大葉桃花心木種子化學成分及生物活性之研究

Studies on the Chemical Constituents and Bioactivities from the Seeds of Swietenia macrophylla

簡怡亭(Yi-Ting Chien)

指導教授 ： 鄭源斌

共同指導教授 ： 吳永昌(Yang-Chang Wu)

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2014年)

摘要

大葉桃花心木 (S. macrophylla) 是楝科 (Meliaceae) 桃花心木屬(Swietenia)之常綠喬木，原產於熱帶中南美洲，並廣泛分布於墨西哥至巴西東部的大西洋沿岸。大葉桃花心木除本身可作為高貴木材來源使用外，在馬來西亞、印度和東南亞國家其種子在民間用於治療癰疽膿皰、高血壓、糖尿病等疾病。
本研究將大葉桃花心木種子經由乙醇萃取，經一系列管柱層析純化之後，32個化合物被分離出來，其中包括四種檸檬苦素 (limonoids) 類型化合物。此分離之化合物均經光譜分析及質譜資料確定其結構，其中有7個新化合物，分屬為D-seco phragmalin-type limonoids及mexicanolide type的limonoids。本研究成果也是首次發現一系列新的D-seco phragmalin-type limonoids具有C-1"的異構結構。
Limonoids類化合物是從四環三萜類 (tetracyclic triterpenes) 衍生而來，其具有多樣化的活性，例如拒(蟲)食、抗瘧疾、抗微生物和抗愛滋病。本研究對分離所得之化合物進行抗登革熱病毒、抗C型肝炎和抗發炎生物活性分析，結果發現主量化合物19表現良好的抗登革熱病毒活性，而化合物21具有抗發炎活性。以目前醫療發展現況來說並沒有任何有效的疫苗及藥物可預防及治療登革熱，因此，此研究發現認為大葉桃花心木具有潛在發展為抗登革熱用藥。

關鍵字

大葉桃花心木

並列摘要

Swietenia macrophylla King (Meliaceae) is an evergreen tree. It is a native species in the tropical regions, especially in Central and South America. This species distributes widely from Mexico to east part of Brazil. The plant was used to a lofty timber source for architecture; however, the seeds of S. macrophylla in Malaysia, India, and southeastern Asia countries have been regarded as one of folk medicine for treating ulcer pustules, hypertension, and hyperglycemia diseases.
In this current investigation, the seeds of S. macrophylla were extracted by ethanol. The chromatographic purification of S. macrophylla ethanolic extract led to isolation of 32 compounds, which can be classified into four classes of limonoids. The structures of all isolates were elucidated by 1D and 2D spectral and mass data. Among them, seven new limonoids with D-seco phragmalin-type and mexicanolide type skeletons were isolated for the first time. Interestingly, the D-seco phragmalin-type limonoids possessed a unusual α-oriented methoxy group at C-1" position.
Limonoids are derived from tetracyclic triterpenes and have several diverse bioactivities, such as anti-feedant, anti-malarial, anti-microbial, and anti-HIV activities. In this study, anti-dengue viral, anti-hepatitis C and anti-inflammatory activities of isolated compounds were evaluated. The results indicated the major compound 19 exhibited anti-dengue viral activity, and compound 21 showed anti-inflammatory activity. So far, no effective vaccines or drugs can prevent or treat dengue fever. This finding indicated their potential for future development of anti-dengue agents.

並列關鍵字

Swietenia macrophylla

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