臺灣博碩士論文加值系統

本研究乃是將豆科植物，黃野百合(Crotalaria pallida Ait.)與大豬屎豆(Crotalaria assamica Benth.)；金絲桃科植物，雙花金絲桃(Hypericum geminiflorum Hemsl.)與福木(Garcinia subelliptica Merr.)；分別進行成分分離及純化並進行生物活性之探討。
由黃野百合(Crotalaria pallida Ait.)枝幹的甲醇(methanol)抽出物分離得到十五個化合物，其中包含十個已知化合物：b-sitosterol (1)、lupeol (2)、apigenin (3)、genistein (4)、derrone (8)、morin (9)、weighetone (10)、2¢-hydroxygenistein (11)、diadzein (13)、2¢-hydroxydiadzein (15)及五個新的化合物：crotafurans A (5)、B (6)、C (7)、5,7,4¢-trihydroxy-
2¢-methoxyisoflavone (12)、crotafuran E (14)。將以上所得到的化合物進行抗發炎(anti-inflammatory effect)生物活性之篩選。結果顯示crotafurans A (5)及B (6)具有抑制以lipopolysaccharide (LPS)引發RAW 264.7 cells生成nitric oxide的作用並呈現與濃度相關的抑制活性，其IC50值分別為23.0 ± 1.0及19.0 ± 0.2 mM。而crotafurans B (6)及E (14)則具有抑制以LPS/interferon-g (IFN-g)誘發N9 cells生成nitric oxide之作用，其IC50值分別為9.4 ± 0.9及13.9 ± 1.1 mM。且crotafuran A (5)有抑制以formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB)刺激老鼠嗜中性白血球(neutrophil)釋出b-glucuronidase及lysozyme的作用，其IC50值分別為7.8 ± 1.4及9.5 ± 2.1 mM。
由大豬屎豆(Crotalaria assamica Benth.)種子之甲醇(methanol)抽出物分離得到五個化合物，其中包含四個已知化合物：taxifolin (16)、naringenin (17)、quercetin-7-O-b-D-glucopyranoside (18)、naringenin-7-
O-b-D-glucopyranoside (20)及一個新的化合物：crotafuran D (19)。
由雙花金絲桃(Hypericum geminiflorum Hemsl.)葉部之甲醇(methanol)抽出物分離得到一個新骨架化合物：hypertricone (21)。
由福木(Garcinia subelliptica Merr.)種子之氯仿(choloform)抽出物分離得到十四個化合物，其中包括三個已知化合物：garsubellin A (22)、garcinielliptin oxide (25)、garsubellin D (26)及十一個新的化合物: garcinielliptones A (23)、B (24)、C (27)、D (28)、E (29)、F (30)、G (31)、H (32)、I (33)、J (34)及3b,20x-dihydroxy-lanost-24-ene (35)，其中31及34為新骨格化合物並將以上的化合物進行抗發炎活性篩選。已知化合物，garsubellin A (22)具有抑制以compound 48/80刺激老鼠腹腔巨噬細胞釋出b-glucuronidase的活性，其IC50值為15.6 ± 2.5mM，而garcinielliptin oxide (25)則具有抑制以compound 48/80刺激老鼠腹腔巨噬細胞釋出b-glucuronidase及lysozyme的活性，其IC50值分別為18.2 ± 3.6及20.0 ± 2.7 mM。而在以fMLP/CB刺激老鼠嗜中性白血球(neutrophil)釋出b-glucuronidase及lysozyme的活性方面，garcinielliptin oxide (25)具有很強的抑制活性，其IC50值分別為15.7 ± 3.0，23.9 ± 3.2 mM，且garcinielliptone F (30)也呈現與濃度相關的抑制活性，其IC50值分別為26.9 ± 2.6及20.0 ± 1.3 mM。另外化合物25及30還具有抑制以fMLP/CB刺激老鼠嗜中性白血球釋出超氧陰離子的作用，其IC50值分別為17.9 ± 1.5及17.0 ± 0.9 mM。而Garcinielliptone I (33)則具有抑制以LPS/IFN-g誘發N9 cells釋出NO2-的作用，其IC50值為7.4 ± 0.2 mM。

In research directed at the bioactive constituents of Leguminosae plants, five new compounds were isolated from the bark of Crotalaria pallida, and one new compound was isolated from the seeds of Crotalaria assamica. Also, from Guttiferae plants, one new compound was isolated from the leaves of Hypericum geminiflorum and eleven new compounds were isolated from the seeds of Garcinia subelliptica. These new structures were determined by spectroscopic data and computer-generated 3D drawing.
