根據本研究室過去的研究，薑科植物薑黃地上部富含黃酮醇類成分，同屬植物莪朮地上部揮發油成分已有報導，但較高極性成分仍無報導，因此本研究擬探討莪朮地上部之成分。
將莪朮地上部之乙醇萃取物經極性分割後劃分為乙腈、乙酸乙酯、正丁醇和水可溶部分，並進一步對乙腈、乙酸乙酯和正丁醇可溶部分進行成分分離。過程中使用Sephadex LH-20、silica gel和逆相層析管柱、離心式分配層析，以及半製備HPLC等分離技術，共計得到23個化合物，經由核磁共振譜及質譜技術分析確認其結構，包括14個黃酮醇類：quercetin (3)、quercetin 3-O– β-D-glucuronide (1)、α-L-rhamnosyl-(1→2)-β-D-glucuronide (4)、α-L-rhamnosyl-(1→2)-β-D-galactoside (8)、β-D-glucoside (12)、α-L-arabinopyranoside (14)、α-L-rhamnoside (15)、β-D-glucuronide methyl ester (16)及α-L-rhamnosyl-(1→2)-α-L-arabinopyranoside (17)，kaempferol 3-O– β-D-glucuronide (2)、α-L-rhamnosyl-(1→2)-β-D-glucuronide (7)、α-L-rhamnosyl-(1→2)-β-D-galactoside (9)、β-D-glucoside (11)及β-D-galactoside (13); 2個核苷類：adenosine (5)與uridine (6); 3個苯丙烷類：5-O-caffeoylshikimic acid (10)、methyl feruloyl malate (19)及p-coumaric acid (20);3個倍半萜類：epi-oxycurcumenol (21)、(1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone (22)及zedoarondiol (23)和1個苯甲酸衍生物：4-hydroxybenzoic acid (18)。其中化合物21為首次分離出之天然物，雖然已由合成製備。

Our recent studies on the aerial part of Curcuma longa (Zingiberaceae) indicated it to be rich in flavonols. The essential oils from the aerial part of the related species, Curcuma aeruginosa Roxb., have been reported but other constituents remain disclosed. Thus this thesis was aimed to investigate the chemical constituents from the aerial part.
The ethanol extract of the aerial part of C. aeruginosa was divided into fractions soluble in MeCN, EtOAc, n-BuOH, and water via liquid-liquid partitioning. The MeCN, EtOAc, and n-BuOH -soluble fractions were chromatographed over Sephadex LH-20, silica gel, and reversed-phase columns, centrifugal partition chromatography, and semi-preparative RP-HPLC, monitored by ESI-MS and TLC. This effort led to the isolation of 23 compounds, whose structures were determined based on 1H and 13C NMR spectroscopic analyses and MS data. They are 14 flavonols: quercetin (3), quercetin 3-O– β-D-glucuronide (1), α-L-rhamnosyl-(1→2)-β-D-glucuronide (4), α-L-rhamnosyl-(1→2)-β-D-galactoside (8), β-D-glucoside (12), α-L-arabinopyranoside (14), α-L-rhamnoside (15), β-D-glucuronide methyl ester (16), and α-L-rhamnosyl-(1→2)-α-L-arabinopyranoside (17); kaempferol 3-O– β-D-glucuronide (2), α-L-rhamnosyl-(1→2)-β-D-glucuronide (7), α-L-rhamnosyl-(1→2)-β-D-galactoide (9), β-D-glucoside (11), and β-D-galactoide (13); two nucleosides: adenosine (5) and uridine (6); three phenylpropanoids: 5-O-caffeoylshikimic acid (10), methyl feruloyl malate (19), and p-coumaric acid (20); three sesquiterpenoids: epi-oxycurcumenol (21), (1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone (22), and zedoarondiol (23); one phenolics: 4-hydroxybezoic acid (18). Among these, compound 21 is a new natural product although it has been prepared synthetically.

