deoxyradicinin | 21593-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: deoxyradicinin
• 英文别名: (E)-2-methyl-7-(prop-1-en-1-yl)-2,3-dihydropyrano[4,3-b]pyran-4,5-dione；(±)-3-deoxyradicinin；(+/-)-Deoxyradicinin；2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
• CAS: 21593-16-8
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: SHGIAYIFKLLQOL-ONEGZZNKSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  372.9±41.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  deoxyradicinin 在 碘苯二乙酸 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 生成 3-epi-radicinin
  参考文献：
  名称：

  Synthesis of Deoxyradicinin, an Inhibitor of Xylella fastidiosa and Liberibacter crescens, a Culturable Surrogate for Candidatus Liberibacter asiaticus

  摘要：

  Pierce's disease of grapevine and citrus huanglongbing are caused by the bacterial pathogens Xylella fastidiosa and Candidatus Liberibacter asiaticus (CLas), respectively. Both pathogens reside within the plant vascular system, occluding water and nutrient transport, leading to a decrease in productivity and fruit marketability and ultimately death of their hosts. Field observations of apparently healthy plants in disease-affected vineyards and groves led to the hypothesis that natural products from endophytes may inhibit these bacterial pathogens. Previously, we showed that the natural product radicinin from Cochliobolus sp. inhibits X. fastidiosa. Herein we describe a chemical synthesis of deoxyradicinin and establish it as an inhibitor of both X. fastidiosa and Liberibacter crescens, a culturable surrogate for CLas. The key to this three-step route is a zinc-mediated enolate C-acylation, which allows for direct introduction of the propenyl side chain without extraneous redox manipulations.

  DOI：

  10.1021/acs.jnatprod.9b01207
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 正丁基锂 、 四氯化钛 、 戴斯-马丁氧化剂 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 1,1,2,2-四氯乙烷 为溶剂， 反应 8.75h， 生成 deoxyradicinin
  参考文献：
  名称：

  Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin

  摘要：

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。

  DOI：

  10.3390/molecules24173193

文献信息

• [EN] CITRUS HUANGLONGBING THERAPEUTIC COMPOUNDS<br/>[FR] COMPOSÉS THÉRAPEUTIQUES POUR LE HUANGLONGBING DES AGRUMES
  申请人：UNIV CALIFORNIA

  公开号：WO2021150951A1

  公开（公告）日：2021-07-29

  Certain embodiments of the invention provide a method of inhibiting Candidatus Liberibacter asiaticus (CLas) growth and/or treating a CLas infection (e.g., Huanglongbing) in a plant, comprising introducing to the plant at least one compound selected from the group consisting of: a cladosporol compound, a radicinin compound (e.g., a compound of formula (I)), and an epicoccamide compound, or a salt thereof. This present invention also provides methods of screening or identifying CLas inhibitory compounds.

  本发明的某些实施例提供了一种抑制亚洲型解脱假单胞菌（CLas）生长和/或治疗植物中CLas感染（例如黄龙病）的方法，包括向植物引入来自以下组合中至少一种化合物：一种克拉多斯孢醇化合物、一种雷地西宁化合物（例如，式（I）的化合物）和一种史高氏菌素化合物，或其盐。本发明还提供了筛选或识别CLas抑制化合物的方法。
• Phytotoxins from Alternaria helianthi: radicinin, and the structures of deoxyradicinol and radianthin
  作者：Beni Tal、David J. Robeson、Basil A. Burke、Arne J. Aasen

  DOI：10.1016/s0031-9422(00)84885-2

  日期：1985.1

  Abstract A novel compound, radianthin, with phytotoxic activity was isolated from liquid cultures of Alternaria helianthi and identified as a pyrone related to radicinin. A second metabolite was identified as radicinin itself while deoxyradicinol is described for the first time as a natural product.

  摘要 从 Alternaria helianthi 的液体培养物中分离出一种具有植物毒性活性的新型化合物 radianthin，并被鉴定为与 radicinin 相关的吡喃酮。第二种代谢物被鉴定为 radicinin 本身，而 deoxyradicinol 首次被描述为天然产物。
• 3-Epideoxyradicinol and the biosynthesis of deoxyradicinin
  作者：David J. Robeson、Gary A. Strobel

  DOI：10.1016/s0031-9422(00)85021-9

  日期：1984.4
• Synthesis of Deoxyradicinin, an Inhibitor of <i>Xylella fastidiosa</i> and <i>Liberibacter crescens</i>, a Culturable Surrogate for <i>Candidatus</i> Liberibacter asiaticus
  作者：Connor A. Brandenburg、Claudia A. Castro、Alex A. Blacutt、Elizabeth A. Costa、Kyler C. Brinton、Diana W. Corral、Christopher L. Drozd、M. Caroline Roper、Philippe E. Rolshausen、Katherine N. Maloney、Jonathan W. Lockner

  DOI：10.1021/acs.jnatprod.9b01207

  日期：2020.6.26

  Pierce's disease of grapevine and citrus huanglongbing are caused by the bacterial pathogens Xylella fastidiosa and Candidatus Liberibacter asiaticus (CLas), respectively. Both pathogens reside within the plant vascular system, occluding water and nutrient transport, leading to a decrease in productivity and fruit marketability and ultimately death of their hosts. Field observations of apparently healthy plants in disease-affected vineyards and groves led to the hypothesis that natural products from endophytes may inhibit these bacterial pathogens. Previously, we showed that the natural product radicinin from Cochliobolus sp. inhibits X. fastidiosa. Herein we describe a chemical synthesis of deoxyradicinin and establish it as an inhibitor of both X. fastidiosa and Liberibacter crescens, a culturable surrogate for CLas. The key to this three-step route is a zinc-mediated enolate C-acylation, which allows for direct introduction of the propenyl side chain without extraneous redox manipulations.
• Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin
  作者：Giulia Marsico、Maria Sabrina Ciccone、Marco Masi、Fabrizio Freda、Massimo Cristofaro、Antonio Evidente、Stefano Superchi、Patrizia Scafato

  DOI：10.3390/molecules24173193

  日期：——

  A novel synthetic strategy for obtainment of (±)-3-deoxyradicinin (2) is reported. This synthetic methodology is more efficient than those previously reported in the literature and also shows higher versatility towards the introduction of different side-chains at both C-7 and C-2. The obtained compound (±)-2 shows phytotoxicity against the grass-weed buffelgrass comparable to that of the natural phytotoxin radicinin (1). Therefore, (±)-2 can constitute a more practical synthetic alternative to 1 as bioherbicide for buffelgrass control.

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。