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1.
BMC Plant Biol ; 24(1): 483, 2024 May 31.
Artigo em Inglês | MEDLINE | ID: mdl-38822252

RESUMO

BACKGROUND: Zataria multiflora Boiss. is a medicinal and aromatic plant from the Lamiaceae family. It is extensively used in Iranian traditional medicine, mostly as a replacement for Thyme species. This study was focused on the analysis of chemical composition and the distribution and types of trichomes of Z. multiflora grown under different conditions. Equilibrium headspace analysis in combination with GC-FID-MS was used to identify volatile compounds released by aerial parts of Z. multiflora in development stages of 50 and 100% flowering under normal and drought-stress conditions. RESULTS: The main constituents were p-cymene (20.06-27.40%), γ-terpinene (12.44-16.93%), and α-pinene (6.91-16.58%) and thymol (8.52-9.99%). The highest content of p-cymene (27.40%) and thymol (9.99%) was observed in the 50% flowering stage at the 90% field capacity, while the maximum γ-terpinene (16.93%) content was recorded in the 100% flowering stage under normal conditions. Using the SEM method, it was found that peltate glandular and non-glandular trichomes are distributed on the surface of the leaf, stem, and outer side of the calyx. However, capitate trichomes only are detected on the stem and calyx in the 100% flowering and beginning of blooming stages, respectively. The type and structure of trichomes do not vary in different development stages, but they differ in density. The highest number of leaf peltate glandular trichomes was observed in the vegetative and beginning of blooming stages at 50% and 90% field capacity, respectively. Non-glandular trichomes of the stem were observed with high density in both normal and stress conditions, which are more densely in 90% field capacity. CONCLUSIONS: Since this plant has strong potential to be used in the food and pharmacological industries, this study provides valuable information for its cultivation and harvesting at specific phenological stages, depending on desired compounds and their concentrations.


Assuntos
Lamiaceae , Tricomas , Tricomas/crescimento & desenvolvimento , Tricomas/metabolismo , Lamiaceae/crescimento & desenvolvimento , Lamiaceae/metabolismo , Lamiaceae/fisiologia , Lamiaceae/química , Secas , Compostos Orgânicos Voláteis/metabolismo , Compostos Orgânicos Voláteis/análise , Estresse Fisiológico , Monoterpenos Cicloexânicos/metabolismo , Cimenos/metabolismo , Monoterpenos/metabolismo , Monoterpenos Bicíclicos/metabolismo , Timol/metabolismo
2.
Org Biomol Chem ; 22(15): 3019-3024, 2024 04 17.
Artigo em Inglês | MEDLINE | ID: mdl-38530279

RESUMO

An unusual pyridine-containing sesterterpenoid, leucosceptrodine (1), and five new nor-leucosceptrane sesterterpenoids, including bisnor- (C23, 2), tetranor- (C21, 3) and pentanor- (C20, 4-6) skeletons, were isolated from the leaves of Tibetan Leucosceptrum canum. Their structures including their absolute configurations were determined by extensive spectroscopic analyses and quantum chemical calculations. A single crystal of one epimer (5) was crystallized from a pair of inseparable epimers, and its structure including its absolute configuration was determined by X-ray crystallographic analysis. The immunosuppressive activities of compounds 1-4 with different potencies were evaluated by inhibiting the secretion of cytokines TNF-α and IL-6 in LPS-induced RAW264.7 macrophages.


Assuntos
Lamiaceae , Sesterterpenos , Sesterterpenos/química , Tibet , Lamiaceae/química , Cristalografia por Raios X , Piridinas/farmacologia , Estrutura Molecular
3.
Cell Biochem Funct ; 42(5): e4084, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38963282

RESUMO

Safe chemicals for drug withdrawal can be extracted from natural sources. This study investigates the effects of clonidine and Thymbra spicata extract (TSE) on mice suffering from morphine withdrawal syndrome. Thymol, which is the active constituent in TSE, was also tested. A total of 90 mice were divided into nine groups. Group 1 was the control group, while Group 2 was given only morphine, and Group 3 received morphine and 0.2 mg/kg of clonidine. Groups 4-6 were given morphine along with 100, 200, and 300 mg/kg of TSE, respectively. Groups 7-9 received morphine plus 30, 60, and 90 mg/kg of Thymol, respectively, for 7 days. An oral naloxone challenge of 3 mg/kg was used to induce withdrawal syndrome in all groups. Improvement of liver enzyme levels (aspartate aminotransferase, alkaline phosphatase, and alanine transaminase) (p < .01) and behavioral responses (frequencies of jumping, frequencies of two-legged standing, Straub tail reaction) (p < .01) were significantly observed in the groups receiving TSE and Thymol (Groups 4-9) compared to Group 2. Additionally, antioxidant activity in these groups was improved compared to Group 2. Nitric oxide significantly decreased in Groups 4 and 6 compared to Groups 2 and 3 (p < .01). Superoxide dismutase increased dramatically in Groups 5, 8, and 9 compared to Groups 2 and 3 (p < .01). Groups 5-9 were significantly different from Group 2 in terms of malondialdehyde levels (p < .01). Certain doses of TSE and Thymol were found to alleviate the narcotics withdrawal symptoms. This similar effect to clonidine can pave the way for their administration in humans.


