RESUMO
OBJECTIVES: Ranunculus L. genus contains 413 species, and it is the biggest genus in the family Ranunculaceae Juss. This review is to provide botanical characteristics, traditional uses, phytochemistry, pharmacology, toxicity, and pharmaceutical preparations of the genus Ranunculus. KEY FINDINGS: The genus Ranunculus contains flavonoids, organic acids, coumarins, lactones, glycosides, sterols, polysaccharides, and trace elements. These chemical constituents complement the pharmacological actions and work together to exert anti-inflammatory, anticancer, antitubercular, antibacterial, antimalarial, etc. Those traditional Chinese medicine characteristics, like clearing away heat and detoxification, make this genus significant in ethnic medicine. The progress in research and the development of various pharmaceutical preparations made it appear in epidemiological and clinical studies. SUMMARY: The genus Ranunculus has attracted the attention of experts and scholars in many fields due to its unique advantages. However, there are many species that are not scientifically investigated. The toxicity issues are also a huge concern. Fortunately, the toxicity can be overcome via special processes like drying or heating and by choosing a safe extraction solvent, such as water thus ensuring the safety of medication. Pharmaceutical preparations containing the plants from Ranunculus have gratifying clinical value, but they are not promoted sufficiently. Therefore, further research should be carried out to promote the genus for its health benefits to humans.
Assuntos
Ranunculus , Ranunculus/química , Humanos , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/toxicidade , Compostos Fitoquímicos/isolamento & purificação , Animais , Medicina Tradicional Chinesa/métodos , Ásia , Fitoterapia , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/toxicidade , Extratos Vegetais/farmacologia , Extratos Vegetais/toxicidade , Extratos Vegetais/química , EtnofarmacologiaRESUMO
CONTEXT: Ranunculus ternatus Thunb (Ranunculaceae), (RTT) is used clinically for the treatment of tuberculosis or as tumour adjuvant therapy, but its potential effect on diabetic nephropathy (DN) has not been studied. OBJECTIVE: To investigate the effect of RTT extract in renal fibrosis of DN. MATERIALS AND METHODS: C57BL/6 mice were randomly divided into four groups (n = 12). Diabetes mellitus (DM) mice were induced by streptozotocin (STZ, 55 mg/kg/day) for five consecutive days and treated by RTT extract (2 g/kg). Afterward, blood glucose, HE and Masson staining were assayed. The expression levels of Vimentin, É-SMA, TNF-É, NF-κB p-p65, NF-κB p65, SMYD2, H3K36me3, H3K4me3 were determined by western blots. Firbronectin was respectively assayed by western blot and immunofluorescent staining. RESULTS: RTT extract significantly ameliorated renal injury and renal fibrosis in the renal tissue of STZ-induced diabetic mice as demonstrated by the decreased expression level of Fibronectin (65%), Vimentin and α-SMA (75% & 53%). In addition, the levels of TNF-α (57%), NF-κB p-p65 and NF-κB p65 (35% & 25%) were elevated in the DN mice. Importantly, these were alleviated after RTT extract treatment. Moreover, we observed that the protein levels of SMYD2 (30%), H3K36me3 and H3K4me3 (53% & 75%) were reduced in DN mice after treatment with RTT extract. DISCUSSION AND CONCLUSIONS: RTT extract mediates antifibrotic effects and anti-inflammatory responses in STZ-induced DN mainly through suppressing SMYD2 activation and H3K36me3 and H3K4me3 protein expression. RTT extract might have therapeutic potential against high glucose-induced nephropathy.
Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Nefropatias Diabéticas/tratamento farmacológico , Extratos Vegetais/farmacologia , Ranunculus/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Glicemia/efeitos dos fármacos , Fibrose , Masculino , Camundongos , Camundongos Endogâmicos C57BL , EstreptozocinaRESUMO
Ranunculus muricatus L., an important member of family Ranunculaceae upon submission to phytochemical studies, led to the isolation of a novel natural hydrazine derivative, muricazine (1). Chemical structure of the compound was established with the aid of advanced spectroscopic techniques. It was evaluated for in vitro antioxidant, lipoxygenase, and urease (jack-bean) inhibitory activities. Results suggested that compound 1 could scavenge the DPPH free radical (42.1 ± 0.12 µM) to a great extent as compared to the standard (40.6 ± 0.91 µM). However, it showed moderate inhibitory potential against lipoxygenase (65.2 ± 0.45 µM) and urease (54.8 ± 0.23 µM) enzymes.
Assuntos
Inibidores Enzimáticos , Hidrazinas , Ranunculus , Antioxidantes , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Hidrazinas/química , Hidrazinas/farmacologia , Lipoxigenase , Inibidores de Lipoxigenase , Ranunculus/química , Urease/antagonistas & inibidoresRESUMO
Leishmaniasis and schistosomiasis are neglected tropical diseases (NTDs) infecting the world's poorest populations. Effectiveness of the current antileishmanial and antischistosomal therapies are significantly declining, which calls for an urgent need of new effective and safe drugs. In Ethiopia fresh leaves of Ranunculus multifidus Forsk. are traditionally used for the treatment of various ailments including leishmaniasis and eradication of intestinal worms. In the current study, anemonin isolated from the fresh leaves of R. multifidus was assessed for its in vitro antileishmanial and antischistosomal activities. Anemonin was isolated from the hydro-distilled extract of the leaves of R. multifidus. Antileishmanial activity was assessed on clinical isolates of the promastigote and amastigote forms of Leishmania aethiopica and L. donovani clinical isolates. Resazurin reduction assay was used to determine antipromastigote activity, while macrophages were employed for antiamastigote and cytotoxicity assays. Antischistosomal assays were performed against adult Schistosoma mansoni and newly transformed schistosomules (NTS). Anemonin displayed significant antileishmanial activity with IC50 values of 1.33 nM and 1.58 nM against promastigotes and 1.24 nM and 1.91 nM against amastigotes of L. aethiopica and L. donovani, respectively. It also showed moderate activity against adult S. mansoni and NTS (49% activity against adult S. mansoni at 10 µM and 41% activity against NTS at 1 µM). The results obtained in this investigation indicate that anemonin has the potential to be used as a template for designing novel antileishmanial and antischistosomal pharmacophores.
Assuntos
Antiprotozoários/farmacologia , Furanos/farmacologia , Leishmania/efeitos dos fármacos , Extratos Vegetais/farmacologia , Ranunculus/química , Schistosoma mansoni/efeitos dos fármacos , Animais , Antiprotozoários/química , Antiprotozoários/isolamento & purificação , Furanos/química , Furanos/isolamento & purificação , Testes de Sensibilidade Parasitária , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/químicaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Ranunculus japonicus Thunb. (short for R. japonicus) is a topically applied herb with the activities of removing jaundice, nebula and edema, preventing malaria, stopping asthma, promoting diuresis and relieving pain. It was firstly recorded in Zhouhou Beiji Fang and has been used for the treatment of malaria, ulcers, carbuncle, jaundice, migraine, stomachache, toothache and arthritis for over 1800 years. AIM OF THE STUDY: This study aimed to uncover the potentially effective components of R. japonicus and the pharmacological mechanisms against rheumatoid arthritis (RA) by combing LC-MS and network pharmacology. MATERIALS AND METHODS: Firstly, the chemical constituents of R. japonicus were qualitatively identified by UPLC-ESI-LTQ-Orbitrap MS. Then we performed target prediction by PharmMapper, protein-protein interaction (PPI) analysis via String, GO and KEGG pathway enrichment analysis by DAVID and constructed the compound-target-pathway network using Cytoscape. Thirdly, crucial compounds in the network were quantitatively analyzed to achieve quality control of R. japonicus. Finally, the pharmacological activities of R. japonicus and two potentially bioactive ingredients were validated in RA-FLSs (Rheumatoid Arthritis Fibroblast-like Synoviocytes) in vitro. RESULTS: Overall fifty-four ingredients of R. japonicus were identified and forty-five components were firstly discovered in R. japonicus. Among them, twenty-seven validated compounds were predicted to act on twenty-five RA-related targets and they might exhibit therapeutic effects against RA via positive regulation of cell migration, etc. Nine potentially bioactive components of R. japonicus which played important roles in the compound-target-pathway network were simultaneously quantified by an optimized UPLC-ESI-Triple Quad method. In vitro, compared to control group, R. japonicus extract, berberine and yangonin significantly inhibited the migration capacity of RA-FLSs after 24 h treatment. CONCLUSION: This study clarified that R. japonicus and the bioactive ingredients berberine and yangonin might exert therapeutic actions for RA via suppressing the aggressive phenotypes of RA-FLSs through combined LC-MS technology and network pharmacology tools for the first time. The present research provided deeper understanding into the chemical profiling, pharmacological activities and quality control of R. japonicus and offered reference for further scientific research and clinical use of R. japonicus in treating RA.
