(±)-orobanchol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (±)-orobanchol
• 英文别名: (3E,3aS,4S,8bS)-4-hydroxy-8,8-dimethyl-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-3a,4,5,6,7,8b-hexahydroindeno[1,2-b]furan-2-one
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: CDBBMEYPRMUMTR-XCPYXGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (±)-orobanchol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Fabacyl acetate, a germination stimulant for root parasitic plants from Pisum sativum

  摘要：

  A germination stimulant, fabacyl acetate. was purified from root exudates of pea (Pisum sativum L.) and its structure was determined as ent-2'-epi-4a,8a-epoxyorobanchyl acetate [(3aR,4R,4aR,8bS,E)-4a,8a-epoxy-8,8-dimethyl-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-2-oxo- 3,3a,4,5,6,7,8,8b-decahydro-2H-indeno[1,2-b]furan-4-yl acetate], by 1D and 2D NMR spectroscopic, ESI-and E1-MS spectrometric, X-ray crystallographic analyses, and by comparing the H-1 NMR spectroscopic data and relative retention times (RRt) in LC-MS and CC-MS with those of synthetic standards prepared from (+)-orobanchol and (+)-2'-epiorobanchol. The H-1 NMR spectroscopic data and RRt of fabacyl acetate were identical with those of an isomer prepared from (+)-2'-epiorobanchol except for the opposite sign in CD spectra. This is the first natural ent-strigolactone containing an epoxide group. Fabacyl acetate was previously detected in root exudates of other Fabaceae plants including faba bean (Vicia faba Q and alfalfa (Medicago sativa L). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.12.013
• 作为产物：
  描述：

  ((1SR,2RS,4RS)-1,4-dihydroxy-7,7-dimethyl-2,3,4,5,6,7-hexahydroinden-2-yl)-9,1-lactone 在 甲醇 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.5h， 生成 (±)-orobanchol
  参考文献：
  名称：

  通过烯丙基重排合成发芽刺激剂 (±)-Orobanchol 和 (±)-Strigol

  摘要：

  (+)-Orobanchol 和 (+)-strigol 是寄生杂草 Striga 和 Orobanche 种子自然产生的发芽刺激物。本文描述了通过烯丙基重排乳酮 (±)-12 和 (±)-14 的高效合成 (±)-orobanchol 和 (±)-strigol 的方法。

  DOI：

  10.1055/s-2000-8231

文献信息

• Synthesis of (+)-Strigol and (+)-Orobanchol, the Germination Stimulants, and Their Stereoisomers by Employing Lipase-Catalyzed Asymmetric Acetylationas the Key Step
  作者：Kouichi Hirayama、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2211::aid-ejoc2211>3.0.co;2-o

  日期：1999.9

  The potent seed germination stimulants (+)-strigol (1), (+)-orobanchol (2) and their stereoisomers [2′-epistrigol (1′), ent-1, ent-1′, 2′-epiorobanchol (2′), 4-epiorobanchol (2′′) and 4, 2′-bisepiorobanchol (2′′′)] were prepared from the enantiomers of 3, which were obtainable by lipase-catalyzed enantiomer separation of (±)-3.

  强效种子萌发刺激剂 (+)-strigol (1), (+)-orobanchol (2) 及其立体异构体 [2'-epistrigol (1'), ent-1, ent-1', 2'-epiorobanchol (2) '), 4-epiorobanchol (2'') 和 4, 2'-bisepiorobanchol (2''')] 是从 3 的对映异构体制备的，它们可通过 (±)-3 的脂肪酶催化对映异构体分离获得。
• Synthesis of racemic orobanchols via acid-mediated cascade cyclization: Insight into the process of BC-ring formation in strigolactone biosynthesis
  作者：Nanami Shiotani、Takatoshi Wakabayashi、Yusuke Ogura、Hironori Okamura、Yukihiro Sugimoto、Hirosato Takikawa