Assuntos
Antioxidantes , Fígado , Morfina , Extratos Vegetais , Síndrome de Abstinência a Substâncias , Timol , Animais , Síndrome de Abstinência a Substâncias/tratamento farmacológico , Síndrome de Abstinência a Substâncias/metabolismo , Camundongos , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Timol/farmacologia , Timol/uso terapêutico , Antioxidantes/farmacologia , Fígado/efeitos dos fármacos , Fígado/metabolismo , Morfina/farmacologia , Masculino , Comportamento Animal/efeitos dos fármacos , Clonidina/farmacologia , Clonidina/uso terapêutico , Lamiaceae/química , Óxido Nítrico/metabolismo
4.
Luminescence ; 39(8): e4848, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-39092486

RESUMO

Herein, luminous blue carbon quantum dots (CDs) employing Anisomeles indica (Catmint) were reported with imaging, self-targeting, and therapeutic effects on triple-negative breast cancer (TNBC, MDA-MB-231) cells. The salient features of CDs generated from catmint are as follows: i) optical studies confirm CDs with excitation-dependent emission; ii) high-throughput characterization authenticates the formation of CDs with near-spherical shape with diameter ranging between 5 and 15 nm; iii) CDs induce cytotoxicity (3.22 ± 0.64 µg/ml) in triple-negative breast cancer (TNBC, MDA-MB-231) cells; iv) fluorescence microscopy demonstrates that CDs promote apoptosis by increasing reactive oxygen species (ROS) and decreasing mitochondrial membrane potential; v) CDs significantly up-regulate pro-apoptotic gene expression levels such as caspases-8/9/3. Finally, our work demonstrates that catmint-derived CDs are prospective nanotheranostics that augment cancer targeting and imaging.


Assuntos
Apoptose , Carbono , Pontos Quânticos , Transdução de Sinais , Neoplasias de Mama Triplo Negativas , Pontos Quânticos/química , Humanos , Apoptose/efeitos dos fármacos , Neoplasias de Mama Triplo Negativas/metabolismo , Neoplasias de Mama Triplo Negativas/patologia , Neoplasias de Mama Triplo Negativas/tratamento farmacológico , Carbono/química , Carbono/farmacologia , Transdução de Sinais/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Lamiaceae/química , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Antineoplásicos/farmacologia , Antineoplásicos/química
5.
Pestic Biochem Physiol ; 202: 105970, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38879314

RESUMO

This study aimed to develop a relatively natural and safe botanical insecticide for controlling the storage pest Tribolium castaneum in the egg and pupal stages. It examined how Elsholtzia densa Benth. essential oil (EO) and its primary components, ß-caryophyllene and limonene, affected T. castaneum eggs and pupae through contact and fumigation. Among th, the contact activities of ß-caryophyllene against T. castaneum eggs and pupae are LD50 (median lethal dose, 50%) = 0.156 mg/cm2 and ED50 (median effective dose, 50%) = 16.35 mg/pupa respectively. The study also investigated the effect of ß-caryophyllene and limonene on T. castaneum eggs and pupae through synergistic contact and fumigation. When the mixing ratio of ß-caryophyllene and limonene was 7:1, the LD50 value of contact activity against T. castaneum eggs was reduced to 0.100 mg/cm2, displaying an obvious synergistic effect. Experiments were conducted to investigate the antitoxic effect of ß-caryophyllene on T. castaneum eggs and pupae, as well as its effects on the enzymatic activity of acetylcholinesterase, succinate dehydrogenase, glutathione S-transferase and carboxylesterase in T. castaneum pupae. Finally, the molecular docking techniques were employed to confirm the aforementioned effects on enzyme function. The findings of this study might help improve storage pest control with T. castaneum and create eco-friendly insecticides using E. densa EO, ß-caryophyllene, and limonene.


