台灣產植物石斑木與台灣欒樹化學成分及生物活性之研究

Chemical Constituents and Biological Activities from Formosan Plants, Rhaphiolepis indica var. tashiroi and Koelreuteria henryi

林居宏(Chu-Hung Lin)

指導教授 ： 陳益昇

高雄醫學大學/藥學院/藥學研究所/博士(2014年)

摘要

高雄醫學大學藥用植物學科室經三十餘年努力，致力於研究台灣原生或固有種植物化學成分及生物活性研究，目前已建立1400餘種台灣產植物萃取物，可提供抗發炎、抗氧化、細胞毒殺、anti-HIV、抗血小板凝集及抗結核等活性篩選。
根據篩選平台，發現台灣產石斑木根部之甲醇萃取物具有抗發炎活性。石斑木 (Rhaphiolepis indica (L.) Lindl. ex Ker var. tashiroi Hayata ex Matsum. & Hayata) 屬於薔薇科(Rosaceae)石斑木屬常綠小喬木或灌木，分佈於台灣全島低海拔地區。其化學成分及活性研究未完整，故進行本植物之化學及抗發炎活性成分研究。由石斑木根部乙酸乙酯層中共分離得到20個化合物：包含2個新biphenyls: 3-hydroxy-2?S,5-dimethoxybiphenyl (96) 與2?S,3-dihydroxy-5-methoxybiphenyl (97)、4個新dibenzofurans: 2-hydroxy-3,4,6-trimethoxydibenzofuran (99), 2-hydroxy-3,4,9-trimethoxydibenzofuran (100), 2-hydroxy-3,4,6,9-tetramethoxydibenzofuran (101) 與 1,2-methylenedioxy-3,4,6-
trimethoxydibenzofuran (102)、3個新三萜化合物 3??,5??-dihydroxyglutinol (105), 2??,3??-dihydroxyolean-11,13(18)-dien-28,19-olide (106)與2??,3??-dihydroxyolean-13(18)-en-
28-oic acid (107)，以及11個已知的化合物。化合物96, 97和101均對於N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced production of superoxide anion具有良好的抑制活性，IC50值分別為8.36, 2.04與7.61 ?嵱.
台灣欒樹 (Koelreuteria henryi Dummer) 屬於無患子科 (Sapindaceae) 植物，為台灣固有種的落葉喬木，分布在低海拔闊葉林。根據細胞毒活性篩選，發現台灣欒樹莖部與果實分別對於MCF-7 (乳癌細胞)，NCI-H460 (肺癌細胞) 及HepG2 (肝炎癌細胞) 三種人類癌細胞株之生長呈現良好抑制活性。分別由台灣欒樹莖部與果實的乙酸乙酯層中分離得到35個化合物：包含3個新的木質酚類化合物：keolreuterones A‒C (133‒135)。其化學成分的分離與細胞毒活性的研究持續地進行中。
兩種台灣產植物石斑木與台灣欒樹之化學成分與生物活性之研究成果可達到本土藥用植物之開發之目的且可作為植物化學分類學之參考。

關鍵字

石斑木 ； 台灣欒樹 ； 抗發炎活性 ； 細胞毒活性 ； 根部 ； 莖部 ； 果實

並列摘要

Over 1,400 species of Formosan plants were collected for biological assays in our lab. Their methanolic extracts were screened for anti-inflammatory, anti-oxidant, cytotoxic, anti-platelet, anti-HIV and anti-tubercular activities.
Rhaphiolepis indica (L.) Lindl. ex Ker var. tashiroi Hay. ex Matsum. & Hay. (Rosaceae) is an evergreen shrub or small tree, distributes at low altitudes of Taiwan. The methanolic extract of the root of this species showed anti-inflammatory activity using N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced production of superoxide anion, an inflammatory mediator produced by neutrophils in vitro. Investigation of the active EtOAc-soluble layer from this plant led to the isolation of 20 compounds, two biphenyls: 3-hydroxy-2?S,5-dimethoxybiphenyl (96), and 2?S,3-dihydroxy-5-methoxybiphenyl (97); four dibenzofurans: 2-hydroxy-3,4,6-trimethoxydibenzofuran (99), 2-hydroxy-3,4,9-trimethoxydi-
benzofuran (100), 2-hydroxy-3,4,6,9-tetramethoxydibenzofuran (101), and 1,2-methylenedi-
oxy-3,4,6-trimethoxydibenzofuran (102); three triterpenes: 3??,5??-dihydroxyglutinol (105), 2??,3??-dihydroxyolean-11,13(18)-dien-28,19-olide (106), and 2??,3??-dihydroxyolean-13(18)-
en-28-oic acid (107), along with 11 known compounds. Among these isolates, 96, 97, and 101 exhibited inhibitory effects on fMLP-induced superoxide production, with in vitro IC50 values of 8.36, 2.04, and 7.61 ?嵱, respectively.
Koelreuteria henryi Dummer (Sapindaceae) is a large endemic evergreen tree growing in Taiwan. The methanolic extract of the stem, and the fruits of this plant showed cytotoxicities against MCF-7, NCI-H460, and HepG2 cancer cell lines. Bioassay-guided fractionation of the active EtOAc-soluble layer from the stem and the fruits led to the isolation of 35 compounds, including three new lignans: keolreuterones A‒C (133‒135). The successive isolation of the chemical constituents and their cytotoxicity assay of this species are still in progress.
These research results will be helpful to the development of new therapeutic drugs from natural prouucts, providing valuable information to the chemotaxonomy, together with developing resources from the two species of Taiwan.

並列關鍵字

Rhaphiolepis indica var. tashiroi ； Koelreuteria henryi ； Anti-inflammatory ； Cytotoxicity ； Root ； Stem ； Fruit

參考文獻

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