ste铭roids.pptVIP

steroid Section 1 introduction categories and structure characteristics of natural steroids Section 2 cardiac glycosides steroid glycoside, physiological activity to heart. No cardiac glycosides from animal. Toad venom also show physiological activity, but it doesn’t belong to glycosides, belong to ester of liphatic acids. Ⅱ structure and classification 1. the structure of aglycone five-membered unsaturated lacone (Δαβ-γ-lactone) six-membered unsaturated lacone (Δαβ,γδ-δ-lactone) structure characteristics: (1) A/B: cis or trans, but most are cis; B/C: trans; C/D: most cis (2) C3-OH, C14-OH; C3-β-OH, few are α-OH (called epi-), C3-O- saccharide; C14-β-OH, dewater with C15-H. (3) C10 – CH3, CHO, CH2OH, COOH; C13-CH3 (4) C11, C12, C19 C=O 2. the structure of saccharide2.1 α-OH saccharide 2.2 α-deoxy saccharide 3. the connecting type of aglycone and  saccharide Type Ⅰ aglycone-(2,6-deoxysaccharide)x-(D-glucose)y Type Ⅱ aglycone-(6-deoxysaccharide)x-(D-glucose)y Type Ⅲ aglycone-(D-glucose)y Ⅲ the relationships between structure and activity 1. steroid part: C/D: cis， C14-βOH. if A/B cis, the C3-OH must be β-OH, if A/B trans, C3-αOH C3-βOH. 2. unsaturated latone C17-β-unsaturated lactone. If the lactone is saturated, the activity decrease. 3. substituent C10-CH3 change to C10-CHO or CH2OH, the activity increase C10-CH3 change to C10-C0OH or H, the activity decrease 4. saccharide part 甲型： trisaccharides cardiac glycoside bisaccharides cardiac glycoside monosaccharides cardiac glycoside cardiac aglycone 乙型: cardiac aglycone monosaccharides cardiac glycoside bisaccharides cardiac glycoside Ⅳ Properties 1. Description colorless crystal or amorphous powder; optical activity; C17-β：bitter； C17-α：not bitter, no physiological activity; stimulation to mucosa. 2. Solubility cardiac glycoside can dissolve in H2O, alcohol, acetone； slightly dissolve in EtOAc, CHCl3 containing alcohol, can’t dissolve in Et2O, benzene, p.e. The