Assuntos
Inseticidas , Lamiaceae , Óleos Voláteis , Pupa , Tribolium , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Tribolium/efeitos dos fármacos , Lamiaceae/química , Inseticidas/farmacologia , Inseticidas/química , Pupa/efeitos dos fármacos , Óvulo/efeitos dos fármacos , Limoneno/farmacologia , Sesquiterpenos Policíclicos/farmacologia , Sesquiterpenos Policíclicos/química
6.
Molecules ; 29(9)2024 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-38731415

RESUMO

Investigations have shown that storage bugs seriously harm grains during storage. In the interim, essential oils (EOs) have been proven to be a good botanical pesticide. The anti-Lasioderma serricorne properties of Elsholtzia ciliata essential oil, which was obtained by steam distillation, were evaluated using DL-limonene, carvone, and their two optical isomer components using contact, repelling, and fumigation techniques. Simultaneously, the fumigation, contact, and repellent activities of carvone and its two optical isomers mixed with DL-limonene against L. serruricorne were evaluated. The results showed that E. ciliata, its main components (R-carvone, DL-limonene), and S-carvone exhibited both fumigations (LC50 = 14.47, 4.42, 20.9 and 3.78 mg/L) and contact (LD50 = 7.31, 4.03, 28.62 and 5.63 µg/adult) activity against L.serricorne. A binary mixture (1:1) of R-carvone and DL-limonene displayed an obvious synergistic effect. A binary mixture (1:1) of carvone and its two optical isomers exhibited an obvious synergistic effect, too. Furthermore, the repellent activity of the EO, carvone, and its two optical isomers, DL-limonene, and a combination of them varied. To stop insect damage during storage, E. ciliata and its components can be utilized as bio-insecticides.


Assuntos
Inseticidas , Lamiaceae , Óleos Voláteis , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Lamiaceae/química , Animais , Inseticidas/química , Inseticidas/farmacologia , Limoneno/química , Limoneno/farmacologia , Repelentes de Insetos/química , Repelentes de Insetos/farmacologia , Monoterpenos Cicloexânicos/química , Monoterpenos Cicloexânicos/farmacologia , Sinergismo Farmacológico , Fumigação
7.
Inflammopharmacology ; 32(4): 2477-2491, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38717557

RESUMO

Micromeria biflora (M.B) Benth has proven anti-inflammatory efficacy, thereby, the goal of the current investigation was to assess the anti-arthritic potential of M.B ethanolic extract and fractions as well as to investigate the likely mechanism of action. The effectiveness of M.B against acute arthritic manifestations was assessed using an arthritic model prompted by formaldehyde, whereas a chronic model was developed using an adjuvant called Complete Freund's in Sprague-Dawley rats. Weekly evaluations were conducted for parameters involving paw volume, body weight, and arthritic score; at the completion of the CFA model, hematological, biochemical and oxidative stress parameters as well as the level of various mediators (PGE2, IL-1ß, TNFα, IL6, MMP2, 3, 9, VEGF, NF-ĸB, IL-10, and IL-4) were evaluated. The results demonstrated the plant's ability to treat arthritis by showing a significant decrease in paw volume, arthritic score, and histological characteristics. The levels of NF-ĸB, MMP2, 3, 9, IL6, IL1ß, TNFα, and VEGF were all significantly reduced after treatment with plant extract and fractions. Plant extract and its fractions substantially preserved body weight loss, oxidative stress markers and levels of IL-4 and 1L-10. PGE2 levels were also shown to be reduced in the treatment groups, supporting the M.B immunomodulatory ability. Hematological and biochemical indicators were also normalized after M.B administration. Outcomes of the study validated the anti-arthritic and immunomodulatory attributes of M.B probably through modulating oxidative stress, inflammatory, pro-inflammatory and anti-inflammatory biomarkers.


Assuntos
Anti-Inflamatórios , Artrite Experimental , Citocinas , Estresse Oxidativo , Extratos Vegetais , Ratos Sprague-Dawley , Animais , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Ratos , Citocinas/metabolismo , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Masculino , Artrite Experimental/tratamento farmacológico , Metaloproteases , Agentes de Imunomodulação/farmacologia , Agentes de Imunomodulação/isolamento & purificação , Lamiaceae/química , Inflamação/tratamento farmacológico , Feminino , Mediadores da Inflamação/metabolismo , Mediadores da Inflamação/antagonistas & inibidores
8.
Molecules ; 29(12)2024 Jun 13.
Artigo em Inglês | MEDLINE | ID: mdl-38930892

