本研究是針對軟珊瑚 Lemnalia flava 的有機萃取物尋找具有生物活性的化學成分。從軟珊瑚L. flava 中共分離出十四個天然化合物1-14，其中九個為新的化合物flavalin B-J (1-9)；化合物1-7為nardosinane sesquiterpenoids 類化合物， 8-9 為 nornardosinane sesquiterpenoids 類化合物以及五個已知化合物 10-14 ，2-oxolemnacarnol (10) 、lemnacarnol (11) 、armatin F (12) 、(2R)-2-hydroxylemnal-1(10)-en-12-one (13) 和 laevinol B (14)。上述化合物的構造均是由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。化合物1 並經由X-ray晶體繞射來
進一步證明其化合物之結構，而化合物13 絕對立體構造，可經由Mosher's酯化反應及比對的方式加以確定。
本研究中將所獲得的化合物 1-3 進行神經保護作用測試。在神經保護作用測試結果顯示化合物1 在抵抗 6-羥基多巴胺(6-OHDA)引起人類兒茶酚胺類神經母瘤細胞(SH-SY5Y)神經細胞凋亡的能力；化合物1–13 進行癌細胞株的細胞毒殺與抗發炎活性測試。化合物1-13 對人類乳癌細胞(MCF-7)、人類結腸癌細胞(WiDr)、人類喉
癌細胞(Hep2)、人類髓母細胞瘤癌細胞(Daoy)、人類急性淋巴細胞白血病T淋巴細胞(CCRF-CEM)、人類結直腸腫瘤細胞(DLD-1)、人類前骨髓性白血病細胞(HL-60)和老鼠血癌細胞(P388D1)進行測試，發現沒有細胞毒殺及抗發炎的活性。

In order to search for bioactive compounds from the organic extracts of a Formosan soft coral Lemnalia flava fourteen natural compounds, including seven new nardosinane sesquiterpenoids flavalin B-H (1-7),
two new nornardosinane sesquiterpenoids flavalins I-J (8-9), along with five known compounds, 2-oxolemnacarnol (10), lemnacarnol (11), armatin F (12), (2R)-2-hydroxylemnal-1(10)-en-12-one (13) and laevinol B (14) were isolated from L. flava. The structures of these compounds were established by the detailed spectral analysis (IR, MS, 1D, 2D NMR)
and by comparison of the spectral data with those of the related known compounds. The structure of 1 was unambiguously proven by X-ray diffraction analysis. The absolute configuration of 13 was further
determined by a modified Mosher's method.
The neuroprotective effect compounds of 1–3 against the damage of 6-hydroxydopamine (6-OHDA) toward SH-SY5Y cells was also measured. The cytotoxicity of 6-OHDA on SH-SY5Y cells was significantly reduced by pretreatment of 1 at various concentrations. The
cytotoxicity of compounds 1–13 against human breast carcinoma (MCF-7), human colon carcinoma (WiDr), human laryngeal carcinoma (HEp 2), human medulloblastoma (Daoy) T-cell acute lymphoblastic
leukemia(CCRF-CEM), colon adenocarcinoma (DLD-1), human promyelocytic leukemia (HL-60) and murine leukemia (P388D1) cell lines was studied. The ability of 1–13 to inhibit the up-regulation of
pro-inflammatory iNOS (inducible nitric oxide synthase) and COX-2(cyclooxygenase-2) proteins in LPS (lipopolysaccharide)-stimulated RAW264.7 macrophage cells was examined, and it was
shown that no cytotoxic and anti-inflammatory activity could be found for these compounds.

