Abstract
Alpha-terthienyl is toxic to late embryonic stages ofRana pipiens in the presence of sunlight. Neither α-terthienyl alone in the dark nor a previously photolyzed solution of α-terthienyl has comparable activity. The LC50 was 0.11 ppm with 30 min of exposure and 0.018 ppm with 2 hr of exposure to sunlight. Anthracene, a representative example of polycyclic aromatic hydrocarbons widely distributed in the environment, also showed similar phototoxicity, with an LC50 of 0.065 ppm after 30 min of exposure and 0.025 ppm after 5 hr.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Arnason, T., Stein, J.R., Graham, E., Wat, C.-K., Towers, G.H.N., andLam, J. 1980. Phototoxicity to selected marine and freshwater algae of polyacetylenes from species in the Asteraceae.Can. J. Bot. 59:54–58.
Arnason, T., Chan, G.F.Q., Wat, C.-K., Downum, K., andTowers, G.H.N. 1981a. Oxygen requirement for near-UV mediated cytotoxicity of alpha-terthienyl toEscherichia coli andSaccharomyces cerevisiae.Photochem. Photobiol. 33:821–824.
Arnason, T., Swain, T., Wat, C.-K., Graham, E.A., Partington, S., Towers, G.H.N., andLam, J. 1981b. Mosquito larvicidal activity of polyacetylenes from species in the Asteraceae.Biochem. Syst. Ecol. 9:63–68.
Bakker, J., Gommers, F.J., Nieuwenhuis, I., andWynberg, H. 1979. Photoactivation of the nematicidal compound alpha-terthienyl from roots of Mangolds (Tagetes species). A possible singlet oxygen role.J. Biol. Chem. 254:1841–1844.
Beny, J.-P., Dhawan, S.N., Kagan, J., andSundlass, S. 1982. Synthesis of 3,2′∶5′,3″-terthiophene and other terthiophenes by the thiophenecarboxaldehyde to ethynylthiophene to dithienylbutadiyne route.J. Org. Chem. 47:2201–2204.
Bowling, J.W., Leversee, G.J., Landrum, P.F., andGiesy, J.P., 1983. Acute mortality of anthracene-contaminated fish exposed to sunlight.Aquat. Toxicol. 3:79–90.
Campbell, G., Lambert, J.D.H., Arnason, T., andTowers, G.H.N. 1982. Allelopathic properties of alpha-terthienyl and phenylheptatriyne, naturally occurring compounds from species of Asteraceae.J. Chem. Ecol. 8:961–972.
Chan, G.F.Q., Towers, G.H.N., andMitchell, J.C. 1975. Ultraviolet mediated antibiotic activity of thiophene compounds ofTagetes.Phytochemistry 14:2295–2296.
Downum, K.R., Hancock, R.E.W., andTowers, G.H.N. 1982. Mode of action of alphaterthienyl onEscherichia coli: Evidence for a photodynamic effect on membranes.Photochem. Photobiol. 36:517–523.
Gommers, F.J. 1972. Increase in the nematicidal activity of alpha-terthienyl and related compounds by light.Nematologica 18:458–462.
Gommers, F.J., Bakker, J., andSmits, L. 1980. Effect of singlet oxygen generated by the nematicidal compound alpha-terthienyl fromTagetes on the nematodeAphelenchus avenae.Nematologica 26:369–375.
Harvey, Jr. (to E.I. du Pont de Nemours and Co.). 1963. Method for the control of plant growth. U.S. Patent 3,086,854.
Kagan, J., andChan, G. 1983. The photoovicidal activity of plant components towardsDrosophila melanogaster.Experientia 39:402–403.
Kagan, J., andGabriel, R. 1980.Candida utilis as a convenient and safe substitute for the pathogenic yeastC. albicans in Daniels' phototoxicity test.Experientia 36:587.
Kagan, J., Gabriel, R., andReed, S. 1980. Alpha-terthienyl, a non-photodynamic phototoxic compound.Photochem. Photobiol. 31:465–469.
Kagan, J., Chan, G., Dhawan, S.N., Arora, S.K., andPrakash, I. 1983. The effect of ultraviolet light on the toxicity of natural products toward the eggs ofDrosophila melanogaster.J. Nat. Prod. 46:646–650.
Towers, G.H.N. 1980. Photosensitizers from plants and their photodynamic action, pp. 183–202,in L. Reinhold, J.B. Harborne, and T. Swain (eds.). Progress in Phytochemistry, Vol. 6. Pergamon Press, Oxford.
Towers, G.H.N., Wat, C.-K., Graham, E.A., Bandoni, R.J., Chan, G.F.Q., Mitchell, J.C., andLam, J. 1977. Ultraviolet-mediated antibiotic activity of species of Compositae caused by polyacetylenic compounds.Lloydia 40:487–498.
Wat, C.-K., Prasad, S.K., Graham, E.A., Partington, S., Arnason, T., Towers, G.H.N., andLam, J. 1981. Photosensitization of invertebrates by natural polyacetylenes.Biochem. Syst. Ecol. 9:59–62.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kagan, J., Kagan, P.A. & Buhse, H.E. Light-dependent toxicity of α-terthienyl and anthracene toward late embryonic stages ofRana pipiens . J Chem Ecol 10, 1115–1122 (1984). https://doi.org/10.1007/BF00987517
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00987517