohols, sesquiterpene and monoterpene hydrocarbons. Oxides/phenol/ethers were detected at high levels in all tested spices at ca. 44, 28.2, 48.8, 61.1%, in bay leaves, black pepper, capsicum, and fennel, respectively of the total blend and signifying their typical use as spices. Total oxides/phenol/ethers showed an increase in bay leaf upon exposure to γ-radiation from 44 to 47.5%, while monoterpene hydrocarbons were enriched in black pepper upon autoclaving from 11.4 in control to reach 65.9 and 82.6% for high dose and low dose of autoclaving, respectively. Cineole was detected in bay leaf at 17.9% and upon exposure to autoclaving at high dose and γ-radiation (both doses) its level increased by 29-31%. Both autoclaving and γ-radiation distinctly affected aroma profiles in examined spices. Further, volatile variations in response to processing were assessed using multivariate data analysis (MVA) revealing distinct separation between autoclaved and γ-radiated samples compared to control. Both autoclaving at 115 °C for 15 min and radiation at 10 kGy eliminated detected bioburden in all tested spices i.e., reduced the microbial counts below the detection limit (< 10 cfu/g).


Assuntos
Foeniculum , Piper nigrum , Compostos Orgânicos Voláteis , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Fenol/análise , Microextração em Fase Sólida/métodos , Quimiometria , Especiarias , Monoterpenos/análise , Éteres , Óxidos , Compostos Orgânicos Voláteis/análise
8.
Braz J Biol ; 83: e277354, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38452187

RESUMO

This study aimed to explore the diuretic activity of linalyl acetate (LA). LA is an essential oil, it is an integral phyto-constituent of various plants. In this study, acute and chronic diuretic activities were explored by measuring the levels of different electrolytes and pH in the urine of experimental rats. Rats were divided into five groups. The control group was given 10 mg/kg normal saline, the treated group was given 10 mg/kg furosemide, and the remaining 3 groups received different doses of LA including 25, 50, and 75 mg/kg through intraperitoneal route, to determine its diuretic potential. Urine volume for acute diuretic activity was measured for 6 hours however for chronic diuretic activity was measured for 6 days. For a comparative study of LA with a control group and treated group with reference drug, diuretic index was used. Moreover, the underlying mechanism of the diuretic activity was also explored by comparing atropine, L-NAME, and indomethacin. The results of each group with 6 rats in each group were obtained by ± standard error of the mean of every group. Analysis of Variance (ANOVA) was used for statistical analysis. Results revealed that the LA 75 mg/kg dose showed comparable results as of furosemide. Moreover, this study revealed the involvement of muscarinic receptors to produce diuresis in comparison with atropine with very little involvement of prostanoids and no effect on NO pathway induced by indomethacin and L-NAME respectively. It is concluded that LA possess anti-diuretic potential. Muscarinic receptors might be involved in producing diuretic effects.


Assuntos
Diuréticos , Furosemida , Monoterpenos , Ratos , Animais , Furosemida/farmacologia , NG-Nitroarginina Metil Éster/farmacologia , Diuréticos/farmacologia , Indometacina/farmacologia , Atropina/farmacologia , Extratos Vegetais/farmacologia , Receptores Muscarínicos
9.
Food Res Int ; 181: 114120, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38448101

RESUMO

Monoterpenes are typical aroma components in muscat grapes and wines, closely related to its geographical origins. However, the mechanism underlying the geographical differences of monoterpenes remains to be elucidated, especially in the Chinese viticulture regions. This study investigated the diversity of six Chinese viticultural vineyards (YT, XF, SS, XX, WW and CL) in the monoterpene composition of Vitis vinifera L. cv.'Muscat Hamburg' grapes and the resulted wines. Monoterpenes were analyzed by HS-SPME- GC-MS. The total amount of free and bound monoterpenes varied dramatically between grapes of different vineyards, and their contents were obviously higher in YT region grapes. The OAVs for 18 monoterpenes of grapes from the YT vineyard were relative higher than those of other regions, and the floral odor could distinguish grapes from different regions. The total free monoterpenes were highest in the YT region wine. Concentrations of total bound monoterpenes ranged from 711.13 µg/L (XF region) to 1078.30 µg/L (CL region). A correlation analysis showed that all monoterpenes showeda positive correlation with mean relative humidity, sum rainfall, and a negative correlation with sum duration of sunshine and mean temperature. This study would provide some new insights to understand the geographical differences of monoterpenes, and the results would facilitate the effective viticultural treatment of grapes to improve the quality of the aroma.


