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1.
Sci Rep ; 14(1): 10592, 2024 05 08.
Artigo em Inglês | MEDLINE | ID: mdl-38719900

RESUMO

Umbelliferous (Apiaceae) vegetables are widely consumed worldwide for their nutritive and health benefits. The main goal of the current study is to explore the compositional heterogeneity in four dried umbelliferous vegetables viz, celery, coriander, dill, and parsley targeting their volatile profile using gas chromatography-mass spectrometry (GC-MS). A total of 133 volatile metabolites were detected belonging to 12 classes. Aromatic hydrocarbons were detected as the major components of the analyzed vegetables accounting ca. 64.0, 62.4, 59.5, and 47.8% in parsley, dill, celery, and coriander, respectively. Aliphatic hydrocarbons were detected at ca. 6.39, 8.21, 6.16, and 6.79% in parsley, dill, celery, and coriander, respectively. Polyunsaturated fatty acids (PUFA) of various health benefits were detected in parsley and represented by roughanic acid and α-linolenic acid at 4.99 and 0.47%, respectively. Myristicin and frambinone were detected only in parsley at 0.45 and 0.56%. Investigation of antibacterial activity of umbelliferous vegetables n-hexane extract revealed a moderate antibacterial activity against Gram-positive and Gram-negative bacteria with higher activity for celery and dill against Staphylococcus aureus with inhibition zone 20.3 mm compared to 24.3 mm of the standard antibacterial drug.


Assuntos
Antibacterianos , Cromatografia Gasosa-Espectrometria de Massas , Hexanos , Compostos Fitoquímicos , Verduras , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/análise , Verduras/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Hexanos/química , Apiaceae/química , Testes de Sensibilidade Microbiana , Derivados de Alilbenzenos , Ácido alfa-Linolênico/análise , Ácido alfa-Linolênico/farmacologia , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Óleos de Plantas/farmacologia , Óleos de Plantas/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Ácidos Graxos Insaturados/análise , Staphylococcus aureus/efeitos dos fármacos , Dioxolanos
2.
Sci Rep ; 14(1): 10052, 2024 05 02.
Artigo em Inglês | MEDLINE | ID: mdl-38698117

RESUMO

The Apiaceae family contains many species used as food, spice and medicinal purposes. Different parts of plants including seeds could be used to obtain essential (EO) oils from members of the Apiaceae family. In the present study, EOs were components obtained through hydrodistillation from the seeds of anise (Pimpinella anisum), carrot (Daucus carota), celery (Apium graveolens), dill (Anethum graveolens), coriander (Coriandrum sativum), fennel (Foeniculum vulgare), and cumin (Cuminum cyminum). EO constituents were determined with Gas Chromatography/Mass Spectrometry (GC-MS) and Gas Chromatography/Flame Ionization Detector (GC-FID) and their antioxidant capacities were determined with the cupric reducing antioxidant capacity (CUPRAC) and 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) methods. The antimicrobial activity of EOs were tested against four pathogenic bacteria. Phenylpropanoids in anise (94.87%) and fennel (92.52%), oxygenated monoterpenes in dill (67.59%) and coriander (98.96%), monoterpene hydrocarbons in celery (75.42%), mono- (45.42%) and sesquiterpene- (43.25%) hydrocarbons in carrots, monoterpene hydrocarbon (34.30%) and aromatic hydrocarbons (32.92%) in cumin were the major compounds in the EOs. Anethole in anise and fennel, carotol in carrot, limonene in celery, carvone in dill, linalool in coriander, and cumin aldehyde in cumin were predominant compounds in these EOs. The high hydrocarbon content in cumin EO gave high CUPRAC activity (89.07 µmol Trolox g-1), and the moderate monoterpene hydrocarbon and oxygenated monoterpene content in dill EO resulted in higher DPPH activity (9.86 µmol Trolox g-1). The in vitro antibacterial activity of EOs against Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli was evaluated using the agar diffusion method and the minimum bactericidal concentration was determined. Coriander, cumin and dill EOs showed inhibitory effect against all tested strains except P. aeruginosa. While fennel and celery EOs were effective against E. coli and B. cereus strains, respectively, anise and carrot EOs did not show any antibacterial effect against the tested bacteria. Hierarchical Cluster Analysis (HCA) produced four groups based on EO constituents of seven species. The potential adoption of the cultivated Apiaceae species for EO extraction could be beneficial for the wild species that are endangered by over collection and consumption.


