Allicin and related compounds: Biosynthesis, synthesis and pharmacological activity

Abstract

In this review, the biosynthesis of allicin (allyl thiosulfinate) by enzymatic transformation of alliin and various methods of its synthesis with detailed investigation of mechanisms and kinetics are summarized. A convenient method is also described for determination of allicin stability and the utility of the inclusion complexes of this pharmacologically active agent with ?-cyclodextrins in increasing its stability. Allicin is the initial precursor for the production of ajoene ((E)- and (Z)-4,5,9-trithiadodeca- 1,6,11-triene 9-oxides) and vinyldithiin (2-vinyl-4H-1,3-dithiin, and 3-vinyl-4H-1,2- dithiin), which are more stable and show various pharmacological effects. The mechanisms of allicin transformations to these compounds are given in detail. Finally, the data on the pharmacological effects of allicin and its transformation products, ajoene and vinyldithiin, are presented.Ovaj pregled obuhvata detaljan opis biosinteze alicina (aliltiosulfinata) enzimskom transformacijom alliina, kao i mehanizme i kinetiku razlicitih reakcija na kojima se zasniva njegova sinteza. Prikazana je i pogodna metoda za odredjivanje stabilnosti alicina. Pored toga, razmotren je postupak povecanja stabilnosti ovog farmakoloski aktivnog agensa, kompleksiranjem sa b-ciklodekstinima. Alicin je prekursor za sintezu ajoena ((E)- i (Z)-4,5,9-tritiadodeka-1,6,11-trien- 9-oksidi) i vinilditiina (2-vinil-4H-1,3-ditiin i 3-vinil-4H-1,2-ditiin), koji su od njega stabilniji i takodje farmakoloski aktivni. Detaljno su opisani i mehanizmi reakcija kojima se ova jedinjenja dobijaju iz alicina. Pored toga, sumirani su i podaci vezani za farmakolosko delovanje alicina i pomenutih transformacionih proizvoda. PR Projekat Ministarstva nauke Republike Srbije, br. TR-34012