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Persea americana Mill. (Lauraceae) is an evergreen tree, distributed in tropical and subtropical regions around the world. Until now, the bark, leaves, fruits and seeds of P. americana have been extensively studied. Previous studies on this plant identified various classes of chemical constituents, such as monoterpenoids, sesquiterpenoids, triterpenoids, flavonoids, steroids, and carotenoids, and especially long-chain fatty alcohol derivatives. From the previous investigations, this plant showed numerous bioactivities, including cytotoxicity, antifungal, antibacterial, acetyl-CoA carboxylase inhibition, nitric oxide and superoxide generation inhibition, and liver injury suppressing effects.
Approximately 1300 species of Formosan plants have been screened for antitubercular activity against Mycobacterium tuberculosis H37Rv in vitro, and the methanolic extract of the unripe pulp of P. americana was shown with antitubercular activity. The aims of this study are the isolation of chemical constituents and their antitubercular activity. The methanolic extract of the unripe pulp of P. americana was partitioned into ethyl acetate and water-soluble layers.
Bioassay-guided fractionation of the active ethyl acetate-soluble layer has led to the isolation of four new aliphatic alcohols: avocadenols A-D (1-4), avocadoin (5), and eight compounds with acetonide moiety: (2R,4S)-2,4-acetonide- 16-heptadecene-1,2,4-triol (6), (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4- triol (7), (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8), (2R,4S,6E)-2,4- acetonide-heptadec-6-en-16-yne-1,2,4-triol (9), (2S,4S)-1,2-acetonide-16- heptadecene-1,2,4-triol (10), (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4- triol (11), (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) and (2S,4S,6E)-1,2- acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) together with twelve known compounds: oleic acid (14), cedrelopsin (15), (2R,4R)-1-acetoxy-2,4- dihydroxyheptadec-16-ene (22), (2R,4R)-1- acetoxy-2,4-dihydroxyheptadec-16-yne (23), (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24), (2R,4R)-1,2,4-trihydroxyheptadec- 16-yne (25), 1,4-diacetoxy-2-hydroxyheptadec-16-ene (30), (2R,4R)-1,2,4- trihydroxynonadecane (53), (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54), scopoletin (77), mixtures of β-sitosterol (125) and stigmasterol (126). According to the biosynthesis pathway, we could presume that 6-13 are artificial products produced during purification. The structures of these isolates were elucidated by spectroscopic analysis.
Avocadenols A-B (1-2), (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6), (2R,4R)-1,2,4-trihydroxynonadecane (53), (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24), and (2R,4R)-1,2,4-trihydroxyheptadec-16-yne (25) showed antitubercular activity against M. tuberculosis H37Rv in vitro with MIC values of 24.0, 33.8, 50.0, 24.9, and 35.7 μg/mL, respectively.
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目 錄
目錄..................................................................... ...................................... I-Ⅱ
圖目錄 Ⅲ-XII
表目錄 XIII
中文摘要 XIV
英文摘要 XV
Glossary of Abbreviations XVI
第一章 緒言 1
第二章 研究動機與目的 3
第三章 酪梨過去文獻回顧
第一節 化學成分 5
第二節 藥理活性 21
第四章 萃取與分離 28
第五章 化合物之結構鑑定
第一節 avocadenol A (1) 31
第二節 avocadenol B (2) 39
第三節 avocadenol C (3) 46
第四節 avocadenol D (4) 53
第五節 avocadoin (5) 60
第六節 (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 67
第七節 (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 76