Assuntos
Artrite Reumatoide/tratamento farmacológico , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Farmacologia/métodos , Ranunculus/química , Movimento Celular/efeitos dos fármacos , Células Cultivadas , Cromatografia Líquida , Fibroblastos/efeitos dos fármacos , Humanos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Mapas de Interação de Proteínas/efeitos dos fármacos , Transdução de Sinais/efeitos dos fármacos , Sinoviócitos/efeitos dos fármacos , Espectrometria de Massas em Tandem , Cicatrização/efeitos dos fármacosRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: The members of the genus Ranunculus have counter-irritating properties and thus, they are traditionally used for treating anti-inflammatory disorders and other skin conditions. Ranunculus macrophyllus Desf. is a wild medicinal plant growing in Algeria and traditionally used to treat some cutaneous skin disorders. AIM: The aim of this study was to characterize the composition of the ethyl acetate and n-butanol extracts from Ranunculus macrophyllus Desf. as well as to elucidate and to compare their effect against acute skin inflammation. Moreover, both the antioxidant activity and the acute toxicity of the plant extracts were also studied. MATERIALS AND METHODS: Spectrophotometric and chromatographic methods were employed to identify and quantify phenolic compounds and triterpenoids from R. macrophyllus Desf. fractions. The antioxidant activity was estimated using the phosphomolebdenum, DPPH, reducing power and ß-carotene bleaching assays. The ethyl acetate and n-butanol extracts were screened for their anti-inflammatory activities using ex-vivo membrane stabilizing assays and in-vivo acute skin inflammation model. RESULTS: Ethyl acetate fraction showed the highest amounts of total phenolic compounds (413 ± 4 µg GAE/mg extract) and triterpenoids (70.4 ± 1.8 µg UAE/mg extract). Rutin, hesperidin, myricetin and kaempferol were the major compounds identified in the different fractions. Ethyl acetate fraction exhibited strong DPPH⢠radical scavenging ability (IC50 1.6 ± 0.2 µg/mL), high total antioxidant capacity (447 ± 7 µg AAE/mg extract) and reducing power (514 ± 8 µg AAE/mg extract). Ethyl acetate fraction inhibited (73.4 ± 0.3) % of linoleic acid peroxidation. Ethyl acetate and n-butanol fractions did not have any visible toxicity at 2000 mg/kg and presented excellent membrane stabilizing ability. The inhibition of xylene induced ear inflammation was (38 ± 4) % and (46 ± 1) % for RM-B and RM-EA, respectively. CONCLUSIONS: The high content of both phenolic compounds and triterpenoids combined with the remarkable anti-inflammatory effect and antioxidant activity of ethyl acetate and n-butanol extracts from R. macrophyllus Desf. support the wide spread use of this traditional plant on some skin disorders (inflammatory skin disorders).
