Norbixin (BioDeep_00000006881)

 

Secondary id: BioDeep_00000638834

human metabolite Endogenous natural product


代谢物信息卡片


4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid

化学式: C24H28O4 (380.1987)
中文名称: 降红木素
谱图信息: 最多检出来源 Viridiplantae(plant) 95.53%

分子结构信息

SMILES: C(=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(/C)\C=C\C(=O)O)/C)\C)\C)/C(=O)O
InChI: InChI=1S/C24H28O4/c1-19(11-7-13-21(3)15-17-23(25)26)9-5-6-10-20(2)12-8-14-22(4)16-18-24(27)28/h5-18H,1-4H3,(H,25,26)(H,27,28)

描述信息

Norbixin is a water-soluble food colour. Commercial forms contain mixtures of isomers and their methyl esters. Norbixin is used to colour butter, margarine and other fat-related products. Upon exposure to alkali, the bixins methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative. Bixin is an apocarotenoid found in annatto, a natural food coloring obtained from the seeds of the achiote tree (Bixa orellana). (Wikipedia
Water-soluble food colour. Commercial forms contain mixts. of isomers and their Me esters. It is used to colour butter, margarine and other fat-related products
D000074385 - Food Ingredients > D005503 - Food Additives > D005505 - Food Coloring Agents
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
D004396 - Coloring Agents

同义名列表

11 个代谢物同义名

4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid; 4,8,13,17-Tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioate; 6,6-Diapo-psi,psi-carotenedioic acid; 6,6-Diapo-6,6-carotenedioic acid; diapocarotene-6,6-dioic acid; e160 (Norbixin); β-Norbixin; Norbixin; Norbixen; Annatto; Norbixin



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(1)

代谢反应

8 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(8)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

21 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 10 ALB, CAT, CYP1A1, CYP2B6, HPGDS, LPO, PPARG, RDH8, TXNRD1, VEGFA
Peripheral membrane protein 2 CYP1A1, CYP2B6
Endoplasmic reticulum membrane 4 CYP1A1, CYP1A2, CYP2B6, PON1
Nucleus 6 ALB, JUND, PPARA, PPARG, TXNRD1, VEGFA
cytosol 8 ALB, CAT, GSR, HPGDS, PPARG, RDH8, RPE, TXNRD1
centrosome 1 ALB
nucleoplasm 5 HPGDS, JUND, PPARA, PPARG, TXNRD1
RNA polymerase II transcription regulator complex 2 JUND, PPARG
Multi-pass membrane protein 2 ABCA4, RDH8
cell surface 1 VEGFA
Golgi apparatus 2 ALB, VEGFA
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP1A1
plasma membrane 2 ABCA4, RDH8
Membrane 4 ABCA4, CAT, RDH8, VEGFA
basolateral plasma membrane 1 LPO
extracellular exosome 7 ALB, CAT, GSR, LPO, PON1, RPE, TXNRD1
endoplasmic reticulum 3 ABCA4, ALB, VEGFA
extracellular space 7 ALB, CCL2, CXCL8, INS, LPO, PON1, VEGFA
perinuclear region of cytoplasm 1 PPARG
adherens junction 1 VEGFA
mitochondrion 4 CAT, CYP1A1, GSR, TXNRD1
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 7 ABCA4, CAT, CYP1A1, CYP1A2, CYP2B6, HPGDS, PPARG
Microsome membrane 3 CYP1A1, CYP1A2, CYP2B6
Secreted 6 ALB, CCL2, CXCL8, INS, LPO, VEGFA
extracellular region 8 ALB, CAT, CCL2, CXCL8, INS, LPO, PON1, VEGFA
mitochondrial matrix 2 CAT, GSR
anchoring junction 1 ALB
transcription regulator complex 1 JUND
photoreceptor outer segment 1 ABCA4
external side of plasma membrane 1 GSR
Secreted, extracellular space, extracellular matrix 1 VEGFA
high-density lipoprotein particle 1 PON1
cytoplasmic vesicle 1 ABCA4
Mitochondrion inner membrane 1 CYP1A1
focal adhesion 1 CAT
extracellular matrix 1 VEGFA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 VEGFA
receptor complex 1 PPARG
ciliary basal body 1 ALB
chromatin 3 JUND, PPARA, PPARG
centriole 1 ALB
Cell projection, cilium, photoreceptor outer segment 1 ABCA4
[Isoform 5]: Cytoplasm 1 TXNRD1
spindle pole 1 ALB
blood microparticle 2 ALB, PON1
fibrillar center 1 TXNRD1
endosome lumen 1 INS
[Isoform 1]: Cytoplasm 1 TXNRD1
[Isoform 4]: Cytoplasm 1 TXNRD1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 ALB, INS
transcription repressor complex 1 JUND
platelet alpha granule lumen 2 ALB, VEGFA
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
spherical high-density lipoprotein particle 1 PON1
photoreceptor disc membrane 1 ABCA4
transcription factor AP-1 complex 1 JUND
catalase complex 1 CAT
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
ciliary transition fiber 1 ALB
rod photoreceptor disc membrane 1 ABCA4


