RESUMO
BACKGROUND: In Chinese Pharmacopeia, Picrasma quassioides (PQ) stems and leaves are recorded as Kumu with antimicrobial, anti-cancer, anti-parasitic effects, etc. However, thick stems are predominantly utilized as medicine in many Asian countries, with leaves rarely used. By now, the phytochemistry and bioactivity of PQ leaves are not well investigated. METHODS: An Orbitrap Elite mass spectrometer was employed to comprehensively investigate PQ stems and leaves sourced from 7 different locations. Additionally, their bioactivities were evaluated against 5 fungi, 6 Gram-positive bacteria and 9 Gram-negative bacteria, a tumor cell line (A549), a non-tumor cell line (WI-26 VA4) and N2 wild-type Caenorhabditis elegans. RESULTS: Bioassay results demonstrated the efficacy of both leaves and stems against tumor cells, several bacteria and fungi, while only leaves exhibited anthelmintic activity against C. elegans. A total of 181 compounds were identified from PQ stems and leaves, including 43 ß-carbolines, 20 bis ß-carbolines, 8 canthinone alkaloids, 56 quassinoids, 12 triterpenoids, 13 terpenoid derivatives, 11 flavonoids, 7 coumarins, and 11 phenolic derivatives, from which 10 compounds were identified as indicator components for quality evaluation. Most alkaloids and triterpenoids were concentrated in PQ stems, while leaves exhibited higher levels of quassinoids and other carbohydrate (CHO) components. CONCLUSION: PQ leaves exhibit distinct chemical profiles and bioactivity with the stems, suggesting their suitability for medicinal purposes. So far, the antibacterial, antifungal, and anthelmintic activities of PQ leaves were first reported here, and considering PQ sustainability, the abundant leaves are recommended for increased utilization, particularly for their rich content of PQ quassinoids.
Assuntos
Caenorhabditis elegans , Compostos Fitoquímicos , Picrasma , Folhas de Planta , Caules de Planta , Folhas de Planta/química , Picrasma/química , Animais , Caules de Planta/química , Caenorhabditis elegans/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Humanos , Linhagem Celular Tumoral , Estrutura Molecular , Antineoplásicos Fitogênicos/farmacologia , Alcaloides/farmacologia , Quassinas/farmacologia , Quassinas/química , Quassinas/isolamento & purificação , Anti-Helmínticos/farmacologia , Anti-Helmínticos/química , Fungos/efeitos dos fármacos , Flavonoides/farmacologia , Flavonoides/análiseRESUMO
Understanding the distribution of hundreds of thousands of plant metabolites across the plant kingdom presents a challenge. To address this, we curated publicly available LC-MS/MS data from 19,075 plant extracts and developed the plantMASST reference database encompassing 246 botanical families, 1,469 genera, and 2,793 species. This taxonomically focused database facilitates the exploration of plant-derived molecules using tandem mass spectrometry (MS/MS) spectra. This tool will aid in drug discovery, biosynthesis, (chemo)taxonomy, and the evolutionary ecology of herbivore interactions.
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Fermented oats are gaining popularity due to their nutritional value and the increasing consumer demand for health-conscious foods. These oats are believed to offer enhanced phytochemical and nutritional profiles compared to unfermented oats. The increased nutritional content of fermented oats is associated with various health benefits, including anti-inflammatory and antioxidant activities, which could potentially reduce the risk of chronic diseases. Further investigations are warranted to elucidate the nutritional benefits of fermented oats in human nutrition. This mini review provides a comprehensive overview of fermented oat products available on the market and the various production methods employed for fermenting oats. Furthermore, this review investigates how fermentation affects the chemical composition and biological functions of oats. Additionally, this manuscript presents some future perspectives on fermented oat products by discussing potential research directions and opportunities for further development. The findings presented in this review contribute to the expanding body of knowledge on fermented oats as a promising functional food, paving the way for future studies and applications in the field of nutrition and health.
