臺灣博碩士論文加值系統

以抗癌、抗菌和殺福壽螺進行一系列台灣產天然物之活性篩選，發現無患子果實甲醇萃取物和五倍子(羅氏鹽膚木的蟲癭)乙醇萃取物皆具有有效的抗菌作用，無患子果實甲醇萃取物對害蟲殺福壽螺具有殺螺作用，而無患子蟲癭乙醇萃取物則具有抗血小板凝集作用與抗癌作用，因此分別進行無患子果實、蟲癭與五倍子其化學成分和生物活性成分之研究。
由無患子的果實中分離純化得到六個新化合物，三十五個為已知化合物。Oleanane-type saponins的化合物對福壽螺具有有效的防治作用，在濃度10 ppm下其致死率為70~90 %。除此之外，此類化合物也具有效的抗發炎作用。
無患子蟲癭分離純化得到二十二個新化合物和三十六個已知化合物。所分離之化合物進行抗血小板試之體外篩選生物活性研究，發現tirucallane-type saponins的新化合物不會引起血小板細胞毒性 (LDH leakage, <14.71 %, conc. 30 ?嵱) 之下，能夠有效地抑制platelet-activity factor (PAF), arachidonic acid (AA), thrombin (THB) 和U46619所誘導的血小板凝集反應；其中獲致的十個新dammarane type saponins的化合物，部份具有抗癌作用。
五倍子中分離純化得到二十一個為已知化合物，所分離之化合物目前正進行抗菌和抗發炎作用試驗。
由上述植物中共發現二十八個新化合物和九十二個已知化合物，其皆藉由一維、二維核磁共振光譜等物理數據和部份以化學方法確認其化學結構。

As a series of studies on the chemical constituents and biological activities (anti-canacer, anti-molluscoid, and anti-bacteria) of Taiwanese plants, the methanolic extracts of the fruits of Sapindus mukorossi and the EtOH extract of Galla Chinensis (the galls of Rhus chinensis) had antibacterial activity and the EtOH extract of the fruits of S. mukorssii showed the effect of causing death of Pomacea canaliculata (Lamarck), as well as the EtOH extract of the galls of S. mukorossi showed anti-platelet aggregation activity and cytotoxicity against several human tumor cell lines.
Investigation of the methanolic extract of fruits of S. mukorossi led to the isolation of six new saponins and thirty-five known compounds. The bioassay for preventive activity test against Pomacea canaliculata revealed that Oleanane-type saponins had 70~90 % inhibition at a concentration of 10 ppm. In addition, the oleanane-type saponins also show significant anti-inflammatory activity.
Twenty-two new compounds together with thirty-six known compounds were isolated from the galls of S. mukorossii. Biological evaluation showed that tirucallane-type saponins, had potent anti-platelet aggregation [induced by platelet-activity factor (PAF), arachidonic acid (AA), thrombin (THB) and U46619] and
no obvious cytotoxicity (measured by LDH leakage, <14.71 %, conc. 30 ?嵱).
Subsequent purification of Galla Chinensis yielded twenty-one known isolates including flavanoids, triterpenes, and tannins. The evaluation in anti-bacteria and anti-inflammatory activity for these isolates is still under progress.
The structural elucidation of these twenty-eight new and ninety-two known compounds are based on spectroscopic analyses (mainly 1D and 2D NMR techniques), as well as by chemical evidences.

目 錄
目 錄........................................................................................................ I

圖表目錄........................................................................................................ III

縮 寫 表........................................................................................................ XI

中文摘要…………………………………………………………………… XII
英文摘要…………………………………………………………………… XIII
第一章 緒言…………………………………………………………….…. 1
第一節 無患子之植物型態…………………………...……………... 1
第二節 五倍子之植物型態………………………………………….. 4
第二章 研究動機與目的………………………………………………….. 5
第一節 無患子部分………………………………………………….. 5
第二節 五倍子部分………………………………………………….. 8
第三章 藥理與化學成分研究回顧……………………………………….. 9
第一節 無患子研究回顧…………………………………………….. 9
第二節 五倍子研究回顧…………………………………………….. 13
第四章 萃取與分離………………………………………….……………. 16
第一節 無患子果殼成分之抽取與分離………………….…………. 16
第二節 無患子蟲癭成分之抽取與分離………………….…………. 22
第三節 五倍子成分之抽取與分離………………….………………. 27
第五章 化合物之結構證明………………….……………………………. 31
第一部份Dammarane-saponins化合物結構鑑定………………………… 32
第一節 Sapinmusaponin A (DS1)之構造證明…………………….. 34
第二節 Sapinmusaponins B (DS2)之構造證明…………………… 47
第三節 Sapinmusaponin C (DS3)之構造證明……………………. 56
第四節 Sapinmusaponin D (DS4)之構造證明……………………. 65
第五節 Sapinmusaponin E (DS5)之構造證明……………………. 74
第六節 Sapinmusaponin R (DS6)之構造證明……………………. 83
第七節 Sapinmusaponin S (DS7) 和sapinmusaponin SI (DS7I)之構造證明……………………………………………….…..
