灰莉枝葉之成分研究

Studies on the Chemical Constituents from the Leaves and Twigs of Fagraea ceilanica Thunb.

黃鈞傳(Kuan-Chun Wong)

指導教授 ： 沈雅敬

共同指導教授 ： 顧記華(Jih-Hwa Guh)

國立臺灣大學/醫學院/藥學研究所/碩士(2019年)

https://doi.org/10.6342/NTU201901319

摘要

本論文主要研究灰莉 (Fagraea ceilanica Thunb.) 含有之天然物活性成分，其枝葉以酒精萃取，然後使用各類管柱色層分析進行分離，並以核磁共振等方法鑑定化學結構。實驗結果共得八個新seco-iridoid類化合物1−8，其中包含具有五碳鍊的新骨架化合物 1−3；具有furanone的化合物4和5，以及立體結構不同的化合物6−8。此外還有六個已知化合物，分別為djalonenol (9) 12、swertiachiralatone A (10) 13、(-)-boonein (11) 15、epiloliolide (12) 16、(S)-dehydro-vomifoliol (13) 17、floribundane B (14) 18。

所有化合物之結構解析皆利用核磁共振圖譜1D-NMR (1H-NMR、13C-NMR、DEPT-135、DEPT-90) 及2D-NMR (HSQC、COSY、HMBC、NOESY) 和所得之物理數據，包括高解析電灑式質諎儀、紅外線吸收光譜、紫外線吸收光譜、圓二色光譜和比旋光度而建立，最後利用化學結構資料庫 Reaxys 和 SciFinder以及相關文獻加以比對。部分分離所得之化合物已送測非小細胞性肺癌細胞毒殺以及IL-6釋放抗發炎生物活性測試，然而皆沒有抑制效果。

關鍵字

灰莉 ； seco-iridoid ； 細胞毒殺 ； 抗發炎

並列摘要

This study focuses on the natural products discovery of the ethanol extract from the leaves and twigs of Fagraea ceilanica Thunb. Several types of column chromatography have been used to isolate and got eight new seco-iridoids 1−8, included three new skeleton compounds 1−3 with five-carbon chain structure. Compounds 4 and 5 have furanone and compounds 6−8 are different in the configuration. Otherwise, six known compounds djalonenol (9) 12, swertiachiralatone A (10) 13, (-)-boonein (11) 15, epiloliolide (12) 16, (S)-dehydro-vomifoliol (13) 17, and floribundane B (14) 18 were found.
All the structures were educated and confirmed on the basis of various spectroscopic analysis, including 1D-NMR (1H-NMR, 13C-NMR, DEPT-135 and DEPT-90) and 2D-NMR (HSQC, COSY, HMBC and NOESY). High resolution electrospray ionization mass spectrometry (HRESIMS), ultraviolet spectroscopy (UV), infrared spectroscopy (IR), electronic circular dichroism (ECD) and specific rotation. After that, the compounds were compared with the internet chemical database, Reaxys, SciFinder and other interrelated papers. Some of the isolated compounds were tested for non-small cell lung cancer cytotoxic and IL-6 release anti-inflammatory activities. Unfortunately, all of those compounds did not present inhibitory effect.

並列關鍵字

Fagraea ceilanica Thunb. ； seco-iridoids ； cytotoxicity ； anti-inflammation

參考文獻

1. D. J. Newman; G. M. Cragg; K. M. Snader. The influence of natural products upon drug discovery. Nat. Prod. Rep. 2000, 17, 215−234.

2. A+線上醫學百科—五十二病方 (2019.06.20)

3. 維基百科—本草綱目 (2019.06.20)

4. G. M. Cragg; P. G. Grothaus; D. J. Newman. New horizons for old drugs and drug leads. J. Nat. Prod. 2014, 77, 703−723.

5. L. Struwe; V. A. Albert. Gentianaceae systematics and natural history. 2002, first publishing.