Assuntos
Antioxidantes , Apiaceae , Daucus carota , Foeniculum , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/análise , Apiaceae/química , Daucus carota/química , Foeniculum/química , Cuminum/química , Cromatografia Gasosa-Espectrometria de Massas , Antibacterianos/farmacologia , Antibacterianos/química , Testes de Sensibilidade Microbiana , Coriandrum/química , Sementes/química , Anethum graveolens/química , Pimpinella/química , Óleos de Plantas/farmacologia , Óleos de Plantas/química , Apium/química
3.
Pak J Pharm Sci ; 37(1): 147-154, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38741411

RESUMO

Zeravschania khorasanica, a species endemic to the eastern part of Iran, possesses distinct characteristics that distinguish it from its two closely related species. This research employed five different extraction techniques to identify the active components, total phenolic content and in vitro antioxidant activity of the extract. Furthermore, hydro-distillation was utilized for GC/MS analysis to determine the composition of the essential oil. The total phenolic content was estimated using the Folin-Ciocalteu assay and the antioxidant capacity was evaluated using the DPPH radical scavenging test. The findings revealed that ethanolic Soxhlet extraction yielded the highest efficiency in extracting total phenolic content (88.19 ±1.99 gallic acid mg/100g). In contrast, water maceration extraction demonstrated the highest antioxidant activity (68.1 ±5.4%). Interestingly, the study uncovered that there is no significant positive correlation between the phenolic content and the antioxidant activity of the plant. Additionally, HPLC analysis identified three phenolic constituents in the extract. The Soxhlet extraction method yielded the highest levels of chlorogenic acid (5.8 ppm), caffeic acid (4.1 ppm) and salicylic acid (10.3 ppm). As per the GC/MS analysis, a total of eleven compounds were identified. The predominant compounds were elemicin at 58.19% and trans--bergamotene at 25.78%.


Assuntos
Antioxidantes , Apiaceae , Cromatografia Gasosa-Espectrometria de Massas , Fenóis , Extratos Vegetais , Solventes , Antioxidantes/isolamento & purificação , Antioxidantes/análise , Antioxidantes/farmacologia , Antioxidantes/química , Fenóis/análise , Fenóis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Irã (Geográfico) , Solventes/química , Apiaceae/química , Cromatografia Líquida de Alta Pressão , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Compostos de Bifenilo/química , Picratos/química , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/análise
4.
J Chromatogr A ; 1723: 464716, 2024 May 24.
Artigo em Inglês | MEDLINE | ID: mdl-38640881

RESUMO

Saposhnikoviae Radix (SR) may enhance the pharmacodynamics of Huangqi Chifeng Tang (HQCFT) in the treatment of cerebral infarction according to our previous research, but the underlying mechanism is unknown. Herein, an in vivo pharmacokinetic assay in rats and in vitro MDCK-MDR1 cell assays were used to investigate the possible mechanism of SR, its main components, and its interactions with Astragali Radix (AR) and Paeoniae Radix (PR). An ultrahigh-performance liquid chromatography-tandem mass spectrometry (UPLC‒MS/MS)-based analytical method for quantifying astragaloside IV (ASIV) and paeoniflorin (PAE) in microdialysis and transport samples was developed. The pharmacokinetic parameters of SR were determined using noncompartmental analyses CCK-8 assays were used to detect the cytotoxicity of ASIV, PAE, cimifugin (CIM), prim-o-glucosylcimifugin (POG) and their combinations. Moreover, drug transport was studied using MDCK-MDR1 cells. Western blotting was performed to measure the protein expression levels of P-GP and MRP1. Claudin-5, ZO-1, and F-actin expression was determined via immunohistochemical staining of MDCK-MDR1 cells. harmacokinetic studies revealed that, compared with those of Huangqi Chifeng Tang-Saposhnikoviae Radix (HQCFT-SR), the Tmax of ASIV increased by 11.11 %, and the MRT0-t and Tmax of PAE increased by 11.19 % and 20 %, respectively, in the HQCFT group. Transport studies revealed that when ASIV was coincubated with 28 µM CIM or POG, the apparent permeability coefficient (Papp) increased by 71.52 % and 50.33 %, respectively. Coincubation of PAE with 120 µM CIM or POG increased the Papp by 87.62 % and 60.95 %, respectively. Moreover, CIM and POG significantly downregulated P-gp and MRP1 (P < 0.05), inhibited the expression of Claudin-5, ZO-1, and F-actin (P < 0.05), and affected intercellular tight junctions (TJs). In conclusion, our study successfully established a selective, sensitive and reproducible UPLC‒MS/MS analytical method to detect drug‒drug interactions between SR, AR and PR in vivo and in vitro, which is beneficial for enhancing the therapeutic efficacies of AR and PR. Moreover, this study provides a theoretical basis for further research on the use of SR as a drug carrier.


