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1.
J Mass Spectrom ; 59(8): e5069, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38989730

RESUMO

Cinnamomi ramulus (CR) is a common Chinese herbal medicine with a long history. It is often used to treat exogenous wind-cold diseases in clinic, but its chemical compositions remain to be studied. In this study, CR was extracted with 75% ethanol, and UPLC-Q-Orbitrap-MS combined with data post-processing method was used to identify the chemical components in the extract. Through this technology, the components in CR can be separated and accurately identified. A total of 61 compounds were identified, including 14 simple phenylpropanoids, 3 coumarins, 5 lignans, 14 flavonoids, 10 benzoic acids, 8 organic acids, and 7 others. This study confirmed the existence of these compounds in CR and speculated the cleavage pathways of each compound, which enriched the mass spectrometry data and cleavage rules. This study can provide a reference for CR and other research.


Assuntos
Cumarínicos , Medicamentos de Ervas Chinesas , Flavonoides , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Cumarínicos/química , Cumarínicos/análise , Flavonoides/análise , Flavonoides/química , Lignanas/análise , Lignanas/química , Espectrometria de Massas/métodos , Cinnamomum/química , Espectrometria de Massas em Tandem/métodos
2.
J Mass Spectrom ; 59(8): e5075, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38989744

RESUMO

Prinsepia utilis Royle, native to the Himalayas, is esteemed in Chinese and Indian folk medicine for its diverse medicinal benefits, targeting arthritis, pain relief, bone disorders, and joint discomfort. This study examined the 25% aqueous methanol extract of P. utilis leaves using UPLC-Q-TOF-MS/MS, identifying 78 metabolites, 76 of which were reported for the first time in P. utilis. These included 64 phenolics represented by 56 flavonoids, 5 phenolic acids, 3 phenolic glycosides, 4 terpenoids, 2 lignan glycosides, and 8 other compounds, expanding the knowledge of its chemical composition. These findings lay a foundation for further research, providing insights into potential bioactive compounds and opening avenues for applications in natural product drug discovery, traditional medicine, and nutraceutical development, leveraging the plant's established traditional uses.


Assuntos
Flavonoides , Metabolômica , Extratos Vegetais , Folhas de Planta , Espectrometria de Massas em Tandem , Folhas de Planta/química , Folhas de Planta/metabolismo , Cromatografia Líquida de Alta Pressão/métodos , Metabolômica/métodos , Extratos Vegetais/química , Espectrometria de Massas em Tandem/métodos , Flavonoides/análise , Fenóis/análise , Glicosídeos/análise , Glicosídeos/metabolismo , Metaboloma , Terpenos/análise , Terpenos/metabolismo , Lignanas/análise , Lignanas/metabolismo , Hidroxibenzoatos
3.
Nutrients ; 16(10)2024 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-38794712

RESUMO

Extra virgin olive oil (EVOO) is a symbol of the Mediterranean diet, constituting its primary source of fat. The beneficial effect of EVOO is strictly related to the presence of fatty acids and polyphenols, bioactive compounds endowed with nutraceutical properties. Among EVOO polyphenols, lignans possess a steroid-like chemical structure and are part of the phytoestrogen family, which is renowned for its health properties. The natural lignans (+)-pinoresinol and 1-acetoxypinoresinol (1-AP) are commonly present in olives and in EVOO. Although (+)-pinoresinol is found in different edible plants, such as flaxseed, beans, whole-grain cereals, sesame seeds, and certain vegetables and fruit, 1-AP was exclusively identified in olives in 2000. So far, the scientific literature has extensively covered different aspects of (+)-pinoresinol, including its isolation and nutraceutical properties. In contrast, less is known about the olive lignan 1-AP. Therefore, this review aimed to comprehensively evaluate the more important aspects of 1-AP, collecting all the literature from 2016 to the present, exploring its distribution in different cultivars, analytical isolation and purification, and nutraceutical properties.


