大二上 温州医学院第一临床学院-17Lipids-ye.pptVIP

* * * * * * * * * * * * * CHARPTER 15 Steroids Steroids have a variety of uses in human body, including, but not limited to, controlling meiosis, carbohydrate metabolism, fat storage, muscle growth, immune function and nerve cell membrane chemistry, most steroids function as hormones. All steroids possess the fused four-ring structure, whereas the side chains and functional groups exhibit an almost infinite variety. Ⅰ. Base Structure of Steroids Cyclopentanoperhydrophenanthrene A B C D R p h e n a n t h r e n e c y c l o p e n t a n e 17 10 13 The methyl groups on the C10 and C13 position are called the corner methyl groups (角甲基). * * * * * * There are 6 chiral carbon atoms in the ring. Ⅱ. Stereo Structure of Steroids Ring junctions between each ring in the base structure of steroids are similar with decahydronaphthalene. Decahydronaphthalene consists of two cyclohexanes and these two rings can be fused either by cis or trans. If two hydrogens bonded on ring junctions are at the same side of the ring, it is cis-decahydronaphthalene. cis-Decahydronaphthalene trans-Decahydronaphthalene e a fused e e fused, more stable 1. Configuration of natural steroids The B-C and C-D ring junctions are trans, in most cases, but the A-B ring juncture gives rise to 2 series of compounds depending on whether the juncture is cis (normal series) or trans (allo series). Allo series Normal series 5α-Series ：A/B trans fused, B/C and C/D trans fused. allo series (1)α- system The hydrogen of the C5 is on the different side of the ring with the corner –CH3 Allo series 5β-Series ：A/B cis fused, B/C and C/D trans fused. normal series 5 10 9 8 (2) β- system The hydrogen of the C5 is on the same side of the ring with the corner –CH3 Normal series 3α-configuration (1) a-configuration: Substituents are on the different side of ring with the－CH3 2. Configuration of substitutes on the steroid ring (2) b-configuration: substituents are on the same side of ring with the –CH3 3β-configurat