methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate | 1450589-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate
• 英文别名: 2-[2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-2-[(2R,3R,4S,5R)-4,5-dihydroxy-2-(2-methoxycarbonylphenoxy)oxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-2-oxoethyl]-6-methylheptanedioic acid
• CAS: 1450589-83-9
• 化学式: C₅₈H₈₆O₄₀
• 分子量: 1423.3
• InChiKey: UARLREKLODYDOD-AZJOSDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  98
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  599
• 氢给体数：
  18
• 氢受体数：
  40

反应信息

• 作为反应物：
  描述：

  methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 水杨酸甲酯
  参考文献：
  名称：

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

  摘要：

  Five new constituents, 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-beta-D-xylopyranosyl-(2a -> 1b)-2a-O-beta-D-xylopyranosyl-(2b -> 1c)-2b-O-beta-D-xylopyranosyl-2c-octadecanoate (1), 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-alpha-D-xylopyranosyl(2a -> 1b)-2a- O-alpha-u-xyl opyran osyl- (2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1c)-2c- O-alpha-D-xylopyranosy1-2d-octadecanoate (2), kaempferol-3-O-alpha-D-xylopyranosyl- (2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d)-2c-O-alpha-D-xylopyranosy1-2d-hexadecanoate (3), methyl salicylate-2-O-alpha-u-xylopyranosyl-(2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d) -2c-O-alpha-D-xylopyranosyl-(2d -> 1e)-2c-O-alpha-D-xylopyranosyl-(2e -> 1b)-2a-O-alpha-a-D-xylopyranosyl- (2f -> 1g) 1g)-2f-O-alpha-D-xylopyranosyl-(2g -> 1h)-2g-O-alpha-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-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.

  DOI：

  10.1021/jf402145u

文献信息

• New Chemical Constituents from Oryza sativa Straw and Their Algicidal Activities against Blue-Green Algae
  作者：Ateeque Ahmad、Seung-Hyun Kim、Mohd Ali、Inmyoung Park、Jin-Seog Kim、Eun-Hye Kim、Ju-Jin Lim、Seul-Ki Kim、Ill-Min Chung

  DOI：10.1021/jf402145u

  日期：2013.8.28

  Five new constituents, 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-beta-D-xylopyranosyl-(2a -> 1b)-2a-O-beta-D-xylopyranosyl-(2b -> 1c)-2b-O-beta-D-xylopyranosyl-2c-octadecanoate (1), 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-alpha-D-xylopyranosyl(2a -> 1b)-2a- O-alpha-u-xyl opyran osyl- (2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1c)-2c- O-alpha-D-xylopyranosy1-2d-octadecanoate (2), kaempferol-3-O-alpha-D-xylopyranosyl- (2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d)-2c-O-alpha-D-xylopyranosy1-2d-hexadecanoate (3), methyl salicylate-2-O-alpha-u-xylopyranosyl-(2a -> 1b)-2a-O-alpha-D-xylopyranosyl-(2b -> 1c)-2b-O-alpha-D-xylopyranosyl-(2c -> 1d) -2c-O-alpha-D-xylopyranosyl-(2d -> 1e)-2c-O-alpha-D-xylopyranosyl-(2e -> 1b)-2a-O-alpha-a-D-xylopyranosyl- (2f -> 1g) 1g)-2f-O-alpha-D-xylopyranosyl-(2g -> 1h)-2g-O-alpha-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-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.