Assuntos
Suplementos Nutricionais , Lignanas , Olea , Azeite de Oliva , Lignanas/análise , Olea/química , Humanos , Azeite de Oliva/química , Frutas/química , Furanos
4.
Phytomedicine ; 129: 155625, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38692077

RESUMO

BACKGROUND: Shengmai Formula (SMF), a classic formula in treating Qi-Yin deficiency, is composed of Ginseng Radix et Rhizoma Rubra (GRR), Ophiopogon Radix (OR), and Schisandra chinensis Fructus (SC), and has been developed into various dosage forms including Shengmai Yin Oral Liquid (SMY), Shengmai Capsules (SMC), and Shengmai Injection (SMI). The pharmacological effects of compound Chinese medicine are attributed to the integration of multiple components. Yet the quality criteria of SMF are limited to monitoring schisandrol A or ginsenosides Rg1 and Re, but none for OR. Since the complexity of raw materials and preparations, establishing a economical and unified method for SMF is challenging. It is urgent to simultaneously quantify multiple components with different structures using a universal method for quality control of SMF. Charged aerosol detector (CAD) overcame the above shortcomings owing to its characteristics of high responsiveness, nondiscrimination, and low cost. PURPOSE: We aimed to establish a versatile analysis strategy using HPLC-CAD for simultaneously quantifying the structurally diverse markers in quality control of SMF from raw materials to preparations. METHOD: By optimizing the column, mobile phase, column temperature, flow rate, and CAD parameters, a HPLC-CAD method that integrated multi-component characterization, authenticity identification, transfer information of raw materials and quantitative determination of Shengmai preparations was established. RESULTS: In total 50 components from SMF were characterized (28 in GRR, 13 in SC, and 9 in OR). The differences in raw materials between species of SC and Schisandrae sphenantherae Fructus (SS), processing methods of Ginseng Radix (GR) and GRR, and locations of OR from Sichuan (ORS) and Zhejiang (ORZ) were compared. Fourteen components in 19 batches of SMY, SMC and SMI from different manufacturers were quantified, including 11 ginsenosides and 3 lignans. The multivariate statistical analysis results further suggested that Rb1, Rg1 and Ro were the main differences among Shengmai preparations. CONCLUSION: The established versatile analysis strategy based on HPLC-CAD was proven sensitive, simple, convenient, overcoming the discriminatory effect of UV detector, revealing the composition and transfer information of SMF and applicable for authentication of the ingredient herbs and improving the quality of Shengmai preparations.


Assuntos
Combinação de Medicamentos , Medicamentos de Ervas Chinesas , Controle de Qualidade , Schisandra , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Medicamentos de Ervas Chinesas/normas , Schisandra/química , Ginsenosídeos/análise , Ginsenosídeos/química , Lignanas/análise , Ciclo-Octanos/análise , Ciclo-Octanos/química , Panax/química
5.
Plant Foods Hum Nutr ; 79(2): 497-502, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38589624

RESUMO

Metabolites of the edible and medicinal plant Arctium have been shown to possess beneficial activities. The phytochemical profile of Arctium lappa is well-explored and its fruits are known to contain mainly lignans, fatty acids, and sterols. But the fruits of other Arctium species have not been thoroughly investigated. Therefore, this study compares the metabolic profiles of the fruits of A. lappa, Arctium tomentosum, and Arctium minus. Targeted metabolomics led to the putative identification of 53 metabolites in the fruit extracts, the majority of these being lignans and fatty acids. Quantification of the major lignans showed that the year of collection had a significant effect on the lignan content. Furthermore, A. lappa fruits contained lesser amounts of arctigenin but greater amounts of arctigenin glycoside than A. minus fruits. Regarding the profile of fatty acids, A. minus fruits differed from the others in the presence of linolelaidic acid.


Assuntos
Arctium , Ácidos Graxos , Frutas , Lignanas , Extratos Vegetais , Arctium/química , Frutas/química , Lignanas/análise , Ácidos Graxos/análise , Ácidos Graxos/metabolismo , Extratos Vegetais/análise , Extratos Vegetais/química , Furanos/análise , Furanos/metabolismo , Compostos Fitoquímicos/análise , Metaboloma , Metabolômica
6.
Phytochem Anal ; 35(5): 1142-1151, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38558474