From C. pallida, ten known compounds, b-sitosterol (1), lupeol (2), apigenin (3), genistein (4), derrone (8), morin (9), weighetone (10), 2¢-hydroxygenistein (11), diadzein (13), and 2¢-hydroxydiadzein (15) were identified in addition to the five new compounds, crotafurans A (5), B (6), and C (7), 5,7,4¢-trihydroxy-2¢-methoxyisoflavone (12), and crotafuran E (14). Compounds 5 and 6 showed significant inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage-like cells in concentration-
dependent manners with IC50 values of 23.0 ± 1.0 and 19.0 ± 0.2 mM, respectively. Moreover, 5 produced a concentration-dependent inhibition of the release of b-glucuronidase and lysozyme from rat neutrophils in response to formyl-Met-Leu-Phe/cytochalasin B (fMLP/CB) with IC50 values of 7.8 ± 1.4 and 9.5 ± 2.1 mM, respectively. Compounds 6 and 14 also inhibited the LPS/interferon-g (IFN-g)-stimulated NO production in N9 microglial cells with IC50 values of 9.4 ± 0.9 and 13.9 ± 1.1 mM, respectively.
From C. assamica, four known compounds, taxifolin (16), naringenin (17), quercetin-7-O-b-D-glucopyranoside (18), and naringenin-7-O-b-D-glucopyranoside (20) were isolated in addition to the one new compound, crotafuran D (19).
One compound with a novel skeleton, hypertricone (21), was isolated from the leaves of H. geminiflorum.
From G. subelliptica, three known compounds, garsubellin A (22), garcinielliptin oxide (25), and garsubellin D (26), and eleven new compounds, garcinielliptones A-J (23, 24, 27-34) and 3b,20x-dihydroxy-
lanost-24-ene (35), were isolated. Two of the new compounds (31, 34) had a new skeleton. Known compound 22 showed a potent inhibitory effect on the release of b—glucuronidase from rat peritoneal mast cells stimulated with compound 48/80 in a concentration-dependent manner with an IC50 value of 15.6 ± 2.5 mM, and known compound 25 showed a potent inhibitory effect on the release of b—glucuronidase and lysozyme from this assay in a concentration-dependent manners with IC50 values of 18.2 ± 3.6 mM and 20.0 ± 2.7 mM, respectively. Compounds 25 and 30 showed potent inhibitory effects on the release of b—glucuronidase and lysozyme from neutrophils stimulated with fMLP/CB in a concentration-dependent manners with IC50 values of 15.7 ± 3.0 and 23.9 ± 3.2 mM for 25, and 26.9 ± 2.6 and 20.0 ± 1.3 mM for 30. Compounds 25 and 30 also showed potent inhibitory effects on superoxide anion formation from neutrophils stimulated with fMLP/CB in a concentration-dependent manners with IC50 values of 17.9 ± 1.5 and 17.0 ± 0.9 mM, respectively. Garcinielliptone I (33) showed a potent inhibitory effect on NO2- production in the culture media of N9 cells in response to LPS/IFN-g in a concentration-dependent manner with an IC50 value of 7.4 ± 0.2 mM.

