pinoresinol β-D-glucopyranoside | 185210-52-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: pinoresinol β-D-glucopyranoside
• 英文别名: pinoresinol-4'-O-β-D-monoglucoside；Simplokosin；(-)-pinoresinol O-beta-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[4-[3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 185210-52-0
• 化学式: C₂₆H₃₂O₁₁
• 分子量: 520.533
• InChiKey: QLJNETOQFQXTLI-JBDZBTHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 以42.5 mg的产率得到pinoresinol β-D-glucopyranoside
  参考文献：
  名称：

  Non-host disease resistance response in pea (Pisum sativum) pods: Biochemical function of DRR206 and phytoalexin pathway localization

  摘要：

  Continually exposed to potential pathogens, vascular plants have evolved intricate defense mechanisms to recognize encroaching threats and defend themselves. They do so by inducing a set of defense responses that can help defeat and/or limit effects of invading pathogens, of which the non-host disease resistance response is the most common. In this regard, pea (Pisum sativum) pod tissue, when exposed to Fusarium solani f. sp. phaseoli spores, undergoes an inducible transcriptional activation of pathogenesis-related genes, and also produces (+)-pisatin, its major phytoalexin. One of the inducible pathogenesis-related genes is Disease Resistance Response-206 (DRR206), whose role in vivo was unknown. DRR206 is, however, related to the dirigent protein (DP) family. In this study, its biochemical function was investigated in planta, with the metabolite associated with its gene induction being pinoresinol monoglucoside. Interestingly, both pinoresinol monoglucoside and (+)-pisatin were co-localized in pea pod endocarp epidermal cells, as demonstrated using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry imaging. In addition, endocarp epidermal cells are also the site for both chalcone synthase and DRR206 gene expression. Taken together, these data indicate that both (+)-pisatin and pinoresinol monoglucoside function in the overall phytoalexin responses. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.10.013