Comparative analysis of the allelopathic effects of the chemical compounds tithonine and acetylated tithonine

A.P.S. Souza Filho F.C. Borges L.S. Santos About the authors

The objective of this paper was to establish the variations in the allelopathic activity of the chemical substance tithonine, in function of the acetylation of its molecule. Germination bioassays, under 25 ºC of constant temperature and 12-hour photoperiod, and radicle and hypocotyl development bioassays under 25ºC of constant temperature and 24-hour photoperiod were developed. The receiving plant used was the weed Mimosa pudica. Spectral analysis RMN ¹H and 13C and bidimensional RMN techniques were carried out on the acetylated molecule. The acetylation process produced the molecule 7,4'- dimethoxy-3'-acetylflavone, which differed from the original molecule, identified as 7,4'-dimethoxy-3'-hydroxyflavone. The structure of the acetylated tithonine was confirmed by the specters of RMN ¹H, 13C, DEPT, COSY and HETCOR. Tithonine was acetylated with acetic anhydride in pyridine. The comparative analysis of the allelopathic activity of the two substances showed that acetylated tithonine presented a greater potential to inhibit seed germination, as well as root and hypocotyl development of M. pudica. Both tithonine and acetylated tithonine showed the same behavior pattern in relation to substance concentration. The data obtained allow suggesting the possibility of increasing the biological activity of a chemical substance with allelopathic activity without compromising its biological peculiarities, desirable to nature and to the interests of society.

allelopathy; acetylation; structure; inhibition; molecule

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