92
第八節 Sapinmusaponin O (DS 8)之構造證明…………………… 99
第九節 Sapinmusaponin P (DS9)之構造證明…………………….. 107
第十節 Sapinmusaponin Q (DS 10)之構造證明………………….. 115
第十一節 Sapinmusaponin U (DS 11)之構造證明………….………. 122
第十二節 Sapinmusaponin T (DS 12)之構造證明…………….…….. 130
第二部份Tirucallane-saponins化合物結構鑑定…………………...……... 139
第十三節 Sapinmusaponin F (TS1)之構造證明…………………….. 141
第十四節 Sapinmusaponin G (TS2)之構造證明……………...…….. 150
第十五節 Sapinmusaponin H (TS3)之構造證明……………………. 158
第十六節 Sapinmusaponin I (TS4) 之構造證明……………………. 164
第十七節 Sapinmusaponin J (TS5)之構造證明……………………... 171
第十八節 Sapinmusaponin V (TS6)之構造證明…………………….. 180
第十九節 Sapinmusaponin W (TS7)之構造證明………………….… 188
第二十節 Sapinmusaponin Q (TS8)之構造證明………………….…. 197
第二十一節 Sapinmusaponin Y (TS9)之構造證明………………….. 202
第二十二節 Sapinmusaponin Z (TS10)之構造證明………………… 210
第三部份 Oleanane-saponins化合物結構鑑定…………………………… 218
第二十三節 hederagenin 3-O-(2,4-O-di-acetyl-??-L-arabinopyrano- side)-(1→3)-??-L-rhamnopyranosyl-(1→2)-??-L-
arabinopyranoside (OS9) 之構造證明…………………

220
第二十四節 Sapinmusaponin K (OS10) 之構造證明………………. 229
第二十五節 Sapinmusaponin L (OS11) 之構造證明……………….. 236
第二十六節 Sapinmusaponin M (OS12) 之構造證明……………… 240
第二十七節 Sapinmusaponins N (OS13) 之構造證明……………... 248
第四部份Sesquiterpene glycoside化合物結構鑑定……………………… 255
第二十八節 Mukoroside I (SG) 之構造證明…………………….…. 255
第六章 藥理與生物活性篩選試驗…………………………………..……. 261
第一節 殺螺試驗 (Molluscicidal Activity) …………………………. 261
第二節 細胞毒殺試驗……………………………………………….. 265
第三節 抗血小板凝集活性試驗 (Antiplatelet aggregation activity).. 270
第四節 抗發炎試驗 (Anti-inflammatory activity) ………………..… 273
第五節 細菌及真菌之抑制試驗 (Antibacterial and antifungal activities) …………………………………………….……… 275
第七章 結 論………………………….……………………………..... 278
第八章 實驗部分…………………………………………………….…….. 284
第一節 實驗儀器與藥品………………………………….………….. 284
第二節 無患子果實成分之萃取與分離………………….…………. 286
第三節 無患子蟲癭成分之萃取與分離…………………………….. 288
第四節 五倍子成分之萃取與分離……………………………….…. 290
第五節 化學反應 291
第六節 藥理活性之實驗步驟…………………………….……….…. 292
第七節 各化合物的實驗數據………………………………….……. 300
第九章 參考文獻…………………………………………………….……. 323


















圖表目錄
Scheme 1. Isolation from the pericarps of Sapindus mukorossi………......... 18
Scheme 2. Isolation from the galls of Sapindus mukorossi………………… 24
Scheme 3. Isolation from the Galla chinensis…………………………......... 29
Scheme 4. Proposed biogenetic pathway of formation of dammarane-type saponins………………………... ………………………………
281
Scheme 5. Proposed biogenetic pathway of formation of tirucallane-type saponins,TS1-10………………………... ………………………
282
Scheme 6. Proposed biogenetic pathway of formation of oleanane-type saponins………………………... ……………………………….
283
圖之目錄
圖一、無患子乾燥果實圖片…………………... ………………………...... 3
圖二、無患子蟲癭圖片(一)………………………………………………... 3
圖三、無患子蟲癭圖片(二) …………………... ………………………..... 3
Fig. 1. Key TOCSY and HMBC correlations of DS1. …………….……….. 36
Fig. 2. Main NOESY correlations for DS1…………………………………. 36
Fig. 3. The FABMS Spectrum of Sapinmusaponin A (DS1) ………………. 38
Fig. 4. The IR Spectrum of Sapinmusaponin A (DS1) ……………….…….. 39
Fig. 5.The 1H-NMR Spectrum of Sapinmusaponin A (DS1) ……….……… 39
Fig. 6. The 13C-NMR Spectrum of Sapinmusaponin A (DS1) ……….…….. 40
Fig. 7. The DEPT Spectrum of Sapinmusaponin A (DS1) ………….……… 40
Fig. 8. The COSY Spectrum of Sapinmusaponin A (DS1) …………………
Fig. 9. The TOCSY Spectrum of Sapinmusaponin A (DS1) ………….……. 41
41
Fig. 10.The HMQC Spectrum of Sapinmusaponin A (DS1) …………...….. 42
Fig. 11.The HMBC Spectrum of Sapinmusaponins A (DS1) …………….... 42
Fig. 12. The NOESY Spectrum of Sapinmusaponins A (DS1) ………….…. 43
Fig. 13. The X-ray of Sapinmusaponins A (DS1) ………………………….. 43
Fig. 14. Key COSY and HMBC correlations of (DS2) ………………..…... 49
Fig. 15. Main NOESY correlations for DS2………………………….…….. 49
Fig. 16. The Mass Spectrum of Sapinmusaponin B (DS2) …………..…….. 50
Fig. 17. The IR Spectrum of Sapinmusaponin B (DS2) …………….……... 51
Fig. 18. The 1H-NMR Spectrum of Sapinmusaponin B (DS2) ……….….... 51
