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  • 學位論文

白葉釣樟與薊罌粟化學成分及生物活性之研究

Studies on the Chemical Constituents and Biological Activities of Lindera glauca and Argemone mexicana

指導教授 : 吳永昌
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摘要


以生物活性導引方法對台灣產白葉釣樟與薊罌粟進行活性成分物質的開發與化學成分的分類研究。由白葉釣樟【Lindera glauca (Sieb.&Zucc.) Bl.】地上部分離得到五十四個化合物,包括:二十個alkaloid類化合物,分別為「(+)-3-chloro-N-formylnornantenine (1),(+)-N-formylnornantenine (2),(+)-boldine (3),(+)-norboldine (4),(-)-norboldine (5),(+)-N-methyllaurotetanine (6),(+)-isoboldine (7),(+)-norisocorydine (8),(+)-laetanine (9),lysicamine (10),(+)-O-methylflavinantine (11),(-)-pallidine (12),N-cis-sinapoyltyramine (13),N-trans-sinapoyltyramine (14),N-cis-feruloyltyramine (15),N-trans-feruloyltyramine (16),N-p-coumaroyltyramine (17),(+)-norcinnamolaurine (18),(+)-tetrahydroberberine (19)及squamolone (20)」;七個flavonoid類化合物,分別為「kaempferol (21),kaempferol-3-O-arabinoside (22),kaempferol-3-O-rhamnoside (23),kaempferol-3-O-glucoside (24),quercetin (25),quercetin-3-O-rhamnoside (26)及quercetin-3-O-glucoside (27)」;六個lignan類化合物,「2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-1,4-butanediol (28),(+)-lyoniresinol (29),(+)-5-methoxyisolariciresinol (30),(+)-syringaresinol (31),(7S,8R,8’R)-5,5’-dimethoxylariciresinol (32)及2-(3’-methoxy-4’-hydroxyphenyl)-3-hydroxymethyl-2,3-dihydro-7-metho- xybenzofuran-5-(3-propanol) (33)」;一個butanolide類化合物,為akolactone A (34);一個p-quinone類化合物,為2,6-dimethoxy-p-quinone (35);一個cyclohex-2-en-1-one類化合物,為blumenol A (36);九個benzenzoid類化合物,分別為「methylparaben (37),p-hydroxybenzoic acid (38),vanillic acid (39),syringic acid (40),3,4,5-trimethoxybenzoic acid (41),3-(3,4-dihydroxyphenyl)propionic acid (42),syringaldehyde (43),3,5-dimethoxy-4-hydroxy-1-O-b-D-glucoside (44)及isotachisoide (45)」;二個terpenoid類化合物,分別為「phytol (46)與squalene (47)」;六個steroid類化合物,分別為「sitosterol (48),sitost-4-en-3-one (49),sitost-4,22-dien-3-one (50),6b-hydroxysitost-4-en-3-one (51),6b-hydroxysitost-4,22-dien-3-one (52)與sitosteryl-D-glucoside (53)」;及一個D-glucose (54)。以上化合物皆經由光譜分析證明,並與已知化合物加以比對以確認其結構式;其中化合物 1,13 為新化合物,並且除了化合物 3、6及47 外,皆為首次從本屬植物分離得到的化合物。 由薊罌粟(Argemone mexicana L.)之全草分離共得到二十九個化合物。所有化合物皆經光譜分析及化學方法確認,證實其結構包括:二十三個alkaloid類化合物,「norchelerythrine (55),O-methyl- zanthoxyline (56),sanguinarine (57),6-acetonyldihydro- sanguinarine (58),6-acetonyldihydrochelerythrine (59),arnottianamide (60),chelerythrine (61),angoline (62),pancorine (63),N-demethyloxy- sanguinarine (64),berberine (65),dehydrocheilantifoline (66),3,4-tetrahydro-1-(2’-hydroxymethyl-3’,4’-dimethoxyphenylmethyl)-6,7-methylene- dioxyisoquinoline (67),higenamine (68),(+)-reticuline (69),thalofoline (70),argemexicaine A (71),argemexicaine B (72),protopine (73),allocryptopine (74),cryptopine (75),adenine (76)及adenosine (77)」,一個flavonoid類化合物,為isorhamnetin 3-O-β-glucopyranoside (78),及五個其它類化合物,為「α-tocopherol (79),sitost-4-en-3,6-dione (80),phytol (46),sitosterol (48)及sitosteryl-D-glucoside (53)」。其中 64、71及72 為文獻上尚未記載之新化合物;56及67為首次自天然物分離取得;46、53、60、62、63、66、68、70、76、77、78、79與80為首次從本屬植物分離到的化合物。 對所獲得化合物進行生物活性試驗,其中化合物2,6-dimethoxy-p-quinone (35)對於胃癌細胞(NUGC)在10 mg/ml的抑制濃度下的細胞株存活百分比為1 ﹪,故具有有意義的細胞毒殺作用。另外化合物chelerythrine (61),angoline (62),3,4-tetrahydro-1-(2’-hydroxymethyl-3’,4’-dimethoxyphenylmethyl)-6,7-methylene- dioxyisoquinoline (67),adenine (76)及sitost-4-en-3,6-dione (80),對於胃癌細胞(NUGC)在50 mg/ml的抑制濃度下的細胞株存活百分比分別為:1 ﹪、0 ﹪、64 ﹪、33 ﹪及15 ﹪;化合物angoline (62)及adenine (76)對於鼻咽癌細胞(HONE-1),在50 mg/ml的抑制濃度下的細胞株存活百分比分別為 1 ﹪及37 ﹪,均具有有意義的細胞毒殺作用。

