3-epi-radicinol | 189948-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-epi-radicinol
• 英文别名: (2S,3S,4S)-3,4-dihydroxy-2-methyl-7-[(1E)-prop-1-en-1-yl]-2H,3H,4H,5H-pyrano[4,3-b]pyran-5-one；(2S,3S,4S)-3,4-dihydroxy-2-methyl-7-[(E)-prop-1-enyl]-3,4-dihydro-2H-pyrano[3,2-c]pyran-5-one
• CAS: 189948-06-9
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: RMDHRYWEFJLSJF-DPYOFBQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-epi-radicinol 在 potassium dihydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以4.7%的产率得到(2S,3S,4S)-3,4-Dihydroxy-2-methyl-7-((2R,3R)-3-methyl-oxiranyl)-3,4-dihydro-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  Phytotoxins and related metabolites produced by Bipolaris coicis, the pathogen of job's tears

  摘要：

  Four metabolites were isolated and characterized from the phytopathogenic fungus Bipolaris colds H-13-3. Radicinin and its diastereomer were phytotoxic against Job's tears (Coix lachryma-jobi), a host of this fungus, but a diastereomer of radicinol and its epoxide were not phytotoxic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(96)00804-7
• 作为产物：
  描述：

  3-epi-radicinin 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以1.2 mg的产率得到3-epi-radicinol
  参考文献：
  名称：

  Phytotoxins and related metabolites produced by Bipolaris coicis, the pathogen of job's tears

  摘要：

  Four metabolites were isolated and characterized from the phytopathogenic fungus Bipolaris colds H-13-3. Radicinin and its diastereomer were phytotoxic against Job's tears (Coix lachryma-jobi), a host of this fungus, but a diastereomer of radicinol and its epoxide were not phytotoxic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(96)00804-7

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。
• Phytotoxic Activity and Structure–Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)
  作者：Masi、Freda、Clement、Cimmino、Cristofaro、Meyer、Evidente

  DOI：10.3390/molecules24152793

  日期：——

  structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization

  Radicinin (1)，是一种真菌二氢吡喃并吡喃-4,5-二酮，与一些类似物一起分离，即 3-epi-radicinin、radicinol、3-epi-radicinol 和 cochliotoxin (2-5)，从培养基的培养滤液中分离出来。真菌 Cochliobolus australiensis，一种水牛草（Cenchrus ciliaris）的叶面病原体，是北美的一种入侵杂草。在不同的代谢物中，1 显示出针对宿主植物的靶标特异性活性，并且对斑马鱼胚胎没有毒性，这促进了其在开发天然生物除草剂配方以管理水牛草方面的潜在用途。这些数据和1的独特结构特征建议进行构效关系研究，制备一些关键的半合成衍生物并测试它们的植物毒性。特别地，对溴苯甲酰基、5-叠氮基戊酰基、硬脂酰基、radicinin的甲磺酰酯和乙酰酯以及3-epi-radicinin的单乙酰酯、radicinol及其3差向异构
• Fungi antagonistic to Xylella fastidiosa
  申请人：The Regents of the University of California

  公开号：US10238118B2

  公开（公告）日：2019-03-26

  The disclosure describes fungal organisms and preparations useful for inhibiting infection by Xylella sp. and in the treatment of Pierce's Disease.

  本公开描述了真菌生物和制剂，可用于抑制 Xylella sp.的感染和治疗皮尔斯病。
• FUNGI ANTAGONISTIC TO XYLELLA FASTIDIOSA
  申请人：Rolshausen Philippe

  公开号：US20120282233A1

  公开（公告）日：2012-11-08

  The disclosure describes fungal organisms and preparations useful for inhibiting infection by Xylella sp. and in the treatment of Pierce's Disease.
• US9433219B2
  申请人：——

  公开号：US9433219B2

  公开（公告）日：2016-09-06