RESUMO

INTRODUCTION: Gomisin is a natural dibenzo cyclooctene lignan, which is mainly derived from the family Magnoliaceae. It has anti-inflammatory, antioxidant, anti-tumor, anti-aging, and hypoglycemic effects. Gomisins play important roles as medicines, nutraceuticals, food additives, and cosmetics. OBJECTIVE: The objective of this study is to establish a micellar electrokinetic chromatography (MEKC) method for simultaneous separation and determination of seven biphenyl cyclooctene lignans (Gomisin D, E, G, H, J, N, and O) in Schisandra chinensis and its preparations. METHODS: The method was optimized by studying the effects of the main parameters on the separation. The method has been validated and successfully applied to the determination of seven Gomisins in S. chinensis and its preparations. RESULTS: In the separation system, the running buffer was composed of 20 mM Na2HPO4, 8.0 mM sodium dodecyl sulfate (SDS), 11% (v/v) methanol, and 6.0% (v/v) ethanol. A diode array detector was used with a detection wavelength of 230 nm, a separation voltage of 17 kV, and an operating temperature of 25°C. Under this condition, the seven analytes were separated at baseline within 20 min, and a good linear relationship was obtained with correlation coefficient ranging from 0.9919 to 0.9992. The limit of detection (LOD, S/N = 3) and the limit of quantification (LOQ, S/N = 10) ranged from 0.8 to 0.9 µg/mL and from 2.6 to 3.0 µg/mL, respectively. The recovery rate was between 99.1% and 102.5%. CONCLUSION: The experimental results indicated that this method is suitable for the separation and determination of seven Schisandra biphenyl cyclooctene lignan compounds in real samples. At the same time, it provides an effective reference for the quality control of S. chinensis and its preparations.


Assuntos
Cromatografia Capilar Eletrocinética Micelar , Ciclo-Octanos , Lignanas , Schisandra , Solventes , Lignanas/análise , Schisandra/química , Cromatografia Capilar Eletrocinética Micelar/métodos , Solventes/química , Ciclo-Octanos/análise , Ciclo-Octanos/química , Reprodutibilidade dos Testes , Limite de Detecção , Compostos de Bifenilo/química
7.
Molecules ; 29(8)2024 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-38675712

RESUMO

Schisandra chinensis, as a traditional Chinese herbal medicine, has clear pharmacological effects such as treating asthma, protecting nerves and blood vessels, and having anti-inflammatory properties. Although the Schisandra chinensis fruit contain multiple active components, the lignans have been widely studied as the primary pharmacologically active compound. The volatile chemical components of Schisandra chinensis include a large amount of terpenes, which have been proven to have broad pharmacological activities. However, when to harvest to ensure the highest accumulation of pharmacologically active components in Schisandra chinensis fruits is a critical issue. The Schisandra chinensis fruit trees in the resource nursery were all planted in 2019 and began bearing fruit in 2021. Their nutritional status and tree vigor remain consistently good. The content of lignans and organic acids in the fruits of Schisandra chinensis over seven different harvest periods was tested, and the results of high-performance liquid chromatography (HPLC) indicated that the lignan content was higher, at 35 mg/g, in late July, and the organic acid content was higher, at 72.34 mg/g, in early September. If lignans and organic acids are to be selected as raw materials for pharmacological development, the harvest can be carried out at this stage. Using HS-GC-IMS technology, a total of 67 volatile flavor substances were detected, and the fingerprint of the volatile flavor substances in the different picking periods was established. It was shown by the results that the content of volatile flavor substances was the highest in early August, and 16 flavor substances were selected by odor activity value (OAV). The variable importance in projection (VIP) values of 16 substances were further screened, and terpinolene was identified as the key volatile flavor substance that caused the aroma characteristics of Schisandra chinensis fruit at different harvesting periods. If the aroma component content of Schisandra chinensis fruit is planned to be used as raw material for development and utilization, then early August, when the aroma component content is higher, should be chosen as the time for harvest. This study provides a theoretical basis for the suitable harvesting time of Schisandra chinensis for different uses, and promotes the high-quality development of the Schisandra chinensis industry.


Assuntos
Frutas , Schisandra , Schisandra/química , Cromatografia Líquida de Alta Pressão/métodos , Frutas/química , Lignanas/análise , Lignanas/química , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química , Cromatografia Gasosa-Espectrometria de Massas/métodos
8.
Sci Rep ; 14(1): 8709, 2024 04 15.
Artigo em Inglês | MEDLINE | ID: mdl-38622262