第八節 (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 84
第九節 (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 92
第十節 (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 100
第十一節 (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 109
第十二節 (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 117
第十三節 (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 125
第十四節 (2R,4R)-1,2,4-trihydroxynonadecane (53) 133
第十五節 (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 136
第十六節 (2R,4R)-1,2,4-trihydroxyheptadec-16-yne (25) 143
第十七節 (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 146
第十八節 (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 153
第十九節 (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-yne (23) 160
第二十節 (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 164
第二十一節 oleic acid (14) 171
第二十二節 scopoletin (77) 174
第二十三節 cedrelopsin (15) 176
第二十四節 混合物β-sitosterol (125) 與stigmasterol (126) 178
第六章 抗結核活性之研究 180
第七章 結論 181
第八章 實驗部分
第一節 儀器與材料 183
第二節 抗結核活性測試 185
第三節 抽出與分離 187
第四節 化合物之實驗數據 191
第九章 參考文獻 203
圖 目 錄
Fig. A. Flowering branches of Persea americana (Campus of KMU on 99/03/03) 2
Fig. B. Fruiting branches of Persea americana (Campus of KMU on 99/07/07) 2
Scheme 1. 酪梨未熟果肉之分離流程 28
Fig. 1-1. avocadenol A (1) 之FTIR圖譜 34
Fig. 1-2. avocadenol A (1) 之ESIMS圖譜 34
Fig. 1-3. avocadenol A (1) 之HRESIMS圖譜 35
Fig. 1-4. avocadenol A (1) 之1H NMR圖譜 (CDCl3, 400 MHz) 35
Fig. 1-5. avocadenol A (1) 之13C NMR圖譜 (CDCl3, 100 MHz) 36
Fig. 1-6. avocadenol A (1) 之DEPT圖譜 36
Fig. 1-7. avocadenol A (1) 之HSQC圖譜 37
Fig. 1-8. avocadenol A (1) 之HMBC圖譜 37
Fig. 1-9. avocadenol A (1) 之COSY圖譜 38
Fig. 1-10. avocadenol A (1) 之NOESY圖譜 38
Fig. 2-1. avocadenol B (2) 之FTIR圖譜 41
Fig. 2-2. avocadenol B (2) 之ESIMS圖譜 41
Fig. 2-3. avocadenol B (2) 之HRESIMS圖譜 42
Fig. 2-4. avocadenol B (2) 之1H NMR圖譜 (CDCl3, 400 MHz) 42
Fig. 2-5. avocadenol B (2) 之13C NMR圖譜 (CDCl3, 100 MHz) 43
Fig. 2-6. avocadenol B (2) 之DEPT圖譜 43
Fig. 2-7. avocadenol B (2) 之HSQC圖譜 44
Fig. 2-8. avocadenol B (2) 之HMBC圖譜 44
Fig. 2-9. avocadenol B (2) 之COSY圖譜 45
Fig. 2-10. avocadenol B (2) 之NOESY圖譜 45
Fig. 3-1. avocadenol C (3) 之FTIR圖譜 48
Fig. 3-2. avocadenol C (3) 之ESIMS圖譜 48
Fig. 3-3. avocadenol C (3) 之HRESIMS圖譜 49
Fig. 3-4. avocadenol C (3) 之1H NMR圖譜 (acetone-d6, 600 MHz) 49
Fig. 3-5. avocadenol C (3) 之13C NMR圖譜 (acetone-d6, 150 MHz) 50
Fig. 3-6. avocadenol C (3) 之DEPT圖譜 50
Fig. 3-7. avocadenol C (3) 之HSQC圖譜 51
Fig. 3-8. avocadenol C (3) 之HMBC圖譜 51
Fig. 3-9. avocadenol C (3) 之COSY圖譜 52
Fig. 3-10. avocadenol C (3) 之NOESY圖譜 52
Fig. 4-1. avocadenol D (4) 之FTIR圖譜 55
Fig. 4-2. avocadenol D (4) 之ESIMS圖譜 55
Fig. 4-3. avocadenol D (4) 之HRESIMS圖譜 56
Fig. 4-4. avocadenol D (4) 之1H NMR圖譜 (CDCl3, 600 MHz) 56
Fig. 4-5. avocadenol D (4) 之13C NMR圖譜 (CDCl3, 150 MHz) 57
Fig. 4-6. avocadenol D (4) 之DEPT圖譜 57
Fig. 4-7. avocadenol D (4) 之HSQC圖譜 58
Fig. 4-8. avocadenol D (4) 之HMBC圖譜 58
Fig. 4-9. avocadenol D (4) 之COSY圖譜 59
Fig. 4-10. avocadenol D (4) 之NOESY圖譜 59
Fig. 5-1. avocadoin (5) 之FTIR圖譜 62
Fig. 5-2. avocadoin (5) 之ESIMS圖譜 62
Fig. 5-3. avocadoin (5) 之HRESIMS圖譜 63
Fig. 5-4. avocadoin (5) 之1H NMR圖譜 (CDCl3, 400 MHz) 63
Fig. 5-5. avocadoin (5) 之13C NMR圖譜 (CDCl3, 100 MHz) 64
Fig. 5-6. avocadoin (5) 之DEPT圖譜 64
Fig. 5-7. avocadoin (5) 之HSQC圖譜 65
Fig. 5-8. avocadoin (5) 之HMBC圖譜 65
Fig. 5-9. avocadoin (5) 之COSY圖譜 66
Fig. 5-10. avocadoin (5) 之NOESY圖譜 66
Fig. 6-1. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之FTIR圖譜 71
Fig. 6-2. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之ESIMS圖譜 71
Fig. 6-3. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之HRESIMS
圖譜 72
Fig. 6-4. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之1H NMR
