5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al | 62777-81-5

• 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: 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al
• 英文别名: apo-12'-violaxanthal；apo-12-violaxanthal；Persicaxanthal；(3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al；(2E,4E,6E,8E,10E,12E)-13-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal
• CAS: 62777-81-5
• 化学式: C₂₅H₃₄O₃
• 分子量: 382.543
• InChiKey: CAXVJDRXJFKYQP-LKODNMENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 Persicaxanthin
  参考文献：
  名称：

  对映体纯的载载紫黄嘌呤酸，油和麦芽酒（二黄嘌呤，sensensiaxanthin和β-citraurin环氧化合物）及其呋喃类重排产物的合成

  摘要：

  对映体纯载载载紫黄嘌呤酸，载载紫黄嘌呤醇和载载紫黄嘌呤类化合物（包括过高黄嘌呤，Sinensiaxanthin和β-Citraurin环氧化合物）及其呋喃重排产物的合成

  DOI：

  10.1002/hlca.19880710817
• 作为产物：
  描述：

  Persicaxanthal-dimethyl-acetal 在 对甲苯磺酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 0.02h， 生成 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al
  参考文献：
  名称：

  对映体纯的载载紫黄嘌呤酸，油和麦芽酒（二黄嘌呤，sensensiaxanthin和β-citraurin环氧化合物）及其呋喃类重排产物的合成

  摘要：

  对映体纯载载载紫黄嘌呤酸，载载紫黄嘌呤醇和载载紫黄嘌呤类化合物（包括过高黄嘌呤，Sinensiaxanthin和β-Citraurin环氧化合物）及其呋喃重排产物的合成

  DOI：

  10.1002/hlca.19880710817

文献信息

• Carotenoid metabolism and the biosynthesis of abscisic acid
  作者：Andrew D. Parry、Roger Horgan

  DOI：10.1016/0031-9422(91)85258-2

  日期：1991.1

  origin of abscisic acid. Several apo-carotenoids, putative by-products of abscisic acid biosynthesis, were synthesised by chemical oxidation but were not detected in plant extracts. In vitro, lipoxygenase cleaved neoxanthin and violaxanthin down to small ( \ C13) fragments. It may be that in vivo any apo-carotenoids formed by the specific cleavage of 9′-cis-neoxanthin, during abscisic acid biosynthesis

  摘要 暴露于光后，在氟啶酮处理的黄化番茄和菜豆幼苗中，全反式紫黄质转化为 9'-顺式新黄质。氧化氘标记实验的结果支持了这种前体/产物关系，并为脱落酸的起源提供了进一步的证据。几种 apo-carotenoids 是脱落酸生物合成的假定副产品，通过化学氧化合成，但未在植物提取物中检测到。在体外，脂肪氧化酶将新黄质和紫黄质切割成小的 (\C13) 片段。可能在体内，在脱落酸生物合成过程中，通过 9'-顺式新黄质的特异性裂解形成的任何 apo-类胡萝卜素都被脂氧合酶或类似的酶迅速代谢。
• The constitution and absolute stereochemistry of persicaxanthin
  作者：Péter Molnár、József Szabolcs、Lajos Radics

  DOI：10.1016/s0031-9422(00)81842-7

  日期：1987.4

  Abstract Persicaxanthin, isolated from the fruits of peach, has been obtained in crystalline form. By spectroscopic (MS, 1H NMR and CD) methods, its constitution and absolute stereochemistry have been determined as (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-d The structural conclusions have received full support by comparison with semi-synthetic persicaxanthin obtained from natural violaxanthin.

  摘要 从桃子果实中分离出的桃黄质已以结晶形式获得。通过光谱（MS，1H NMR和CD）方法，其组成和绝对立体化学已确定为（3S,5R,6S）-5,6-epoxy-3-hydroxy-5,6-d 结构结论已得到充分通过与从天然紫黄质中获得的半合成桃黄质进行比较来支持。
• The 9- <i>cis</i> -epoxycarotenoid cleavage reaction is the key regulatory step of abscisic acid biosynthesis in water-stressed bean
  作者：Xiaoqiong Qin、Jan A. D. Zeevaart

  DOI：10.1073/pnas.96.26.15354

  日期：1999.12.21

  Abscisic acid (ABA), a cleavage product of carotenoids, is involved in stress responses in plants. A well known response of plants to water stress is accumulation of ABA, which is caused by de novo synthesis. The limiting step of ABA biosynthesis in plants is presumably the cleavage of 9-cis-epoxycarotenoids, the first committed step of ABA biosynthesis. This step generates the C(15) intermediate xanthoxin

