Disease relevance of Kautschiin

• The key cycloaddition precursor is convergently assembled from (R)-(+)-limonene and cyclopropane diester through a novel decarboxylative dehydration reaction [1].
• Allergic contact dermatitis from dipentene in wax polish [2].
• In previous patch test studies on consecutively tested dermatitis patients, oxidized R-limonene has been proven to be a good and frequent indicator of fragrance-related contact allergy [3].

High impact information on Kautschiin

• The synthesis of R-perillic acid is also described, because previous reports on the activity of perillic acid against isoprenylation enzymes refer to the S-enantiomer, although it is the R-enantiomer which is the metabolite of R-limonene [4].
• Comparison of the cavities in A2U and in the corresponding mouse urinary protein (MUP) reveal that the former is tailor-made for small oval hydrophobic ligands such as DLO [5].
• Lycopene, an active natural lipophilic antioxidant from tomato, has solubilized in water-in-oil, bicontinuous, and oil-in-water types of microemulsions up to 10 times the oil [(R)-(+)-limonene] dissolution capacity [6].
• Patch tests with 6 terpenes on 22 patients revealed that 17 were allergic to alpha-pinene and 15 to dipentene; 12 were allergic to both [7].
• Fennel oil contained almost 2/3 anethol, approximately 1/5 fenchon and the remaining part consisting of alpha + beta-pinen, limonen (p-mentha-1,8-dien) and estragol [8].

Associations of Kautschiin with other chemical compounds

• Examples are: genistein and EGCG, which effect signaling through the IGF-1/AKT pathway and resveratrol and limonen, which do so through the RAS pathway [9].

References