Assuntos
Avena , Alimento Funcional , Humanos , Grão Comestível , Fermentação , ConhecimentoRESUMO
Liquid chromatography-mass spectrometry (LC-MS)-based metabolomics has become an important tool to increase our understanding of how diet affects human health. However, public and commercial mass spectral libraries of dietary metabolites are limited, resulting in the greatest challenge in converting mass spectrometry data into biological insights. In this study, we constructed an LC-MS/MS ginger library as an example to demonstrate the importance of dietary libraries for discovering food biomarkers. The functional and exposure biomarkers of ginger were investigated using plasma samples from mice treated with control and ginger extract diets. Our results showed clear discrimination between the metabolome of mice on normal and ginger extract diets. Using the in-house ginger library, we identified 20 ginger metabolites that can be used as exposure biomarkers of ginger. However, without the LC-MS/MS ginger library, none of the ginger metabolites could be accurately identified based on online mass databases. In addition, ginger treatment significantly impacts the endogenous metabolome, especially the purine metabolism and phenylalanine, tyrosine, and tryptophan biosynthesis. Overall, we demonstrated that the construction of LC-MS/MS spectra dietary libraries would enhance the ability to identify potential dietary biomarkers and correlate potential health benefits associated with food consumption.
Assuntos
Zingiber officinale , Animais , Biomarcadores/metabolismo , Cromatografia Líquida/métodos , Zingiber officinale/química , Humanos , Metaboloma , Metabolômica/métodos , Camundongos , Fenilalanina/metabolismo , Purinas/metabolismo , Espectrometria de Massas em Tandem/métodos , Triptofano/metabolismo , Tirosina/metabolismoRESUMO
[This corrects the article DOI: 10.3389/fphar.2021.761751.].
RESUMO
The stem of Picrasma quassioides (PQ) was recorded as a prominent traditional Chinese medicine, Kumu, which was effective for microbial infection, inflammation, fever, and dysentery, etc. At present, Kumu is widely used in China to develop different medicines, even as injection (Kumu zhusheye), for combating infections. However, the chemical basis of its antimicrobial activity has still not been elucidated. To examine the active chemicals, its stem was extracted to perform bioassay-guided purification against Staphylococcus aureus and Escherichia coli. In this study, two types of columns (normal and reverse-phase) were used for speedy bioassay-guided isolation from Kumu, and the active peaks were collected and identified via an UHPLC-Orbitrap-Ion Trap Mass Spectrometer, combined with MS Fragmenter and ChromGenius. For identification, the COCONUT Database (largest database of natural products) and a manually built PQ database were used, in combination with prediction and calculation of mass fragmentation and retention time to better infer their structures, especially for isomers. Moreover, three standards were analyzed under different conditions for developing and validating the MS method. A total of 25 active compounds were identified, including 24 alkaloids and 1 triterpenoid against S. aureus, whereas only ß-carboline-1-carboxylic acid and picrasidine S were active against E. coli. Here, the good antimicrobial activity of 18 chemicals was reported for the first time. Furthermore, the spectrum of three abundant ß-carbolines was assessed via their IC50 and MBC against various human pathogens. All of them exhibited strong antimicrobial activities with good potential to be developed as antibiotics. This study clearly showed the antimicrobial chemical basis of Kumu, and the results demonstrated that HRMS coupled with MS Fragmenter and ChromGenius was a powerful tool for compound analysis, which can be used for other complex samples. Beta-carbolines reported here are important lead compounds in antibiotic discovery.
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Through the use of the Global Natural Product Social (GNPS) feature-based networking system, a series of newly identified steroidal saponins were discovered in oat. The structures of the three new major steroidal saponins, sativacosides A-C (1-3), were characterized by analyzing their high-resolution MS, 1D and 2D NMR spectra, and an additional eight new steroidal saponins were also tentatively identified (4-11) based on their tandem mass spectra and typical fragments. Using ultrahigh-performance liquid chromatography with tandem mass spectrometry techniques, a complete profile of the new sativacoside series was established, and the contents of sativacosides A-C were quantified in 18 different commercial oat products. The total levels of sativacosides A-C varied from 62.2 to 192.9 µg/g in these 18 products, in which oat bran (11 samples) and oatmeal (3 samples) had higher levels than cold oat cereal (4 samples).