Assuntos
Medicamentos de Ervas Chinesas , Glucosídeos , Monoterpenos , Ratos Sprague-Dawley , Saponinas , Espectrometria de Massas em Tandem , Triterpenos , Animais , Glucosídeos/farmacocinética , Glucosídeos/análise , Glucosídeos/química , Glucosídeos/farmacologia , Saponinas/farmacocinética , Saponinas/farmacologia , Saponinas/química , Saponinas/análise , Monoterpenos/análise , Triterpenos/farmacologia , Triterpenos/farmacocinética , Triterpenos/química , Triterpenos/análise , Cães , Ratos , Células Madin Darby de Rim Canino , Espectrometria de Massas em Tandem/métodos , Masculino , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/farmacocinética , Cromatografia Líquida de Alta Pressão/métodos , Apiaceae/química , Interações Ervas-Drogas , Interações Medicamentosas , Reprodutibilidade dos Testes
5.
Fitoterapia ; 174: 105876, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38431027

RESUMO

Nine polyacetylenes, including five new compounds named sadivaethynes E-I (1-5), were isolated from the roots of Saposhnikovia divaricata. Structural elucidation of compounds 1-5 was established by extensive spectroscopic analysis, quantum chemical calculations and DP4+ probability analysis. Among them, the absolute configuration of compound 1-2, 4-5 was unambiguous determined by ECD. Also, all compounds were evaluated for cytotoxicity against two human cancer cell lines (A549, HEPG2) in vitro, compound 9 showed moderate inhibitory effect with an IC50 value of 11.66 µM against HEPG2.


Assuntos
Apiaceae , Poli-Inos , Humanos , Estrutura Molecular , Poli-Inos/farmacologia , Poli-Inos/análise , Poli-Inos/química , Raízes de Plantas/química , Extratos Vegetais/química , Apiaceae/química
6.
Int J Biol Macromol ; 265(Pt 1): 130907, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38492707

RESUMO

Traditional hot water reflux extraction, ultrasonic-water extraction (UW), ultrasonic-natural deep eutectic solvent (NADES) extraction (U-NADES), ultrasonic-water and enzyme extraction (U-W-E) and ultrasonic-NADES and enzyme extraction (U-NADES-E) are employed for the extraction of Rhizoma et Radix Notopterygii polysaccharides (RNP), in which, the U-NADES-E has being proved as the most effective method. Response Surface Methodology (RSM) was utilized to optimize the conditions for U-NADES-E method. Using the optimal extraction conditions, the yield of RNP can be enhanced by nearly two-fold in comparison to the traditional extraction method, achieving a yield of 7.38 %, with a mere 30-min treatment and low ultrasonic power at 240 W. The RNP's composition included Rhamnose, Arabinose, Galactose, Glucose and Galacturonic Acid by high-performance anion-exchange chromatography. The polysaccharides from two different species of Rhizoma et Radix Notopterygii have also been characterized and identified. Network pharmacology and molecular docking predict that RNP may exert its effects in vivo through binding to PPARA, ACE and REN proteins, thereby potentially impacting diabetes outcomes. This study proposes a new, efficient, energy-saving and environmentally-friendly method for the extraction of RNP.


Assuntos
Apiaceae , Simulação de Acoplamento Molecular , Apiaceae/química , Rizoma/química , Solventes , Água/análise , Polissacarídeos/química
7.
Phytomedicine ; 128: 155449, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38518644

