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1.
Plant Dis ; 2024 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-38173261

RESUMO

Cinnamomum camphora, known as the camphor tree, is an evergreen tree widely cultivated in Asia as an ornamental plant (Singh and Jawaid, 2012). In June 2023, several leaves on a total of 10 trees planted on a street in Suncheon, Jeonnam Province, Korea showed black spots. Disease incidence was observed in at least 15% of the 10 trees. The symptoms included circular spots with a light ash-colored center and dark brown borders. The size of lesions varied depending on the progress of the disease. The disease progressed by 30% on the tree leaves. To isolate the pathogen, we cut out the lesions on the leaf surface sterilized with 70% ethanol for one minute, washed three times with sterilized distilled water, dried, and placed on water agar. Then, it was incubated at 25°C for three days. Emerging hyphae from the samples were subcultured on potato dextrose agar (PDA), resulting in three independent isolates (SYP-F1226-1 to SYP-F1226-3) after single spore isolation from 3 independent trees. The isolates exhibited grayish fluffy mycelium in the center of the colony, while the edges were white on PDA. Conidia had rounded cylindrical shape and were 4.9 to 8.4 µm  1.4 to 3.1 µm (avg. 5.9  2.1 µm, n = 100) in size. Appressoria were round, dark gray, produced at the tip of the germ tube after a septum formed the conidium. The morphological characteristics matched those of Colletotrichum species complexes. (Damm et al., 2012; Weir et al., 2012). For molecular identification, ITS (OR647338 to 40), GAPDH (OR657042 to 44), CHS-1 (OR657045 to 47), ACT (OR657048 to 50), and CAL (OR657051 to 53) sequences from isolates SYP-F1226-1~3 showed a 99.65%, 98.56%, 99.00%, 99.28%, and 99.52% identity with that of type strain C. gloeosporioides ICMP 17821 (JX010152, JX010056, JX009818, JX009531, and JX010445, respectively). Using the MEGA X program (Kumar et al. 2018), maximum likelihood analysis based on the concatenated sequences placed the isolates within a clade comprising C. gloeosporioides. Pathogenicity of SYP-F1226-1 was tested using three leaves from a 1-year-old branch of three independent healthy C. camphora plants. The leaf surfaces were sterilized by rubbing a cotton pad soaked in 70% ethanol and then wiping them with a sterilized cotton pad. The leaves per plant were inoculated with 5 mL of a conidial suspension (1 × 105 conidia/mL), both with and without wounding. Another three control leaves were inoculated with sterile distilled water, both with and without wounding. The inoculated leaves were wrapped in a plastic bag for 48 hours under conditions of 100% relative humidity. Spot symptoms were observed on both wounded and non-wounded leaves 21 days after inoculation. No symptoms were observed in the control on either of the wounded leaves. Pathogenicity tests were performed three times. The pathogen was re-isolated from the lesion after treatment, and its identity was confirmed using the five genes and morphological characteristics. This confirms the fulfillment of Koch's postulates. C. fioriniae (Liu et al, 2022) and C. siamens (Liu et al, 2022; Khoo et al, 2023) have been reported as the causal pathogen of anthracnose in C. camphora, but C. gloeosporioides has not been reported as a pathogen in C. camphora. To our knowledge, this is the first report of anthracnose caused by C. gloeosporioides on C. camphora in Korea. This study will provide symptomatic, mycological, and molecular biological information for the early detection of anthracnose disease in C. camphora plants.

