Vol. 9, No 1, 2011 pp. 9 - 20
DOI 10.2298/FUPCT1101009I
UDC 547-305.2 : 635.262
ALLICIN AND RELATED COMPOUNDS: BIOSYNTHESIS, SYNTHESIS AND PHARMACOLOGICAL ACTIVITY
Dušica P. Ilić , Vesna D. Nikolić, Ljubiša B. Nikolić,
Mihajlo Z. Stanković, Ljiljana P. Stanojević, Milorad D. Cakić
Faculty of Technology, Bulevar oslobođenja 124, 16000 Leskovac, Univesity of Nis, Serbia
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 β-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.
Key words: allicin, ajoene, vinyldithiins, biosynthesis, synthesis, pharmacological activity
ALICIN I SRODNA JEDINJENJA:
BIOSINTEZA, SINTEZA I FARMAKOLOŠKA AKTIVNOST
Ovaj pregled obuhvata detaljnan opis biosinteze alicina (aliltiosulfinata) enzimskom transformacijom alliina, kao i mehanizme i kinetiku različitih reakcija na kojima se zasniva njegova sinteza. Prikazana je i pogodna metoda za određivanje stabilnosti alicina. Pored toga, razmotren je postupak povećanja stabilnosti ovog farmakoški aktivnog agensa, kompleksiranjem sa -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-di¬tiin), koji su od njega stabilniji i takođe farmakološki aktivni. Detaljno su opisani i mehanizmi reakcija kojima se ova jedinjenja dobijaju iz alicina. Pored toga, sumirani su i podaci vezani za farmakološko delovanje alicina i pomenutih transformacionih proizvoda.
Ključne reči: alicin, ajoeni, vinilditini, biosinteza, sinteza, farmakološka aktivnost