並列摘要


Bioactivity-guided fractionation and chromatographic separation led to the isolation and characterization of active principles from two Formosan plants. Twenty alkaloids, (+)-3-chloro-N-formylnornantenine (1), (+)-N-formylnornantenine (2), (+)-boldine (3), (+)-norboldine (4), (-)-norboldine (5), (+)-N-methyllaurotetanine (6), (+)-isoboldine (7), (+)-norisocorydine (8), (+)-laetanine (9), lysicamine (10), (+)-O-methylflavinantine (11), (-)-pallidine (12), N-cis-sinapoyltyramine (13), N-trans-sinapoyltyramine (14), N-cis-feruloyltyramine (15), N-trans-feruloyltyramine (16), N-p-coumaroyltyramine (17), (+)-norcinnamo- laurine (18), (+)-tetrahydroberberine (19) and squamolone (20); seven flavonoids, kaempferol (21), kaempferol-3-O-arabinoside (22), kaempferol-3-O-rhamnoside (23), kaempferol-3-O-glucoside (24), quercetin (25), quercetin-3-O-rhamnoside (26) and quercetin-3-O-glucoside (27); six lignans, 2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)- methyl]-1,4-butanediol (28), (+)-lyoniresinol (29), (+)-5-methoxyisolariciresinol (30), (+)-syringaresinol (31), (7S,8R,8’R)-5,5’-dimethoxylariciresinol (32) and 2-(3’-methoxy-4’-hydroxyphenyl)-3-hydroxymethyl-2,3-dihydro-7-methoxybenzofuran-5-(3-propanol) (33); one butanolide, akolactone A (34); one p-quinone, 2,6-dimethoxy-p-quinone (35); one cyclohex-2-en-1-one, blumenol A (36); nine benzenzoids, methylparaben (37), p-hydroxybenzoic acid (38), vanillic acid (39), syringic acid (40), 3,4,5-trimethoxybenzoic acid (41), 3-(3,4-dihydroxyphenyl)propionic acid (42), syringaldehyde (43), 3,5-dimethoxy-4-hydroxy-1-O-b-D-glucoside (44) and isotachisoide (45); two terpenoids, phytol (46) and squalene (47); six steroids, sitosterol (48),sitost-4-en-3-one (49),sitost-4,22-dien-3-one (50),6b-hydroxysitost-4-en-3-one (51),6b-hydroxysitost-4,22-dien-3-one (52) and sitosteryl-D-glucoside (53) and D-glucose (54) were obtained from the aerial parts of Lindera glauca (Sieb.&Zucc.) Bl.. The structures of all compounds were identified on the basis of their spectral data and chemical evidences. Among them, 1 and 13 are new compounds; beside compounds 3, 6 and 47 other compounds were isolated for the first time from this genus. Twenty three alkaloids, norchelerythrine (55), O-methylzanthoxy- line (56), sanguinarine (57), 6-acetonyldihydrosanguinarine (58), 6-acetonyldihydrochelerythrine (59), arnottianamide (60), chelerythrine (61), angoline (62), pancorine (63), N-demethyloxysanguinarine (64), berberine (65), dehydrocheilantifoline (66), 3,4-tetrahydro-1-(2’-hydroxy- methyl-3’,4’-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline (67), higenamine (68), (+)-reticuline (69), thalofoline (70), argemexicaine A (71), argemexicaine B (72), protopine (73), allocryptopine (74), cryptopine (75), adenine (76) and adenosine (77), one flavonoid, isorhamnetin 3-O-β-glucopyranoside (78), five other compounds, α-tocopherol (79), sitost-4-en-3,6-dione (80), phytol (46), sitosterol (48) and sitosteryl-D-glucoside (53) were isolated from the herds of Argemone mexicana L.. The structures of all compounds were identified on the basis of their spectral and chemical evidences. Among them, 64, 71 and 72 are new compounds, 56 and 67 are new natural compounds. 46, 53, 60, 62, 63, 66, 68, 70, 76, 77, 78, 79 and 80 were isolated for the first time from this genus. Compound 2,6-dimethoxy-p-quinone (35) exhibited 99 ﹪inhibition against human gastric cancer (NUGC) cancer cell line at 10 mg/ml, and chelerythrine (61), angoline (62), 3,4-tetrahydro-1-(2’-hydroxymethyl-3’,4’-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline (67), adenine (76) and sitost-4-en-3,6-dione (80) also showed significant inhibition against human gastric cancer (NUGC) cell line at the concentration of 50 mg/ml, with inhibition values 99 ﹪, 100 ﹪, 36 ﹪, 67 ﹪and 85 ﹪, respectively. Angoline (62) and adenine (76) showed significant inhibition of human nasopharyngeal carcinoma (HONE-1) cell line at the concentration of 50 mg/ml, the inhibition values are 99 ﹪and 63 ﹪, respectively.

參考文獻


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