Assuntos
Avena , Saponinas , Cromatografia Líquida de Alta Pressão , Extratos Vegetais , Espectrometria de Massas em TandemRESUMO
2'-Acetylacteoside-(2'-AA), a bioactive constituent isolated from Cistanche deserticola, has been proven to possess a variety of important pharmacological effects, thus brought an increased amount of scientists' attention. As the extract of C. deserticola exhibited significant anti-osteoporotic bioactivity in our previous study, we proposed that 2'-AA maybe one of the responsibilities. As a result, 2'-AA (10, 20 and 40 mg/kg body weight/day) exhibited significant anti-osteoporotic effects on ovariectomized (OVX) mice after 12 weeks of oral administration, confirmed by the increased bone mineral density, enhanced bone strength and improved trabecular bone micro-architecture including bone mineral content, tissue mineral content, trabecular number, and trabecular separation of OVX mice. Moreover, the properties of bone resorption markers including cathepsin K, TRAP and deoxypyridinoline were significantly suppressed, whereas the activities of bone formation index like ALP and BGP as well as the weights of the body, uterus, and vagina were seemingly not influenced by 2'-AA intervention. Mechanistically, the above therapeutic effect of 2'-AA on bone resorption of OVX mice operated maybe mainly through RANKL/RANK/TRAF6-mediated NF-κB/NFATc1 pathway, which was confirmed by the down-regulated expressions of RANK, TRAF6, IκB kinase ß, NF-κB and NFATc1. Summarily, 2'-AA exhibited significant anti-osteoporotic activity and may be regarded as a promising anti-osteoporotic candidate for future clinical trial.
Assuntos
Reabsorção Óssea/prevenção & controle , Glucosídeos/farmacologia , Animais , Fenômenos Biomecânicos/efeitos dos fármacos , Densidade Óssea/efeitos dos fármacos , Feminino , Medicina Tradicional Chinesa , Camundongos , NF-kappa B/fisiologia , Fatores de Transcrição NFATC/fisiologia , Tamanho do Órgão/efeitos dos fármacos , Osteogênese/efeitos dos fármacos , Osteoporose/prevenção & controle , Ovariectomia , Células RAW 264.7RESUMO
Oats are commonly consumed as whole grains and generally considered as a healthy food. However, the bioactive compounds in oats have not been fully investigated. In this study, we reported for the first time the purification, structure elucidation, and chemical profile of the major triterpenoid saponins in oat bran as well as the quantification of the major triterpenoid saponins in commercial oat products. Thirteen triterpenoid saponins (1-13) were purified from oat bran. Their structures were characterized by analyzing their high-resolution mass spectrometry (MS), one-dimensional (1-D), and two-dimensional (2-D) NMR spectra. All of the purified triterpenoid saponins have been reported from oat bran for the first time, in which compounds (1-8) are newly discovered compounds and compound (9) is a new natural product. Using ultra-high-performance liquid chromatography with tandem mass spectrometry techniques, a complete profile of oat triterpenoid saponins was established, and the contents of the 13 purified triterpenoid saponins were quantitated in 19 different commercial oat products. The total levels of the 13 triterpenoid saponins varied from 1.77 to 18.20 µg/g in these 19 products, in which oat bran (11 samples) and oatmeal (three samples) had higher levels than cold oat cereal (five samples). Among the 11 commercial oat bran samples, the average total levels of the 13 triterpenoid saponins in the five sprouted oat samples are slightly higher than those in the regular oat bran products.
