apo-14'-lycopenal | 339561-77-2

• 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-14'-lycopenal
• 英文别名: (2E,4E,6E,8E,10E,12E,16E)-5,9,13,17-tetramethyloctadeca-2,4,6,8,10,12,16-heptaenal；(2E,4E,6E,8E,10E,12E)-5,9,13,17-tetramethyloctadeca-2,4,6,8,10,12,16-heptaenal
• CAS: 339561-77-2
• 化学式: C₂₂H₃₀O
• 分子量: 310.48
• InChiKey: GIKHYDJRGRLGLM-UBSLRWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2E,4E,6E,8E,10E,12E,16E)-5,9,13,17-tetramethyloctadeca-2,4,6,8,10,12,16-heptaen-1-ol 在 manganese(IV) oxide 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以44%的产率得到apo-14'-lycopenal
  参考文献：
  名称：

  Antioxidant activity of (all-E)-lycopene and synthetic apo-lycopenoids in a chemical model of oxidative stress in the gastro-intestinal tract

  摘要：

  众所周知，番茄的主要色素番茄红素具有保护健康的作用。番茄红素的代谢物也可能参与了这些作用。利用 HWE 缩合反应，通过有机合成获得了具有潜在生物活性的番茄红素代谢物，即具有醇、羧酸、醛和乙酯末端基团的 (all-E) 立体异构体 (apo-10′-lycopenol、apo-10′-lycopenal、apo-14′-lycopenol、apo-14′-lycopenal 和 apo-11-lycopenoids)。在胃区餐后氧化应激的化学模型中，测试了（全-E）-甘油三酯和合成的apo-lycopenoids抑制脂质过氧化的能力。氧化应激是由高铁血红蛋白产生的，高铁血红蛋白是食物中铁的主要形式（来自红肉），它能在弱酸性条件下催化亚油酸的过氧化反应。在该模型中，apo-6′-lycopenal 和 apo-8′-lycopenal 比 (all-E)-lycopene 本身更能抑制脂质过氧化。对于apo-lycopenoids来说，长的不饱和链和末端的羧酸基团都有利于其抗氧化活性。事实证明，短链的apo-lycopenoic acid（apo-14′-lycopenoic acid）具有亲水性抗氧化剂的作用，即减少高铁血红蛋白的高价铁形式。因此，除了多烯链的长度外，环甘氨酸的末端基团预计也会对分子的亲油/亲水平衡（从而影响其在水相和脂相之间的分布）及其对血红素腔的亲和力产生深远影响。因此可以得出结论，多烯链长度和末端基团是调节脂环素抗氧化活性机制的两个重要参数。

  DOI：

  10.1039/c1nj20437h

文献信息

• Identification and Quantification of Apo-lycopenals in Fruits, Vegetables, and Human Plasma
  作者：Rachel E. Kopec、Ken M. Riedl、Earl H. Harrison、Robert W. Curley、Damian P. Hruszkewycz、Steven K. Clinton、Steven J. Schwartz

  DOI：10.1021/jf100415z

  日期：2010.3.24

  Research has suggested that lycopene may be metabolized by eccentric cleavage, catalyzed by beta-carotene oxygenase 2, resulting in the generation of apo-lycopenals. Apo-6'-lycopenal and apo-8'-lycopenal have been reported previously in raw tomato. We now show that several other apo-lycopenals are also present in raw and processed foods, as well as in human plasma. Apo-lycopenal standards were prepared by in vitro oxidation of lycopene, and a high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method using atmospheric pressure chemical ionization in negative mode was developed to separate and detect the apo-6'-, apo-8-, apo-10'-, apo-12'-, apo-14'-, and apo-15'-lycopenal products formed in the reaction. Hexane/acetone extracts of raw tomato, red grapefruit, watermelon, and processed tomato products were analyzed, as well as plasma of individuals who had consumed tomato juice for 8 weeks. Apo-6'-, apo-8'-, apo-10'-, apo-12'-, and apo-14'-lycopenals were detected and quantified in all food products tested, as well as plasma. The sum of apo-lycopenals was 6.5 mu g/100 g Roma tomato, 73.4 mu g/100 g tomato paste, and 1.9 nmol/L plasma. We conclude that several apo-lycopenals, in addition to apo-6'- and -8'-lycopenal, are present in lycopene-containing foods. In addition, the presence of apo-lycopenals in plasma may derive from the absorption of apo-lycopenals directly from food and/or human metabolism.
• 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.
• Antioxidant activity of (all-E)-lycopene and synthetic apo-lycopenoids in a chemical model of oxidative stress in the gastro-intestinal tract
  作者：Pascale Goupy、Eric Reynaud、Olivier Dangles、Catherine Caris-Veyrat