RESUMO

BACKGROUND: Peucedanum japonicum Thunb. (PJ) is a vegetable widely consumed in East Asia and is known to have anticancer and anti-inflammatory effects. However, the effect of PJ on muscle atrophy remains elusive. PURPOSE: This study aimed to investigate the effect of PJ and its active compound on dexamethasone (DEX)-induced muscle atrophy. METHODS: We performed qualitative and quantitative analysis of PJ using ultra-performance liquid chromatography-mass spectrometry tandem mass spectrometry (UPLC-MS/MS) and high-performance liquid chromatography (HPLC), respectively. The efficacy of PJ and its main compound 4-caffeoylquinic acid (CQA) on muscle atrophy was evaluated in DEX-induced myotube atrophy and DEX-induced muscle atrophy in mouse myoblasts (C2C12) and C57BL/6 mice, in vitro and in vivo, respectively. RESULTS: The UPLC-MS/MS and HPLC data showed that the concentration of 4-CQA in PJ was 18.845 mg/g. PJ and 4-CQA treatments significantly inhibited DEX-induced myotube atrophy by decreasing protein synthesis and glucocorticoid translocation to the nucleus in C2C12 myotubes. In addition, PJ enhanced myogenesis by upregulating myogenin and myogenic differentiation 1 in C2C12 cells. PJ supplementation effectively increased muscle function and mass, downregulated atrogenes, and decreased proteasome activity in C57BL/6 mice. Additionally, PJ effectively decreased the nuclear translocation of forkhead transcription factor 3 alpha by inhibiting glucocorticoid receptor. CONCLUSION: Overall, PJ and its active compound 4-CQA alleviated skeletal muscle atrophy by inhibiting protein degradation. Hence, our findings present PJ as a potential novel pharmaceutical candidate for the treatment of muscle atrophy.


Assuntos
Apiaceae , Dexametasona , Camundongos Endogâmicos C57BL , Atrofia Muscular , Extratos Vegetais , Ácido Quínico/análogos & derivados , Animais , Atrofia Muscular/induzido quimicamente , Atrofia Muscular/tratamento farmacológico , Dexametasona/farmacologia , Camundongos , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Apiaceae/química , Masculino , Linhagem Celular , Espectrometria de Massas em Tandem , Fibras Musculares Esqueléticas/efeitos dos fármacos , Ácido Quínico/farmacologia , Cromatografia Líquida de Alta Pressão , Miogenina/metabolismo
8.
Int J Biol Macromol ; 255: 128218, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37992933

RESUMO

Peucedanum praeruptorum Dunn, a traditional Chinese medicine rich in coumarin, belongs to the Apiaceae family. A high-quality assembled genome of P. praeruptorum is lacking, which has posed obstacles to functional identification and molecular evolution studies of genes associated with coumarin production. Here, a chromosome-scale reference genome of P. praeruptorum, an important medicinal and aromatic plant, was first sequenced and assembled using Oxford Nanopore Technologies and Hi-C sequencing. The final assembled genome size was 1.83 Gb, with a contig N50 of 11.12 Mb. The entire BUSCO evaluation and second-generation read comparability rates were 96.0 % and 99.31 %, respectively. Furthermore, 99.91 % of the genome was anchored to 11 pseudochromosomes. The comparative genomic study revealed the presence of 18,593 orthogroups, which included 476 species-specific orthogroups and 1211 expanded gene families. Two whole-genome duplication (WGD) events and one whole-genome triplication (WGT) event occurred in P. praeruptorum. In addition to the γ-WGT shared by core eudicots or most eudicots, the first WGD was shared by Apiales, while the most recent WGD was unique to Apiaceae. Our study demonstrated that WGD events that occurred in Apioideae highlighted the important role of tandem duplication in the biosynthesis of coumarins and terpenes in P. praeruptorum. Additionally, the expansion of the cytochrome P450 monooxygenase, O-methyltransferase, ATP-binding cassette (ABC) transporter, and terpene synthase families may be associated with the abundance of coumarins and terpenoids. Moreover, we identified >170 UDP-glucosyltransferase members that may be involved in the glycosylation post-modification of coumarins. Significant gene expansion was observed in the ABCG, ABCB, and ABCC subgroups of the ABC transporter family, potentially facilitating the transmembrane transport of coumarins after bolting. The P. praeruptorum genome provides valuable insights into the machinery of coumarin biosynthesis and enhances our understanding of Apiaceae evolution.


