all-E-apo-13-zeaxanthinone

• 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: all-E-apo-13-zeaxanthinone
• 英文别名: (3R)-3-hydroxy-13-apo-β-caroten-13-one；zaxinone；all-E-3-hydroxy-13-apo-β-caroten-13-one；3-OH-β-apo-13-carotenone；apo-13-zeaxanthinone；(3E,5E,7E)-8-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-6-methylocta-3,5,7-trien-2-one
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: JLNMEHQAHDSEEE-YSAUQHOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  apo-10'-zeaxanthinal 在 rice dioxygenase A, zaxinone synthase 作用下， 生成 (2E,4E,6E)-4-methylocta-2,4,6-trienedial 、 all-E-apo-13-zeaxanthinone
  参考文献：
  名称：

  [EN] PLANT GROWTH PROMOTER WITH STRIGOLACTONES REGULATION ACTIVITIES
  [FR] PROMOTEUR DE CROISSANCE VÉGÉTALE AYANT DES ACTIVITÉS DE RÉGULATION DES STRIGOLACTONES

  摘要：

  The present invention uses compound 3-OH-β-apo-13-carotenone (zaxinone) as a negative regulator of the plant hormone strigolactones (SLs). The compound 3-OH-β-apo-13- carotenone is a positive growth regulator which triggers the formation of crown roots and promotes growth in size and number of roots and shoots. Disclosed herein is a method of using 3-OH-β-apo-13-carotenone as a growth-promoting compound for cereal, grain and vegetable crops. The 3-OH-β-apo-13-carotenone compounds is also a negative regulator of strigolactone biosynthesis and release. Disclosed herein is a method of combating root parasitic weeds affecting cereal, grain and vegetable crops. Application of 3-OH-β-apo-13-carotenone to plant growth media down-regulates strigolactone production in cereal, grain and vegetable crops preventing root parasitic weed infestation of the crops by inhibiting germination of parasitic weed seeds.

  公开号：

  WO2019003089A1

文献信息

• Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers
  申请人：Khachik Frederick

  公开号：US20090264681A1

  公开（公告）日：2009-10-22

  (3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C 15 +C 10 +C 15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

  (3R,3′R,6′R)-叶黄素和(3R,3′R)-玉米黄质是两种膳食类胡萝卜素，广泛存在于美国常见的大多数水果和蔬菜中。这些类胡萝卜素在人类血浆、主要器官和眼部组织中积累。在过去的十年里，许多流行病学和实验研究表明，叶黄素和玉米黄质在预防年龄相关性黄斑变性（AMD）中起着重要作用，这是美国和西方世界导致失明的主要原因。本发明提供了一种从商业可获得的（rac）-α-离子酮通过C15+C10+C15偶联策略合成(3R,3′R,6′R)-叶黄素及其立体异构体的方法。此外，本发明还提供了一种获得具有3-羟基-ε-末端基团的光学活性类胡萝卜素前体的方法，否则这些类胡萝卜素前体很难合成。用于合成叶黄素及其立体异构体的方法是简单明了的，并具有商业化潜力。
• The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids
  作者：Daniel Scherzinger、Erdmann Scheffer、Cornelia Bär、Hansgeorg Ernst、Salim Al-Babili

  DOI：10.1111/j.1742-4658.2010.07873.x

  日期：2010.11

  acid, is initiated by the β‐carotene cleavage oxygenases I and II catalyzing either a central or an excentric cleavage of β‐carotene, respectively. The M. tuberculosis ORF Rv0654 codes for a putative carotenoid oxygenase conserved in other mycobacteria. In the present study, we investigated the corresponding enzyme, here named M. tuberculosis carotenoid cleavage oxygenase (MtCCO). Using heterologously

  结核分枝杆菌是结核的病原体，被认为缺乏类胡萝卜素，类胡萝卜素是广泛存在的色素，具有重要的功能，可作为自由基清除剂和类胡萝卜素的来源。在哺乳动物中，包括视黄酸在内的类胡萝卜素的合成是由β-胡萝卜素裂解加氧酶I和II分别催化β-胡萝卜素的中心裂解或偏心裂解引起的。在结核分枝杆菌ORF Rv0654编码推定的类胡萝卜素氧保守在其它分枝杆菌。在本研究中，我们研究了相应的酶，在这里称为结核分枝杆菌类胡萝卜素裂解加氧酶（MtCCO）。使用异源表达和纯化的蛋白质，我们表明MtCCO在体外可转化几种类胡萝卜素和类胡萝卜素。此外，产品鉴定表明，与其他类胡萝卜素加氧酶不同，MtCCO裂解中央C15-C15'和C13-C14位置的偏心双键，从而导致视网膜（C 20），β-​​载脂蛋白14 '-胡萝卜素（C 22）和β-载脂蛋白13-胡萝卜素（C 18）和β-胡萝卜素的相应羟基化产物，以及玉米黄质和叶黄素的相应羟基化产物。此外，该酶还切割3
• Plant growth promoter with strigolactones regulation activities
  申请人：King Abdullah University of Science and Technology

