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1.
Zhongguo Zhong Yao Za Zhi ; 48(17): 4598-4609, 2023 Sep.
Artículo en Zh | MEDLINE | ID: mdl-37802799

RESUMEN

Alkaloids are important active ingredients occurring in many traditional Chinese medicines, and alkaloid glycosides are one of their existence forms. The introduction of saccharide units improves the water solubility of alkaloid glycosides thus presenting better biological activity.Because of the low content in plants, alkaloid glycosides have been not comprehensively studied. In this study, ultrahigh performance liquid chromatography-quadrupole time of flight-tandem mass spectrometry(UPLC-QTOF-MS/MS) was employed to identify and analyze the alkaloid glycosides in Coptis chinensis, Phellodendron chinense, Menispermum dauricum, Sinomenium acutum, Tinospora sagittata and Stephania tetrandra. The results showed that except Tinospora sagittata, the other five herbal medicines contained alkaloid glycosides. Furthermore, the alkaloid glycosides in each herbal medicine were identified based on UV absorption spectra, quasimolecular ion peaks in MS, fragment ions information in the MS/MS, and previous literature reports. A total of 42 alkaloid glycosides were identified. More alkaloid glycosides were identified in C. chinensis and Menispermum dauricum, and eleven in C. chinensis were potential new compounds. Furthermore, the alkaloid glycosides in the water extract of C. chinensis were coarsely se-parated by macroporous adsorption resin, purified by column chromatography with D151 cation exchange resin, ODS and MCI, combined with semi-preparative high performance liquid chromatography. Two new alkaloid glycosides were obtained, and their structures were identified by mass spectrometry and NMR data as(S)-7-hydroxy-1-(p-hydroxybenzyl)-2,2-N,N-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-O-ß-D-glucopyranoside and(S)-N-methyltetrahydropalmatubine-9-O-ß-D-glucopyranoside, respectively. This study is of great significance for enriching the information about the chemical composition and the in-depth development of C. chinensis. Meanwhile, it can provide a reference for rapid identification and isolation of alkaloid glycosides from other Chinese herbal medicines.


Asunto(s)
Alcaloides , Antineoplásicos , Coptis , Medicamentos Herbarios Chinos , Plantas Medicinales , Glicósidos/química , Medicina Tradicional China , Espectrometría de Masas en Tándem/métodos , Coptis chinensis , Medicamentos Herbarios Chinos/química , Alcaloides/análisis , Extractos Vegetales/química , Plantas Medicinales/química , Agua , Cromatografía Líquida de Alta Presión/métodos , Coptis/química
2.
Chem Biodivers ; 19(6): e202200334, 2022 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-35561089

RESUMEN

Three new alkaloids (1-3), one new diphenyl ether (4) and fifteen known alkaloids (5-19) were isolated from the rattan stems of Sinomenium acutum. Comprehensive analyses of HR-ESI-MS, 1D (1 H and 13 C), 2D-NMR (1 H-1 H COSY, HSQC, HMBC, NOESY), circular dichroism (CD), UV and IR revealed the structures and absolute configurations of these new compounds. The structures of other compounds were determined by comparison of their 1 H and 13 C-NMR data with previous literature reports. By measuring the amount of NO produced, the anti-inflammatory properties of the isolated compounds were studied. The results showed that compounds 4 and 5 had strong NO inhibitory activity.


Asunto(s)
Alcaloides , Artritis Reumatoide , Medicamentos Herbarios Chinos , Alcaloides/química , Alcaloides/farmacología , Artritis Reumatoide/tratamiento farmacológico , China , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Medicina Tradicional , Estructura Molecular , Sinomenium/química
3.
Int J Med Sci ; 15(8): 758-764, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-30008584

RESUMEN

PURPOSE: Recent studies have reported the anti-inflammatory effect of Sinomenium acutum. We investigated the anti-inflammatory effect of sinomenine on endotoxin-induced uveitis in a rat model. METHODS: Endotoxin-induced uveitis was induced in rat by lipopolysaccharide (LPS) immunization. Sinomenine (50mg/kg and 100mg/kg) was administered at 30 minutes before, 6 hours and 12 hours after LPS immunization. Clinical and histological severity was evaluated. Protein concentration and levels of tumor necrosis factor (TNF)-α and prostaglandin (PG)-E2 in aqueous humor were measured. Expression of activated Nuclear factor (NF)-κB p65 in ciliary body was also observed. RESULTS: Clinical and histological severities were significantly milder in sinomenine-treated rat than in controls (P < 0.001). Sinomenine suppressed protein leakage and down-regulated the production of TNF-α and PG-E2 in a dose-dependent manner. Sinomenine treatment suppressed the translocation of the NF-κB p65 subunit into the nuclei. CONCLUSION: Systemic administration of sinomenine suppressed the inflammation of ocular tissues. These findings suggest that sinomenine could be a novel therapeutic agent for the control of endogenous ocular inflammatory disease.