圖譜 (CDCl3, 400 MHz) 72
Fig. 6-5. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之13C NMR
圖譜 (CDCl3, 100 MHz) 73
Fig. 6-6. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之DEPT圖譜 73
Fig. 6-7. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之HSQC圖譜 74
Fig. 6-8. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之HMBC圖譜 74
Fig. 6-9. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之COSY圖譜 75
Fig. 6-10. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 之NOESY
圖譜 75
Fig. 7-1. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
FTIR圖譜 79
Fig. 7-2. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
ESIMS圖譜 79
Fig. 7-3. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
HRESIMS圖譜 80
Fig. 7-4. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
1H NMR圖譜 (CDCl3, 400 MHz) 80
Fig. 7-5. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
13C NMR圖譜 (CDCl3, 100 MHz) 81
Fig. 7-6. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
DEPT圖譜 81
Fig. 7-7. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
HSQC圖譜 82
Fig. 7-8. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
HMBC圖譜 82
Fig. 7-9. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
COSY圖譜 83
Fig. 7-10. (2R,4S,6E)-2,4-acetonide-6-en-16-heptadecene-1,2,4-triol (7) 之
NOESY圖譜 83
Fig. 8-1. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之FTIR圖譜 87
Fig. 8-2. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之ESIMS圖譜 87
Fig. 8-3. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之HRESIMS
圖譜 88
Fig. 8-4. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之1H NMR圖譜
(CDCl3, 400 MHz) 88
Fig. 8-5. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之13C NMR圖譜
(CDCl3, 100 MHz) 89
Fig. 8-6. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之DEPT圖譜 89
Fig. 8-7. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之HSQC圖譜 90
Fig. 8-8. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之HMBC圖譜 90
Fig. 8-9. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之COSY圖譜 91
Fig. 8-10. (2R,4S)-2,4-acetonide-16-heptadecyne-1,2,4-triol (8) 之NOESY
圖譜 91
Fig. 9-1. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之FTIR
圖譜 95
Fig. 9-2. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
ESIMS圖譜 95
Fig. 9-3. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
HRESIMS圖譜 96
Fig. 9-4. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
1H NMR圖譜 (CDCl3, 600 MHz) 96
Fig. 9-5. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
13C NMR圖譜 (CDCl3, 150 MHz) 97
Fig. 9-6. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
DEPT圖譜 97
Fig. 9-7. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
HSQC圖譜 98
Fig. 9-8. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
HMBC圖譜 98
Fig. 9-9. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
COSY圖譜 99
Fig. 9-10. (2R,4S,6E)-2,4-acetonide-heptadec-6-en-16-yne-1,2,4-triol (9) 之
NOESY圖譜 99
Fig. 10-1. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之FTIR圖譜
104
Fig. 10-2. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之ESIMS圖譜
104
Fig. 10-3. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之HRESIMS
圖譜 105
Fig. 10-4. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之1H NMR圖譜
(CDCl3, 400 MHz) 105
Fig. 10-5. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之13C NMR
圖譜 (CDCl3, 100 MHz) 106
Fig. 10-6. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之DEPT圖譜
106
Fig. 10-7. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之HSQC圖譜
107
Fig. 10-8. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之HMBC圖譜
107
Fig. 10-9. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之COSY圖譜
108
Fig. 10-10. (2S,4S)-1,2-acetonide-16-heptadecene-1,2,4-triol (10) 之NOESY
