莪朮地上部成分之研究

Abstract

根據本研究室過去的研究，薑科植物薑黃地上部富含黃酮醇類成分，同屬植物莪朮地上部揮發油成分已有報導，但較高極性成分仍無報導，因此本研究擬探討莪朮地上部之成分。 將莪朮地上部之乙醇萃取物經極性分割後劃分為乙腈、乙酸乙酯、正丁醇和水可溶部分，並進一步對乙腈、乙酸乙酯和正丁醇可溶部分進行成分分離。過程中使用Sephadex LH-20、silica gel和逆相層析管柱、離心式分配層析，以及半製備HPLC等分離技術，共計得到23個化合物，經由核磁共振譜及質譜技術分析確認其結構，包括14個黃酮醇類：quercetin (3)、quercetin 3-O– β-D-glucuronide (1)、α-L-rhamnosyl-(1→2)-β-D-glucuronide (4)、α-L-rhamnosyl-(1→2)-β-D-galactoside (8)、β-D-glucoside (12)、α-L-arabinopyranoside (14)、α-L-rhamnoside (15)、β-D-glucuronide methyl ester (16)及α-L-rhamnosyl-(1→2)-α-L-arabinopyranoside (17)，kaempferol 3-O– β-D-glucuronide (2)、α-L-rhamnosyl-(1→2)-β-D-glucuronide (7)、α-L-rhamnosyl-(1→2)-β-D-galactoside (9)、β-D-glucoside (11)及β-D-galactoside (13); 2個核苷類：adenosine (5)與uridine (6); 3個苯丙烷類：5-O-caffeoylshikimic acid (10)、methyl feruloyl malate (19)及p-coumaric acid (20);3個倍半萜類：epi-oxycurcumenol (21)、(1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone (22)及zedoarondiol (23)和1個苯甲酸衍生物：4-hydroxybenzoic acid (18)。其中化合物21為首次分離出之天然物，雖然已由合成製備。

Our recent studies on the aerial part of Curcuma longa (Zingiberaceae) indicated it to be rich in flavonols. The essential oils from the aerial part of the related species, Curcuma aeruginosa Roxb., have been reported but other constituents remain disclosed. Thus this thesis was aimed to investigate the chemical constituents from the aerial part. The ethanol extract of the aerial part of C. aeruginosa was divided into fractions soluble in MeCN, EtOAc, n-BuOH, and water via liquid-liquid partitioning. The MeCN, EtOAc, and n-BuOH -soluble fractions were chromatographed over Sephadex LH-20, silica gel, and reversed-phase columns, centrifugal partition chromatography, and semi-preparative RP-HPLC, monitored by ESI-MS and TLC. This effort led to the isolation of 23 compounds, whose structures were determined based on 1H and 13C NMR spectroscopic analyses and MS data. They are 14 flavonols: quercetin (3), quercetin 3-O– β-D-glucuronide (1), α-L-rhamnosyl-(1→2)-β-D-glucuronide (4), α-L-rhamnosyl-(1→2)-β-D-galactoside (8), β-D-glucoside (12), α-L-arabinopyranoside (14), α-L-rhamnoside (15), β-D-glucuronide methyl ester (16), and α-L-rhamnosyl-(1→2)-α-L-arabinopyranoside (17); kaempferol 3-O– β-D-glucuronide (2), α-L-rhamnosyl-(1→2)-β-D-glucuronide (7), α-L-rhamnosyl-(1→2)-β-D-galactoide (9), β-D-glucoside (11), and β-D-galactoide (13); two nucleosides: adenosine (5) and uridine (6); three phenylpropanoids: 5-O-caffeoylshikimic acid (10), methyl feruloyl malate (19), and p-coumaric acid (20); three sesquiterpenoids: epi-oxycurcumenol (21), (1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone (22), and zedoarondiol (23); one phenolics: 4-hydroxybezoic acid (18). Among these, compound 21 is a new natural product although it has been prepared synthetically.