RESUMO

Sect. tuberculata plant belongs to the Camellia genus and is named for the "tuberculiform protuberance on the surface of the ovary and fruit". It is a species of great ornamental value and potential medicinal value. However, little has been reported on the metabolites of C. tuberculata seeds. Therefore, this study was conducted to investigate the metabolites of C. tuberculata seeds based on UPLC/ESI-Q TRAP-MS/MS with extensively targeted metabolomics. A total of 1611 metabolites were identified, including 107 alkaloids, 276 amino acids and derivatives, 283 flavonoids, 86 lignans and coumarins, 181 lipids, 68 nucleotides and derivatives, 101 organic acids, 190 phenolic acids, 10 quinones, 4 steroids, 17 tannins, 111 terpenoids, and 177 other metabolites. We compared the different metabolites in seeds between HKH, ZM, ZY, and LY. The 1311 identified different metabolites were classified into three categories. Sixty-three overlapping significant different metabolites were found, of which lignans and coumarins accounted for the largest proportion. The differentially accumulated metabolites were enriched in different metabolic pathways between HKH vs. LY, HKH vs. ZM, HKH vs. ZY, LY vs. ZY, ZM vs. LY and ZM vs. ZY, with the most abundant metabolic pathways being 4, 2, 4, 7, 7 and 5, respectively (p < 0.05). Moreover, among the top 20 metabolites in each subgroup comparison in terms of difference multiplicity 7, 8 and 13. ZM and ZY had the highest phenolic acid content. Ninety-six disease-resistant metabolites and 48 major traditional Chinese medicine agents were identified based on seven diseases. The results of this study will not only lead to a more comprehensive and in-depth understanding of the metabolic properties of C. tuberculata seeds, but also provide a scientific basis for the excavation and further development of its medicinal value.


Assuntos
Camellia , Hidroxibenzoatos , Lignanas , Camellia/química , Antioxidantes/química , Espectrometria de Massas em Tandem , Flavonoides/análise , Sementes/química , Metabolômica/métodos , Extratos Vegetais/química , Lignanas/análise , Cumarínicos/análise
9.
J Chromatogr A ; 1721: 464845, 2024 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-38552371

RESUMO

Non-Hodgkin lymphoma (NHL) is a heterogeneous group of malignant tumors occurring in B or T lymphocytes, and no small molecule-positive drugs to treat NHL have been marketed. Cluster of differentiation 20 (CD20) is an important molecule regulating signaling for the life and differentiation of B lymphocytes and possesses the characteristics of a drug target for treating NHL. 2-Methoxyestradiol induces apoptosis in lymphoma Raji cells and CD20 protein is highly expressed by Raji lymphoma cells. Therefore, in this study, a CD20-SNAP-tag/CMC model was developed to validate the interaction of 2-methoxyestradiol with CD20. 2-Methoxyestradiol was used as a small molecule control compound, and the system was validated for good applicability. The cell membrane chromatography model was combined with high-performance liquid chromatography ion trap time-of-flight mass spectroscopy (HPLC-IT-TOF-MS) in a two-dimensional system to successfully identify, analyze, and characterize the potential active compounds of Schisandra chinensis (Turcz.) Baill. extract and Lysionotus pauciflorus Maxim. extract, including Schisandrin A, Schizandrol A, Schizandrol B, Schisantherin B, and Nevadensin, which can act on CD20 receptors. The five potential active compounds were analyzed by non-linear chromatography. The thermodynamic and kinetic parameters of their interaction with CD20 were also analyzed, and the mode of interaction was simulated by molecular docking. Their inhibitory effects on lymphoma cell growth were assessed using a Cell Counting Kit-8 (CCK-8). Nevadensin and Schizandrin A were able to induce apoptosis in Raji cells within a certain concentration range. In conclusion, the present experiments provide some bases for improving NHL treatment and developing small molecule lead compounds targeting CD20 with low toxicity and high specificity.


Assuntos
Cromatografia Líquida de Alta Pressão , Medicamentos de Ervas Chinesas , Humanos , 2-Metoxiestradiol , Células Imobilizadas/química , Cromatografia Líquida de Alta Pressão/métodos , Ciclo-Octanos , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/química , Cromatografia Gasosa-Espectrometria de Massas , Lignanas/análise , Linfoma/tratamento farmacológico , Medicina Tradicional Chinesa , Simulação de Acoplamento Molecular , Compostos Policíclicos , Schisandra/química
10.
Phytomedicine ; 128: 155361, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38552434