Asunto(s)
Antiinflamatorios/farmacología , Extractos Vegetales/farmacología , Sinomenium , Uveítis/tratamiento farmacológico , Animales , Humor Acuoso , Modelos Animales de Enfermedad , Endotoxinas , Lipopolisacáridos , Masculino , FN-kappa B/efectos de los fármacos , FN-kappa B/metabolismo , Ratas , Ratas Endogámicas Lew , Factor de Necrosis Tumoral alfa , Uveítis/inmunología
4.
J Asian Nat Prod Res ; 20(3): 195-200, 2018 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-28503941

RESUMEN

Two pyrrolo[2,1-a]isoquinolines (1 and 2) and three pyrrole alkaloids (3-5), including three new ones, named sinopyrines A-C (1-3), were isolated from the 95% EtOH extract of the stems and rhizomes of Sinomenium acutum (Thumb.) Rehd. et Wils. The structures of the new compounds were elucidated on the basis of spectroscopic data. This is the first report of pyrrole-bearing natural compounds from the family Menispermaceae.


Asunto(s)
Alcaloides/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Isoquinolinas/aislamiento & purificación , Pirroles/aislamiento & purificación , Sinomenium/química , Alcaloides/química , Medicamentos Herbarios Chinos/química , Isoquinolinas/química , Estructura Molecular , Tallos de la Planta/química , Pirroles/química , Rizoma/química
5.
Molecules ; 23(7)2018 07 04.
Artículo en Inglés | MEDLINE | ID: mdl-29973556

RESUMEN

The characterization of alkaloids is challenging because of the diversity of structures and the complicated fragmentation of collision induced structural dissociation in mass spectrometry. In this study, we analyzed the alkaloids in Sinomenium acutum (Thunb.) Rehderet Wil by high resolution mass spectrometry. Chromatographic separation was achieved on a Phenomenex Kinetex C18 (2.1 mm × 100 mm, 2.6 µm) column with a mobile phase consisting of acetonitrile and water (0.1% formic acid) under gradient elution. A total of 52 alkaloids were well separated and 45 of them were structurally characterized, including morphinans, aporphines, benzylisoquinolines, and protoberberines. Specially, mass spectrometric study of the morphinan alkaloids were explicitly investigated. Electrostatic potential plot from simulation was calculated for determination of protonation sites. Further fragmentation analysis suggested that the C3H7N, CH4O, and H2O elimination was displayed in MS² spectrum. These fragmentation pathways are universal for morphinan alkaloids having methoxy substituted cyclohexenone or cyclohexadienone moieties. Additionally, for nitrogen oxides, an ion-neutral complex intermediate is involved in the fragmentation process, generating additional oxygenated ions. All these results provided the universal rules of fragmentation used for detection of alkaloids, and will be expected to be highly useful for comprehensive study of multi-components in the herbal medicine analysis.


Asunto(s)
Alcaloides/química , Alcaloides/aislamiento & purificación , Sinomenium/química , Cromatografía Liquida , Espectrometría de Masas , Modelos Moleculares , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación
6.
Fitoterapia ; 172: 105713, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37949304

RESUMEN

The chemical structure of sinoacutine is formed by a phenanthrene nucleus and an ethylamine bridge. Because it has a similar parent structure to morphine, it is subdivided into morphinane. At present, all reports have pointed out that the basic skeleton of morphine alkaloids is salutaridine (the isomer of sinoacutine), which is generated by the phenol coupling reaction of (R)-reticuline. This study shows that the biosynthetic precursors of sinoacutine and salutaridine are different. In this paper, the sinoacutine synthetase (SinSyn) gene was cloned from Sinomenium acutum and expressed SinSyn protein. Sinoacutine was produced by SinSyn catalyzed (S)-reticuline, according to the results of enzyme-catalyzed experiments. The optical activity, nuclear magnetic resonance, and mass spectrum of sinoacutine and salutaridine were analyzed. The classification and pharmacological action of isoquinoline alkaloids were discussed. It was suggested that sinoacutine should be separated from morphinane and classified as sinomenine alkaloids.


