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研究生:楊玉良
研究生(外文):Yu-Liang Yang
論文名稱:番荔枝莖部及種子之化學成分及其生物活性研究
論文名稱(外文):Studies on the Chemical Constituents and Biological Activities of Stems and Seeds of Annona squamosa L.
指導教授:吳永昌
指導教授(外文):Yang-Chang Wu
學位類別:博士
校院名稱:高雄醫學大學
系所名稱:藥學研究所博士班
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2004
畢業學年度:92
語文別:英文
論文頁數:337
中文關鍵詞:番荔枝莖部種子對映-貝殼杉烷二? 類番荔枝科乙醯生合成物生物鹼與醯胺類環? 類木質素
外文關鍵詞:Annona squqmosastement-kaurane diterpenoidsseedcyclic peptidesalkaloids and amidesAnnonaceous acetogeninslignanoids
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番荔枝科植物在農業及民間醫藥上有相當的重要性。在台灣產番荔枝科的植
物化學成分研究中,本實驗室發現許多新奇且具生物活性的化合物。本次研究的
目的在於尋找番荔枝中具有生物活性的成分,並且研究過去文獻中未曾報導的部
分。
由番荔枝的莖部與種子中得到76 個化合物,包括20 個對映-貝殼杉烷二?
類化合物、10 個生物鹼與醯胺類化合物、7 個環? 類化合物、18 個番荔枝科乙
醯生合成物、15 個木質素以及6 個其他類的化合物。其中有20 個新化合物,分
別為:annomosin A、annosquamosins C-G、annosqualine、dihydrosinapoyltyramine、
cyclosquamosins H-I、squadiolins A-C、squamostatins-F-G、squamocin-P、squadecins A-B 、squadinorlignoside 與(6R,7S,8S)-1-methoxyisolariciresinol-7a-O-b-Dglucoside。此外,有34 個化合物首次由本植物分離得到。所有化合物的結構皆
由各種光譜資料(紫外光譜、紅外光譜、圓二色光譜、核磁共振光譜、質譜等)
的分析與化學方法加以證明確定。
本次實驗中發現許多化合物具有明顯的生物活性。在抗血小板凝集試驗中,
兩個對映-貝殼杉烷二? 類化合物,ent-kaur-16-en-19-oic acid 與16a-hydro-
19-al-ent-kauran-17-oic acid,在200 mM 時能完全抑制由collagen 誘發的血小板凝
集反應。在抑制超氧陰離子試驗中,發現第四位置接有羧基或羥基的對映-貝殼
杉烷二? 類化合物具有明顯的抑制作用。同時也針對對映-貝殼杉烷二? 類化合
物的抗冠狀病毒以及抗Vero E6 病毒活性進行研究。其中16b,17-dihydroxyent-
kauran-19-oic acid 針對兩種病毒皆有微弱的抑制作用。在細胞毒殺試驗方
面,針對五種不同的癌細胞進行研究,發現大部分的番荔枝科乙醯生合成物皆顯
現出細胞毒殺效果。其中對Hep G2 細胞株有明顯的毒殺作用。此外也發現環?
類化合物cyclosquamosins A 和 D 對Hep G2 細胞株具有微弱的細胞毒殺作用。
Annonaceous plants are of appreciable importance in agriculture and folk
medicine. In the phytochemical studies of Formosan Annonaceous plants, a number of novel and bioactive chemical constituents have been isolated by our lab. The aim of this project is to obtain the bioactive principles from Annona squamosa L. and investigate the components which have never been reported in literatures.
Seventy six compounds, including twenty ent-kaurane diterpenoids, ten alkaloids and amides, seven cyclic peptides, eighteen Annonaceous acetogenins, fifteen lignanoids, and six miscellaneous compounds, were isolated from the stems and seeds of this species. Among them, twenty compounds, annomosin A, annosquamosins C-G, annosqualine, dihydrosinapoyltyramine, cyclosquamosins H-I, squadiolins A-C, squamostatins-F-G, squamocin-P, squadecins A-B, squadinorlignoside, and (6R,7S,8S)-1-methoxyisolariciresinol-7a-O-b-D-glucoside, were reported as new ones and thirty four compounds were isolated from this plant for the first time. All structures were elucidated by spectroscopic data interpretation (UV, IR, CD, NMR, Mass, and so on) and chemical evidences.