RESUMO

BACKGROUND: As a traditional Chinese herbal medicine, Schisandra chinensis exhibits various effects such as liver protection, blood sugar regulation, blood lipid regulation, immune function regulation, antidepressant activity, etc. However, because of its intricate composition, diverse origins, and medicinal effects depending on complex compound groups, there are differences in the lignan composition of S. chinensis from different origins. Therefore, it is currently difficult to evaluate the quality of medicinal materials from plants of different origins using a single qualitative quality control index. PURPOSE: This paper aims to investigate the potential relationship between the lignan components of S. chinensis from different origins and to establish stable assessment indices for determining the lignan content of S. chinensis from multiple perspectives. METHODS: In this study, we collected S. chinensis samples of seven major origins in China, and randomly sampled 6-9 batches of each origin for a total of 60 batches. The lignan content was determined by HPLC, and its distribution law of the ratio of each lignan component of S. chinensis to Schisandrol A content was analyzed. Combining network pharmacology and differential analysis between samples, the stable and effective substances used as quality markers were determined. RESULTS: There were some correlations among the lignan contents of S. chinensis, some correlations between schisandrin A and other lignans of S. chinensis could be determined. The ratio of each component to the indicator component schisandrol A was evenly distributed and reflected the lignan content of S. chinensis to some extent. Four substances (schisandrol A, schisandrol B, schisantherin A, and schisandrin C) were determined by network pharmacology combined with the analysis results of HCA, PCA and PLS-DA to further optimize the model. They displayed a strong connection with the core target, a large contribution rate to the principal components, and a stable content in each batch of samples, suggesting that these components may be the main active substances of S. chinensis lignans. Therefore, they could be used as main indicators evaluating the advantages and disadvantages of S. chinensis by examining the consistency of component proportions. CONCLUSION: This method can intuitively evaluate the content of main lignans in S. chinensis. This quality assessment model is an exploration of the multi-component comprehensive evaluation system of S. chinensis, providing a new concept for the quality evaluation system of Chinese herbal medicines.


Assuntos
Ciclo-Octanos , Medicamentos de Ervas Chinesas , Lignanas , Schisandra , Schisandra/química , Lignanas/análise , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Cromatografia Líquida de Alta Pressão/métodos , Ciclo-Octanos/análise , China , Compostos Policíclicos/análise , Dioxóis/análise , Controle de Qualidade , Análise de Componente Principal
11.
Iran J Med Sci ; 49(1): 30-39, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38322161

RESUMO

Background: Herbal medicines are the preferred anticancer agents due to their lower cytotoxic effects on healthy cells. Plant lignans play an important role in treating various diseases, especially cancer. The present study aimed to evaluate the effect of podophyllotoxin, pinoresinol, and lariciresinol on cellular toxicity and inducing apoptosis in fibroblasts, HEK-293, and SkBr3 cell lines. Methods: An in vitro study was conducted from 2017 to 2019 at the Faculty of Biological Sciences, Tarbiat Modares University (Tehran, Iran). The cell lines were treated for 24 and 48 hours with different concentrations of lignans. Cell viability and apoptosis were examined using MTT and flow cytometry, respectively. Expression levels of cell cycle and apoptosis regulator genes were determined using quantitative real-time polymerase chain reaction. Data were analyzed using a two-way analysis of variance followed by Tukey's HSD test. P<0.05 was considered statistically significant. Results: Podophyllotoxin significantly increased apoptosis in fibroblast cells compared to pinoresinol and lariciresinol (P<0.001). The percentage of cell viability of fibroblast cells treated for 48 hours with pinoresinol, lariciresinol, and podophyllotoxin was reduced by 49%, 47%, and 36%, respectively. Treatment with pinoresinol and lariciresinol significantly overexpressed pro-apoptotic genes and underexpressed anti-apoptotic genes in SkBr3 cells (P<0.001). SkBr3 cells treated with lariciresinol significantly reduced gene expression (P<0.001). Conclusion: Pinoresinol and lariciresinol can potentially be used as new therapeutic agents for the treatment of breast cancer.


Assuntos
Antineoplásicos , Neoplasias da Mama , Furanos , Lignanas , Humanos , Feminino , Podofilotoxina/análise , Oxirredutases/genética , Oxirredutases/metabolismo , Células HEK293 , Irã (Geográfico) , Lignanas/análise , Lignanas/metabolismo
12.
Plant Foods Hum Nutr ; 79(1): 159-165, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38236453

