蘭嶼肉桂莖材部化學及抗結核菌活性成分之研究

Chemical and Antitubercular Constituents from the Stem Wood of Cinnamomum kotoense

陳甫勣(Fu-Chi Chen)

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(2004年)

摘要

蘭嶼肉桂(Cinnamomum kotoense)為蘭嶼產的常綠小喬木，屬固有種，近來因作為觀賞盆栽之用而引進台灣島內，而其化學成分與生物活性尚未被研究過，在本科室經過一系列地篩選具抗結核菌活性之台灣植物，發現蘭嶼肉桂莖材部之甲醇抽出物具抗結核菌之活性，因此進行成分分離，共得到41個化合物，包括四個butanolide類：kotolactone A (1)、kotolactone B (2)、isoobtusilactone A (3)、lincomolide B (4)；一個secobutanolide類：secokotomolide (5)；四個flavonoid類：apigenin (6)、kaempferol (7)、quercetin (8)、genkwanin (9)；三個flavan類：(+)-catechin (10)、(-)-catechin (11)、4’-hydroxy-5,7,3’-trimethoxyflavan-3-ol (12)；二個lignan類：(±)-syringaresinol (13)、(-)-sesamin (14)；八個benzenoid類：trans-ferulic acid (15)、trans-coumaric acid (16)、2,6-dimethoxy- 1,4-benzoquinone (17)、syringaldehyde (18)、vanillin (19)、4-hydroxybenzaldehyde (20)、protocatechuic acid (21)、benzoic acid (22)；六個steroid類：b-sitostenone (23)和stigmasta-4,22-dien-3-one (24) 的混合物、b-sitosterol (25) 和 stigmasterol (26)的混合物、b-sitosteryl-3-O-b-D-glucoside (27) 和stigmasteryl-3-O-b-D- glucoside (28)的混合物；一個triterpenoid 類：squalene (29)；一個 diterpenoid 類：trans-phytol (30)；二個 furan 類：2-acetyl-5- methylfuran (31)、2-acetyl-5-dodecylfuran (32)；九個 aliphatic compound 類：methyl palmitate (33) 和 methyl stearate (34)的混合物、palmitic acid (35)、margaric acid (36) 和 stearic acid (37) 的混合物、lauric acid (38)、docosanoic acid (39)、tetracosane (40)、kotodiol (41)。這些化合物均由光譜分析來決定其構造式。
其中，1、2、5及41為天然界首次分離到之新化合物，而32雖已被合成過，但為自天然界首次分離到之化合物。化合物3、25與26之混合物、33與34之混合物顯現有意義之抗結核菌活性。

關鍵字

蘭嶼肉桂 ； 樟科 ； 抗結核菌活性成分

並列摘要

Cinnamomum kotoense Kanehira & Sasaki (Lauraceae) is an evergreen small tree, endemic in Lanyu Island of Taiwan, and recently was cultivated for ornamental purpose in Taiwan Island. The chemical constituents and biological activities of this plant have never been studied. In a screening program of antitubercular activity on Formosan plants, C. kotoense was shown to be one of the active species. Investigation on the MeOH extract of the stem wood of this species has led to the isolation of 41 compounds, including four butanolides: kotolactone A (1), kotolactone B (2), isoobtusilactone A (3), lincomolide B (4); one secobutanolide: secokotomolide (5); four flavonoids: apigenin (6), kaempferol (7), quercetin (8), genkwanin (9); three flavans: (+)-catechin (10), (-)-catechin (11), 4’-hydroxy-5,7,3’- trimethoxyflavan -3-ol (12); two lignans: (±)-syringaresinol (13), (-)-sesamin (14); eight benzenoids: trans-ferulic acid (15), trans-coumaric acid (16), 2,6-dimethoxy-1,4-benzoquinone (17), syringaldehyde (18), vanillin (19), 4-hydroxybenzaldehyde (20), protocatechuic acid (21), benzoic acid (22)；six steroids：the mixture of sitostenone (23) and stigmasta-4,22-dien-3-one (24), the mixture of β-sitosterol (25) and stigmasterol (26), the mixture of β-sitosteryl-3-O-β-D-glucoside (27) and stigmasteryl-3-O-β-D- glucoside (28)；one triterpenoid：squalene (29)；one diterpenoid ：trans-phytol (30)；two furans ：2-acetyl-5-methylfuran (31), 2-acetyl-5-dodecylfuran (32)； nine aliphatic compounds：the mixture of methyl palmitate (33) and methyl stearate (34), the mixture of palmitic acid (35), margaric acid (36) and stearic acid (37), lauric acid (38), docosanoic acid (39), tetracosane (40), kotodiol (41). The structures of these compounds were determined by spectroscopic analysis.
Among these isolates, 1, 2, 5 and 41 were new compounds, and compound 32 was firstly isolated from plant origin, though it ever have been synthesized. Compound 3, the mixture of 25 and 26, and the mixture of 33 and 34 showed significant antitubercular activity in vitro.

並列關鍵字

Lauraceae ； Cinnamomum kotoense ； antitubercualr activity

參考文獻

參考文獻

1. 劉棠瑞，「植物分類學」，第肆卷，國立編譯館出版，1991，(a) p.379-380; (b) p.413。

2. 甘偉松，「藥用植物學」，國立中國醫藥研究所出版，1986， p.249-254。

3. Hsieh CF, Hung TC, Liao JC. Lauraceae in Flora of Taiwan, 2nd ed.; Editorial Committee of the Flora of Taiwan: Taipei, 1996, Vol. II, p. 443-444。

4. 廖日京，「台灣木本植物學名目錄」，台灣大學森林系出版，1993，p.49。