2.
Molecules ; 29(4)2024 Feb 09.
Artigo em Inglês | MEDLINE | ID: mdl-38398563

RESUMO

We synthesized six new camphor-derived homochiral thioureas 1-6, from commercially available (1R)-(-)-camphorquinone. These new compounds 1-6 were evaluated as asymmetric organocatalysts in the stereoselective formation of glycosidic bonds, with 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl and 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates as donors, and several alcohols as glycosyl acceptors, such as methanol, ethanol, 1-propanol, 1-butanol, 1-octanol, iso-propanol, tert-butanol, cyclohexanol, phenol, 1-naphtol, and 2-naphtol. Optimization of the asymmetric glycosylation reaction was achieved by modifying reaction conditions such as solvent, additive, loading of catalyst, temperature, and time of reaction. The best result was obtained with 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates, using 15 mol% of organocatalyst 1, in the presence of 2 equiv of MeOH in solvent-free conditions at room temperature for 1.5 h, affording the glycosidic compound in a 99% yield and 1:73 α:ß stereoselectivity; under the same reaction conditions, without using a catalyst, the obtained stereoselectivity was 1:35 α:ß. Computational calculations prior to the formation of the products were modeled, using density functional theory, M06-2X/6-31G(d,p) and M06-2X/6-311++G(2d,2p) methods. We observed that the preference for ß glycoside formation, through a stereoselective inverted substitution, relies on steric effects and the formation of hydrogen bonds between thiourea 1 and methanol in the complex formed.

3.
Angew Chem Int Ed Engl ; 63(22): e202403321, 2024 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-38482551

RESUMO

Rational design of unnatural amino acid building blocks capable of stabilizing predictable secondary structures similar to protein fragments is pivotal for foldamer chemistry/catalysis. Here, we introduce novel ß-amino acid building blocks: [1S,2R,4R]exoCDA and [1S,2S,4R]endoCDA, derived from the abundantly available R(+)-camphor, which is traditionally known for its medicinal value. Further, we demonstrate that the homooligomers of exoCDA adopt 6-strand conformation, which switches to a robust 10/12-helix simply by inserting flexible ß-hGly spacer at alternate positions (1 : 1 ß-hGly/exoCDA heterooligomers), as evident by DFT-calculations, solution-state NMR spectroscopy and X-ray crystallography. To the best of our knowledge, this is the first example of crystalline-state structure of left-handed 10/12-mixed helix, that is free from the conventional approach of employing ß-amino acids of either alternate chirality or alternate ß2/ß3 substitutions, to access the 10/12-helix. The results also show that the homooligomers of heterochiral exoCDA don't adopt helical fold, instead exhibit banana-shaped strands, whereas the homodimers of the other diastereomer endoCDA, nucleate 8-membered turns. Furthermore, the homo-exoCDA and hetero-[ß-hGly-exoCDA] oligomers are found to exhibit self-association properties with distinct morphological features. Overall, the results offer new possibilties of constructing discrete stable secondary and tertiary structures based on CDAs, which can accommodate flexible residues with desired side-chain substitutions.


Assuntos
Aminoácidos , Cânfora , Cristalografia por Raios X , Aminoácidos/química , Cânfora/química , Modelos Moleculares , Espectroscopia de Ressonância Magnética
4.
BMC Genomics ; 24(1): 34, 2023 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-36658477

RESUMO

BACKGROUND: Pagiophloeus tsushimanus (Coleoptera: Curculionidae), an emerging forest pest exclusively infesting camphor trees, has recently caused severe ecological and economic damage in localized areas in China. Its population outbreak depends largely on the capacity to overcome the pressure of terpenoid-derived metabolites (e.g. linalool) from camphor trees. At present, the molecular basis of physiological adaptation of P. tsushimanus to dietary linalool is poorly understood, and there is no available reference genome or transcriptome. RESULTS: Herein, we constructed the transcriptome profiling of P. tsushimanus larvae reared on linalool-infused diets using RNA sequencing and single-molecule real-time sequencing. A total of 20,325 high-quality full-length transcripts were identified as a reference transcriptome, of which 14,492 protein-coding transcripts including 130 transcription factors (TFs), and 5561 long non-coding RNAs (lncRNAs) were detected. Also, 30 alternative splicing events and 8049 simple sequence repeats were captured. Gene ontology enrichment of differential expressed transcripts revealed that overall up-regulation of both cytochrome P450s (CYP450s) and cuticular proteins (CPs), was the primary response characteristic against dietary linalool. Other physiological effects possibly caused by linalool exposure, such as increase in Reactive Oxygen Species (ROS) and hormetic stimulation, were compensated by a handful of induced genes encoding antioxidases, heat shock proteins (HSPs), juvenile hormone (JH) epoxide hydrolases, and digestive enzymes. Additionally, based on co-expression networks analysis, a diverse array of hub lncRNAs and TFs co-expressed with CYP450s and CPs were screened as the potential gene regulators. Temporal expression of candidate transcripts determined by quantitative real-time PCR also indicated a cooperative relationship between the inductions of CYP450s and CPs upon exposure to linalool. CONCLUSIONS: Our present study provides an important transcriptome resource of P. tsushimanus, and lays a valuable foundation for understanding how this specialist pest copes with chemical challenges in its specific host environments.


