(9Z)-violaxanthin | 26927-07-1

• 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: (9Z)-violaxanthin
• 英文别名: 9-cis-violaxanthin；(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15Z,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS: 26927-07-1
• 化学式: C₄₀H₅₆O₄
• 分子量: 600.882
• InChiKey: SZCBXWMUOPQSOX-NLNQYMAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9Z)-violaxanthin 、 乙酸酐 在 吡啶 作用下， 反应 1.0h， 生成 Acetic acid (1R,3S,6S)-6-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-18-((1S,4S,6R)-4-acetoxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]hept-3-yl ester
  参考文献：
  名称：

  来自Pittosporum tobira种子的具有3-甲氧基-5-酮-5,6-seco-4,6-环-β端基的三个新类胡萝卜素的结构。

  摘要：

  从Pittosporum tobira的种子中分离出三个具有3-甲氧基-5-酮-5,6-seco-4,6-环-β端基（1-3）的新类胡萝卜素。通过对核磁共振和紫外线数据的详细分析，阐明了它们的结构。

  DOI：

  10.1248/cpb.49.985
• 作为产物：
  描述：

  紫黄素 生成 (9Z)-violaxanthin
  参考文献：
  名称：

  Impact of the Stage of Ripening and Dietary Fat on in Vitro Bioaccessibility of β-Carotene in ‘Ataulfo’ Mango

  摘要：

  Pulp from "slightly ripe", "moderately ripe", or "fully ripe" mangoes was digested in vitro in the absence and presence of processed chicken as a source of exogenous fat and protein to examine the impact of stage of ripening of mango on micellarization during digestion and intestinal cell uptake (i.e., bioaccessibility) of beta-carotene. The quantity of beta-carotene transferred to the micelle fraction during simulated digestion significantly increased as the fruit ripened and when chicken was mixed with mango before digestion. Qualitative and quantitative changes that occur in pectin from mango pulp during the ripening process influenced the efficiency of micellarization of beta-carotene. Finally, the uptake of P-carotene in micelles generated during simulated digestion by Caco-2 human intestinal cells confirmed the bioaccessibility of the provitamin A carotenoid in mango.

  DOI：

  10.1021/jf072751r

文献信息

• Inhibitors of a 9-cis epoxycarotenoid dioxygenase
  申请人：Abrams Suzanne R.

  公开号：US20100160166A1

  公开（公告）日：2010-06-24

  A compound of formula (I): wherein: R 1 is —SR 10 , —O—C(O)—R 11 , —NR 12 R 13 , where R 10 is a C 1-8 -alkyl group or a phenyl group unsubstituted or substituted by a C 1-4 -alkyl group, R 11 is a thiophenenyl, furanyl or pyrrolyl group, R 12 is H or a C 1-4 -alkyl group and R 13 is a C 1-8 -alkyl group or a phenyl group unsubstituted or substituted by a C 1-4 -alkyl group; R 2 is H or a C 1-4 -alkyl group; R 3 and R 4 are independently H or C 1-4 -alkyl groups; R 5 and R 6 are independently H, OH or OR 14 , or taken together are ═O, where R 14 is a protecting group; R 7 is H or a C 1-4 -alkyl group; and, R 8 is H, R 9 is OH and R 15 is H, or R 15 is H and R 8 and R 9 taken together are —O—, or R 9 is OH and R 8 and R 15 taken together form a bond; and, R 18 and R 19 are both H, or R 18 and R 19 taken together form a bond, or a plant physiologically acceptable salt thereof is useful for inhibiting 9-cis-epoxycarotenoid dioxygenase (NCED) in a plant or seed and is therefore useful for regulating ABA biosynthesis in the plant or seed.

