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Fargesin

$576

  • Brand : BIOFRON

  • Catalogue Number : BF-F3002

  • Specification : 98%

  • CAS number : 31008-19-2

  • Formula : C21H22O6

  • Molecular Weight : 370.4

  • PUBCHEM ID : 10926754

  • Volume : 20mg

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Catalogue Number

BF-F3002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

370.4

Appearance

White crystalline powder

Botanical Source

Yulania biondii,Illicium simonsii,Chrysanthemum indicum,Piper austrosinense,Zanthoxylum simulans

Structure Type

Lignanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)OC

Synonyms

Fargesin/1,3-Benzodioxole, 5-[(1S,3aR,4R,6aR)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-/5-[(1S,3aR,4R,6aR)-4-(3,4-Dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole/(+)-demethoxyaschantin/methyl piperitol/(+)-kobusin/Methyl pluviatilol

IUPAC Name

5-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole

Density

1.3±0.1 g/cm3

Solubility

Methanol; Acetontrile; Ethyl Acetate; DMSO

Flash Point

208.9±30.0 °C

Boiling Point

506.4±50.0 °C at 760 mmHg

Melting Point

132.0 to 136.0 °C

InChl

InChI=1S/C21H22O6/c1-22-16-5-3-12(7-18(16)23-2)20-14-9-25-21(15(14)10-24-20)13-4-6-17-19(8-13)27-11-26-17/h3-8,14-15,20-21H,9-11H2,1-2H3/t14-,15-,20-,21+/m0/s1

InChl Key

AWOGQCSIVCQXBT-LATRNWQMSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:31008-19-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30956031

Abstract

Background: Fargesin is commonly used in the treatment of allergic rhinitis, inflammation, sinusitis and headache.
Objective: The aim of the study is to investigate a new function of fargesin against melanin production and its underlying molecular mechanism.
Methods: B16F10 mouse melanoma cells, Melan-a and human epidermal melanocytes were treated with different concentrations of fargesin for the indicated time. The extracellular and cellular melanin content was detected by spectrometry at 490 nm and 405 nm, respectively. RT-qPCR and Western blot analysis were used to exam the expression of melanogenic enzymes and the activities of PKA/CREB and p38 MAPK pathway components. Zebrafish was used as an in vivo model for studying the function of fargesin in regulating melanogenesis.
Results: Fargesin effectively inhibited melanin production at moderate dose in mouse B16F10 melanoma cells, normal melanocyte cell lines and zebrafish. The expression of microphthalmia-associated transcription factor (MITF), its downstream melanogenic enzymes and tyrosinase activity were also strongly reduced by fargesin. Moreover, the increase of melanin production induced by UVB and forskolin could be fully reversed by fargesin treatment. Fargesin also effectively inhibited the activation of PKA/CREB and p38 MAPK as well as their interactions, which in turn is responsible for the expression of MITF and melanogenic enzymes.
Conclusions: These results show that fargesin can function as an anti-melanogenic agent, at least in part, by inhibiting PKA/CREB and p38/MAPK signaling pathways. Therefore, fargesin and its derivatives may potentially be used for preventing hyperpigmentation disorders in the future.

KEYWORDS

Fargesin; MITF; Melanin; PKA/CREB; p38 MAPK.

Title

Fargesin Inhibits Melanin Synthesis in Murine Malignant and Immortalized Melanocytes by Regulating PKA/CREB and P38/MAPK Signaling Pathways