Asunto(s)
Alcaloides , Morfinanos , Estructura Molecular , Morfinanos/química , Morfinanos/metabolismo , Morfinanos/farmacología , Alcaloides/farmacología , Derivados de la Morfina
7.
Curr Med Chem ; 2024 Sep 18.
Artículo en Inglés | MEDLINE | ID: mdl-39297453

RESUMEN

In this manuscript, the resource distribution, pharmacological activity, pharma-cokinetics of sinomenine and the structure, synthesis, biological activity and mechanism of sinomenine derivatives reported from 2000 to December 2023 were reviewed. The lit-erature was retrieved through Web of Science, PubMed, Science Direct, SciFiner Scholar and other websites. Sinomenine belongs to isoquinoline alkaloids and was extracted from the Chinese herb Sinomenium acutum root. In Asian countries such as China and Japan, it is commonly prescribed as a treatment for rheumatoid arthritis. In addition, sinomenine also has sedative, analgesic, anti-inflammatory, immunosuppressive, neuroprotective, an-ti-drug dependence, anti-tumor and other biological activities. Sinomenine limited its ap-plication prospects because of its large dosage, poor epidermal permeability and short half-life. To overcome these defects, new sinomenine derivatives have been synthesized. Based on the comprehensive analysis of relevant literature at home and abroad, this paper reviews the recent progress in the study of sinomenine's pharmacological effects and structural modifications. Future research on sinomenine will focus on improving its thera-peutic effect, and developing new drug preparations and structural modifications. It is hoped that this review will help to better understand the research progress of sinomenine and provide constructive suggestions for further research of sinomenine.

8.
J Nat Med ; 78(1): 226-235, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37656375

RESUMEN

From the methanolic extract of the climbing stems and rhizomes of Sinomenium acutum, two new aporphine analogues, acutumalkaloids I and II, were isolated together with fifteen known compounds including lysicamine. The chemical structures of the isolated new compounds were elucidated based on chemical/physicochemical evidence such as NMR and MS spectra. For acutumalkaloids I and II, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. We compared anti-proliferative activities of isolated compounds with reported naturally occurring Wnt/ß-catenin pathway inhibitor, nuciferine. Among the isolated compounds, we found lysicamine have anti-proliferative activity against both of HT-29 human colon cancer cell line and its cancer stem cells (CSCs). The IC50 values of lysicamine against non-CSCs and its CSCs were lower than that of nuciferine. In addition, the results of western blotting analysis suggested that lysicamine inhibited the expression of Wnt/ß-catenin pathway target protein such as survivin. These results suggested that lysicamine show cytotoxic activity via inhibition of Wnt/ß-catenin pathway.


Asunto(s)
Alcaloides , Antineoplásicos , Neoplasias , Humanos , Sinomenium/química , beta Catenina , Rizoma/química , Alcaloides/química , Antineoplásicos/farmacología , Vía de Señalización Wnt , Células Madre Neoplásicas , Línea Celular Tumoral
9.
Luminescence ; 28(4): 468-73, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23390128

RESUMEN

A simple and rapid capillary electrophoresis (CE) with an acidic potassium permanganate chemiluminescence (CL) detection method was developed to determine three alkaloids (curine, sinomenine and magnoflorine) simultaneously. A laboratory-built CE-CL detection interface was used. The field-amplified sample stacking technique was applied to the online concentration of alkaloids. Experimental conditions for CE separation and CL detection were investigated in detail to acquire optimum conditions. Under optimal conditions, the three alkaloids were baseline separated within 6 min, and the detection limits (S/N = 3) ranged from 0.03 µg/mL to 0.49 µg/mL. This method was successfully applied to determine the above three alkaloids in Sinomenium acutum, and the result of the determination of sinomenine was in good agreement with those given by high-performance liquid chromatography and CE methods. In addition, a possible CL reaction mechanism of sinomenine-KMnO4-H2SO4 was proposed.