Assuntos
Anti-Inflamatórios/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Ranunculus/química , 1-Butanol/química , Acetatos/química , Argélia , Animais , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Modelos Animais de Doenças , Feminino , Inflamação/tratamento farmacológico , Inflamação/patologia , Masculino , Camundongos , Fenóis/isolamento & purificação , Extratos Vegetais/químicaRESUMO
(1) Background: Ranunculus bulumei is a flowering plant that belongs to the Ranunculus species. Several Ranunculus species, such as R. aquatilis and R. muricatus, have traditionally been used to treat fever and rheumatism throughout Asia, suggesting that plants belonging to the Ranunculus species may have anti-inflammatory effects. To our knowledge, the pharmacological activity of R. bulumei has not been reported. Therefore, in this study, we aim to assess the anti-inflammatory activity of a methanol extract that was derived from R. bulumei (Rb-ME) in macrophage-mediated inflammatory responses and to identify the molecular mechanism that underlies any anti-inflammatory action. (2) Methods: The anti-inflammatory efficacy of Rb-ME was evaluated while using in vitro and in vivo experiments. The RAW264.7 cells and peritoneal macrophages were stimulated by lipopolysaccharide (LPS). In addition, LPS-induced peritonitis and HCl/EtOH-triggered gastritis models were produced. A nitric oxide (NO) assay, real-time PCR, luciferase reporter gene assay, western blot analysis, plasmid overexpression strategy, and in vitro kinase assay were used to determine the molecular mechanisms and target molecules of Rb-ME. The phytochemical active ingredients of Rb-ME were also identified by high performance liquid chromatograph (HPLC). (3) Results: Rb-ME reduced the production of NO and mRNA expression of iNOS, COX-2, IL-1ß, and IL-6 without cytotoxicity. The protein secretion of TNF-α and IL-6 was also decreased by Rb-ME. HPLC analysis indicates that quercetin, luteolin, and kaempferol are the main active ingredients in the anti-inflammatory efficacy of Rb-ME. Rb-ME also blocked MyD88-induced NF-κB promoter activity and nuclear translocation of NF-κB subunits (p65 and p50). Moreover, Rb-ME reduced the phosphorylation of IκBα, Akt, p85, Src, and Syk, which are NF-κB upstream signaling molecules in LPS-activated RAW264.7 cells. According to the in vitro kinase assay, Rb-ME directly inhibits Syk kinase activity. The oral administration of Rb-ME alleviated inflammatory responses and the levels of p-IκBα in mice with LPS-induced peritonitis and HCl/EtOH-induced gastritis. (4) Conclusions Rb-ME has anti-inflammatory capacity by suppressing NF-κB signaling and it has been found to target Src and Syk in the NF-κB pathway. Based on this efficacy, Rb-ME could be developed as an anti-inflammatory herbal medicine.
Assuntos
Metanol/química , NF-kappa B/metabolismo , Extratos Vegetais/farmacologia , Ranunculus/química , Transdução de Sinais/efeitos dos fármacos , Quinase Syk/metabolismo , Quinases da Família src/metabolismo , Animais , Anti-Inflamatórios/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Terapia de Alvo Molecular , Óxido Nítrico/biossíntese , Células RAW 264.7RESUMO
Ranunculus scleratus Linn. is used in folk medicine to treat hypertension. This study was aimed at providing validation to its traditional use and to explore underlying mechanisms of action. Effects of hydro-ethanolic crude extract of the plant and its fractions on blood pressure was evaluated using direct surgical method in normotensive and in fructose induced hypertensive rats. Various doses of crude extract, RSC, (5, 10, 20, 30mg/kg) and all fractions (3, 5, 10, 20mg/kg) were studied. Results suggested that aqueous fraction of R. scleratus (RSA) produced most pronounced effects at 10mg/kg in normotensive and at 20mg/kg in hypertensive animals. Underlying mechanisms, using various pharmacological antagonists were also elucidated. Results suggested the involvement of muscarinic receptor, angiotensin converting enzyme (ACE) inhibition, ganglionic block and nitric oxide (NO) release in presenting hypotensive response.
