Pearce B C, Parker R A, Deason M E, Qureshi A A, Wright J J
Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492.
J Med Chem. 1992 Oct 2;35(20):3595-606. doi: 10.1021/jm00098a002.
Tocotrienols are farnesylated benzopyran natural products that exhibit hypocholesterolemic activity in vitro and in vivo. The mechanism of their hypolipidemic action involves posttranscriptional suppression of HMG-CoA reductase by a process distinct from other known inhibitors of cholesterol biosynthesis. An efficient synthetic route to tocotrienols and their isolation from palm oil distillate using an improved procedure is presented. gamma-Tocotrienol exhibits a 30-fold greater activity toward cholesterol biosynthesis inhibition compared to alpha-tocotrienol in HepG2 cells in vitro. The synthetic (racemic) and natural (chiral) tocotrienols exhibit nearly identical cholesterol biosynthesis inhibition and HMG-CoA reductase suppression properties as demonstrated in vitro and in vivo.
生育三烯酚是法尼基化的苯并吡喃天然产物,在体外和体内均表现出降胆固醇活性。它们的降血脂作用机制涉及通过一种不同于其他已知胆固醇生物合成抑制剂的过程对HMG-CoA还原酶进行转录后抑制。本文介绍了一种高效合成生育三烯酚的路线以及使用改进方法从棕榈油馏出物中分离它们的方法。在体外HepG2细胞中,γ-生育三烯酚对胆固醇生物合成抑制的活性比α-生育三烯酚高30倍。如体外和体内实验所示,合成(外消旋)和天然(手性)生育三烯酚表现出几乎相同的胆固醇生物合成抑制和HMG-CoA还原酶抑制特性。