Assuntos
Apiaceae , Cumarínicos , Cumarínicos/química , Sistema Enzimático do Citocromo P-450/genética , Apiaceae/genética , Apiaceae/química , Metiltransferases/genética , Cromossomos
9.
Phytochem Anal ; 35(1): 17-27, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37501406

RESUMO

INTRODUCTION: Saposhnikovia divaricata (Turcz.) Schischk is one of the most widely used Chinese herbs worldwide. It has anti-inflammatory and analgesic properties and hence has a high clinical value. As the moisture level in S. divaricata is high after harvest, it requires drying. OBJECTIVE: We aimed to find a scientific drying method and optimize the drying conditions of the best drying method of S. divaricata using response surface methodology (RSM). METHODOLOGY: The effects of 4 different drying methods on the contents of prim-O-glucosylcimifugin, cimifugin, 5-O-methylvisamminol, and sec-O-glucosylhamaudol were determined using high-performance liquid chromatography. Chroma, the rehydration ratio, and active component content were used as indices, and slice thickness, drying temperature, and drying time were used as independent variables to optimize the drying conditions of the optimal drying method of S. divaricata using RSM combined with the Box-Behnken design. RESULTS: The results showed that the optimal drying conditions were as follows: slice thickness, 4.00 mm; drying temperature, 60°C; and drying time, 15 h. CONCLUSION: Under optimal drying conditions, the measured values were extremely close to the predicted values. The results of variance analysis showed that the model had a high degree of fit and the drying conditions of S. divaricata were optimized successfully.


Assuntos
Apiaceae , Medicamentos de Ervas Chinesas , Medicamentos de Ervas Chinesas/análise , Temperatura , Apiaceae/química , Cromatografia Líquida de Alta Pressão/métodos
10.
Nat Prod Res ; 38(6): 1024-1035, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-37211799

RESUMO

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. From the roots of this accession of species, not previously investigated, four coumarins, grandivittin, aegelinol benzoate, felamidin and aegelinol, and two terpenoids, (2E)-3-methyl-4-[(3-methyl-1-oxo-2-buten-1yl)oxy]-2-butenoic acid and pressafonin-A, were isolated and spectroscopically characterized. The last one was never detected in Ferulago species. The evaluation of the anti-tumor effects of F. nodosa coumarins on colon cancer HCT116 cells showed only a modest effect on reduction of tumor cell viability. For aegelinol, the reduction of colon cancer cell viability already appears with 25 µΜ, while using 50 e 100 µM doses of marmesin the residual viability amounted to 70% and 54%, respectively. This effect resulted more evident at higher doses of compounds (at 200 µM from 80% to 0%). The most effective compounds resulted coumarins lacking ester group.


Assuntos
Apiaceae , Neoplasias do Colo , Cumarínicos/farmacologia , Cumarínicos/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Compostos Fitoquímicos/farmacologia , Apiaceae/química , Neoplasias do Colo/tratamento farmacológico
11.
J Nat Med ; 78(2): 267-284, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38133706

RESUMO

Our representative studies to achieve sustainable use of crude drugs and ensure their stable quality are introduced: comprehensive studies on genetic, chemical, and sometimes pharmacological diversity of Asian medicinal plants including Paeonia lactiflora, Glycyrrhiza uralensis, Ephedra spp., Saposhnikovia divaricata, and Curcuma spp., as well as their related crude drugs. (1) For peony root, after genetic and chemical diversity analysis of crude drug samples including white and red peony root in China, the value-added resources with quality similar to red peony root were explored among 61 horticultural P. lactiflora varieties, and two varieties were identified. In addition, an optimized post-harvest processing method, which resulted in high contents of the main active components in the produced root, was developed to promote cultivation and production of brand peony root. (2) Alternative resources of glycyrrhiza, ephedra herb and saposhnikovia root and rhizome of Japanese Pharmacopoeia grade were discovered in eastern Mongolia after field investigation and quality assessment comparing Mongolian plants with Chinese crude drugs. Simultaneously, suitable specimens and prospective regions for cultivation were proposed. (3) Because of the wide distribution and morphological similarities of Curcuma species, classification of some species is debated, which leads to confusion in the use of Curcuma crude drugs. Molecular analyses of the intron length polymorphism (ILP) markers in genes encoding diketide-CoA synthase (DCS) and curcumin synthase (CURS) and trnK sequences, combined with essential oils analysis, were demonstrated as useful for standardization of Curcuma crude drugs. The above studies, representing various facets, can be applied to other crude drugs.


