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Cheilanthifoline

$1,076

  • Brand : BIOFRON

  • Catalogue Number : BD-P0275

  • Specification : 98.0%(HPLC)

  • CAS number : 483-44-3

  • Formula : C19H19NO4

  • Molecular Weight : 325.364

  • PUBCHEM ID : 440582

  • Volume : 25mg

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Catalogue Number

BD-P0275

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

325.364

Appearance

Powder

Botanical Source

Structure Type

Miscellaneous

Category

SMILES

COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O

Synonyms

IUPAC Name

(13S)-17-methoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol

Applications

Anti-inflammatory, Anti-bacterial and Anti-acetylcholinesterase Activities of two Isoquinoline Alkaloids Scoulerine and Cheilanthifoline PUMID/DOI:Phurpa Wangchuk, Thanapat Sastraruji, Malai Taweechotipatr,?. Anti-inflammatory, Anti-bacterial and Anti-acetylcholinesterase Activities of two Isoquinoline Alkaloids Scoulerine and Cheilanthifoline[J]. Natural Product Communications, 2016, 11(12):1801-1804. Phurpa Wangchuk, Thanapat Sastraruji, Malai Taweechotipatr,等. Anti-inflammatory, Anti-bacterial and Anti-acetylcholinesterase Activities of two Isoquinoline Alkaloids Scoulerine and Cheilanthifoline[J]. Natural Product Communications, 2016, 11(12):1801-1804. Corydalis plants containing isoquinoline alkaloids are reported to possess promising pharmacological properties for the treatment of important diseases including cancer, inflammation, Alzheimer's disease and microbial infections. As part of a wider program investigating Bhutanese medicinal plants, we have previously identified eight isoquinoline alkaloids from C. dubia. Out of these, we report here on two of the major alkaloids, scoulerine (1) and cheilanthifoline (2) and their inhibitory activities against acetylcholinesterase (anti-AChE), tumor necrosis factor alpha (anti TNF-alpha) and a bacterial strain, Helicobacter pylori. Both alkaloids showed weak anti TNF-alpha and antibacterial activities. However, the anti-AChE activity of scoulerine (1) was promising as it significantly inhibited AChE with a minimum inhibitory requirement (MIR) value of 0.0015 nmol, which was two-fold better than the reference drug, galanthamine (MIR value of 0.003 nmol). As there are limited anti-Alzheimer's chemotherapeutics, scoulerine (1) is worthy of further exploration, including lead optimization, structure-activity-relationship studies, analog development, pharmacodynamics and in vivo animal studies. Anti-osteoclastogenic effects of isoquinoline alkaloids from the rhizome extract of Sinomenium acutum PUMID/DOI:DOI: 10.1007/s12272-016-0734-8 Arch Pharm Res. 2016 May;39(5):713-20. A phytochemical investigation for the rhizome extract from Sinomenium acutum (Menispermaceae) resulted in the isolation of several active principles responsible for the anti-osteoclastogenic property of the extract, together with related isoquinoline alkaloids (1-13) including two new compounds, 1 and 2. Among isolated compounds, salutaridine (7), dauricumine (10), cheilanthifoline (12), and dauriporphine (13) were observed to give significant inhibitions on receptor activator of nuclear factor-kappa B ligand-induced differentiation of mouse bone marrow-derived macrophages into multinucleated osteoclasts, respectively. The chemical structures of two newly isolated compounds, 1 and 2 were established as 8-demethoxycephatonine (1) and 7(R)-7,8-dihydrosinomenine (2), by spectroscopic analyses including 2D NMR experiments. Study on alkaloids from Corydalis saxicola and their anti-oxidative activities PUMID/DOI: Zhi-Chao H E, Wang D M, Guo-Cheng L I, et al. Study on alkaloids from Corydalis saxicola and their anti-oxidative activities[J]. Chinese Traditional & Herbal Drugs, 2014, 45(11):1526-1531. Objective To study the alkaloids from Corydalis saxicola and their anti-oxidative activities. Methods The alkaloids were separated and purified by various column chromatography and identified according to their spectral analyses. The anti-oxidation activities were investigated on DPPH radical scavenging assay. Results Sixteen compounds were obtained and identified as cavidine (1),stylopine (2),canadine (3), tetrahydropalmatine (4),cheilanthifoline (5),scoulerine (6),protopine (7),dehydrocheilanthifoline (8), dehydroisoapocavidine (9),berberine (10), dehydrodiscretamine (11),chelerythrine (12),dehydrocavidine (13), corypalline (14), isocorydine (15), and pallidine (16). The alkaloids from C. saxicla were measured by the model of scavenging the stable DPPH radical, which showed a concentration dependent scavenging effect. Conclusion Compounds 3, 5, 8,11,and 16 are isolated from C. saxicola for the first time. Compounds 5 and 16 show the strong anti-oxidative activities. Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia PUMID/DOI:DOI:10.1016/j.jep.2012.06.037 J Ethnopharmacol. 2012 Aug 30;143(1):310-3. Ethnopharmacological relevance: Corydalis dubia is used in Bhutanese traditional medicine as a febrifuge and for treating infections in the blood, liver and bile which correlate to the signs and symptoms of malarial and microbial infections. Aim of the study: To validate the ethnopharmacological uses of the plant and to discover potential new therapeutic drug leads. Materials and methods: C. dubia was collected from Bhutan and the alkaloids were obtained using acid base fractionation and separation by repeated column and preparative plate chromatography. The alkaloids were identified from analysis of their physiochemical and spectroscopic data and were tested for antiplasmodial, antimicrobial and cytotoxicity activities. Results: A systematic extraction and isolation protocol yielded one new natural product, dubiamine, and seven known isoquinoline alkaloids, scoulerine, cheilanthifoline, protopine, capnoidine, bicuculline, corydecumbine and hydrastine. Among the four alkaloids tested, scoulerine showed the best antiplasmodial activity with IC50 values of 5.4 mu M and 3.1 mu M against the antifolate sensitive and the multidrug resistant P. falciparum strains: TM4/8.2 and K1CB1, respectively. None of the alkaloids tested showed significant antimicrobial or cytotoxicity activities. Conclusions: The antiplasmodial test results, of the isolated alkaloid components, are commensurated with the ethnopharmacological uses of this plant. (C) 2012 Elsevier Ireland Ltd. All rights reserved.