Assuntos
Vitis , Vinho , Cromatografia Gasosa-Espectrometria de Massas , Microextração em Fase Sólida , Monoterpenos
10.
J Nat Prod ; 87(4): 861-868, 2024 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-38438305

RESUMO

PC-A (1), a bromo nor-eremophilane, showed selective antiproliferative activity against a triple-negative breast cancer (TNBC) cell line. This unique activity prompted us to establish a total synthesis to facilitate a structure-activity relationship (SAR) study and selectivity optimization. An enantioselective first total synthesis of 1 was achieved starting from (R)-carvone through a side chain extension with a Mukaiyama aldol reaction and decalin construction. The synthesized decalin derivatives and debromo PC-A (2) were evaluated for antiproliferative activity against five human tumor cell lines, including TNBC, to assess preliminary SAR correlations.


Assuntos
Ensaios de Seleção de Medicamentos Antitumorais , Neoplasias de Mama Triplo Negativas , Humanos , Relação Estrutura-Atividade , Estrutura Molecular , Neoplasias de Mama Triplo Negativas/tratamento farmacológico , Estereoisomerismo , Antineoplásicos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Monoterpenos Cicloexânicos/farmacologia , Monoterpenos Cicloexânicos/química , Monoterpenos/farmacologia , Monoterpenos/química , Monoterpenos/síntese química , Sesquiterpenos/farmacologia , Sesquiterpenos/síntese química , Sesquiterpenos/química , Feminino , Linhagem Celular Tumoral , Sesquiterpenos Policíclicos/farmacologia , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/síntese química
11.
Sci Rep ; 14(1): 5439, 2024 03 05.
Artigo em Inglês | MEDLINE | ID: mdl-38443469

RESUMO

The objective of this study was to determine whether adding phytoncide oil (PO) and soybean oil (SBO) to the dairy cow diet could increase milk conjugated linoleic acid (CLA) and depress methane (CH4) emissions in Holstein dairy cows. Rumen fermentation was conducted at four levels of SBO (0, 1, 2, and 4%, on DM basis) and two levels of PO (0 and 0.1%, on DM basis) with in vitro experiment. To evaluate blood parameters, fecal microbe population, milk yield and fatty acid compositions, and CH4 production, in vivo experiment was conducted using 38 Holstein dairy cows divided into two groups of control (fed TMR) and treatment (fed TMR with 0.1% PO and 2% SBO as DM basis). In the in vitro study (Experiment 1), PO or SBO did not affect rumen pH. However, SBO tended to decrease ruminal ammonia-N (p = 0.099). Additionally, PO or SBO significantly decreased total gas production (p = 0.041 and p = 0.034, respectively). Both PO and SBO significantly decreased CH4 production (p < 0.05). In addition, PO significantly increased both CLA isomers (c9, t11 and t10, c12 CLA) (p < 0.001). Collectively, 0.1% PO and 2% SBO were selected resulting in most effectively improved CLA and decreased CH4 production. In the in vivo study (Experiment 2), 0.1% PO with 2% SBO (PSO) did not affect complete blood count. However, it decreased blood urea nitrogen and magnesium levels in blood (p = 0.021 and p = 0.01, respectively). PSO treatment decreased pathogenic microbes (p < 0.05). It increased milk yield (p = 0.017) but decreased percentage of milk fat (p = 0.013) and MUN level (p < 0.01). In addition, PSO treatment increased both the concentration of CLA and PUFA in milk fat (p < 0.01). Finally, it decreased CH4 emissions from dairy cows. These results provide compelling evidence that a diet supplemented with PSO can simultaneously increase CLA concentration and decrease CH4 production with no influence on the amount of milk fat (kg/day) in Holstein dairy cows.