Assuntos
Apiaceae , Glycyrrhiza uralensis , Paeonia , Plantas Medicinais , Plantas Medicinais/genética , Estudos Prospectivos , Rizoma , Paeonia/química , Apiaceae/química , Padrões de Referência
12.
Nat Prod Res ; 38(1): 1-9, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-35895127

RESUMO

Dichloromethane and butanol extracts of the roots of Prangos pabularia were analyzed to determine chemical constituents and biological activity. The new coumarin 1, yuganin B ((5-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-3,4-dihydroxytetrahydrofuran-3-yl)methyl 4-hydroxy-3-methoxybenzoate) along with three phenolic and twenty-four known coumarins were isolated from the roots of Prangos pabularia, and the structures of these isolated compounds were elucidated by UV, HR-ESIMS, and 1 D and 2 D NMR spectroscopy. In addition, the anti-melanogenic effect of several of the isolated individual compounds and their inhibitory effect on B16 cells were evaluated. Isolating and testing compounds may proof to be useful in the treatment of hyperpigmentation and as a skin-whitening agent in the cosmetics industry.


Assuntos
Apiaceae , Extratos Vegetais , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Tadjiquistão , Cumarínicos/farmacologia , Cumarínicos/química , Apiaceae/química
13.
Plant Cell Physiol ; 64(12): 1436-1448, 2023 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-37948767

RESUMO

Tetrahydrofuran ring formation from dibenzylbutyrolactone lignans is a key step in the biosynthesis of aryltetralin lignans including deoxypodophyllotoxin and podophyllotoxin. Previously, Fe(II)- and 2-oxoglutarate-dependent dioxygenase (2-ODD) from Podophyllum hexandrum (Himalayan mayapple, Berberidaceae) was found to catalyze the cyclization of a dibenzylbutyrolactone lignan, yatein, to give deoxypodophyllotoxin and designated as deoxypodophyllotoxin synthase (DPS). Recently, we reported that the biosynthesis of deoxypodophyllotoxin and podophyllotoxin evolved in a lineage-specific manner in phylogenetically unrelated plant species such as P. hexandrum and Anthriscus sylvestris (cow parsley, Apiaceae). Therefore, a comprehensive understanding of the characteristics of DPSs that catalyze the cyclization of yatein to deoxypodophyllotoxin in various plant species is important. However, for plant species other than P. hexandrum, the isolation of the DPS enzyme gene and the type of the enzyme, e.g. whether it is 2-ODD or another type of enzyme such as cytochrome P-450, have not been reported. In this study, we report the identification and characterization of A. sylvestris DPS (AsDPS). Phylogenetic analysis showed that AsDPS belonged to the 2-ODD superfamily and shared moderate amino acid sequence identity (40.8%) with P. hexandrum deoxypodophyllotoxin synthase (PhDPS). Recombinant protein assay indicated that AsDPS and PhDPS differ in terms of the selectivity of substrate enantiomers. Protein modeling using AlphaFold2 and site-directed mutagenesis indicated that the Tyr305 residue of AsDPS probably contributes to substrate recognition. This study advances our understanding of the podophyllotoxin biosynthetic pathway in A. sylvestris and provides new insight into 2-ODD involved in plant secondary (specialized) metabolism.


Assuntos
Apiaceae , Lignanas , Podofilotoxina/química , Filogenia , Lignanas/metabolismo , Apiaceae/química , Apiaceae/metabolismo
14.
Biomolecules ; 13(11)2023 11 20.
Artigo em Inglês | MEDLINE | ID: mdl-38002357

RESUMO

Petroselinic fatty acid (PeFA) is considered a rare fatty acid and one of the most important fatty acids in the Apiaceae family. Its content varies depending on plant species, geographical origin, extraction method, ripeness, etc. Indeed, reported levels of petroselinic fatty acid range from 10.4 to 75.6% (in anise seed oil), 1 to 81.9% (in coriander seed oil), 28.5 to 57.6% (in caraway seed oil), 49.4 to 75.6% (in celery seed oil), 41.3 to 61.8% (in caraway seed oil), 79.9 to 87.2% (in dill seed oil), 43.1 to 81.9% (in fennel seed oil), and 35 to 75.1% (parsley seed oil). In this review, we also show current knowledge about genes encoding biosynthesis, from the desaturation of 16:0-ACP to petroselinic acid stored in triacylglycerol in the seeds. Furthermore, petroselinic acid is not related to the synthesis of ABA. PeFA was successfully isolated from Apiaceae family plant seeds in order to study their reactivity and biological activities. Several investigations showed that this fatty acid has a wide range of biological potentials, including antidiabetic, antibacterial, and antifungal activities. In cosmetics, PeFA alone or in association with other active compounds has interesting applications as an anti-inflammatory agent for the treatment of skin, hair, and nail disorders.