Fig. 19.The 13C-NMR Spectrum of Sapinmusaponin B (DS2) ……….….... 52
Fig. 20.The DEPT Spectrum of Sapinmusaponin B (DS2) ……………..…. 52
Fig. 21.The HMQC Spectrum of Sapinmusaponin B (DS2) …………….... 53
Fig. 22.The COSY Spectrum of Sapinmusaponin B (DS2) ……………..… 53
Fig. 23.The TOCSY Spectrum of Sapinmusaponin B (DS2) …………..….. 54
Fig. 24.The HMBC Spectrum of Sapinmusaponin B (DS2) …………..…... 54
Fig. 25.The NOESY Spectrum of Sapinmusaponin B (DS2) ……………… 55
Fig. 26. Key COSY and HMBC correlations of (DS3) ………………..…... 58
Fig. 27. Main NOESY correlations for(DS3) …………………………..….. 58
Fig. 28. The FABMS Spectrum of Sapinmusaponin C (DS3)……………… 59
Fig. 29. The IR Spectrum of Sapinmusaponin C (DS3) ………………...…. 60
Fig. 30. The 1H-NMR Spectrum of Sapinmusaponin C (DS3) ……………. 60
Fig. 31. The 1H-NMR Spectrum of Sapinmusaponin C (DS3) ……………. 61
Fig. 32. The 13C-NMR Spectrum of Sapinmusaponin C (DS3) …….….….. 61
Fig. 33. The DEPT Spectrum of Sapinmusaponin C (DS3) ……………..… 62
Fig. 34. The HMQC Spectrum of Sapinmusaponin C (DS3) …………….... 62
Fig. 35. The COSY Spectrum of Sapinmusaponin C (DS3) ……………..... 63
Fig. 36. The HMBC Spectrum of Sapinmusaponin C (DS3) …………...….. 63
Fig. 37. The NOESY Spectrum of Sapinmusaponin C (DS3) …………...… 64
Fig. 38. The 1H-NMR and TOCSY of partial DS3 and DS4 .. …………..… 67
Fig. 39. The 13C-NMR of partial DS3 and DS4. .. ……………………….... 67
Fig. 40. Key COSY and HMBC correlations of DS4.. …………………..… 67
Fig. 41. The FABMS Spectrum of Sapinmusaponin D (DS4) .. ………..…. 69
Fig. 42. The IR Spectrum of Sapinmusaponin D (DS4) .. ……………...….. 69
Fig. 43. The 1H-NMR Spectrum of Sapinmusaponins D (DS4)..……….…. 70
Fig. 44. The 13C-NMR Spectrum of Sapinmusaponins D (DS4)..………….. 70
Fig. 45. The DEPT Spectrum of Sapinmusaponins D (DS4)..……………... 71
Fig. 46. The HMQC Spectrum of Sapinmusaponins D (DS4) ..…………… 71
Fig. 47. The HMBC Spectrum of Sapinmusaponins D (DS4) ..……………. 72
Fig. 48. The COSY Spectrum of Sapinmusaponins D (DS4) ..…………….. 72
Fig. 49. The TOCSY Spectrum of Sapinmusaponins D (DS4) .. …………... 73
Fig. 50. The NOESY Spectrum of Sapinmusaponins D (DS4) .. …………. 73
Fig. 51. The 1H-NMR of partial DS4 and DS5.. ………………………….... 76
Fig. 52. The 13C-NMR of partial DS4 and DS5.. …………………………... 76
Fig. 53. Key TOCSY and HMBC correlations of DS5.. ………………….... 76
Fig. 54. The 13C-NMR of partial dammaraenediol I and dammaraenediol II. 76
Fig. 55. The FABMS Spectrum of Sapinmusaponin E (DS5) .. …………. 78
Fig. 56. The IR Spectrum of Sapinmusaponin E (DS5) .. ………………….. 78
Fig. 57. The 1H-NMR Spectrum of Sapinmusaponin E (DS5) .. …………... 79
Fig. 58. The 13C-NMR Spectrum of Sapinmusaponin E (DS5) .. ………….. 79
Fig. 59. The DEPT Spectrum of Sapinmusaponin E (DS5) .. ……………… 80
Fig. 60. The HMQC Spectrum of Sapinmusaponin E (DS5) .. ……….……. 80
Fig. 91. The HMBC Spectrum of Sapinmusaponin E (DS5) .. ………..….... 81
Fig. 62. The TOCSY Spectrum of Sapinmusaponin E (DS5) .. ………..…... 81
Fig. 63. The NOESY Spectrum of Sapinmusaponin E (DS5) .. ………….... 82
Fig. 64. Key TOCSY and HMBC correlations of DS6.. ………………..….. 85
Fig. 65. Main NOESY correlations for DS6.. …………………………….... 85
Fig. 66. The 13C-NMR of partial dammaraenediol I, II, DS5 and DS6…….. 85
Fig. 67. The FABMS Spectrum of Sapinmusaponins R (DS6) …………..... 87
Fig. 68. The IR Spectrum of Sapinmusaponins R (DS6) …………………... 87
Fig. 69. The 1H-NMR Spectrum of Sapinmusaponins R (DS6) ………….... 88
Fig. 70. The 13C-NMR Spectrum of Sapinmusaponins R (DS6) ………..…. 88
Fig. 71. The DEPT Spectrum of Sapinmusaponins R (DS6) ………………. 89
Fig. 72. The HMQC Spectrum of Sapinmusaponins R (DS6) …………..…. 89
Fig. 73. The HMBC Spectrum of Sapinmusaponins R (DS6) …………..…. 90
Fig. 74. The NOESY Spectrum of Sapinmusaponins R (DS6) …………..... 90