Asunto(s)
Alcaloides/análisis , Mediciones Luminiscentes , Permanganato de Potasio/química , Sinomenium/química , Electroforesis Capilar , Luminiscencia , Estructura Molecular
10.
Drug Des Devel Ther ; 17: 691-706, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-36915642

RESUMEN

Background: Rheumatoid arthritis (RA) is a chronic inflammatory disease of the joints associated with systemic comorbidities. Sinomenium acutum is regarded as an effective traditional Chinese medicine (TCM) for the treatment of RA. Materials and Methods: Based on network pharmacology and Gene Expression Omnibus (GEO) database, 33 RA-related differentially-expressed genes (DEGs) targeting active compounds of Sinomenium acutum were initially screened in our investigation. Results: Gene Ontology (GO) and Kyoto encyclopaedia of genes and genome (KEGG) analyses found the important involvement of these DEGs in osteoclast differentiation, and finally 5 core DEGs, including NCF4, NFKB1, CYBA, IL-1ß and NCF1 were determined through protein-protein interaction (PPI) network. We also identified the related active component of Sinomenium acutum include Stigmasterol. Finally, in order to experimentally verify these results, a rat model of collagen-induced arthritis (CIA) was established, and subsequently treated with Stigmasterol solution. Conclusion: Similar to the healing effect of Indomethacin, Stigmasterol was observed to reduce the levels of inflammatory factors (IL-6 and IL-1ß) and osteoclast differentiation-related factors (RANKL, ACP5 and Cathepsin K), which can also reduce the arthritis index score and alleviate the degree of pathological injury of rat ankle joints. The predictions and experimental data uncover the involvement of Stigmasterol, an active component of Sinomenium acutum, in regulation of osteoclast differentiation, exerting great medicinal potential in the treatment of RA.


Asunto(s)
Artritis Experimental , Artritis Reumatoide , Medicamentos Herbarios Chinos , Ratas , Animales , Estigmasterol , Farmacología en Red , Artritis Reumatoide/tratamiento farmacológico , Artritis Reumatoide/metabolismo , Mapas de Interacción de Proteínas , Medicina Tradicional China , Artritis Experimental/tratamiento farmacológico , Artritis Experimental/patología , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/uso terapéutico
11.
Fitoterapia ; 165: 105404, 2023 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-36572115

RESUMEN

Six new alkaloids (1-6) and six known alkaloids (7-12) were obtained from the stems of Sinomenium acutum. Among them, compounds 1-3 and 6 were four N-oxide alkaloids. The structures and absolute configurations of these new alkaloids were elucidated through comprehensive data of 1D and 2D NMR, HRESIMS and ECD spectra. All isolated compounds were evaluated in vitro for their inhibitory activities against nitric oxide (NO) production and inhibitory effects on AChE. Among them, the sinomenine N-oxide (9) was the most potent NO production inhibitor, with an IC50 value of 23.04 µM.


Asunto(s)
Alcaloides , Medicamentos Herbarios Chinos , Sinomenium/química , Óxidos , Estructura Molecular , Alcaloides/farmacología , Alcaloides/química , Medicamentos Herbarios Chinos/farmacología
12.
Front Mol Biosci ; 10: 1065171, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-36923645

RESUMEN

Objective: To investigate and predict the targets and signaling pathways of sinomenium acutum (SA) in the treatment of rheumatoid arthritis (RA) through systems biology and network pharmacology, and to elucidate its possible mechanisms of action. Methods: We screened the active ingredients and corresponding target proteins of SA in Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform (TCMSP), Traditional Chinese Medicines Integrated Database (TCMID) and Bioinformatics Analysis Tool for Molecular mechANism of Traditional Chinese Medicine (BATMAN); and obtained the targets of rheumatoid arthritis diseases in a database of gene-disease associations (DisGeNET), Online Mendelian Inheritance in Man (OMIM) database. The two targets were mapped by Venn diagram and the intersection was taken. The intersecting targets were used to construct protein-protein interaction (PPI) network maps in the String database, and Metascape was used for Gene Ontology (GO) functional annotation and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment. Finally, the molecular docking technique was applied to validate and further clarify the core target of SA for the treatment of rheumatoid arthritis. Results: A total of six active ingredients and 217 potential targets were obtained after screening; 2,752 rheumatoid arthritis-related targets and 66 targets common to RA and SA. GO function and KEGG pathway enrichment analysis yielded 751 GO function entries (652 GO biological processes, 59 GO molecular functions and 40 GO cellular components) and 77 KEGG signaling pathways. It mainly involves pathways related to neural activity ligand-receptor interaction pathways, cancer pathways, calcium signaling channels, Th17 cell differentiation and others, which are mainly classified into four categories, including regulation of immunity, anti-inflammation, regulation of cell growth and apoptosis, and signaling. The molecular docking results showed that the binding energy of PTGS2, CASP3, JUN and PPARG to the key components beta-sitosterol, 16-epi-Isositsirikine, Sinomenine and Stepholidine were ≤ -6.5 kcal/mol, suggesting the existence of molecular binding sites. Conclusion: SA acts on key targets such as PTGS2, CASP3, JUN, and PPARG to modulate signaling pathways such as neural activity ligand-receptor interaction, cancer, calcium ion, NF-κB, and Th17 cell differentiation to regulate immunity, anti-inflammation, modulation of cell cycle, bone metabolism, and signaling for the treatment of RA. It was also confirmed that the treatment of RA with SA has multi-component, multi-target, multi-pathway and multi-mechanism characteristics.