Assuntos
Ácidos Linoleicos Conjugados , Leite , Monoterpenos , Animais , Feminino , Bovinos , Ácidos Linoleicos Conjugados/farmacologia , Óleo de Soja , Suplementos Nutricionais , Metano
12.
Planta ; 259(5): 105, 2024 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-38551685

RESUMO

MAIN CONCLUSION: Monoterpenes and phenolics play distinct roles in defending white spruce trees from insect defoliators. Monoterpenes contribute to the toxicity of the foliage, deterring herbivory, whereas phenolics impede budworm growth. This study demonstrates the complex interplay between monoterpenes and phenolics and their collective influence on the defense strategy of white spruce trees against a common insect defoliator. Long-lived coniferous trees display considerable variations in their defensive chemistry. The impact of these defense phenotype variations on insect herbivores of the same species remains to be thoroughly studied, mainly due to challenges in replicating the comprehensive defense profiles of trees under controlled conditions. This study methodically examined the defensive properties of foliar monoterpenes and phenolics across 80 distinct white spruce families. These families were subsequently grouped into two chemotypes based on their foliar monoterpene concentrations. To understand the separate and combined effects of these classes on tree defenses to the eastern spruce budworm, we conducted feeding experiments using actual defense profiles from representative families. Specifically, we assessed budworm response when exposed to substrates amended with phenolics alone or monoterpenes. Our findings indicate that the ratios and amounts of monoterpenes and phenolics present in the white spruce foliage influence the survival of spruce budworms. Phenotypes associated with complete larval mortality exhibited elevated ratios (ranging from 0.4 to 0.6) and concentrations (ranging from 1143 to 1796 ng mg-1) of monoterpenes. Conversely, families characterized by higher phenolic ratios (ranging from 0.62 to 0.77) and lower monoterpene concentrations (ranging from 419 to 985 ng mg-1) were less lethal to the spruce budworm. Both classes of defense compounds contribute significantly to the overall defensive capabilities of white spruce trees. Monoterpenes appear critical in determining the general toxicity of foliage, while phenolics play a role in slowing budworm development, thereby underscoring their collective importance in white spruce defenses.


Assuntos
Mariposas , Picea , Animais , Picea/genética , Mariposas/fisiologia , Larva/fisiologia , Monoterpenos , Árvores , Fenóis
13.
Metallomics ; 16(4)2024 04 05.
Artigo em Inglês | MEDLINE | ID: mdl-38449344

RESUMO

Iron is a vital metal for most biological functions in tissues, and its concentration is exquisitely regulated at the cellular level. During the process of differentiation, keratinocytes in the epidermis undergo a noticeable reduction in iron content. Conversely, psoriatic lesions, characterized by disruptions in epidermal differentiation, frequently reveal an excessive accumulation of iron within keratinocytes that have undergone differentiation. In this study, we clarified the significance of attenuated cellular iron content in the intricate course of epidermal differentiation. We illustrated this phenomenon through the utilization of hinokitiol, an iron chelator derived from the heartwood of Taiwanese hinoki, which forcibly delivers iron into cells independent of the intrinsic iron-regulation systems. While primary cultured keratinocytes readily succumbed to necrotic cell death by this iron chelator, mild administration of the hinokitiol-iron complex modestly disrupts the process of differentiation in these cells. Notably, keratinocyte model cells HaCaT and anaplastic skin rudiments exhibit remarkable resilience against the cytotoxic impact of hinokitiol, and the potent artificial influx of iron explains a suppressive effect selectively on epidermal differentiation. Moreover, the augmentation of iron content induced by the overexpression of divalent metal transporter 1 culminates in the inhibition of differentiation in HaCaT cells. Consequently, the diminution in cellular iron content emerges as an important determinant influencing the trajectory of keratinocyte differentiation.


