Cytotoxic effect of conjugated trienoic fatty acids on mouse tumor and human monocytic leukemia cells

Abstract

The cytotoxicity of fatty acids from seed oils containing conjugated linolenic acids (CLN) was studied. Fatty acids from pomegranate, tung, and catalpa were cytotoxic to human monocytic leukemia cells at concentrations exceeding 5 microM for pomegranate and tung and 10 microM for catalpa, but fatty acids from pot marigold oil had no effect at concentrations ranging up to 163 microM. The main conjugated fatty acids of pomegranate, tung, catalpa, and pot marigold were cis(c)9,trans(t)11,c13-CLN (71.7%), c9,t11,t13-CLN (70.1%), t9,t11,c13-CLN (31.3%), and t8,t10,c12-CLN (33.4%), respectively. Therefore, the cytotoxicities of fatty acids from pomegranate, tung, and catalpa were supposed to be due to 9,11,13-CLN isomers. To elucidate the cytotoxicity of these CLN, we separated each CLN isomer from the fatty acid mixtures by high-performance liquid chromatography and analyzed its cytotoxicity. The cytotoxicities of c9,t11,c13-CLN, c9,t11,t13-CLN, and t9,t11,c13-CLN were much stronger than that of t8,t10,c12-CLN. Therefore, the higher cytotoxicity of fatty acids from pomegranate, tung, and catalpa than those from pot marigold would be derived from the different activities of 9,11,13-CLN and 8,10,12-CLN. Since there was little difference in the cytotoxicities of c9,t11,c13-CLN,c9,t11,t13-CLN, and t9,t11,c13-CLN, it is suggested that the cis/trans configuration of 9,11,13-CLN isomers had little effect on their cytotoxic effects. The mechanism of the cytotoxicity of the four fatty acids above may involve lipid peroxidation, because the order of toxicity of the fatty acids was consistent with their susceptibility to peroxidation in aqueous phase. This was supported by the decrease in the cytotoxicity of the fatty acids by addition of butylated hydroxytoluene.

Incorporation and profile of fatty acids in tilapia fillets (Oreochromis niloticus) fed with tung oil

“…Some of its isomers have proven biological activity (SEÇKIN et al, 2005;SUZUKI et al, 2001;YASUI et al, 2005).…”

“…Some CLnA isomers show cytotoxic effects on tumors, inhibit carcinogenesis, and alter lipid metabolism (DESTAILLATS et al, 2005;SUZUKI et al, 2001;YASUI et al, 2005).…”

Catalpa seed oil rich in 9t,11t,13c-conjugated linolenic acid suppresses the development of colonic aberrant crypt foci induced by azoxymethane in rats

“…(17). Also we and other researchers have shown the cytotoxic effect of PGO and tung oil on a variety of human cancer cell lines, including colon cancer cells (18,19).…”

“…In addition, our recent studies demonstrated that BMO and PGO suppressed azoxymethane (AOM)-induced colon carcinogenesis in rats (12,22). Regarding catalpa seed oil (CPO), we reported the cytotoxic effect of CPO on SV40-transformed Balb 3T3 A31 and human monocytic leukemia cell lines (18), but there are no in vivo studies on the effect of CPO on carcinogenesis.…”

Enzymatic synthesis of structured lipids containing conjugated linolenic acids extracted from pomegranate seed oil and their physicochemical characteristics

“…CLnA는 필수지방산(n-3)인 리놀렌산(α-linolenic acid, C18:3, cis(c)9, c-12, c-15)의 위치기하학적 이성질체로 공 역화이성체인 공액알파리놀렌산은 모두 탄소수가 18개이 며, conjugated의 이중결합을 갖는 이성체인 지방산의 구조 를 갖는다 (Suzuki et al, 2001). CLnA의 대표적인 isomer 형태인 punicic acid(c9 trans(t)11, c13-CLnA)는 석류 종 자유에 약 80%가 함유되어있다 (Cao et al, 2007) A (NH-SL) : it was synthesized at non-solvent (no n-hexane) system (NH-SL) using 1:6 molar ratio of palm stearin (PS) and HPSO for 72 hr in a shaking water bath set at 65℃ and 185 rpm, B (H-SL) : it was synthesized at solvent (n-hexane) system (H-SL) using 1:6 molar ratio of palm stearin (PS) and HPSO for 72 hr in a shaking water bath set at 65℃ and 185 rpm.…”