Assuntos
Anti-Hipertensivos/farmacologia , Pressão Sanguínea/efeitos dos fármacos , Hipertensão/tratamento farmacológico , Extratos Vegetais/farmacologia , Ranunculus , Inibidores da Enzima Conversora de Angiotensina/isolamento & purificação , Inibidores da Enzima Conversora de Angiotensina/farmacologia , Animais , Anti-Hipertensivos/isolamento & purificação , GMP Cíclico/metabolismo , Modelos Animais de Doenças , Frutose , Bloqueadores Ganglionares/isolamento & purificação , Bloqueadores Ganglionares/farmacologia , Hipertensão/induzido quimicamente , Hipertensão/metabolismo , Hipertensão/fisiopatologia , Antagonistas Muscarínicos/isolamento & purificação , Antagonistas Muscarínicos/farmacologia , Óxido Nítrico/metabolismo , Extratos Vegetais/isolamento & purificação , Ranunculus/química , Ratos Sprague-Dawley , Receptores Muscarínicos/metabolismo , Sistema Renina-Angiotensina/efeitos dos fármacosRESUMO
This study evaluates the antioxidant activity of Ranunculus muricatus and isolation and structure elucidation of the active constituents. The aerial parts of the plants were shade dried at room temperature and powdered and extracted with methanol. The free radical scavenging activity was evaluated by 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay. The percentage scavenging activity was determined based on the percentage of DPPH radical scavenged. Column chromatography was used in order to isolate the active compounds. Spectral techniques UV, IR, 1H NMR, 13CNMR and HREI-MS were used for the structure elucidation of the isolated compounds. Two isolated compounds, A (caffeoyl-ß-D-glucopyranoside) and B (1,3-dihydroxy-2-tetracosanoylamino-4-(E)-nonadecene), exibited a significant antioxidant activity as showed by DPPH radical scavenging method. Percentage inhibition for compound A (at 0.5 mM) was 82.67 ± 0.19 with IC50 of 93.25 ± 0.12 (µM), and for compound B (at 0.5 mM) was 69.23 ± 0.19 with IC50 of 183.34 ± 0.13 (µM). Quercetin was used as standard control. It was conclued from the present study that caffeoyl-ß-D-glucopyranoside and 1,3-dihydroxy-2-tetracosanoylamino-4-(E)-nonadecene isolated from methanol extract of aerial parts of Ranunculus muricatus posses antioxidant activity.
Assuntos
Ácidos Cafeicos/química , Ácidos Cafeicos/isolamento & purificação , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Ranunculus/química , Compostos de Bifenilo/química , Picratos/químicaRESUMO
Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(ω5Z)-etherolenoyl-2-O-dinor-(ω5Z)-etherolenoyl-3-O-ß-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-ß-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-ß-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-α-linolenoyl-3-O-ß-D-galactopyranosyl-sn-glycerol, and 1-O-(ω5Z)-etherolenoyl-2-O-palmitoyl-3-O-(α-galactopyranosyl-1-6-ß-D-galactopyranosyl)-sn-glycerol. The trivial names "linolipins E, F, G, H and I," respectively, have been ascribed to these novel complex oxylipins.
Assuntos
Oxilipinas/química , Oxilipinas/isolamento & purificação , Folhas de Planta/química , Ranunculus/químicaRESUMO
The Arctic flora hosts a limited number of species due to its extreme environmental conditions which also yield novel and unique secondary metabolites from withstanding plants. Considering a lack of research on bioactivity potential of Arctic flora, Ranunculus hyperboreus, an Arctic plant, was studied for its anti-inflammatory potential as a part of ongoing research on discovering novel natural bioactive products. Solvent-based fractions (H2O, n-BuOH, 85% aq. MeOH, n-hexane) from R. hyperboreus extract were observed to decrease the elevated nitrate amount during the inflammatory response of lipopolysaccharide-induced mouse macrophage RAW264.7 cells. To some extent, treatment with fractions was able to regulate the expression and protein levels of inflammation-related enzymes, iNOS and COX-2, and pro-inflammatory cytokines, TNF-α, IL-1ß, and IL-6. The most active fractions, H2O and 85% aq. MeOH, were suggested to exert their effect through suppressed activation of MAPK pathways, especially JNK. Based on the studies of same species, phenolic glycosides were suggested to be the main active ingredients. To our knowledge, this is the first report of any bioactivity of R. hyperboreus which could be a valuable source of natural bioactive agents against inflammation.