Assuntos
Ferro , Queratinócitos , Tropolona/análogos & derivados , Ferro/metabolismo , Queratinócitos/metabolismo , Monoterpenos/metabolismo , Epiderme/fisiologia , Diferenciação Celular/fisiologia , Quelantes de Ferro/metabolismo
14.
Int J Biol Macromol ; 264(Pt 2): 130763, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38467223

RESUMO

Lindera glauca with rich resource and fruit terpene has emerged as potential material for utilization in China, but different germplasms show a variation for essential oil content and volatile profiling. This work aimed to determine key regulators (enzymes or transporters) and unravel mechanism of governing high production of essential oil of L. glauca fruit (EO-LGF). Temporal analysis of fruit growth and EO-LGF accumulation (yield, volatile compounds and contents) during development revealed a notable change in the contents of EO-LGF and its 45 compounds in developing fruits, and the major groups were monoterpene and sesquiterpene, showing good antioxidant and antimicrobial activities. To highlight molecular mechanism that govern such difference in terpene content and compound in developing fruits, Genome-wide assay was used to annotate 104 genes for terpene-synthesis pathway based on recent transcriptome data, and the comparative associations of terpene accumulative amount with gene transcriptional level were conducted on developing fruits to identify some crucial determinants (enzymes and transporters) with metabolic regulation model for high-quality terpene accumulation, involving in carbon allocation (sucrose cleavage, glycolysis and OPP pathway), metabolite transport, isoprene precursor production, C5-unit formation (MEP and MVA pathways), and mono-/sesqui-terpene synthesis. Our findings may present strategy for engineering terpene accumulation for utilization.


Assuntos
Lindera , Óleos Voláteis , Terpenos/metabolismo , Frutas , Lindera/genética , Lindera/metabolismo , Óleos Voláteis/metabolismo , Monoterpenos/metabolismo
15.
J Asian Nat Prod Res ; 26(1): 120-129, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38509697

RESUMO

Three new monoterpene phenol dimers, bisbakuchiols V-X (1-3), and two bakuchiol ethers (4 and 5), along with four known compounds (6-9) were isolated from the fruits of Psoralea corylifolia. Their structures were elucidated based on extensive spectral analysis. The absolute configurations of 1, 2, 4, and 5 were specified by quantum chemical calculations of ECD spectra.


Assuntos
Fenol , Psoralea , Fenol/análise , Frutas/química , Psoralea/química , Monoterpenos , Estrutura Molecular , Fenóis/química
16.
Sci Rep ; 14(1): 7342, 2024 03 28.
Artigo em Inglês | MEDLINE | ID: mdl-38538682

RESUMO

The present work aimed to investigate the effect of salinity in natural habitats in Egypt on the main secondary metabolites of Rosmarinus officinalis L. and Artemisia monosperma L. plants compared to plants grown at normal conditions. Plants grown under salinity were collected from Egyptian Western Coastal region habitats irrigated with underground water. Results showed that salinity increased the essential oil percentage of R. officinalis L. by 52.7% and A. monosperma L by 0.29% in addition to the total phenolics and flavonoids content in dry leaves compared to control plants. GC/MS analysis of rosemary essential oils revealed that salinity decreased the amount of some major oil monoterpenes component as verbenone, with a slight effect on 1,8 cineole and increased Camphor, endo- Boreneol, and linalool in addition to the appearance of new specific components such as Chrysanthenone monoterpene ketone and Caryophyllene sesquiterpene, while, in the case of Artemisia, the GC/MS showed that Artemisia ketone, Camphor, ß -phellandrene monoterpenes andα-Bisabolol sesquiterpenewere the major oil components; salinity decreased Camphor and ß -phellandrene content and increased artemisia ketone and α-Bisabolol oil content. About 11 new oil constituents were detected such as ( +)-2-Bornanone and Sesquisabinene hydrate. Mineral ions (N, K+, Ca+2, P, and Mg+2) uptake by R. officinalis and A. monosperma decreased in plants grown under salinity, while Na content increased compared to corresponding controls. Results demonstrated that both plants could tolerate the high salinity level in natural Western Coastal region soil which promoted more production of valuable secondary metabolites. The antimicrobial effect of R. officinalis L. and A. monosperma L. leaf methanolic extracts, results showed that R. officinalis extracts had an inhibitory response against all tested gram-positive and negative bacteria, in addition to the yeast (Candida albicans), whereas there was no any inhibitory effect concerning A. monosperma L extract on the tested species.