RESUMO

The Lamiaceae family, which includes several well-known aromatic plants, is scientifically relevant due to its essential oils (EOs). In this work, four EOs from Mediterranean species, namely Origanum vulgare L., Rosmarinus officinalis L., Salvia officinalis L., and Thymus vulgaris L., were evaluated for their volatile profiles and the biological activity in vitro to assess their potential use in the food and cosmetic sector. GC/MS analysis revealed dominant compounds, such as carvacrol, thymol, and eucalyptol. Regarding biological action, the samples exhibited antioxidant, cytotoxic, anti-inflammatory, antimicrobial, and antifungal activities, with O. vulgare and T. officinalis standing out. T. vulgaris showed the lowest EC50 in the reducing power assay, and O. vulgare had the lowest EC50 in the DPPH assay. Most EOs also displayed excellent anti-inflammatory responses and antifungal properties, with O. vulgare and T. vulgaris also demonstrating antibacterial activity. All EOs from Mediterranean species showed cytotoxicity against tumoral cell lines. Overall, the selected EOs stood out for their interesting bioactivities, with the obtained results underscoring their potential as natural preservatives and bioactive agents in various industrial applications, including food, pharmaceuticals, and cosmetics.


Assuntos
Antioxidantes , Lamiaceae , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Lamiaceae/química , Antioxidantes/farmacologia , Antioxidantes/química , Humanos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Cromatografia Gasosa-Espectrometria de Massas , Origanum/química , Salvia officinalis/química , Linhagem Celular Tumoral , Thymus (Planta)/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Plantas Comestíveis/química , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Timol/farmacologia , Timol/química , Testes de Sensibilidade Microbiana , Cimenos
9.
Trop Anim Health Prod ; 56(6): 195, 2024 Jul 04.
Artigo em Inglês | MEDLINE | ID: mdl-38963478

RESUMO

This experiment aimed to assess the regulatory effects of treatment with Balanites aegyptiaca fruit ethanol extract (BA-EE) on oxidant/antioxidant status, anti-inflammatory cytokines, and cell apoptosis gene expression in the abomasum of Haemonchus contortus-infected goats. Twenty goat kids were assigned randomly to four equal groups: (G1) infected-untreated, (G2) uninfected-BA-EE-treated, (G3) infected-albendazole-treated, (G4) infected-BA-EE-treated. Each goat in (G1), (G3), and (G4) was orally infected with 10,000 infective third-stage larvae. In the fifth week postinfection, single doses of albendazole (5 mg/kg.BW) and BA-EE (9 g/kg.BW) were given orally. In the ninth week postinfection, the animals were slaughtered to obtain abomasum specimens. The following oxidant/antioxidant markers were determined: malondialdehyde (MDA), glutathione (GSH), glutathione-S-transferase (GST), superoxide dismutase (SOD), catalase (CAT). The mRNA gene expression of cytokines (IL-3, IL-6, IL-10, TNF-α) and cell apoptosis markers (Bax, Bcl-2) were estimated. (G1) showed significantly reduced GSH content and GST and SOD activities but a markedly increased MDA level. (G3) and (G4) revealed a markedly lower MDA level with pronouncedly elevated GSH, SOD, and GST levels. The antioxidant properties of BA-EE were superior to those of albendazole. The mRNA gene expressions of IL-3, IL-6, IL-10, TNF-α, and Bax-2 were upregulated in (G1) but downregulated in (G3) and (G4). Bcl-2 and Bcl-2/Bax ratio expression followed a reverse course in the infected and both treated groups. We conclude that BA-EE treatment has a protective role in the abomasum of H. contortus-infected goats. This could be attributed to its antioxidant properties and ability to reduce pro-inflammatory cytokines and cell apoptosis.


Assuntos
Abomaso , Antioxidantes , Apoptose , Citocinas , Doenças das Cabras , Cabras , Hemoncose , Haemonchus , Extratos Vegetais , Animais , Doenças das Cabras/parasitologia , Doenças das Cabras/tratamento farmacológico , Extratos Vegetais/farmacologia , Extratos Vegetais/administração & dosagem , Citocinas/metabolismo , Citocinas/genética , Apoptose/efeitos dos fármacos , Hemoncose/veterinária , Hemoncose/parasitologia , Haemonchus/efeitos dos fármacos , Abomaso/parasitologia , Antioxidantes/metabolismo , Anti-Helmínticos/farmacologia , Anti-Helmínticos/administração & dosagem , Distribuição Aleatória , Etanol , Expressão Gênica/efeitos dos fármacos , Albendazol/farmacologia , Albendazol/administração & dosagem , Frutas/química , Lamiaceae/química , Masculino
10.
Zhongguo Zhong Yao Za Zhi ; 49(11): 2940-2946, 2024 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-39041153