  脱落酸 (ABA) 是类胡萝卜素的裂解产物，参与植物的应激反应。众所周知，植物对水分胁迫的反应是 ABA 的积累，这是由从头合成引起的。植物中 ABA 生物合成的限制步骤可能是 9-顺式环氧类胡萝卜素的裂解，这是 ABA 生物合成的第一个关键步骤。此步骤生成 C(15) 中间体黄毒素和 C(25)-类胡萝卜素。从枯萎的菜豆 (Phaseolus vulgaris L.) 叶子中克隆了 cDNA，PvNCED1。 2、398 bp 全长 PvNCED1 的 ORF 为 615 个氨基酸，编码 68 kDa 蛋白质。 PvNCED1 蛋白被输入叶绿体，并与类囊体结合。重组蛋白PvNCED1催化9-顺式紫黄质和9'-顺式新黄质的裂解，因此该酶被称为9-顺式环氧类胡萝卜素双加氧酶。当分离的豆叶受到水分胁迫时，ABA 积累之前 PvNCED1 mRNA 和蛋白质水平大幅增加。相反，胁迫叶片的再水化导致
• Specific Oxidative Cleavage of Carotenoids by VP14 of Maize
  作者：Steven H. Schwartz、Bao Cai Tan、Douglas A. Gage、Jan A. D. Zeevaart、Donald R. McCarty

  DOI：10.1126/science.276.5320.1872

  日期：1997.6.20

  The plant growth regulator abscisic acid (ABA) is formed by the oxidative cleavage of an epoxy-carotenoid. The synthesis of other apocarotenoids, such as vitamin A in animals, may occur by a similar mechanism. In ABA biosynthesis, oxidative cleavage is the first committed reaction and is believed to be the key regulatory step. A new ABA-deficient mutant of maize has been identified and the corresponding gene, Vp14 , has been cloned. The recombinant VP14 protein catalyzes the cleavage of 9- cis -epoxy-carotenoids to form C ₂₅ apo-aldehydes and xanthoxin, a precursor of ABA in higher plants.

  植物生长调节剂脱落酸（ABA）是由环氧类胡萝卜素的氧化裂解形成的。其他类胡萝卜素的合成，如动物中的维生素A，可能以类似的机制发生。在ABA生物合成中，氧化裂解是第一个确定的反应，并被认为是关键的调节步骤。玉米的一个新的ABA缺陷突变体已经被鉴定出来，并且相应的基因Vp14已经被克隆。重组VP14蛋白催化9-cis-环氧类胡萝卜素的裂解，形成C25的脱落醛和黄酮酸，这是高等植物ABA的前体。
• Genetic control of abscisic acid biosynthesis in maize
  作者：Bao Cai Tan、Steven H. Schwartz、Jan A. D. Zeevaart、Donald R. McCarty

  DOI：10.1073/pnas.94.22.12235

  日期：1997.10.28

  Abscisic acid (ABA), an apocarotenoid synthesized from cleavage of carotenoids, regulates seed maturation and stress responses in plants. The viviparous seed mutants of maize identify genes involved in synthesis and perception of ABA. Two alleles of a new mutant, viviparous14 (vp14), were identified by transposon mutagenesis. Mutant embryos had normal sensitivity to ABA, and detached leaves of mutant seedlings showed markedly higher rates of water loss than those of wild type. The ABA content of developing mutant embryos was 70% lower than that of wild type, indicating a defect in ABA biosynthesis. vp1 4 embryos were not deficient in epoxy-carotenoids, and extracts of vp14 embryos efficiently converted the carotenoid cleavage product, xanthoxin, to ABA, suggesting a lesion in the cleavage reaction. vp14 was cloned by transposon tagging. The VP14 protein sequence is similar to bacterial lignostilbene dioxygenases (LSD). LSD catalyzes a double-bond cleavage reaction that is closely analogous to the carotenoid cleavage reaction of ABA biosynthesis. Southern blots indicated a family of four to six related genes in maize. The Vp14 mRNA is expressed in embryos and roots and is strongly induced in leaves by water stress. A family of Vp14 -related genes evidently controls the first committed step of ABA biosynthesis. These genes are likely to play a key role in the developmental and environmental control of ABA synthesis in plants.

  脱落酸（ABA）是一种从类胡萝卜素分解合成的apo类胡萝卜素，调节植物的种子成熟和应对压力反应。玉米的胚胎萌发突变体确定了与ABA合成和感知有关的基因。通过转座子诱变鉴定了一个新突变体vp14的两个等位基因。突变胚胎对ABA具有正常敏感性，突变苗的脱落叶比野生型的水分流失率明显更高。发育中的突变胚胎ABA含量比野生型低70％，表明ABA生物合成存在缺陷。vp14胚胎中不缺乏环氧类胡萝卜素，vp14胚胎的提取物有效地将类胡萝卜素分解产物xanthoxin转化为ABA，表明存在分解反应的损伤。vp14通过转座子标记克隆。VP14蛋白序列类似于细菌木材苯亚乙烯双加氧酶（LSD）。LSD催化的双键分解反应与ABA生物合成的类胡萝卜素分解反应密切类似。Southern印迹表明在玉米中有4到6个相关基因家族。vp14 mRNA在胚胎和根中表达，并在叶片中受到水分压力的强烈诱导。vp14相关基因家族显然控制ABA生物合成的第一步。这些基因可能在植物ABA合成的发育和环境控制中发挥关键作用。