Assuntos
Anti-Infecciosos , Artemisia , Monoterpenos Cicloexânicos , Sesquiterpenos Monocíclicos , Óleos Voláteis , Rosmarinus , Cânfora/farmacologia , Egito , Óleos Voláteis/farmacologia , Monoterpenos/farmacologia , Folhas de Planta
17.
Genes (Basel) ; 15(3)2024 Feb 24.
Artigo em Inglês | MEDLINE | ID: mdl-38540346

RESUMO

Blumea balsamifera (L.) DC., an important economic and medicinal herb, has a long history of being used as a traditional Chinese medicine. Its leaves have always been used as a raw material for the extraction of essential oils, comprising large amounts of terpenoids, which have good therapeutic effects on many diseases, such as eczema, bacterial infection, and hypertension. However, the genetic basis of terpenoid biosynthesis in this plant is virtually unknown on account of the lack of genomic data. Here, a combination of next-generation sequencing (NGS) and full-length transcriptome sequencing was applied to identify genes involved in terpenoid biosynthesis at five developmental stages. Then, the main components of essential oils in B. balsamifera were identified using GC-MS. Overall, 16 monoterpenoids and 20 sesquiterpenoids were identified and 333,860 CCS reads were generated, yielding 65,045 non-redundant transcripts. Among these highly accurate transcripts, 59,958 (92.18%) transcripts were successfully annotated using NR, eggNOG, Swissprot, KEGG, KOG, COG, Pfam, and GO databases. Finally, a total of 56 differently expressed genes (DEGs) involved in terpenoid biosynthesis were identified, including 38 terpenoid backbone genes and 18 TPSs, which provide a significant amount of genetic information for B. balsamifera. These results build a basis for resource protection, molecular breeding, and the metabolic engineering of this plant.


Assuntos
Óleos Voláteis , Transcriptoma , Transcriptoma/genética , Terpenos/metabolismo , Monoterpenos , RNA-Seq
18.
Genes (Basel) ; 15(3)2024 Mar 02.
Artigo em Inglês | MEDLINE | ID: mdl-38540383

RESUMO

Many monoterpenoid indole alkaloids (MIAs) produced in Catharanthus roseus have demonstrated biological activities and clinical potential. However, their complex biosynthesis pathway in plants leads to low accumulation, limiting therapeutic applications. Efforts to elucidate the MIA biosynthetic regulatory mechanism have focused on improving accumulation levels. Previous studies revealed that jasmonic acid (JA), an important plant hormone, effectively promotes MIA accumulation by inducing the expression of MIA biosynthesis and transport genes. Nevertheless, excessive JA signaling can strongly inhibit plant growth, decreasing MIA productivity in C. roseus. Therefore, identifying key components balancing growth and MIA production in the JA signaling pathway is imperative for effective pharmaceutical production. Here, we identify a homolog of the jasmonate transporter 1, CrJAT1, through co-expression and phylogenetic analyses. Further investigation demonstrated that CrJAT1 can activate JA signaling to promote MIA accumulation without compromising growth. The potential role of CrJAT1 in redistributing intra/inter-cellular JA and JA-Ile may calibrate signaling to avoid inhibition, representing a promising molecular breeding target in C. roseus to optimize the balance between growth and specialized metabolism for improved MIA production.