RESUMO

Linseed represents a rich source of nutritional, functional and health-beneficial compounds. Nevertheless, the chemical composition and content of bioactive compounds may be quite variable and potentially affected by various factors, including genotype and the environment. In this study, the proximate chemical composition, lignans content and antioxidant potential of six experimentally grown linseed cultivars were assessed and compared. A diagonal cultivation trial in the University of South Bohemia Experimental Station in Ceské Budejovice, Czech Republic, was established in three subsequent growing seasons (2018, 2019 and 2020). The results showed that the cultivar and growing conditions influenced most studied parameters. The lack of precipitation in May and June 2019 negatively affected the seed yield and the level of secoisolariciresinol diglucoside but did not decrease the crude protein content, which was negatively related to the oil content. The newly developed method for lignans analysis allowed the identification and quantification of secoisolariciresinol diglucoside and matairesinol. Their content correlated positively with the total polyphenol content and antioxidant assays (DPPH and ABTS radical scavenging activity), indicating the significant contribution to the biofunctional properties of linseed. On the other hand, we did not detect minor linseed lignans, pinoresinol and lariciresinol. The results of this study showed the importance of cultivar and growing conditions factors on the linseed chemical composition and the lignans content, determining its nutritional and medicinal properties.


Assuntos
Linho , Glucosídeos , Lignanas , Antioxidantes/análise , Butileno Glicóis/análise , Butileno Glicóis/química , Butileno Glicóis/metabolismo , Linho/química , Lignanas/análise , Lignanas/química , Lignanas/metabolismo
13.
Artigo em Inglês | MEDLINE | ID: mdl-38109812

RESUMO

Separation and purification of naturally occurring isomers from herbs are still challenging. High-speed counter-current chromatography (HSCCC) has been applied to isolate natural products. In this study, an off-line multi-dimensional high-speed counter-current chromatography (multi-D HSCCC) strategy was developed utilizing the in situ concentration technique with online storage recycling elution to rapidly separate bioactive isomeric neolignans from chloroform-partitioned samples of the plant Piper betle L. In the procedure, the crude sample (105 mg) was implemented using the online storage recycling technique in a two-phase solvent system composed of petroleum ether-ethyl acetate-methanol-water (7: 5: 12: 3), which first simply afforded a neolignane kadsurenone (1, 5.3 mg) and its epimer (-)-denudatin B (2, 6.4 mg). Then, the remains fr a was subjected to the second-dimensional HSCCC elution using the in situ concentration technique with online storage recycling technique in another solvent system of petroleum ether-ethyl acetate-methanol-water (5: 5: 11, 15). As a result, kadsurenin I (3, 0.6 mg) and its regioisomer pibeneolignan C (4, 5.0 mg), together with the fractional remaining fr b and fr c, were obtained. Thirdly, the fr c was reloaded to allow the HSCCC for recycling elution with the former solvent system employing the in situ concentration strategy and yielded a pair of epimers, (7R,8S,1'S)-1'-allyl-5-methoxy-8-methyl-7-piperonyl-7,8,3,6-tetrahydro-2-oxobenzofuran (5, 10.2 mg), and 3-epi-(-)-burchullin (6, 2.6 mg). Finally, the three pairs of less amount and the structurally similar isomers 1-6 were isolated from the crude fraction of P. betle with a high HPLC purity of over 95.0 % for compound 2, 4-6 and 92.5 % for compound 1, 91.0 % for 3, while the purity of 1 and 3 in 1H NMR were 89.9 % and 91.1 %, respectively. The whole isolation process was quick and efficient. Compounds 1, 2, 4 and 5 showed significantly synergistic activities combining several antibiotics against five drug-resistant Staphylococcus aureus with FICIs from 0.156 to 0.375. This novel off-line multi-dimensional HSCCC strategy could be broadened to application for the rapid separation of complex natural products.


Assuntos
Acetatos , Alcanos , Lignanas , Staphylococcus aureus Resistente à Meticilina , Piper betle , Distribuição Contracorrente/métodos , Metanol , Extratos Vegetais/química , Lignanas/análise , Cromatografia Líquida de Alta Pressão/métodos , Solventes , Água
14.
J Sep Sci ; 46(20): e2300466, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37599277

RESUMO

Schisandra chinensis is a traditional Chinese medicine, which has played an important role in the field of medicine and food. In this study, ultra-high-performance liquid chromatography quadrupole-orbitrap-mass spectrometry was used to rapidly classify and identify the chemical compositions. Note that 32, 28, and 30 kinds of compounds were successfully identified from northern Schisandra chinensis, vinegar-processed Schisandra chinensis, and wine-processed Schisandra chinensis, respectively. The cleavage patterns of various components including lignans, organic acids, flavonoids, and terpenoids were summarized, and the effects of different processing methods on Schisandra chinensis were analyzed through chemical composition. This method realized the rapid classification and identification of raw Schisandra chinensis and two different processed products, and provided references for improving the traditional processing methods, strengthening quality control, and ensuring safe clinical application.