圖譜 108
Fig. 11-1. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之FTIR
圖譜 112
Fig. 11-2. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
ESIMS圖譜 112
Fig. 11-3. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
HRESIMS圖譜 113
Fig. 11-4. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
1H NMR圖譜 (CDCl3, 600 MHz) 113
Fig. 11-5. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
13C NMR圖譜 (CDCl3, 150 MHz) 114
Fig. 11-6. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
DEPT圖譜 114
Fig. 11-7. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
HSQC圖譜 115
Fig. 11-8. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
HMBC圖譜 115
Fig. 11-9. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
COSY圖譜 116
Fig. 11-10. (2S,4S,6E)-1,2-acetonide-heptadec-6,16-diene-1,2,4-triol (11) 之
NOESY圖譜 116
Fig. 12-1. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之FTIR
圖譜 120
Fig. 12-2. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之ESIMS
圖譜 120
Fig. 12-3. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之HRESIMS
圖譜 121
Fig. 12-4. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之1H NMR
圖譜 (CDCl3, 600 MHz) 121
Fig. 12-5. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之13C NMR
圖譜 (CDCl3, 150 MHz) 122
Fig. 12-6. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之DEPT
圖譜 122
Fig. 12-7. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之HSQC
圖譜 123
Fig. 12-8. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之HMBC
圖譜 123
Fig. 12-9. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之COSY
圖譜 124
Fig. 12-10. (2S,4S)-1,2-acetonide-16-heptadecyne-1,2,4-triol (12) 之NOESY
圖譜 124
Fig. 13-1. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
FTIR圖譜 128
Fig. 13-2. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
ESIMS圖譜 128
Fig. 13-3. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
HRESIMS圖譜 129
Fig. 13-4. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
1H NMR圖譜 (CDCl3, 600 MHz) 129
Fig. 13-5. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
13C NMR圖譜 (CDCl3, 150 MHz) 130
Fig. 13-6. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
DEPT圖譜 130
Fig. 13-7. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
HSQC圖譜 131
Fig. 13-8. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
HMBC圖譜 131
Fig. 13-9. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
COSY圖譜 132
Fig. 13-10. (2S,4S,6E)-1,2-acetonide-heptadec-6-en-16-yne-1,2,4-triol (13) 之
NOESY圖譜 132
Fig. 14-1. (2R,4R)-1,2,4-trihydroxynonadecane (53) 之FTIR圖譜 134
Fig. 14-2. (2R,4R)-1,2,4-trihydroxynonadecane (53) 之ESIMS圖譜 134
Fig. 14-3. (2R,4R)-1,2,4-trihydroxynonadecane (53) 之1H NMR圖譜
(CDCl3, 200 MHz) 135
Fig. 15-1. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之FTIR圖譜 138
Fig. 15-2. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之ESIMS圖譜 138
Fig. 15-3. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之1H NMR圖譜
(CDCl3, 400 MHz) 139
Fig. 15-4. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之13C NMR圖譜
(CDCl3, 100 MHz) 139
Fig. 15-5. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之DEPT圖譜 140
Fig. 15-6. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之HSQC圖譜 140
Fig. 15-7. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之HMBC圖譜 141
Fig. 15-8. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之COSY圖譜 141
Fig. 15-9. (2R,4R)-1,2,4-trihydroxyheptadec-16-ene (24) 之NOESY圖譜 142
Fig. 16-1. (2R,4R)-1,2,4-trihydroxyheptadec-16-yne (25) 之FTIR圖譜 144
Fig. 16-2. (2R,4R)-1,2,4-trihydroxyheptadec-16-yne (25) 之ESIMS圖譜 144
Fig. 16-3. (2R,4R)-1,2,4-trihydroxyheptadec-16-yne (25) 之1H NMR圖譜
(CDCl3, 200 MHz) 145
