3-methyl-1-buten-3-yl-6-o--xylopyranosyl--D-gluco- pyranoside from Paederia scanders

3-methyl-1-buten-3-yl-6-o--xylopyranosyl--D-glucopyranoside has been isolated from the methanolic extract of the roots of Vietnamese Paederia scanders. Its structure was elucidated by the combination of 2D NMR, IR and high resolution FAB-MS spectroscopy and chemical reaction, such as acetylation.
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3-methyl-1-buten-3-yl-6-o--xylopyranosyl--D-gluco- pyranoside from Paederia scandersJournal of Chemistry, Vol. 44 (1), P. 88 - 90, 2006 3-methyl-1-buten-3-yl-6-o- -xylopyranosyl- -D-gluco- pyranoside from Paederia scanders Received 26 August 2004 Dang Ngoc Quang1, Nguyen Xuan Dung2 1 Faculty of Chemistry, Hanoi University of Education 2 Faculty of Chemistry, College of natural Science, VNU Summary 3-methyl-1-buten-3-yl-6-o- -xylopyranosyl- -D-glucopyranoside has been isolated from the methanolic extract of the roots of Vietnamese Paederia scanders. Its structure was elucidated by the combination of 2D NMR, IR and high resolution FAB-MS spectroscopy and chemical reaction, such as acetylation. I - Introduction NMR spectra were recorded on Varian Unity 600 (600 MHz), using either CDCl3 or Paederia scanders (Lour.) Merril belonging CD3OD as solvent. Mass spectra including high-to Rubiaceae widely grows in East Asia, such as resolution and high-resolution FAB massVietnam, China, Japan, and Philippines [1]. The spectra were recorded on a JEOL JmS AX-500aerial parts of this plant are utilized for diuretic, spectrometer. IR spectra were measured onemetic, rheumatic arthritis and curing bacillary JASCO FT/IR-5300 spectrophotometer. Thedysentery, while the young leaves are eaten as specific optical rotations were measure on avegetable [2, 3]. Previously, several glucosides, JASCO DIP-1000 polarimeter with CHCl3 assuch as paederoside, paederosidic acid, solvent. HPLC was performed on Shimadzuasperuloside, and scandoside, et al. have been liquid chromatography LC-10 AS with RID-6Aisolated from the leaves and sterm of P and SPD-10A detectors using a Waters 5C 18-scandens [4, 5]. Later, some of which performed AR-II column. TLC was performed on silica gelthe inhibitory effect on Epstein-Barr virus plates (Kiesegel 60 F254, Merck) and reversedactivation [3]. In the course of our inverstigation phase C18 silica gel plates (Merck).of the biologically active compounds from 2. MaterialsVietnamese medicinal plants, we reported theisolation and structural elucidation of three Fresh roots of Paederia scandens (Lour.)sulfur-containing bis-iridoid glucosides and two Merril were collected in Hanoi, Vietnam in Julyiridoid glucosides from the roots of Vietnamese 2000 and then identified by Dr. Tran Ngoc NinhP. scandens [6]. In continuation, a new (Institute for Ecology and Natural Resources,glycoside is reported in this paper. Hanoi Vietnam). The vourcher specimen (VN 02001) has been deposited in Faculty of II - Experimental Pharmaceutical Sciences, Tokushima Burin University Japan.1. General 3. Extraction and isolation88 The roots of P. scandens (3.2 kg) were dried Positive FAB-MS: 403 [M+Na]+. HR-FABMS:at room temperature and powdered, the extracted m/z 403.1562 (C16H28O10Na, requires m/zwith MeOH using Soxhlet apparatus. The MeOH 403.1580). IR (KBr): 3390, 2979, 2927, 1645,extract was concentrated to give a residua (118.6 1417, 1366, 1264, 1087, 928 cm-1. 1H and 13C-g), which was partitioned between butanol and NMR (CD3OD) (table 1).water. The butanol layer was concentrated to Acetylation of 1: Compound 1 (14.5 mg) wasgive (57.2 g) a stick residue. The butanolic acetylated with Ac2O in pyridine. Work up asextract (19.79 g) was chromatographed on silica usual gave compound 2 (12.9 mg). [ ]20D - 33.5ogel column, using CHCl3-MeOH-H2O (65 15 : (c 1.13, CHCl3). Positive FAB-MS: 65510, lower phase) as eluent resulted in the [M+Na]+. HR-FABMS: m/z 655.2234isolation of 6 fractions. Fraction 6 (683 mg) was (C28H40O16Na, requires m/z 655.2214). IRpurified repeatedly by reversed phase preparative (KBr): 2926, 2853, 1752, 1714, 1640, 1433,HPLC, H2O-MeOH (1.5 : 1) as solvent system to 1369, 1221, 1039, 910 cm-1. 1H and 13C NMRgive 1 (22.2 mg). [ ]D20 - 47.6o (c 0.84, CHCl3). (CDCl3) (table 1). Table 1: 1H and 13C NMR spectral data for 1 (CD3OD) and 2 (CDCl3) Compound 1 Compound 2 Position 1 13 1 13 H C H C 5.12 (dd, 1.4, 11.0) 5.18 (dd, 0.8, 11.0) 1 114.5 114.9 5.22 (dd, 1.4, 17.9 5.19 (dd, 0.8, 17.6) 2 6.02 (dd, 11.0, 17.9) 145.2 5.81 (dd, 11.0, 17.6) 142.7 3 79.2 78.5 4 1.38 s 26.6 1.33 s 26.0 5 1.33 s 27.9 1.27 s 27.3 1’ 4.32 (d, 8.0) 99.6 ...