Violaxanthin (BioDeep_00000003679)

 

Secondary id: BioDeep_00000228949, BioDeep_00000402897

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(1R,3S,6S)-6-[(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-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

化学式: C40H56O4 (600.4178)
中文名称: 紫黄质(非对映异构体混合物), 紫黄素
谱图信息: 最多检出来源 Homo sapiens(feces) 24.87%

分子结构信息

SMILES: CC(/C=C/C=C(C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C
InChI: InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

描述信息

Violaxanthin belongs to the class of organic compounds known as xanthophylls. These 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662).
3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as violaxanthin cycle; Xanthophyll; a carotene epoxide that is precursor to capsanthin; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution). (all-E)-Violaxanthin is found in many foods, some of which are orange bell pepper, passion fruit, pepper (c. annuum), and italian sweet red pepper.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

19 个代谢物同义名

(1R,3S,6S)-6-[(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-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol; (3S,3’S,5R,5’r,6S,6’s)-5,6:5’,6’-diepoxy-5,5’,6,6’-tetrahydro-β,β-carotene-3,3’-diol; (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; (3S,5R,6S,3s,5r,6s)-5,6,5,6-DIEPOXY-5,6,5,6-tetrahydro-β,β-carotene-3,3-diol; (3S,5R,6S,3s,5r,6s)-5,6,5,6-DIEPOXY-5,6,5,6-tetrahydro-b,b-carotene-3,3-diol; (3S,3s,5R,5r,6S,6s)-5,6:5,6-Diepoxy-5,5,6,6-tetrahydro-b,b-carotene-3,3-diol; (3S,3s,5R,5r,6S,6s)-5,6:5,6-Diepoxy-5,5,6,6-tetrahydro-β,β-carotene-3,3-diol; 5,6:5′,6′-diepoxy-5,5′,6,6′-tetrahydro-beta-carotene-3,3′-diol; 5,6:5′,6′-diepoxy-5,5′,6,6′-tetrahydro-β-carotene-3,3′-diol; 5,6:5,6-Diepoxy-5,5,6,6- tetrahydro-beta-carotene-3,3-diol; all-trans-Violaxanthin; Zeaxanthin diepoxide; (all-E)-Violaxanthin; trans-Violaxanthin; all-e-Violaxanthin; Violaxanthin; e 161E; Violaxanthin



数据库引用编号

21 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

728 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(8)

WikiPathways(0)

Plant Reactome(234)

INOH(0)

PlantCyc(486)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

652 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 BFSP2, CAT, DNAL1, GGPS1, SPX, TYR, TYRP1, VCP
Peripheral membrane protein 3 BFSP2, CYP1B1, PLOD2
Endosome membrane 1 TYRP1
Endoplasmic reticulum membrane 4 CYP1B1, CYP26A1, PLOD2, VCP
Nucleus 2 MYB, VCP
cytosol 6 CAT, GGPS1, GSR, LIPE, MYB, VCP
nucleoplasm 3 GGPS1, MYB, VCP
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 2 BFSP2, LIPE
Cytoplasmic side 1 BFSP2
cell cortex 1 BFSP2
glutamatergic synapse 1 VCP
lysosomal membrane 1 GAA
mitochondrial inner membrane 2 ATP5ME, CYP24A1
Cytoplasm, cytosol 2 LIPE, VCP
Cytoplasmic vesicle, secretory vesicle 1 SPX
Lysosome 2 GAA, TYR
plasma membrane 2 BFSP2, GAA
Membrane 5 CAT, CYP1B1, GAA, LIPE, MYB
caveola 1 LIPE
extracellular exosome 6 CAT, DEFA3, GAA, GSR, PLOD2, VCP
Lysosome membrane 1 GAA
Lumenal side 1 PLOD2
endoplasmic reticulum 2 PLOD2, VCP
extracellular space 3 DEFA3, PNLIP, SPX
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 GGPS1, TYR, VCP
mitochondrion 5 ATP5ME, CAT, CYP1B1, CYP24A1, GSR
protein-containing complex 2 CAT, VCP
intracellular membrane-bounded organelle 5 CAT, CYP1B1, GAA, TYR, VCP
Microsome membrane 2 CYP1B1, CYP26A1
Single-pass type I membrane protein 2 TYR, TYRP1
Secreted 3 DEFA3, GAA, PNLIP
extracellular region 6 CAT, DEFA3, GAA, PNLIP, SPX, VCP
mitochondrial matrix 2 CAT, GSR
external side of plasma membrane 1 GSR
Z disc 1 GGPS1
Melanosome membrane 2 TYR, TYRP1
Golgi-associated vesicle 1 TYR
Cytoplasm, perinuclear region 1 GGPS1
Cytoplasm, cytoskeleton 1 BFSP2
focal adhesion 1 CAT
microtubule 1 DNAL1
Peroxisome 1 CAT
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
intermediate filament 1 BFSP2
cytoskeleton 1 BFSP2
Secreted, extracellular space 1 SPX
Cytoplasm, cell cortex 1 BFSP2
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAL1
site of double-strand break 1 VCP
Lipid droplet 2 LIPE, VCP
Membrane, caveola 1 LIPE
tertiary granule membrane 1 GAA
Melanosome 2 TYR, TYRP1
Cytoplasm, Stress granule 1 VCP
cytoplasmic stress granule 1 VCP
Cytoplasm, myofibril, sarcomere, Z line 1 GGPS1
ficolin-1-rich granule lumen 2 CAT, VCP
proteasome complex 1 VCP
secretory granule lumen 2 CAT, VCP
Golgi lumen 1 DEFA3
nuclear matrix 1 MYB
dense core granule 1 SPX
transport vesicle 1 SPX
azurophil granule membrane 1 GAA
rough endoplasmic reticulum membrane 1 PLOD2
azurophil granule lumen 2 DEFA3, VCP
clathrin-coated endocytic vesicle membrane 1 TYRP1
ficolin-1-rich granule membrane 1 GAA
Rough endoplasmic reticulum 1 PLOD2
ATPase complex 1 VCP
proton-transporting ATP synthase complex 1 ATP5ME
VCP-NPL4-UFD1 AAA ATPase complex 1 VCP
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
catalase complex 1 CAT
autolysosome lumen 1 GAA
Derlin-1 retrotranslocation complex 1 VCP
VCP-NSFL1C complex 1 VCP
outer dynein arm 1 DNAL1


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]
  • Petra Skotnicová, Hristina Staleva-Musto, Valentyna Kuznetsova, David Bína, Minna M Konert, Shan Lu, Tomáš Polívka, Roman Sobotka. Plant LHC-like proteins show robust folding and static non-photochemical quenching. Nature communications. 2021 11; 12(1):6890. doi: 10.1038/s41467-021-27155-1. [PMID: 34824207]
  • 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]
  • Reimund Goss, Christian Schwarz, Monique Matzner, Christian Wilhelm. Influence of the compatible solute sucrose on thylakoid membrane organization and violaxanthin de-epoxidation. Planta. 2021 Aug; 254(3):52. doi: 10.1007/s00425-021-03699-w. [PMID: 34392410]
  • 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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  • 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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