蘭嶼山欖葉部成分之研究

Studies on the constituents of the leaves of Planchonella duclition (Blanco) Bakhuizan

吳政億(Cheng-Yi Wu)

指導教授 ： 李宗徽 博士

臺北醫學大學/藥學院/生藥學研究所/碩士(2005年)

摘要

蘭嶼山欖主要分布於東南亞一帶，而在台灣僅見於蘭嶼，為台灣的原生種植物。過去，我們在預試驗中發現其葉部萃取物的低極性層對於乳癌細胞株MCF-7有顯著的抗癌活性。鑑於此，遂對於蘭嶼山欖葉部的萃出物進行化學成分的探究，計分離、鑑定出19個成分。分別為2α,3α,19α,23-tetrahydroxy-13,27-cyclours-11-en-28-oic acid (1)、myrianthic acid (2)、ursolic acid (3)、corosolic acid (4)、3-epi-pomolic acid (5)、rotundic acid (6)、jacoumaric acid (7)、spinasterol (8)、rutin (9)、kaempferol 3-O-rutinoside (10)、(2R,3R)-dihydrokaempferol 6-C-β-D-glucopyranoside (11)、kaempferol 6-C-β-D-glucopyranoside (12)、quercetin 3-O-β-D-glucopyranoside (13)、kaempferol 3-O-β-D-glucopyranoside (14)、kaempferol 3-O-α-L-rhamnopyranoside (15)、(-)-epi-catechin (16)、aviculin (17)、1',3',4',6',2,3,4,6-octa-O-acetyl-sucrose (18) 和2-O-methyl-(1,3,4,5-tetra-O-acetyl-?-D-fructofuranoside) (19)。根據這些化合物骨架的不同，可將其歸類為三?酸類 (1–7)、固醇類 (8)、黃酮類 (9–16)、木酚類 (17) 和醣類 (18, 19)，其中化合物1和11為新的結構。此外化合物3和7對於人類乳癌細胞株MCF-7和大腸癌細胞株HT-29均有顯著的抗癌活性，其半致死濃度範圍為5.8 ? 1.4到6.5 ? 1.9 μM之間。

關鍵字

蘭嶼山欖 ； 山欖科 ； 細胞毒性 ； 三?類 ； 黃酮類 ； 蘭嶼

並列摘要

Planchonella duclitan (Blanco) Bakhuizan (Sapotaceae) is distributed mainly in the areas of South-East Asia. In Taiwan, it is a native species, and is found only in Lan-yu island. In our preliminary studies, the low polar layer of the leaf extracts of P. duclitan was found to exhibit significant anti-proliferation activities toward human breast cancer cell line MCF-7. A chemical investigation of the leaf extracts of this plant was thus undertaken, and has led to the isolation of nineteen compounds 1–19. The structures of 1–19 were established to be 2α,3α,19α,23-tetrahydroxy-13,27-cyclours- 11-en-28-oic acid (1), myrianthic acid (2), ursolic acid (3), corosolic acid (4), 3-epi-pomolic acid (5), rotundic acid (6), jacoumaric acid (7), spinasterol (8), rutin (9), kaempferol 3-O-rutinoside (10), (2R,3R)-dihydrokaempferol 6-C-β-D-glucopyranoside (11), kaempferol 6-C-β-D-glucopyranoside (12), quercetin 3-O-β-D-glucopyranoside (13), kaempferol 3-O-β-D-glucopyranoside (14), kaempferol 3-O-α-L-rhamnopyranoside (15), (-)-epi-catechin (16), aviculin (17), 1',3',4',6',2,3,4,6-octa-O-acetyl- sucrose (18), and 2-O-methyl-(1,3,4,5-tetra-O-acetyl-?-D- fructofuranoside) (19) on the basis of spectroscopic analysis. These structures were grouped to be ursane type triterpene acids (1–7), a steroid (8), flavonoid glycosides (9–16), a lignan glycoside (17), and sugars (18, 19). Of these compounds identified, 1 and 11 are new. Additionally, compounds 3 and 7 showed significant cytotoxicity toward human human breast carcinoma MCF-7 cell line and colorectal carcinoma HT29 cell line with IC50 values ranging from 5.8 ? 1.4 to 6.5 ? 1.9 μM.

並列關鍵字

Planchonella duclitan ； Sapotaceae ； MCF-7 ； HT29 ； triterpene ； flavonoid ； ursane ； Lan-yu island

參考文獻

1. Yang T. Y. A. Sapotaceae. In: Flora of Taiwan; Editorial committee of the Flora of Taiwan, Department of Botany, National Taiwan University: Taipei, Taiwan, 1998; Vol. 4; p85.

21. Taniguchi S.; Imayoshi Y.; Kobayashi E.; Takamatsu Y.; Ito H.;Hatano T.; Sakagami H.; Tokuda H.;Nishino H.; Sugita D.; Shimura S.; Yoshida T. Phytochemistry 2002, 59,315.

5. N. P. Sahu Phytochemistry 1996, 41,883.

9. Paper, D. H. Planta Med. 1998, 64,686.

10. Luo X. D.; Margaret J. B.;Edward J. K. J. Agric. Food Chem. 2002, 50, 1379.