目 錄 頁 次
中文摘要 X
英文摘要XI
化合物1-14 化學結構XII
第一章、緒論
第一節、前言 1
第二節、研究動機 2
第三節、文獻回顧 4
第二章、生物材料與研究方法
第一節、研究流程 18
第二節、Lemnalia flava 物種的採集及分類地位20
第三節、Lemnalia flava 的分離流程21
第四節、實驗設備儀器及材料23
第三章、化合物之結構證明
第一節、軟珊瑚 Lemnalia flava 所分離出之化合物的結構之解析 26
(一)、Flavalin B (1) 結構之解析26
(二)、Flavalin C (2) 結構之解析36
(三)、Flavalin D (3) 結構之解析46
(四)、Flavalin E (4) 結構之解析55
(五)、Flavalin F (5) 結構之解析65
(六)、Flavalin G (6) 結構之解析74
(七)、Flavalin H (7) 結構之解析83
(八)、Flavalin I (8) 結構之解析93
(九)、Flavalin J (9) 結構之解析102
(十)、2-Oxolemnacarnol (10) 結構之解析111
(十一)、Lemnacarnol (11) 結構之解析115
(十二)、Armatin F (12) 結構之解析119
(十三)、(2R)-2-hydroxylemnal-1(10)-en-12-one (13) 結構之解析123
(十四)、Laevinol B (14) 結構之解析129
第二節、化學反應步驟 133
第三節、化合物物理性質及圖譜數據整理 134
第四章、生物活性試驗結果
第一節、細胞毒殺活性試驗方法 137
第二節、抗發炎活性試驗方法 139
第三節、神經保護試驗方法 141
第四節、生物活性試驗結果 145
第五章、結論 150
第六章、參考文獻153
附錄、化合物1 之 X-ray 實驗數據 158
圖 目 錄
Figure 2-1. Lemnalia flava 圖20
Figure 2-2. Lemnalia flava 軟珊瑚的分離流程22
Figure 3-1-1. 1H–1H COSY and selective HMBC correlations of 1. 28
Figure 3-1-2. X-ray crystal structure for 1. 28
Figure 3-1-3. IR spectrum of 1. 30
Figure 3-1-4. ESIMS spectrum of 1. 30
Figure 3-1-5. HRESIMS spectrum of 1. 31
Figure 3-1-6. 1H NMR spectrum of 1. 31
Figure 3-1-7. 1H NMR (2.3~6.5 ppm) spectrum of 1. 32
Figure 3-1-8. 13C NMR spectrum of 1. 32
Figure 3-1-9. DEPT spectra of 1. 33
Figure 3-1-10. HMQC spectrum of 1. 33
Figure 3-1-11. COSY spectrum of 1. 34
Figure 3-1-12. HMBC spectrum of 1. 34
Figure 3-1-13. NOESY spectrum of 1. 35
Figure 3-2-1. 1H–1H COSY and selective HMBC correlations of 2. 37
Figure 3-2-2. Selected NOESY correlations of 2. 38
Figure 3-2-3. IR spectrum of 2. 40
Figure 3-2-4. ESIMS spectrum of 2. 40
Figure 3-2-5. HRESIMS spectrum of 2. 41
Figure 3-2-6. 1H NMR spectrum of 2. 41
Figure 3-2-7. 1H NMR (3.0~4.5 ppm) spectrum of 2. 42
Figure 3-2-8. 13C NMR spectrum of 2. 42
Figure 3-2-9. DEPT spectra of 2. 43
Figure 3-2-10. HMQC spectrum of 2. 43
Figure 3-2-11. COSY spectrum of 2. 44
Figure 3-2-12. HMBC spectrum of 2. 44
Figure 3-2-13. NOESY spectrum of 2. 45
Figure 3-3-1. 1H–1H COSY and selective HMBC correlations of 3. 47
Figure 3-3-2. Selected NOESY correlations of 3. 48
Figure 3-3-3. IR spectrum of 3. 49
Figure 3-3-4. ESIMS spectrum of 3. 49
Figure 3-3-5. HRESIMS spectrum of 3. 50
Figure 3-3-6. 1H NMR spectrum of 3. 50
Figure 3-3-7. 1H NMR (3.4~5.1 ppm) spectrum of 3. 51
Figure 3-3-8. 13C NMR spectrum of 3. 51
Figure 3-3-9. DEPT spectra of 3. 52
Figure 3-3-10. HMQC spectrum of 3. 52
Figure 3-3-11. COSY spectrum of 3. 53
Figure 3-3-12. HMBC spectrum of 3. 53
Figure 3-3-13. NOESY spectrum of 3. 54
Figure 3-4-1. 1H–1H COSY and selective HMBC correlations of 4. 56
Figure 3-4-2. Selected NOESY correlations of 4. 57
Figure 3-4-3. IR spectrum of 4. 59
Figure 3-4-4. ESIMS spectrum of 4. 59
Figure 3-4-5. HRESIMS spectrum of 4. 60
Figure 3-4-6. 1H NMR spectrum of 4. 60
