天然药物化学(沈阳药科大学)-天然药物化学-6-萜类和挥发油化合物

1、第六章 萜类和挥发油化合物 定义：分子式符合(C5H8)n，异戊二烯的聚合体及其衍生物类，其骨架一般以五个碳为基本单位（少数例外）。 分类：单萜、倍半萜、二萜、二倍半萜、三萜、四帖等。萜类的生源学说 一、经验的异戊二烯法则 、将橡胶进行焦化反应，或将松节油的蒸汽经氮气稀释后，低压下通过红热的铂丝网均能获得差旅很高的异戊二烯； 、异戊二烯聚合生成二戊烯。280oC生源的异戊二烯法则SCoAOOSCoAOHOOCCOSCoAHOHOOCCH2OHHOHOOCCH2OPHOHOOCCH2OPPHOOPPOPPOPPHPPOOPPOPPHHOPPOPP焦磷酸香叶酯(GPP)焦磷酸金合欢酯(FPP)单萜

2、薄荷烷侧柏烷蒈烷蒎烷莰烷优香芹烷桂花烷环香叶烷菊花烷蒿烷薰衣草烷链状单萜CH2OHCH2OHCH2OHOH香叶醇橙花醇香茅醇芳樟醇CHOCHOCHO香叶醛橙花醛香茅醛环状单萜CH2OPPOPP2-蒎烯2;蒈烯侧柏烯12345678910+OHOHOHOHO1-薄荷醇异薄荷醇d-新薄荷醇新异薄荷醇薄荷酮CHOH3C C CH3OHC CHC CH3OH2SO4HC CHC CH3OHC CHC CH3O柠檬醛伪紫罗兰酮-紫罗兰酮-紫罗兰酮OHOHOOHCOHOO1-龙脑d-龙脑樟脑-氧化樟脑对-氧化樟脑OOOONOOOOH斑蝥素斑蝥胺OOHOOHHOH2CHOHOOHOO芍药苷卓酚酮类OOHOO

3、HOOH-崖柏素扁柏素-崖柏素环烯醚萜环烯醚萜骨架裂环环烯醚萜骨架CH2OPPCHOCHOCHOCH2OHCHOCHOCHOOHOHHOHOOHHHOOH1234567891011OCOOHOHOOHOOH1234567891011OOOOH1234567891011代表化合物OOHHOH2CHHCOOCH3OH栀子苷OHHCOOROC6H11O5R = CH3, 京尼平苷R = H, 京尼平苷酸OHHOC6H11O5H3CSCOOH2COO鸡屎藤苷OOHOH2COglcHO梓醇OOOOC6H11O5龙胆苦苷OOOHOOOHHHOOOHOOOHHHOOOHOOOHHHOCH3OCH3OOOHO

4、OOHHHOCH2CH3OCOOCH3OglcOOHO倍半萜土青木香烷橄榄烷桉烷香木兰烷双环吉马烷吉马烷OPP+前伊鲁烷蛇麻烷伊鲁烷小皮伞烷丁香烷愈创木烷榄烷艾里莫酚烷缬草烷乌药烷倍半蒈烷没药烷檀香烷菖蒲烷花侧柏烷月桂烷单瑞孢烷长松叶烷胡椒烷杜松烷拉松烷苜蓿烷松香烷恰米烷斧柏烷代表的倍半萜CH2OHHO-金合欢烯-金合欢烯金合欢醇橙花醇OOOOOHHOOOOHOHHOOOOH3COHHOOOOHOOCH2CH2COCOHH青蒿素双氢青蒿素蒿甲醚青蒿琥珀单酯OOOOOCOCH3OO山道年光照CH3COOHOOOOOMsOOOOMsOHHXYOOMsOOHHOOHOHXYOOHOOCHOOOOHO

5、OOHHYXChemical Transformations of -Santonin to Biologically Active Eudesmanolides, Guaianolides, Elemanolides, and Germacranolides+GuaianolidesEudesmanolidesElemanlolidesGermacranolidesSantonineDEBCATNFOHOHOHOOHOHOHOOHOOHOOHOHOHROOHOHOHOTable 9. Inhibitory Activity of Induction of Intercellular Adhe

6、sion Molecule-1 ( ICAM-1 ) d). IC50 ( M )Compd.204205203207IL - 116.435.318.210013.639.113.61002061001008 - deoxylactucinChinensiolide AChinensiolide BChinensiolide EChinensiolide HOOHOO132OOHOHHOOOOO564OOHOHHOOOOOOOHOOOHOHOHHOOHHHHOHOOOHOHOHHOOHOHOOOOHOHHOOHOHOOOHOOOHO二萜紫杉烷维生素A型异右旋松脂烷克罗烷半日花烷右松脂烷卡萨烷

7、phyllocradane贝叶烷松香烷桃柘烷乌头烷贝壳杉烷阿替烷赤霉烷木藜芦毒烷大戟烷瑞香烷穿心莲内酯OOHOHCH2OHHOOOOOOHOOOHOOOOHOOOHCH2OHHOSO3NaNa2SO3 + H2SO4大青素OOOHHOOCOCH3HOH3COCOOOCOCH3OOHHOOCOCH3H3COCOOOHHOOCOCH3H3COCOOOcaryoptin大青素海常黄素A银杏内酯OOOHOR1HR2R3HOOOR1R2R3OHHHOHOHHOHHOHOHOHHOHOHOH银杏内酯 A银杏内酯 B银杏内酯 C银杏内酯 M银杏内酯 J紫杉醇OAcOOHOHOOOHOAcOOOHNHO紫杉醇OHOOHOHOHOOHOAcO二倍半萜OCOOCH3COOH14681012141618202122232425呋喃海绵素 -3OOHCOHHHOH蛇孢假壳素 AHCOOHH网肺酸挥发油 挥发油又称精油，是一类具有芳香气味的油状液体的总称。 组成和分类：萜类化合物；芳香族化合物；脂肪族化合物；其他。 性质：性状：颜色、气味、型态、挥发性；溶解度；物理常数（包括密度、沸点、折光率等）；稳定性挥发油的提