目 錄
中文摘要---------------------------------------------------------------- 1
英文摘要---------------------------------------------------------------- 4
第一章 研究動機與目的--------------------------------------------- 13
第二章 豆科植物成分研究------------------------------------------ 17
第一節 黃野百合研究回顧--------------------------------- 17
第二節 植物型態--------------------------------------------- 18
第三節 抽取與分離------------------------------------------ 19
第一項 b-Sitosterol (1) 的結構式證明------------------ 21
第二項 Lupeol (2) 的結構式證明------------------------- 24
第三項 Apigenin (3)的結構式證明----------------------- 27
第四項 Genistein (4) 的結構式證明--------------------- 30
第五項 Crotafuran A (5) 的結構式證明----------------- 33
第六項 Crotafuran B (6) 的結構式證明----------------- 40
第七項 Crotafuran C (7) 的結構式證明----------------- 46
第八項 Derrone (8) 的結構式證明----------------------- 51
第九項 Morin (9) 的結構式證明-------------------------- 55
第十項 Weighteone (10) 的結構式證明----------------- 58
第十一項 2¢-Hydroxygenistein (11) 的結構式證明---- 62
第十二項 5,7,4¢-Trihydroxy-2¢-methoxyisoflavone (12) 的結構式證明------------------------------------ 65
第十三項 Diadzein (13) 的結構式證明------------------ 70
第十四項 Crotafuran E (14) 的結構式證明------------- 73
第十五項 2¢-Hydroxydiadzein (15) 的結構式證明----- 78
第四節 大豬屎豆研究回顧-------------------------------- 81
第五節 植物型態--------------------------------------------- 81
第六節 抽取與分離------------------------------------------ 82
第一項 Taxifolin (16) 的結構式證明--------------------- 84
第二項 Naringenin (17) 的結構式證明------------------ 87
第三項 Quercetin-7-b-O-D-glucopyranoside (18) 的結構式證明------------------------------------------- 90
第四項 Crotafuran D (19) 的結構式證明---------------- 94
第五項 Naringenin-7-b-O-D-glucopyranoside (20) 的結構式證明---------------------------------------- 99
第三章 金絲桃科植物成分研究------------------------------------ 103
第一節 雙花金絲桃研究回顧----------------------------- 103
第二節 植物型態--------------------------------------------- 103
第三節 抽取與分離------------------------------------------ 105
第一項 Hypertricone (21) 的結構式證明--------------- 106
第四節 福木研究回顧--------------------------------------- 114
第五節 植物型態--------------------------------------------- 115
第六節 抽取與分離------------------------------------------ 116
第一項 Garsubellin A (22) 的結構式證明--------------- 118
第二項 Garcinielliptone A (23) 的結構式證明--------- 126
第三項 Garcinielliptone B (24) 的結構式證明--------- 133
第四項Garcinielliptin oxide (25) 的結構式證明------- 139
第五項 Garsubellin D (26) 的結構式證明--------------- 147
第六項 Garcinielliptone C (27) 的結構式證明--------- 153
第七項 Garcinielliptone D (28) 的結構式證明--------- 158
第八項 Garcinielliptone E (29) 的結構式證明--------- 164
第九項 Garcinielliptone F (30) 的結構式證明---------- 169
第十項 Garcinielliptone G (31) 的結構式證明--------- 176
第十一項 Garcinielliptone H (32) 的結構式證明------ 184
第十二項 Garcinielliptone I (33) 的結構式證明------- 193
第十三項 Garcinielliptone J (34) 的結構式證明------- 199
第十四項 3b,20x-Dihydroxy-lanost-24-ene (35) 的結構式證明---------------------------------------- 207
第四章 生物活性試驗結果----------------------------------------- 216
第五章 討論與結論--------------------------------------------------- 228
第六章 實驗部分------------------------------------------------------ 232
參考文獻---------------------------------------------------------------- 276
論文著作------------------------------------------------------- 284

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