烏皮九芎根部化學成分與抗氧化活性之研究

Chemical constituents and their antioxidant activity from the root of Styrax formosana

楊佳蓉(Chia-Jung Yang)

指導教授 ： 張訓碩

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2015年)

摘要

烏皮九芎 (Styrax formosana Matsum.)屬於安息香科之落葉性灌木或小喬木，為台灣固有種植物。分布於台灣本島的低,中海拔(0-2,000 m)的森林中。針對近1,400種台灣產之植物進行活性篩選，發現烏皮九芎根部具有清除DPPH自由基和ABTS陽離子自由基的活性，過去只有一篇研究指出烏皮九芎葉部的乙醇萃取物具有良好的抗氧化活性，但其有效活性成分仍尚未有人從事研究。因此，本研究之目的為針對烏皮九芎根部進行化學成分及生物活性之探討。
利用活性導向試驗，從烏皮九芎根部正丁醇層萃取物分離得到30個化合物，其中有三個新的lignan類化合物，分別為styraxinol (93)、styraxinone (94)、(–)-lariciresinol-4'-monomethyl ether (97)，以及27個已知的化合物，包含18個 lignan 類化合物，5個triterpenoid類化合物，3個steroid 類化合物和1個sesquiterpenes 類化合物，1個benzenoid類化合物。以上化合物以各種圖譜分析來決定結構。生物活性試驗中，erythro-1-(4'-hydroxy-3'-methoxyphenyl)-2-[4'-(3-hydroxypropyl)-2',6'-dimethoxyphenoxy]propane-1,3-diol (95)，(–)-lariciresinol-4'-monomethyl ether (97)，(+)-syringaresinol (104)，(–)-medioresinol (106)，secoisolariciresinol (113)具有清除ABTS自由基的能力，其SC50值在20 分鐘內分別為28.6, 31.4, 15.8, 18.9, 4.4 μM。(+)-matairesinol (56)，(–)-lariciresinol-4'-monomethyl ether (97)，(+)-syringaresinol (104)，(–)-medioresinol (106)，secoisolariciresinol (113)具有清除DPPH自由基的能力，SC50值在30 分鐘內為18.5, 8.2, 14.0, 14.0, 14.2 μM。其中(+)-syringaresinol (104)，(–)-medioresinol (106)，secoisolariciresinol (113)具有比positive control有更好的自由基清除的能力，無論在ABTS或DPPH上。

關鍵字

烏皮九芎 ； 安息香科 ； 根部 ； 木質素 ； 抗氧化

並列摘要

Styrax formosana Matsum. (Styracaceae) is a shrub or small tree, endemic to Taiwan and grows in low to medium altitudes forest about 0-2,000 m throughout Taiwan Island. Approximately over 1,400 species of Formosan plants have been screened for biological activities. The methanolic extract of the root of this plant showed free radical scavenging activities. In the past, only one paper reported the leaves’ extract of this plant showing free radical scavenging activities, and its chemical constituents have not been studied. Therefore, the aim of this study is the isolation of chemical constituents and the evaluation of their biological activities.
Firstly, bioassay-guided fractionation of active n-BuOH layer from the root of this species led to the isolation of 3 new lignanoids, styraxinol (93), styraxinone (94), and (–)-lariciresinol-4'-monomethyl ether (97), along with 27 known compounds including 17 lignans, five triterpenoids, three steroids, one sesquiterpene, and one benzenoid。Among these isolates, erythro-1-(4'-hydroxy-3'-methoxyphenyl)-2-[4'-(3-
hydroxypropyl)-2',6'-dimethoxyphenoxy]propane-1,3-diol (95), (–)-lariciresinol-4'-monomethyl ether (97), (+)-syringaresinol (104), (–)-medioresinol (106), secoisolariciresinol (113) showed ABTS cation radical scavenging activity, with SC50 values of, and 28.6, 31.4, 15.8, 18.9, and 4.4 μM in 20 minute, respectively. In addition, (+)-matairesinol (56), (–)-lariciresinol-4'-monomethyl ether (97), (+)-syringaresinol (104), (–)-medioresinol (106), secoisolariciresinol (113) showed potent DPPH radical scavenging activity, with SC50 values of 18.5, 8.2, 14.0, 14.0, and 14.2 μM in 30 minute, respectively. (+)-syringaresinol (104), (–)-medioresinol (106), secoisolariciresinol (113) had stronger scavenging activity than positive control in both of ABTS and DPPH assays.

並列關鍵字

Styrax formosana ； Styracaceae ； Root ； Lignan ； Antioxidant activity

參考文獻

1.Li HL. Styracaceae in Flora of Taiwan, 2nd ed. Editorial Committe of the Flora of Taiwan. Taipei, Taiwan, 1998; Vol. IV: pp. 95-100. Styracaceae, in Flora of Taiwan, 2nd edn. Editorial Committe of the Flora of Taiwan. Taipei, Taiwan, 1998; Vol. IV: pp. 95.

2.Harman D. Aging: A theory based on free radical and radiation chemistry. J Gerontol 1956; 11: 298-300.

3.Alessio HM, Goldfarb AH. Lipid peroxidation and scavenger enzymes during exercise: Adaptive response to training. J Appl Physiol 1988; 64: 1333-6.

4.Jiang CB, Chang MJ, Wen CL, Lin YP, Hsu FL, Lee MH. Natural products of cosmetics: Analysis of extracts of plants endemic to Taiwan for the presence of tyrosinase-inhibitory, melanin-reducing, and free radical scavenging activities. J Food Drug Anal 2006; 14: 346-52.

5.Ulubelen A, Goren N. Preliminary investigations on the herba of Styrax officinalis. Planta Med 1973; 24: 290-3.