Author

Ting Fu 1 , Bowen Chai 1 , Yuling Shi 2 , Yongyan Dang 3 , Xiyun Ye 4

Publish date

2019 Apr

PMID

29880739

Abstract

Fargesin is a bioactive lignan from Flos Magnoliae, an herb widely used in the treatment of allergic rhinitis, sinusitis, and headache in Asia. We sought to investigate whether fargesin ameliorates experimental inflammatory bowel disease (IBD) in mice. Oral administration of fargesin significantly attenuated the symptoms of dextran sulfate sodium (DSS)-induced colitis in mice by decreasing the inflammatory infiltration and myeloperoxidase (MPO) activity, reducing tumor necrosis factor (TNF)-α secretion, and inhibiting nitric oxide (NO) production in colitis mice. The degradation of inhibitory κBα (IκBα), phosphorylation of p65, and mRNA expression of nuclear factor κB (NF-κB) target genes were inhibited by fargesin treatment in the colon of the colitis mice. In vitro, fargesin blocked the nuclear translocation of p-p65, downregulated the protein levels of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), and dose-dependently inhibited the activity of NF-κB-luciferase in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Taken together, for the first time, the current study demonstrated the anti-inflammatory effects of fargesin on chemically induced IBD might be associated with NF-κB signaling suppression. The findings may contribute to the development of therapies for human IBD by using fargesin or its derivatives.

KEYWORDS

Fargesin; MITF; Melanin; PKA/CREB; p38 MAPK.

Title

Anti-Inflammatory Effects of Fargesin on Chemically Induced Inflammatory Bowel Disease in Mice

Author

Bei Yue 1 , Yi-Jing Ren 2 , Jing-Jing Zhang 3 , Xiao-Ping Luo 4 , Zhi-Lun Yu 5 , Gai-Yan Ren 6 , A-Ning Sun 7 , Chao Deng 8 , Zheng-Tao Wang 9 , Wei Dou 10

Publish date

2018 Jun 7

PMID

28160867

Abstract

Background: Fargesin is a lignan from Magnolia fargesii, an oriental medicine used in the treatment of nasal congestion and sinusitis. The anti-inflammatory properties of this compound have not been fully elucidated yet.
Purpose: This study focused on assessing the anti-inflammatory effects of fargesin on phorbal ester (PMA)-stimulated THP-1 human monocytes, and the molecular mechanisms underlying them.
Methods: Cell viability was evaluated by MTS assay. Protein expression levels of inflammatory mediators were analyzed by Western blotting, ELISA, Immunofluorescence assay. mRNA levels were measured by Real-time PCR. Promoter activities were elucidated by Luciferase assay.
Results: It was found that pre-treatment with fargesin attenuated significantly the expression of two major inflammatory mediators, cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS). Fargesin also inhibited the production of pro-inflammation cytokines (IL-1β, TNF-α) and chemokine (CCL-5). Besides, nuclear translocation of transcription factors nuclear factor-kappa B (NF-ĸB) and activator protein-1 (AP-1), which regulate multiple pro-inflammatory genes, was suppressed by fargesin in a PKC-dependent manner. Furthermore, among the mitogen-activated protein kinases (MAPKs), only c-Jun N-terminal kinase (JNK) was downregulated by fargesin in a PKC-dependent manner, and this reduction was involved in PMA-induced AP-1 and NF-ĸB nuclear translocation attenuation, demonstrated using a specific JNK inhibitor.
Conclusion: Taken together, our results found that fargesin exhibits anti-inflammation effects on THP-1 cells via suppression of PKC pathway including downstream JNK, nuclear factors AP-1 and NF-ĸB. These results suggest that fargesin has anti-inflammatory properties with potential applications in drug development against inflammatory disorders.

KEYWORDS

Anti-inflammation; Fargesin; JNK inhibitor; NF-kappaB; THP-1 cells.

Title

Fargesin Exerts Anti-Inflammatory Effects in THP-1 Monocytes by Suppressing PKC-dependent AP-1 and NF-ĸB Signaling

Author

Thu-Huyen Pham 1 , Man-Sub Kim 1 , Minh-Quan Le 1 , Yong-Seok Song 1 , Yesol Bak 1 , Hyung-Won Ryu 2 , Sei-Ryang Oh 2 , Do-Young Yoon 3

Publish date

2017 Jan 15


Description :

Fargesin is a bioactive neolignan isolated from magnolia plants,with antihypertensive and anti-inflammatory effects[1][2][3].