Enzymatic transformation products of phloretin as potent anti-adipogenic compounds

2021 ◽  
Author(s):  
Gyeong Han Jeong ◽  
Jae-Hyeon Cho ◽  
Eui Kyun Park ◽  
Tae Hoon Kim
Keyword(s):  
Polyphenol Oxidase ◽  
Agaricus Bisporus ◽  
Spectroscopic Data ◽  
New Products ◽  
Mrna Level ◽  
Transformation Products ◽  
Structure Modification ◽  
Enzymatic Transformation ◽  
Oxidized Products ◽  
Absolute Stereochemistry

Abstract Enzymatic structure modification of the representative chalcone phloretin (1) with polyphenol oxidase from Agaricus bisporus origin produced two new biphenyl-type phloreoxin (2) and phloreoxinone (3), and a previously undescribed (2R)-5,7,3“,5”-tetrahydroxyflavanone (4). The structure of these new oxidized products 2‒4 elucidated by interpreting the spectroscopic data (NMR and FABMS) containing the absolute stereochemistry established by analysis of the circular dichroism (CD) spectrum. Compared to the original phloretin, the new products (2) and (3) showed highly improved anti-adipogenic potencies both toward pancreatic lipase and accumulation of 3T3-L1 cells. Aslo, phloreoxin (2) effectively inhibited the expression of C/EBPβ, PPARγ, and aP2 at the mRNA level in the 3T3 adipocytes. Thus, phloreoxin (2), containing a biphenyl moiety catalyzed by A. bisporus polyphenol oxidase, have the potential to influence the anti-adipogenic capacity.

Studies of Australian Ascidians. VI. Virenamides D and E, Linear Peptides from the Colonial Didemnid Ascidian Diplosoma virens

1997 ◽  
Vol 50 (4) ◽  
pp. 337 ◽  
Author(s):  
Yunjiang Feng ◽  
Bruce F. Bowden
Keyword(s):  
Great Barrier Reef ◽  
Spectroscopic Data ◽  
Two Dimensional ◽  
Barrier Reef ◽  
Minor Constituents ◽  
One Dimensional ◽  
The Absolute ◽  
Absolute Stereochemistry

Two new linear cytotoxic tripeptides, virenamides D and E, have been isolated as minor constituents of extracts of the didemnid ascidianDiplosoma virens collected on the Great Barrier Reef, Australia. Their structures were deduced from one-dimensional and two-dimensional n.m.r. spectroscopic data, and the absolute stereochemistry of virenamide E is proven by synthesis from virenamide A.

scholarly journals Synthesis and Antimicrobial Activity of 1-[2-(10-p-Chlorobenzyl) phenothiazinyl]-3-(substituted aryl)-2-propen-1-ones

2009 ◽  
Vol 6 (s1) ◽  
pp. S254-S258 ◽  
Author(s):  
R. K. Upadhyay ◽  
Megha S. Upadhyay ◽  
S. Jain
Keyword(s):  
Antimicrobial Activity ◽  
Spectroscopic Data ◽  
Room Temperature ◽  
Antimicrobial Agents ◽  
Sodium Hydroxide Solution ◽  
New Products ◽  
Subsequent Reaction ◽  
Filter Paper Disc ◽  
H Nmr ◽  
Paper Disc

Aiming at the development of antimicrobial agents, we have synthesized nine chlorobenzyl substituted phenothiazinyl chalcones by condensing 2-acetyl phenothiazine with aldehyde derivatives in dilute ethanolic sodium hydroxide solution at room temperature according to Claisen - Schmidt condensation and subsequent reaction of products withp-chlorobenzyl bromide. Structures of these compounds were elucidated by their IR, 'H NMR spectroscopic data and microonalyses. The antimicrobial activity of the new products was evaluated by Filter Paper Disc Method.

Sign in / Sign up

Export Citation Format

Share Document