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Studies on Natural Terpenoids and Stilbenoids

Author: WuBin
Tutor: PanYuanJiang
School: Zhejiang University
Course: Organic Chemistry
Keywords: Diterpenoid Sesquiterpene Stilbene compounds Diphenyl evil G English Structure identification Derivative synthesis
CLC: O629.61
Type: PhD thesis
Year: 2007
Downloads: 492
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Abstract


Natural occurring terpenoids and stilbeniods play important roles in natural products chemistry owning to their wide range of biological activities. In this dissertation, phytochemical studies on the terpenoids and stilbeniods from two plants led to the isolation of 19 new compounds. Their structures were elucidated by chemical and spectral evidences, and some biological active compounds were further sythesized.The chemical study on the methanol extracts of the roots of Chloranthus henryi Hemsl. lead to the isolation and identification of 13 new compounds together with 21 known compounds. Their structures were elucidated on the basis of spectral and chemical evidence. The 13 new compounds were determined as follows: 14-methoxy-15,16-dinor-5αH-9αH-labda-13(E),8(17)-dien-12-one, 12,15-epoxy-5αH-9βH-labda-8(17),13-dien-19-oic acid, (13S)-13-hydroxy-19-methoxy-5Ah-labda-8 (17), 14-dien, 1α-hydroxyl-8,12-epoxy-eudesma-4,7,11-trien-6,9-dione, 4β-hydroxy-8,12-epoxy eudesma-7, 11-dien-1, 6-dione, 1α-methoxy-8, 12-epoxy eudesma-4, 7, 11-trien-6-one, 7βH-eudesma-4(14)-en-8-one-12-oic acid, 11β-hydroxy-3αH-cadina-5, 7, 9-trien-12, 8-olide, 11β-hydroxy-3βH-cadina-5, 7, 9-trien-12, 8-olide, 5-hydroxyl-3αH-10αH-cadina-6(11), 9(15)-dien-8,12-olid, 8-hydroxy-germacra-1(10)E, 4Z, 7(11)-trien-6-one-12, 8-olide, 8-methoxy-germacra-1(10)E, 4Z, 7(11)-trien-6-one-12, 8-olide, and dayejijiol with a new carbon skeleton nemed chlorathane.32 Compounds were isolated from the methanol extracts of Bulbophyllum kwangtungense Schlecht. Their strucrures were elucidated on the basis of spectral and chemical data. Among them, six new compounds were elucidated as 2-methyl-2’3’-dimethoxy-4, 5-methylenedioxybibenzyl, 7, 8-dihydro-5-hydroxy-12, 13-methylenedioxy-11-methoxyldibenz[b, f]oxepin, 4-hydroxy-11, 12, 13-trimethoxyldibe nz[b, f]oxepin, 7, 8-dihydro-3-hydroxy-12, 13-methylenedioxy-11-methoxyldibenz[b, f] oxepin, 7,8-dihydro-4-hydroxy-12,13-methylenedioxy-11-methoxyldibenz[b, f]oxepin, 7, 8-dihydro-4, 11-dimethoxy-12, 13-methylenedioxy-11-dibenz[b, f]oxepin. All new compounds are stilbenoids, including bibezyls and dibenz[b, f]oxepins. Dibenz[b, f]oxepins, which were all new compounds isolated from Bulbophyllum kwangtungense, are very rare in the natural sources.Some new compounds and known compounds were tested for anti-tumor activities in vitro against Hela and K562 human tumor cell lines using the MTT method. Compounds SDL-6, SDL-7, SDL-8, SDL-9, SDL-12, and SDL-15 showed anti-tumor activities.From the starting materials 3, 4, 5-trimethoxy-benzaldehyde and 2, 4-dihydroxybenzaldehyde, the bioactive natural compound 4-hydroxy-11, 12, 13-trimethoxyldibenz[b, f]oxepin(SDL-7) was sythesized with 12.3% yields of nine steps. The target compound and several intermediats were tested for anti-tumor activities in vitro.Another anti-tumor compound erianin(SDL-9) was also sythesized and 17 analogous were obtained. All compounds sythesized were tested for anti-tumor activities in vitro. The spin-labeled derivatives of erianin, 3’-O-(2", 2", 5", 5"-tetramethyl-3"-carboxypyrroline-1"-oxyl-3"methanoyloxyl)-erianin and 3’-O-(2", 2", 6", 6",-tetramethyl-1", 2", 5", 6"-tetrahydropridine-1"-oxyl-4"-methanoylox yl)-erianin, showed promising anti-tumor activities in vitro.These findings demanstrated that natural compounds, 4-hydroxy-11, 12, 13-trimethoxyldibenz[b, f]oxepin, and spin-labeled erianin derivatives deserve further chemical and biological research.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Natural compounds > Aromatic Oils > Terpenoids
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