Assuntos
Besouros , RNA Longo não Codificante , Gorgulhos , Animais , RNA-Seq , Besouros/genética , Gorgulhos/genética , Larva/genética , RNA Longo não Codificante/genética , Perfilação da Expressão Gênica , Transcriptoma , Sistema Enzimático do Citocromo P-450/genética , Dieta
5.
Planta ; 258(4): 69, 2023 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-37608037

RESUMO

MAIN CONCLUSION: Genome-wide screening of short-chain dehydrogenases/reductases (SDR) family reveals functional diversification of borneol dehydrogenase (BDH) in Wurfbainia villosa. Wurfbainia villosa is an important medicinal plant, the fruits of which accumulate abundant terpenoids, especially bornane-type including borneol and camphor. The borneol dehydrogenase (BDH) responsible for the conversion of borneol to camphor in W. villosa remains unknown. BDH is one member of short-chain dehydrogenases/reductases (SDR) family. Here, a total of 115 classical WvSDR genes were identified through genome-wide screening. These WvSDRs were unevenly distributed on different chromosomes. Seven candidate WvBDHs based on phylogenetic analysis and expression levels were selected for cloning. Of them, four BDHs can catalyze different configurations of borneol and other monoterpene alcohol substrates to generate the corresponding oxidized products. WvBDH1 and WvBDH2, preferred (+)-borneol to (-)-borneol, producing the predominant ( +)-camphor. WvBDH3 yielded approximate equivalent amount of (+)-camphor and (-)-camphor, in contrast, WvBDH4 generated exclusively (+)-camphor. The metabolic profiles of the seeds showed that the borneol and camphor present were in the dextrorotatory configuration. Enzyme kinetics and expression pattern in different tissues suggested WvBDH2 might be involved in the biosynthesis of camphor in W. villosa. All results will increase the understanding of functional diversity of BDHs.


Assuntos
Oxirredutases do Álcool , Cânfora , Filogenia
6.
Respir Res ; 24(1): 45, 2023 Feb 08.
Artigo em Inglês | MEDLINE | ID: mdl-36755306

RESUMO

BACKGROUND: Upper respiratory tract infections (URTIs) impact all age groups and have a significant economic and social burden on society, worldwide. Most URTIs are mild and self-limiting, but due to the wide range of possible causative agents, including Rhinovirus (hRV), Adenovirus, Respiratory Syncytial Virus (RSV), Coronavirus and Influenza, there is no single and effective treatment. Over-the-counter (OTC) remedies, including traditional medicines and those containing plant derived substances, help to alleviate symptoms including inflammation, pain, fever and cough. PURPOSE: This systematic review focuses on the role of the major plant derived substances in several OTC remedies used to treat cold symptoms, with a particular focus on the transient receptor potential (TRP) channels involved in pain and cough. METHODS: Literature searches were done using Pubmed and Web of Science, with no date limitations, using the principles of the PRISMA statement. The search terms used were 'TRP channel AND plant compound', 'cough AND plant compound', 'cough AND TRP channels AND plant compound', 'cough AND P2X3 AND plant compound' and 'P2X3 AND plant compound' where plant compound represents menthol or camphor or eucalyptus or turpentine or thymol. RESULTS: The literature reviewed showed that menthol activates TRPM8 and may inhibit respiratory reflexes reducing irritation and cough. Menthol has a bimodal action on TRPA1, but inhibition may have an analgesic effect. Eucalyptus also activates TRPM8 and inhibits TRPA1 whilst down regulating P2X3, aiding in the reduction of cough, pain and airway irritation. Camphor inhibits TRPA1 and the activation of TRPM8 may add to the effects of menthol. Activation of TRPV1 by camphor, may also have an analgesic effect. CONCLUSIONS: The literature suggests that these plant derived substances have multifaceted actions and can interact with the TRP 'cough' receptors. The plant derived substances used in cough and cold medicines have the potential to target multiple symptoms experienced during a cold.