13.
Pharmaceuticals (Basel) ; 17(1)2023 Dec 20.
Artículo en Inglés | MEDLINE | ID: mdl-38275992

RESUMEN

Sinomenium acutum (SA) has long been used as a traditional medicine in China, Japan, and Korea to treat a wide range of diseases. It has been traditionally used to ameliorate inflammation and improve blood circulation. However, its role in platelet activation has not been thoroughly investigated. Hence, we conducted this study to assess the potential inhibitory effect of SA on platelet aggregation and thrombus formation. The antiplatelet activities of SA were evaluated by assessing platelet aggregation, granular secretion, intracellular Ca2+ mobilization, and the Glycoprotein (GP) VI-mediated signalosome. The thrombosis and bleeding time assays were used to investigate the effect of SA (orally administered at 50 and 100 mg/kg for seven days) in mice. SA treatment at concentrations of 50, 100, and 200 µg/mL significantly reduced GPVI-mediated platelet aggregation, granular secretion, and intracellular Ca2+ mobilization. Further biochemical studies revealed that SA inhibited spleen tyrosine kinase, phospholipase Cγ2, phosphatidylinositol 3-kinase, and AKT phosphorylation. Interestingly, oral administration of SA efficiently ameliorated FeCl3-induced arterial thrombus formation without prolonging the tail bleeding time. These findings suggest that SA has beneficial effects in thrombosis and hemostasis. Therefore, SA holds promise as an effective therapeutic agent for the treatment of thrombotic diseases.

14.
Chin Herb Med ; 15(2): 278-283, 2023 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-37265762

RESUMEN

Objective: The population density and diversity of Sinomenium acutum (Menispermaceae) have been greatly reduced recently by overharvesting for medicinal purposes in China. Therefore, it is urgent that the remaining populations are investigated, and that strategies for the utilization and conservation of this species are developed. This study aimed to find the possible glacial refugia and define the genetic diversity of S. acutum for its proper utilization and conservation. Methods: A total of 77 S. acutum samples were collected from four locations, Qinling Mountains, Daba Mountains, Dalou Mountains, and Xuefeng Mountains, in subtropical China. Genetic diversity among and between these populations were phylogenetically analyzed using four chloroplast DNA molecular markers (atpI-atpH, trnQ-5'rps16, trnH-psbA and trnL-trnF). Results: A total of 14 haplotypes (C1 to C14) were found in collected samples. Haplotypes C1 and C3 were shared among all populations, with C3 as the ancestral haplotype. Haplotypes C11 and C12 diverged the most from C3 and other haplotypes. No obvious phylogeographic structure was found in four locations using the GST/NST test. There is no evidence of rapid demographic expansion in S. acutum based on the mismatch distribution, and the results of Tajima's D test, and Fu's FS test. Our analyses of molecular variance revealed a high level of genetic variation within populations. In contrast, the genetic differentiation among S. acutum populations was low, indicating frequent gene flow. Conclusion: Xuefeng, Dalou, and Daba Mountains were possible glacial refugia for the populations of S. acutum. C1, C3, C11 and C12 haplotypes of S. acutum should be carefully preserved and managed for their genetic value.