  公开号：US11399538B2

  公开（公告）日：2022-08-02

  The present invention uses compound 3-OH-β-apo-13-carotenone (zaxinone) as a negative regulator of the plant hormone strigolactones (SLs). The compound 3-OH-β-apo-13-carotenone is a positive growth regulator which triggers the formation of crown roots and promotes growth in size and number of roots and shoots. Disclosed herein is a method of using 3-OH-β-apo-13-carotenone as a growth-promoting compound for cereal, grain and vegetable crops. The 3-OH-β-apo-13-carotenone compounds is also a negative regulator of strigolactone biosynthesis and release. Disclosed herein is a method of combating root parasitic weeds affecting cereal, grain and vegetable crops. Application of 3-OH-β-apo-13-carotenone to plant growth media down-regulates strigolactone production in cereal, grain and vegetable crops preventing root parasitic weed infestation of the crops by inhibiting germination of parasitic weed seeds.

  本发明使用化合物 3-OH-β-apo-13-carotenone（ZAXINONE）作为植物激素糙果内酯（SLs）的负调节剂。化合物 3-OH-β-apo-13-carotenone 是一种正生长调节剂，它能引发冠状根的形成，并促进根和芽的大小和数量的增长。本文公开了一种将 3-OH-β-apo-13- 胡萝卜素酮用作谷物、粮食和蔬菜作物生长促进化合物的方法。3-OH-β-apo-13- 胡萝卜烯酮化合物还是绞股蓝内酯生物合成和释放的负调节剂。本文公开了一种防治影响谷物、粮食和蔬菜作物的根部寄生杂草的方法。在植物生长介质中施用 3-OH-β-apo-13- 胡萝卜素酮可降低谷类、谷物和蔬菜作物中的赤霉内酯产量，通过抑制寄生杂草种子的发芽，防止根部寄生杂草侵染作物。
• PLANT GROWTH PROMOTER WITH STRIGOLACTONES REGULATION ACTIVITIES
  申请人：King Abdullah University of Science and Technology

  公开号：US20210360918A1

  公开（公告）日：2021-11-25

  The present invention uses compound 3-OH-β-apo-13-carotenone (zaxinone) as a negative regulator of the plant hormone strigolactones (SLs). The compound 3-OH-β-apo-13-carotenone is a positive growth regulator which triggers the formation of crown roots and promotes growth in size and number of roots and shoots. Disclosed herein is a method of using 3-OH-β-apo-13-carotenone as a growth-promoting compound for cereal, grain and vegetable crops. The 3-OH-β-apo-13-carotenone compounds is also a negative regulator of strigolactone biosynthesis and release. Disclosed herein is a method of combating root parasitic weeds affecting cereal, grain and vegetable crops. Application of 3-OH-β-apo-13-carotenone to plant growth media down-regulates strigolactone production in cereal, grain and vegetable crops preventing root parasitic weed infestation of the crops by inhibiting germination of parasitic weed seeds.
• COMPOUNDS AND METHODS FOR PROMOTING PLANT GROWTH
  申请人：King Abdullah University of Science and Technology

  公开号：US20220400669A1

  公开（公告）日：2022-12-22

  Disclosed herein are compounds and methods for promoting plant growth. Formulations containing one or more disclosed compounds or salts thereof, and one or more excipients are disclosed. The formulation adjuvant can be a solid carrier, a liquid carrier, or a surface-active agent. Methods for promoting plant growth typically includes applying one or more formulations to a plant, a plant part, or a growing site of plant. The plant can be a cereal, grain, or vegetable plant. The plant part can be seed or seedling of a plant. The growing site of plant can be soil before, during, or after the plant is planted or a growing medium. In some embodiments, the one or more compounds or salts thereof in the one or more formulations are in an effective amount to decrease biosynthesis and release of strigolactone plant hormones from the plant.