neoxanthin | 10153-97-6

• 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: neoxanthin
• 英文别名: 9'-cis-neoxanthin；(9'Z)-neoxanthin；cis-neoxanthin
• CAS: 10153-97-6；14660-91-4；17708-84-8；19254-47-8；21888-00-6；21888-01-7；21888-02-8；21888-03-9；21888-04-0；21888-05-1；21888-06-2；25493-63-4；27780-09-2；29363-88-0；30743-41-0；52949-72-1；52949-73-2；142236-46-2；142236-48-4；142236-50-8
• 化学式: C₄₀H₅₆O₄
• 分子量: 600.882
• InChiKey: PGYAYSRVSAJXTE-FTLOKQSXSA-N

物化性质

• 沸点：
  733.3±60.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• 最大波长(λmax)：
  λ: 435-439 nm Amax

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

生物活性

Neoxanthin 是一种主要存在于深绿色多叶蔬菜中的类胡萝卜素，是植物激素脱落酸的前体。它是一种有效的抗氧化剂和集光颜料，能够诱导细胞凋亡，并具有抗癌作用。

体外研究

Neoxanthin（20 μM；72小时）处理显著降低了 PC-3 细胞、DU 145 细胞和 LNCaP 细胞的存活率，分别为 10.9%、15.0% 和接近零。此外，Neoxanthin 还通过抑制 C3H10T1/2 细胞 DNA 合成来强烈抑制细胞生长。在光合生物中，Neoxanthin 是氧性光合作装置的光系统 I (PSI) 和光系统 II (PSII) 反应中心的关键成分。

体内研究

研究表明 Neoxanthin 在小鼠体内的消化道代谢情况如下：口服给予小鼠 Neoxanthin（每只40 nmol）后2小时，Neoxanthin 已出现在小鼠血浆和肝脏中。在血浆中的浓度为13.6-9.0 nM，在肝脏中的浓度为7.3-3.6 pmol/g。此外，在接受 Neoxanthin 治疗的小鼠的小肠内容物中，还检测到了 (R/S)-Neochrome 的存在。

反应信息

• 作为反应物：
  描述：

  neoxanthin 在 Tween-80 过氧乙酸 、 乙二胺四乙酸 、 sodium formate 作用下， 生成 大马士酮
  参考文献：
  名称：

  Thermal Oxidation of 9‘-cis-Neoxanthin in a Model System Containing Peroxyacetic Acid Leads to the Potent Odorant β-Damascenone

  摘要：

  The potent odorant beta-damascenone was formed directly from 9'-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. beta-Damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurring over the two sequential phases. The first was incubation with peroxyacetic acid at 60 degrees C for 90 min, and the second was at above 90 degrees C for 20 min. Only traces of beta-damascenone were formed on application of only one of the two phases. Formate and citrate solutions produced a much better environment for beta-damascenone formation than acetate and phosphate. About 7 mu g/L beta-damascenone was formed from 5.8 mg/L 9'-cis-neoxanthin under optimal experimental condition. The detailed pathway by which beta-damascenone is formed remains to be elucidated.

  DOI：

  10.1021/jf051330b
• 作为产物：
  描述：

  (15Z,9'Z)-Neoxanthin 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 neoxanthin
  参考文献：
  名称：

  （6 - [R，9' Ž）-Neoxanthin：SYNTHESE，Schmelzverhalten，Spektren UND Konformationsberechnungen

  摘要：

  （6 - [R，9' Ž）-Neoxanthin的合成，物理性质，光谱，以及在溶液中其构象的计算

  DOI：

  10.1002/hlca.19940770405

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。
• Neoflor und 6-Epineoflor aus Blüten von<i>Trollius europaeus</i>; Hochfeld-¹H-NMR-Spektren von Neoxanthin und (9′<i>Z</i>)-Neoxanthin
  作者：Edith Märki-Fischer、Conrad Hans Eugster

  DOI：10.1002/hlca.19900730608

  日期：1990.9.19

  Neoflor and 6-Epineoflor from Flowers of Trollius europaeus; Highfield 1H-NMR Spectra of (all-E)-Neoxanthin and (9′Z)-Neoxanthin

  欧洲金莲花的花朵中的新花香和6-花香花；（全-E）-新黄嘌呤和（9'Z）-新黄嘌呤的高场1 H-NMR谱
• (6R,9?Z)-Neoxanthin: Synthese, Schmelzverhalten, Spektren und Konformationsberechnungen
  作者：Andreas Baumeler、Oliver Zerbe、Roland Kunz、Conrad Hans Eugster

  DOI：10.1002/hlca.19940770405

  日期：1994.6.29

  (6R,9′Z)-Neoxanthin: Synthesis, Physical Properties, Spectra, and Calculations of Its Conformation in Solution

  （6 - [R，9' Ž）-Neoxanthin的合成，物理性质，光谱，以及在溶液中其构象的计算
• Thermal Oxidation of 9‘-<i>cis</i>-Neoxanthin in a Model System Containing Peroxyacetic Acid Leads to the Potent Odorant β-Damascenone
  作者：Yair Bezman、Itzhak Bilkis、Peter Winterhalter、Peter Fleischmann、Russell L. Rouseff、Susanne Baldermann、Michael Naim

  DOI：10.1021/jf051330b

  日期：2005.11.1

  The potent odorant beta-damascenone was formed directly from 9'-cis-neoxanthin in a model system by peroxyacetic acid oxidation and two-phase thermal degradation without the involvement of enzymatic activity. beta-Damascenone formation was heavily dependent on pH (optimum at 5.0) and temperature, occurring over the two sequential phases. The first was incubation with peroxyacetic acid at 60 degrees C for 90 min, and the second was at above 90 degrees C for 20 min. Only traces of beta-damascenone were formed on application of only one of the two phases. Formate and citrate solutions produced a much better environment for beta-damascenone formation than acetate and phosphate. About 7 mu g/L beta-damascenone was formed from 5.8 mg/L 9'-cis-neoxanthin under optimal experimental condition. The detailed pathway by which beta-damascenone is formed remains to be elucidated.