Assuntos
Anti-Inflamatórios/farmacologia , Glicosídeos/farmacologia , Lipopolissacarídeos/administração & dosagem , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Ranunculus/química , Animais , Anti-Inflamatórios/química , Citocinas/metabolismo , Regulação da Expressão Gênica/efeitos dos fármacos , Glicosídeos/química , Camundongos , Nitratos/metabolismo , Fenóis/química , Fenóis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Células RAW 264.7RESUMO
The aim of this work was to evaluate the phytochemical components, minerals, the antioxidant activity and total phenol contents of the essential oil from aerial parts of six major medicinal plants in Rayen, Iran. The plants included Ranunculus arvensis, Teucrium polium, Dracocephalum polychaetum, Kelussia odoratissima, Artemisia sieberi and Thymus kotschyanus. Total phenol content ranged from 0.03 to 0.158 mg/mL. A. sieberi showed the highest radical scavenging ability (IC50 = 94 µg/mL). The amount of minerals ranged as follows: P (0.23-29%), K (1.08-4.76%), Ca (0.78-2.35%), Mg (0.24-0.94%), Cu (8.3-15 mg/kg), Cd (0.7-1.1 mg/kg), Pb (2-11.7 mg/kg) and Fe (250-1280 mg/kg). A total of 79 compounds were identified across all plants. The main components studied in the plants were l-perillaldehyde, biosol, carvacrol, 1,8-cineol, terpinyl acetate and 1,2,3,6,7,7 a-hexahydro-5 h-inden 5-one.
Assuntos
Antioxidantes/farmacologia , Fenóis/análise , Plantas Medicinais/química , Antioxidantes/química , Artemisia/química , Cicloexanóis/análise , Cicloexanóis/farmacologia , Cimenos , Eucaliptol , Irã (Geográfico) , Minerais/análise , Monoterpenos/análise , Monoterpenos/farmacologia , Óleos Voláteis , Extratos Vegetais/química , Ranunculus/química , Thymus (Planta)/químicaRESUMO
Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-ß-d-fructofuranosylmethyl-furfural (2), 5-ß-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1-3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties.
Assuntos
Compostos Heterocíclicos/química , Ranunculus/química , Dicroísmo Circular , Compostos Heterocíclicos/isolamento & purificação , Estrutura Molecular , Raízes de Plantas/química , Teoria QuânticaRESUMO
Columbin (1) is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species. These species generally grow in Asia and Africa and have been used in folk medicine for their apparent analgesic and antipyretic activities. Columbin (1) is of particular interest due to its structural similarity to the known kappa-opioid receptor (KOR) agonist salvinorin A. Given that the KOR is of interest in the study of many serious diseases, such as anxiety, depression, and drug addiction, obtaining natural or semisynthetic molecules with KOR activity recently has gained much interest. For this reason, in the present study, derivatives of 1 were designed and synthesized using known structure-activity relationships of salvinorin A at KORs. The structures of the columbin analogues prepared were elucidated by NMR spectroscopy and mass spectroscopy, and their KOR activity was investigated in vitro by inhibition of forskolin-induced cAMP accumulation. Slight improvements in KOR activity were observed in columbin derivatives over their parent compound. However, despite the structural similarities to salvinorin A, neither columbin (1) nor its derivatives were potent KOR ligands. This work represents not only the first evaluation of columbin (1) at the KOR but also one of the first works to explore synthetic strategies that are tolerated on the columbin core.