Fig. 75. The COSY Spectrum of Sapinmusaponins R (DS6) …………….... 91
Fig. 76. The TOCSY Spectrum of Sapinmusaponins R (DS6) …………….. 91
Fig. 77. Key COSY and HMBC correlations of DS7 …………………….... 94
Fig. 78. The 1H-NMR of partial DS7 and DS7A. ………………………….. 94
Fig. 79. The 13C-NMR of partial DS7 and DS7A. ……………………...….. 94
Fig. 80. The 1H-NMR Spectrum of Sapinmusaponin S (DS7&7A) ….......... 95
Fig. 81. The 13C-NMR Spectrum of Sapinmusaponin S (DS7&7A) ………. 96
Fig. 82. The DEPT Spectrum of Sapinmusaponin S (DS7&7A) …………... 96
Fig. 83. The HMQC Spectrum of Sapinmusaponin S (DS7&7A) …………. 97
Fig. 84. The HMBC Spectrum of Sapinmusaponin S (DS7&7A) …………. 97
Fig. 85. The COSY Spectrum of Sapinmusaponin S (DS7&7A) ………….. 98
Fig. 86. Key COSY and HMBC correlations of DS8 …………………….... 100
Fig. 87. The FABMS Spectrum of Sapinmusaponin O (DS8) ……………... 102
Fig. 88. The IR Spectrum of Sapinmusaponin O (DS8) ………………….... 102
Fig. 89. The 1H-NMR Spectrum of Sapinmusaponin O (DS8) ………......... 103
Fig. 90. The 13C-NMR Spectrum of Sapinmusaponin O (DS8) ………….... 103
Fig. 91. The DEPT Spectrum of Sapinmusaponins O (DS8) ………………. 104
Fig. 92. The HMQC Spectrum of Sapinmusaponin O (DS8) ……………… 104
Fig. 93. The HMBC Spectrum of Sapinmusaponin O (DS8) ……………… 105
Fig. 94. The COSY Spectrum of Sapinmusaponin O (DS8) ……………….. 105
Fig. 95. The NOESY Spectrum of Sapinmusaponin O (DS8) …………...… 106
Fig. 96. The 1H- and 13C-NMR of partial DS8 and DS9………………….... 109
Fig. 97. Key COSY and HMBC correlations of DS9 ………………….…... 109
Fig. 98. The FABMS Spectrum of Sapinmusaponin P (DS9) ………….…... 110
Fig. 99. The IR Spectrum of Sapinmusaponin P (DS9) ………………….... 110
Fig. 100. The 1H-NMR Spectrum of Sapinmusaponin P (9) ……………... 111
Fig. 101. The 13C-NMR Spectrum of Sapinmusaponin P (DS9) ………..... 111
Fig. 102. The DEPT Spectrum of Sapinmusaponins P (DS9) ……………... 112
Fig. 103. The HMQC Spectrum of Sapinmusaponin P (DS9) ……………... 112
Fig. 104. The HMBC Spectrum of Sapinmusaponin P (DS9) ……………... 113
Fig. 105. The COSY Spectrum of Sapinmusaponin P (DS9) ……………… 113
Fig. 106. The NOESY Spectrum of Sapinmusaponin P (DS9) …………….. 114
Fig. 107. Key COSY and HMBC correlations of DS10………………......... 117
Fig. 108. The FABMS Spectrum of Sapinmusaponin Q (DS10) ………….. 117
Fig. 109. The IR Spectrum of Sapinmusaponin Q (DS10) ………………… 118
Fig. 110. The 1H-NMR Spectrum of Sapinmusaponin Q (DS10) …………. 118
Fig. 111. The 13C-NMR Spectrum of Sapinmusaponin Q (DS10) ………… 119
Fig. 112. The DEPT Spectrum of Sapinmusaponin Q (DS10) ……….......... 119
Fig. 113. The HMQC Spectrum of Sapinmusaponin Q (DS10) ………….... 120
Fig. 114. The COSY Spectrum of Sapinmusaponin Q (DS10) ………......... 120
Fig. 115. The HMBC Spectrum of Sapinmusaponin Q (DS10) …………… 121
Fig. 116. The NOESY Spectrum of Sapinmusaponin Q (DS10) …………... 121
Fig. 117. The FABMS Spectrum of Sapinmusaponin U (DS11) …………... 124
Fig. 118. The IR Spectrum of Sapinmusaponin U (DS11) ………………… 125
Fig. 119. The 1H-NMR Spectrum of Sapinmusaponin U (DS11) …….......... 125
Fig. 120. The 13C-NMR Spectrum of Sapinmusaponin U (DS11) ………… 126
Fig. 121. The DEPT Spectrum of Sapinmusaponin U (DS11) …………….. 126
Fig. 122. The HMQC Spectrum of Sapinmusaponin U (DS11) ………….... 127
Fig. 123. The COSY Spectrum of Sapinmusaponin U (DS11) …………...... 127
Fig. 124. The TCOSY Spectrum of Sapinmusaponin U (DS11) …………... 128
Fig. 125. The HMBC Spectrum of Sapinmusaponin U (DS11) ………......... 128
Fig. 126. The NOESY Spectrum of Sapinmusaponin U (DS11) ……........... 129
Fig. 127. Key COSY and HMBC correlations of DS12………………......... 132
Fig. 128. The 13C-NMR of partial Yesanchinosides and DS12. ………......... 132
Fig. 129. The FABMS Spectrum of Sapinmusaponin T (DS12) …………... 133
Fig. 130. The IR Spectrum of Sapinmusaponin T (DS12) …………………. 134
