Tagetes Terthienyls

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. 

Tagetes is a very rich source of naturally occurring thiophene derivatives. Various bithiophenes, for example, 12-14 or terthienyl 15, have been identified from Tagetes patula L. Asteraeeae) by GLC-MS analysis <2002ZNC63>. 

In studies investigating the resistance of Tagetes to Meloidogyne species, the extract from the roots of Tagetes species was found to be more active than those obtained from other parts of the plants. From this fraction, an active compound was isolated and shown to be identical to a-terthienyl (3). Subsequent work led to the identification of a second compound (4). Both were toxic to H. rostochiensis (0.1 ppm 100 ppm), D. dipsaci (5... 

Jente et al investigated how a precursor with 13 carbon atoms was converted into a product with 12 carbon atoms 144). They assessed the conversion of two series of bithiophenes, one with 12 and the other with 13 carbon atoms, into products in which the side chain had been modified, and into a-terthienyl. The compounds tested are shown in Scheme 3. Each of these compounds was tested in Tagetes patula for incorporation into the four products shown below (Scheme 4). The percent incorporations into each product tested are summarized in Table 11 ... 

Bakker, j., F.J. Gommers, I. Nieuwenhuis, and H. Wynberg Photoactivation of the Nematicidal Compound a-Terthienyl from Roots of Marigolds (Tagetes Species). A Possible Singlet Oxygen Role. J. Biol. Chem. 254, 1841 (1979). 

Gommers, F.J., and J. Barker Mode of Action of a-Terthienyl and Related Compounds May Explain the Suppressant Effects of Tagetes species on Populations of Free Living Endoparasitic Plant Nematodes. Bioact. Mol. (Chem. Biol. Nat.-Occurring Acetylenes Relat. Compd.) 7, 61 (1988). 

Gommers, F.J., J. Barker, and L. Smits Effects of Singlet Oxygen Generated by the Nematicidal Compound a-Terthienyl from Tagetes on the Nematode Aphelenchus avenae. Nematologica 26, 369 (1980). 

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). 

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