Assuntos
Diterpenos Clerodânicos/química , Diterpenos/síntese química , Diterpenos/farmacologia , Lactonas/síntese química , Lactonas/farmacologia , Receptores Opioides kappa/agonistas , África , Analgésicos/farmacologia , Animais , Diterpenos/química , Diterpenos Clerodânicos/farmacologia , Lactonas/química , Ligantes , Estrutura Molecular , Ranunculus/química , Relação Estrutura-Atividade , Tinospora/químicaRESUMO
Buttercup (Ranunculus spp.) flowers are exceptional because they feature a distinct gloss (mirror-like reflection) in addition to their matte-yellow coloration. We investigated the optical properties of yellow petals of several Ranunculus and related species using (micro)spectrophotometry and anatomical methods. The contribution of different petal structures to the overall visual signal was quantified using a recently developed optical model. We show that the coloration of glossy buttercup flowers is due to a rare combination of structural and pigmentary coloration. A very flat, pigment-filled upper epidermis acts as a thin-film reflector yielding the gloss, and additionally serves as a filter for light backscattered by the strongly scattering starch and mesophyll layers, which yields the matte-yellow colour. We discuss the evolution of the gloss and its two likely functions: it provides a strong visual signal to insect pollinators and increases the reflection of sunlight to the centre of the flower in order to heat the reproductive organs.
Assuntos
Flores/química , Modelos Teóricos , Pigmentação , Epiderme Vegetal/química , Ranunculus/química , Flores/citologia , Flores/metabolismo , Óptica e Fotônica/métodos , Epiderme Vegetal/citologia , Epiderme Vegetal/metabolismo , Ranunculus/citologia , Ranunculus/metabolismoRESUMO
Phytochemical investigation of Ranunculus muricatus L. (Ranunculaceae) led to the isolation of a new metabolite named as ranuncoside from the ethyl acetate fraction of the plant. Structure of the novel compound was elucidated through detailed spectroscopic analyses, using UV, IR, 1H, 13C NMR and 2D NMR in combination with EIMS and HR EI-MS techniques. The compound was evaluated for antioxidant activity using the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay. Its inhibitory potential was tested against lipoxygenase and xanthine oxidase enzymes. Ranuncoside potently scavenged the DPPH free radicals (IC50 = 56.7 ± 0.43 µM) and strongly inhibited the activities of lipoxygenase (IC50 = 63.9 ± 0.17 µM) and xanthine oxidase (IC50 = 43.3 ± 0.22 µM).
Assuntos
Antioxidantes/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ranunculus/química , Animais , Antioxidantes/farmacologia , Inibidores Enzimáticos/análise , Inibidores Enzimáticos/farmacologia , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Glicosídeos/análise , Glicosídeos/farmacologia , Humanos , Inibidores de Lipoxigenase/isolamento & purificação , Extratos Vegetais/química , Xantina Oxidase/antagonistas & inibidoresRESUMO
The basic substances of life include various amino acids and sugars. To search such molecules is the precondition to understand the essential nature. Here we reported four unprecedented hybrids of γ-amino acids and sugars from the roots of Ranunculus ternatus, which possess potential tail to tail ether-connected (6,6-ether-connected) modes in the sugar moiety. The structures of these hybrids were elucidated by extensive analyses of spectra and calculated electronic circular dichroism (ECD) method.
