Study On The Chemical Constituents Of The Sesquiterpenes From The Root Of The Big Elephant

The thesis included two parts of studies on the chemical constituents and bioactivity from stems of Pieris jormosa and studies on the sesquiterpenes from the roots of Illicium majus.Pieris formosa is a species of Pieris D. Don, Ericaceae, with nicknames of xingshan Ma Zuimu, long beautiful Ma Zuimu, bubble flower and red candle tree. Pieris formosa is distributed in zhejiang, jiangxi, hubei, hunan, guangdong, guangx i, sichuan, guizhou, yunnan provinces of China and Vietnam, Myanmar, Nepal, B hutan, India. It was born in the brush at an altitude of900-2300meters. Pieris f ormosa is poisonous and can lead to coma, difficulty breathing and movement dis order, when people and animals eat it carelessly. As a traditional folk medicine, t he leaves and roots have been used to treat vomit, diarrhea and scabies. It is also can be used as a pesticide to kill pests. Up to now, the chemical constituents of Pieris formosa have been well investigated by many scholars. According to the r eports, its main chemical composition are flavonoids, terpenoids, phenol glycosides, steroids, lignanoids and some alkaloids. In order to further understand the chemica1composition and the material basis of biological activity of Pieris formosa, we had studied the stems and isolated60compounds, including seventeen diterpenoid s (1*-10*,11-17), two sesquiterpenes (18-19), two triterpenes (20-21), fourteen flav onoids (22-35), four ligninoids (36*-37*,38-39), five phenylpropanoids (40-44) and seventeen other type compounds (45-60). Among these compounds,12were new compounds (marked*). Through spectroscopy analysis and chemical methods, th eir structures were identified as pieristoxin L-U (1*-10*), grayanoside D (11), rho domolin I (12), pieristoxin H (13), grayanotoxin Ⅱ (14), pierisformoside B (15), grayanoside C (16),bis-deacetylkalmitoxin-VI (17),(3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (18),(3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol-3-O-β-D-glucopyranoside (19), oleanolic acid (20), betulinic acid (21),(+)-catechin (22),(2R,3S)-3,3’4’,5,6,7,8-heptahydroxyflavan (23), Dulcisflavan (24),(2R,3R)-dihydroquer cetin (25), phlorizin (26), asebotin (27),3-hydroxyasebotin (28), quercitrin (29), af zelin(30), kaempferol-3-O-β-D-glucoside (31), hirsutrin (32), apigenin-7-O-O-β-glucopy ranoside (33), quercetin-3-O-β-L-arabinopyranoside (34), quercetin-3-O-D-xylopyrano side(35),8R-2,4-dimethoxy-3,3’,5’3hydroxy-8-hydroxy methyl-9’-O-β-buckthorn indic an-9-4’-lignan (36*),(7R,8R)-4-dimethoxy-3,3’,5’-dihydroxy-8-hydroxy methyl-9’-O-β- buckthorn indican-9-4’-lignan (37*),(7S,8R,7’E)-4-hydroxy-3,5’-dimethoxy-4’,7-epoxy-8,3’-neolign-7’-ene-9,9’-diol-methyl ether (38), pinoresinol (39),1-(4-hydroxy-3-meth oxyphenyl)propane-1,2,3-triol (40),2,3-dihydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl) propan-1-one (41),3-(3,4-dihydroxyphenyl)-1-propanol (42),4-(3-hydroxypropyl)-2-methoxyphenol (43),4-(3-hydroxypropyl)-2,6-dimethoxyphenol (44), Butan-2-(O-/β-D-glucopyranoside (45),(3R,5R)-3-hydroxy-5-hexanolide (46),(3S,5S)-3-hydroxy-5-hex anolide (47), benzyl-O-β-D-glucopyranoside (48),(E)-4-(2-hydroxyvinyl)phenol (49),4-ethoxy-2,3-dihydroxybutanoic acid (50), syrangaldehyde (51),4-hydroxy-3,5-dime thoxy-benzoic acid (52),5-methylbenzene-1,3-diol (53),4-(2-hydroxyethyl)phenol (54), dibutyl phthalate (55), orcinol glucoside (56),4-(2-hydroxyethyl)benzene-1,2-d iol (57),3,5-dihydroxy-2-hydroxymethyl-4H-pyran-4-one (58),3-hydroxy-2-hydroxy methyl-4H-pyran-4-one (59),3,5-dihydroxy-2-methyl-4H-pyran-4-one (60).The new diterpenes isolated from Pieris formosa could be classified to grayannane type dite rpenoids, which have multiple chiral center. The relative configuration was determi ned by comprehensive analysis of1D and2D NMR, including1H NMR,13C NM R, DEPT, HSQC, HMBC,’H-’H COSY and NOE. Then the absolute configuratio n was determined by calculated ECD.Illicium majus Hook et Thorns belongs to the genus Illicium of the Illiciacea e, which is mainly distributed in southern China, eastern Burma and northern Viet nam, the fruit and bark are poisonous. As traditional folk medicine it used to trea t the diagnosis tenderrnness and vomiting. The present studies are mainly sesquiter penoids, in order to further clarify the chemical composition, ten compounds were isolated from the roots of Illicium majus by application of various chromatograph ic technologies. These compounds include seven sesquiterpenoids (61-67), two phe nolic acids (68,69) and one phenylpropanoid (70). On basis of spectroscopic and chemical methods, their structures were determined as:cycloparviflorolide (61), c ycloparvifloralone (62), tashironin (63), tashironin A (64), anislactone A (65), anisl actone B (66), pseudomajucin (67), syringaldehyde (68), methyl-4-hydroxy-3,5-dime thoxybenzoate (69)和(E)-3-methoxy-4,5-methylenedioxycinnamic alchol (70).