New Chemical Constituents from Oryza sativa Straw and Their Algicidal Activities against Blue-Green Algae

作者:Ahmad Ateeque; Kim Seung Hyun; Ali Mohd; Park Inmyoung; Kim Jin Seog; Kim Eun Hye; Lim Ju Jin; Kim Seul Ki; Chung Ill Min*
来源:Journal of Agricultural and Food Chemistry, 2013, 61(34): 8039-8048.
DOI:10.1021/jf402145u

摘要

Five new constituents, 5,4%26apos;-dihydroxy-7,3%26apos;-dimethoxyflavone-4%26apos;-O-beta-D-xylopyranosyl-(2a -%26gt; 1b)-2a-O-beta-D-xylopyranosyl-(2b -%26gt; 1c)-2b-O-beta-D-xylopyranosyl-2c-octadecanoate (1), 5,4%26apos;-dihydroxy-7,3%26apos;-dimethoxyflavone-4%26apos;-O-alpha-D-xylopyranosyl(2a -%26gt; 1b)-2a- O-alpha-u-xyl opyran osyl- (2b -%26gt; 1c)-2b-O-alpha-D-xylopyranosyl-(2c -%26gt; 1c)-2c- O-alpha-D-xylopyranosy1-2d-octadecanoate (2), kaempferol-3-O-alpha-D-xylopyranosyl- (2a -%26gt; 1b)-2a-O-alpha-D-xylopyranosyl-(2b -%26gt; 1c)-2b-O-alpha-D-xylopyranosyl-(2c -%26gt; 1d)-2c-O-alpha-D-xylopyranosy1-2d-hexadecanoate (3), methyl salicylate-2-O-alpha-u-xylopyranosyl-(2a -%26gt; 1b)-2a-O-alpha-D-xylopyranosyl-(2b -%26gt; 1c)-2b-O-alpha-D-xylopyranosyl-(2c -%26gt; 1d) -2c-O-alpha-D-xylopyranosyl-(2d -%26gt; 1e)-2c-O-alpha-D-xylopyranosyl-(2e -%26gt; 1b)-2a-O-alpha-a-D-xylopyranosyl- (2f -%26gt; 1g) 1g)-2f-O-alpha-D-xylopyranosyl-(2g -%26gt; 1h)-2g-O-alpha-D-xylopyranosyl-2h-geranilan-8%26apos;,10%26apos;-dioic acid-1%26apos;-oate (4), and oleioyl-beta-D-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound S had the highest growth inhibition (92.6 +/- 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.

  • 出版日期2013-8-28