RESUMO

The chemical constituents from Leucas ciliata belonging to Leucas genus in Lamiaceae were systematically explored by silica gel column chromatography, ODS column chromatography, Sephadex LH-20 gel column chromatography, and preparative high performance liquid chromatography, and seventeen phenolic acids were isolated. The chemical structures of the compounds were identified by their physicochemical properties, spectroscopic data, and literature. They were 4-hydroxyphenethyl ethyl succinate(1), 4-hydroxyphenethyl methyl succinate(2), 2-(4-hydroxyphenyl) ethyl acetate(3), p-hydroxyphenylethyl anisate(4), cassia cis-trans diphenylpropanoid(5), p-coumaric acid(6), 3,4-dihydroxybenzenepropionic acid methyl ester(7), caffeic acid(8), trans-p-hydroxyl ethyl cinnamate(9), methyl p-hydroxybenzeneacetate(10), 4-hydroxyphenethyl alcohol(11), syringic acid(12), vanillin(13), protocatechuic acid(14), salicylic acid(15), p-hydroxybenzaldehyde(16), and diorcinol(17). Among them, compound 1 was new, and compounds 2-10, 12, 14, and 16-17 were isolated from the plants belonging to Leucas genus for the first time. All compounds were obtained from L. ciliata for the first time. The anti-inflammatory activity of compounds 1-17 on NO production in lipopolysaccharide(LPS)-induced mouse leukemia cells of monocyte macrophage(RAW264. 7) cells was evaluated. The results showed that compounds 5, 7, and 9 exhibited significant anti-inflammatory activity, with IC50values of(10. 14±0. 36)-(21. 17±0. 11) µmol·L~(-1).


Assuntos
Anti-Inflamatórios , Hidroxibenzoatos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Animais , Camundongos , Células RAW 264.7 , Lamiaceae/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Estrutura Molecular , Óxido Nítrico , Macrófagos/efeitos dos fármacos
11.
Zhongguo Zhong Yao Za Zhi ; 49(13): 3505-3514, 2024 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-39041122

RESUMO

The synergistic effect and compatibility structure of active anti-inflammatory ingredients(iridoid glycosides: shanzhiside methylester and 8-O-acetylshanzhiside methyl ester, flavonoid glycoside: luteoloside, and phenylethanoid glycoside: forsythoside B) from Lamiophlomis rotata were explored based on network pharmacology and component structure theory. In network pharmacology, CTD, SwisseTargetPrediction, and PharmMapper databases were used to collect and screen the targets of all active ingredients. The inflammation-related targets were obtained from CTD and GeneCards databases. The core targets were obtained by Venny 2.1.0, STRING, and Cytoscape 3.9.1. Core targets were annotated by the GO function and enriched by the KEGG pathway based on the DAVID database. In terms of component structure, based on a uniform design method and xylene-induced ear swelling model in mice, tumor necrosis factor-α and interleukin-6 were taken as the dependent variables, and the compatibility relationship among anti-inflammatory ingredients from L. rotata was explored through the quadratic polynomial stepwise regression. In addition, in vivo pharmacological experiments were conducted to verify the results. A network pharmacology study showed that compared with a single ingredient, the combined action of the three ingredients can synergistically exert anti-inflammatory effects through more biological processes, pathways, and targets. Component structure study showed that the optimal structural ratio of shanzhiside methylester and 8-O-acetylshanzhiside methyl ester in the iridoid glycoside ingredient was 1.21∶1. The optimal structural ratio among the three types of ingredients(iridoid glycosides∶phenylethanol glycoside∶flavonoid glycoside) was 4.8∶1.6∶1. In conclusion, each anti-inflammatory ingredient from L. rotata can work synergistically, and there is an optimal compatibility ratio relationship among these ingredients. This work provides a new experimental basis for the intrinsic quality control of L. rotata.