Assuntos
Medicamentos de Ervas Chinesas , Lignanas , Schisandra , Cromatografia Líquida de Alta Pressão/métodos , Schisandra/química , Lignanas/análise , Medicamentos de Ervas Chinesas/análise , Espectrometria de Massas em Tandem/métodos
15.
Zhongguo Zhong Yao Za Zhi ; 48(9): 2435-2454, 2023 May.
Artigo em Chinês | MEDLINE | ID: mdl-37282873

RESUMO

This study aimed to investigate the impact of ginger juice on chemical profile of Magnoliae Officinalis Cortex(MOC) when they were processed together. Ultra-high-performance liquid chromatography coupled to quadrupole-orbitrap high-resolution mass spectrometry(UHPLC-Q-Orbitrap HRMS) was used for qualitative analysis of the chemical component of MOC samples before and after being processed with ginger juice. UPLC was performed to observe the content variation of eight main components in processed MOC. A total of 174 compounds were identified or tentatively deduced from processed and unprocessed MOC samples according to MS data obtained in positive and negative ion mode. After MOC was processed with ginger juice, the peak areas of most phenolics increased, while the peak areas of most phenylethanoid glycosides decreased; as for neolignans, oxyneolignans, other lignans and alkaloids, changes in the peak area were variable, and the peak areas of terpenoid-lignans varied little. Additionally, gingerols and diarylheptanoids were only detected in the processed MOC sample. The contents of syringin, magnoloside A, and magnoloside B decreased significantly in the processed MOC sample while no significant difference was observed in the contents of magnoflorine, magnocurarine, honokiol, obovatol, and magnolol. This study comprehensively explored the content variation of chemical components in processed and unprocessed MOC samples derived from different regions and with different tree ages using UPLC and UHPLC-Q-Orbitrap HRMS, and summarized the variation characteristics of various compounds. The results provide a data foundation for further research on pharmacodynamic substances of MOC processed with ginger juice.


Assuntos
Alcaloides , Lignanas , Zingiber officinale , Árvores , Cromatografia Líquida de Alta Pressão/métodos , Lignanas/análise
16.
Zhongguo Zhong Yao Za Zhi ; 48(7): 1892-1898, 2023 Apr.
Artigo em Chinês | MEDLINE | ID: mdl-37282965

RESUMO

The present study aimed to explore the chemical constituents from the stems and leaves of Cephalotaxus fortunei. Seven lignans were isolated from the 75% ethanol extract of C. fortunei by various chromatographic methods, including silica gel, ODS column chromatography, and HPLC. The structures of the isolated compounds were elucidated according to physicochemical properties and spectral data. Compound 1 is a new lignan named cephalignan A. The known compounds were identified as 8-hydroxy-conidendrine(2), isolariciresinol(3), leptolepisol D(4), diarctigenin(5), dihydrodehydrodiconiferyl alcohol 9'-O-ß-D-glucopyranoside(6), and dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(7). Compounds 2 and 5 were isolated from the Cephalotaxus plant for the first time.


Assuntos
Cephalotaxus , Lignanas , Lignanas/análise , Folhas de Planta/química , Etanol , Cromatografia Líquida de Alta Pressão
17.
Molecules ; 28(9)2023 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-37175177

RESUMO

The chemical investigation of branches of Cinnamomum camphora chvar. Borneol guided by mosquito larvicidal activity led to the isolation of fourteen known lignans (1-14). Their structures were elucidated unambiguously based on comprehensive spectroscopic analysis and comparison with the literature data. This is the first report of these compounds being isolated from branches of Cinnamomum camphora chvar. Borneol. Compounds 3-5 and 8-14 were isolated from this plant for the first time. All compounds isolated were subjected to anti-inflammatory, mosquito larvicidal activity and cytotoxic activity evaluation. Compounds (1-14) showed significant mosquito larvicidal activity against Culex pipiens quinquefasciatus with lethal mortality in 50% (LC50), with values ranging from 0.009 to 0.24 µg/mL. Among them, furofuran lignans(1-8) exhibited potent mosquito larvicidal activity against Cx. p. quinquefasciatus, with LC50 values of 0.009-0.021 µg/mL. From the perspective of a structure-activity relationship, compounds with a dioxolane group showed high mosquito larvicidal activity and have potential to be developed into a mosquitocide.