Assuntos
Canais de Cátion TRPM , Canais de Potencial de Receptor Transitório , Humanos , Mentol/farmacologia , Mentol/uso terapêutico , Cânfora/farmacologia , Canal de Cátion TRPA1 , Tosse/tratamento farmacológico , Tosse/etiologia , Dor , Analgésicos/farmacologia , Analgésicos/uso terapêutico
7.
Int J Mol Sci ; 24(12)2023 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-37373060

RESUMO

Ultraviolet (UV) radiation is a non-ionizing radiation, which has a cytotoxic potential, and it is therefore necessary to protect against it. Human skin is exposed to the longer-wavelength components of UV radiation (UVA and UVB) from the sun. In the present paper, we focused on the study of eight organic UV-absorbing compounds: astragalin, beta-carotene, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, hyperoside, 3-(4-methylbenzylidene)camphor, pachypodol, and trans-urocanic acid, as possible protectives of skin cells against UVA and UVB radiation. Their protective effects on skin cell viability, ROS production, mitochondrial membrane potential, liposomal permeability, and DNA integrity were investigated. Only some of the compounds studied, such as trans-urocanic acid and hyperoside, had a significant effect on the examined hallmarks of UV-induced cell damage. This was also confirmed by an atomic force microscopy study of morphological changes in HaCaT cells or a study conducted on a 3D skin model. In conclusion, hyperoside was found to be a very effective UV-protective compound, especially against UVA radiation. Commonly used sunscreen compounds such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, and 3-(4-methylbenzylidene)camphor turned out to be only physical UV filters, and pachypodol with a relatively high absorption in the UVA region was shown to be more phototoxic than photoprotective.


Assuntos
Raios Ultravioleta , Ácido Urocânico , Humanos , Raios Ultravioleta/efeitos adversos , Ácido Urocânico/farmacologia , Pele/metabolismo , Protetores Solares/farmacologia
8.
Exp Appl Acarol ; 89(2): 287-303, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36905473

RESUMO

Repellent and acaricidal activities of essential oils (EO) extracted from common yarrow (Achillea millefolium L.) and main chemical components were evaluated against Ixodes scapularis and Dermacentor variabilis adult ticks and nymphs. Flowers and leaves were collected from two locations, Harvest Moon trail (HMT) and Port Williams (PW) in Nova Scotia (Canada), and EO were extracted via hydro-distillation. Samples were analyzed using GC-MS, and differences in chemical composition and quantity of compounds detected were reported in relation to the collection site and plant parts. EO were both rich in germacrene D (HMT EO 21.5 ± 1.31% wt; PW EO 25.5 ± 0.76% wt); however, HMT flower EO has a higher concentration of camphor (9.9 ± 0.08% wt) compared to PW flower EO (3.0 ± 0.01% wt). Significant acaricidal activity was reported against I. scapularis adult ticks, particularly for HMT flower EO with a LD50 of 2.4% v/v (95% confidence interval = 1.74-3.35) at 24 h post-exposure. Germacrene D had the lowest LD50 of 2.0% v/v (95% CI 1.45-2.58) among the four compounds after 7 days. No significant acaricidal effect was observed on D. variabilis adult ticks. Yarrow PW flower EO exerted repellent activity towards I. scapularis nymphs (100% repellency up to 30 min); however, repellency significantly declined over time. Yarrow EO exert promising acaricidal and repellent properties, that may be used to manage Ixodes ticks and the diseases they vector.


