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Wighteone

$1,504

  • Brand : BIOFRON

  • Catalogue Number : BN-O1358

  • Specification : 98%(HPLC)

  • CAS number : 51225-30-0

  • Formula : C20H18O5

  • Molecular Weight : 338.35

  • PUBCHEM ID : 5281814

  • Volume : 5mg

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Catalogue Number

BN-O1358

Analysis Method

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

338.35

Appearance

Yellow powder

Botanical Source

This product is isolated and purified from the herbs of Glycyrrhiza glabra

Structure Type

Category

SMILES

CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=CC=C(C=C3)O)O)C

Synonyms

Erythrinin B/5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one/4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-/6-prenylgenistein/5,7,4'-Trihydroxy-6-prenylisoflavone/6-isopentenylgenistein/5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-chromen-4-one/6-dimethylallylgenistein/5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one/4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-/Wighteone/6-prenyl-5,7,4'-trihydroxyisoflavone

IUPAC Name

Density

1.4±0.1 g/cm3

Solubility

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

Flash Point

212.8±23.6 °C

Boiling Point

586.1±50.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

KIMDVVKVNNSHGZ-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#:51225-30-0) 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

29140457

Abstract

Prenylated isoflavonoids have been found in several legume plants, and they possess various biological activities that play important roles in both plant defense and human health. However, it is still unknown whether prenylated isoflavonoids are present in the model legume plant Lotus japonicus. In the present study, we found that the prenylated isoflavonoid wighteone was produced in L. japonicus when leaf was supplemented with genistein. Furthermore, a novel prenyltransferase gene, LjG6DT, was identified, which shared high similarity with and was closely related to several known prenyltransferase genes involved in isoflavonoid biosynthesis. The recombinant LjG6DT protein expressed in yeast exhibited prenylation activity toward genistein as an exclusive substrate, which produced wighteone, a prenylated genistein at the C-6 position that occurs normally in legume plants. The LjG6DT-green fluorescent protein (GFP) fusion protein is targeted to plastids. The transcript level of LjG6DT is induced by glutathione, methyl jasmonate and salicylic acid, implying that LjG6DT is involved in stress response. Overexpression of LjG6DT in L. japonicus hairy roots led to increased accumulation of wighteone when genistein was supplied, indicating that LjG6DT is functional in vivo. Feeding assays with the upstream intermediate naringenin revealed that accumulation of wighteone in L. japonicus was dependent on genistein supplementation, and accumulation of wighteone is competed by genistein methylation. This study demonstrated that phytoalexin wighteone is inducibly produced in L. japonicus, and it provides new insight into the biosynthesis and accumulation of prenylated isoflavonoids in legume plants.

© The Author 2017. Published by Oxford University Press on behalf of Japanese Society of Plant Physiologists. All rights reserved. For permissions, please email: journals.permissions@oup.com.

KEYWORDS

Genistein; Isoflavonoid prenyltransferase; Isoflavonoids; Lotus japonicus; Wighte

Title

Genistein-Specific G6DT Gene for the Inducible Production of Wighteone in Lotus japonicus.

Author

Liu J1,2,3, Jiang W1, Xia Y1, Wang X3, Shen G4, Pang Y1,3.

Publish date

2018 Jan 1

PMID

27313682

Abstract

It is well known that heat shock protein 90 (HSP90) overexpression is correlated with poor prognosis and chemo-resistance in human malignant cancers. At the same time, wighteone, or 6-prenyl-5,7,4′-trihydroxyisoflavone, a major isoflavone component of the ornamental tall tree Erythrina suberosa, has been demonstrated to exhibit a potent anti-proliferative effect on human leukemia HL-60 cancer cell lines. In this study, the effects of wighteone on the proliferation of HER2-positive breast cancer cells were investigated, and the action mechanism was explored. MCF-7 HER2-positive breast cancer cells were treated with various concentrations of wighteone. The growth inhibitory rate of the cells was calculated by MTT assay, apoptosis was detected by flow cytometry, and the expression level of HSP90 was assessed by western blot analysis. The addition of wighteone at concentrations ranging from 1-10 g/ml in the medium for 48 h had a marked inhibition on the proliferation of HER2-positive cancer cell lines. The growth inhibitory rates with 0.5, 2 or 8 mM wighteone were significantly higher compared with the control group. Apoptosis in the wighteone-treated cells was also significantly higher compared with the control group. The expression level of HSP90 in the wighteone group was significantly lower than that in the control group. Our findings demonstrated that wighteone effectively inhibited the proliferation of HER2-positive cancer cell lines, and this is considered to be the result of downregulating HSP90 receptor and downstream signaling.

KEYWORDS

apoptosis; breast cancer; metabolite; protein expression; wighteone

Title

HSP90 expression and its association with wighteone metabolite response in HER2-positive breast cancer cells.

Author

Cao ZW1, Zeng Q2, Pei HJ1, Ren LD1, Bai HZ1, Na RN1.

Publish date

2016 Jun

PMID

16369693

Abstract

The limitations of currently available antifungal agents and the rapid emergence of drug-resistant strains necessitate more efficient approaches to screening and developing novel antifungal drugs. The antifungal activity of the natural products of a series of plants was evaluated and wighteone, 5, 7, 4′-trihydroxy-6-(gamma,gamma-dimethylallyl)isoflavone showed excellent anti-yeast activity (MIC against Saccharomyces cerevisiae was 4 microg/ml). Transcriptome profiling of wighteone-treated S. cerevisiae indicated that wighteone is different from commonly used antifungal compounds in its mode of action.

Title

Genome-wide analysis of the expression profile of Saccharomyces cerevisiae in response to treatment with the plant isoflavone, wighteone, as a potential antifungal agent.

Author

Yin H1, Zhao Y, Zhang Y, Zhang H, Xu L, Zou Z, Yang W, Cheng J, Zhou Y.

Publish date

2006 Jan


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