Assuntos
Anti-Inflamatórios , Medicamentos de Ervas Chinesas , Farmacologia em Rede , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Animais , Camundongos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Masculino , Lamiaceae/química , Fator de Necrose Tumoral alfa/metabolismo , Fator de Necrose Tumoral alfa/imunologia , Sinergismo Farmacológico , Interleucina-6/imunologia , Interleucina-6/metabolismo , Interleucina-6/genética
12.
J Nat Prod ; 86(11): 2468-2473, 2023 11 24.
Artigo em Inglês | MEDLINE | ID: mdl-37939268

RESUMO

Three unusual sesterterpenoids featuring unprecedented rearranged colquhounane (C25) and tetranorcolquhounane (C21) frameworks, colquhounoids E (1) and F (3) and norcolquhounoid F (2), were isolated from a Lamiaceae medicinal plant Colquhounia coccinea var. mollis. Their structures were elucidated by spectroscopic analysis and quantum chemical calculations. A biomimetic inspired regioselective cyclopropane cleavage was achieved under acidic conditions. The immunosuppressive activities of these new sesterterpenoids were also evaluated.


Assuntos
Lamiaceae , Plantas Medicinais , Análise Espectral , Lamiaceae/química , Estrutura Molecular
13.
Chem Biodivers ; 20(8): e202300785, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37344399

RESUMO

Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives (1-4), named as elsholblanosides A-D, respectively, together with 11 known compounds (5-15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1-4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33 µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.9 µM.


Assuntos
Ácidos Cicloexanocarboxílicos , Lamiaceae , Animais , Camundongos , Lipopolissacarídeos/farmacologia , Lamiaceae/química , Células RAW 264.7 , Estrutura Molecular
14.
Chem Biodivers ; 20(4): e202201037, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-36907662

RESUMO

This study describes the isolation and identification of two novel phenylethanoid glycosides, aureoglanduloside A (1) and aureoglanduloside B (2), as well as a newly discovered diterpene glycoside, aureoglanduloside C (29). Additionally, 31 known compounds were isolated from the n-butyl alcohol (BuOH) soluble fraction of Caryopteris aureoglandulosa whole dried plants. Their structures were characterized using various spectroscopic techniques and high-resolution electrospray ionization mass spectroscopy (HR-ESI-MS). Furthermore, the neuroprotective effects of all phenylethanoid glycosides were evaluated. Specifically, compounds 2 and 10-12 exhibited the ability to promote the phagocytosis of myelin by microglia, and compounds 2, 10-11, and 24 showed the ability to promote the phagocytosis of myelin by astrocytes.


Assuntos
Glicosídeos , Lamiaceae , Glicosídeos/farmacologia , Glicosídeos/química , Lamiaceae/química , Espectrometria de Massas por Ionização por Electrospray
15.
Chem Biodivers ; 20(6): e202300448, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-37218541

RESUMO

Two previously undescribed compounds (1 and 2) were isolated from Clinopodium polycephalum, a medicinal plant distributed in southwestern and eastern China. Their structures were elucidated using MS analyses and extensive 2D-homo and heteronuclear NMR data interpretations. Both compounds 1 and 2 could significantly shorten APTT and PT, and their procoagulant effect was comparable to that of positive drugs. At the same time, compound 2 had certain antioxidant activity (IC50 value of 2.25±0.05 µM in ABTS assay).


Assuntos
Lamiaceae , Plantas Medicinais , Anticoagulantes/farmacologia , Lamiaceae/química , Antioxidantes/farmacologia , Antioxidantes/química , China , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Estrutura Molecular
16.
Chem Biodivers ; 20(4): e202300027, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-36891984

RESUMO

Cyclotrichium niveum (Boiss.) Manden & Scheng belonging to the Lamiaceae family, which is an endemic species in the eastern Anatolian region of Turkey, has an important place in terms of ethno-botany. The phytochemical composition of the plant, inhibition of acetylcholinesterase (AChE) (which hydrolyzes the neurotransmitter acetylcholine), inhibition of paraoxonase for antiatherosclerotic activity (hPON 1) (which detoxifies organophosphates), and antioxidant capacity were all investigated in this study. Phytochemical content was determined by LC/MS/MS, and enzyme inhibition and antioxidant capacity studies were determined by spectrophotometer. Antioxidant capacity of C. niveum extracts (methanol, hexane, and water) was determined by applying ABTS⋅+ , DPPH⋅, FRAP, and CUPRAC methods. Both the water and the methanol extracts of the C. niveum exhibited significant inhibition on the AChE (IC50 value for methanol and water extract 0.114±0.14 mg/mL (R2:0.997) and 0.178±0.12 mg/mL (R2 : 0.994), respectively). In contrast, the methanol and water extracts of the C. niveum did not exhibit the inhibition effect on hPON 1. The highest activity for ABTS⋅+ was 66.53 % in the water extract, and DPPH⋅ was 55.03 % in the methanol extract. In the metal-reducing power assay, the absorbance was 0.168±0.04 for FRAP water extract and 0.621±0.01 for CUPRAC methanol extract. According to LC/MS/MS analyses, hydroxybenzoic acid, salicylic acid, syringic acid, acetohydroxamic acid and luteolin determined in the plant extract. As a consequence, C. niveum which has antioxidant, anti-atherogenic and anti-neurodegenerative properties has the potential to be used as a natural medication instead of synthetic drugs used in Alzheimer's patients.


