佩羅特木莖部化學成分之研究

Chemical Constituents of the Stems of Perrottetia arisanensis

杜英齊(Ying-Chi Du)

指導教授 ： 吳永昌

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2006年)

摘要

佩羅特木，為衛矛科(Celastraceae)核子木屬(Perrottetia)植物。是台灣此屬植物中僅有的一種，主要生長於台灣的中海拔地區。本研究將該植物的莖部(1.58 Kg) 經甲醇冷浸連續抽取，所得之抽取液經減壓濃縮後，進行分配萃取，得到n-Hexane、5% aqueous MeOH、n-BuOH、H2O四層。利用管柱層析法，以矽膠(Silica gel)、分子篩(Sephadex LH-20)等材質為固定相，配合有機溶媒沖提及高效能液相層析分析儀(HPLC)等儀器，進行成分分離與純化。
至目前共分離得到三十一個化合物，分別為十四個triterpenes：betulinic acid (1)、3??-methoxybetulinic acid (2)、lupeol (3)、3-epi-
betulinic acid (4)、3-epi-betulinaldehyde (5)、3-epi-thurberogenin (6)、3-epi-thurberogenin-22??-dodecanoate (7)*、3-epi- thurberogenin-22??-tetradecanoate (8)*、3-epi-thurberogenin-22??- hexadecanoate (9)*、thurberogenin (10)、thurberogenone (11)、7??-cis-coumaroylbetulinic acid (12)*、7??-trans-coumaroylbetulinic acid (13)*、7??-hydroxybetulinaldehyde (14)*;八個flavonoids：(2S)-naringenin (15)、dihydrokaempferol (16)、quercetin (17)、eriodictyol (18)、luteolin (19)、kaempferol (20)、chrysoeriol (21)與diosmetin(22)混合物;四個steroids：β-stigmasterol (23)與β-sitosterol (24)混合物、stigmasteryl-3-O-β-D-glucoside (25)與β-sitostery-3-O-β-D-glucoside (26)混合物;一個chromone：5,7-dihydroxychromone (27);一個chlorophyll：phaeophorbide a methyl ester (28);一個diterpene：phytol (29);二個benzenoids：4-dihydroxybenzoic acid (30)、trans-coumaric acid (31)。
其中化合物7、8、9、12、13及14為新化合物，以上化合物之結構式皆以質譜及光譜分析方法確認。
本實驗所得化合物皆為首次從此植物中分離得到，其生物活性正在進行中。

關鍵字

佩羅特木 ； 核子木屬 ； 衛矛科

並列摘要

Perrottetia arisanensis (Celastraceae), distributed in the middle elevation in Taiwan, is the only species of this genus in Formosa. In the current study, the stems (1.58 kg) of this plant were collected and extracted by MeOH. The extract was then partitioned to yield four layers (n-Hexane, 5% aqueous MeOH, n-BuOH and H2O).
Chromatographic separation of the 5% aqueous MeOH and n-BuOH fractions yielded thirty-one compounds, including fourteen triterpenes: betulinic acid (1), 3??-methoxybetulinic acid (2), lupeol (3), 3-epi-betulinic acid (4), 3-epi-betulinaldehyde (5), 3-epi- thurberogenin (6), 3-epi-thurberogenin-22??-dodecanoate (7)*, 3-epi-thurberogenin-22??-tetradecanoate (8)*, 3-epi-thurberogenin- 22??-hexadecanoate (9)*, thurberogenin (10), thurberogenone (11), 7??-cis-coumaroylbetulinic acid (12)*, 7??-trans-coumaroylbetulinic acid (13)*, 7??-hydroxybetulinaldehyde (14)*, eight flavonoids: (2S)-naringenin (15), dihydrokaempferol (16), quercetin (17), eriodictyol (18), luteolin (19), kaempferol (20), chrysoeriol (21) and diosmetin (22) mixtures, four steroids: β-stigmasterol (23) and β-sitosterol (24) mixtures, stigmasteryl-3-O-β-D- glucoside (25) and β-sitostery-3-O-β-D-glucoside mixtures (26), one chromone: 5,7-dihydroxychromone (27), one chlorophyll: phaeophorbide a methyl ester (28), one diterpene: phytol (29), two benzenoids: 4-dihydroxybenzoic acid (30), trans-coumaric acid (31). The structures of the isolates were identified by mass and NMR spectral analysis.
These compounds were isolated for the first time from P. arisanensis. Among them, 7, 8, 9, 12, 13, and 14 are new compounds. The biologic activities are currently under investigation.

並列關鍵字

Perrottetia arisanensis ； Celastraceae

參考文獻

1. Flora of Taiwan 1993, 3, 640-660.

2. Gonzalez, A. G.; Bazzocchi, I. L.; Jiménez, I. A.; Moujir, L. In Studies in Natural Products Chemistry 2000, 23, 649-738.

3. Iménez, I. A.; Bazzocchi, I. L.; Núũez, J.; Mukainaka, T.; Tokuda, H.; Nishino, H.; Konoshima, T.; Ravelo, A. G. J. Nat. Prod. 2003, 66, 1047-1050.

4. Spivey, A. C.; Weston, M.; Woodhead, S. Chem. Soc. Rev. 2002, 31, 43-59.

5. Shishido, K.; Nakano, K.; Wariishi, N.; Tateishi, H.; Omodani, T.; Shibuya, M.; Goto, K.; Ono, Y.; Takaishi, Y. Phytochemistry 1994, 35, 731-737.