紅花八角果實Prenylated C6-C3類活性化合物研究

Studies on the Bioactive Prenylated C6-C3 compounds from the fruits of Illicium arborescens Hayata

林雅竹(Ya-Chu Lin)

指導教授 ： 沈雅敬

國立臺灣大學/醫學院/藥學研究所/碩士(2009年)

https://doi.org/10.6342/NTU.2009.02595

摘要

本論文主要研究台灣產紅花八角 (Illicium arborescens Hayata) 果實之CH2Cl2與EtOAc混合液萃取物並分析鑑定其prenylated C6-C3類成分，分離共得12個化合物，包含3個新的與9個已知化合物。

由紅花八角分離得到一個類似prenylated C6-C3類化合物之新骨架化合物、一個prenylated C6-C3類化合物、一個phytoquinoid化合物，分別命名為illicaborin A (1)、illicaborin B (2)、illicaborin C (3)，以及9個已知化合物，分別是1-allyl-2,3-
(methylenedioxy)-5-methoxybenzene (4) 、apiol (5) 、 illicinone E (6) 、11-epi-
illilinone E (7)、2,3-dehydroillifunone C (8)、illifunone A (9) 、illifunone B (10) 、illifunone C (11)、illifunone D (12)。

化合物1為一新骨架化合物，特徵為prenylated C6-C3骨架之C-2位置增加一個CH2OH基團，化合物2具有典型的prenylated C6-C3骨架，化合物3為phytoquinoid化合物。以上所有化合物結構是利用各種物理數據，包括紅外線、質譜、紫外線、旋光值以及配合各種核磁共振圖譜，包含1D和2D的圖譜並且比對過去文獻相關化合物的數據而得。立體結構解析方面，則是利用NOESY圖譜決定。化合物活性相關實驗則是委託郭曜豪老師實驗室協助測定，受測化合物1-3、8與11中，僅有2對於HEp-2、Daoy、MCF-7與WiDr等癌細胞具有些微細胞毒殺活性，其對以上細胞的ED50分別為10.32、14.52、16.82與17.16 μg/mL。

關鍵字

紅花八角 ； prenylated C6-C3化合物 ； 細胞毒殺測試 ； illicabrin A ； illicabrin B ； illicabrin C

並列摘要

This research focuses on prenylated C6-C3 compounds from the fruits of Illicium arborescens Hayata. The CH2Cl2 and EtOAc extracts of fruits were investigated by using chromatography to yield 12 compounds.
By using liquid chromatography, three new compounds named illicaborin A (1), illicaborin B (2), illicaborin C (3) were isolated, together with nine known compounds, 1-allyl-2,3-(methylenedioxy)-5-methoxybenzene (4), apiol (5), illicinone E (6), 11-epi-illilinone E (7), 2,3-dehydroillifunone C (8), illifunone A (9), illifunone B (10), illifunone C (11) and illifunone D (12)。
Compound 1 has a new skeleton which is analogous with prenylated C6-C3 skeleton, but compound 1 connects with an additional CH2OH group at C-2 position. The new compound 2 possesses a prenylated C6-C3 skeleton, and compound 3 is a new phytoquinoid. All structures of the above compounds were elucidated by means of 1D, 2D-NMR spectroscopic analysis and physical methods including IR, mass, UV, and optical rotation, and also by comparision with the published data. The relative configuration of compounds 1-3 was determined by NOESY experiment.
Cytotoxicity of compounds 1-3, 8, 11 was evaluated by Dr. Kuo’s lab. Compound 2 exhibited weak cytotoxicity against HEp-2, Daoy, MCF-7 and WiDr cell lines, as ED50 were 10.32, 14.52, 16.82 and 17.16 μg/mL, respectively.

並列關鍵字

Illicium arborescens Hayata ； prenylated C6-C3 ； cytotoxicity ； illicabrin A ； illicabrin B ； illicabrin C

參考文獻

1. Isao, K., Naosuke, B., Miwa, H., Nobusuke, K., Masakatsu, T., Hiroshi, K., Chun, S. Y., & Sadao, S. (1989). Isolation of three new sesquiterpene lactones from the pericarps of Illicium majus. Chem. Pharm. Bull., 37(9), 2448-2451.

2. Chun, S. Y., Miwa, H., Naosuke, B., Masakatsu, T., Hiroshi, K., Nobusuke, K., & Isao, K. (1990). A new toxic neoanisatin derivative from the pericarps of Illicium majus. Chem. Pharm. Bull., 38(1), 291-292.

3. Emi, O., Tomonori, N., & Miko, Y. (1993). Convulsants from star anise (Illicium verum HOOK.F.). Chem. Pharm. Bull., 41(9), 1670-1671.

4. Yoshiyasu, F., Naomi, S., & Mitusaki, K. (1993). Isodunnianin: a new sesquiterpene enhancing neurite outgrowth in primary culture of fetal rat cerebral hemisphere from Illicium tashiroi. Planta Med., 59, 181-182.

5. Jian, M. H., Ritsuko, Y., Chun-shu, Y., & Yoshiyasu, F. (2000). Merrilactone A, a novel neurotrophic sesquterpene dilactone from Illicium merrillianum. Tetrahedron Lett., 41, 6111-6114.