薄葉山礬葉部化學成分及抗結核活性之研究

Chemical constituents and anti-tubercular activity from the leaves of Symplocos anomala

10.6832/KMU.2014.00158

黃政議

薄葉山礬 ； 灰木科 ； 葉部 ； 萜類生物鹼糖苷類胡蘿蔔素氧化裂解化合物 ； Symplocos anomala ； Symplocaceae ； leaves ； terpene alkaloidal glucoside ； apocarotenoid

高雄醫學大學天然藥物研究所碩士班學位論文

2014年

碩士

陳益昇

繁體中文

薄葉山礬(Symplocos anomala Brand)隸屬於灰木科(Symplocaceae)，是一種 小喬木。分布於日本沖繩、東南亞、中國南部和台灣1。灰木屬為灰木科中唯一 的屬，曾於該屬中發現的化合物包含以下種類：saponins、triterpenoids、flavonoids、 lignans、phenols、alkaloids、sterols 和iridoids。於約1400 多種的台灣產之植物 針對抗結核分枝桿菌(Mycobacterium tuberculosis H37Rv)活性篩選中，薄葉山礬 葉部的甲醇萃取物有良好的抗結核活性，本植物未曾有過化學成分分離或生物活 性之研究，故本研究之目的為進行薄葉山礬葉部的化學成分分離以及生物活性之 探討。 經由活性導向分劃，由薄葉山礬葉部之乙酸乙酯可溶層中，分離出30 個已 知的化合物，其中包含：三個alkaloids：vincoside lactam (116)、naucleaorine (117) 和1,2,3,4-tetrahydro-1-oxo-β-carboline (134)，四個apocarotenoids：tectoionol A (118)、linarionoside B (119)、blumenol B (120)和(+)-3-oxo-α-ionone (121)，兩個 triterpenoids ： asiatic acid (3) 和jacoumaric acid (122) ，一個iridoid ： 4-epialyxialactone (123) ，兩個benzenoids：syringaldehyde (124)和salidroside (125) ， 兩個phenylpropanoids：trans-ferulic acid (126)和trans-methyl ferulate (127) ，一 個coumarin： isoscopoletin (128) ，六個lignans：(+)-sesamin (129)、(±)-pinoresinol (84)、(±)-syringaresinol (130)、(+)-1-acetoxypinoresinol 4'-O-methyl ether (131)、 (+)-lariciresinol (132)和(＋)-lariciresinol 9-O-β-D-glucopyranoside (133) ，兩個 chlorophylls：pheophytin-a (135)和151-hydroxypurpurin-7-lactone dimethyl ester (136) ，三個 steroids：β-sitosterol (109) and stigmasterol (111)之混合物以及 α-spinasterol (137)，四個fatty acid 及derivatives：(11S,12S,13S)-(9Z,15Z)-11- hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid (138)、methyl palmitate (139) and methyl oleate (140)之混合物和(Z)-3-hexenyl-β-D-glucopyranoside (141)。

Symplocos anomala Brand (Symplocaceae) is a small tree. It distributes at Okinawa, Southeast Asia, Southern China, and Taiwan. Saponins, triterpenoids, flavonoids, lignans, phenols, alkaloids, sterols, and iridoids are widely occurred in Symplocos, which is the only genus in Symplocaceae. Approximately about 1,400 species of Formosan plants have been screened for anti-tubercular activity against Mycobacterium tuberculosis H37Rv in vitro. The methanolic extract of the leaves of this plant showed significant anti-tubercular activity in vitro. The chemical constituents and their bioactivities of this species have never been conducted. Bioassay-guided fractionation of active ethyl acetate-soluble layer from the leaves of this species led to the isolation of 30 known compounds, including three alkaloids: vincoside lactam (116), naucleaorine (117), and 1,2,3,4-tetrahydro-1-oxo-β- carboline (134), four apocarotenoids: tectoionol A (118), linarionoside B (119), blumenol B (120), and (+)-3-oxo-α-ionone (121), two triterpenoids: asiatic acid (3) and jacoumaric acid (122), one iridoid: 4-epi-alyxialactone (123), two benzenoids: syringaldehyde (124) and salidroside (125), two phenylpropanoids: trans-ferulic acid (126) and trans-methyl ferulate (127), one coumarin: isoscopoletin (128), five lignans: (+)-sesamin (129), (±)-pinoresinol (84), (±)-syringaresinol (130), (+)-1-acetoxypinoresinol 4'-O-methyl ether (131), (+)-lariciresinol (132), and (＋)-lariciresinol 9-O-β- D-glucopyranoside (133), two chlorophylls: pheophytin-a (135) and 151-hydroxypurpurin- 7-lactone dimethyl ester (136), three steroids: a mixture of β-sitosterol (109) and stigmasterol (111), α-spinasterol (137), four fatty acid and derivatives: (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid (138), a mixture of methyl palmitate (139) and methyl oleate (140) and (Z)-3-hexenyl-β-Dglucopyranoside (141).