臺灣博碩士論文加值系統

薄葉山礬(Symplocos anomala Brand)隸屬於灰木科(Symplocaceae)，是一種
小喬木。分布於日本沖繩、東南亞、中國南部和台灣1。灰木屬為灰木科中唯一
的屬，曾於該屬中發現的化合物包含以下種類：saponins、triterpenoids、flavonoids、
lignans、phenols、alkaloids、sterols 和iridoids。於約1400 多種的台灣產之植物
針對抗結核分枝桿菌(Mycobacterium tuberculosis H37Rv)活性篩選中，薄葉山礬
葉部的甲醇萃取物有良好的抗結核活性，本植物未曾有過化學成分分離或生物活
性之研究，故本研究之目的為進行薄葉山礬葉部的化學成分分離以及生物活性之
探討。
經由活性導向分劃，由薄葉山礬葉部之乙酸乙酯可溶層中，分離出30 個已
知的化合物，其中包含：三個alkaloids：vincoside lactam (116)、naucleaorine (117)
和1,2,3,4-tetrahydro-1-oxo-β-carboline (134)，四個apocarotenoids：tectoionol A
(118)、linarionoside B (119)、blumenol B (120)和(+)-3-oxo-α-ionone (121)，兩個
triterpenoids ： asiatic acid (3) 和jacoumaric acid (122) ，一個iridoid ： 4-epialyxialactone
(123) ，兩個benzenoids：syringaldehyde (124)和salidroside (125) ，
兩個phenylpropanoids：trans-ferulic acid (126)和trans-methyl ferulate (127) ，一
個coumarin： isoscopoletin (128) ，六個lignans：(+)-sesamin (129)、(±)-pinoresinol
(84)、(±)-syringaresinol (130)、(+)-1-acetoxypinoresinol 4''-O-methyl ether (131)、
(+)-lariciresinol (132)和(＋)-lariciresinol 9-O-β-D-glucopyranoside (133) ，兩個
chlorophylls：pheophytin-a (135)和151-hydroxypurpurin-7-lactone dimethyl ester
(136) ，三個 steroids：β-sitosterol (109) and stigmasterol (111)之混合物以及
α-spinasterol (137)，四個fatty acid 及derivatives：(11S,12S,13S)-(9Z,15Z)-11-
hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid (138)、methyl palmitate (139) and
methyl oleate (140)之混合物和(Z)-3-hexenyl-β-D-glucopyranoside (141)。

Symplocos anomala Brand (Symplocaceae) is a small tree. It distributes at
Okinawa, Southeast Asia, Southern China, and Taiwan. Saponins, triterpenoids,
flavonoids, lignans, phenols, alkaloids, sterols, and iridoids are widely occurred in
Symplocos, which is the only genus in Symplocaceae. Approximately about 1,400
species of Formosan plants have been screened for anti-tubercular activity against
Mycobacterium tuberculosis H37Rv in vitro. The methanolic extract of the leaves of
this plant showed significant anti-tubercular activity in vitro. The chemical
constituents and their bioactivities of this species have never been conducted.
Bioassay-guided fractionation of active ethyl acetate-soluble layer from the
leaves of this species led to the isolation of 30 known compounds, including three
alkaloids: vincoside lactam (116), naucleaorine (117), and 1,2,3,4-tetrahydro-1-oxo-β-
carboline (134), four apocarotenoids: tectoionol A (118), linarionoside B (119),
blumenol B (120), and (+)-3-oxo-α-ionone (121), two triterpenoids: asiatic acid (3) and
jacoumaric acid (122), one iridoid: 4-epi-alyxialactone (123), two benzenoids:
syringaldehyde (124) and salidroside (125), two phenylpropanoids: trans-ferulic acid
(126) and trans-methyl ferulate (127), one coumarin: isoscopoletin (128), five lignans:
(+)-sesamin (129), (±)-pinoresinol (84), (±)-syringaresinol (130), (+)-1-acetoxypinoresinol
4''-O-methyl ether (131), (+)-lariciresinol (132), and (＋)-lariciresinol 9-O-β-
D-glucopyranoside (133), two chlorophylls: pheophytin-a (135) and 151-hydroxypurpurin-
7-lactone dimethyl ester (136), three steroids: a mixture of β-sitosterol (109)
and stigmasterol (111), α-spinasterol (137), four fatty acid and derivatives:
(11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid (138), a
mixture of methyl palmitate (139) and methyl oleate (140) and (Z)-3-hexenyl-β-Dglucopyranoside
(141).