Assuntos
Avena/química , Extratos Vegetais/química , Saponinas/química , Triterpenos/química , Cromatografia Líquida de Alta Pressão , Fibras na Dieta/análise , Estrutura Molecular , Espectrometria de Massas em TandemRESUMO
Serotonin is an important endogenous regulatory neurotransmitter and has also been found in fruits, vegetables, and nuts. Methylglyoxal (MGO) is a reactive dicarbonyl metabolite and also a food toxin that modifies protein and DNA to cause the development of many chronic diseases. The objective of this study is to understand the reaction mechanisms between serotonin and MGO and determine whether serotonin could trap MGO in vivo. Five products were detected in phosphate buffer (pH 7.4) at 37 °C. Four products (compounds 2 and 4-6) were purified from the reaction mixture, and their structures were characterized by the analysis of their high-resolution mass and one- and two-dimensional nuclear magnetic resonance spectra. One product (compound 3), as a result of its instability, could not be properly purified and was tentatively characterized on the basis of its high-resolution mass spectrum and corresponding mass fragments. On the basis of the structures of these five products, two reaction pathways were proposed. Compounds 2, 3, 5, and 6 were produced through the Pictet-Spengler condensation pathway between the primary amine of serotonin and the ketone of MGO, and compound 3 was identified as the intermediate product to form products 2, 5, and 6, whereas compound 4 was formed through nucleophilic substitution by the benzene ring of serotonin, which is a new reaction pathway between biogenic amines and reactive carbonyl species. More importantly, the detection of adducts 2 and 4-6 in mice supports our hypothesis that the reaction between serotonin and MGO also happens in vivo through the same pathways as those in model reactions, suggesting that dietary or endogenous serotonin has the capacity to trap MGO in vivo.
Assuntos
Aldeído Pirúvico/química , Aldeído Pirúvico/metabolismo , Serotonina/química , Serotonina/metabolismo , Animais , Espectroscopia de Ressonância Magnética , Masculino , Espectrometria de Massas , Camundongos , Estrutura MolecularRESUMO
Six spirobiflavonoid stereoisomers including two new ones, spiropensilisols A (1) and B (2), were isolated from a mass-limited trunk barks of Glyptostrobus pensilis, an endangered conifer endemic to China. The new structures featuring a benzofuran-containing spirolactone and their absolute configurations were determined by extensive spectroscopic methods. All the isolates showed significant inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B) enzyme, a potential therapeutic target for diabetes and obesity, with IC50 values ranging from 3.3 to 17.1 µM. A preliminary SAR analysis with assistance of the molecular modeling approach was performed for the most potent compound (i.e., 1), to understand the nature of interactions governing the binding mode of spirobiflavonids within the active site of the PTP1B enzyme.
Assuntos
Inibidores Enzimáticos/química , Flavonoides/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Traqueófitas/química , Sítios de Ligação , Domínio Catalítico , Inibidores Enzimáticos/metabolismo , Flavonoides/isolamento & purificação , Flavonoides/metabolismo , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Simulação de Acoplamento Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Estereoisomerismo , Relação Estrutura-Atividade , Traqueófitas/metabolismoRESUMO
Avenanthramides (AVAs) are unique phytochemicals in oat that contain two distinct groups of compounds. The first group is constituted by N-cinnamoylanthranilic acids with a single double bond (referred to as C type), and the other group is constituted by N-avenalumoylanthranilic acids with two double bonds (referred to as A type). C-type AVAs have been reported with their chemical profiles and levels in commercial oat products as well as their bioactivities. However, the accurate levels of A-type AVAs in commercial sprouted oat products and their bioactivity are still unknown. In this study, we purified seven A-type AVAs from sprouted oat bran and characterized their structures with corresponding mass spectrometry and nuclear magnetic resonance data. Among them, five compounds were isolated from oat bran for the first time. The purified A-type AVAs were used as authentic standards to establish the chemical profile of A-type AVAs in oat and to quantify the levels of all individual A-type AVAs in six commercial sprouted oat products using ultra-high-performance liquid chromatography with tandem mass spectrometry. The total A-type AVA contents in the various oat products ranged from 7.85 to 133.3 µg/g. Furthermore, the inhibition of lipopolysaccharide-induced nitric oxide production and inducible nitric oxide synthase expression by A- and C-type AVAs in macrophages were compared. The most abundant A-type AVAs (2pd, 2cd, and 2fd) have similar anti-inflammatory activity to the major C-type AVAs (2p, 2c, and 2f). To the best of our knowledge, this is the first report on the bioactivity of A-type AVAs.