15.
Am J Chin Med ; 50(5): 1219-1253, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35681262

RESUMEN

Sinomenium acutum is the dry stem of Sinomenium acutum (Thunb.) Rehd et Wils. (S. acutum) and Sinomenium acutum (Thunb.) Rehd. et Wils. var. cinereum Rehd. et Wils and is mainly distributed in China and Japan. As a traditional Chinese medicine (TCM) for dispelling wind and dampness in China, it is widely distributed and has a long history of drug use. In recent years, with the increase of the incidence of rheumatoid disease, S. acutum has become the focus of research. This paper reviews the literature on the chemical constituents, pharmacological effects, clinical applications and pharmacokinetics and safety of S. acutum from the past 60 years. At present, more than 210 natural compounds have been isolated from S. acutum, including alkaloids, lignans, triterpenoid saponins, steroids, and other structures. Pharmacological activities of S. acutum were mainly reported on anti-inflammatory, analgesic, anti-allergic, immunosuppressive, anti-tumor, liver-protective, anti-oxidative, and other effects, and clinical applications were mainly recorded on rheumatoid arthritis, ankylosing spondylitis, and other diseases. The clinical use of SIN has fewer side effects and more safety; only a small number of gastrointestinal reactions occurred, and the symptoms disappeared after the drug stopped. The purpose of this paper is to lay a foundation and provide reference for the follow-up research and wide application of S. acutum.


Asunto(s)
Alcaloides , Artritis Reumatoide , Botánica , Medicamentos Herbarios Chinos , Alcaloides/uso terapéutico , Antiinflamatorios no Esteroideos , Artritis Reumatoide/tratamiento farmacológico , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/uso terapéutico , Humanos , Sinomenium/química
16.
Front Plant Sci ; 13: 1086335, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-36605968

RESUMEN

Benzylisoquinoline alkaloids (BIAs) are a large family of plant natural products with important pharmaceutical applications. Sinomenium acutum is a medicinal plant from the Menispermaceae family and has been used to treat rheumatoid arthritis for hundreds of years. Sinomenium acutum contains more than 50 BIAs, and sinomenine is a representative BIA from this plant. Sinomenine was found to have preventive and curative effects on opioid dependence. Despite the broad applications of S. acutum, investigation on the biosynthetic pathways of BIAs from S. acutum is limited. In this study, we comprehensively analyzed the transcriptome data and BIAs in the root, stem, leaf, and seed of S. acutum. Metabolic analysis showed a noticeable difference in BIA contents in different tissues. Based on the study of the full-length transcriptome, differentially expressed genes, and weighted gene co-expression network, we proposed the biosynthetic pathways for a few BIAs from S. acutum, such as sinomenine, magnoflorine, and tetrahydropalmatine, and screened candidate genes involved in these biosynthesis processes. Notably, the reticuline epimerase (REPI/STORR), which converts (S)-reticuline to (R)-reticuline and plays an essential role in morphine and codeine biosynthesis, was not found in the transcriptome data of S. acutum. Our results shed light on the biogenesis of the BIAs in S. acutum and may pave the way for the future development of this important medicinal plant.

17.
J Pharm Biomed Anal ; 220: 115005, 2022 Oct 25.
Artículo en Inglés | MEDLINE | ID: mdl-36087496

RESUMEN

Sinomenium acutum stem is widely used to treat rheumatoid arthritis, gout, ankylosing spondylitis and other diseases in China. However, its metabolism in vivo is still unclear. In this study, UPLC-Q-TOF/MS was used to analyze the main components and their metabolites in rats after oral administration of Sinomenium acutum stem extract. A total of 41 compounds were identified from the ethanol extract of Sinomenium acutum stem based on the established database and the reference substance; a total of 25 prototype components and 107 metabolites (74 phase I metabolites and 33 phase II metabolites) were speculated and identified in the plasma, urine, bile and feces of rats administered. The metabolic pathways included hydroxylation, demethylation, dehydrogenation, glucuronidation and acetylation. In conclusion, this study revealed the metabolism of Sinomenium acutum stem in vivo, which may provide a better basis for the study of Sinomenium acutum stem and provide useful chemical information on the material basis and pharmacological mechanism of drug efficay.


