Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay

Kamal A. Rashid, Christopher Albert Mullin, Ralph O. Mumma

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4′) substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch π parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.

Original languageEnglish (US)
Pages (from-to)71-79
Number of pages9
JournalMutation Research/Genetic Toxicology
Volume169
Issue number3
DOIs
StatePublished - Jan 1 1986

Fingerprint

Chalcones
Salmonella
styrene oxide
Assays
Electrons
Chalcone
Epoxidation
Hydrophilicity
Salmonella typhimurium
Hydrophobic and Hydrophilic Interactions
Liver
Oxides
Rats
Chemical activation
Derivatives
Enzymes
chalcone epoxide
1,3-diphenylpropene

All Science Journal Classification (ASJC) codes

  • Toxicology
  • Genetics

Cite this

Rashid, Kamal A. ; Mullin, Christopher Albert ; Mumma, Ralph O. / Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay. In: Mutation Research/Genetic Toxicology. 1986 ; Vol. 169, No. 3. pp. 71-79.
@article{8a8fa1b5d5db4fbaad34b8511348ad70,
title = "Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay",
abstract = "31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4′) substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch π parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.",
author = "Rashid, {Kamal A.} and Mullin, {Christopher Albert} and Mumma, {Ralph O.}",
year = "1986",
month = "1",
day = "1",
doi = "10.1016/0165-1218(86)90086-8",
language = "English (US)",
volume = "169",
pages = "71--79",
journal = "Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure",
issn = "0165-1218",
publisher = "Elsevier BV",
number = "3",

}

Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay. / Rashid, Kamal A.; Mullin, Christopher Albert; Mumma, Ralph O.

In: Mutation Research/Genetic Toxicology, Vol. 169, No. 3, 01.01.1986, p. 71-79.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay

AU - Rashid, Kamal A.

AU - Mullin, Christopher Albert

AU - Mumma, Ralph O.

PY - 1986/1/1

Y1 - 1986/1/1

N2 - 31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4′) substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch π parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.

AB - 31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4′) substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch π parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.

UR - http://www.scopus.com/inward/record.url?scp=0022645523&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0022645523&partnerID=8YFLogxK

U2 - 10.1016/0165-1218(86)90086-8

DO - 10.1016/0165-1218(86)90086-8

M3 - Article

VL - 169

SP - 71

EP - 79

JO - Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure

JF - Mutation Research - Genetic Toxicology Testing and Biomonitoring of Environmental or Occupational Exposure

SN - 0165-1218

IS - 3

ER -