目錄.................................................................................................................................I
圖目錄..........................................................................................................................IV
表目錄.......................................................................................................................XIII
中文摘要...................................................................................................................XIV
英文摘要....................................................................................................................XV
Glossary of Abbreviations ........................................................................................ XVI
第一章、序言..................................................................................................................1
第二章、研究動機與目的............................................................................................4
第三章、灰木屬過去文獻回顧....................................................................................5
第四章、萃取與分離..................................................................................................21
第五章、化合物之結構鑑定......................................................................................25
第一節、vincoside lactam (116) 之結構鑑定.......................................................25
第二節、naucleaorine (117) 之結構鑑定..............................................................35
第三節、tectoionol A (118) 之結構鑑定...............................................................42
第四節、linarionoside B (119) 之結構鑑定..........................................................48
第五節、blumenol B (120) 之結構鑑定...............................................................54
第六節、(+)-3-oxo-α-ionone (121) 之結構鑑定....................................................60
第七節、asiatic acid (3) 之結構鑑定....................................................................66
第八節、jacoumaric acid (122) 之結構鑑定........................................................69
第九節、4-epi-alyxialactone (123) 之結構鑑定...................................................72
第十節、syringaldehyde (124) 之結構鑑定...........................................................78
第十一節、salidroside (125) 之結構鑑定..............................................................81
第十二節、trans-ferulic acid (126) 之結構鑑定....................................................87
第十三節、trans-methyl ferulate (127) 之結構鑑定..............................................90
第十四節、isoscopoletin (128) 之結構鑑定..........................................................93
第十五節、(＋)-sesamin (129) 之結構鑑定..........................................................96
第十六節、(±)-pinoresinol (84) 之結構鑑定........................................................99
第十七節、(±)-syringaresinol (130) 之結構鑑定...............................................102
第十八節、(+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之結構鑑定......105
第十九節、(＋)-lariciresinol (132) 之結構鑑定................................................. 110
第二十節、(＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之結構鑑定....... 114
第二十一節、1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之結構鑑定.............120
第二十二節、pheophytin-a (135) 之結構鑑定...................................................126
第二十三節、151-hydroxypurpurin-7-lactone dimethyl ester (136) 之結構鑑定
........................................................................................................129
第二十四節、mixture of β-sitosterol (109) and stigmasterol (111) 之結構鑑定135
第二十五節、α-spinasterol (137) 之結構鑑定...................................................138
第二十六節、(11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之結構鑑定....................................................141
第二十七節、mixture of methyl palmitate (139) and methyl oleate (140) 之結
構鑑定............................................................................................147
第二十八節、(Z)-3-hexenyl-β-D-glucopyranoside (141) 之結構鑑定..................150
第六章、生物活性之研究........................................................................................153
第一節、抗結核活性研究....................................................................................153
第七章、結果與討論................................................................................................154
第八章、實驗部分....................................................................................................156
第一節、儀器與材料............................................................................................156