Asunto(s)
Alcaloides , Medicamentos Herbarios Chinos , Administración Oral , Alcaloides/análisis , Animales , Bilis/metabolismo , Cromatografía Líquida de Alta Presión , Medicamentos Herbarios Chinos/química , Etanol/análisis , Heces/química , Ratas , Sinomenium
18.
Curr Pharm Des ; 28(26): 2140-2149, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35331092

RESUMEN

The advanced era has invited a plethora of chronic and autoimmune infirmities unmistakably dominated by rheumatoid arthritis, occurring because of equivocal causes, including ecological factors, genetic variations, etc. Unfortunately, it is winning pretty much in every stratum of the society in the undefined age group of the population. Engineered drugs are accessible for the treatment; however, they do experience adverse effects as the treatment requires a prolonged duration worsened by noncompliance. To overwhelm it, certain pharmacological and molecular pathways are explored in the wake of Chinese herbs that prompted the prevention of this deteriorating autoimmune disease. The alcoholic extracts and decoctions are procured from Chinese herbs, such as Paeonia lactiflora, Glycyrrhiza uralensis, Tripterygium wilfordii, etc., which have been proved to manifest constructive pharmacological actions. The activities that were exhibited by extracts are significantly innocuous, non-toxic, and potent to fix the affliction in contrast with the chemosynthetic drugs. Therefore, these Chinese herbs bring forth potent anti-inflammatory, immune-suppressing, anti-nociceptive, anti-neovascularizing, free radical scavenging activities, and various other benefits to withstand several pathological events that usually endure infirmity. It can be abridged that Chinese herbs possess assorted and selective therapeutic properties with profound safety and viability to treat this rheumatic disorder. Thus, this review aims to shed light on naturally originated treatment that is pertinent to providing invulnerable therapy exonerating from adverse effects by restraining joint deformities, production of auto-antibodies, and inflammation.


Asunto(s)
Artritis Reumatoide , Medicamentos Herbarios Chinos , Plantas Medicinales , Artritis Reumatoide/tratamiento farmacológico , China , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/uso terapéutico , Humanos , Tripterygium
19.
Phytochemistry ; 200: 113244, 2022 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-35597314

RESUMEN

Eleven previously undescribed alkaloids, named sinometumines A-K, along with three known alkaloids, were isolated from the rhizomes of Sinomenium acutum. The chemical structures of these unreported compounds were established using extensive spectroscopic methods (IR, UV, HRESIMS, and NMR), and their absolute configurations were determined by single crystal X-ray diffraction analyses and calculated electronic circular dichroism spectroscopy (ECD). Sinometumine D was the first aporphine-type derived alkaloid inner salt with a rearranged dibenzofuran ring backbone. Sinometumine E was a rare protoberberine-type alkaloid with a complex 6/6/6/6/6/6 hexacyclic skeleton. This was the first report of alkaloids with these two skeletons isolated from S. acutum. All isolates were evaluated for their inhibitory activities against indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO). Lysicamine possessed noteworthy inhibitory activities as an IDO1/TDO dual inhibitor with IC50 values of 6.22 ± 0.26 µM and 23.76 ± 2.93 µM, respectively, and liriodenine revealed moderate dual inhibition with IC50 values of 31.65 ± 4.44 µM and 15.64 ± 0.26 µM. The intermolecular interactions and binding modes between lysicamine and IDO1/TDO were elaborated by molecular docking studies.


Asunto(s)
Alcaloides , Antineoplásicos , Alcaloides/química , Antineoplásicos/química , Simulación del Acoplamiento Molecular , Estructura Molecular , Rizoma/química , Sinomenium/química
20.
Mitochondrial DNA B Resour ; 5(3): 2992-2993, 2020 Jul 25.
Artículo en Inglés | MEDLINE | ID: mdl-33458029

RESUMEN

We generated the complete chloroplast genome sequence of Sinomenium acutum, a species of the Menispermaceae family, and characterized from the de novo assembly of Illumina HiSeq paired-end sequencing data. The total length of the chloroplast genome of S. acutum was 162,787 bp with a large single-copy (LSC) region of 91,430 bp, a small single-copy (SSC) region of 21,245 bp, and a pair of identical inverted repeat regions (IRs) of 25,056 bp. The total of 131 genes were annotated in the chloroplast genome of Sinomenium acutum, including 85 protein-coding genes, 38 transfer RNA (tRNA) genes, and 8 ribosomal RNA (rRNA) genes. The phylogenetic analysis of S. acutum with 18 related species revealed the closest taxonomical relationship with Menispermum dauricum in the Menispermaceae family.

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