Fig. 131. The 1H-NMR Spectrum of Sapinmusaponin T (DS12) …….......... 134
Fig. 132. The 13C-NMR Spectrum of Sapinmusaponin T (DS12) …………. 135
Fig. 133. The 13C-NMR Spectrum of Sapinmusaponin T (DS12) …………. 135
Fig. 134. The DEPT Spectrum of Sapinmusaponins T (DS12) ……………. 136
Fig. 135. The HMQC Spectrum of Sapinmusaponin T (DS12) ……………. 136
Fig. 136. The COSY Spectrum of Sapinmusaponin T (DS12) ……….......... 137
Fig. 137. The TCOSY Spectrum of Sapinmusaponin T (DS12) ………….... 137
Fig. 138. The HMBC Spectrum of Sapinmusaponin T (DS12) ……………. 138
Fig. 139. The NOESY Spectrum of Sapinmusaponin T (DS12) …………... 138
Fig. 140. 13C-NMR data of 3-epi-flindissol………………………………… 140
Fig. 141. 13C-NMR data of 21-??-acetoxy-melianone and
21-??-acetoxy-melianone………………………………………….
140
Fig. 142. Key TOCSY and HMBC correlations of TS1. …………………... 143
Fig. 143. Main NOESY correlations for TS1. ……………………………... 143
Fig. 144. The FABMS Spectrum of Sapinmusaponin F (TS1) …………….. 145
Fig. 145. The IR Spectrum of Sapinmusaponin F (TS1) …………………... 146
Fig. 146. The 1H-NMR Spectrum of Sapinmusaponin F (TS1) …………… 146
Fig. 147. The 13C-NMR and DEPT Spectrum of Sapinmusaponin F (TS1).. 147
Fig. 148. The HMQC Spectrum of Sapinmusaponin F (TS1) …………....... 147
Fig. 149. The HMBC Spectrum of Sapinmusaponin F (TS1) ……………... 148
Fig. 150. The TCOSY Spectrum of Sapinmusaponin F (TS1) …………….. 148
Fig. 151. The NOCSY Spectrum of Sapinmusaponin F (TS1) …………….. 149
Fig. 152. Key TOCSY and HMBC correlations of TS2. …………………... 152
Fig. 153. Main NOESY correlations for TS2. ……………………………... 152
Fig. 154. The FABMS Spectrum of Sapinmusaponin G (TS2) ……. …....... 153
Fig. 155. The IR Spectrum of Sapinmusaponin G (TS2) ……. …………… 154
Fig. 156. The 1H-NMR Spectrum of Sapinmusaponin G (TS2) ……. …….. 154
Fig. 157. The 13C-NMR Spectrum of Sapinmusaponin G (TS2) ……. ……. 155
Fig. 158. The HMQC Spectrum of Sapinmusaponin G (TS2) …………….. 155
Fig. 159. The HMBC Spectrum of Sapinmusaponin G (TS2) …………….. 156
Fig. 160. The COSY Spectrum of Sapinmusaponin G (TS2) ……. ……….. 156
Fig. 161. The NOCSY Spectrum of Sapinmusaponin G (TS2) . …………... 157
Fig. 162. Key COSY and HMBC correlations of TS3. . …………………... 159
Fig. 163. The FABMS Spectrum of Sapinmusaponin H (TS3) . ………....... 160
Fig. 164. The IR Spectrum of Sapinmusaponin H (TS3) . ………………… 160
Fig. 165. The 1H-NMR Spectrum of Sapinmusaponin H (TS3) . ………….. 161
Fig. 166. The 13C-NMR Spectrum of Sapinmusaponin H (TS3) . …………. 161
Fig. 167. The HMQC Spectrum of Sapinmusaponin H (TS3) . …………… 162
Fig. 168. The COSY Spectrum of Sapinmusaponin H (TS3) . …………….. 162
Fig. 169. The HMBC Spectrum of Sapinmusaponin H (TS3) . ……………. 163
Fig. 170. The NOESY Spectrum of Sapinmusaponin H (TS3) . ………....... 163
Fig. 171. Key COSY and HMBC correlations of TS4. . …………………... 165
Fig. 172. The FABMS Spectrum of Sapinmusaponin I (TS4) . ……………. 166
Fig. 173. The IR Spectrum of Sapinmusaponin I (TS4) . ………………….. 167
Fig. 174. The 1H-NMR Spectrum of Sapinmusaponin I (TS4) . ………....... 167
Fig. 175. The 13C-NMR Spectrum of Sapinmusaponin I (TS4) . ………….. 168
Fig. 176. The DEPT Spectrum of Sapinmusaponin I (TS4) . ……………… 168
Fig. 177. The HMQC Spectrum of Sapinmusaponin I (TS4) . …………….. 169
Fig. 178. The HMBC Spectrum of Sapinmusaponin I (TS4) ) . …………… 169
Fig. 179. The COSY Spectrum of Sapinmusaponin I (TS4) ) . ……………. 170
Fig. 180. The NOESY Spectrum of Sapinmusaponin I (TS4) ) . ………….. 170
Fig. 181. Key 13C- and 1H-NMR data of the aglycon of TS5. …………....... 173
Fig. 182. Main NOESY correlations for TS5. . …………. ………………... 173
Fig. 183. Key COSY and HMBC correlations of TS5. …. ………………... 173
Fig. 184. The FABMS Spectrum of Sapinmusaponin J (TS5) …. ………… 175
