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Nomilin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-N3004

  • Specification : 98%

  • CAS number : 1063-77-0

  • Formula : C28H34O9

  • Molecular Weight : 514.56

  • PUBCHEM ID : 46783795

  • Volume : 25mg

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Catalogue Number

BF-N3004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

514.56

Appearance

White crystalline powder

Botanical Source

Citrus aurantium,Citrus medica,Citrus medica var. sarcodactylis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)OC1CC(=O)OC(C2C1(C3CCC4(C(OC(=O)C5C4(C3(C(=O)C2)C)O5)C6=COC=C6)C)C)(C)C

Synonyms

fromcitrusseeds/1-(Acetyloxy)-1,2-dihydroobacunoic Acid e-Lactone/Oxireno[4',5']pyrano[4',3':5,6]naphth[2,1-c]oxepin-3,10,12(1H,4H,10aH)-trione, 5-(acetyloxy)-8-(3-furanyl)decahydro-1,1,5a,7a,11b-pentamethyl-, (5S,5aR,5bR,7aS,8S,10aS,11aR,11bR,13aR)-/(5S,5aR,5bR,7aS,8R,10aS,11aR,11bR,13aR)-8-(furan-3-yl)-1,1,5a,7a,11b-pentamethyl-3,10,12-trioxohexadecahydrooxireno[4,4a]isochromeno[6,5-g][2]benzoxepin-5-yl acetate/(5S,5aR,5bR,7aS,8S,10aS,11aR,11bR,13aR)-8-(3-Furyl)-1,1,5a,7a,11b-pentamethyl-3,10,12-trioxohexadecahydrooxireno[4,4a]isochromeno[6,5-g][2]benzoxepin-5-yl acetate/1-(3-Furyl)decahydro-11-hydroxy-4b,7,7,11a,13a-pentamethyloxireno(4,4a)-2-benzopyrano[6,5-g](2)benzoxepin-3,5,9(3aH,4bH,6H)-trione Acetate

IUPAC Name

[(1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icosan-13-yl] acetate

Density

1.3±0.1 g/cm3

Solubility

Flash Point

351.6±31.5 °C

Boiling Point

657.7±55.0 °C at 760 mmHg

Melting Point

278-279°

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1063-77-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

21839074

Abstract

Angiogenesis is a crucial step in the growth and metastasis of cancers. Antiangiogenic activity of nomilin was studied using in vivo as well as in vitro models. Nomilin significantly inhibited tumor directed capillary formation. Serum proinflammatory cytokines such as IL-1β, IL-6, TNF-α and GM-CSF and also serum NO levels were significantly reduced by the treatment of nomilin. Administration of nomilin significantly reduced the serum level of VEGF, a proangiogenic factor and increased the antiangiogenic factors IL-2 and TIMP-1. In vitro studies using rat aortic ring assay showed that administration of nomilin at non-toxic concentrations significantly inhibited microvessel sprouting. Studies using human umbilical vein endothelial cells clearly demonstrated that administration of nomilin significantly retarded endothelial cell proliferation, migration, invasion and tube formation. These data clearly demonstrate the antiangiogenic potential of nomilin by downregulating the activation of MMPs, production of VEGF, NO and proinflammatory cytokines as well as upregulating IL-2 and TIMP.
Copyright © 2011 Elsevier B.V. All rights reserved.

Title

Nomilin Inhibits Tumor-Specific Angiogenesis by Downregulating VEGF, NO and Proinflammatory Cytokine Profile and Also by Inhibiting the Activation of MMP-2 and MMP-9

Author

Poyil Pratheeshkumar 1 , Girija Kuttan

Publish date

2011 Oct 15

PMID

31389456

Abstract

Oxidative stress is considered to play an important role in the cerebral ischemia-reperfusion injury. The nuclear transcription factor erythroid-2-related factor 2 (Nrf2)/NAD(P)H dehydrogenase [quinone] 1 (NQO1) pathway has been considered as a potential target for neuroprotection in cerebral ischemia-reperfusion injury. Nomilin (NOM) is a limonoid compound obtained from the extracts of citrus fruits. The purpose of our study was to determine whether NOM could exert beneficial effects in cerebral ischemia-reperfusion rats. Firstly, NOM treatment significantly mitigated cell death and decreased lactate dehydrogenase (LDH) release and ROS production in SH-SY5Y cells induced by oxygen-glucose deprivation (OGD), which was almost abolished by Nrf2 knockdown. Secondly, NOM improved infarct area, brain edema and neurological deficits in an experimental stroke rat model via middle cerebral artery occlusion (MCAO). Furthermore, NOM attenuated blood-brain barrier (BBB) disruption in MCAO rats, which might be associated with alleviating the loss of tight junction proteins, including ZO-1 and occludin-5. Further results revealed that NOM treatment effectively mitigated oxidative stress and facilitated the expressions of Nrf2 and NQO1, which might confirm that the loss of tight junction proteins in the microvasculature was likely mediated by oxidative stress. In conclusion, our study provided evidence that the protective effects of NOM in cerebral ischemia-reperfusion rats were related to the Nrf2/NQO1 pathway.

