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

다국어 초록 (Multilingual Abstract)

<P>Five new constituents, 5,4′-dihydroxy-7,3′-dimethoxyflavone-4′-<I>O</I>-β-<SMALL>d</SMALL>-xylopyranosyl-(2a→1b)-2a-<I>O</I>-β-<SMALL>d</SMALL>-xylopyranosyl-(2b→1c)-2b-<I>O</I>-β-<SMALL>d</SMALL>-xylopyranosyl-2c-octadecanoate (<B>1</B>), 5,4′-dihydroxy-7,3′-dimethoxyflavone-4′-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2a→1b)-2a-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2b→1c)-2b-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2c→1d)-2c-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-2d-octadecanoate (<B>2</B>), kaempferol-3-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2a→1b)-2a-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2b→1c)-2b-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2c→1d)-2c-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-2d-hexadecanoate (<B>3</B>), methyl salicylate-2-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2a→1b)-2a-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2b→1c)-2b-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2c→1d)-2c-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2d→1e)-2d-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2e→1f)-2e-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2f→1g)-2f-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-(2g→1h)-2g-<I>O</I>-α-<SMALL>d</SMALL>-xylopyranosyl-2h-geranilan-8′,10′-dioic acid-1′-oate (<B>4</B>), and oleioyl-β-<SMALL>d</SMALL>-arabinoside (<B>5</B>), 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 (<B>1</B>–<B>5</B>) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound <B>5</B> had the highest growth inhibition (92.6 ± 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound <B>5</B> has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.</P><P><B>Graphic Abstract</B>
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