Application of Hansch's model to capsaicinoids and capsinoids: a study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids.
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.
Barbero
Gerardo F
GF
Department of Analytical Chemistry, University of Cádiz, Avda. República Saharaui, s/n, Puerto Real, Cádiz, Spain.
Molinillo
José M G
JM
Varela
Rosa M
RM
Palma
Miguel
M
Macías
Francisco A
FA
Barroso
Carmelo G
CG
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D014908:Triticum / Q000187:drug effects / Q000254:growth & development
D000470:Alkaloids