Assuntos
Aedes , Cinnamomum camphora , Culex , Culicidae , Inseticidas , Lignanas , Animais , Lignanas/farmacologia , Lignanas/análise , Inseticidas/química , Larva , Extratos Vegetais/química , Folhas de Planta/química
18.
Molecules ; 28(9)2023 May 07.
Artigo em Inglês | MEDLINE | ID: mdl-37175347

RESUMO

Plants in the genus Juniperus have been reported to produce a variety of chemical components, such as coumarins, flavonoids, lignans, sterols, and terpenoids. Here, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS) and ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) were applied to qualitatively and quantitatively analyze the major bioactive components in an ethanolic crude extract from the leaves of Juniperus chinensis L., which grows naturally in Korea. In addition, the antibacterial activity of the crude extract against pathogenic bacteria was investigated. Using LC-QTOF-MS analysis, we identified ten compounds, of which six were confirmed to be flavonoid and lignan-based components as the major bioactive components, i.e., isoquercetin, quercetin-3-O-α-l-rhamnoside, hinokiflavone, amentoflavone, podocarpusflavone A, and matairesinoside. Among them, a quantitative analysis performed using LC-MS/MS revealed that the levels of quercetin-3-O-α-l-rhamnoside and amentoflavone in the crude extract were 203.78 and 69.84 mg/g, respectively. Furthermore, the crude extract exhibited potential antibacterial activity against 10 pathogenic bacteria, with the highest antibacterial activity detected against Bordetella pertussis. Thus, further studies of the leaf extract of J. chinensis L. must be carried out to correlate the compounds present in the extract with the antibacterial activity and elucidate the mechanisms of action of this extract against bacteria.


Assuntos
Juniperus , Lignanas , Cromatografia Líquida , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massas em Tandem/métodos , Quercetina/análise , Juniperus/química , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Lignanas/farmacologia , Lignanas/análise , Bactérias , Antibacterianos/farmacologia
19.
Food Funct ; 14(11): 4966-4980, 2023 Jun 06.
Artigo em Inglês | MEDLINE | ID: mdl-37212033

RESUMO

Sesame seeds perform many therapeutic functions against several health issues especially those related to bones because they possess a rich content of calcium, vitamins, proteins, oil, and carbohydrates. Using the PubMed, ScienceDirect, and Google Scholar databases, we performed a comprehensive search of the literature from 2013 to date on reports related to sesame seeds and their bioactive ingredients. Sesamin, sesamol, sesamolin, and sesamol are the major bioactive lignans found in sesame seeds. Our comprehensive review of the literature revealed the protective role of sesame seeds towards bone health in postmenopausal osteoporosis. It was observed that sesame seeds have a positive impact on postmenopausal women experiencing bone-related problems, i.e. osteoporosis and arthritis. Therefore, this review is focused on exploring the effect of sesame seeds on bone mineralization in women experiencing menopause. Furthermore, to aid balancing the hormones in women after their disturbance by the postmenopausal phase, we highlight the effect of the daily intake of sesame seeds in women. Finally, we conclude that the supplementation of sesame seeds in a regular diet shows a positive impact on the bone health of post-menopausal osteoporosis.


Assuntos
Lignanas , Sesamum , Humanos , Feminino , Densidade Óssea , Pós-Menopausa , Dioxóis , Benzodioxóis , Lignanas/análise , Sementes/química
20.
Food Chem ; 420: 136134, 2023 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-37062083

RESUMO

Sesame is a valuable crop recognized for its rich composition and myriad of health benefits. The current study attempts to characterize sesame seeds' metabolome in relation to geographical origins i.e., Egypt, Sudan, Nigeria, in addition to samples from paste production lines along its different steps. UPLC-PDA-ESI-qTOF-MS was employed for untargeted profiling and in correlation to antioxidant capacity using DPPH, FRAP and ß-carotene-lineolate assays. 139 Peaks were identified, including novel phospholipids and catechol lignan in sesame. Furthermore, discriminatory markers belonging to coumarins, lignans, phenolic and organic acids were revealed among raw accessions, whereas roasted and unroasted seeds were distinguished by sugar, peptide/amino acid, and organic acid contents. Negative processing impact was observed in the loss of lignans during dehulling and decreased antioxidant capacity in sesame paste. However, malic acid in roasted seeds and verbascoside in Nigerian sesame could account for their improved antioxidant effects as revealed using chemometrics.


Assuntos
Sesamum , Antioxidantes/análise , Sesamum/química , Lignanas/análise , Lignanas/química , Fenóis/análise , Fenóis/química , Sementes
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