Figure 3-4-7. 1H NMR (2.5~5.1 ppm) spectrum of 4. 61
Figure 3-4-8. 13C NMR spectrum of 4. 61
Figure 3-4-9. DEPT spectra of 4. 62
Figure 3-4-10. HMQC spectrum of 4. 62
Figure 3-4-11. COSY spectrum of 4. 63
Figure 3-4-12. HMBC spectrum of 4. 63
Figure 3-4-13. NOESY spectrum of 4. 64
Figure 3-5-1. 1H–1H COSY and selective HMBC correlations of 5. 66
Figure 3-5-2. Selected NOESY correlations of 5. 67
Figure 3-5-3. IR spectrum of 5. 68
Figure 3-5-4. ESIMS spectrum of 5. 68
Figure 3-5-5. HRESIMS spectrum of 5. 69
Figure 3-5-6. 1H NMR spectrum of 5. 69
Figure 3-5-7. 1H NMR (2.9~5.2 ppm) spectrum of 5. 70
Figure 3-5-8. 13C NMR spectrum of 5. 70
Figure 3-5-9. DEPT spectra of 5. 71
Figure 3-5-10. HMQC spectrum of 5. 71
Figure 3-5-11. COSY spectrum of 5. 72
Figure 3-5-12. HMBC spectrum of 5. 72
Figure 3-5-13. NOESY spectrum of 5. 73
Figure 3-6-1. 1H–1H COSY and selective HMBC correlations of 6. 75
Figure 3-6-2. Selected NOESY correlations of 6. 76
Figure 3-6-3. IR spectrum of 6. 77
Figure 3-6-4. ESIMS spectrum of 6. 77
Figure 3-6-5. HRESIMS spectrum of 6. 78
Figure 3-6-6. 1H NMR spectrum of 6. 78
Figure 3-6-7. 1H NMR (2.5~5.7 ppm) spectrum of 6. 79
Figure 3-6-8. 13C NMR spectrum of 6. 79
Figure 3-6-9. DEPT spectra of 6. 80
Figure 3-6-10. HNQC spectrum of 6. 80
Figure 3-6-11. COSY spectrum of 6. 81
Figure 3-6-12. HMBC spectrum of 6. 81
Figure 3-6-13. NOESY spectrum of 6. 82
Figure 3-7-1. 1H–1H COSY and selective HMBC correlations of 7. 84
Figure 3-7-2. Selected NOESY correlations of 7. 85
Figure 3-7-3. IR spectrum of 7. 87
Figure 3-7-4. ESIMS spectrum of of 7. 87
Figure 3-7-5. HESIMS spectrum of 7. 88
Figure 3-7-6. 1H NMR spectrum of 7. 88
Figure 3-7-7. 1H–NMR (1.8~5.4 ppm) spectrum of 7. 89
Figure 3-7-8. 13C NMR spectrum of 7. 89
Figure 3-7-9. DEPT spectrum of 7. 90
Figure 3-7-10. HMQC spectrum of 7. 90
Figure 3-7-11. COSY spectrum of 7. 91
Figure 3-7-12. HMBC spectrum of 7. 91
Figure 3-7-13. NOESY spectrum of 7. 92
Figure 3-8-1. 1H–1H COSY and selective HMBC correlations of 8. 94
Figure 3-8-2. Selected NOESY correlations of 8. 95
Figure 3-8-3. IR spectrum of 8. 96
Figure 3-8-4. ESIMS spectrum of 8. 96
Figure 3-8-5. HRESIMS spectrum of 8. 97
Figure 3-8-6. 1H NMR spectrum of 8. 97
Figure 3-8-7. 1H–NMR (1.8~4.4 ppm) spectrum of 8. 98
Figure 3-8-8. 13C NMR spectrum of 8. 98
Figure 3-8-9. DEPT spectra of 8. 99
Figure 3-8-10. HMQC spectrum of 8. 99
Figure 3-8-11. COSY spectrum of 8. 100
Figure 3-8-12. HMBC spectrum of 8. 100
Figure 3-8-13. NOESY spectrum of 8. 101
Figure 3-9-1. 1H–1H COSY and selective HMBC correlations of 9. 103
Figure 3-9-2. Selected NOESY correlations of 9. 104
Figure 3-9-3. IR spectrum of 9. 105
Figure 3-9-4. ESIMS spectrum of 9. 105
Figure 3-9-5. HRESIMS spectrum of 9. 106
Figure 3-9-6. 1H NMR spectrum of 9. 106
Figure 3-9-7. 1H–NMR (2.0~4.8 ppm) spectrum of 9. 107
