Alpha-terthienyl

Tagetes erecta L. Chou Fu Yong (Marigold) (leaf, flower) Alpha-terthienyl, d-limonene, 1-linalool, tagetone, n-nonyl aldehyde.50 Treat sores and ulcers, cold, conjuctivitis, cough, mastitis, mumps. 

Guillet, G Harmatha, J., Wadell, T.G., Philogene, B.J. R. and Arnason, J.T. (2000). Synergism between sesquiterpene lactones and alpha-terthienyl. Photochemistry and Photobiology 71 111-115. 

J. Kagan, E.D. Kagan, E. Seigneurie (1986). Alpha-terthienyl, a powerful fish poison with light-dependent activity. Chemosphere, 15,49-57. 

Figure 1. Structures of representative phototoxic plant products from various phytochemical classes. (I) 1-phenylhepta-1,2,3-triyne (acetylenic polyine) (II) 6-methoxyeuparin (benzofuran) (III) harmane (beta-carboline alkaloid) (IV) khellin (furo-chromone) (V) 8-methoxypsoralen (furocoumarin) (VI) dictamnine (furoqulnoline alkaloid) (VII) nordihydroguaiaretic acid (lignan) and (VIII) alpha-terthienyl (thiophene).

The broad-spectrum biocidal action induced by phototoxic allelochemicals has been demonstrated toward a range of organisms including bacteria, fungi, nematodes, insects as well as non-photo-toxin-containing plants. Table III summarizes the organisms susceptible to photosensltlzatlon by alpha-terthienyl, a phototoxin characteristic of many Asteraceae species (4, 10-11). The toxicity of this thiophenic polyine toward plant pathogens (e.g.,... 

Table III. UVA-Medlated Lethal Activity of Alpha-Terthienyl Toward Various Organisms...

Rampone WM, McCullough JL, Weinstein GD, Towers GH, Berns MW, Abeysekera B (1986) Characterization of cutaneous phototoxicity induced by topical alpha terthienyl and ultraviolet A radiation. J Invest Dermatol 87 354-357 El Sayed F, Manzur F, Bayle P, Marguery MS, Bazex J (1995) Contact urticaria from abietic acid. Contact Dermatitis 32 361-362... 

Using alpha-terthienyl as the model for this third class of photoactivated miticides, an azole heterocycle was incorporated as the central anchor ring of molecule 3. Both oxazole and thiazole heterocycles were examined. Aryl and heteroaryl moieties were substituted about the azole. 

Cooper, G.K., and C.I. Nitsche Alpha-Terthienyl, Phototoxic Allelochemical. Review of Research on its Mechanism of Action. Bioorg. Chem. 13, 362 (1985). 

Hasspieler, B.M., J.T. Arnason, and A.E.R. Downe. Toxicity, Localization and Elimination of the Phototoxin, Alpha-Terthienyl, in Mosquito Larvae. J. Am. Mosq. Control Assoc. 4, 479 (1988). 

Iyengar, S., J.T. Arnason, B.J.R. Philogene, P. Morand, N.H. Werstiuk, and G. Timmins Toxicokinetics of the Phototoxic Allelochemical Alpha-Terthienyl in Three Herbivorous Lepidoptera. Pestic. Biochem. Physiol. 29, 1 (1987). 

Kagan, J., R. Gabriel, and S.A. Reed Alpha-terthienyl, a Non-Photodynamic Phototoxic Compound. Photochem. Photobiol. 31, 465 (1980). 

Kagan, J., M. Hasson and F. Grynspan The Inactivation of Acetylcholinesterase by Alpha-Terthienyl and Ultraviolet Light. Studies in vitro and in Larvae of the Mosquito Aedes aegypti. Biochem. Biophys. Acta 802, 442 (1984). 

Kagan, J., P.A. Kagan, and H. Buhse, Jr. Light-Dependent Toxicity of Alpha-Terthienyl and Anthracene Toward Late Embryonic Stages of Rana pipiens. J. Chem. Ecol. 10, 1117 (1984). 

Kagan, J., E.D. Kagan, and E. Seigneurie Alpha-Terthienyl, a Powerful Fish Poison with Light-Dependent Activity. Chemosphere 15, 49 (1986). 

Kagan, J., E. Kagan, S. Patel, D. Perrine, V. Bindokas Light-Dependent Effects of Alpha-Terthienyl in Eggs, Larvae, and Pupae of Mosquito Aedes aegypti. J. Chem. Ecol. 13, 593 (1987). 

Rampone, W.M., J.L. McCullough, G.D. Weinstein, G.H.N. Towers, M.W. Berns, and N. Abeysekera Characterization of Cutaneous Phototoxicity Induced by Topical Alpha-terthienyl and Ultraviolet A Radiation. J. Invest. Dermatol. 87, 354 (1986). 

Singh, S.P., P. Sharma and L.K. Vats Light-Dependent Toxicity of the Extract of Plant Tagetes erecta and Alpha-Terthienyl Toward Larvae of Mosquito Culex tritaeniorhynchus. Toxic. Environ. Chem. 16, 81 (1987). 

C. H. Evans and J. C. Scaiano, Photochemical generation of radical cations from alpha-terthienyl and related thiophenes kinetic behavior and magnetic field effects on radical ion pairs in micellar solution, J. Am. Chem. Soc., 1990,112, 2694. 

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