Assuntos
Anti-Inflamatórios/química , Avena/química , ortoaminobenzoatos/química , Animais , Anti-Inflamatórios/farmacologia , Avena/crescimento & desenvolvimento , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Sementes/química , Sementes/crescimento & desenvolvimento , ortoaminobenzoatos/farmacologiaRESUMO
Given the limitations of existing therapeutic agents for treatment of postmenopausal osteoporosis, there still remains a need for more options with both efficacy and less adverse effects. Cistanche deserticola Y. C. Ma is known as a popular tonic herb traditionally used to treatment deficiency of kidney energy including muscle weakness in minority area of Asian counties. Based on the theory of "kidney dominate bone," an ovariectomized (OVX) rat model of postmenopausal osteoporosis was used to evaluate the therapeutic effect of C. deserticola extract (CDE) on bone loss. Forty eight female Sprague-Dawley rats, aged about 12 weeks, were randomly assigned into six groups including sham group orally administrated with 0.5% carboxymethyl cellulose sodium (CMC-Na) (sham), positive group treated with 1 mg/kg of estradiol valerate (EV), low, moderate, and high dosage groups orally administrated with 200, 400, and 800 mg/kg/day of CDE, respectively. After 3 months of continuous intervention, CDE exhibited significant anti-osteoporotic activity evidenced by the enhanced total bone mineral density, ameliorated bone microarchitecture; increased alkaline phosphatase activity; decreased deoxypyridinoline, cathepsin K, tartrate-resistant acid phosphatase, and malondialdehyde levels; whereas the body, uterus, and vagina weights in OVX rats were not influenced by CDE intervention. In addition, a seemed contradictory phenomenon on levels of calcium and phosphorus between OVX and sham rats were observed and elucidated. Mechanistically, CDE significantly down-regulated the levels of TRAF6, RANKL, RANK, NF-κB, IKKß, NFAT2, and up-regulated the phosphatidylinositol 3-kinase (PI3K), AKT, osteoprotegerin, and c-Fos expressions, which implied CDE could suppress RANKL/RANK-induced activation of downstream NF-κB and PI3K/AKT pathways, and ultimately, preventing activity of the key osteoclastogenic proteins NFAT2 and c-Fos. All of the data suggested CDE possessed potential anti-osteoporotic activity and this effect was, at least in part, involved in modulation of RANKL/RANK/TRAF6-mediated NF-κB and PI3K/AKT signaling as well as c-Fos and NFAT2 levels. Therefore, CDE may represent a useful promising remedy candidate for treatment of postmenopausal osteoporosis.
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There is convincing evidence that consuming whole grains (WGs) may decrease the risk of colorectal cancer (CRC). Wheat bran (WB) is a rich source of dietary fiber and phytochemicals with health-promoting properties. However, the active components especially the interaction between different components in WG wheat have not been fully explored. Here, we investigated whether one of the major WB phytochemicals, alkylresorcinol (AR) C21, and the major active intestinal microbial metabolite of fiber, butyrate, could synergistically suppress human colon cancer cells. Our results demonstrated for the first time that the combination of C21 and butyrate synergistically inhibited the growth of human colon cancer cells and induced apoptosis. Further mechanistic studies demonstrated that the cotreatment of C21 and butyrate induced significant up-regulations in cleaved Poly(ADP-ribose) polymerase (PARP), cleaved caspase 3, p53 upregulated modulator of apoptosis (PUMA), cytochrome C, lipid-conjugated membrane-bound form of microtubule-associated protein 1A/1B-light chain 3 (LC3-II), and C/EBP homologous protein (CHOP) expressions, indicating the synergistic anticancer effects of C21 and butyrate were associated with induction of apoptosis, autophagy, and ER stress pathways. Notably, the C21 concentrations in the large intestinal tract of mice treated with human relevant doses of C21, were from 0.86 to 1.78 µmol/g, suggesting the C21 doses used in vitro may be achievable after daily WG wheat intake. These results provide novel insights into the dietary prevention of CRC regarding the potential interaction of bioactive WG wheat phytochemicals and the microbial metabolites of fiber.
