Research article summary (published 30 Dec 1996):

Hydrogen bond formation as basis for radical scavenging activity: a structure-activity study of C-methylated dihydrochalcones from Myrica gale and structurally related acetophenones.

Full Abstract

A naturally occurring flavonoid, myrigalone B (2',6' -dihydroxy-4'-methoxy-3',5'-dimethyl-dihydrochal-cone) is an effective antioxidant and scavenger of the diphenylpicrylhydrazyl radical, while the closely related angoletin (2',4'-dihydroxy-6'-methoxy-3',5'-dimethyl-dihydrochalcone) is inactive. From NMR spectra, it appears that myrigalone B has a time-averaged conformation in which the substituted aromatic ring is orthogonal to the carbonyl group, while angoletin is coplanar. By donating a phenolic hydrogen in radical scavenging, myrigalone B will lose its symmetrical structure and may thereby change to a coplanar conformation forming a strong intramolecular hydrogen bond between the remaining phenolic hydrogen and the carbonyl group. The energy gain entailed would then appear to be a driving force for the radical scavenging by myrigalone B. Angoletin, being coplanar, lacks this driving force. To verify this hypothesis, the conformation and radical scavenging activity of a series of phenolic acetophenones were studied. All substances that had an orthogonal conformation and could form intramolecular hydrogen bonds by loss of a phenolic hydrogen were DPPH scavengers, while compounds lacking these properties were inactive. From this, we propose that formation of intramolecular hydrogen bonds may lead to radical scavenging activity.

Author information

Author/s: Mathiesen, L (L); Malterud, K E (KE); Sund, R B (RB);

Affiliation: Department of Pharmacology, School of Pharmacy, University of Oslo, Norway.

Journal and publication information

Publication Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't

Journal: Free radical biology & medicine (Free Radic Biol Med), published in UNITED STATES. (Language: eng)

Reference: 1997-; vol 22 (issue 1-2) : pp 307-11

Dates: Created 1997/04/10; Completed 1997/04/10; Revised 2006/11/15;

PMID: 8958155, status: MEDLINE (last retrieval date: 2/18/2009, IMS Date: )

Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.

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MeSH headings (categories)

This article was linked to the MESH Headings shown below.

Acetophenones - chemistry; pharmacology Animals Antioxidants - chemistry; pharmacology Bepridil - analogs & derivatives Chalcone - analogs & derivatives; chemistry; pharmacology Chalcones Flavonoids - chemistry; pharmacology Free Radical Scavengers - pharmacology Free Radicals

Hydrogen Bonding Magnetic Resonance Spectroscopy - methods Molecular Conformation Molecular Structure Picrates Plants - chemistry Protons Rats Structure-Activity Relationship

Associated Chemicals: Acetophenones (0) ; Antioxidants (0) ; Chalcones (0) ; Flavonoids (0) ; Free Radical Scavengers (0) ; Free Radicals (0) ; Picrates (0) ; Protons (0) ; myrigalone B (0) ; 2,2-diphenyl-1-picrylhydrazyl (1898-66-4) ; Bepridil (64706-54-3) ; angoletin (76444-55-8) ; Chalcone (94-41-7)

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