Assuntos
Antioxidantes , Inibidores Enzimáticos , Lamiaceae , Humanos , Acetilcolinesterase , Antioxidantes/química , Lamiaceae/química , Lamiaceae/enzimologia , Metanol , Fenóis/química , Compostos Fitoquímicos , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Espectrometria de Massas em Tandem , Água , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia
17.
Phytochem Anal ; 34(6): 661-679, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37387322

RESUMO

INTRODUCTION: The endemic species Nepeta cyrenaica Quézel & Zaffran, native to northeastern Libya, is valued as an important honey-bearing plant. OBJECTIVES: This study was aimed to examine the micromorphology, phytochemistry, and bioactivity of in vitro-propagated N. cyrenaica for the first time. MATERIALS AND METHODS: The leaf indumentum was examined using light and scanning electron microscopy and further characterised for histochemistry. The chemical composition of essential oil (EO) was performed using GC-MS analysis, while dichloromethane (DCM), methanol (ME), ethanol (ET), and aqueous (AQ) extracts were analysed using qualitative and quantitative LC/MS analyses. The antioxidant activities of EO and extracts were assessed using three parallel assays, while enzyme-inhibiting effects were evaluated against four enzymes. RESULTS: The leaves bear various types of glandular trichomes, with lipophilic secretion predominating. The main EO component of EO was 1,8-cineole. A considerable number of phenolics and iridoids were tentatively identified in the ME extract. Quantitative LC/MS analysis confirmed that ferulic acid, rosmarinic acid, and epigallocatechin gallate were present in the highest amount in the extracts, in which three iridoids were also quantified. Although the ME extract contained the highest amount of polyphenolics and iridoids, the DCM extract showed the best overall biological potential. Additionally, EO exerted the strongest acetylcholinesterase and tyrosinase inhibition. CONCLUSION: This study demonstrated that the endemic N. cyrenaica can be efficiently grown under in vitro conditions, where it develops various glandular trichomes that are thought to secrete and/or accumulate bioactive compounds with valuable medicinal potential.


Assuntos
Lamiaceae , Nepeta , Óleos Voláteis , Lamiaceae/química , Nepeta/química , Acetilcolinesterase , Óleos Voláteis/química , Antioxidantes/farmacologia , Antioxidantes/análise , Extratos Vegetais/química , Iridoides , Folhas de Planta/química
18.
Int J Mol Sci ; 24(14)2023 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-37511428

RESUMO

Oxidative stress is the most critical factor in multiple functional disorders' development, and natural antioxidants could protect the human body against it. Our study aims to investigate the polyphenol content of four extracts of two medicinal plants (Rosmarinus officinalis L. and Thymus vulgaris L.) and analyze the correlation with their antioxidant activity. The research was carried out on extracts of rosemary and thyme obtained from species cultivated together in plant communities. Both were compared with extracts from species cultivated in individual crops (control crops). Their polyphenols were determined by spectrophotometric methods (dosage of flavones, phenol carboxylic acids, and total polyphenols) and chromatography (UHPLC-MS and FT-ICR MS). Triterpenic acids were also quantified, having a higher concentration in the thyme extract from the culture. The antioxidant activity of the dry extracts was evaluated in vitro (DPPH, ABTS, and FRAP) and in silico (prediction of interactions with BACH1/BACH2 transcription factors). The concentrations of polyphenols are higher in the extracts obtained from the sources collected from the common crops. These observations were also validated following the chromatographic analysis for some compounds. Statistically significant differences in the increase in the antioxidant effect were observed for the extracts from the common batches compared to those from the individual ones. Following the Pearson analysis, the IC50 values for each plant extract were strongly correlated with the concentration of active phytoconstituents. Molecular docking studies revealed that quercetin could bind to BTB domains of BACH1 and BACH2 transcription factors, likely translating into increased antioxidant enzyme expression. Future studies must validate the in silico findings and further investigate phytosociological cultivation's effects.