Figure 3-9-8. 13C NMR spectrum of 9. 107
Figure 3-9-9. DEPT spectrum of 9. 108
Figure 3-7-10. HMQC spectrum of 9. 108
Figure 3-7-11. COSY spectrum of 9. 109
Figure 3-7-12. HMBC spectrum of 9. 109
Figure 3-7-13. NOESY spectrum of 9. 110
Figure 3-10-1. ESIMS spectrum of 10. 113
Figure 3-10-2. 1H NMR spectrum of 10. 113
Figure 3-10-3. 13C NMR spectrum of 10. 114
Figure 3-11-1. ESIMS spectrum of 11. 117
Figure 3-11-2. 1H NMR spectrum of 11. 117
Figure 3-11-3. 13C NMR spectrum of 11. 118
Figure 3-12-1. ESIMS spectrum of 12. 121
Figure 3-12-2. 1H NMR spectrum of 12. 121
Figure 3-12-3. 13C NMR spectrum of 12. 122
Figure 3-13-1. 1H NMR chemical shift differences (Δδ) for the MTPA esters of 13. 124
Figure 3-13-2. ESIMS spectrum of 13. 126
Figure 3-13-3. 1H NMR spectrum of 13. 126
Figure 3-13-4. 13C NMR spectrum of 13. 127
Figure 3-13-5. 1H -NMR spectrum of 13a 127
Figure 3-13-6. 1H-NMR spectrum of 13b 128
Figure 3-14-1. ESIMS spectrum of 14. 131
Figure 3-14-2. 1H NMR spectrum of 14. 131
Figure 3-14-3. 13C NMR spectrum of 14. 132
Reaction 3-2-1. 製備化合物13 的(S)-以及(R)-MTPA esters 133
Reaction 3-2-2. 由化合物5 進行乙醯化反應133
Figure 4-1. 化合物1–3 和4–13 之濃度為10 μM 時，抑制LPS 誘發老鼠巨噬細胞(macrophage, RAW264.7)產生iNOS(inducible nitric oxide synthase)之抗發炎活性篩檢結果。147
Figure 4-2. 化合物1–3 和4–13 均為 10 μΜ 抑制 LPS 誘發老鼠巨噬細胞(mouse macrophage cell line, RAW 264.7)產生COX-2 (cyclooxygenase-II)之抗發炎活性篩檢結果。148
Figure 4-3. 化合物1–3 和4–13 均為10 μΜ 抑制 LPS 誘發老鼠巨噬細胞(mouse macrophage cell line, RAW264.7)產生iNOS與COX-2 實驗之內控制β–actin 蛋白質之表現。 149
Figure 5-1. Proposed biosynthetic pathway 1–3 152

表 目 錄 頁 次
Table 1-1. 軟珊瑚 Lemnalia 所含天然物及其生物活性文獻回顧 4
Table 1-2. Cadinene 類天然物及其生物活性文獻回顧14
Table 3-1. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 1 29
Table 3-2. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 2 39
Table 3-3. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 3 48
Table 3-4. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 4 58
Table 3-5. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 5 67
Table 3-6. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 6 76
Table 3-7. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 7 86
Table 3-8. 1H and 13C NMR, 1H–1H COSY, and HMBC data of 8 95
Table 3-9. 1H and 13C NMR, 1H–1H COSY, and HMBC correlations of 9 104
Table 3-10. 1H and 13C NMR Data of 10 112
Table 3-11. 1H and 13C NMR Data of 11 116
Table 3-12. 1H and 13C NMR Data of 12 120
Table 3-13. 1H and 13C NMR Data of 13 125
Table 3-14. 1H and 13C NMR Data of 14 130
Table 4-1. Cytotoxicity (ED50 μg/mL) of compounds 1–14 145
Table 4-2. Cytotoxicity (ED50 μg/mL) of compounds 1–14 146
Table 4-3. Figure 4-1 之數據整理147
Table 4-4. Figure 4-2 之數據整理148
Table 4-5. Figure 4-3 之數據整理149
Table 4-6. Neuron protection of compounds 1–3 150

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