Desmos cochinchinensis var. fulvescens Ban 葉部化學成分之研究

Chemical Constituents of the Leaves of Desmos cochinchinensis var. fulvescens Ban

鄭富庭(Fu-Ting Cheng)

指導教授 ： 張芳榮

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2011年)

摘要

黃毛假鷹爪(暫譯)，為番荔枝科(Annonaceae)假鷹爪屬(Desmos)植物Desmos cochinchinensis之變種，係越南特有之番荔枝科植物，主要生長於越南的海岸線森林區。本研究收集該植物的葉部(10.0公斤)利用甲醇抽提，再進行分配萃取，得到n-Hexane、20% aqueous MeOH、n-BuOH、H2O四層。利用管柱層析法，以矽膠(Silica gel)、分子篩(SephadexR 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。
此研究結果從黃毛假鷹爪葉部分離純化得到32個純化合物，分別為1個grandiuvarin衍生物：grandauvarin D (1)；10個sesquiterpenes：desmoscochinone (2)、selin-4(15)-en-1,11-diol (3)、4-epi-cryptomeridiol (4)、cryptomeridiol (5)、11α-hydroxyl-4β- methoxyselinane (6)、4α,10β-dihydroxyaromadendrane (7)、4α,10α- dihydroxyaromadendrane (8)、pipelol A (9)、10??-hydroxyisodauc- 6-en-14-al (10)、alismoxide (11)；5個flavonoids：6-(2’-hydroxybenzyl)-7-
methoxyflavonone (12)、matteuorien (13)、kaempferol (14) kaempferol-3- O-??-glucopyranoside (15)、kaempferol-3-O-??-rhamnopyranoside (16)；1個megastigmene：3??,4??,6??,9-tetrahydroxy-5?圁,7-megastigmene (17)；1個neolignan：guajacylglycerin-β-O-4’-dihydroconiferylether (18)；1個organic acid：3,4,5-trihydroxypentanoic acid (19)；1個benzenoid：benzoic acid (20)以及2個steroids組合物：stigmasteryl-3-O-??-D-glucoside (21)、??-sitosteryl-3-O-??-D-glucoside (22)；其餘11個化合物尚待解析。在這些化合物中1、2、12及17為新化合物，9為首次由天然物中分離之化合物；此外，1-20均為首次由假鷹爪屬分離而得之化合物。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屬植物中分離得到，此材料亦為全球首度被研究之假鷹爪屬變種植物。其萃取物具有顯著抗發炎生物活性，純化合物之生物活性試驗正在進行中。

關鍵字

番荔枝科 ； 假鷹爪屬 ； 黃毛假鷹爪 ； 細胞毒殺 ； 抗發炎

並列摘要

Desmos cochinchinensis var. fulvescens (Annonaceae), a variety of D. cochinchinensis, is an endemic species scattered in light coast forests of Vietnam. In the current study, the leaves (10.0 kg) of this plant were collected and extracted by MeOH. The extract was then partitioned to yield four layers (n-Hexane, 20% aqueous MeOH, n-BuOH and H2O layer). In these four layers, 20% aqueous MeOH layer showed significant anti-inflammatory activity. Chromatographic separation of the 20% aqueous MeOH fractions yielded thirty-two compounds. Among them, twenty-two compounds were identified, including one grandiuvarin derivate: grandiuvarin D (1), ten sesquiterpenes: desmoscochinone (2), selin-4(15)-en-1,11-diol (3), 4-epi-cryptomeridiol (4), cryptomeridiol (5), 11α-hydroxyl-4β-methoxyselinane (6), 4α,10β-dihydroxyaromadendrane (7), 4α,10α-dihydroxyaromadendrane (8), pipelol A (9), 10??- hydroxyisodauc-6-en-14-al (10), alismoxide (11), five flavonoids: 6-(2’-hydroxybenzyl)-7-methoxyflavanone (12), matteuorien (13), kaempferol (14), kaempferol-3-O-??-glucopyranoside (15), kaempferol-3-O-??-rhamnopyranoside (16), one megastigmane: 3??,4??,6??,9-tetrahydroxy-5?圁,7-megastigmene (17), one neo-lignan: guajacylglycerin-β-O-4’-dihydroconiferylether (18), one organic acid: 3,4,5-trihydroxypentanoic acid (19), one benzenoid: benzoic acid (20), and two steroid: a mixture of stigmasteryl-3-O-??-D-glucoside (21) and ??-sitosteryl-3-O-??-D-glucoside (22). The structures of the isolates were identified by spectral analysis. In addition, eleven compounds are still under elucidating.
These compounds were isolated for the first time from Desmos genus. Among these ingredients, 1, 2, 12, and 17 are new compounds, and 9 is firstly isolated from nature. The biological activities of isolates are currently under investigation.

並列關鍵字

Annonaceae ； Desmos ； Desmos cochinchinensis var. fulvescens Ban ； cytotoxicity ； anti-inflammatory

參考文獻

1. 廖日京，”台灣木本植物學名目錄”，台灣大學森林學系，1993, p.49.

2. 蔣英, 李秉滔, 李延輝，”中國植物志”，北京科學出版社，1979, 30,

(2), 10.

3. Liao, S. X.; han, G. Y.; R., Z. Y.; T., Z. Q.; H., H. C., Studies on the chemical constituents of the root of Desmos cochinchinensis Lour. Yao Xue Xue Bao 1989, 24, (2), 110-113.

4. Nguyen, N. T.; Pham, V. C.; Litaudon, M.; Gueritte, F.; Bodo, B.; Nguyen, V. T.; Nguyen, V. H., Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone. Tetrahedron 2009, 65, 7171-7176.