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Bergamottin

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-B4005

  • Specification : 98%(HPLC)

  • CAS number : 7380-40-7

  • Formula : C21H22O4

  • Molecular Weight : 338.4

  • PUBCHEM ID : 5471349

  • Volume : 25mg

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Catalogue Number

BF-B4005

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

338.4

Appearance

White crystal

Botanical Source

Notopterygium incisum

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCCC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)C)C

Synonyms

4-([(2E)-3,7-dimethyl-2,6-octadienyl]oxy)-7h-furo[3,2-g]chromen-7-one/4-{[(2E)-3,7-dimethyl-2,6-octadienyl]oxy}-7H-furo[3,2-g]chromen-7-one/Bergamottin/Bergaptin/5-geranyloxypsoralen/Bergamotine/4-{[(2'E)-3',7'-dimethyl-2',6'-octadienyl]oxy}-7H-furo[3,2-g][1]benzopyran-7-one/4-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one/4-{[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one/5-Geranoxypsoralen/Bergomottin/5-geranyloxypsolaren/7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-/7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-/Bergamotin

IUPAC Name

4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Petroleum ether

Flash Point

258.4±30.1 °C

Boiling Point

503.7±50.0 °C at 760 mmHg

Melting Point

75-80ºC

InChl

InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+

InChl Key

DBMJZOMNXBSRED-OQLLNIDSSA-N

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#:7380-40-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30558157

Abstract

Cancer still remains one of the leading causes of death worldwide. In spite of significant advances in treatment options and the advent of novel targeted therapies, there still remains an unmet need for the identification of novel pharmacological agents for cancer therapy. This has led to several studies evaluating the possible application of natural agents found in vegetables, fruits, or plant-derived products that may be useful for cancer treatment. Bergamottin is a furanocoumarin derived from grapefruits and is also a well-known cytochrome P450 inhibitor. Recent studies have demonstrated potent anti-oxidative, anti-inflammatory, and anti-cancer properties of grapefruit furanocoumarin both in vitro and in vivo. The present review focuses on the potential anti-neoplastic effects of bergamottin in different tumor models and briefly describes the molecular targets affected by this agent.

KEYWORDS

bergamottin; cancer; chemoprevention; phytochemicals

Title

Pharmacological Utilization of Bergamottin, Derived from Grapefruits, in Cancer Prevention and Therapy.

Author

Ko JH1,2, Arfuso F3, Sethi G4, Ahn KS5,6.

Publish date

2018 Dec 14

PMID

29614883

Abstract

Obesity is a serious and increasing health problem worldwide, and the inhibition of adipogenesis is considered to be a potential therapeutic target for it. Bergamottin (BGM), a component of grapefruit juice, has been reported to regulate lipolysis. However, the physiological role of BGM in obesity has not been evaluated so far. In the present study, we investigated the effects of BGM on obesity in 3T3-L1 cells and in mice fed a high-fat diet (HFD). BGM inhibited adipogenic differentiation of 3T3-L1 cells along with a significant decrease in the lipid content by downregulating the expression of two critical adipogenic factors, CCAAT enhancer-binding protein-alpha (C/EBP[Formula: see text]) and peroxisome proliferator activated receptor-gamma (PPAR[Formula: see text]). The expressions of target proteins such as adipocyte fatty acid-binding protein (aP2), adiponectin, and resistin were also decreased by BGM. It activated AMP-activated protein kinase (AMPK) by increasing phosphorylation of AMPK and the downstream target acetyl-CoA carboxylase (ACC), indicating that BGM exerted its antiadipogenic effect through AMPK activation. In the HFD-induced obese mouse model, BGM administration significantly reduced the weight and sizes of white adipose tissue as well as the weight gain of mice fed HFD. Moreover, UCP1 and PGC1[Formula: see text] expressions, well-known as brown adipocyte marker genes, were higher in the BGM-treated HFD mice than that in the HFD-induced obese mice. This study suggests that BGM suppress adipogenesis by AMPK activation in vitro and reduces body weight in vivo.

KEYWORDS

AMPK; Adipogenesis; Bergamottin; High-Fat Diet; Obesity

Title

Bergamottin Inhibits Adipogenesis in 3T3-L1 Cells and Weight Regulation in Diet-Induced Obese Mice.

Author

Ko JH1, Nam D1, Um JY1, Jung SH2, Ahn KS1,2.

Publish date

2018

PMID

28566583

Abstract

Nowadays, a lot of food ingredients are marketed as dietary supplements for health. Because the effectiveness and mechanisms of these compounds have not been fully characterized, they might have unknown functions. Therefore, we investigated the effect of several food ingredients (Bergamottin, Chrysin, L-Citrulline and β-Carotene) known as health foods on adipocyte differentiation by using 3T3-L1 preadipocytes. In this study, we found that Bergamottin, a furanocoumarin isolated from grapefruit juice, promotes adipocyte differentiation. In addition, Bergamottin increases the expression of adiponectin, an anti-inflammatory adipokine, and peroxisome proliferator activated receptor γ (PPARγ), a nuclear receptor regulating adipocyte differentiation. Furthermore, the anti-inflammatory activity of Bergamottin was demonstrated by its inhibition of the activation of nuclear factor-κB (NF-κB), an inflammatory transcription factor. Stimulation of mature 3T3-L1 adipocytes by tumor necrosis factor-α (TNF-α) decreased the expression of the endogeneous NF-κB inhibitor, IκBα. Treatment with Bergamottin further decreased the TNF-α-induced change in IκBα expression, suggesting that Bergamottin mediated the inhibition of NF-κB activation. In addition, Bergamottin decreased the TNF-α-induced increase in the mRNA levels of pro-inflammatory adipokines, monocyte chemoattractant protein-1 and interleukin-6. Taken together, our results show that Bergamottin treatment could inhibit inflammatory activity through promoting adipocyte differentiation, which in turn suggests that Bergamottin has the potential to minimize the risk factors of metabolic syndrome.

KEYWORDS

Bergamottin; adipocyte; inflammation; obesity

Title

Bergamottin Promotes Adipocyte Differentiation and Inhibits Tumor Necrosis Factor-α-induced Inflammatory Cytokines Induction in 3T3-L1 Cells.

Author

Mizuno H1, Hatano T1, Taketomi A1, Kawabata M1, Nakabayashi T1.

Publish date

2017


Description :

Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM.