Violaxanthin (BioDeep_00000402897)

Main id: BioDeep_00000003679

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol

化学式: C40H56O4 (600.4178376)
中文名称: 紫黄质(非对映异构体混合物)
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=CC=CC=C(C)C=CC=C(C)C=CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=CC34C(CC(CC3(O4)C)O)(C)C
InChI: InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-40-37(7,8)26-33(43-40)27-39(40,10)42)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)25-38(35,9)44-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+

描述信息

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
Cucurbitachrome 1 is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Cucurbitachrome 1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitachrome 1 can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and red bell pepper, which makes cucurbitachrome 1 a potential biomarker for the consumption of these food products.
(all-e)-violaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as orange bell pepper, green bell pepper, passion fruit, and yellow bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.

同义名列表

17 个代谢物同义名

Violaxanthin; 3,6:5,8-Diepoxy-5,5,6,8-tetrahydro-b,b-carotene-3,5-diol; (1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol; (1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,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]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol; (1S,4S,6R)-1-[18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol; (1S,4S,6R)-1-[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]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol; (3S,3S,5R,5R, 6S,6S)-5,6:5,6-Diepoxy-5,5,6,6-tetrahydro-beta,beta-carotene-3,3-diol; (3S,5R,6S,3S,5R,6S)-5,6,5,6-DIEPOXY-5,6,5,6- TETRAHYDRO-BETA,BETA-CAROTENE-3,3-DIOL; 5,6:5,6-Diepoxy-5,5,6,6-tetrahydro-beta-carotene-3,3-diol; all-trans-Violaxanthin; Zeaxanthin diepoxide; LMPR01070282; 126-29-4; C08614; XAT; (Z)-Violaxanthin 1; (Z)-Violaxanthin 2



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(6)

