ChineseMed与icinalChemistry.ppt

Chinese Medicinal Chemistry School of Chinese Pharmacy Beijing University of Chinese Medicine Zengping Gao Sep. 2009 Chapter 9 Terpenoids and Volatile Oils萜和挥发油 * Terpenoids * Volatile Oils 9.1 Terpenoids: Introduction Classification and structure Physical and chemical properties Extraction and isolation Identification Structure elucidation Crude drugs Introdution: 1. Definition: Terpenoids are regarded as derivatives of polymers of isoprene(异戊二烯), usually joined head to tail or tail to tail. The isoprene units arise biogenetically from mevalonic acid (MVA) and are branched-chain, five-carbon units containing two unsaturated bonds. 2. Biosynthesis: 3. Distribution: wide gymnosperm (裸子植物) angiosperm (被子植物) fungi (菌类) marine organisms (海洋生物) 4. Uses: Pharmaceuticals, perfumery, soaps, cosmetics, incense-sticks(熏香), foods and beverage industries etc. Antiseptic(防腐), stimulant, carminative (驱风), diuretic(利尿), analgesic etc. Insecticides (杀虫剂), deodorants(除臭剂) 5. Bioactivity： （1）Circulation system：抗血小板聚集、扩张心脑血管、降压、降脂等——芍药苷、银杏内酯 （2）Digestive system：保肝降酶、利胆健胃、抗溃疡等——齐墩果酸、甘草次酸、环烯醚萜 （3）Respiration system：平喘、祛痰、镇咳等——穿心莲内酯、辣薄荷酮 （4）Nervous system：镇静、局麻、兴奋中枢等——龙脑、高乌头碱、缬草环氧三酯 （5）Anti-tumour：紫杉醇、冬凌草素、雷公藤内酯 （6）抗生育：棉酚、芫花酯甲、乙 （7）Insecticide：青蒿素、川楝素 （8）Spices：甜菊苷、香叶醇 Classification and structure The basis for the classification: the number of isoprene units Monoterpenoids 2 C10H16 Sesquiterpenoids 3 C15H24 Diterpenoids 4 C20H32 Sesterterpenoids 5 C25H40 Triterpenoids 6 C30H48 Tetraterpenoids 8 C40H64 Polyterpenoids n (C5H8)n 1. Monoterpenoids单萜： 是挥发油中低沸点部分的主要组成成分，其含氧衍生物多具有较强的生物活性及香气，是医药、化妆品和食品等的重要原辅料。 acyclic无环 monocyclic单环(troponoids卓酚酮类) bicyclic双环 iridoids环烯醚萜类 Monoterpenoids: Acyclic Monocyclic Bicyclic : Iridoids (环烯醚萜类) 4-demethyliridoid