Assuntos
Lamiaceae , Rosmarinus , Thymus (Planta) , Humanos , Antioxidantes/química , Thymus (Planta)/química , Rosmarinus/química , Lamiaceae/química , Simulação de Acoplamento Molecular , Extratos Vegetais/química , Polifenóis/química , Fatores de Transcrição de Zíper de Leucina Básica
19.
Molecules ; 28(5)2023 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-36903258

RESUMO

The volatile metabolites of Salvia sclarea, Rosmarinus officinalis, Thymus serpyllum, Mentha spicata, Melissa officinalis, Origanum majorana, Mentha piperita, Ocimum basilicum and Lavandula angustifolia were determined by gas chromatography-mass spectrometry. The vapor insecticidal properties of the analyzed essential oils and their compounds were screened using Reticulitermes dabieshanensis workers. The most effective oils were S. sclarea (major constituent linalyl acetate, 65.93%), R. officinalis (1,8-cineole, 45.56%), T. serpyllum (thymol, 33.59%), M. spicata (carvone, 58.68%), M. officinalis (citronellal, 36.99%), O. majorana (1,8-cineole, 62.29%), M. piperita (menthol, 46.04%), O. basilicum (eugenol, 71.08%) and L. angustifolia (linalool, 39.58%), which exhibited LC50 values ranging from 0.036 to 1.670 µL/L. The lowest LC50 values were recorded for eugenol (0.060 µL/L), followed by thymol (0.062 µL/L), carvone (0.074 µL/L), menthol (0.242 µL/L), linalool (0.250 µL/L), citronellal (0.330 µL/L), linalyl acetate (0.712 µL/L) and 1,8-cineole (1.478 µL/L). The increased activity of esterases (ESTs) and glutathione S-transferase (GST) were observed but only alongside the decreased activity of acetylcholinesterase (AChE) in eight main components. Our results indicate that S. sclarea, R. officinalis, T. serpyllum, M. spicata, M. officinalis, O. marjorana, M. piperita, O. basilicum and L. angustifolia essential oils (EOs) and their compounds, linalyl acetate, 1,8-cineole, thymol, carvone, citronellal, menthol, eugenol and linalool could be developed as control agents against termites.


Assuntos
Lamiaceae , Óleos Voláteis , Óleos Voláteis/química , Lamiaceae/química , Timol/química , Mentol/farmacologia , Eucaliptol , Eugenol , Acetilcolinesterase , Óleos de Plantas/química
20.
Molecules ; 28(12)2023 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-37375165

RESUMO

Ironwort (Sideritis montana L.), mountain germander (Teucrium montanum L.), wall germander (Teucrium chamaedrys L.), and horehound (Marrubium peregrinum L.) are species widely distributed across Europe and are also found in North Africa and West Asia. Because of their wide distribution they express significant chemical diversity. For generations, these plants have been used as medical herbs for treating different aliments. The aim of this paper is to analyze volatile compounds of four selected species that belong to the subfamily Lamioideae, family Lamiaceae, and inspect scientifically proven biological activities and potential uses in modern phytotherapy in relation to traditional medicine. Therefore, in this research, we analyze the volatile compounds from this plants, obtained in laboratory by a Clevenger-type apparatus, followed by liquid-liquid extraction with hexane as the solvent. The identification of volatile compounds is conducted by GC-FID and GC-MS. Although these plants are poor in essential oil, the most abundant class of volatile components are mainly sesquiterpenes: germacrene D (22.6%) in ironwort, 7-epi-trans-sesquisabinene hydrate (15.8%) in mountain germander, germacrene D (31.8%) and trans-caryophyllene (19.7%) in wall germander, and trans-caryophyllene (32.4%) and trans-thujone (25.1%) in horehound. Furthermore, many studies show that, in addition to the essential oil, these plants contain phenols, flavonoids, diterpenes and diterpenoids, iridoids and their glycosides, coumarins, terpenes, and sterols, among other active compounds, which affect biological activities. The other goal of this study is to review the literature that describes the traditional use of these plants in folk medicine in regions where they grow spontaneously and compare them with scientifically confirmed activities. Therefore, a bibliographic search is conducted on Science Direct, PubMed, and Google Scholar to gather information related to the topic and recommend potential applications in modern phytotherapy. In conclusion, we can say that selected plants could be used as natural agents for promoting health, as a source of raw material in the food industry, and as supplements, as well as in the pharmaceutical industry for developing plant-based remedies for prevention and treatment of many diseases, especially cancer.


Assuntos
Diterpenos , Lamiaceae , Óleos Voláteis , Plantas Medicinais , Sideritis , Teucrium , Lamiaceae/química , Plantas Medicinais/química , Sérvia , Fitoterapia , Óleos Voláteis/química , Teucrium/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química
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