阿里山五味子藤莖活性木酚素成分之研究

Studies on the Bioactive Lignans from stems of Schisandra arisanensis Hayata

李沛心(Pei-Hsin Li)

指導教授 ： 沈雅敬

國立臺灣大學/醫學院/藥學研究所/碩士(2018年)

https://doi.org/10.6342/NTU201803850

摘要

本論文研究台灣特有種阿里山五味子 (Schisandra arisanensis Hayata)藤莖的乙醇萃取物，並分析鑑定其所含之木酚素成分。共分離出二十一個成分，包含十九個木酚素與兩個倍半萜類。
本實驗得到之成分中有三個新成分1-3，其中化合物1和3為木酚素，二者各有C18 dibenzocyclooctadiene和dihydrobenzofuran的骨架，一個倍半萜類化合物2。此次分離到的已知倍半萜為2-hydoxy-11, 12-dehydrocalamenene (4)，十七個已知木酚素成分有：isoanwulignan (5)、methylgomisin R (6)、interiotherin B (7)、schisantherin D (8)、3',4'-dimethoxybenzoic acid (3',4'-dimethoxyphenyl)-2-methyl-3-oxobutyl ester (9)、gomisin G (10)、12-demethylwuweilignan I (11)、arisanschinin E (12)、(+)-fragransin A2 (13)、(+)-verrucosin (14)、gomisin J (15)、machilin D (16)、rubrisandrin A (17)、gomisin E (18)、kadsuphilin B (19)、arisanschinin F (20)、dihydrodehydrodiconiferyl alcohol (21)。
新成分和已知成分經過一維和二維核磁共振圖譜 (COSY, HMQC, HMBC, NOESY)、紅外線、紫外線線、圓二色性光譜、高解析電灑式質譜以及旋光值之測定，參閱Reaxys電子資料庫相似化合物和Web of Science之文獻後建立化學結構。
將所得的化合物 (1–21)進行抗發炎、抗癌細胞與抗氧化活性測試與評估。

關鍵字

阿里山五味子 ； 藤莖 ； 木酚素 ； 倍半?

並列摘要

This thesis focused on the investigation of an ethanol extract from stems of Schisandra arisanensis Hayata, an endemic species in Taiwan. Fractionation of the extract has resulted in the isolation of twenty-one compounds, including nineteen lignans and two sesquiterpenes.
Three new compounds (1-3) containing a dibenzocyclo-octadiene lignan with a C18 skeleton, a sesquiterpenoid, and a dihydrobenzofuran 8,3'-lignan were reported here. Others were known compounds, including 2-hydoxy-11, 12-dehydrocalamenene (4), isoanwulignan (5), methylgomisin R (6), interiotherin B (7), schisantherin D (8),3',4'-dimethoxybenzoic acid (3',4'-dimethoxyphenyl)-2-methyl-3-oxobutyl ester (9), gomisin G (10), 12-demethylwuweilignan I (11), arisanschinin E (12), (+)-fragransin A2 (13), (+)-verrucosin (14), gomisin J (15), machilin D (16), rubrisandrin A (17), gomisin E (18), kadsuphilin B (19), arisanschinin F (20), dihydrodehydrodiconiferyl alcohol (21).
The structures of these new compounds were established on the basis of spectroscopic methods, especially 2D NMR (COSY, HMQC, HMBC, NOESY), and high-resolution ESI-MS, infrared, ultraviolet, CD, and specific optical rotation. In addition, searching for the related compound in Reaxys database and reference reports from Web of Science were necessary to elucidate the structures.
All anti-inflammatory bioactivities, anti-tumor cytotoxicities, and anti-oxidation activities of the compounds were tested and evaluated.

並列關鍵字

Schisandra arisanensis ； stems ； lignans ； sesquiterpenes

參考文獻

1. A. Szopa; R. Ekiert; H. Ekiert. Current knowledge of Schisandra chinensis (Turcz.) Baill. (Chinese magnolia vine) as a medicinal plant species: a review on the bioactive components, pharmacological properties, analytical and biotechnological studies. Phytochemistry reviews, 2017, 16, 195–218.

2. F. Li; T. Zhang; H. Sun; H. Gu; H. Wang; X. Su; C. Li; B. Li; R. Chen; J. Kang. A New Nortriterpenoid, a Sesquiterpene and Hepatoprotective Lignans Isolated from the Fruit of Schisandra chinensis. Molecules, 2017, 22, 1931.

3. H. T. Liu; L. J. Xu; Y. Peng; J. S. Yang; X. W. Yang; P. G. Xiao. Complete assignments of H-1 and C-13 NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia. Magnetic Resonance in Chemistry, 2009, 47, 609–612.

4. 國立台灣大學植物標本館(2012)。台灣植物資訊整合查詢系統。取自http://tai2.ntu.edu.tw/PlantInfo/family.php?family=Schisandraceae

5. A. Panossian; G. Wikman. Pharmacology of Schisandra chinensis Bail.: An overview of Russian research and uses in medicine. Journal of Ethnopharmacology, 2008, 118, 183–212.