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Kuwanon H

$572

  • Brand : BIOFRON

  • Catalogue Number : BD-P0158

  • Specification : 98.0%(HPLC)

  • CAS number : 76472-87-2

  • Formula : C45H44O11

  • Molecular Weight : 760.8

  • PUBCHEM ID : 5281668

  • Volume : 25mg

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Catalogue Number

BD-P0158

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

760.8

Appearance

Yellow powder

Botanical Source

This product is isolated and purified from the root bark of Morus alba L.

Structure Type

Category

SMILES

CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C=C(C5=C4OC(=C(C5=O)CC=C(C)C)C6=C(C=C(C=C6)O)O)O)O

Synonyms

8-[(1S,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3-methylbut-2-enyl)chromen-4-one

IUPAC Name

Applications

Naturally occurring Diels-Alder-type adducts from Morus nigra as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B. PUMID/DOI:29275228 Eur J Med Chem. 2018 Jan 20;144:277-288. Mycobacterium tuberculosis (Mtb) protein tyrosine phosphatases A and B (PtpA and PtpB) have been recognized as potential molecular targets for the development of new therapeutic strategies against tuberculosis (TB). In this context, we have recently reported that the naturally occurring Diels-Alder-type adduct Kuwanol E is an inhibitor of PtpB (Ki = 1.6 ± 0.1 μM). Here, we describe additional Diels-Alder-type adducts isolated from Morus nigra roots bark that inhibit PtpB at sub-micromolar concentrations. The two most potent compounds, namely Kuwanon G and Kuwanon H, showed Ki values of 0.39 ± 0.27 and 0.20 ± 0.01 μM, respectively, and interacted with the active site of the enzyme as suggested by kinetics and mass spectrometry studies. Molecular docking coupled with intrinsic fluorescence analysis and isothermal titration calorimetry (ITC) further characterized the interaction of these promising PtpB inhibitors. Notably, in an Mtb survival assay inside macrophages, Kuwanon G showed inhibition of Mtb growth by 61.3%. All these results point to the common Diels-Alder-type adduct scaffold, and highlight its relevance for the development of PtpB inhibitors as candidate therapeutics for TB.

Density

1.371g/cm3

Solubility

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

Flash Point

292.5ºC

Boiling Point

969.8ºC at 760 mmHg

Melting Point

InChl

InChl Key

DKBPTKFKCCNXNH-QXGWMLRCSA-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#:76472-87-2) 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

31385700

Abstract

The emergence and rapid spread of methicillin-resistant Staphylococcus aureus (MRSA) critically requires alternative therapeutic options. New antibacterial drugs and strategies are urgently needed to combat MRSA-associated infections. Here, we investigated the antibacterial activity of flavones from Morus alba and the potential mode of action against MRSA. Kuwanon G, kuwanon H, mulberrin, and morusin displayed high efficiency in killing diverse MRSA isolates. On the basis of structure-activity analysis, the cyclohexene-phenyl ketones and isopentenyl groups were critical to increase the membrane permeability and to dissipate the proton motive force. Meanwhile, mechanistic studies further showed that kuwanon G displayed rapid bactericidal activity in vitrowith difficulty in developing drug resistance. Kuwanon G targeted phosphatidylglycerol and cardiolipin in the cytoplasmic membrane through the formation of hydrogen bonds and electrostatic interactions. Additionally, kuwanon G promoted wound healing in a mouse model of MRSA skin infection. In summary, these results indicate that flavones are promising lead compounds to treat MRSA-associated infections through disrupting the proton motive force and membrane permeability.

KEYWORDS

MRSA; flavone; kuwanon G; membrane permeability; proton motive force.

Title

Natural Flavones from Morus alba against Methicillin-Resistant Staphylococcus aureus via Targeting the Proton Motive Force and Membrane Permeability

Author

Shuai-Cheng Wu 1 2 3, Fei Han 1, Mei-Rong Song 1, Shang Chen 1, Qian Li 1, Qi Zhang 1, Kui Zhu 1, Jian-Zhong Shen 1

Publish date

2019 Sep 11;

PMID

16408801

Title

[Structure and spectral characteristics of Diels-Alder type adducts from Morus]

Author

Sheng-Jun Dai 1, Zi-Ming Lu, Ruo-Yun Chen, De-Quan Yu

Publish date

2005 Oct;

PMID

11494599

Abstract

Many isoprenylated flavonoids have been isolated from mulberry trees and related plants (Moraceae). Among them, kuwanons G (13) and H (14) were the first isolated active substances exhibiting a hypotensive effect from the Japanese Morus root bark. These compounds are considered to be formed through an enzymatic Diels-Alder reaction of a chalcone (15) and dehydro-kuwanon C (16) or its equivalent. Since that time, about forty kinds of Diels-Alder type adducts structurally similar to that of 13 have been isolated from the moraceous plants. Some strains of Morus alba as well as M. bombycis callus tissues have a high productivity of mulberry Diels-Alder type adducts, such as chalcomoracin (26) and kuwanon J (28). The biosynthesis of the mulberry Diels-Alder type adducts has been studied with the aid of the cell strain. Chalcomoracin (26) and kuwanon J (28) were proved to be enzymatic Diels-Alder type reaction products by the administration experiment with O-methylchalcone derivatives. Furthermore, for the isoprenoid biosynthesis of prenylflavonoids in Morus alba callus tissues, a novel way through the junction of glycolysis and pentose-phosphate cycle was proposed. The crude enzyme fraction catalyzing the Morus Diels-Alder type reaction could be isolated. Studies of phenolic constituents of licorice (Glycyrrhiza species) were carried out. On the course of the structure determination of the phenolic constituents of licorice, two new NMR structure determination methods for prenylflavonoids were found. Furthermore, the prenylphenols isolated from licorice were summarized according to the origin of the materials.

Title

[Chemistry and biosynthesis of prenylflavonoids]

Author

T Nomura 1

Publish date

2001 Jul;