coumarins.pptVIP

Phenylpropanoids contents Section 1 Introduction Section 2 simple phenylpropanoids Section 3 coumarins Section 4 lignans Section 1 Introduction concepts： chemical compounds with one or several C6-C3 units。 Including: —— simple phenylpropanoids(简单苯丙素类) 、 coumarins(香豆素)、 lignans (木脂素)、 flavonoids(黄酮)、lignins(木质素) 。 苯丙素类化合物生物合成途径 Section 2 simple phenylpropanoids Section 3 coumarins Ⅰ structure and classification Ⅱ. physical and chemical properties Ⅲ extraction and isolation Ⅳ spectroscopy characteristics of coumarins 香豆素母核为苯骈α-吡喃酮。 Ⅰ structure and classification 1.Simple coumarins (简单香豆素) 2. furanocoumarins(呋喃香豆素类) (linear and angular) 3. pyranocoumarins(吡喃香豆素类) (linear and angular) 4. other coumarins (其他香豆素类) 1. Simple coumarins only have substituents on benzene ring 2. Furanocoumarins (呋喃香豆素类) 香豆素核上的异戊烯基常与邻位酚羟基（7-羟基）环合成呋喃或吡喃环，前者称为呋喃香豆素。 3. pyranocoumarins(吡喃香豆素类) 香豆素C-6或C-8异戊烯基与邻酚羟基环合而成2,2-二甲基-α-吡喃环结构，形成吡喃香豆素。这一类天然产物并不多见。 吡喃香豆素类成分的生物合成途径： 4. Other coumarins (其他香豆素) coumarins with substituents on α-pyrone; biscoumarins（双香豆素）; Isocoumarins（异香豆素） Ⅱ. Properties 1. description most of free coumarins are crystal with obvious melting point, but some coumarins are liquid. Free coumarins with small molecular weight have fragrant smell and volatility, can sublime. Coumarin glycoside are powder or crystal, can’t volatile and sublime. Under UV light, coumarins have blue or purple fluorescence. 2. solubility H2O EtOH MeOH CHCl3 Et2O Free coumarin _ + + + + Coumarin glycoside + + + _ _ 3. hydrolysis of lactone ( open and close ring reaction) 4. Reaction with acid 指异戊烯基双键开裂并与邻酚羟基环合 形成环的大小决定于中间体阳碳离子的稳定性 5. Addition reaction 在控制条件下氢化，先后顺序为： 非共轭的侧链双键 和苯环共轭的呋喃环或吡喃环上的双键 C3、C4双键 6. Color reaction 6.1 . Ferric hydroxamic acid异羟肟酸铁反应（识别内酯）