Assuntos
Acaricidas , Achillea , Dermacentor , Repelentes de Insetos , Ixodes , Ixodidae , Óleos Voláteis , Animais , Acaricidas/farmacologia , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Repelentes de Insetos/farmacologia
9.
Molecules ; 28(5)2023 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-36903637

RESUMO

The experimental and theoretical study of influence of the conformational state and association on the chirality of the stereochemically nonrigid biologically active bis-camphorolidenpropylenediamine (CPDA) and its ability to induce the helical mesophase of alkoxycyanobiphenyls liquid-crystalline binary mixture was carried out. On the basis of quantum-chemical simulation of the CPDA structure, four relatively stable conformers were detected. A comparison of the calculated and experimental electronic circular dichroism (ECD) and 1H, 13C, 15N NMR spectra, as well as specific optical rotation and dipole moments, allowed to establish the most probable trans-gauche conformational state (tg) of dicamphorodiimine and CPDA dimer with a predominantly mutually parallel arrangement of molecular dipoles. The induction of helical phases in LC mixtures based on cyanobiphenyls and bis-camphorolidenpropylenediamine was studied by polarization microscopy. The clearance temperatures and the helix pitch of the mesophases were measured. The helical twisting power (HTP) was calculated. The decrease in HTP with increasing dopant concentration was shown to be connected with the CPDA association process in the LC phase. The effect of camphor-containing chiral dopants of various structures on nematic LCs was compared. The values of the permittivity and birefringence components of the CPDA solutions in CB-2 were measured experimentally. A strong effect of this dopant on the anisotropic physical properties of the induced chiral nematic was established. A significant decrease in the dielectric anisotropy was associated with the 3D compensation of the LC dipoles during the formation of the helix.

10.
Molecules ; 28(3)2023 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-36771181

RESUMO

Ten novel bifunctional quaternary ammonium salt phase-transfer organocatalysts were synthesized in four steps from (+)-camphor-derived 1,3-diamines. These quaternary ammonium salts contained either (thio)urea or squaramide hydrogen bond donor groups in combination with either trifluoroacetate or iodide as the counteranion. Their organocatalytic activity was evaluated in electrophilic heterofunctionalizations of ß-keto esters and in the Michael addition of a glycine Schiff base with methyl acrylate. α-Fluorination and chlorination of ß-keto esters proceeded with full conversion and low enantioselectivities (up to 29% ee). Similarly, the Michael addition of a glycine Schiff base with methyl acrylate proceeded with full conversion and up to 11% ee. The new catalysts have been fully characterized; the stereochemistry at the C-2 chiral center was unambiguously determined.

11.
AAPS PharmSciTech ; 24(7): 185, 2023 Sep 12.
Artigo em Inglês | MEDLINE | ID: mdl-37700198

RESUMO

Periodontitis is a widespread oral health problem caused by bacterial infections that lead to tooth loss and other systemic diseases. The aim of this study was to provide an alternative treatment for periodontitis by developing a metronidazole-loaded in situ forming matrix (ISM) using camphor as its matrix former. Five-percent w/w metronidazole dissolved in N-methyl pyrrolidone (NMP) with varying concentrations of camphor (30-50% w/w) and triacetin (0-25% w/w) were used. The physicochemical properties and antimicrobial activities of formulations were evaluated. Results showed that as the percentage of camphor increased, viscosity, density, contact angle, surface tension, and force of injection increased, while water tolerance decreased. The same trend was observed when increasing the triacetin concentration. The optimal metronidazole-loaded ISM was obtained at 40% w/w camphor and 5% w/w triacetin, which prolonged the release of metronidazole up to 6 days with Fickian diffusion release profile. The higher concentration of triacetin slowed down the phase inversion that led to an incomplete formation of the matrix and resulted in an inefficiently prolonged release of the metronidazole. Antimicrobial activities demonstrated that the developed formulation efficiently inhibited periodontitis-induced microorganisms including Porphyromonas gingivalis, Staphylococcus aureus, Escherichia coli, and Candida albicans. The metronidazole-loaded camphor-based ISM has potential as a new drug delivery system for periodontitis treatment.