Assuntos
Butiratos/metabolismo , Neoplasias do Colo/tratamento farmacológico , Fibras na Dieta/análise , Microbioma Gastrointestinal/efeitos dos fármacos , Intestinos/microbiologia , Compostos Fitoquímicos/administração & dosagem , Resorcinóis/administração & dosagem , Animais , Autofagia/efeitos dos fármacos , Caspase 3/genética , Caspase 3/metabolismo , Linhagem Celular Tumoral , Neoplasias do Colo/metabolismo , Neoplasias do Colo/microbiologia , Neoplasias do Colo/fisiopatologia , Humanos , Intestinos/efeitos dos fármacos , Masculino , Camundongos , Compostos Fitoquímicos/química , Poli(ADP-Ribose) Polimerases/genética , Poli(ADP-Ribose) Polimerases/metabolismo , Resorcinóis/químicaRESUMO
Acteoside, an active phenylethanoid glycoside compound isolated from herbs of Cistanche, was chosen for the investigation of anti-osteoporotic effect on postmenopausal osteoporosis by using an ovariectomized (OVX) mice model. The results from in vivo experiments showed that after daily oral administration of acteoside (20, 40, and 80 mg/kg body weight/day) for 12 weeks, bone mineral density and bone biomechanical properties of OVX mice were greatly enhanced, with significant improvement in bone microarchitecture. Furthermore, biochemical parameters of bone resorption markers as well as bone formation index, including tartrate-resistant acid phosphatase, cathepsin K, deoxypyridinoline, alkaline phosphatase, and bone gla-protein, were ameliorated by acteoside treatment, whereas the body, uterus, and vagina wet weights were seemingly not impacted by acteoside administration. Acteoside significantly affected osteoclastogenesis by attenuating nuclear factor kappa B (NF-κB) and stimulating phosphoinositide 3-kinase (PI3K)/protein kinase B (AKT) signal pathways through down-regulated levels of tumor-necrosis factor receptor-associated factor 6 (TRAF6), receptor activator of nuclear factor kappa B ligand (RANKL), RANK, NFKBIA, IκB kinase ß, nuclear factor of activated T-cells c2 (NFAT2), and up-regulated expressions of PI3K, AKT, and c-Fos. Accordingly, the current research validated our hypothesis that acteoside possesses potent anti-osteoporotic properties and may be a promising agent for the prevention of osteoporosis in the future.
Assuntos
Glucosídeos/farmacologia , Osteoporose/etiologia , Osteoporose/metabolismo , Ovariectomia/efeitos adversos , Fenóis/farmacologia , Substâncias Protetoras/farmacologia , Animais , Biomarcadores , Peso Corporal , Densidade Óssea/efeitos dos fármacos , Reabsorção Óssea/tratamento farmacológico , Reabsorção Óssea/genética , Osso e Ossos/efeitos dos fármacos , Osso e Ossos/metabolismo , Modelos Animais de Doenças , Feminino , Camundongos , Modelos Biológicos , Tamanho do Órgão , Osteoporose/tratamento farmacológico , Osteoporose/patologia , Ligante RANK/metabolismo , Receptor Ativador de Fator Nuclear kappa-B/metabolismo , Fator 6 Associado a Receptor de TNF/metabolismoRESUMO
Ten diterpenoids including three new abietanes (1-3) were isolated from the twigs and needles of Podocarpus imbricatus, an endangered conifer growing in a Cantonese garden. The new structures were established by means of spectroscopic methods. Among the isolates, 3ß-hydroxy-abieta-8,11,13-trien-7-one (5), decandrin G (6), and 7,15-pimaradien-18-oic acid (8) showed significant anti-neuroinflammatory activities by inhibiting the overproduction of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells, with IC50 values of 3.7, 11.1, and 4.5 µM, respectively.