Fig. 17-1. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之FTIR圖譜 148
Fig. 17-2. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之ESIMS圖譜 148
Fig. 17-3. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之1H NMR圖譜
(CDCl3, 600 MHz) 149
Fig. 17-4. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之13C NMR圖譜
(CDCl3, 150 MHz) 149
Fig. 17-5. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之DEPT圖譜 150
Fig. 17-6. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之HSQC圖譜 150
Fig. 17-7. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之HMBC圖譜 151
Fig. 17-8. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之COSY圖譜 151
Fig. 17-9. (2R,4R,6E)-1,2,4-trihydroxynonadec-6-ene (54) 之NOESY圖譜 152
Fig. 18-1. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之FTIR圖譜 155
Fig. 18-2. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之
ESIMS圖譜 155
Fig. 18-3. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之1H NMR
圖譜 (CDCl3, 600 MHz) 156
Fig. 18-4. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之13C NMR
圖譜 (CDCl3, 150 MHz) 156
Fig. 18-5. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之DEPT
圖譜 157
Fig. 18-6. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之HSQC
圖譜 157
Fig. 18-7. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之HMBC
圖譜 158
Fig. 18-8. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之COSY
圖譜 158
Fig. 18-9. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-ene (22) 之NOESY
圖譜 159
Fig. 19-1. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-yne (23) 之FTIR圖譜 162
Fig. 19-2. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-yne (23) 之ESIMS
圖譜 162
Fig. 19-3. (2R,4R)-1-acetoxy-2,4-dihydroxyheptadec-16-yne (23) 之1H NMR
圖譜 (CDCl3, 200 MHz) 163
Fig. 20-1. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之FTIR圖譜 166
Fig. 20-2. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之ESIMS
圖譜 166
Fig. 20-3. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之1H NMR圖譜
(CDCl3, 400 MHz) 167
Fig. 20-4. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之13C NMR圖譜
(CDCl3, 100 MHz) 167
Fig. 20-5. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之DEPT
圖譜 168
Fig. 20-6. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之HSQC
圖譜 168
Fig. 20-7. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之HMBC
圖譜 169
Fig. 20-8. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之COSY
圖譜 169
Fig. 20-9. (2R,4R)-1,4-diacetoxy-2-hydroxyheptadec-16-ene (30) 之NOESY圖譜
170
Fig. 21-1. oleic acid (14) 之FTIR圖譜 172
Fig. 21-2. oleic acid (14) 之ESIMS圖譜 172
Fig. 21-3. oleic acid (14) 之1H NMR圖譜 (CDCl3, 200 MHz) 173
Fig. 21-4. oleic acid (14) 之13C NMR圖譜 (CDCl3, 50 MHz) 173
Fig. 22-1. scopoletin (77) 之FTIR圖譜 175
Fig. 22-2. scopoletin (77) 之1H NMR圖譜 (CDCl3, 200 MHz) 175
Fig. 23-1. cedrelopsin (15) 之FTIR圖譜 177
Fig. 23-2. cedrelopsin (15) 之1H NMR圖譜 (CDCl3, 200 MHz) 177
Fig. 24-1. 混合物β-sitosterol (125) 與stigmasterol (126) 之FTIR圖譜 179
Fig. 24-2. 混合物β-sitosterol (125) 與stigmasterol (126) 之1H NMR圖譜
(CDCl3, 200 MHz) 179
表 目 錄
Table 1. 酪梨未熟果肉之甲醇萃取物對M. tuberculosis strain H37RV之影響 1
Table 2. 酪梨於化學成分的過去文獻回顧 5
Table 3. 酪梨 (樟梨) 於中華本草之記載 21
Table 4. 酪梨於藥理活性的過去文獻回顧 22
Table 5. 1,2,4-trihydroxyheptadec-16-ene之四個stereoisomers物化性質比較 33
Table 6. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6) 與6'' 之比旋光度與
NMR數值比較 70
Table 7. (2R,4S)-2,4-acetonide-16-heptadecene-1,2,4-triol (6)、
(2S,4S)-1,2-acetonide- 16-heptadecene-1,2,4-triol (10) 與10'' 之比旋光度
與NMR數值比較 103
Table 8. Antitubercular activities of isolates from the unripe pulp of
Persea americana against M. tuberculosis strain H37RV 180
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