Oxidative Cleavage Products of ${\zeta}-Carotene$

${\zeta}-Carotene$의 산화개열산물

${\zeta}-Carotene$ was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector. ${\zeta}-Carotene$ was solubilized in toluene, and then oxidized by incubating at $37^{\circ}C$, 72 hr under atmospheric oxygen. Carbonyl compound and acidic compound were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra were identical to the reference cleavage products prepared by ozonolysis of ${\zeta}-carotene$. Absorption spectrum of acidic compound was similar to that of standard 4,5-didehydrogeranyl geranyl acid which is known to possess biological activity. Thus, eccentric cleavage of ${\zeta}-carotene$ was confirmed to occur in vitro under oxidation condition.

${\zeta}-Carotene$를 dichloromethane에 용해하고 dry ice 상에서 ozonolysis을 행하였다. Ozonolysis에 의해 생성된 화합물은 silica gel chromatography를 행하여 분획하고, photodiode array detector를 이용하여 ODS-HPLC로 분석하였다. Toluene에 ${\zeta}-carotene$을 용해하고 $37^{\circ}C$, 72시간 자동산화시킨 결과, 다수의 carbonyl 및 acidic화합물이 생성되었다. ${\zeta}-Carotene$의 자동산화로부터 생성된 carbonyl 화합물의 대부분은 ozonolysis에 의하여 얻어진 산화개열산물이 나타내는 HPLC상의 거동과 분광학적 특성이 서로 잘 일치하였다. 또한 ${\zeta}-carotene$의 자동산화에 의해 생성된 중앙개열 acidic 화합물은 생물활성을 나타내는 4,5-didehydrogeranyl geranyl acid 표준품과 동일한 분광학적 특성을 나타냈다. 이러한 결과는 in vitro상의 산화적 조건하에서 ${\zeta}-carotene$ 자동산화에 의해 eccentric cleavage가 생성됨을 알 수 있었다.