第二節、抗結核活性測試....................................................................................158
第三節、薄葉山礬葉部之採集與萃取................................................................160
第四節、乙酸乙酯層之分離................................................................................160
第五節、化合物數據............................................................................................165
第九章、參考文獻....................................................................................................180
Fig. A. Flowering branchlet of S. anomala Brand ......................................................... 3
Fig. B. Fruiting branchlet of S. anomala Brand ............................................................. 3
Fig. 1-1. 1H NMR and 13C NMR data of 116...............................................................28
Fig. 1a-1. 1H NMR and 13C NMR data of 116a...........................................................28
Fig. 1-2. vincoside lactam (116) 之FTIR 圖譜..........................................................28
Fig. 1-3. vincoside lactam (116) 之ESIMS 圖譜.......................................................29
Fig. 1-4. vincoside lactam (116) 之1H NMR (CD3OD, 400 MHz)圖譜....................29
Fig. 1-5. vincoside lactam (116) 之13C NMR (CD3OD, 100 MHz)圖譜..................30
Fig. 1-6. vincoside lactam (116) 之DEPT 圖譜........................................................30
Fig. 1-7. vincoside lactam (116) 之HSQC 圖譜........................................................31
Fig. 1-8. vincoside lactam (116) 之HMBC 圖譜.......................................................31
Fig. 1-9. vincoside lactam (116) 之COSY 圖譜........................................................32
Fig. 1-10. vincoside lactam (116) 之NOESY 圖譜...................................................32
Fig. 1a-2. vincoside lactam aglycone (116a) 之FTIR 圖譜.......................................33
Fig. 1a-3. vincoside lactam aglycone (116a) 之ESIMS 圖譜...................................33
Fig. 1a-4. vincoside lactam aglycone (116a) 之1H NMR (CD3OD, 200 MHz)圖譜34
Fig. 1a-5. vincoside lactam aglycone (116a) 之13C NMR (CD3OD, 50 MHz)圖譜.34
Fig. 2-1. 1H NMR and 13C NMR data of 117...............................................................37
Fig. 2-2. naucleaorine (117) 之FTIR 圖譜................................................................37
Fig. 2-3. naucleaorine (117) 之ESIMS 圖譜.............................................................38
Fig. 2-4. naucleaorine (117) 之1H NMR (CD3OD, 600 MHz)圖譜..........................38
Fig. 2-5. naucleaorine (117) 之13C NMR (CD3OD, 150 MHz)圖譜.........................39
Fig. 2-6. naucleaorine (117) 之DEPT 圖譜...............................................................39
Fig. 2-7. naucleaorine (117) 之HSQC 圖譜..............................................................40
Fig. 2-8. naucleaorine (117) 之HMBC 圖譜.............................................................40
Fig. 2-9. naucleaorine (117) 之COSY 圖譜..............................................................41
Fig. 2-10. naucleaorine (117) 之NOESY 圖譜..........................................................41
Fig. 3-1. 1H NMR and 13C NMR data of 118...............................................................43
Fig. 3-2. tectoionol A (118) 之FTIR 圖譜.................................................................43
Fig. 3-3. tectoionol A (118) 之ESIMS 圖譜..............................................................44
Fig. 3-4. tectoionol A (118) 之1H NMR (acetone-d6, 400 MHz)圖譜.......................44
Fig. 3-5. tectoionol A (118) 之13C NMR (acetone-d6, 100 MHz)圖譜......................45
Fig. 3-6. tectoionol A (118) 之DEPT 圖譜................................................................45
Fig. 3-7. tectoionol A (118) 之HSQC 圖譜...............................................................46
Fig. 3-8. tectoionol A (118) 之HMBC 圖譜..............................................................46
Fig. 3-9. tectoionol A (118) 之COSY 圖譜...............................................................47
Fig. 3-10. tectoionol A (118) 之NOESY 圖譜...........................................................47
Fig. 4-1. 1H NMR and 13C NMR data of 119...............................................................49
Fig. 4-2. linarionoside B (119) 之FTIR 圖譜............................................................49
Fig. 4-3. linarionoside B (119) 之ESIMS 圖譜.........................................................50
