山枇杷 (Eriobotrya deflexa (Hemsl.) Nakai) 薔薇科 (Rosaceae)枇杷屬 (Eriobotrya) 常綠喬木,為台灣特有種植物,分布於台灣全島低、中海拔闊葉林中。本論文乃將山枇杷葉以 95% 乙醇萃取,分別以正己烷、乙酸乙酯、正丁醇及水進行部份劃分,其中乙酸乙酯層及正丁醇層萃取物,經由各種管柱層析方法進行分離純化,於乙酸乙酯層得到 5 個化合物,正丁醇層得到 8 個化合物,經理化及光譜相關數據與參考文獻比對後,確認構造為 7 個 flavonol glycosides 化合物:(1)、(2)、(3)、(4)、(5)、(6) 及 (9) ﹔1 個 flavone 化合物:(10) ﹔以及 2 個 caffeoyl 衍生之化合物:(7) 及 (8),其中有 3 個 flavonol glycosides 化合物:(3)、(5) 及 (8) 同時存在於兩層萃取物中。進而以高效液相層析-固相萃取-核磁共振 (LC-SPE-NMR) 進行分析,於乙酸乙酯層分析出含有 5 個 flavonol glycosides:(2)、(3)、(5)、(6)和 (9) 以及 5 個含有 p-coumaryl 基團化合物 ﹔於正丁醇層經管柱層析前處理,分析出含有 1 個 flavonol glycosides 化合物:(9)、1 個 caffeoyl 衍生之化合物、2 個含有 p-coumaryl 基團 及 2 個含有 caffeoyl 基團的化合物。進而以人類皮膚纖維母細胞,經紫外線 B 照射來誘導細胞大量分泌基質金屬蛋白酶 (MMPs),利用 MMP-1 做為抗光老化活性指標。結果顯示:在低細胞毒性下,化合物 (1)、(2)、(5) 及 (7) 於 100 μM 時,具有較明顯之抑制作用。
Eriobotrya deflexa (Hemsl.) Nakai (Rosaceae) is an evergreen tree and endemic throughout of Taiwan. The leaves of E. deflexa were extracted with 95% ethanol, then partitioned with a sequence of n-hexane, ethyl acetate (EtOAc), and n-butanol (n-BuOH). The EtOAc layer and n-BuOH layer were passed by a series of chromatographic analysis, isolated, and purified. The structures of isolated compounds were identified by various physical and spectroscopic characterizations. There were five compounds obtained from the EtOAc layer and eight compounds from the n-BuOH layer, but three compounds were in both layers at the same time. Totally, ten compounds were obtained from E. deflexa, including seven flavonol glycosides: (1), (2), (3), (4), (5), (6), (9), one flavone: (10), and two caffeoyl derivatives: (7), (8) in the present study. By using high-performance liquid chromatography with postcolumn solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR) to analyse the constituents of EtOAc layer and fraction 3 of n-BuOH layer from E. deflexa. There were five flavonol glycosides: (2), (3), (5), (6), (9) and five compounds with p-coumaryl group in EtOAc layer, and there are one flavonol glycoside: (9), one caffeoyl derivative, two compounds with p-coumaryl group and two compounds with caffeoyl group in fraction 3 of n-BuOH layer with LC-SPE-NMR analysis. The isolated compounds were evaluated the anti-photoaging activity using MMP-1 as a target on the production of MMP-1 secretions after XV UVB irradiation in WS-1. The results showed that compounds (1), (2), (5) and (7) (100 μM) exhibited the MMP-1 inhibitory effects at low cytotoxicity in WS-1 cells.