| 研究生: |
高安平 Kao, An-Ping |
|---|---|
| 論文名稱: |
南嶺前胡葉部與廣東山葡萄之成分研究 The constituents of the leaves of Peucedanum longshengense and whole plant of Ampelopsis cantoniensis |
| 指導教授: |
吳天賞
Wu, Tian-Shung |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2006 |
| 畢業學年度: | 94 |
| 語文別: | 中文 |
| 論文頁數: | 156 |
| 中文關鍵詞: | 南嶺前胡 、廣東山葡萄 |
| 外文關鍵詞: | peucedanum longshengense, ampelopsis cantoniensis |
| 相關次數: | 點閱:101 下載:2 |
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由南嶺前胡(Peucedanum longshengense)之葉部分離得到39個化合物,其中38個分別為:scopoletin (1)、 (R)-peucedanol (2)、 bergapten (31)、 isoimperatorin (32)、 (-)-(R)-oxypeucedanin (33)、 (+)-oxypeucedanin hydrate (34)、 (-)-pangelin (39)、 (+)-marmesin (72)、 deltoin (77)、 3'-(S)-4'-(S)-khellactone (132)、qainhucoumarin C (134)、 3'-(S)-4'-(S)-4'-tigloylkhellactone (136)、 laserpitin (135)、 qainhucoumarin D (139)、 pteryxin (142)、 3'-(S)-O-acetyl-4'-(R)-O- tigloylkhellactone (161)、 isoquercitrin (186)、 -sitosterol(228)、 stigmasterol (229)、 -sitosteryl-3-O--glucopyranoside (230)、 9-hydroxy-4-(3-methylbut-2- enyloxy)furo[3,2-g]chromen-7-one (253)、 isooxypeucedanin (254)、 3'-(S)-O- tigloyl-4'-(S)-O-acetylkhellactone (255)、 (-)-isosamidin (256)、 3'-(R)-acetoxy-4'-(S)- hydroxy-3',4'-dihydroseselin (257)、 peucedanoside-A (258)、 peucedanoside-B (259)、 (+)-8-hydroxy-p-menth-6-en-7-al (260)、 3-hydroxy-4- isopropylcyclohexenecarbaldehyde (261)、 (+)-syringareainol (262)、 perlolyrin (263)、 lycoperodine-1 (264)、 3,4-dimethoxyacetophenone (265)、 2-acetyl-5- hydroxymethylphenol (266)、 2-oxyl-4-methyl-acetophenon (267)、4-hydroxycinnamic acid (268)、 N-tetracosanoyltyramine (269)、 erythritol (270)。其中peucedanoside-A (258)、 peucedanoside-B (259) 和(+)-8-hydroxy-p-menth-6- en-7-al (260)為首次報導之新化合物。
研究發現由南嶺前胡葉部分離得到的成分與大陸學者P. Huang對本植物之根部所做的研究相似,皆含大量的khellactone type骨架衍生物。由所分離得到的khellactone type骨架化合物與過去報導的此類化合物歸納出判別khellactone type 骨架上C-3'與C-4'相對立體位向的快速簡易方法。
另外著手研究廣東山葡萄(Ampelopsis cantoniensis)之化學成分,並分離得到21個化合物,其中18個分別為:scopoletin (1)、 scoparone (3)、 syringic acid (318)、 3,4,5-trimethoxy-benzenemethanol (319)、 pinoresinol (320)、 -sitosterol (228)、 - sitosteryl----D-glucoside (230)、 stigmast-4-en-3-on (321)、stigmasta-4,22-dien-3-on (322)、 6-hydroxystigmast-4-en-3-one (323)、6-hydroxystigmast-4-en-3-one (324)、 betulinic acid (325)、 ursolic acid (326)、132(S)-methoxypheophorbide-a (327)、 methyl 21-hydroxy-21(S)-pheophorbide-a (328)、 132(S)-methoxypheophorbide-a methyl ester (329)、 methyl-21-hydroxy- 21(S)-pheophorbide-a (330)、 methyl-21-hydroxy-21(R)-pheophorbide-b(331)。
研究發現由廣東山葡萄分離得到的成分以sterols 和chlorophylls 含量最多,與它種植物差異性較大。
以上新化合物的結構乃利用NMR 1D與2D光譜的分析加以決定,而已知的化合物則是與文獻所報導的物理與化學光譜數據進行比對得到確認。