Fig. 4-4. linarionoside B (119) 之1H NMR (CD3OD, 400 MHz)圖譜......................50
Fig. 4-5. linarionoside B (119) 之13C NMR (CD3OD, 100 MHz)圖譜.....................51
Fig. 4-6. linarionoside B (119) 之DEPT 圖譜...........................................................51
Fig. 4-7. linarionoside B (119) 之HSQC 圖譜..........................................................52
Fig. 4-8. linarionoside B (119) 之HMBC 圖譜.........................................................52
Fig. 4-9. linarionoside B (119) 之COSY 圖譜..........................................................53
Fig. 4-10. linarionoside B (119) 之NOESY 圖譜......................................................53
Fig. 5-1. 1H NMR and 13C NMR data of 120 ..............................................................55
Fig. 5-2. blumenol B (120) 之FTIR 圖譜..................................................................55
Fig. 5-3. blumenol B (120) 之ESIMS 圖譜...............................................................56
Fig. 5-4. blumenol B (120) 之1H NMR (CD3OD, 400 MHz)圖譜...........................56
Fig. 5-5. blumenol B (120) 之13C NMR (CD3OD, 100 MHz)圖譜..........................57
Fig. 5-6. blumenol B (120) 之DEPT 圖譜................................................................57
Fig. 5-7. blumenol B (120) 之HSQC 圖譜................................................................58
Fig. 5-8. blumenol B (120) 之HMBC 圖譜...............................................................58
Fig. 5-9. blumenol B (120) 之COSY 圖譜................................................................59
Fig. 5-10. blumenol B (120) 之NOESY 圖譜...........................................................59
Fig. 6-1. 1H NMR and 13C NMR data of 121 ..............................................................61
Fig. 6-2. (+)-3-oxo-α-ionone (121) 之 FTIR 圖譜........................................................61
Fig. 6-3. (+)-3-oxo-α-ionone (121) 之 ESIMS 圖譜.....................................................61
Fig. 6-4. (+)-3-oxo-α-ionone (121) 之 1H NMR (CDCl3, 600 MHz)圖譜...................62
Fig. 6-5. (+)-3-oxo-α-ionone (121) 之 13C NMR (CDCl3, 150 MHz)圖譜..................62
Fig. 6-6. (+)-3-oxo-α-ionone (121) 之 DEPT 圖譜......................................................63
Fig. 6-7. (+)-3-oxo-α-ionone (121) 之 HSQC 圖譜......................................................63
Fig. 6-8. (+)-3-oxo-α-ionone (121) 之 HMBC 圖譜.....................................................64
Fig. 6-9. (+)-3-oxo-α-ionone (121) 之 COSY 圖譜......................................................64
Fig. 6-10. (+)-3-oxo-α-ionone (121) 之 NOESY 圖譜.................................................65
Fig. 7-1. 1H NMR data of 3..........................................................................................66
Fig. 7-2. asiatic acid (3) 之FTIR 圖譜.......................................................................67
Fig. 7-3. asiatic acid (3) 之ESIMS 圖譜....................................................................67
Fig. 7-4. asiatic acid (3) 之1H NMR (CD3OD, 200 MHz)圖譜................................68
Fig. 8-1. 1H NMR data of 122......................................................................................70
Fig. 8-2. jacoumaric acid (122) 之FTIR 圖譜...........................................................70
Fig. 8-3. jacoumaric acid (122) 之ESIMS 圖譜........................................................70
Fig. 8-4. jacoumaric acid (122) 之1H NMR (CD3OD, 200 MHz)圖譜....................71
Fig. 8-5. jacoumaric acid (122) 之1H NMR (pyridine-d5, 200 MHz)圖譜...............71
Fig. 9-1. 1H NMR and 13C NMR data of 123 ..............................................................73
Fig. 9-2. 4-epi-alyxialactone (123) 之FTIR 圖譜......................................................73
Fig. 9-3. 4-epi-alyxialactone (123) 之ESIMS 圖譜...................................................74
Fig. 9-4. 4-epi-alyxialactone (123) 之1H NMR (CDCl3, 400 MHz)圖譜.................74
Fig. 9-5. 4-epi-alyxialactone (123) 之13C NMR (acetone-d6, 150 MHz)圖譜..........75
Fig. 9-6. 4-epi-alyxialactone (123) 之DEPT 圖譜....................................................75
Fig. 9-7. 4-epi-alyxialactone (123) 之HSQC 圖譜....................................................76
Fig. 9-8. 4-epi-alyxialactone (123) 之HMBC 圖譜...................................................76
Fig. 9-9. 4-epi-alyxialactone (123) 之COSY 圖譜....................................................77