Assuntos
Apiaceae , Apiaceae/química , Óleos de Plantas/química , Ácidos Graxos/química
15.
Chem Biodivers ; 20(12): e202300827, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37884443

RESUMO

This work aimed to investigate the variability of the chemical composition of the aromatic halophyte Crithmum maritimum L. essential oils according to the geographical origin and separated organs, using a statistical approach based on the multiple analysis of variance and the Principal Component Analyses. One hundred twenty samples were collected from three distinct bioclimatic regions (10 samples×3 provenances×4 organs). Hydrodistillation of separated organs (roots, stems, leaves and flowers) yielded 0.13 to 1.75 % of the dry matter. Chemical investigation of the volatile compounds by Gas chromatography-mass spectrometry showed that C. maritimum essential oils were dominated by monoterpenes hydrocarbons, oxygenated monoterpenes, and phenylpropanoids varying, respectively, from 33.3 to 66.9, from 7.8 to 46.6 and from 4.5 to 57.2 % according to organs and localities. Statistical analyses identified three different chemotypes depending on the geographic origin as follow: γ-Terpinene-Thymol methyl ether / Dillapiole / Thymol methyl ether-Dillapiole.


Assuntos
Apiaceae , Éteres Metílicos , Óleos Voláteis , Timol , Óleos Voláteis/química , Apiaceae/química , Monoterpenos/análise
16.
Chem Biodivers ; 20(12): e202301302, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37906119

RESUMO

Ferulago bernardii Tomk & M. Pimen belongs to Apiaceae family. Various species of the Ferulago genus have antioxidant, anticholinesterase, cytotoxic, and antiproliferative effects. In this study, the essential oil of F. bernardii was extracted using the Clevenger apparatus. The essential oil compounds were identified using GC-MS/FID. The interaction between the essential oil and DNA strands was evaluated through spectrophotometric titration. The molecular mechanism of the interaction between the main components of the essential oil and different DNA strands was assessed using molecular dynamics simulation. Based on the results, 92.03±1.20 % of the essential oil consisted of α-pinene. Therefore, the essential oil could serve as a suitable source of α-pinene. α-pinene is a monoterpene hydrocarbon that has various effects, including anti-inflammatory, antioxidant, antimicrobial, and antitumor properties. The binding constant of the essential oil to DNA strands (Ka ) was determined to be 5.40±0.47×10-3  M-1 . Molecular dynamics simulation demonstrated that α-pinene could interact with AT and CG rich DNA strands and indirectly stabilize G-Quadruplex. Given the different applications for α-pinene and its high percentage in the essential oil, it is suggested that researchers pay more attention to F. bernardii in the pharmaceutical, cosmetic, and food industries.


Assuntos
Apiaceae , Óleos Voláteis , Antioxidantes/farmacologia , Antioxidantes/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Apiaceae/química , DNA
17.
Chin J Integr Med ; 29(11): 1033-1044, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37733271

RESUMO

Saposhnikovia divaricata (Turcz.) Schischk (S. divaricata, Fangfeng) is a herb in the Apiaceae family, and its root has been used since the Western Han Dynasty (202 B.C.). Chromones and coumarins are the pharmacologically active substances in S. divaricata. Modern phytochemical and pharmacological studies have demonstrated their antipyretic, analgesic, anti-inflammatory, antioxidant, anti-tumor, and anticoagulant activities. Technological and analytical strategy theory advancements have yielded novel results; however, most investigations have been limited to the main active substances-chromones and coumarins. Hence, we reviewed studies related to the chemical composition and pharmacological activity of S. divaricata, analyzed the developing trends and challenges, and proposed that research should focus on components' synergistic effects. We also suggested that, the structure-effect relationship should be prioritized in advanced research.


Assuntos
Apiaceae , Medicamentos de Ervas Chinesas , Medicamentos de Ervas Chinesas/farmacologia , Cumarínicos/farmacologia , Apiaceae/química , Cromonas
18.
Fitoterapia ; 170: 105647, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37562490

