文旦柚樹之成分研究—莖皮成分、Imperatorin之生物轉化及果皮中香豆精與氮營養之關係

Study on the Constituents of the Buntan—Constituents of Stem Bark, Biotransformation of Imperatorin, and Relationship between Coumarin Concentrations in Fruit Peel and Nitrogen Fertilizer

鄧雯玉(Wen-Yuh Teng)

指導教授 ： 鍾仁賜

國立臺灣大學/生物資源暨農學院/農業化學研究所/博士(2005年)

https://doi.org/10.6342/NTU.2005.00776

摘要

柚 (C. maxima Merr.) 在台灣種植的面積相當廣，年有6,336公頃，年產量達74,480公噸。柚樹莖皮與果皮中含有許多活性成分，但栽培條件及季節變化對文旦柚組織中香豆精類化合物的組成及量變化有更多研究之必要，故本試驗的目的為 (一) 針對柚樹莖皮高極性劃分進行系列分離純化，以光譜法鑑定其結構，並探討其活性；(二) 探討氮肥用量對文旦柚果在不同生長期，其外果皮中香豆精化合物之影響；(三) 不同溫度與壓力之二氧化碳超臨界流體搭配助溶劑萃取柚皮，配合高效能液相層析儀，探討各萃取條件對香豆精類化合物萃取效率的影響；(四) 探討香豆精類化合物是否可藉由生物轉化，形成其他具有生物活性之成分，而增加其用途。

結果顯示，由柚樹莖皮之水層高極性劃分進行系列地分離純化，共可得到10個純化合物，其中包括一個新化合物，5-hydroxynoracronycine alcohol，三個已知limonin-type terpenoids：obacunone、nomilin、limonin及六個已知acridone生物鹼：glycocitrine-I、5-hydroxynoracronycine、citrusinine-I、grandisine-I、natsucitrine-II、citracridone-III。將純化物質進行癌細胞之細胞毒檢定，發現受試化合物對HepG2及KB癌細胞均有抑制活性。不同量氮肥在不同生長期影響外果皮組織中香豆精化合物之試驗顯示，雖然最高量氮處理之香豆精在單顆果皮中之含量有較高的趨勢，但由於生物體本身變異大，以致差異不顯著，因此無法判斷其含量是否提高；然而，不同採收期之各香豆精含量差異明顯，涵示香豆精類化合物之合成量及代謝過程與作物本身之發育相關；在各生長期，氮肥的影響性較小。在50

關鍵字

香豆精類 ； 文旦柚 ； 果皮 ； 生物轉化 ； 莖皮

並列摘要

Buntan (Citrus maxima Merr.) is a popular seasonal fruit. The annual planting area is about 6,336 ha and the fruit harvest is about 74,480 tons in Taiwan. Many kinds of secondary product with biological activities from the stem bark and fruit peel of buntan have been studied, but the effects of the cultivation conditions and seasonal variations on the composition and the contents of secondary products in buntan peel tissues need more study. The purposes of this research are to study (1) isolation and identification of the pure compounds from the higher polar fractionation in the stem bark of buntan, and to examine their cytotoxic effects on several types of cancer cell lines; (2) the effect of application rates of nitrogen fertilizer on the growth of fruits of buntan and the concentration of coumarins in the outer fruit peel of buntan; (3) the efficiency of the extraction of coumarins from the fruit peel of buntan by supercritical carbon dioxide fluid (SF-CO2) under various conditions, i.e., difference of temperature, pressure, and accompanied with entrainers; (4) the possibility of biotransformation of imperatorin by fungi, and to assess the biological activities of the transformed metabolites.

The results indicated that after the concentrated methanolic extract of the stem bark of buntan being treated with water, a new acridone alkaloid, 5-hydroxynoracronycine alcohol, along with three known limonin-type terpenoids: obacunone, nomilin, and limonin, and six known acridone alkaloids: glycocitrine-I, 5-hydroxynoracronycine, citrusinine-I, grandisine-I, natsucitrine-II, and citracridone-III were identified. All test compounds were found to be cytotoxic on HepG2 and KB tumor cell lines. In coumarins research, the content of coumarins in fruit peels of the highest application rate of nitrogen fertilizer was the higher, however there was no significant difference among treatments. However, there was a seasonal variation in the production of coumarins. This implies that the production of coumarins is development reflected. The efficiency of extraction of coumarins by SF-CO2 under 50

並列關鍵字

biotransformation ； coumarins ； fruit peel ； stem bark ； buntan

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