紅番石榴及綠珊瑚極性成份之研究

Studies on the Polar Constituents from Psidium guajava L. and Euphorbia tirucalli L.

葉昌河(Yeh, Chang Ho)

指導教授 ： 徐鳳麟 博士

臺北醫學大學/藥學院/藥學研究所/碩士(1997年)

摘要

鞣質為廣布於植物界之一群多酚性化合物，其化學性質至最近幾年， 由於分離技術及 光譜儀器之進步，陸續始被了解。藉由新 的鞣質及其相關化合物之探索，多酚性化合物之 生物活性也 陸續被學者所發現，因而鞣質化學為天然藥物研究之一新的領域。因此， 本論 文以紅肉番石榴果實及綠珊瑚進行研究為目的，探討其所含 之極性化合物。 紅肉番石榴為桃金孃科植物，原產於熱帶美洲 ，現臺灣已有引進栽培，民間取其葉或未成熟果實來治療糖尿病及腹瀉。 將新鮮未成熟果實以70 %丙酮進行萃取，經各種管柱層析，共得十二個化 合物，經光譜分析確認其結構分別為gallic acid (1)、castalagin (2)、vescalagin (3)、pedunculagin (4)、casuarinin (5)、(+)- catechin (6)、(+)-gall-ocatechin (7)、procyanidin B-1 (8)、 quercetin (9)、quercetin-3-O-galactoside (10)、D-threo-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (11)、D-erythro-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (12). 。其中以 castalagin及catechin為主成分。Compound 11及12為首次自植物分離純 化並確定其化學結構及光譜特徵。 綠珊瑚為大戟科植物，廣泛分佈於 熱帶地區，臺灣及澎湖等地亦有栽培。民間用於止痛，手足麻痺及皮膚病 之治療。將其新鮮之植物地上部以60% 丙酮進行萃取，經各種管柱層析， 共得十三個化合物，經確認其結構分別為gallic acid (1)、1-O- galloyl-?-D-glucose (13)、1,2,3-tri-O-galloyl-?-D-glucose (14)、pedunculagin (4)、corilagin (15)、casuariin (16)、5- desgalloylstachyurin (17)、2,3-(S)-HHDP-D-glucose (18)、 putranjivain A (19)、putranjivain B (20)、quercitrin (21)、rutin (22)、3,3'-di- O-methyl ellagic acid (23)、3,3',4-tri-O- methyl-4'-O-rutinosyl ellagic acid (24)。其中以corilagin 及 putranjivain B (1C4 type ellagitannins)為主要成分。 Compound 11及12為首次自植物分離純化並確定其化學結構及光譜特徵，同時 compound 24之NMR光譜特徵，亦於本次探討中首次藉由2D-NMR技術加以確 立。

關鍵字

紅番石榴 ； 綠珊瑚 ； 單寧 ； 多酚性化合物 ； 二維核磁共振光譜

並列摘要

Tannins are polyphenolic compounds which widely exist in plant kingdom. Recently, their characteristics have been realized together with developmentof chromatography techniques and spectrascopic analysis. The bioactivitiesof polyphenolic compounds also have been reported successively. Thus, tanninchemistry is a new research field of natural products. Red guava, a variant of Psidium guajava L. (Myrtaceae), was originated fromtropic America and have been naturalized in Taiwan for a long time. The immat-ure fruit of red guava have been used as a folk medicine for treatment of hyp-perglycemia and diarrhea. However, the active chemical constituents and relatedpharmacological activities are still remained to be explored. The immature fruitwere extracted with 70 % aqueous acetone. By means of various column chromatog-raphies, 12 compounds were isolated and purified. The chemical structures of these compounds were elucidated as gallic acid (1), castalagin (2), vescalagin (3), pedunculagin (4), casuarinin (5), (+)-catechin (6), (+)-gallocatechin (7),procyanidin B-1 (8), quercetin (9), quercetin-3-O-galactoside (10), D-threo-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (11), D-erythro-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (12). Among them, castalagin and (+)-catechin are majorcomponents. D-threo-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (11) andD-erythro-1-C- guaiacylglycerol 3-O-?-D-glucopyranoside (12) were characterizedfor thr first time from plant source. Euphorbia tirucalli L., an Euphorbiaceous plant, widely distribute in tropics. There are cultivated plants in Taiwan and Pen-huo islands. It has been used asa folk medicine in treatment of dermatosis, paralysis, and pain of human body.However, the active chemical constituents and related pharmacological activitiesare still remained to be explored. Euphorbia tirucalli were extracted with 60%aqueous acetone. By means of various column chromatographies, 14 compounds wereisolated and characterized. The chemical structures of these compounds wereelucidated as gallic acid (1), 1-O-galloyl-?-D-glucose (13), 1,2,3-tri-O- galloyl-?-D-glucose (14), pedunculagin (4), corilagin (15), casuariin (16), 5-desgalloylstachyurin (17), 2,3-(S)- HHDP-D-glucose (18), putranjivain A (19), putranjivain B (20), quercitrin (21), rutin (22) , 3,3'-di-O-methyl-ellagic acid(23) , 3,3',4-tri-O-methyl-4'-O-rutinosyl-ellagic acid (24) . Among them, cori-lagin and putranjivain B (1C4 type ellagitannins) are major components. Compound 11 and compound 12 are isolated from plant source and elucidated their chemical structures for the first time and the NMR characteristics of compound 24 are characterized by 2D-NMR technologies in this investigation.

並列關鍵字

Psidium guajava L. ； Euphorbia tirucalli L. ； Tannin ； Polyphenolic compound ； 2D-NMR spectra