紅果椌木枝葉與根部雙萜類成分之研究

Abstract

在活性篩選時發現紅果椌木枝葉之乙醇萃取物具有抗發炎效果，根部之乙醇萃取物則有抗人類癌細胞之效用。因此本論文主要研究其所含有的化學結構和其生物活性，又鑑於蔡耀慶學長已從一部份枝葉之乙醇萃取物中分離出一些有活性之雙萜類化合物，因而將重點著重於有活性之雙萜類尋找。所用之方法即利用各式管柱色層分析方法進行分離並鑑定其所含之化學成分。 實驗結果共分離出10個化合物，共有3個屬於labdane骨架的雙萜類新化合物1-3，4個屬於prenyleudesmane骨架的雙萜類新化合物4-7，以及3個已知化合物 (－)-3β-hydroxy-15,16-dinorlabd-8(17)-ene-13-one (8)、dysokusones A (9)、4,5-epoxy-β-caryophyllene (10)。 以上分離獲得之化合物利用核磁共振圖譜1D NMR (1H-NMR、13C-NMR)及2D NMR (HSQC、HMBC、COSY、NOESY)，並加上各種物理方法; 如比旋光度、紫外線光譜、圓二色性光譜及高解析電灑式質譜，以及利用化學資料庫Reaxys查詢相關文獻以鑑定結構。最後將所獲得之化合物進行抗發炎、抗癌與抗病毒等生物活性檢測。 關鍵字：紅果椌木、雙萜類、倍半萜類、抗發炎與抗癌細胞活性

In preliminary bioactive screening, the ethanolic extract of leaves and twigs from Dysoxylum hongkongense exhibited significant anti-inflammatory activities while the extract of roots exhibited cytotoxicity against human cancer cells. On the other hand, our lab member, Yao-Ching Tsai has previously separated some bioactive diterpenoids from ethanolic extract of leaves and twigs. Thus this thesis mainly focuses on finding more bioactive diterpenoids from the twigs, leaves and roots of Dysoxylum hongkongense. A variety of chromatographic methods were used to fractionate and separate and finally got ten compounds. Among them, compounds 1-3 are new diterpenes of labdane-type and compounds 4-7 belong to new diterpenes of the prenyleudesmane type. In addition, compounds 8-10 are known compounds, (－)-3β-hydroxy-15,16-dinorlabd-8(17)-ene-13-one, dysokusones A and 4,5-epoxy-β-caryophyllene. The above structures were elucidated on the basis of spectroscopic analysis such as 1D NMR (1H-NMR、13C-NMR), 2D NMR (HSQC、HMBC、COSY、NOESY) techniques and physical methods including optical rotation, ultraviolet spectroscopy (UV), circular dichroism spectroscopy (CD) and high resolution mass spectroscopy (HRMS). Besides, the data of all compounds were compared with the published literatures by searching the chemical database of REAXYS. Finally, these compounds have been tested and evaluated their biological activities including anti-inflammatory, cytotoxic and anti-viral effects. Keywords: Dysoxylum hongkongense、diterpenoids、sesquiterpenoids、labdanes、prenyleudesmanes、anti-inflammatory、cytotoxic activities