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β‐CARBOLINE ALKALOIDS: MECHANISMS OF PHOTOTOXICITY TO BACTERIA AND INSECTS
Author(s) -
Larson Richard A.,
Marley Karen A.,
Tuveson Robert W.,
Berenbaum May R.
Publication year - 1988
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1988.tb02879.x
Subject(s) - phototoxicity , chemistry , singlet oxygen , trichoplusia , noctuidae , hydrogen peroxide , escherichia coli , bacteria , lepidoptera genitalia , lipophilicity , stereochemistry , in vitro , photochemistry , biochemistry , oxygen , organic chemistry , biology , botany , genetics , gene
— 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.