PlantCyc(4)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

192 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Jia Wang, Xiao Zhou, Kexin Li, Herong Wang, Chenglong Zhang, Yi Shi, Mingdong Yao, Ying Wang, Wenhai Xiao. Systems Metabolic Engineering for Efficient Violaxanthin Production in Yeast. Journal of agricultural and food chemistry. 2024 May; 72(18):10459-10468. doi: 10.1021/acs.jafc.4c01240. [PMID: 38666490]
  • Zoltán Tolnai, Himani Sharma, Vilmos Soós. D27-like carotenoid isomerases: at the crossroads of strigolactone and abscisic acid biosynthesis. Journal of experimental botany. 2024 Feb; 75(4):1148-1158. doi: 10.1093/jxb/erad475. [PMID: 38006582]
  • Sushil S Changan, Vaibhav Kumar, Aruna Tyagi. Expression pattern of candidate genes and their correlation with various metabolites of abscisic acid biosynthetic pathway under drought stress in rice. Physiologia plantarum. 2023 Nov; 175(6):e14102. doi: 10.1111/ppl.14102. [PMID: 38148246]
  • Dong Xinrui, Liu Bo, Bao Yihong, Liu Weifeng, Tao Yong. Metabolic engineering of Escherichia coli for high-level production of violaxanthin. Microbial cell factories. 2023 Jun; 22(1):115. doi: 10.1186/s12934-023-02098-y. [PMID: 37344799]
  • Giorgio Perin, Alessandra Bellan, Tim Michelberger, Dagmar Lyska, Setsuko Wakao, Krishna K Niyogi, Tomas Morosinotto. Modulation of xanthophyll cycle impacts biomass productivity in the marine microalga Nannochloropsis. Proceedings of the National Academy of Sciences of the United States of America. 2023 Jun; 120(25):e2214119120. doi: 10.1073/pnas.2214119120. [PMID: 37307488]
  • Uthman O Badmus, Gaia Crestani, Natalie Cunningham, Michel Havaux, Otmar Urban, Marcel A K Jansen. UV Radiation Induces Specific Changes in the Carotenoid Profile of Arabidopsis thaliana. Biomolecules. 2022 12; 12(12):. doi: 10.3390/biom12121879. [PMID: 36551307]
  • Zsolt Gulyás, Blanka Moncsek, Kamirán Áron Hamow, Pál Stráner, Zoltán Tolnai, Eszter Badics, Norbert Incze, Éva Darkó, Valéria Nagy, András Perczel, László Kovács, Vilmos Soós. D27-LIKE1 isomerase has a preference towards trans/cis and cis/cis conversions of carotenoids in Arabidopsis. The Plant journal : for cell and molecular biology. 2022 12; 112(6):1377-1395. doi: 10.1111/tpj.16017. [PMID: 36308414]
  • Donatella Carbonera, Alessandro Agostini, Marco Bortolus, Luca Dall'Osto, Roberto Bassi. Violaxanthin and Zeaxanthin May Replace Lutein at the L1 Site of LHCII, Conserving the Interactions with Surrounding Chlorophylls and the Capability of Triplet-Triplet Energy Transfer. International journal of molecular sciences. 2022 Apr; 23(9):. doi: 10.3390/ijms23094812. [PMID: 35563202]
  • Maria Dolores Garcia Molina, Ermelinda Botticella, Romina Beleggia, Samuela Palombieri, Pasquale De Vita, Stefania Masci, Domenico Lafiandra, Francesco Sestili. Enrichment of provitamin A content in durum wheat grain by suppressing β-carotene hydroxylase 1 genes with a TILLING approach. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2021 Dec; 134(12):4013-4024. doi: 10.1007/s00122-021-03944-6. [PMID: 34477900]
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  • Minjung Son, Raymundo Moya, Alberta Pinnola, Roberto Bassi, Gabriela S Schlau-Cohen. Protein-Protein Interactions Induce pH-Dependent and Zeaxanthin-Independent Photoprotection in the Plant Light-Harvesting Complex, LHCII. Journal of the American Chemical Society. 2021 10; 143(42):17577-17586. doi: 10.1021/jacs.1c07385. [PMID: 34648708]
  • Ewa Surówka, Dariusz Latowski, Michał Dziurka, Magdalena Rys, Anna Maksymowicz, Iwona Żur, Monika Olchawa-Pajor, Christine Desel, Monika Krzewska, Zbigniew Miszalski. ROS-Scavengers, Osmoprotectants and Violaxanthin De-Epoxidation in Salt-Stressed Arabidopsis thaliana with Different Tocopherol Composition. International journal of molecular sciences. 2021 Oct; 22(21):. doi: 10.3390/ijms222111370. [PMID: 34768798]
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  • Ocsana Opriş, Florina Copaciu, Maria Loredana Soran, Ülo Niinemets, Lucian Copolovici. Content of Carotenoids, Violaxanthin and Neoxanthin in Leaves of Triticum aestivum Exposed to Persistent Environmental Pollutants. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154448. [PMID: 34361600]
  • Wei Huang, Hong Hu, Shi-Bao Zhang. Photosynthetic regulation under fluctuating light at chilling temperature in evergreen and deciduous tree species. Journal of photochemistry and photobiology. B, Biology. 2021 Jun; 219(?):112203. doi: 10.1016/j.jphotobiol.2021.112203. [PMID: 33957467]
  • Gang Ma, Lancui Zhang, Yurika Kitaya, Mao Seoka, Rin Kudaka, Masaki Yahata, Kazuki Yamawaki, Takehiko Shimada, Hiroshi Fujii, Tomoko Endo, Masaya Kato. Blue LED light induces regreening in the flavedo of Valencia orange in vitro. Food chemistry. 2021 Jan; 335(?):127621. doi: 10.1016/j.foodchem.2020.127621. [PMID: 32738533]
  • Geniane Schneider, Félix L Figueroa, Julia Vega, Antonio Avilés, Patricia Chaves, Paulo Antunes Horta, Nathalie Korbee, José Bonomi-Barufi. Physiological and biochemical responses driven by different UV-visible radiation in Osmundea pinnatifida (Hudson) Stackhouse (Rhodophyta). Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2020 Dec; 19(12):1650-1664. doi: 10.1039/d0pp00135j. [PMID: 33030484]