Fig. 185. The IR Spectrum of Sapinmusaponin J (TS5) …. ……………….. 175
Fig. 186. The 1H-NMR Spectrum of Sapinmusaponin J (TS5) ……………. 176
Fig. 187. The 13C-NMR Spectrum of Sapinmusaponin J (TS5) …………… 176
Fig. 188. The DEPT Spectrum of Sapinmusaponin J (TS5) ……………….. 177
Fig. 189. The HMQC Spectrum of Sapinmusaponin J (TS5) ……………… 177
Fig. 190. The HMBC Spectrum of Sapinmusaponin J (TS5) ……………… 178
Fig. 191. The COSY Spectrum of Sapinmusaponin J (TS5) ………………. 178
Fig. 192. The NOESY Spectrum of Sapinmusaponin J (TS5) …………….. 179
Fig. 193. The FABMS Spectrum of Sapinmusaponin V (TS6) ……………. 183
Fig. 194. The IR Spectrum of Sapinmusaponin V (TS6) ………………….. 183
Fig. 195. The 1H-NMR Spectrum of Sapinmusaponin V (TS6) …………… 184
Fig. 196. The 13C-NMR Spectrum of Sapinmusaponin V (TS6) …………... 184
Fig. 197. The DEPT Spectrum of Sapinmusaponin V (TS6) ………………. 185
Fig. 198. The HMQC Spectrum of Sapinmusaponin V (TS6) …………….. 185
Fig. 199. The HMBC Spectrum of Sapinmusaponin V (TS6) …………….. 186
Fig. 200. The COSY Spectrum of Sapinmusaponin V (TS6) ……………… 186
Fig. 201. The NOESY Spectrum of Sapinmusaponin V (TS6) ……………. 187
Fig. 202. Key COSY, TOCSY and HMBC correlations of TS7……………. 190
Fig. 203. The FABMS Spectrum of Sapinmusaponin W (TS7) …………… 192
Fig. 204. The IR Spectrum of Sapinmusaponin W (TS7) ………………….. 192
Fig. 205. The 1H-NMR Spectrum of Sapinmusaponin W (TS7) ………....... 193
Fig. 206. The 13C-NMR Spectrum of Sapinmusaponin W (TS7) ………… 193
Fig. 207. The DEPT Spectrum of Sapinmusaponin W (TS7) ……………… 194
Fig. 208. The HMQC Spectrum of Sapinmusaponin W (TS7) ………......... 194
Fig. 209. The HMQC Spectrum of Sapinmusaponin W (TS7) …………….. 195
Fig. 210. The COSY Spectrum of Sapinmusaponin W (TS7) ……………... 195
Fig. 211. The TOCSY Spectrum of Sapinmusaponin W (TS7) ……………. 196
Fig. 212. The NOESY Spectrum of Sapinmusaponin W (TS7) ………….... 196
Fig. 213. The FABMS Spectrum of Sapinmusaponin Q (TS8) ……………. 199
Fig. 214. The IR Spectrum of Sapinmusaponin Q (TS8) ………………….. 199
Fig. 215. The 1H-NMR Spectrum of Sapinmusaponin Q (TS8) …………… 200
Fig. 216. The 13C--NMR Spectrum of Sapinmusaponin Q (TS8) …………. 200
Fig. 217. The COSY of Sapinmusaponin Q (TS8) ………………………… 201
Fig. 218. The NOESY Spectrum of Sapinmusaponin Q (TS8)…………….. 201
Fig. 219. Key 13C- and 1H-NMR data of the aglycon of TS9 and TS6. …… 204
Fig. 220. Main NOESY correlations for TS9. ……………………………... 204
Fig. 221. The FABMS Spectrum of Sapinmusaponin Y (TS9) ……………. 205
Fig. 222. The IR Spectrum of Sapinmusaponin Y (TS9) ………………....... 206
Fig. 223. The 1H-NMR Spectrum of Sapinmusaponin Y (TS9) …………… 206
Fig. 224. The 13C and DEPT Spectrum of Sapinmusaponin Y (TS9) ……… 207
Fig. 225. The HMQC Spectrum of Sapinmusaponin Y (TS9) …………....... 207
Fig. 226. The HMBC Spectrum of Sapinmusaponin Y (TS9) …………....... 208
Fig. 227. The COSY Spectrum of Sapinmusaponin Y (TS9) ……………… 208
Fig. 228. The TOCSY Spectrum of Sapinmusaponin Y (TS9) …………….. 209
Fig. 229. The NOESY Spectrum of Sapinmusaponin Y (TS9) ……………. 209
Fig. 230. The FABMS Spectrum of Sapinmusaponin Z (TS10) …………... 213
Fig. 231. The IR Spectrum of Sapinmusaponin Z (TS10) ……………......... 213
Fig. 232. The 1H-NMR Spectrum of Sapinmusaponin Z (TS10) ………….. 214
Fig. 233. The 13C -NMR Spectrum of Sapinmusaponin Z (TS10) ………… 214
Fig. 234. The DEPT Spectrum of Sapinmusaponin Z (TS10) ……………... 215
Fig. 235. The HMQC Spectrum of Sapinmusaponin Z (TS10) ………......... 215
Fig. 236. The HMBC Spectrum of Sapinmusaponin Z (TS10) ………......... 216
Fig. 237. The COSY Spectrum of Sapinmusaponin Z (TS10) …………….. 216
Fig. 238. The NOESY Spectrum of Sapinmusaponin Z (TS10) …………… 217
Fig. 239. Key TOCSY and HMBC correlations of OS9……………………. 222
Fig. 240. Key TOCSY and HMBC correlations of OS9……………………. 222
