apo-8,6'-carotendial

• 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: apo-8,6'-carotendial
• 英文别名: (2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyloctadeca-2,4,6,8,10,12,14,16-octaenedial；apo-8,6′-carotendial；6,8'-Diapocarotene-6,8'-dial
• 化学式: C₂₂H₂₆O₂
• 分子量: 322.447
• InChiKey: HADDAGQXXLLFSE-VOSMWNACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  番茄红素 在 potassium permanganate 、 十六烷基三甲基溴化铵 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenal 、 apo-8,12'-carotendial 、 apo-6,12'-carotendial 、 apo-8,6'-carotendial 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  体外氧化产生的番茄红素裂解产物：表征和形成机理。

  摘要：

  这项研究的目的是生产番茄红素的体外氧化产物，这可能是体内代谢产物。番茄红素用高锰酸钾的氧化产生了一系列番茄红素降解化合物，这些化合物是由一个或两个碳-碳双键的氧化裂解产生的。获得了十一种载脂蛋白低碳脂蛋白/单糖和六种载脂蛋白-胡萝卜素，并通过HPLC-DAD-MS进行了初步鉴定。首次分离了载脂蛋白-11-冰醛和载脂蛋白8,6'-胡萝卜素，并通过（1）H NMR进行了表征。番茄红素受到金属卟啉催化的大气氧氧化，该金属卟啉是细胞色素P450酶活性中心的模型系统。形成（E）-番茄红素的（Z）-异构体，一氧化物和裂解化合物。我们提出了该系统氧化番茄红素的机理。

  DOI：

  10.1021/jf034735+

文献信息

• Fractionation and Characterization of Lycopene-Oxidation Products by LC-MS/MS (ESI)⁺: Elucidation of the Chemopreventative Potency of Oxidized Lycopene in Breast-Cancer Cell Lines
  作者：Bangalore Prabhashankar Arathi、Poorigali Raghavendra-Rao Sowmya、Gini Chempakathinal Kuriakose、Shivaprasad Shilpa、Hulikere Jagdish Shwetha、Sharath Kumar、Marisiddaiah Raju、Vallikannan Baskaran、Rangaswamy Lakshminarayana

  DOI：10.1021/acs.jafc.8b04850

  日期：2018.10.31

  Lycopene (LYC) has been correlated with the reduction of certain cancers and chronic diseases. However, the existence and biofunctionality of degraded, oxidized, and biotransformed LYC products in vivo have not been revealed. Therefore, this study aimed to screen and elucidate the potential bioactive lycopene-derived products in breast-cancer and noncancerous cells. LYC-oxidation or -cleavage products were generated using KMnO4. These oxidation products were separated as fractions I-III by silica column chromatography using gradient solvent systems. Further, LC-MS/MS (ESI)(+) was used to elucidate their possible fragmentation patterns and structures. Fraction II showed higher cytotoxicity (IC50 value of 64.5 mu M), cellular uptake, and apoptosis-inducing activity in MCF-7 cells. This fraction consists of major peak m/z 323, identified as apo-8,6'-carotendial. The cytotoxicity-inducing activity may be due to partial ROS generation with mitochondrial dysfunction. Further, the role of apo-8,6'-carotendial in the induction of apoptosis is demonstrated for the first time. These results illustrated that LYC-oxidation derivatives or metabolites are involved in growth inhibition of cancer cells. Exploration of specific oxidized-carotenoid products will give further insight into the field of nutritional biochemistry.
• CAROTENOID OXIDATION PRODUCTS AS CHEMOPREVENTIVE AND CHEMOTHERAPEUTIC AGENTS
  申请人：Sharoni Yoav

  公开号：US20090069417A1

  公开（公告）日：2009-03-12

  The present invention relates to a method for the chemoprevention and treatment of cancer, by administering a pharmaceutical composition comprising a carotenoid derivative, such as a derivative of lycopene, a- and b-carotene, phytoene, phytofluene, lutein, zeaxanthin, α- and β-cryptoxanthin, canthaxanthin, astaxanthin, or other carotenoid. The carotenoid derivative is a carotenoid oxidation product, and is preferably an aldehyde derivative, a dialdehyde derivative or a ketone derivative. The carotenoid derivative can be a derivative of any naturally occurring carotenoid, such as those found in tomatoes and other fruits and vegetables.
• [EN] CAROTENOID OXIDATION PRODUCTS AS CHEMOPREVENTIVE AND CHEMOTHERAPEUTIC AGENTS<br/>[FR] PRODUITS D'OXYDATION DES CAROTENOIDES UTILISES EN TANT QU'AGENTS CHIMIOPREVENTIFS ET CHIMIOTHERAPEUTIQUES
  申请人：LYCORED LTD

  公开号：WO2007043046A2

  公开（公告）日：2007-04-19

  [EN] The present invention relates to a method for the chemoprevention and treatment of cancer, by administering a pharmaceutical composition comprising a carotenoid derivative, e.g., a derivative of lycopene, a- and b-carotene, phytoene, phytofluene, lutein, zeaxanthin, a- and b-cryptoxanthin, canthaxanthin, astaxanthin, or other carotenoid. The carotenoid derivative is a carotenoid oxidation product, and is preferably an aldehyde derivative, a dialdehyde derivative or a ketone derivative. The carotenoid derivative can be a derivative of any naturally occurring carotenoid, e.g., carotenoids found in tomatoes and other fruits and vegetables.
  [FR] La présente invention concerne un procédé pour la chimioprévention et le traitement du cancer, par administration d'une composition pharmaceutique comprenant un dérivé de caroténoïde, par ex., un dérivé de lycopène, d'a- et ß-carotène, de phytoène, de phytofluène, de lutéine, de zéaxanthine, d'a- et ß-cryptoxanthine, de canthaxanthine, d'astaxanthine, ou d'autre caroténoïde. Le dérivé de caroténoïde est un produit d'oxydation des caroténoïdes et est de préférence un dérivé d'aldéhyde, un dérivé de dialdéhyde ou un dérivé de cétone. Le dérivé de caroténoïde peut être un dérivé de n'importe quel caroténoïde d'origine naturelle, par ex., des caroténoïdes trouvés dans les tomates et d'autres fruits et légumes.
• Cleavage Products of Lycopene Produced by in Vitro Oxidations:  Characterization and Mechanisms of Formation
  作者：Catherine Caris-Veyrat、Antje Schmid、Michel Carail、Volker Böhm

  DOI：10.1021/jf034735+

  日期：2003.12.1

  The aim of this study was to produce in vitro oxidation products of lycopene, which could be possible in vivo metabolites. An oxidation of lycopene with potassium permanganate gave a range of lycopene degradation compounds resulting from the oxidative cleavage of one or two carbon-carbon double bonds. Eleven apo-lycopenals/ones and six apo-carotendials were obtained and tentatively characterized by

  这项研究的目的是生产番茄红素的体外氧化产物，这可能是体内代谢产物。番茄红素用高锰酸钾的氧化产生了一系列番茄红素降解化合物，这些化合物是由一个或两个碳-碳双键的氧化裂解产生的。获得了十一种载脂蛋白低碳脂蛋白/单糖和六种载脂蛋白-胡萝卜素，并通过HPLC-DAD-MS进行了初步鉴定。首次分离了载脂蛋白-11-冰醛和载脂蛋白8,6'-胡萝卜素，并通过（1）H NMR进行了表征。番茄红素受到金属卟啉催化的大气氧氧化，该金属卟啉是细胞色素P450酶活性中心的模型系统。形成（E）-番茄红素的（Z）-异构体，一氧化物和裂解化合物。我们提出了该系统氧化番茄红素的机理。