  • Yingjun Liu, Shenhua Ye, Gaigai Yuan, Xiaowei Ma, Shuangping Heng, Bin Yi, Chaozhi Ma, Jinxiong Shen, Jinxing Tu, Tingdong Fu, Jing Wen. Gene silencing of BnaA09.ZEP and BnaC09.ZEP confers orange color in Brassica napus flowers. The Plant journal : for cell and molecular biology. 2020 11; 104(4):932-949. doi: 10.1111/tpj.14970. [PMID: 32808386]
  • Margherita Lapillo, Edoardo Cignoni, Lorenzo Cupellini, Benedetta Mennucci. The energy transfer model of nonphotochemical quenching: Lessons from the minor CP29 antenna complex of plants. Biochimica et biophysica acta. Bioenergetics. 2020 11; 1861(11):148282. doi: 10.1016/j.bbabio.2020.148282. [PMID: 32721398]
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  • Ondřej Dlouhý, Irena Kurasová, Václav Karlický, Uroš Javornik, Primož Šket, Nia Z Petrova, Sashka B Krumova, Janez Plavec, Bettina Ughy, Vladimír Špunda, Győző Garab. Modulation of non-bilayer lipid phases and the structure and functions of thylakoid membranes: effects on the water-soluble enzyme violaxanthin de-epoxidase. Scientific reports. 2020 07; 10(1):11959. doi: 10.1038/s41598-020-68854-x. [PMID: 32686730]
  • Vicente F Cataldo, Natalia Arenas, Valeria Salgado, Conrado Camilo, Francisco Ibáñez, Eduardo Agosin. Heterologous production of the epoxycarotenoid violaxanthin in Saccharomyces cerevisiae. Metabolic engineering. 2020 05; 59(?):53-63. doi: 10.1016/j.ymben.2020.01.006. [PMID: 32001334]
  • O Dautermann, D Lyska, J Andersen-Ranberg, M Becker, J Fröhlich-Nowoisky, H Gartmann, L C Krämer, K Mayr, D Pieper, L M Rij, H M-L Wipf, K K Niyogi, M Lohr. An algal enzyme required for biosynthesis of the most abundant marine carotenoids. Science advances. 2020 03; 6(10):eaaw9183. doi: 10.1126/sciadv.aaw9183. [PMID: 32181334]
  • Jiangtao Zhou, Sergey Sekatskii, Renata Welc, Giovanni Dietler, Wieslaw I Gruszecki. The role of xanthophylls in the supramolecular organization of the photosynthetic complex LHCII in lipid membranes studied by high-resolution imaging and nanospectroscopy. Biochimica et biophysica acta. Bioenergetics. 2020 02; 1861(2):148117. doi: 10.1016/j.bbabio.2019.148117. [PMID: 31734197]
  • Miho Takemura, Akiko Kubo, Yuki Higuchi, Takashi Maoka, Takehiko Sahara, Katsuro Yaoi, Kohji Ohdan, Daisuke Umeno, Norihiko Misawa. Pathway engineering for efficient biosynthesis of violaxanthin in Escherichia coli. Applied microbiology and biotechnology. 2019 Dec; 103(23-24):9393-9399. doi: 10.1007/s00253-019-10182-w. [PMID: 31673744]
  • Monika Olchawa-Pajor, Monika Bojko, Wojciech Strzałka, Kazimierz Strzałka, Dariusz Latowski. Violaxanthin conversion by recombinant diatom and plant de-epoxidases, expressed in Escherichia coli - comparative analysis. Acta biochimica Polonica. 2019 Jul; 66(3):249-255. doi: 10.18388/abp.2019_2831. [PMID: 31279328]
  • Grzegorz Fiutak, Magdalena Michalczyk, Magda Filipczak-Fiutak, Leszek Fiedor, Krzysztof Surówka. The impact of LED lighting on the yield, morphological structure and some bioactive components in alfalfa (Medicago sativa L.) sprouts. Food chemistry. 2019 Jul; 285(?):53-58. doi: 10.1016/j.foodchem.2019.01.086. [PMID: 30797375]
  • Yanyan Su. The effect of different light regimes on pigments in Coscinodiscus granii. Photosynthesis research. 2019 Jun; 140(3):301-310. doi: 10.1007/s11120-018-0608-7. [PMID: 30478709]
  • Marijonas Tutkus, Francesco Saccon, Jevgenij Chmeliov, Oskaras Venckus, Ignas Ciplys, Alexander V Ruban, Leonas Valkunas. Single-molecule microscopy studies of LHCII enriched in Vio or Zea. Biochimica et biophysica acta. Bioenergetics. 2019 06; 1860(6):499-507. doi: 10.1016/j.bbabio.2019.05.002. [PMID: 31055058]
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  • Raquel Esteban, Javier Buezo, José M Becerril, José I García-Plazaola. Modified Atmosphere Packaging and Dark/Light Refrigerated Storage in Green Leafy Vegetables Have an Impact on Nutritional Value. Plant foods for human nutrition (Dordrecht, Netherlands). 2019 Mar; 74(1):99-106. doi: 10.1007/s11130-018-0705-y. [PMID: 30610553]
  • David Bína, Milan Durchan, Valentyna Kuznetsova, František Vácha, Radek Litvín, Tomáš Polívka. Energy transfer dynamics in a red-shifted violaxanthin-chlorophyll a light-harvesting complex. Biochimica et biophysica acta. Bioenergetics. 2019 02; 1860(2):111-120. doi: 10.1016/j.bbabio.2018.11.006. [PMID: 30414929]
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  • Matthias Karadar, Gilbert Neuner, Ilse Kranner, Andreas Holzinger, Othmar Buchner. Solar irradiation levels during simulated long- and short-term heat waves significantly influence heat survival, pigment and ascorbate composition, and free radical scavenging activity in alpine Vaccinium gaultherioides. Physiologia plantarum. 2018 Jun; 163(2):211-230. doi: 10.1111/ppl.12686. [PMID: 29274132]
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  • Lars Nichelmann, Wolfgang Bilger. Quantification of light screening by anthocyanins in leaves of Berberis thunbergii. Planta. 2017 Dec; 246(6):1069-1082. doi: 10.1007/s00425-017-2752-2. [PMID: 28801823]
  • Manuel J Llansola-Portoles, Radek Litvin, Cristian Ilioaia, Andrew A Pascal, David Bina, Bruno Robert. Pigment structure in the violaxanthin-chlorophyll-a-binding protein VCP. Photosynthesis research. 2017 Oct; 134(1):51-58. doi: 10.1007/s11120-017-0407-6. [PMID: 28677008]
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