Assuntos
Anti-Infecciosos , Metronidazol , Metronidazol/farmacologia , Cânfora , Triacetina , Candida albicans , Escherichia coli , Anti-Infecciosos/farmacologia
12.
Mol Divers ; 26(6): 3463-3483, 2022 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34982358

RESUMO

The development of new drugs requires a lot of time and high financial investments. It involves a research network in which there is the participation of several researchers from different areas. For a new drug to reach the market, thousands of substances must be evaluated. There are several tools for this and the use of suitable building blocks can facilitate the process by allowing a lead compound to have suitable parameters. These compounds are key structures containing special functional groups that also permit adequate synthetic transformations, leading to several structures of interest in a short period of time. In this review, the use of camphor nitroimine as a potential key building block is explored. Derived from camphor, an abundant natural product present in various plant species, this nitroimine has proved to be quite versatile, allowing the access to substances with miscellaneous biological activities, ligands to asymmetric catalysis, asymmetric oxidants, O-N transfer agents and other applications. Its easy conversion to camphecene and other derivatives is described, as well as their applications in medicinal chemistry. Druglikeness analyses were performed on these studied agents as well as on their bioactive derivatives in order to assess their use in the development of potential drugs.


Assuntos
Produtos Biológicos , Cânfora , Catálise
13.
Chirality ; 34(8): 1038-1043, 2022 08.
Artigo em Inglês | MEDLINE | ID: mdl-35531652

RESUMO

Inositol phosphates and inositol phospholipids are ubiquitous in biochemistry and play a central role in cell signaling and regulation events. For this reason, their synthesis has attracted widespread interest. This paper describes the preparation of a new optically active inositol phosphate derivative, 2-O-acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosityl diphenylphosphate (6), and its characterization by spectroscopic methods. Compound (6) represents a useful intermediate for the preparation of inositol phosphate and phospholipids, in particular of glycerophosphoinositol (GPI), a natural anti-inflammatory agent.


Assuntos
Fosfatos de Inositol , Fosfolipídeos , Fosfatos de Inositol/química , Estereoisomerismo
14.
Chirality ; 34(2): 253-294, 2022 02.
Artigo em Inglês | MEDLINE | ID: mdl-34783096

RESUMO

In the studies of chiral organic stereochemistry, it is important to use enantiopure compounds. For this purpose, the chiral HPLC (High-Pressure Liquid Chromatography) columns containing chiral stationary phases were invented by Y. Okamoto and coworkers for enantio-separating various racemic compounds. In addition, the use of chiral auxiliaries is also useful for preparing enantiopure compounds and also for determining their absolute configurations, where covalent-bonded diastereomers are separated by HPLC on silica gel. In this review article, these HPLC methods will be discussed together with the applications to some interesting organic compounds including light-powered chiral molecular motors.


Assuntos
Estereoisomerismo , Cromatografia Líquida de Alta Pressão/métodos , Cristalografia por Raios X , Sílica Gel , Análise Espectral
15.
Pestic Biochem Physiol ; 184: 105124, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35715062

RESUMO

The fall webworm, Hyphantria cunea (Drury), is a harmful polyphagous global defoliator. The major chemical components of Artemisia annua essential oil (EO) was found to contain (±)-camphor (16.42%), 1,8-cineole (6.22%), α-pinene (6%), caryophyllene (5.19%), and α-selinene (5.17%). The highest toxicity was recorded for EO of A. annua (LD50 = 305.05 µg/larva), followed by (±)-camphor (LD50 = 465.03 µg/larva) and 1,8-cineole (LD50 = 573.49 µg/larva). The binary mixtures of compounds expressed a weaker activity compared to individuals. The (±)-camphor was found to be antagonistic to 1,8-cineole. The biochemical compounds of treated larvae were also determined. The activity level of alanin and aspartate aminotransferase decreased sharply while acid and alkaline phosphatase increased. Activity of lactate dehydrogenase was significantly higher than the control group at 24 h, but decreased significantly after 48 h in all treatments. The activity of esterases were decreased in the treated larvae. The glutathione S-transferase significantly increased in all time intervals. Overall the current results suggest that the sweet wormwood (A. annua) EO and its components could be a safe and environmentally friendly approach in possible control of fall webworm (H. cunea).