Title

Nomilin Protects Against Cerebral Ischemia-Reperfusion Induced Neurological Deficits and Blood-Brain Barrier Disruption via the Nrf2 Pathway

Author

Yu-Sheng Shi 1 , Yan Zhang 2 , Bin Liu 2 , Chun-Bin Li 1 , Jiao Wu 1 , Yang Li 1

Publish date

2019 Sep 1

PMID

26544116

Abstract

Nomilin is a potential anticancer agent. In this study, a rapid, sensitive, and simple ultra-performance liquid chromatography with tandem mass spectrometry methodology was established and validated to quantify nomilin in rat plasma. Plasma samples were prepared through liquid-liquid extraction using ethyl acetate. Chromatographic separation was performed using an Acquity HSS T3 column. Acetonitrile and water containing 0.1% (v/v) formic acid were used as mobile phases at a flow rate of 0.3 mL/min. Nomilin and quercetin (internal standard) were detected and quantified via a triple quadrupole tandem mass spectrometer in the positive ion mode with multiple reaction monitoring. Tandem mass spectrometry detection was performed by monitoring the fragmentations of m/z 515.3 → m/z 161.0 and m/z 303.2 → m/z 153.1 of nomilin and quercetin, respectively. Good linearity (R(2) > 0.996) was observed in the concentration range of 1 ng/mL to 500 ng/mL with a lower limit of quantification of 1 ng/mL for nomilin. The average extraction recoveries of nomilin and quercetin were > 82.3% and 82.0%, respectively. Intra- and interday precisions were less than 15% and accuracy ranged from 85.0% to 90.1%. Indeed, the proposed method was successfully applied to analyze the pharmacokinetics of nomilin after 3 and 50 mg/kg nomilin were administered to rats via intravenous and oral routes, respectively.
Georg Thieme Verlag KG Stuttgart · New York.

Title

A Rapid, Selective and Sensitive UPLC-MS/MS Method for Quantification of Nomilin in Rat Plasma and Its Application in a Pharmacokinetic Study

Author

Yuepiao Cai 1 , Shuangshuang Zhang 1 , Qiqi Wang 1 , Hao Sun 1 , Mi Zhou 1 , Shuping Hu 1 , Zheng Xiang 1

Publish date

2016 Feb


Description :