  DOI：10.1016/j.tetlet.2021.153469

  日期：2021.11

  racemic orobanchols was performed in the same way as in our previous study, which demonstrated that the BC-ring formation is possible “in flask” via acid-mediated cascade cyclization. The results strongly suggested that the mechanism of acid-mediated BC-ring formation may be based on the conrotatory electrocyclic reaction, and may provide significant insights into the process of BC-ring formation in

  独脚金内酯是一类类胡萝卜素，已知用作根际信息化合物和植物激素。典型的独脚金内酯由三环内酯（ABC 环）和丁烯内酯部分（D 环）组成，它们的生物合成已被广泛研究。然而，BC-环的形成过程还有待阐明。以与我们之前的研究相同的方式将 18-氧代卡拉内酯衍生物转化为外消旋 orobanchols，这表明 BC 环的形成是可能的“在烧瓶中”通过酸介导的级联环化。结果强烈表明，酸介导的 BC 环形成机制可能基于旋转电环反应，并可能为独脚金内酯生物合成中 BC 环形成过程提供重要见解。
• Synthesis and Structure of Orobanchol, the Germination Stimulant forOrobanche minor
  作者：Junichi Matsui、Takao Yokota、Masahiko Bando、Yasutomo Takeuchi、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2201::aid-ejoc2201>3.0.co;2-q

  日期：1999.9

  The structure of orobanchol, a new seed germination stimulant for clover broomrape (Orobanche minor), was proposed as 5a (tentative absolute configuration) on the basis of GC-MS comparison of the natural product with several synthetic compounds [(±)-4a–(±)-4h, (±)-5a and (±)-5b]. All of the synthetic compounds showed significant seed germination activities for Orobanche minor and witchweed (Striga asiatica)

  基于天然产物与几种合成化合物的 GC-MS 比较 [(±)-4a– (±)-4h、(±)-5a 和 (±)-5b]。所有合成化合物都显示出对 Orobanche minor 和金缕梅 (Striga asiatica) 的显着种子萌发活性。
• Novel and efficient stereoselective synthesis of (±)-orobanchol, a representative canonical strigolactone, based on acid-mediated cascade cyclization
  作者：Kiyono Uchida、Yusuke Ogura、Hironori Okamura、Yukihiro Sugimoto、Hirosato Takikawa

  DOI：10.1016/j.tetlet.2023.154454

  日期：2023.3

  so far, and both have room for improvement in selectivity and overall efficiency. We report a novel and efficient stereoselective synthesis of (±)-orobanchol using acid-mediated cascade cyclization as a key step. This cascade cyclization is analogous to that occurring in planta and is understood to involve a conrotatory 4π-electrocyclic reaction.

  独脚金内酯是一类被称为根际化学信息素和植物激素的类胡萝卜素，可分为规范类或非规范类。尽管长期以来，甲半酚一直被认为是具有代表性的经典独脚金内酯，但迄今为止仅报道了两种合成方法，两者在选择性和整体效率方面均有提升空间。我们报告了一种新型且高效的立体选择性合成 (±)-orobanchol，使用酸介导的级联环化作为关键步骤。这种级联环化类似于植物中发生的环化，并且被认为涉及旋转 4π-电环化反应。
• Use of strigolactones and strigolactone analogs for treating proliferative conditions
  申请人：The State of Israel, Ministry of Agriculture & Rural Development, Agricultural Research Organization (ARO)

  公开号：US10208007B2

  公开（公告）日：2019-02-19

  Compound of formula X wherein P1 is a fused-ring system comprising one 6-membered and two 5-membered rings; v indicates an S or R configuration; or individual isomers or pharmaceutically acceptable salts thereof, or mixtures thereof, in the preparation of an active agent for preventing or inhibiting cell proliferation or for inducing cell death.

  式 X 的化合物，其中 P1 是由一个 6 元环和两个 5 元环组成的融合环体系；v 表示 S 或 R 构型；或其单个异构体或药学上可接受的盐，或其混合物，用于制备防止或抑制细胞增殖或诱导细胞死亡的活性剂。