Assuntos
Artemisia annua , Mariposas , Óleos Voláteis , Animais , Artemisia annua/química , Cânfora , Eucaliptol , Larva , Óleos Voláteis/química , Óleos Voláteis/toxicidade
16.
Chem Biodivers ; 19(3): e202100954, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-35170197

RESUMO

The most abundant volatile compounds of sweet wormwood (Artemisia annua L.) essential oil were artemisia ketone (25.4 %) and trans-caryophyllene (10.2 %), followed by 1,8-cineole, camphor, germacrene D and ß-selinene. The major volatile compounds in the hydrosol were camphor (25.1 %), 1,8-cineole (20.5 %) and artemisia ketone (10.7 %), followed by trans-pinocarveol and yomogi alcohol. Tested essential oil was rich in oxygenated monoterpenes and sesquiterpene hydrocarbons, while the former were identified as the major class of volatile compounds in the hydrosol, due to higher water solubility. Classification of all sweet wormwood chemotypes, according to essential oil composition, in available literature (17 studies and 61 accessions) could be done according to four chemotypes: artemisia ketone+artemisia alcohol (most abundant), artemisia ketone, camphor and nonspecific chemotype. According to this classification, essential oil of sweet wormwood from this study belongs to artemisia ketone (content varied between 22.1 and 55.8 %). Bearing in mind that hydrosols are a by-product of industrial production of essential oils, and the fact that sweet wormwood hydrosol has high contents of camphor, 1,8-cineole and artemisia ketone, there is a great potential for the use of this aromatic plant primary processing waste product as a water replacement in cosmetic industry, beverages flavoring, for food preservation, as well as in post-harvest pre-storage treatments in organic agriculture.


Assuntos
Artemisia annua , Artemisia , Óleos Voláteis , Cânfora , Eucaliptol , Sérvia
17.
Chem Biodivers ; 19(10): e202200608, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-36111638

RESUMO

Twelve novel camphor sulfonamide derivatives 2a-2l were synthesized and characterized by 1 H-NMR, 13 C-NMR and HRMS spectra. The anti-fungal/oomycete activity bioassay showed that some of the title compounds displayed moderate to good anti-fungal/oomycete activities against B. dothidea and P. capsici. Compound 2d exhibited the best in vitro antifungal activity toward B. dothidea. The in vivo experiment revealed that compound 2d possessed considerable anti-B. dothidea effect at 200 mg/L. Mechanism study showed that compound 2d could increase the cell membrane permeability. In addition, the in vitro enzyme inhibition assay and molecular docking results indicated that compound 2d could be a potential SDH inhibitor.


Assuntos
Ascomicetos , Oomicetos , Antifúngicos/química , Simulação de Acoplamento Molecular , Cânfora/farmacologia , Sulfanilamida , Sulfonamidas/farmacologia , Relação Estrutura-Atividade
18.
Int J Mol Sci ; 23(22)2022 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-36430756

RESUMO

The camphor tree (Cinnamomum camphora (L.) Presl.) is the representative species of subtropical evergreen broadleaved forests in eastern Asia and an important raw material for essential oil production worldwide. Although MYBs have been comprehensively characterized and their functions have been partially resolved in many plants, it has not been explored in C. camphora. In this study, 121 CcMYBs were identified on 12 chromosomes in the whole genome of C. camphora and found that CcMYBs were mainly expanded by segmental duplication. They were divided into 28 subgroups based on phylogenetic analysis and gene structural characteristics. In the promoter regions, numerous cis-acting elements were related to biological processes. Analysis of RNA sequencing data from seven tissues showed that CcMYBs exhibited different expression profiles, suggesting that they have various roles in camphor tree development. In addition, combined with the correlation analysis of structural genes in the flavonoid synthesis pathway, we identified CcMYBs from three subgroups that might be related to the flavonoid biosynthesis pathway. This study systematically analyzed CcMYBs in C. camphora, which will set the stage for subsequent research on the functions of CcMYBs during their lifetime and provide valuable insights for the genetic improvement of camphor trees.