文献列表

  • Sabrina Somacal, Andréia Quatrin, Amanda R Ruviaro, Lisiane Conte, Dariane T da Silva, Miguel Roehrs, Marcelo L da Veiga, Marta M F Duarte, Andreza F de Bem, Paula R Augusti, Tatiana Emanuelli. Norbixin, a natural dye that improves serum lipid profile in rabbits and prevents LDL oxidation. Food research international (Ottawa, Ont.). 2022 09; 159(?):111522. doi: 10.1016/j.foodres.2022.111522. [PMID: 35940777]
  • K Courth, M Binsch, W Ali, K Ingenbosch, H Zorn, K Hoffmann-Jacobsen, J S Gutmann, K Opwis. Immobilization of peroxidase on textile carrier materials and their application in the bleaching of colored whey. Journal of dairy science. 2021 Feb; 104(2):1548-1559. doi: 10.3168/jds.2019-17110. [PMID: 33309341]
  • Prateek Sharma, Annalisa Segat, Alan L Kelly, Jeremiah J Sheehan. Colorants in cheese manufacture: Production, chemistry, interactions, and regulation. Comprehensive reviews in food science and food safety. 2020 07; 19(4):1220-1242. doi: 10.1111/1541-4337.12519. [PMID: 33337089]
  • Anissa Algara Beni, Renata Fritzsche Rodrigues, Lisiane Conte, Isabella Ferreira Costa, Érika Aparecida Delalibera, Miguel Roehrs, Cristine Rampelotto, Tatiana Emanuelli, Sabrina Somacal. Dietary supplementation with annatto food-coloring extracts increases the resistance of human erythrocytes to hemolysis. Nutrition research (New York, N.Y.). 2020 04; 76(?):71-81. doi: 10.1016/j.nutres.2020.02.003. [PMID: 32217378]
  • Rohini A, Neeraj Agrawal, Harish Kumar, Virendra Nath, Vipin Kumar. Norbixin, an apocarotenoid derivative activates PPARγ in cardiometabolic syndrome: Validation by in silico and in vivo experimental assessment. Life sciences. 2018 Sep; 209(?):69-77. doi: 10.1016/j.lfs.2018.08.001. [PMID: 30076922]
  • B G Carter, C W Park, M A Drake. Short communication: Sensitive detection of norbixin in dried dairy ingredients at concentrations of less than 1 part per billion. Journal of dairy science. 2017 Nov; 100(11):8754-8758. doi: 10.3168/jds.2017-13095. [PMID: 28843687]
  • Miguel Roehrs, Lisiane Conte, Dariane Trivisiol da Silva, Thiago Duarte, Luana Haselein Maurer, José Antonio Mainardi de Carvalho, Rafael Noal Moresco, Sabrina Somacal, Tatiana Emanuelli. Annatto carotenoids attenuate oxidative stress and inflammatory response after high-calorie meal in healthy subjects. Food research international (Ottawa, Ont.). 2017 10; 100(Pt 1):771-779. doi: 10.1016/j.foodres.2017.08.005. [PMID: 28873749]
  • B T Rovani, R B de Freitas, P R Augusti, I C Araldi, S Somacal, A Quatrin, T Emanuelli, M P da Rocha, L de Freitas Bauermann. Prooxidant activity of norbixin in model of acute gastric ulcer induced by ethanol in rats. Human & experimental toxicology. 2016 Jul; 35(7):737-46. doi: 10.1177/0960327115604199. [PMID: 26353805]
  • Valérie Fontaine, Elodie Monteiro, Elena Brazhnikova, Laëtitia Lesage, Christine Balducci, Louis Guibout, Laurence Feraille, Pierre-Paul Elena, José-Alain Sahel, Stanislas Veillet, René Lafont. Norbixin Protects Retinal Pigmented Epithelium Cells and Photoreceptors against A2E-Mediated Phototoxicity In Vitro and In Vivo. PloS one. 2016; 11(12):e0167793. doi: 10.1371/journal.pone.0167793. [PMID: 27992460]