  DOI：10.1039/c1nj20437h

  日期：——

  Lycopene, the main pigment of tomato, is known to have protective effects on health. Its metabolites could also be involved in these effects. Potentially bioactive lycopene metabolites namely apo-10′-lycopenol, apo-10′-lycopenal, apo-14′-lycopenol, apo-14′-lycopenal, and apo-11-lycopenoids with alcohol, carboxylic acid, aldehyde and ethyl ester terminal groups were obtained by organic synthesis as (all-E) stereoisomers using HWE condensation reactions. The ability of (all-E)-lycopene and the synthesized apo-lycopenoids to inhibit lipid peroxidation was tested in a chemical model of postprandial oxidative stress in the gastric compartment. Oxidative stress was generated by metmyoglobin, the main form of dietary iron (from red meat), which is able to catalyse the peroxidation of linoleic acid under mildly acidic conditions. In this model, apo-6′-lycopenal and apo-8′-lycopenal were better inhibitors of lipid peroxidation than (all-E)-lycopene itself. For the apo-lycopenoids, a long unsaturated chain and a terminal carboxylic acid group both favour the antioxidant activity. The short-chain apo-lycopenoic acid, apo-14′-lycopenoic acid, was shown to behave like a hydrophilic antioxidant, i.e. by reducing hypervalent iron forms of metmyoglobin. Thus, besides the polyene chain length, the terminal group of the apo-lycopenoids is expected to deeply influence the lipophilic/hydrophilic balance of the molecule (and consequently its distribution between the aqueous and lipid phases) and its affinity for the heme cavity. It can thus be concluded that the polyene chain length and terminal group are two important parameters modulating the mechanism by which apo-lycopenoids express their antioxidant activity.

  众所周知，番茄的主要色素番茄红素具有保护健康的作用。番茄红素的代谢物也可能参与了这些作用。利用 HWE 缩合反应，通过有机合成获得了具有潜在生物活性的番茄红素代谢物，即具有醇、羧酸、醛和乙酯末端基团的 (all-E) 立体异构体 (apo-10′-lycopenol、apo-10′-lycopenal、apo-14′-lycopenol、apo-14′-lycopenal 和 apo-11-lycopenoids)。在胃区餐后氧化应激的化学模型中，测试了（全-E）-甘油三酯和合成的apo-lycopenoids抑制脂质过氧化的能力。氧化应激是由高铁血红蛋白产生的，高铁血红蛋白是食物中铁的主要形式（来自红肉），它能在弱酸性条件下催化亚油酸的过氧化反应。在该模型中，apo-6′-lycopenal 和 apo-8′-lycopenal 比 (all-E)-lycopene 本身更能抑制脂质过氧化。对于apo-lycopenoids来说，长的不饱和链和末端的羧酸基团都有利于其抗氧化活性。事实证明，短链的apo-lycopenoic acid（apo-14′-lycopenoic acid）具有亲水性抗氧化剂的作用，即减少高铁血红蛋白的高价铁形式。因此，除了多烯链的长度外，环甘氨酸的末端基团预计也会对分子的亲油/亲水平衡（从而影响其在水相和脂相之间的分布）及其对血红素腔的亲和力产生深远影响。因此可以得出结论，多烯链长度和末端基团是调节脂环素抗氧化活性机制的两个重要参数。