台灣產垂枝長葉暗羅化學成分及生物活性之研究

Studies on the Chemical Constituents and Biological Activities of the Bark of Formosan Polyalthia longifolia Benth/Hook.f.pendula

黎嘉恩(Chia-En Li)

指導教授 ： 吳永昌

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2004年)

摘要

中文摘要

由垂枝長葉暗羅 (Polyalthia longifolia Benth & Hook. f. "pendula") 之皮部總共分離得到三十二個化合物，其中二十八個化合物已確定其結構：包括六個clerodane diterpenoids:16-hydroxycleroda-13-en-15,16- olide-3-one (1), 16 (R and S)-3,13Z-kolavadien-15,16-olide-2-one (2), 16-hydroxycleroda-3,13-dien-15,16-olide (3), 16-hydroxycleroda-4(18), 13-dien-15,16-olide (4), 16-oxocleroda-3,13(14)E-dien-15-oic acid methyl ester (5), kolavenolic acid (6);二個abeo-clerodane diterpenoids: solidagonal acid (7), (4→2)-abeo-16 (R and S)-2,13Z-clerodadien- 15,16-olide-3-al (8);一個labdane diterpenoid:labd-13E-en-8-ol-15-oic acid (9);一個sesquiterpene:(-)-methyl dihydrophaseate (10);二個azafluorenes生物鹼:darienine (11), polylongine (12);一個morphinandienone生物鹼:(-)-pallidine (13);二個oxoaporphines生物鹼: liriodenine (14), lysicamine (15);一個proaporphine生物鹼: (+)-stepharine (16);一個tetrahydroprotoberberine生物鹼: (-)-stepholidine (17);一個lignan:eudesmin (18);四個amides:N-trans- sinapoylthramine (19), N-cis-feruloyltyramine (20), N-trans-feruloyltyr- amine (21), N-p-coumaroyltyramine (22);一個benzenoid:trans-methyl ferulate (23) 及五個steroids:??-sitosterol (24) & stigmasterol (25), ??-sitosterol-D-glucoside (26) & stigmasterol-D-glucoside (27), stigmast- 5-en-3-O-??-D-glucoside tetraacetate (28) 等化合物。其中化合物1為新化合物；5-7、10、13、18-20、22、23及28為第一次由暗羅 (Polyalthia) 屬植物所分離得到之化合物；而化合物5-7、10及28則為第一次從番荔枝科植物中分離得到。
上述化合物在細胞毒殺活性研究方面，化合物4對於人類乳癌細胞 (MDA-MB-231)，其IC50分別為3.22 ?慊/mL；化合物2、4與8對於人類肝癌細胞 (Hep G2)，其IC50分別為2.88 ?慊/mL、3.35 ?慊/mL與2.36 ?慊/mL，以及化合物2、3及4對於人類肝癌細胞 (Hep 3B)，其IC50分別為2.96 ?慊/mL、2.83 ?慊/mL及1.97 ?慊/mL。在抗發炎活性試驗方面,化合物3和5對於fMLP/CB引起人類白血球產生的超氧自由基具有抑制效果，其IC50分別為3.05 ± 1.13 ?慊/mL和0.60 ± 0.90?n?慊/mL。

關鍵字

垂枝長葉暗羅

並列摘要

Abstract

Polyalthia longifolia var. "pendula" (Annonaceae) is distributed India, Sri Lanka and southern Taiwan. It is an ornamental tree. We have studied on the chemical constituents from the methanolic extracts of the bark of P. longifolia var. "pendula" and their biological activities.
Thirty-two compounds were isolated, and they contain six clerodane diterpenoids:16-hydroxycleroda-13-en-15,16-olide-3-one (1), 16 (R and S) -3,13Z-kolavadien-15,16-olide-2-one (2), 16-hydroxycleroda-3,13-dien- 15,16-olide (3), 16-hydroxycleroda-4(18),13-dien-15,16-olide (4), 16-oxo -cleroda-3,13(14)E-dien-15-oic acid methyl ester (5), kolavenolic acid (6); two abeo-clerodane diterpenoids:solidagonal acid (7), (4→2)-abeo-16 (R and S)-2,13Z-clerodadien-15,16-olide-3-al (8); one labdane diterpenoid: labd-13E-en-8-ol-15-oic acid (9); one sesquiterpene:(-)-methyl dihydro- phaseate (10); two azafluorenes:darienine (11), polylongine (12); one morphinandienone:(-)-pallidine (13); two oxoaporphines:liriodenine (14), lysicamine (15); one proaporphine:(+)-stepharine (16); one tetrahydro- protoberberine:(-)-stepholidine (17); one lignan:eudesmin (18); four amides:N-trans-sinapoylthramine (19), N-cis-feruloyltyramine (20), N- trans-feruloyltyramine (21), N-p-coumaroyltyramine (22); one benzenoid: trans-methyl ferulate (23); five steroids:??-sitosterol (24) & stigmasterol (25), ??-sitosterol-D-glucoside (26) & stigmasterol-D-glucoside (27), stigmast-5-en-3-O-??-D-glucoside tetraacetate (28) and four unknown. The structures of these compounds were characterized and identified by spectral evidences. Among them, 1 is a new compound; compounds 5-7, 10, 13, 18-20, 22, 23 and 28 are isolated from genus Polyalthia for the first time. Compounds 5-7, 10 and 28 are isolated from family Annonaceae for the first time.
Compound 4 showed cytotoxicity against MDA-MB-231 cell lines with IC50 values of 3.22 ?慊/mL, respectively. Compounds 2, 4 and 8 showed cytotoxicity against Hep G2 cell lines with IC50 values of 2.88 ?慊/mL, 3.35 ?慊/mL and 2.36 ?慊/mL, respectively. Compounds 2, 3 and 4 showed cytotoxicity against Hep 3B cell lines with IC50 values of 2.96 ?慊/mL, 2.83 ?慊/mL and 1.97 ?慊/mL, respectively. Compounds 3 and 5 showed anti-inflammation effect by the fMLP/CB induced superoxide anion generation from human neutraphils with IC50 values of 3.05 ± 1.13 ?慊/mL and 0.60 ± 0.90 ?慊/mL, respectively.

並列關鍵字

Polyalthia longifolia pendula

參考文獻

第七章 參考文獻

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