Assuntos
Abietanos/isolamento & purificação , Abietanos/farmacologia , Traqueófitas/química , Animais , Lipopolissacarídeos/farmacologia , Camundongos , Microglia/efeitos dos fármacos , Estrutura Molecular , Óxido Nítrico/biossínteseRESUMO
During a further and comprehensive phytochemical investigation on the shed trunk barks of the critically endangered plant Abies beshanzuensis, one new (1) and ten known (2-11) lignans with diverse structures were isolated. On the basis of spectroscopic methods, the new structure was established to be (7S,8R,8'R)-4'-methoxyl-α-conidendrin (1). Among the isolated lignans, (-)-matairesinol (5) and (-)-arctigenin (6) showed significant anti-neuroinflammatory activities by inhibiting the overproduction of nitric oxide in lipopolysaccharide-stimulated murine BV-2 microglial cells, with IC50 values of 11.5 and 19.0 µM, respectively.
Assuntos
Abies/química , Anti-Inflamatórios/isolamento & purificação , Lignanas/isolamento & purificação , Animais , Anti-Inflamatórios/farmacologia , Células Cultivadas , Furanos/farmacologia , Lignanas/química , Lignanas/farmacologia , Camundongos , Microglia/efeitos dos fármacos , Óxido Nítrico/biossíntese , Casca de Planta/químicaRESUMO
Nine unexpected new flavonol glycoside cyclodimers in the truxinate (1-7, biginkgosides A-G, respectively) or truxillate [biginkgosides H (8) and I (9)] forms were isolated as minor components from the extract of Ginkgo biloba leaves. The new dimers possess an unusual cyclobutane ring formed by a [2+2]-cycloaddition between two symmetric (for compounds 1-5 and 7-9) or nonsymmetric (for 6) flavonol coumaroyl glucorhamnosides. A plausible biosynthetic pathway for these new compounds based on the frontier molecular orbital theory of cycloaddition reactions is briefly discussed. An antineuroinflammatory screening revealed that biginkgosides E (5) and H (8) inhibited nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells, with IC50 values of 2.91 and 17.23 µM, respectively. Additionally, biginkgoside F (6) showed a significant neuroprotective effect (34.3% increase in cell viability at 1 µM) against Aß25-35-induced cell viability decrease in SH-SY5Y neuroblastoma cells.
Assuntos
Peptídeos beta-Amiloides/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Flavonóis/isolamento & purificação , Flavonóis/farmacologia , Ginkgo biloba/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Fármacos Neuroprotetores/farmacologia , Folhas de Planta/química , Peptídeos beta-Amiloides/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Ésteres , Flavonóis/química , Glicosídeos/química , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Estrutura Molecular , Neuroblastoma/tratamento farmacológico , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular , Fragmentos de Peptídeos/efeitos dos fármacos , Extratos Vegetais/farmacologiaRESUMO
The genus Fagopyrum (Polygonaceae), currently comprising 15 species of plants, includes three important buckwheat species: Fagopyrum esculentum (F. esculentum) Moench. (common buckwheat), Fagopyrum tataricum (F. tataricum) (L.) Gaertn. (tartary buckwheat) and Fagopyrum dibotrys (F. dibotrys) (D. Don) Hara. (perennial buckwheat), which have been well explored due to their long tradition of both edible and medicinal use. This review aimed to present an up-to-date and comprehensive analysis of the phytochemistry and pharmacology of the three Fagopyrum buckwheats. In addition, the scope for future research was also discussed. All available references included in this paper were compiled from major databases, such as MEDLINE, Pubmed, Scholar, Elsevier, Springer, Wiley and CNKI. A total of 106 compounds isolated from three Fagopyrum buckwheats can be mainly divided into six classes: flavonoids, phenolics, fagopyritols, triterpenoids, steroids and fatty acids. Flavonoids and phenolic compounds were considered to be the major active components. Considerable pharmacological experiments both in vitro and in vivo have validated that Fagopyrum buckwheats possess antitumor, anti-oxidant, anti-inflammatory, hepatoprotective, anti-diabetic activities, etc. All reported data lead us to conclude that Fagopyrum buckwheats have convincing medicinal potential. However, further research is needed to explore its bioactive constituents, the relationship to their structural activities and the molecular mechanisms of action.