Fig. 9-10. 4-epi-alyxialactone (123) 之NOESY 圖譜...............................................77
Fig. 10-1. 1H NMR data of 124....................................................................................78
Fig. 10-2. syringaldehyde (124) 之FTIR 圖譜...........................................................79
Fig. 10-3. syringaldehyde (124) 之ESIMS 圖譜........................................................79
Fig. 10-4. syringaldehyde (124) 之 1H NMR (CDCl3, 200 MHz)圖譜.......................80
Fig. 11-1. 1H NMR and 13C NMR data of 125 ............................................................82
Fig. 11-2. salidroside (125) 之FTIR 圖譜..................................................................82
Fig. 11-3. salidroside (125) 之ESIMS 圖譜...............................................................82
Fig. 11-4. salidroside (125) 之1H NMR (CD3OD, 600 MHz)圖譜..............................83
Fig. 11-5. salidroside (125) 之13C NMR (CD3OD, 150 MHz)圖譜.............................83
Fig. 11-6. salidroside (125) 之DEPT 圖譜.................................................................84
Fig. 11-7. salidroside (125) 之HSQC 圖譜................................................................84
Fig. 11-8. salidroside (125) 之HMBC 圖譜...............................................................85
Fig. 11-9. salidroside (125) 之COSY 圖譜................................................................85
Fig. 11-10. salidroside (125) 之NOESY 圖譜............................................................86
Fig. 12-1. 1H NMR data of 126....................................................................................87
Fig. 12-2. trans-ferulic acid (126) 之FTIR 圖譜.........................................................88
Fig. 12-3. trans-ferulic acid (126) 之ESIMS 圖譜......................................................88
Fig. 12-4. trans-ferulic acid (126) 之1H NMR (CD3OD, 200 MHz)圖譜..................89
Fig. 13-1. 1H NMR data of 127....................................................................................90
Fig. 13-2. trans-methyl ferulate (127) 之FTIR 圖譜...................................................91
Fig. 13-3. trans-methyl ferulate (127) 之ESIMS 圖譜................................................91
Fig. 13-4. trans-methyl ferulate (127) 之1H NMR (CDCl3, 200 MHz)圖譜..............92
Fig. 14-1. 1H NMR data of 128....................................................................................93
Fig. 14-2. isoscopoletin (128) 之FTIR 圖譜...............................................................94
Fig. 14-3. isoscopoletin (128) 之ESIMS 圖譜............................................................94
Fig. 14-4. isoscopoletin (128) 之 1H NMR (acetone-d6, 400 MHz)圖譜....................95
Fig. 15-1. 1H NMR data of 129....................................................................................96
Fig. 15-2. (＋)-sesamin (129) 之FTIR 圖譜...............................................................97
Fig. 15-3. (＋)-sesamin (129) 之ESIMS 圖譜............................................................97
Fig. 15-4. (＋)-sesamin (129) 之 1H NMR (CDCl3, 200 MHz)圖譜...........................98
Fig. 16-1. 1H NMR data of 84......................................................................................99
Fig. 16-2. (±)-pinoresinol (84) 之FTIR 圖譜..........................................................100
Fig. 16-3. (±)-pinoresinol (84) 之ESIMS 圖譜.......................................................100
Fig. 16-4. (±)-pinoresinol (84) 之1H NMR (CDCl3, 200 MHz)圖譜......................101
Fig. 17-1. 1H NMR data of 130..................................................................................102
Fig. 17-2. (±)-syringaresinol (130) 之FTIR 圖譜....................................................103
Fig. 17-3. (±)-syringaresinol (130) 之ESIMS 圖譜.................................................103
Fig. 17-4. (±)-syringaresinol (130) 之1H NMR (CDCl3, 200 MHz)圖譜...............104
Fig. 18-1. 1H NMR and 13C NMR data of 131 ..........................................................106
Fig. 18-2. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之FTIR 圖譜..........106
Fig. 18-3. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之ESIMS 圖譜.......107
Fig. 18-4. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之1H NMR
(CDCl3, 400 MHz)圖譜.............................................................................107