RESUMO

Oliveria decumbens Vent., an annual herb resistant to harsh environmental conditions, is an aromatic medicinal plant of the Apiaceae family. O. decumbens has numerous pharmacological, food and feed, and cosmetic applications. This species is endemic to Iran, Iraq, and Turkey. Published literature, available until 30 November 2022 on the morphology, phytochemistry, and bioactivity of O. decumbens, has been reviewed, and appraised for the potential therapeutic potential of this species, utilizing the databases, Web of Science, Google Scholar, PubMed, and Dictionary of Natural Products. The search term used was O. decumbens. Some manuscripts were issued on the chemical components of O. decumbens essential oil (EO) and various extracts. The EO of O. decumbens was evaluated for its chemical composition and medicinal potential against various diseases. Thymol and carvacrol constituted the primary oxygenated monoterpenes detected in substantial amounts within the EO. Additionally, diverse metabolites of O. decumbens were examined for their bactericidal, antioxidant, larvicidal, and immunomodulatory effects. This review article discusses morphology, phenology, and geographical distribution of O. decumbens and presents a critical appraisal of its phytochemistry and therapeutic potential as documented in the published literature.


Assuntos
Apiaceae , Óleos Voláteis , Plantas Medicinais , Apiaceae/química , Estrutura Molecular , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Timol , Plantas Medicinais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Compostos Fitoquímicos/farmacologia , Etnofarmacologia
19.
Pharm Biol ; 61(1): 1030-1040, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37409739

RESUMO

CONTEXT: Sea fennel (Crithmum maritimum L. [Apiaceae]) is an aromatic herb rich in bioactive molecules, such as polyphenols, with potential positive effects on human health. OBJECTIVE: This study aimed at the characterization of sea fennel secondary metabolites, focusing on the phenolic fraction. MATERIALS AND METHODS: Samples of whole sprouts, sole leaves and sole stems were subjected to accelerated solvent extraction with methanol, and the resulting extracts were analyzed by high­performance thin­layer chromatography, high-performance liquid chromatography, and liquid chromatography coupled with diode array detection and high-resolution mass spectrometry (LC-DAD-HRMS). RESULTS: HPTLC and HPLC analyses of sea fennel extracts showed similar chromatographic profiles among the tested samples, and the prevalence of chlorogenic acid within the phenolic fraction was verified. Ten hydroxycinnamic acids, including neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, isochlorogenic acid B, isochlorogenic acid A and isochlorogenic acid C, 11 flavonoid glycosides, e.g., rutin, hyperoside, isoquercitrin, two triterpene saponins and two hydroxylated fatty acids, were detected and annotated via liquid chromatography coupled with diode array detection and high-resolution mass spectrometry. DISCUSSION AND CONCLUSIONS: The use of accelerated solvent extraction and LC-DAD-HRMS for the characterization of sea fennel secondary metabolites allowed the annotation of seven compounds newly detected in sea fennel, including triterpene saponins and hydroxylated fatty acids.


Assuntos
Apiaceae , Foeniculum , Saponinas , Triterpenos , Humanos , Foeniculum/química , Ácido Clorogênico , Apiaceae/química , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão , Triterpenos/análise , Solventes
20.
Sci Rep ; 13(1): 12390, 2023 07 31.
Artigo em Inglês | MEDLINE | ID: mdl-37524766

RESUMO

Despite the availability of numerous reports on the discovery of medicinal plant compounds and their properties, one may encounter contradictory results released by these reports at the level of plant families and even within species. To establish an accurate perspective of the Apiaceae family, this study examined the fruit essential oil and methanolic extract of wild and common species of this family. According to the measurement of the antioxidant property in the methanolic extract of the fruits using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, Ferula gummosa, Pimpinella anisum and Cuminum cyminum have high power in inhibiting free radicals. However, Bunium persicum had the strongest DPPH radicals inhibitory potential among all essential oils. The results of antimicrobial tests and their classification analysis showed that C. cyminum and B. persicum fruit essential oil with a high amount of cuminaldehyde had the most antibacterial properties. At the same time, the antifungal properties of H. persicum essential oil (rich in aliphatic ester) were stronger than those of the all the studied plants. Also, the essential oils of F. gummosa and Kelussia odoratissima had favourable antimicrobial properties compared to other studied plants. The investigation of the bacterial structure by scanning electron microscope confirmed the effect of the applied essential oils dose and their antibacterial potential. In general, for the first time, this paper determined the biological values of the fruit essential oil of some wild plants, such as K. odoratissima and H. persicum. Besides, in vitro examination and the mathematical models provided a suitable classification, which makes a comprehensive view in terms of the properties of the Apiaceae family.


Assuntos
Anti-Infecciosos , Apiaceae , Óleos Voláteis , Apiaceae/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Anti-Infecciosos/farmacologia , Antibacterianos/farmacologia
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