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Bergaptol

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-P0989

  • Specification : 98.5%(HPLC)

  • CAS number : 486-60-2

  • Formula : C11H6O4

  • Molecular Weight : 202.2

  • PUBCHEM ID : 5280371

  • Volume : 25mg

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Catalogue Number

BD-P0989

Analysis Method

Specification

98.5%(HPLC)

Storage

-20℃

Molecular Weight

202.2

Appearance

Yellow powder

Botanical Source

This product is isolated and purified from the root of Notopterygium incisum

Structure Type

Category

SMILES

C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O

Synonyms

4-hydroxyfuranocoumarin/5-Hydroxypsoralen/4-hydroxyfuro[3,2-g]chromen-7-one/4-Hydroxy7H-furo[3,2-g][1]benzopyran-7-one,4-Hydroxybergapten,5-Hydroxy-6,7-furanocoumarin/xanthotoxol/5-Hydroxyfuranocoumarin/7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-/Psoralin,5-hydroxy/4-Hydroxy-7H-furo[3,2-g]chromen-7-one/Bergaptol/9-hydroxyfuranocoumarin

IUPAC Name

Applications

Density

1.5±0.1 g/cm3

Solubility

Methanol; DMF

Flash Point

142.4±19.3 °C

Boiling Point

311.9±11.0 °C at 760 mmHg

Melting Point

287-290ºC

InChl

InChl Key

GIJHDGJRTUSBJR-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:486-60-2) 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

30934718

Abstract

Methoxylated coumarins represent a large proportion of officinal value coumarins while only one enzyme specific to bergaptol O-methylation (BMT) has been identified to date. The multiple types of methoxylated coumarins indicate that at least one unknown enzyme participates in the O-methylation of other hydroxylated coumarins and remains to be identified. Combined transcriptome and metabonomics analysis revealed that an enzyme similar to caffeic acid O-methyltransferase (COMT-S, S is short for similar) was involved in catalyzing all the hydroxylated coumarins in Peucedanum praeruptorum. However, the precise molecular mechanism of its substrate heterozygosis remains unsolved. Pursuing this question, we determined the crystal structure of COMT-S to clarify its substrate preference. The result revealed that Asn132, Asp271, and Asn325 govern the substrate heterozygosis of COMT-S. A single mutation, such as N132A, determines the catalytic selectivity of hydroxyl groups in esculetin and also causes production differences in bergapten. Evolution-based analysis indicated that BMT was only recently derived as a paralogue of caffeic acid O-methyltransferase (COMT) via gene duplication, occurring before the Apiaceae family divergence between 37 and 100 mya. The present study identified the previously unknown O-methylation steps in coumarin biosynthesis. The crystallographic and mutational studies provided a deeper understanding of the substrate preference, which can be used for producing specific O-methylation coumarins. Moreover, the evolutionary relationship between BMT and COMT-S was clarified to facilitate understanding of evolutionary events in the Apiaceae family.

KEYWORDS

O-methylation; bergaptol O-methyltransferase; caffeic acid O-methyltransferase; coumarins; evolution

Title

The Molecular and Structural Basis of O-methylation Reaction in Coumarin Biosynthesis in Peucedanum praeruptorum Dunn.

Author

Zhao Y1, Wang N2, Sui Z3, Huang C4, Zeng Z5, Kong L6.

Publish date

2019 Mar 27

PMID

27356372

Abstract

OBJECTIVE:
To study the effects of browning inhibitors on Changium smyrnioides suspension cells growth and secondary metabolites production.

METHODS:
Different concentrations of V(C), AC, AHC, Na2S2O3 and PVP were added to the light brown suspension cells, and the contents of phenols, total coumarins, bergaptol and bergapten were determined by UV-Vis and HPLC.

RESULTS:
PVP with low concentration and V(C) improved the growth of the suspension cells in different degrees. It was showed that the content of phenols in the suspension cells was related to the kinds of browning inhibitors. The addition of V(C) in the medium increased the content of total coumarins significantly. After using 2 mg/mL of V(C), the gross increase rate of total coumarins was 51.53%, which was 4.8 times than that of the control group. The browning phenomenon caused by salicylic acid were inhibited by adding 2 mg/mL of V(C) into suspension culture system (with salicylic acid as the inducer). At the same time, the content of bergaptol and bergapten was increased 25.96% and 33.33%, respectively.

CONCLUSION:
V(C) is the best anti-browning agent in this study. It can inhibit browning, and promote cell growth and accumulation of secondary metabolites in Changium smyrnioides suspension cells.

Title

[Effects of Browning Inhibitors on Suspension Cells Growth and Secondary Metabolites Production in Changium smyrnioides].

Author

Zhou P, Xie CQ, Chen JW, Li X.

Publish date

2015 Nov

PMID

26463105

Abstract

Recently, the resources of medicinal plants have been exhausting. The root of Angelica acutiloba is one of the most important ingredients in Japanese Kampo medicine for the treatment of gynecological diseases. In our search for alternative medicinal plant resources of the root of A. acutiloba, we found that its aerial part has the anti-inflammatory potency as well as the root. Phytochemical investigation of the aerial part resulted in the isolation of four compounds including a new dimeric phthalide, namely tokiaerialide (2), along with Z-ligustilide (1), falcarindiol (3), and bergaptol (4). Next, we investigated the in vitro anti-inflammatory activity of 1-4 in lipopolysaccharide-stimulated RAW264 macrophages. Among the isolated compounds, 1 exhibited the most potent inhibition against lipopolysaccharide-induced production of prostaglandin E2 , nitric oxide, and pro-inflammatory cytokines (interleukin-6 and tumor necrosis factor-α). Compounds 3 and 4 also inhibited all inflammatory mediators, but their inhibitory abilities were weaker than those of 1. Furthermore, 1, 3, and 4 strongly also induced heme oxygenase-1. These results suggest that 1, 3, and 4 potentially exert anti-inflammatory activity, and the aerial part of A. acutiloba may be considered to be a useful medicinal resource for inflammatory diseases.

Copyright © 2015 John Wiley & Sons, Ltd.

KEYWORDS

Angelica acutiloba; Z-ligustilide; aerial part; anti-inflammation; macrophages; tokiaerialide

Title

Anti-inflammatory Activity of Constituents Isolated from Aerial Part of Angelica acutiloba Kitagawa.

Author

Uto T1, Tung NH1,2, Taniyama R1, Miyanowaki T1, Morinaga O1, Shoyama Y1.

Publish date

2015 Dec