總目錄
中文摘要 I
英文摘要 ⅠⅠ
目錄 III
表目錄 (List of tables) Ⅴ
圖目錄 (List of figures) ⅤⅠ
流程圖目錄 (List of scheme) ⅤⅠⅠ
辭彙 (Glossary) ⅤIII
目錄
1. 緒論及研究目的 1
1.1 研究目的 1
1.2 莪朮之簡介 2
1.3 莪朮生物活性之研究 3
1.4 薑黃屬 (Curcuma) 成分之文獻回顧 4
2. 實驗結果與討論 25
2.1 黃酮醇化合物 (Flavonols) 27
2.1.1 Quercetin 3-O-β-D-glucuronide (1) 之結構解析 27
2.1.2 Kaempferol 3-O-β-D-glucuronide (2) 之結構解析 27
2.1.3 Quercetin (3) 之結構解析 29
2.1.4 Quercetin 3-O-α-L-rhamnosyl-(1→2)-β-D-glucuronide (4) 之結構解析 30
2.1.5 Kaempferol 3-O-α-L-rhamnosyl-(1→2)-β-D-glucuronide (7) 之結構解析 30
2.1.6 Quercetin 3-O-α-L-rhamnosyl-(1→2)-β-D-galactopyranoside (8) 之結構解析 32
2.1.7 Kaempferol 3-O-α-L-rhamnosyl-(1→2)-β-D-galactopyranoside (9) 之結構解析 33
2.1.8 化合物11~16之結構解析 37
2.1.9 Quercetin 3-O-α-L-rhamnosyl-(1→2)-α-L-arabinopyranoside (17)之結構解析 41
2.2 核苷類(neucleoside)成分 43
2.2.1 Adenosine (5) 之結構解析 43
2.2.2 Uridine (6) 之結構解析 43
2.3 苯丙烷類(Phenylpropanoid)成分 45
2.3.1 5-O-Caffeoylshikimic acid (10) 之結構解析 45
2.3.2 Methyl feruloyl malate (19) 之結構解析 47
2.3.3 p-Coumaric acid (20) 之結構解析 49
2.4 倍半萜類成分 (Sesquiterpenoids) 50
2.4.1 Epi-oxycurcumenol (21) 之結構解析 50
2.4.2 (1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone (22) 之結構解析 52
2.4.3 Zedoarondiol (23) 之結構解析 55
2.5 苯甲酸衍生物 (Benzoic acid derivatives) 57
2.5.1 4-Hydroxybenzoic acid (18) 之結構解析 57
2.6 討論 58
2.6.1黃酮醇的分離 58
2.6.2 Epi-oxycurcumenol (21) 結構解析與文獻比較………..…………………………………………………………….. ...58
2.6.3 Zedoarondiol (23) 結構解析與文獻比較…………………………..60
3. 實驗部分 61
3.1 儀器與材料 61
3.1.1 理化性質測定儀器 61
3.1.2 成分分離之儀器與材料 61
3.1.3 試劑與溶媒 62
3.1.4 電腦軟體 63
3.2 植物來源 63
3.3 莪朮地上部成分萃取與純化 63
3.3.1 莪朮之萃取 63
3.3.2 莪朮地上部正丁醇可溶部分之分離 64
3.3.3 莪朮地上部乙酸乙酯可溶部分之分離 68
3.3.4 莪朮地上部乙腈可溶部分之來源 71
3.3.5 莪朮地上部乙腈可溶部分之分離 72
3.4 HPLC-DAD-SPE-NMR分析 74
3.4.1 Fr. E-7-4之分析條件 74
3.4.2 Fr. E-6-5之分析條件 74
3.5 化合物之物理數據 77
參考資料 82
附圖 91

表目錄 (List of tables)
Table 1. Compounds isolated from Curcuma plants. 4
Table 2. 1H NMR (200 MHz for 1, 400MHz for 2) and 13C NMR data (100 MHz) data of 1 and 2 (CD3OD). 28
Table 3. 1H NMR data of 3 (CD3OD, 200 MHz). 29
Table 4. 1H NMR data of 4 and 7 (CD3OD, 400 MHz). 31
Table 5. 1H NMR (600 MHz for 8, 500 MHz for 9) data of 8 and 9 (CD3OD). 35
Table 6. Results of HPLC-DAD analysis of 8 and 9. 36
Table 7. 1H NMR (400 MHz for 11、12, 600 MHz for 13) data of 11-13 (CD3OD). 39
Table 8. 1H NMR data of 14-16 (CD3OD, 600 MHz). 40
Table 9. 1H NMR data of 17 (CD3OD, 600 MHz). 42
