β‐CARBOLINE ALKALOIDS: MECHANISMS OF PHOTOTOXICITY TO BACTERIA AND INSECTS

Richard A. Larson, Karen A. Marley, Robert W. Tuveson, May R. Berenbaum

Research output: Contribution to journalArticle

Abstract

Abstract— Phototoxicity of five naturally occurring (3‐carboline alkaloids was assayed against a series of Escherichia coli strains and against the insect Trichoplusia ni (Lepidoptera: Noctuidae). Rank order efficacy of the compounds was comparable in both organisms. Although the bacterial assay demonstrated oxygen dependence, the degree of phototoxicity did not correlate with the relative efficiency of in vitro singlet oxygen or hydrogen peroxide photoproduction by the alkaloids. A better correlation was observed between chromatographic migration distances (lipophilicity) and phototoxicity. Therefore, hydrophobic mechanisms in which the alkaloids diffuse with varying efficiencies into cells or into the vicinity of target molecules may be important modes of phototoxicity for these compounds.

Original languageEnglish (US)
Pages (from-to)665-674
Number of pages10
JournalPhotochemistry and Photobiology
Volume48
Issue number5
DOIs
StatePublished - Nov 1988

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Phototoxic Dermatitis
Carbolines
alkaloids
insects
Alkaloids
bacteria
Insects
Bacteria
Singlet Oxygen
peroxides
oxygen
Escherichia
photoproduction
hydrogen peroxide
organisms
Escherichia coli
Hydrogen Peroxide
Lepidoptera
Assays
Oxygen

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry

Cite this

β‐CARBOLINE ALKALOIDS : MECHANISMS OF PHOTOTOXICITY TO BACTERIA AND INSECTS. / Larson, Richard A.; Marley, Karen A.; Tuveson, Robert W.; Berenbaum, May R.

In: Photochemistry and Photobiology, Vol. 48, No. 5, 11.1988, p. 665-674.

Research output: Contribution to journalArticle

Larson, Richard A. ; Marley, Karen A. ; Tuveson, Robert W. ; Berenbaum, May R. / β‐CARBOLINE ALKALOIDS : MECHANISMS OF PHOTOTOXICITY TO BACTERIA AND INSECTS. In: Photochemistry and Photobiology. 1988 ; Vol. 48, No. 5. pp. 665-674.
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