graveobioside A | 506410-53-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: graveobioside A
• 英文别名: Graveobioside A；7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
• CAS: 506410-53-3
• 化学式: C₂₆H₂₈O₁₅
• 分子量: 580.499
• InChiKey: YSXNEFJASLJGTK-YRCFQSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  graveobioside A 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以45.6 mg的产率得到木犀草素
  参考文献：
  名称：

  Ovipositional Deterrent in the Sweet Pepper,Capsicum annuum, at the Mature Stage againstLiriomyza trifolii(Burgess)

  摘要：

  Liriomyza trifolii (Burgess) 是一种美国蛇纹石潜叶蝇，是全世界众所周知的严重害虫。这种昆虫会侵害 21 个不同的植物科，包括茄科植物。不过，成熟的甜椒辣椒（茄科）对这种潜叶蝇具有抗性。这种抗性是基于甜椒叶片中的卵巢对这种蝇类的威慑力。根据生物测定指导下的分馏，分离并鉴定出木犀草素 7-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside，作为对这种昆虫的产卵阻遏剂。这种化合物能完全阻止 L. trifolii 雌虫在以 4.90 μg/cm2 浓度处理的寄主植物叶片上产卵。

  DOI：

  10.1271/bbb.69.1831
• 作为产物：
  描述：

  luteolin 7-O-(2-apiosyl-6-malonyl)glucoside 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.17h， 以0.3 g的产率得到graveobioside A
  参考文献：
  名称：

  Absorption and Metabolism of Luteolin in Rats and Humans in Relation to in Vitro Anti-inflammatory Effects

  摘要：

  Luteolin is a flavonoid present in plants in the form of aglycone or glucosides. In this study, luteolin glucosides (i.e., luteolin-7-O-beta-D-glucoside, luteolin-7-O-[2-(beta-D-apiosyl)-beta-D-glucoside], and luteolin-7-O-[2-(beta-D-apiosyl)-6-malonyl-beta-D-glucoside]) prepared from green pepper leaves as well as luteolin aglycone were orally administered to rats. Regardless of the administered luteolin form, luteolin glucuronides were mainly detected from plasma and organs. Subsequently, luteolin aglycone, the most absorbed form of luteolin in rats, was orally administered to humans. As a result, luteolin-3'-O-sulfate was mainly identified from plasma, suggesting that not only luteolin form but also animal species affect the absorption and metabolism of luteolin. When LPS-treated RAW264.7 cells were treated with luteolin glucuronides and luteolin sulfate (the characteristic metabolites identified from rats and humans, respectively), the different luteolin conjugates were metabolized in different ways, suggesting that such difference in metabolism results in their difference in anti-inflammatory effects.

  DOI：

  10.1021/acs.jafc.8b03273

文献信息

• Ovipositional Deterrent in the Sweet Pepper,<i>Capsicum annuum</i>, at the Mature Stage against<i>Liriomyza trifolii</i>(Burgess)
  作者：Takehiro KASHIWAGI、Yoh HORIBATA、Daniel Bisrat MEKURIA、Shin-ich TEBAYASHI、Chul-Sa KIM

  DOI：10.1271/bbb.69.1831

  日期：2005.1

  Liriomyza trifolii (Burgess), the American serpentine leafminer fly, is well known as a serious pest throughout the world. This insect attack over 21 different plant families including solanaceae plants. The mature sweet pepper, Capsicum annuum (Solanaceae), however, shows resistance to this leafminer fly. This resistance is based on the ovipositional deterrent in the sweet pepper leaf against the fly species. Based on bioassay-guided fractionation, luteolin 7-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside was isolated and identified as the ovipositional deterrent against this insect species. This compound completely deterred L. trifolii females from laying their eggs on a host plant leaf treated at 4.90 μg/cm2.

  Liriomyza trifolii (Burgess) 是一种美国蛇纹石潜叶蝇，是全世界众所周知的严重害虫。这种昆虫会侵害 21 个不同的植物科，包括茄科植物。不过，成熟的甜椒辣椒（茄科）对这种潜叶蝇具有抗性。这种抗性是基于甜椒叶片中的卵巢对这种蝇类的威慑力。根据生物测定指导下的分馏，分离并鉴定出木犀草素 7-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside，作为对这种昆虫的产卵阻遏剂。这种化合物能完全阻止 L. trifolii 雌虫在以 4.90 μg/cm2 浓度处理的寄主植物叶片上产卵。
• Absorption and Metabolism of Luteolin in Rats and Humans in Relation to <i>in Vitro</i> Anti-inflammatory Effects
  作者：Natsumi Hayasaka、Naoki Shimizu、Toshikazu Komoda、Satoshi Mohri、Tojiro Tsushida、Takahiro Eitsuka、Teruo Miyazawa、Kiyotaka Nakagawa

  DOI：10.1021/acs.jafc.8b03273

  日期：2018.10.31

  Luteolin is a flavonoid present in plants in the form of aglycone or glucosides. In this study, luteolin glucosides (i.e., luteolin-7-O-beta-D-glucoside, luteolin-7-O-[2-(beta-D-apiosyl)-beta-D-glucoside], and luteolin-7-O-[2-(beta-D-apiosyl)-6-malonyl-beta-D-glucoside]) prepared from green pepper leaves as well as luteolin aglycone were orally administered to rats. Regardless of the administered luteolin form, luteolin glucuronides were mainly detected from plasma and organs. Subsequently, luteolin aglycone, the most absorbed form of luteolin in rats, was orally administered to humans. As a result, luteolin-3'-O-sulfate was mainly identified from plasma, suggesting that not only luteolin form but also animal species affect the absorption and metabolism of luteolin. When LPS-treated RAW264.7 cells were treated with luteolin glucuronides and luteolin sulfate (the characteristic metabolites identified from rats and humans, respectively), the different luteolin conjugates were metabolized in different ways, suggesting that such difference in metabolism results in their difference in anti-inflammatory effects.