  公式（I）的化合物：其中：R1为—SR10，—O—C（O）—R11，—NR12R13，其中R10为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R11为噻吩基、呋喃基或吡咯基；R12为H或C1-4-烷基，R13为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R2为H或C1-4-烷基；R3和R4分别为H或C1-4-烷基；R5和R6分别为H、OH或OR14，或者一起为═O，其中R14为保护基；R7为H或C1-4-烷基；R8为H，R9为OH，R15为H，或者R15为H，R8和R9一起为—O—，或者R9为OH，R8和R15一起形成键；R18和R19均为H，或者R18和R19一起形成键，或其植物生理学上可接受的盐对于抑制植物或种子中的9-顺式-环氧类胡萝卜二氧化酶（NCED）是有用的，因此对于调节植物或种子中的ABA生物合成是有用的。
• Production of Auroxanthins from Violaxanthin and 9-<i>cis</i>-Violaxanthin by Acidic Treatment and the Antioxidant Activities of Violaxanthin, 9-<i>cis</i>-Violaxanthin, and Auroxanthins
  作者：Michiko Araki、Naoko Kaku、Momoko Harada、Yuka Ando、Risa Yamaguchi、Kazutoshi Shindo

  DOI：10.1021/acs.jafc.6b04506

  日期：2016.12.14

  only violaxanthin but also 9-cis-violaxanthin were found to be converted to (8S,8′S)-, (8S,8′R)-, and (8R,8′R)-auroxanthin at an approximate ratio of 4:6:1. Antioxidant activities of violaxanthin, 9-cis-violaxanthin, (8S,8′S)-auroxanthin, and (8S,8′R)-auroxanthin were examined. They possessed potent lipid peroxidation inhibitory and very weak 1O2 quenching activities.

  从芒果果实中制备紫精质和9-顺式紫精质（水果中的主要环氧类胡萝卜素），进行纯化，然后在酸性条件下转化为其他类胡萝卜素。然后详细分析所得的类胡萝卜素结构。不仅紫黄质，而且9-顺堇菜发现转化为（8小号，8'小号） - ，（8小号，8' - [R ）-和（8 - [R，8' - [R ）以近似-auroxanthin比例为4：6：1。紫黄质的抗氧化活性，9-顺式堇菜，（8小号，8'小号）-auroxanthin，和（8小号，8' - [R检查了-红蛋白。它们具有有效的脂质过氧化抑制作用和非常弱的1 O 2淬灭活性。
• Naturally occurring di-cis-violaxanthins from viola tricolor: Isolation and identification by 1H NMR spectroscopy of four di-cis-isomers
  作者：Péter Molnár、József Szabolcs、Lajos Radics

  DOI：10.1016/s0031-9422(00)94528-x

  日期：1985.12

  have been isolated in the crystalline state. By two-dimensional 1 H NMR methods, the new pigments are shown to be the 9,9′-, 9,13′-, 9,15- and 9,13-di- cis isomers. Thermal and iodine-catalysed photochemical stereomutations of the new natural pigments have also been studied.

  摘要 从三色堇的花朵中，发现了四种新的天然紫黄质几何异构体（5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3' -二醇）已在结晶状态下分离。通过二维 1 H NMR 方法，新颜料显示为 9,9'-、9,13'-、9,15- 和 9,13-二顺式异构体。还研究了新天然色素的热和碘催化光化学立体突变。
• 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。
• Eine Neuuntersuchung der Carotinoide aus<i>Rosa foetida</i>: Struktur von 12 neuen Carotinoiden; stereoisomere Luteoxanthine, Auroxanthine, Latoxanthine und Latochrome
  作者：Edith Märki-Fischer、Richard Buchecker、Conrad Hans Eugster

  DOI：10.1002/hlca.19840670814

  日期：1984.12.19

  Reinvestigation of the Carotenoids from Rosa foetida, structures of 12 Novel Carotenoids; Stereoisomeric Luteoxanthins, Auroxanthins, Latoxanthins and Latochromes

  对来自Rosa foetida的类胡萝卜素进行重新研究，发现12种新型类胡萝卜素的结构；立体异构的黄体黄质，金质黄质，拉托黄质和拉托色素