Assuntos
Catharanthus , Ciclopentanos , Oxilipinas , Alcaloides de Triptamina e Secologanina , Monoterpenos/metabolismo , Catharanthus/genética , Catharanthus/metabolismo , Filogenia , Melhoramento Vegetal , Alcaloides de Triptamina e Secologanina/metabolismo , Transdução de Sinais
19.
Biomolecules ; 14(3)2024 Mar 14.
Artigo em Inglês | MEDLINE | ID: mdl-38540771

RESUMO

ß-cyclodextrin (ß-CD) is a good host for the encapsulation of fennel and basil essential oils (FEO and BEO, respectively) and the formation of inclusion complexes (ICs) using the co-precipitation method. According to the results of the GC/MS analysis conducted in this study, monoterpenes and monoterpenoids were the dominant chemical groups in total FEO, while in BEO, these two groups occurred along with sesquiterpenes and sesquiterpenoids. The presence of dominant compounds from both EOs was validated using the FT-IR spectra of ICs, which indicated successful complexation. Analyses conducted using SPME/GC-MS showed the continuous emission of volatiles over 24 h from both ICs. Under SEM, particles of both ICs appeared to have a rectangular or rhomboid morphology and few aggregates. The insecticidal properties of EOs and ICs with ß-CD were tested on the Colorado potato beetle (CPB) as a model pest. The inclusion complex of ß-CD with FEO altered the developmental dynamic and body mass of the CPB. The initial increase in the proteolytic activity of CPB larvae fed with potato plants sprayed with ICs was not maintained for long, and the proteolytic efficacy of treated larvae remained in line with that of the control larvae. Future investigations will focus on manipulating the volume of EOs used and the treatment duration for optimal efficacy and potential application.


Assuntos
Foeniculum , Ocimum basilicum , Óleos Voláteis , Sesquiterpenos , beta-Ciclodextrinas , Óleos Voláteis/química , Ocimum basilicum/química , Agentes de Controle Biológico , Espectroscopia de Infravermelho com Transformada de Fourier , beta-Ciclodextrinas/química , Monoterpenos , Sesquiterpenos/farmacologia
20.
Molecules ; 29(6)2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38543021

RESUMO

As part of our interest in the volatile phytoconstituents of aromatic plants of the Great Basin, we have obtained essential oils of Ambrosia acanthicarpa (three samples), Artemisia ludoviciana (12 samples), and Gutierrezia sarothrae (six samples) from the Owyhee Mountains of southwestern Idaho. Gas chromatographic analyses (GC-MS, GC-FID, and chiral GC-MS) were carried out on each essential oil sample. The essential oils of A. acanthicarpa were dominated by monoterpene hydrocarbons, including α-pinene (36.7-45.1%), myrcene (21.6-25.5%), and ß-phellandrene (4.9-7.0%). Monoterpene hydrocarbons also dominated the essential oils of G. sarothrae, with ß-pinene (0.5-18.4%), α-phellandrene (2.2-11.8%), limonene (1.4-25.4%), and (Z)-ß-ocimene (18.8-39.4%) as major components. The essential oils of A. ludoviciana showed wide variation in composition, but the relatively abundant compounds were camphor (0.1-61.9%, average 14.1%), 1,8-cineole (0.1-50.8%, average 11.1%), (E)-nerolidol (0.0-41.0%, average 6.8%), and artemisia ketone (0.0-46.1%, average 5.1%). This is the first report on the essential oil composition of A. acanthicarpa and the first report on the enantiomeric distribution in an Ambrosia species. The essential oil compositions of A. ludoviciana and G. sarothrae showed wide variation in composition in this study and compared with previous studies, likely due to subspecies variation.


Assuntos
Artemisia , Óleos Voláteis , Óleos Voláteis/química , Artemisia/química , Ambrosia , Idaho , Monoterpenos/análise
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