Fig. 18-5. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之13C NMR
(CDCl3, 100 MHz)圖譜.............................................................................108
Fig. 18-6. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之DEPT 圖譜.........108
Fig. 18-7. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之HSQC 圖譜........109
Fig. 18-8. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之HMBC 圖譜.......109
Fig. 18-9. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之COSY 圖譜........ 110
Fig. 18-10. (+)-1-acetoxypinoresinol 4''-O-methyl ether (131) 之NOESY 圖譜.... 110
Fig. 19-1. 1H NMR data of 132.................................................................................. 112
Fig. 19-2. (＋)-lariciresinol (132) 之 FTIR 圖譜..................................................... 112
Fig. 19-3. (＋)-lariciresinol (132) 之 ESIMS 圖譜.................................................. 113
Fig. 19-4. (＋)-lariciresinol (132) 之 1H NMR (CDCl3, 400 MHz)圖譜................. 113
Fig. 20-1. 1H NMR and 13C NMR data of 133 .......................................................... 115
Fig. 20-2. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之FTIR 圖譜........... 115
Fig. 20-3. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之ESIMS 圖譜........ 116
Fig. 20-4. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之1H NMR
(CD3OD, 600 MHz)圖譜........................................................................... 116
Fig. 20-5. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之13C NMR
(CD3OD, 150 MHz)圖譜........................................................................... 117
Fig. 20-6. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之DEPT 圖譜.......... 117
Fig. 20-7. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之HSQC 圖譜......... 118
Fig. 20-8. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之HMBC 圖譜........ 118
Fig. 20-9. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之COSY 圖譜......... 119
Fig. 20-10. (＋)-lariciresinol 9-O-β-D-glucopyranoside (133) 之NOESY 圖譜..... 119
Fig. 21-1. 1H NMR and 13C NMR data of 134 ..........................................................121
Fig. 21-2. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 FTIR 圖譜......................121
Fig. 21-3. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 ESIMS 圖譜..................121
Fig. 21-4. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 1H NMR
(CDCl3, 600 MHz)圖譜.............................................................................122
Fig. 21-5. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 13C NMR
(CDCl3, 150 MHz)圖譜.............................................................................122
Fig. 21-6. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 DEPT 圖譜....................123
Fig. 21-7. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 HSQC 圖譜....................123
Fig. 21-8. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 HMBC 圖譜..................124
Fig. 21-9. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 COSY 圖譜....................124
Fig. 21-10. 1,2,3,4-tetrahydro-1-oxo-β-carboline (134) 之 NOESY 圖譜...............125
Fig. 22-1. 1H NMR data of 135..................................................................................127
Fig. 22-2. pheophytin-a (135) 之FTIR 圖譜...........................................................127
Fig. 22-3. pheophytin-a (135) 之ESIMS 圖譜........................................................128
Fig. 22-4. pheophytin-a (135) 之1H NMR (CDCl3, 400 MHz)圖譜.......................128
Fig. 23-1. 1H NMR and 13C NMR data of 136 ..........................................................130
Fig. 23-2. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之FTIR 圖譜.......130
Fig. 23-3. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之ESIMS 圖譜....131
Fig. 23-4. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之1H NMR
(CDCl3, 600 MHz)圖譜.............................................................................131
Fig. 23-5. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之13C NMR(CDCl3, 150 MHz)圖譜.............................................................................132
Fig. 23-6. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之DEPT 圖譜.....132
Fig. 23-7. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之HSQC 圖譜.....133
Fig. 23-8. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之HMBC 圖譜....133
Fig. 23-9. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之COSY 圖譜.....134