Assuntos
Cinnamomum camphora , Óleos Voláteis , Cinnamomum camphora/genética , Cinnamomum camphora/química , Filogenia , Óleos Voláteis/química , Florestas , Flavonoides/metabolismo
19.
Molecules ; 27(4)2022 Feb 14.
Artigo em Inglês | MEDLINE | ID: mdl-35209050

RESUMO

A reverse-phase high-performance liquid chromatography method was developed to determine and quantify capsaicin (trans-8-methyl-N-vanillyl-6- nonenamid), dihydrocapsaicin (8-methyl-N-vanillylnonanamide), and camphor (trimethylbicyclo[2.2.1]heptan-2-one). It is applicable in analyses of over-the-counter (OTC) medications for topical use and raw materials such as chili pepper oleoresin. Chromatographic separation was carried out on a C18 column using an isocratic flow of the mobile phase containing acetonitrile and ultrapure water in a ratio of 2:3, with pH adjusted to 3.2 using glacial acetic acid, and a flow rate of 1.5 mL/min. The concentration of the eluting compounds was monitored by a diode-array detector at a wavelength of 281 nm. The method was evaluated for several validation parameters, including selectivity, accuracy (confidence intervals < 0.05%), repeatability, and intermediate precision. The limit of detection (LOD) was determined to be 0.070 µg/mL for capsaicin, 0.211 µg/mL for dihydrocapsaicin, and 0.060 µg/mL for camphor. The limit of quantification (LOQ) was determined to be 0.212 µg/mL for capsaicin, 0.640 µg/mL for dihydrocapsaicin, and 0.320 µg/mL for camphor. Linearity was set in the range of 2.5-200 µg/mL for capsaicin and dihydrocapsaicin and 25-2000 µg/mL for camphor. The suggested analytical method can be used for quality control of formulated pharmaceutical products containing capsaicinoids, camphor, and propolis.


Assuntos
Cânfora/análise , Cânfora/química , Capsaicina/análise , Capsaicina/química , Cromatografia Líquida de Alta Pressão , Medicamentos sem Prescrição/análise , Medicamentos sem Prescrição/química , Administração Tópica , Cânfora/administração & dosagem , Capsaicina/administração & dosagem , Capsaicina/análogos & derivados , Fracionamento Químico/métodos , Cromatografia Líquida de Alta Pressão/métodos , Estrutura Molecular , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
20.
Molecules ; 27(9)2022 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-35566046

RESUMO

Camphor tree (Cinnamomum camphora) is an ornamental plant that has been cultivated for a long time to obtain wood or camphor. Furthermore, its essential oil can be used as an alternative medicine and is an important source of perfume. Camphor obtained from camphor trees has long been used as a treatment for various symptoms such as inflammation, infection, congestion, muscle pain, and irritation in various regions. The purpose of this literature review is to provide knowledge of the well-established, wide, and extensive applications of camphor both in traditional and modern applications. Despite many studies focused on the essential oil of the camphor tree, there is a lack of systematic studies of its extraction or separation. Besides, various components of camphor are not fully understood, and further research is needed on the medicinal effects of individual components of C. camphor. The genus Cinnamomum has crucial economic value and theoretical significance. However, further systematic reviews and investigative studies based on existing research are needed to promote the modernization process of traditional applications of camphor. For proper use of the essential oil of C. camphora, it is imperative to consider its possible effects on humans and the environment.


Assuntos
Cinnamomum camphora , Óleos Voláteis , Perfumes , Cânfora , Humanos , Óleos Voláteis/farmacologia , Folhas de Planta
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