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C19H19NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1

InChl Key

FVXCQULKSPVRPK-HNNXBMFYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:483-44-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31801112

Abstract

The long noncoding RNA NR2F1-AS1 has been found to promote the development of hepatocellular carcinoma and endometrial cancer. In this study, we measured NR2F1-AS1 expression in osteosarcoma (OS), determined the involvement of NR2F1-AS1 in the malignant properties of OS, and investigated the underlying mechanisms. NR2F1-AS1 was found to be upregulated in OS tumors and cell lines. The increased NR2F1-AS1 level was closely associated with advanced clinical stage and distant metastasis in patients with OS. Patients with OS in an NR2F1-AS1 high-expression group demonstrated significantly shorter overall survival than did patients in an NR2F1-AS1 low-expression group. NR2F1-AS1 knockdown inhibited OS cell proliferation, migration, and invasion and promoted cell cycle arrest and apoptosis in vitro and slowed tumor growth in vivo. NR2F1-AS1 was found to function as a competing endogenous RNA by directly sponging microRNA-483-3p (miR-483-3p) and upregulating its target oncogene forkhead box A1 (FOXA1). Finally, rescue experiments revealed that knockdown of miR-483-3p and recovery of FOXA1 expression both attenuated the influence of the NR2F1-AS1 knockdown on OS cells. Thus, NR2F1-AS1 plays an oncogenic role in OS through sponging miR-483-3p and thereby upregulating FOXA1, suggesting an additional target for osteosarcoma therapeutics.

KEYWORDS

NR2F1-AS1, microRNA-483-3p, forkhead box A1, osteosarcoma therapy

Title

Long noncoding RNA NR2F1-AS1 enhances the malignant properties of osteosarcoma by increasing forkhead box A1 expression via sponging of microRNA-483-3p

Author

Shenglong Li,corresponding author1 Ke Zheng,1 Yi Pei,1 Wei Wang,1 and Xiaojing Zhang1

Publish date

2019 Dec 15

PMID

30602302

Abstract

Objective:
Calcific aortic valve disease (CAVD), characterized by aortic valve (AV) sclerosis and calcification, is a major cause of death in the aging population; however, there are no effective medical therapies other than valve replacement. AV calcification preferentially occurs on the fibrosa-side, exposed to disturbed flow (d-flow), while the ventricularis-side exposed to predominantly stable flow (s-flow) remains protected by unclear mechanisms. Here, we tested the role of novel flow-sensitive ubiquitin E2 ligase-C (UBE2C) and microRNA-483-3p (miR-483) in flow-dependent AV endothelial function and AV calcification.