Nomilin as an anti-obesity and anti-hyperglycemic agent. PUMID/DOI:23374727 Vitam Horm. 2013;91:425-39. Recent scientific findings support the notion that bile acids, which are cholesterol catabolites, are bioactive signaling molecules that function as ligands for the farnesoid X receptor or a G-protein-coupled receptor, TGR5. Through these receptors, bile acids can maintain not only bile acid homeostasis but also lipid and carbohydrate homeostasis. An intriguing finding regarding the role of TGR5 in energy metabolism and glucose homeostasis suggests a potential approach to combat obesity and insulin resistance by targeting this receptor to increase thermogenesis and incretin secretion. In this review, I have summarized the latest findings related to TGR5 agonists, in particular, a citrus limonoid, Nomilin, and the roles of these agonists in energy metabolism and glucose homeostasis. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9. PUMID/DOI:21839074 Eur J Pharmacol. 2011 Oct 15;668(3):450-8. Angiogenesis is a crucial step in the growth and metastasis of cancers. Antiangiogenic activity of Nomilin was studied using in vivo as well as in vitro models. Nomilin significantly inhibited tumor directed capillary formation. Serum proinflammatory cytokines such as IL-1β, IL-6, TNF-α and GM-CSF and also serum NO levels were significantly reduced by the treatment of Nomilin. Administration of Nomilin significantly reduced the serum level of VEGF, a proangiogenic factor and increased the antiangiogenic factors IL-2 and TIMP-1. In vitro studies using rat aortic ring assay showed that administration of Nomilin at non-toxic concentrations significantly inhibited microvessel sprouting. Studies using human umbilical vein endothelial cells clearly demonstrated that administration of Nomilin significantly retarded endothelial cell proliferation, migration, invasion and tube formation. These data clearly demonstrate the antiangiogenic potential of Nomilin by downregulating the activation of MMPs, production of VEGF, NO and proinflammatory cytokines as well as upregulating IL-2 and TIMP. Nomilin inhibits metastasis via induction of apoptosis and regulates the activation of transcription factors and the cytokine profile in B16F-10 cells. PUMID/DOI:21665879 Integr Cancer Ther. 2012 Mar;11(1):48-60. Nomilin is a triterpenoid present in common edible citrus fruits with putative anticancer properties. In this study, the authors investigated the antimetastatic potential of Nomilin and its possible mechanism of action. Metastasis was induced in C57BL/6 mice through the lateral tail vein using highly metastatic B16F-10 melanoma cells. Administration of Nomilin inhibited tumor nodule formation in the lungs (68%) and markedly increased the survival rate of the metastatic tumor-bearing animals. These results correlated with the biochemical parameters and histopathological analysis. Nomilin showed an inhibition of tumor cell invasion and activation of matrix metalloproteinases. Treatment with Nomilin induced apoptotic response, characterized by an increase in the sub-G1 fraction of cells with chromatin condensation and membrane blebbing, a typical ladder of DNA fragmentation, and detection of apoptotic cells by TUNEL assay. Nomilin treatment also exhibited a downregulated Bcl-2 and cyclin-D1 expression and upregulated p53, Bax, caspase-9, caspase-3, p21, and p27 gene expression in B16F-10 cells. Proinflammatory cytokine production and gene expression were found to be downregulated in Nomilin-treated cells. The study also reveals that Nomilin could inhibit the activation and nuclear translocation of antiapoptotic transcription factors such as nuclear factor (NF)-κB, CREB, and ATF-2 in B16F-10 cells. Contents and antioxidant capacity of limonin and nomilin in different tissues of citrus fruit of four cultivars during fruit growth and maturation. PUMID/DOI:DOI: 10.1016/j.foodchem.2004.10.037 Food Chemistry, 2005, 93(4):599-605. The contents of limonin and Nomilin in different fruit tissues of Foxiangyou (Citrus grandis), Citrus unshiu, Penggan (Citrus reticulata) and Huyou (Citrus changshanensis KS Chen et CX Fu) were measured during fruit growth and maturation by HPLC (high performance liquid chromatography). Results showed that limonin and Nomilin were the predominant limonoids in the extracted samples. During fruit growth and maturation, the contents of limonin and Nomilin increased from April, peaked in early September and decreased afterwards until late October when they reached a steady low level. The antioxidant capacities of limonin and Nomilin in the four tissues of mature fruit were determined by beta-carotene bleaching assay. The results showed that the antioxidant capacities of limonin and Nomilin varied in different tissues and cultivars. In the three tissues other than albedo, the antioxidant capacities of limonin and Nomilin were high (2.9-8.3 times than that of vitamine C). Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. PUMID/DOI:14648393 Planta Med. 2003 Oct;69(10):910-3. In the last years several plant-derived natural compounds have been screened for their anti-HIV activity in order to find lead compounds with novel structures or mechanisms of action. Among these, several triterpenoids have been found to exhibit an antiretroviral activity with different mechanisms of action. In this study the effect of two limonoids, limonin and Nomilin, on the growth of human immunodeficiency virus-1 (HIV-1) in culture of human peripheral blood mononuclear cells (PBMC) and on monocytes/macrophages (M/M) is described. Limonin and Nomilin were found to inhibit the HIV-1 replication in all cellular systems used. A dose-dependent inhibition of viral replication was observed in PBMC isolated from healthy donors and infected with HIV-1 strain after incubation with limonin and Nomilin (EC (50) values: 60.0 microM and 52.2 microM, respectively). The two terpenoids inhibited at all concentrations studied the production of HIV-p24 antigen even when the PBMC employed were chronically infected (EC (50) values of 61.0 microM for limonin and 76.2 microM for Nomilin). Moreover, these compounds inhibited the HIV-1 replication even in infected M/M. In this cellular system the inhibitory effect was significant at the concentrations of 20 microM, 40 microM and 80 microM starting from day 14 and reached the maximum effect after 18 days of incubation. As regards the mechanism of action, limonin and Nomilin inhibit in vitro HIV-1 protease activity. In general, the results obtained point out a similar anti-HIV activity of limonin and Nomilin indicating that this activity is not drastically influenced by the structural difference between the two compounds. Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system. PUMID/DOI:13678231 Phytomedicine. 2003;10(6-7):483-9. The effect of naturally occurring triterpenoid compounds such as glycyrrhizic acid, ursolic acid, oleanolic acid, and Nomilin on the immune system was studied using Balb/c mice. Intraperitoneal treatments with 5 doses of these terpenoid compounds were found to enhance the total white blood cells (WBC) count. In ursolic acid, oleanolic acid and Nomilin treated animals the maximum total WBC count was observed on the 6th day, while in glycyrrhizic acid treated animals it was observed o