Table 10. 1H NMR (400 MHz for 5, 200 MHz for 6) data of 5 and 6 (CD3OD). 44
Table 11. 1H NMR (200 MHz) and 13C NMR data (100 MHz) of 10 (CD3OD). 46
Table 12. 1H NMR of 19 (CD3OD, 400 MHz). 48
Table 17 1H NMR data of 20 (CD3OD, 200 MHz) 49
Table 13. 1H NMR of 21 (CDCl3, 200 MHz) 51
Table 14 1H (400 MHz) and 13C NMR (100 MHz) data of 22 (CDCl3) 54
Table 15 1H (400 MHz) and 13C NMR (100 MHz) data of 23. 56
Table 16. 1H NMR data of 18 (CD3OD, 200 MHz). 57
Table 18 13C NMR (50 MHz) of 21, oxycurcumenol and epi-oxycurcumenol88 (CDCl3) 59
圖目錄 (List of figures)
Figure 1. Curcuma aeruginosa Roxb. 2
Figure 2. Monoterpenoids and sesquiterpenoids isolated from Curcuma plants. 12
Figure 3. Sesquiterpenoids isolated from Curcuma plants (I) 13
Figure 4. Sesquiterpenoids isolated from Curcuma plants (II). 14
Figure 5. Sesquiterpenoids and diterpenoids isolated from Curcuma plants. 15
Figure 6. Curcuminoids isolated from Curcuma plants (I). 16
Figure 7. Curcuminoids isolated from Curcuma plants (II). 17
Figure 8. Curcuminoids isolated from Curcuma plants (III). 18
Figure 9. Curcuminoids isolated from Curcuma plants (IV). 19
Figure 10. Curcuminoids isolated from Curcuma plants (V). 20
Figure 11. Curcuminoids isolated from Curcuma plants (VI). 21
Figure 12. Curcuminoids isolated from Curcuma plants.(VII) 22
Figure 13. Curcuminoids, flavonoids and triacylglycerol isolated from Curcuma plants. 23
Figure 14. Fatty acids, phenylpropanoid and other compounds isolated from Curcuma plants. 24
Figure 15. Key HMBC correlation of compound 22 53
Figure 16. Structure of isozedoarondiol. 56
Figure 17. (a) Oxycurcumenol (b) epi-oxycurcumenol (ketal form) (c) epi-oxycurcumenol 59
Figure 18. Structure of ent-zedoarondiol 60
Figure 19. CD data of compound 23 60
Figure 20. HPLC chromatograms of Fr. E-7-4 and Fr. E-6-5. 76
流程圖目錄 (List of scheme)
Scheme 1 Fractionation of the EtOH extract of Curcuma aeruginosa 63
Scheme 2 Separation scheme of the n-BuOH soluble layer of the EtOH extract of Curcuma aeruginosa 67
Scheme 3 Separation scheme of the EtOAc soluble layer of the EtOH extract of Curcuma aeruginosa 70
Scheme 4 Fractionation of the CH2Cl2 soluble part of Curcuma aeruginosa 71
Scheme 5 Separation scheme of the ACN soluble layer of the EtOH extract of Curcuma aeruginosa 73

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