Approach and Results:
Human AV endothelial cells (HAVECs) and fresh porcine AV (PAV) leaflets were exposed to s-flow or d-flow. We found that UBE2C was upregulated by d-flow in HAVECs in the miR-483-dependent manner. UBE2C mediated OS-induced endothelial inflammation and endothelial-mesenchymal-transition (EndMT) by increasing the hypoxia-inducible factor1α (HIF1α) level. UBE2C increased HIF1α by ubiquitinating and degrading its upstream regulator von Hippel-Lindau (pVHL). These in vitro findings were corroborated by immunostaining studies using diseased human AV leaflets. Additionally, we found that reduction of miR-483 by d-flow led to increased UBE2C expression in HAVECs. The miR-483 mimic protected against endothelial inflammation and EndMT in HAVECs and calcification of PAV leaflets by downregulating UBE2C. Moreover, treatment with the HIF1α inhibitor (PX478) significantly reduced PAV calcification in static and d-flow conditions.

Conclusions:
These results suggest that miR-483 and UBE2C are novel flow-sensitive anti- and pro-CAVD molecules, respectively, that regulate the HIF1α pathway in AV. The miR-483 mimic and HIF1α pathway inhibitors may serve as potential therapeutics of CAVD.

KEYWORDS

Flow, AV endothelial cells, Ubiquitination, Inflammation, EndMT, AV calcification, miR-483, UBE2C, pVHL, HIF1α

Title

Disturbed flow increases UBE2C via loss of miR-483-3p, inducing aortic valve calcification by the HIF1α pathway in endothelial cells

Author

Joan Fernandez Esmerats,1 Nicolas Villa-Roel,1 Sandeep Kumar,1 Lina Gu,1 Md Tausif Salim,2 Michael Ohh,3 W. Robert Taylor,1,4 Robert M. Nerem,5 Ajit P. Yoganathan,1,2 and Hanjoong Jo1,4,†

Publish date

2020 Mar 1.

PMID

29375378

Abstract

The long-term survival rate of hepatocellular carcinoma (HCC) is poor. One of the reasons for the poor rate of survival is the high rate of recurrence caused by intrahepatic metastas is that adversely affects long-term outcome. Many studies have indicated that microRNAs play an important role in HCC, but there has been no research of clonal origins on recurrent HCC (RHCC) by analzing microRNAs. In the present study, we found that miR-483-5p was significantly upregulated in RHCC tissues of short-term recurrence (≤ 2 years) by miRNA microarray screening, and can significantly promote migration and invasion of HCC cells in vitro and increase intrahepatic metastasis in nude mice in vivo. Furthermore, we demonstrated that activated leukocyte cell adhesion molecule (ALCAM), which significantly suppressed migration and invasion of HCC cells, was a direct target of miR-483-5p, and the re-introduction of ALCAM expression could antagonize the promoting effects of miR-483-5p on the capacity of HCC cells for migration and invasion. In addition, expression level of ALCAM was negatively correlated with microvascular invasion and tumor size recognized as prognostic factors. The cases which were negative for ALCAM expression had shorter time to recurrence than positive cases, and univariate and multivariate survival analyses showed that ALCAM was an independent risk factor of HCC recurrence. qRT-PCR and Western blotting showed that the expression of EMT related genes (MMP-2, MMP-9, E-caherin and vimentin) significantly changed as a result of interfering or overexpression of ALCAM, and ALCAM was significantly associated with EMT in HCC. These results suggest that the miR-483-5p/ALCAM axis is an important regulator in invasion and metastasis and biomarker for recurrence risk assessment of HCC.

KEYWORDS

ALCAM, miR-483-5p, hepatocellular carcinoma, early recurrence, invasion and metastasis, EMT

Title

Predicting Value of ALCAM as a Target Gene of microRNA-483-5p in Patients with Early Recurrence in Hepatocellular Carcinoma

Author

Xin-Yuan Lu,1,2,3,†‡ Di Chen,4,‡ Xiao-Yuan Gu,5,‡ Jie Ding,4 Ying-Jun Zhao,4 Qian Zhao,1,2,3 Ming Yao,6 Zhiao Chen,4,* Xiang-Huo He,4,* and Wen-Ming Cong1,2,3,*

Publish date

2017;