  • Tucker J Smith, E Allen Foegeding, MaryAnne Drake. Sensory and Functionality Differences of Whey Protein Isolate Bleached by Hydrogen or Benzoyl Peroxide. Journal of food science. 2015 Oct; 80(10):C2153-60. doi: 10.1111/1750-3841.13000. [PMID: 26317318]
  • Y Qiu, T J Smith, E A Foegeding, M A Drake. The effect of microfiltration on color, flavor, and functionality of 80\% whey protein concentrate. Journal of dairy science. 2015 Sep; 98(9):5862-73. doi: 10.3168/jds.2014-9174. [PMID: 26188582]
  • M G Jervis, T J Smith, M A Drake. Short communication: The influence of solids concentration and bleaching agent on bleaching efficacy and flavor of sweet whey powder. Journal of dairy science. 2015 Apr; 98(4):2294-302. doi: 10.3168/jds.2014-8804. [PMID: 25660741]
  • R E Campbell, I A L A Boogers, M A Drake. Short communication: Development of a novel method for the extraction of norbixin from whey and its subsequent quantification via high performance liquid chromatography. Journal of dairy science. 2014 Mar; 97(3):1313-8. doi: 10.3168/jds.2013-7415. [PMID: 24377797]
  • T J Smith, X E Li, M A Drake. Short communication: norbixin and bixin partitioning in Cheddar cheese and whey. Journal of dairy science. 2014; 97(6):3321-7. doi: 10.3168/jds.2013-7614. [PMID: 24704237]
  • Yue Zhang, Qixin Zhong. Probing the binding between norbixin and dairy proteins by spectroscopy methods. Food chemistry. 2013 Aug; 139(1-4):611-6. doi: 10.1016/j.foodchem.2013.01.073. [PMID: 23561152]
  • Rachel E Campbell, Michael C Adams, Maryanne Drake, David M Barbano. Effect of bleaching permeate from microfiltered skim milk on 80\% serum protein concentrate. Journal of dairy science. 2013 Mar; 96(3):1387-400. doi: 10.3168/jds.2012-6053. [PMID: 23295111]
  • Tsuyoshi Goto, Nobuyuki Takahashi, Sota Kato, Young-Il Kim, Tatsuya Kusudo, Aki Taimatsu, Kahori Egawa, Min-Sook Kang, Takuro Hiramatsu, Tomoya Sakamoto, Taku Uemura, Shizuka Hirai, Misato Kobayashi, Fumihiko Horio, Teruo Kawada. Bixin activates PPARα and improves obesity-induced abnormalities of carbohydrate and lipid metabolism in mice. Journal of agricultural and food chemistry. 2012 Dec; 60(48):11952-8. doi: 10.1021/jf303639f. [PMID: 23145898]
  • Gustavo Rafael Mazzaron Barcelos, Denise Grotto, Juliana Mara Serpeloni, Alexandre Ferro Aissa, Lusânia Maria Greggi Antunes, Siegfried Knasmüller, Fernando Barbosa. Bixin and norbixin protect against DNA-damage and alterations of redox status induced by methylmercury exposure in vivo. Environmental and molecular mutagenesis. 2012 Aug; 53(7):535-41. doi: 10.1002/em.21715. [PMID: 22847942]
  • E J Kang, T J Smith, M A Drake. Alternative bleaching methods for Cheddar cheese whey. Journal of food science. 2012 Jul; 77(7):C818-23. doi: 10.1111/j.1750-3841.2012.02774.x. [PMID: 22757703]
  • S Jervis, R Campbell, K L Wojciechowski, E A Foegeding, M A Drake, D M Barbano. Effect of bleaching whey on sensory and functional properties of 80\% whey protein concentrate. Journal of dairy science. 2012 Jun; 95(6):2848-62. doi: 10.3168/jds.2011-4967. [PMID: 22612922]