Fig. 241. The FABMS Spectrum of Compound (OS9) ……………………. 224
Fig. 242. The IR Spectrum of Compound (OS9) …………………………... 224
Fig. 243. The 1H-NMR Spectrum of Compound (OS9) ………………........ 225
Fig. 244. The 13C-NMR Spectrum of Compound (OS9) …………………... 225
Fig. 245. The DEPT Spectrum of Compound (OS9) ………………………. 226
Fig. 246. The HMQC Spectrum of Compound (OS9) ……………………... 226
Fig. 247. The HMBC Spectrum of Compound (OS9) ……………………... 227
Fig. 248. The NOESY Spectrum of Compound (OS9) ……………………. 227
Fig. 249. The COSY Spectrum of Compound (OS9) ……………………… 228
Fig. 250. The TOCSY Spectrum of Compound (OS9) ………………......... 228
Fig. 251. Key COSY and HMBC correlations of OS10. …………………... 230
Fig. 252. The Mass Spectrum of Sapinmusaponin K (OS10) ……………... 231
Fig. 253. The IR Spectrum of Sapinmusaponin K (OS10) ………………… 232
Fig. 254. The 1H-NMR Spectrum of Sapinmusaponin K (OS10) ……......... 232
Fig. 255. The 13C-NMR Spectrum of Sapinmusaponin K (OS10) ………… 233
Fig. 256. The DEPT Spectrum of Sapinmusaponin K (OS10) ………......... 233
Fig. 257. The HMQC Spectrum of Sapinmusaponin K (OS10) …………… 234
Fig. 258. The HMBC Spectrum of Sapinmusaponin K (OS10) …………… 234
Fig. 259. The COSY Spectrum of Sapinmusaponin K (OS10) ………......... 235
Fig. 260. 13C-NMR data for OS11. ………………….................................... 237
Fig. 261. The MALDI-TOF MS Spectrum of Sapinmusaponin K (OS11)… 238
Fig. 262. The IR Spectrum of Sapinmusaponin K (OS11) ………………… 238
Fig. 263. The 1H-NMR Spectrum of Sapinmusaponin K (OS11) ……......... 239
Fig. 264. The 13C-NMR Spectrum of Sapinmusaponin K (OS11) ………… 239
Fig. 265. Key COSY and HMBC correlations of OS12. …………………... 241
Fig. 266. The Mass Spectrum of Sapinmusaponin M (OS12) ……………... 242
Fig. 267. The IR Spectrum of Sapinmusaponin M (OS12) ………………... 243
Fig. 268. The 1H-NMR Spectrum of Sapinmusaponin M (OS12) …………. 243
Fig. 269. The 13C-NMR Spectrum of Sapinmusaponin M (OS12) ………... 244
Fig. 270. The DEPT Spectrum of Sapinmusaponin M (OS12) ……………. 244
Fig. 271. The HMQC Spectrum of Sapinmusaponin M (OS12) …………... 245
Fig. 272. The HMBC Spectrum of Sapinmusaponin M (OS12) …………... 245
Fig. 273. The COSY Spectrum of Sapinmusaponin M (OS12) …………… 246
Fig. 274. The TOCSY Spectrum of Sapinmusaponin M (OS12) ………….. 246
Fig. 275. The NOESY Spectrum of Sapinmusaponin M (OS12) ………….. 247
Fig. 276. Key TOCSY and HMBC correlations of OS13………………….. 249
Fig. 277. The Mass Spectrum of Sapinmusaponin N (OS13) ……………... 250
Fig. 278. The IR Spectrum of Sapinmusaponin N (OS13) …………............ 251
Fig. 279. The 1H-NMR Spectrum of Sapinmusaponin N (OS13) ……......... 251
Fig. 280. The 13C-NMR Spectrum of Sapinmusaponin N (OS13) ………… 252
Fig. 281. The DEPT Spectrum of Sapinmusaponin N (OS13) ……….......... 252
Fig. 282. The HMQC Spectrum of Sapinmusaponin N (OS13) …………… 253
Fig. 283. The HMBC Spectrum of Sapinmusaponin N (OS13) …………… 253
Fig. 284. The TOCSY Spectrum of Sapinmusaponin N (OS13) …………... 254
Fig. 285. The NOESY Spectrum of Sapinmusaponin N (OS13) …………... 254
Fig. 286. Key COSY and HMBC correlations of SG…………..................... 257
Fig. 287. The IR Spectrum of mukoroside I (SG) …………......................... 257
Fig. 288. The 1H-NMR Spectrum of mukoroside I (SG) ………………... 258
Fig. 289. The 13C-NMR Spectrum of mukoroside I (SG) …………... …… 258
Fig. 290. The DEPT Spectrum of mukoroside I (SG) …………………..… 259
Fig. 291. The HMQC Spectrum of mukoroside I (SG) ……………….…… 259
Fig. 292. The COSY Spectrum of mukoroside I (SG) …………... ……… 260
Fig. 293. The HMBC Spectrum of mukoroside I (SG) …………... ……… 260
Fig. 294. Structure of saponins for molluscicidal activity………………….. 262
Fig. 295 Effects of saponins on the DNA relaxation activity by DNA topoisomerase…………………………………………………...