Assuntos
Aminoácidos/química , Éter/química , Modelos Moleculares , Açúcares/química , Dicroísmo Circular , Estrutura Molecular , Ranunculus/químicaRESUMO
Ranunculus muricatus is commonly known as spiny fruit buttercup and is used in the treatment of intermittent fevers, gout and asthma. Qualitative analysis of phytochemicals of Ranunculus muricatus indicated the presence of saponins, tannins, phenols, flavonoids and alkaloids. Saponins were present in high amount as compared with other chemicals. Inorganic and heavy metals constituents were determined. Heavy metals estimation in the sample showed that iron was present in high amount followed by zinc even then the concentration of these metals is below acceptable limit. The physical parameters, antioxidant and antimicrobial activities of the extracts were determined. Acetone extract fraction showed optimal antioxidant activity as compared to ethanol and chloroform fractions of the candidate plant. The antimicrobial and antifungal activities of the crude extract and extract fractions were determined by well agar diffusion method. Highest zone of inhibitions were observed for crude extract followed by acetone extract fraction against Micrococcus luteus. Antifungal activities were high for crude extracts against Candida Albican. Findings of this study show that Ranunculus muricatus has a good medicinal impact.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Ranunculus/química , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/química , Candida albicans/efeitos dos fármacos , Candida albicans/crescimento & desenvolvimento , Testes de Sensibilidade a Antimicrobianos por Disco-Difusão , Micrococcus luteus/efeitos dos fármacos , Micrococcus luteus/crescimento & desenvolvimento , Picratos/química , Extratos Vegetais/isolamento & purificação , Solventes/químicaRESUMO
Foliar ionome, photosystem II activity, and leaf growth parameters of Ranunculus acris L., a potential biomonitor of trace element (TE) contamination and phytoavailability, were assessed using two riverbank soil series. R. acris was cultivated on two potted soil series obtained by mixing a TE (Cd, Cu, Pb, and Zn)-contaminated technosol with either an uncontaminated sandy riverbank soil (A) or a silty clay one slightly contaminated by TE (B). Trace elements concentrations in the soil-pore water and the leaves, leaf dry weight (DW) yield, total leaf area (TLA), specific leaf area (SLA), and photosystem II activity were measured for both soil series after a 50-day growth period. As soil contamination increased, changes in soluble TE concentrations depended on soil texture. Increase in total soil TE did not affect the leaf DW yield, the TLA, the SLA, and the photosystem II activity of R. acris over the 50-day exposure. The foliar ionome did not reflect the total and soluble TE concentrations in both soil series. Foliar ionome of R. acris was only effective to biomonitor total and soluble soil Na concentrations in both soil series and total and soluble soil Mo concentrations in the soil series B.
Assuntos
Monitoramento Ambiental/métodos , Complexo de Proteína do Fotossistema II/metabolismo , Folhas de Planta/efeitos dos fármacos , Ranunculus/efeitos dos fármacos , Poluentes do Solo/análise , Oligoelementos/análise , França , Folhas de Planta/química , Folhas de Planta/metabolismo , Ranunculus/química , Ranunculus/metabolismo , Poluentes do Solo/farmacologia , Oligoelementos/farmacologiaRESUMO
Ranunculus muricatus Linn. (RML) have been traditionally used for the treatment of various cardiovascular disorders. The aim of present study was to evaluate their cardiovascular effects in isolated perfused rabbit heart. The methanolic extract of RML was prepared by cold maceration process. The methanolic extract of RML (1 ng to 10 mg) was used to determine the percentage change in force of contraction (FC), heart rate (HR) and perfusion pressure (PP) by using Langendorff's Perfused Heart Apparatus. The PP, FC and HR of isolated rabbit heart were measured by power lab data acquisition system. Moreover, phytochemical analysis and acute toxicity study were also performed. The methanolic extract at the doses from I ng to 10 mg exhibited a significant increase in perfusion pressure and force of contraction. Moreover, the crude extract of RML revealed a significant increase in heart rate at doses from 1 ng to µg. The maximum rise in all the thee parameters was observed at 1 µg and 1 ng, respectively In another study, the melhanoliC extract was tested in the presence of propranolol and verapamil on isolated perfused rabbit heart. The study shown that the increase in HR and FC produced by the plant extracts was significantly reduced in the presence of propranolol whereas PP remained significantly raised even in the presence of propranolol. However, in the presence of verapamil, this increased PP was significantly reversed to a decrease while a significant positive inotropic and chronotropic effects were observed. It is concluded that the cardiotonic activity of methanolic extract of RML might be due certain cardio active chemical compounds. Further studies are needed to isolate these pharmacologically active phytochemical constituents and elucidate their exact mechanism of action.