The synthesis and membrane protective properties of sulfanyl imines derived from neomenthane and isobornane thiols

Synthesis and Antioxidant Activity of Carane and Pinane Based Sulfenimines and Sulfinimines

“…Antioxidant activity (AOA) of compounds 3a – 5a , 4b , 5b , ( S )‐ 3a –( S )‐ 5a , ( R )‐ 3a –( R )‐ 5a , ( S )‐ 4b , ( S )‐ 5b , ( R )‐ 4b and ( R )‐ 5b was evaluated in the cellular (red blood cells) and non‐cellular (lipid‐containing brain homogenate) model systems that we used earlier in the study of the neomenthane and isobornane sulfenimines, as well as cis ‐ and trans ‐myrtanylthiotriazoles, caranylthiotriazoles, and neomenthylthiotriazoles …”

“…Antioxidant activity (AOA) of compounds 3a-5a, 4b, 5b, (S)-3a-(S)-5a, (R)-3a-(R)-5a, (S)-4b, (S)-5b, (R)-4b and (R)-5b was evaluated in the cellular (red blood cells) and non-cellular (lipid-containing brain homogenate) model systems that we used earlier in the study of the neomenthane and isobornane sulfenimines, [6] as well as cis-and trans-myrtanylthiotriazoles, caranylthiotriazoles, and neomenthylthiotriazoles. [7,8] In non-cellular model system, the highest antioxidant activity has been shown by derivatives with the p-nitrobenzylidene moiety (carane sulfinimines (S)-4a and (R)-4a, pinane sulfenimine 4b and sulfinimines (S)-4b, (R)-4b), as well as pinane sulfenimine 5b with 2hydroxybenzylidene moiety at both concentrations (100 μM and 1 mM) ( Figure 3).…”

“…The nitro derivatives 4a and 4b without a sulfinyl group showed the highest membrane-protective and antioxidant activity in H 2 O 2 -induced erythrocytes hemolysis ( Table 1), which is consistent with the previously obtained data. [6] These sulfenimines significantly increased cell survival, actively prevented the accumulation of lipid peroxidation (LPO) secondary products and the oxidation of native hemoglobin.…”

“…[2,3] It is known that essential oils, which include monoterpenoids, as well as individual monoterpenoids, have antioxidant properties. [4,5] Earlier, we revealed that the sulfenimines with the neomenthane and isobornane structures were able to protect red blood cells in vitro from oxidative stress induced by the H 2 O 2 and AAPH, [6] and it was also found that sulfenimines with the nitro group in the para-position of the benzylidene substituent were more active. Antioxidant and membrane-protective activity of cis-and trans-myrtanylthiotriazoles was revealed.…”

Caryophyllane Thiols, Vinyl Thioethers, Di‐ and Bis‐Sulfides: Antioxidant and Membrane Protective Activities

“…It promotes the synthesis of glutathione and decreases the formation of reactive oxygen species (ROS) in cells preventing the oxidative stress . Some di‐ and bis‐sulfides, as well as sulfenimines with monoterpenic fragments exhibit antioxidant properties. Antioxidant properties are noted for epoxy compounds including terpene derivatives …”