Fig. 23-10. 151-hydroxypurpurin-7-lactone dimethyl ester (136) 之NOESY 圖譜134
Fig. 24-1. 1H NMR data of 109 & 111.......................................................................136
Fig. 24-2. mixture of β-sitosterol (109) and stigmasterol (111) 之 FTIR 圖譜........136
Fig. 24-3. mixture of β-sitosterol (109) and stigmasterol (111) 之 ESIMS 圖譜.....137
Fig. 24-4. mixture of β-sitosterol (109) and stigmasterol (111) 之 1H NMR
(CDCl3, 200 MHz)圖譜.............................................................................137
Fig. 25-1. 1H NMR data of 137..................................................................................138
Fig. 25-2. α-spinasterol (137) 之 FTIR 圖譜............................................................139
Fig. 25-3. α-spinasterol (137) 之 ESIMS 圖譜.........................................................139
Fig. 25-4. α-spinasterol (137) 之1H NMR (CDCl3, 200 MHz)圖譜........................140
Fig. 26-1. 1H NMR and 13C NMR data of 138 ..........................................................142
Fig. 26-2. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之FTIR 圖譜..............................................................142
Fig. 26-3. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之ESIMS 圖譜...........................................................143
Fig. 26-4. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之1H NMR (CDCl3, 400 MHz)圖譜..........................143
Fig. 26-5. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之13C NMR (CDCl3, 100 MHz)圖譜........................144
Fig. 26-6. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid (138) 之DEPT 圖譜............................................................144
Fig. 26-7. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之HSQC 圖譜............................................................145
Fig. 26-8. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之HMBC 圖譜...........................................................145
Fig. 26-9. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之COSY 圖譜............................................................146
Fig. 26-10. (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-
dienoic acid (138) 之NOESY 圖譜.........................................................146
Fig. 27-1. 1H NMR and 13C NMR data of 139 ..........................................................147
Fig. 27-2. 1H NMR and 13C NMR data of 140 ..........................................................147
Fig. 27-3. mixture of methyl palmitate (139) and methyl oleate (140) 之FTIR
圖譜............................................................................................................148
Fig. 27-4. mixture of methyl palmitate (139) and methyl oleate (140) 之EIMS
圖譜............................................................................................................148
Fig. 27-5. mixture of methyl palmitate (139) and methyl oleate (140) 之1H NMR
(CDCl3, 400 MHz)圖譜.............................................................................149
Fig. 27-6. mixture of methyl palmitate (139) and methyl oleate (140) 之13C NMR
(CDCl3, 150 MHz)圖譜.............................................................................149
Fig. 28-1. 1H NMR data of 141..................................................................................150
Fig. 28-2. (Z)-3-hexenyl-β-D-glucopyranoside (141) 之FTIR 圖譜...........................151
Fig. 28-3. (Z)-3-hexenyl-β-D-glucopyranoside (141) 之ESIMS 圖譜........................151
Fig. 28-4. (Z)-3-hexenyl-β-D-glucopyranoside (141) 之 1H NMR
(CD3OD, 200 MHz)圖譜...........................................................................152
Table 1. Symplocos genus in Taiwan (Flora of Taiwan, 2nd edtion) ............................1
Table 2. Symplocos genus in Taiwan (Flora of China)..................................................2
Table 3. Chemical constituents of Symplocos genus.....................................................5
Table 4. 13C and 1H NMR data for 116 and 116a.........................................................27
Table 5. 13C and 1H NMR data for 117 and 116...........................................................36
Table 6. Anti-turbercular activity of isolates from the leaves of S. anomala against M.
tuberculosis H37Rv......................................................................................153

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