南仁新木薑子葉部化學成分及抗發炎活性之研究

Chemical Constituents and Anti-inflammatory Activity from the Leaves of Neolitsea hiiranensis

劉碧娟(Bi-Jiuan Liou)

指導教授 ： 陳益昇

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2010年)

摘要

南仁新木薑子 (Neolitsea hiiranensis Liu & Liao) 屬於樟科 (Lauraceae)，為一常綠小喬木或灌木，只分布於南仁山及恆春半島，為台灣固有種。李文雄 教授曾由其根部分離出12個化合物，主要為倍半萜類之linderane、linderalactone、pseudoneolinderane、(+)-linderadine、pseudoneoliacine、isolinderalactone、deoxysericealactone、sericealactone及cryptomeridol。然而，過去並未有關於本植物之生物活性研究。
針對台灣產40餘種樟科植物以iNOS assay方式進行抗發炎活性篩選，發現N. hiiranensis葉部之甲醇萃取物具有抑制NO產生的能力而不具RAW 264.7細胞毒殺性；此外，尚未有關於葉部之成分研究。因此，本實驗目的為針對南仁新木薑子之葉部進行化學及抗發炎活性成分之探討。
由乙酸乙酯可溶部具抗發炎活性層利用活性導向分割法分離出七個新的倍半萜類化合物：hiiranlactones A~D (1-4)、hiiraneudesmol (5)、hiirandilactone (6)、hiiranepoxide (7)，一個新的三萜類化合物：hiiranterpenone (8)，以及22個已知化合物：(－)-ent-4β-hydroxy-10α-methoxyaromadendrane (9)、4β,10α-dihydroxyaromadendrane (10)、pipelol A (11)、kobusone (12)、caryolane-1,9β-diol (13)、trans-phytol (14)、132-hydroxy-(132-S)-pheophytin a (15)、α-tocopheryl quinone (16)、α-tocopherol (17)、ficaprenol-11 (18)、linolenic acid (19)、syringaldehyde (20)、syringic acid (21)、de-O-methyl-sericealactone (71)、pseudoneoliacine (88)、neoliacinolide A (89)、spathulenol (103)、(6α,7α)-4β-hydroxy-10α-methoxyaromadendrane (106)、β-caryophyllene oxide (109)、β-sitosterol (185)、vanillin (206)及p-anisic acid (208)。以上化合物皆以各種圖譜分析來決定結構。
Spathulenol (103)及(6α,7α)-4β-hydroxy-10α-methoxyaromadendrane (106)具有微弱抑制NO產生的能力。

關鍵字

南仁新木薑子 ； 樟科 ； 葉部 ； 倍半萜三萜類 ； 抗發炎活性

並列摘要

Neolitsea hiiranensis Liu & Liao (Lauraceae) is a small evergreen tree or shrub, endemic to Taiwan, distributed only from Nanjenshan and Hengchun Peninsula. Twelve known compounds, mainly sesquiterpenoids, were previously isolated by Li et al. from the root of this plant, such as linderane, linderalactone, pseudoneolinderane, (+)-linderadine, pseudoneoliacine, isolinderalactone, deoxysericealactone, sericealactone, and cryptomeridol. However, the biological activity of this species has not been conducted.
Recently, over 40 species of Formosan Lauraceous plants have been screened for anti-inflammatory activity using an inducible nitric oxide synthase (iNOS) assay, and the methanolic extract of the leaves of this species has been shown with potent inhibition of NO production without any cytotoxicity against RAW 264.7 cells. Besides, the chemical constituents of its leaves have never been studied. The aim of this study is the isolation of chemical constituents and their iNOS inhibitory activities.
Bioassay-guided fractionation of the ethyl acetate soluble layer of the leaves of this species led to the isolation of seven new sesquiterpenoids: hiiranlactones A-D (1-4), hiiraneudesmol (5), hiirandilactone (6), and hiiranepoxide (7), one new triterpenoid: hiiranterpenone (8), along with 22 known compounds: (－)-ent-4β-hydroxy-10α-methoxyaromadendrane (9), 4β,10α-dihydroxyaromadendrane (10), pipelol A (11), kobusone (12), caryolane-1,9β-diol (13), trans-phytol (14), 132- hydroxy-(132-S)-pheophytin a (15), α-tocopheryl quinone (16), α-tocopherol (17), ficaprenol-11 (18), linolenic acid (19), syringaldehyde (20), syringic acid (21), de-O-methylsericealactone (71), pseudoneoliacine (88), neoliacinolide A (89), spathulenol (103), (6α,7α)-4β-hydroxy-10α-methoxyaromadendrane (106), β-caryo- phyllene oxide (109), β-sitosterol (185), vanillin (206), and p-anisic acid (208). The structures of these isolates were elucidated by spectroscopic analysis.
Spathulenol (103) and (6α,7α)-4β-hydroxy-10α-methoxyaromadendrane (106) showed weak inhibitory activity of NO production.

並列關鍵字

Neoitsea hiiranensis ； Lauraceae ； leaves ； sesquiterpenoid ； triterpenoid ； anti-inflammatory activity

參考文獻

1. Liao JC. Lauraceae in Flora of Taiwan. Editorial

Committee of the Flora of Taiwan; Taipei 1998; Vol.Ⅱ, pp 433-99.

2. Yang YP, Liu HY, Lu SY. Manual of Taiwan Vascular Plants. 2nd ed. The Council of Agricultre, the Executive Yuan 1999; Vol.Ⅱ, pp 141-4.

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4. Feldverg W. The role of mediators in the inflammatory tissue response. Int Arch Allergy Appl Immunol 1956; 8: 15-31.