M. Parveen et al. / Chinese Chemical Letters 21 (2010) 593–595
595
ꢁ
+
+
The mass spectrum (Fig. 1) of 1 fully supported the assigned structure of the glycoside as it exhibited 330 [M-gly]
as the base peak. This was further supported by the RDA fragmentation [24] respectively. Ring A (m/z 153 [A + H] ,
1
ꢁ
52 [A ] ) and B (m/z 181 [B ] , 178 [B ] ) which are indicative of the presence of two hydroxyl groups in ring A
1 1
+
+
ꢁ+
1
1
and two methoxyl and one hydroxyl group in ring B of the aglycone. The presence of peaks at m/z 259, 199, 169, 157
and 130 in the mass spectrum of acetate, finally established the sugar moiety as pentopyranoside [25].
The position of sugar residue in 1 was confirmed by hydrolysis of methylated glycoside. The methylated aglycone
corresponded the molecular formula C H O , showed bathochromic shift of 10 nm in band II with NaOAc,
1
9 18 7
confirming that C-7 hydroxyl which was glycosylated in C-7 had become free. The formation of this partial methyl
ether thus proved that the sugar arabinose was linked to C-7 hydroxyl of the aglycone. The methylated sugar was
identified as 2,3,4-tri-O-methyl-L-arabinose as a colourless liquid [a] -122 (in water). The quantitative estimation of
D
sugar by Somogyi’s copper micro method [26] showed the presence of one mole of arabinose per mole of aglycone.
0
Compound 1 was therefore characterized as tricin-4 -O-b-L-arabinoside. It was interesting to note the configuration of
arabinose is b which is of rare occurrence.
The compound 1 showed significant antimicrobial activity using agar well diffusion method [27]. The in vitro
antibacterial activity against Staphylococcus aureus (IAO-SA-22), Escherichia coli (K-12) and in vitro antifungal
activity against Salmonella typhimurium (MTCC-98), Candida albicans (IAO-109) was carried out, with
chloramphenicol and nystatin respectively, as positive control. With a concentration of 1 mg/mL, the novel
flavonoidic glycoside 1 showed inhibitory activities against growth of S. aureus, E. coli, S. typhimurium and C.
albicans. The most promising result was observed against S. typhimurium with zone of inhibition 20 mm, while E. coli
ranked next (16 mm) followed by S. aureus and C. albicans whose zone of inhibition were 13 and 12 mm respectively.
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