Detailed chemical examination of the MeOH extract of the leaves of Peucedanum longshengense has led to the isolation of thirty-nine compounds. Among them, thirty-eight compounds were identified by spectroscopic analyses as scopoletin (1), (R)-peucedanol (2), bergapten (31), isoimperatorin (32), (-)-(R)-oxypeucedanin (33), (+)-oxypeucedanin hydrate (34), (-)-pangelin (39), (+)-marmesin (72), deltoin (77), 3'-(S)-4'-(S)-khellactone (132), qainhucoumarin C (134), 3'-(S)-4'-(S)-4'- tigloylkhellactone (136), laserpitin (135), qainhucoumarin D (139) , pteryxin (142), 3'-(S)-O-acetyl-4'-(R)-O-tigloylkhellactone (161), isoquercitrin (186), -sitosterol (228), stigmasterol (229), -sitosteryl-3-O--glucopyranoside (230), 9-hydroxy- 4-(3-methylbut-2-enyloxy)furo[3,2-g]chromen-7-one (253), isooxypeucedanin (254), 3'-(S)-O-tigloyl-4'-(S)-O-acetylkhellactone (255), (-)-isosamidin (256), 3'- (R)-acetoxy-4'-(S)-hydroxy-3',4'-dihydroseselin (257), peucedanoside-A (258), peucedanoside-B (259), (+)-8-hydroxy-p-menth-6-en-7-al (260), 3-hydroxy- 4-isopropylcyclohexenecarbaldehyde (261), (+)-syringaresinol (262), perlolyrin (263), lycoperodine-1 (264), 3, 4-dimethoxyacetophenone (265), 2-acetyl- 5-hydroxymethylphenol (266), 2-hydroxy-4-methylacetophenone (267), 4-hydroxycinnamic acid (268), N-tetracosanoyltyramine (269),and erythritol (270).
Compounds, peucedanosides-A (258), peucedanosides-B (259), and (+)-8- hydroxy-p-menth-6-en-7-al (260), were new compounds.Roots of P. longshengense were reported as rich source of khellactone type coumarins. As expected, the leaves of titled plant has also yielded several khellactone derivatives. It is worthy to mention that with the experience of spectral analysis of several kallactone derivatives, I found an easy method to distinguish the cis and trans forms of substituents at C-3' and C-4'.
In addition, a thorough investigation of the MeOH extract of whole plant of Ampelopsis cantoniensis for its chemical constituents resulted in the isolation of twenty-one compounds. Of which, eighteen compounds were identified by detailed spectral analyses as scopoletin (1), scoparone (3), syringic acid (318)、3,4,5-trimethoxybenzylalcohol (319), pinoresinol (320), -sitosterol (228)、-sitosteryl----D-glucoside (230), stigmast-4-en-3-one (321), stigmasta- 4,22-dien-3-one (322), 6-hydroxystigmast-4-en-3-one (323), 6- hydroxystigmast-4-en-3-one (324), betulinic acid (325), ursolic acid (326), 132(S)-methoxypheophorbide-a (327), methyl 21-hydroxy-21(S)-pheophorbide-
a (328), 132(S)-methoxypheophorbide-a methyl ester (329), methyl-21- hydroxy-21(S)-pheophorbide-a (330), and methyl-21-hydroxy-21(R)-pheophorbide- b(331).These results indicated that A. cantoniensis contained lot of sterols and chlorophylls.
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