Several compounds showed significant activities. Two ent-kauranes, ent-kaur-16-en-19-oic acid and 16a-hydro-19-al-ent-kauran-17-oic acid, showed complete inhibition on platelet aggregation induced by collagen at 200 mM. The ent-kauranes with C4-COOH or C4-OH group showed significant inhibitory effect on superoxide anion generation. The anti-corona virus assay and anti-Vero E6 virus assay of ent-kauranes were also investigated. 16b,17-Dihydroxy-ent-kauran-19-oic acid showed mild inhibitory effect in these two assays. Most Annonaceous acetogenins showed strong to moderate cytotoxicity against various cancer cell lines, especially against Hep G2 cell. Furthermore, two cyclic peptides, cyclosquamosins A and D, showed mild cytotoxicity against Hep G2 cell.
List of Tables ·······························································V
List of Figures ···························································VIII
List of Abbreviations and Symbols ··········································XVI
Acknowledgement ·····························································XX
CHAPTER I INTRODUCTION ·······················································1
Drug Discovery and Development from Natural Sources ··························1
Taxonomic Background of Annona squamosa L. ···································4
Previous Studies on A. squamosa ··············································7
Object of the Present Study ·················································32
CHAPTER II EXPERIMENTAL ·····················································34
General ·····································································34
Biological Activities Studies ···············································36
Plant Materials ·····························································36
Extraction and Isolation ····················································37
CHAPTER III STRUCTURE ELUCIDATION OF ENT-KAURANES AND THEIR BIOLOGICAL ACTIVITIES ····················47
SECTION 3-1: Annomosin A (K1) ···············································49
SECTION 3-2: Annosquamosin C (K2) ···········································57
SECTION 3-3: Annosquamosin D (K3) ···········································63
SECTION 3-4: Annosquamosin E (K4) ···········································69
SECTION 3-5: Annosquamosin F (K5) ···········································75
SECTION 3-6: Annosquamosin G (K6) ···········································81
SECTION 3-7: Pharmacological Study of ent-Kauranes ··························87
SECTION 3-8: Structure Elucidation of ent-Kaurane Diterpenoids ··············93
SECTION 3-9: Physical and Spectral Data of ent-Kaurane Diterpenoids ········107
CHAPTER IV STRUCTURE ELUCIDATION OF ALKALOIDS AND AMIDES ···················113
SECTION 4-1: Annosqualine (A1) ·············································115
SECTION 4-2: Dihydrosinapoyltyramine (A3) ··································123
SECTION 4-3: Physical and Spectral Data of Alkaloids and Amides ············127
CHAPTER V TOTAL SYNTHESIS OF 3,4-DIHYDROBENZO[h]QUINAZOLIN-4-ONE ···········129
CHAPTER VI CYCLIC PEPTIDES- STRUCTURE ELUCIDATION,PHYTOCHEMICAL ANALYSIS, AND BIOASSAYS ··································································143
SECTION 6-1: Cyclosquamosin H (C1) ·········································145
SECTION 6-2: Cyclosquamosin I (C2) ·········································155
SECTION 6-3: Squamin A (C3) and B (C4) ·····································165
SECTION 6-4: Cherimolacyclopeptide B (C5) ··································183
SECTION 6-5: Physical and Spectral Data of Cyclic Peptides ·················193
CHAPTER VII ANNONACEOUS ACETOGENINS- STRUCTURE ELUCIDATION AND THEIR CYTOTOXICITY ·······························································195
SECTION 7-1: Mono-THF ring Annonaceous Acetogenins (AA1-AA3) ·············· 199
SECTION 7-2: Non-Adjacent Bis-THF Annonaceous Acetogenins (AA4-AA10) · ·····217
SECTION 7-3: Adjacent Bis-THF rings Annonaceous Acetogenins (AA12, 16, and 17) ············································································235
SECTION 7-4: Cytotoxicity of Annonaceous Acetogenins ·······················255
SECTION 7-5: Physical and Spectral Data of Annonaceous Acetogenins ·········259
CHAPTER VIII LIGNANOIDS AND THE OTHER COMPOUNDS ··························· 265
SECTION 8-1: Squadinorlignoside (L1) ·······································269
SECTION 8-2: (6R,7S,8S)-1-Methoxyisolariciresinol-7a-O-b-D-glucoside (L2) · 275
SECTION 8-3: Physical and Spectral Data of Lignanoids and The Other Compounds ·············································································291
SUMMARY ····································································297
REFERENCES ·································································301
PUBLICATIONS ·······························································311
VITA ······································································ 315
APPENDIX ·································································· 317
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