268
Fig. 296. The cytotoxic of saponins by LDH test. …………………………. 272
Fig. 297. The summary signaling pathways of OS16 inhibit superoxide generation and release in human neutrophils………………………………..
274
表之目錄
Table 1. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS1……………………..
35
Table 2. 13C (100 MHz) and 1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of DS1………………………..
36
Table 3. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS2..................................
48
Table 4. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS3……………………..
57
Table 5. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS4……………………..
66
Table 6. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS5……………………..
75
Table 7. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS6……………………..
84
Table 8. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS7/epi-DS7……………
93
Table 9. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS8……………………..
100
Table 10. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS9……………………..
108
Table 11. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS10……………………
116
Table 12. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS11……………………
123
Table 13. 13C (100 MHz), 1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of DS12……………………
131
Table 14. 13C (125 MHz)、1H (500 MHz) NMR data and 2D NMR correlations for the aglycon moieties of TS1……………………..
142
Table 15. 13C, 1H NMR data and 2D NMR correlations for the sugar moieties of TS1……………………………………………………
143
Table 16. 13C (125 MHz)、1H (500 MHz) NMR data and 2D NMR correlations for the aglycon moieties of TS2……………………
151
Table 17. 13C (125 MHz)、1H (500 MHz) NMR data and 2D NMR correlations for the aglycon moieties of TS3……………………

159
Table 18. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of TS4……………………….
165
Table 19. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon of TS5……………………………….
172
Table 20. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of TS5………………………..
174
Table 21. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of TS6……………………..
181
Table 22. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of TS6………………………..
182
Table 23. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of TS7……………………..
189
Table 242. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of TS7………………………..
190
Table 25. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for TS8……………………………………………..
198
Table 26. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon of TS9……………………………….
203
Table 27. 13C and 1H NMR data and 2D NMR correlations for the sugar moieties of TS9……………………………………………………
204
Table 28. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations of the aglycon for TS10……………………………...
211
Table 29. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the sugar moieties of TS10………………………
212
Table 30. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations for the aglycon moieties of OS9……………………
221
Table 31. 13C- (100 MHz) and 1H- (400 MHz) NMR Data (??) of the aglycon moiety of OS9 -13……………………………………….
221
Table 32. 13C (125 MHz), 1H NMR (500 MHz) data and 2D NMR correlations for the sugar moieties of OS10………………………
230
Table 33. 13C (100 MHz), 1H NMR (400 MHz) data and 2D NMR correlations for the sugar moieties of OS11………………………
237
Table 34. 13C (100 MHz), 1H NMR (400 MHz) data and 2D NMR correlations for the sugar moieties of OS12………………………
241
Table 35. 13C (100 MHz), 1H NMR (400 MHz) data and 2D NMR correlations for the sugar moieties of OS13………………………
249
Table 36. 13C (100 MHz)、1H (400 MHz) NMR data and 2D NMR correlations of SG…………………………………………………
256
Table 37. Molluscicidal activity of the extracts of the pericarps of Sapindus mukorossi and nicolosamide against the Pomacea canaliculata by submersion method. …………………………………………

263
Table 38. The toxicity of the fish for S. mukorossi and Camellia oleifera… 263
Table 39. Molluscicidal activity of the extracts of the pericarps of S. mukorossi, metaldehyde and nicolosamide against P. canaliculata in paddy field after 72 hrs treatment. ………………

263
Table 40. Molluscicidal activity of the fraction against young P. canaliculata by submersing method…………………………….
264
Table 41. Molluscicidal activity of saponins against young P. canaliculata by submersing method……………………………………………
264
Table 42. Cytotoxic acticity data of saponins………………………………. 267
Table 43. Relative Ratio of EBV-EA Activation with Respect to the Positive Control TPA (100%) in the Presence of saponins…..…... 269
Table 44.　IC50 Values of saponins on the aggregation of washed rabbit platelets induced by PAF, U46619, THB or AA. ……………..... 272
Table 45. Inhibitory effects of saponins isolated from Sapindus mukorossi on superoxide anion generation in human neutrophils responsive to fMLP/CB………………………………………………………. 274
Table 46. Antibacterial activity of the MeOH extracts from S. mukorossi… 276
Table 47. Antifungal activity of the MeOH extracts (100 ppm) from S. mukorossi………………………………………………………… 276
Table 48. Antibacterial activity (Bacillus cereus) o f compounds………….. 277
Table 49. Antibacterial activity (E. coli DH5α) of compounds…………….. 277
附錄………………………………………………………………………… 314

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