  • R E Campbell, E J Kang, E Bastian, M A Drake. The use of lactoperoxidase for the bleaching of fluid whey. Journal of dairy science. 2012 Jun; 95(6):2882-90. doi: 10.3168/jds.2011-5166. [PMID: 22612925]
  • M A D Listiyani, R E Campbell, R E Miracle, D M Barbano, P D Gerard, M A Drake. Effect of temperature and bleaching agent on bleaching of liquid Cheddar whey. Journal of dairy science. 2012 Jan; 95(1):36-49. doi: 10.3168/jds.2011-4557. [PMID: 22192182]
  • Vanessa Cardeñosa, María Loreto Lunar, Soledad Rubio. Generalized and rapid supramolecular solvent-based sample treatment for the determination of annatto in food. Journal of chromatography. A. 2011 Dec; 1218(50):8996-9002. doi: 10.1016/j.chroma.2011.10.041. [PMID: 22071422]
  • Wimolnut Auttachoat, Dori R Germolec, Matthew J Smith, Kimber L White, Tai L Guo. Contact sensitizing potential of annatto extract and its two primary color components, cis-bixin and norbixin, in female BALB/c mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Oct; 49(10):2638-44. doi: 10.1016/j.fct.2011.07.009. [PMID: 21777644]
  • M A D Listiyani, R E Campbell, R E Miracle, L O Dean, M A Drake. Influence of bleaching on flavor of 34\% whey protein concentrate and residual benzoic acid concentration in dried whey proteins. Journal of dairy science. 2011 Sep; 94(9):4347-59. doi: 10.3168/jds.2011-4341. [PMID: 21854907]
  • R E Campbell, R E Miracle, M A Drake. The effect of starter culture and annatto on the flavor and functionality of whey protein concentrate. Journal of dairy science. 2011 Mar; 94(3):1185-93. doi: 10.3168/jds.2010-3789. [PMID: 21338784]
  • M Membrez, C J Chou, F Raymond, R Mansourian, M Moser, I Monnard, C Ammon-Zufferey, K Mace, G Mingrone, C Binnert. Six weeks' sebacic acid supplementation improves fasting plasma glucose, HbA1c and glucose tolerance in db/db mice. Diabetes, obesity & metabolism. 2010 Dec; 12(12):1120-6. doi: 10.1111/j.1463-1326.2010.01308.x. [PMID: 20977585]
  • Jennifer D Tibodeau, Crescent R Isham, Keith C Bible. Annatto constituent cis-bixin has selective antimyeloma effects mediated by oxidative stress and associated with inhibition of thioredoxin and thioredoxin reductase. Antioxidants & redox signaling. 2010 Oct; 13(7):987-97. doi: 10.1089/ars.2009.2896. [PMID: 20170403]
  • E J Kang, R E Campbell, E Bastian, M A Drake. Invited review: Annatto usage and bleaching in dairy foods. Journal of dairy science. 2010 Sep; 93(9):3891-901. doi: 10.3168/jds.2010-3190. [PMID: 20723662]
  • A Z Mercadante, C D Capitani, E A Decker, I A Castro. Effect of natural pigments on the oxidative stability of sausages stored under refrigeration. Meat science. 2010 Apr; 84(4):718-26. doi: 10.1016/j.meatsci.2009.10.031. [PMID: 20374848]
  • Tsuyoshi Goto, Nobuyuki Takahashi, Shizuka Hirai, Teruo Kawada. Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism. PPAR research. 2010; 2010(?):483958. doi: 10.1155/2010/483958. [PMID: 20613991]
  • Nobuyuki Takahashi, Tsuyoshi Goto, Aki Taimatsu, Kahori Egawa, Sota Katoh, Tatsuya Kusudo, Tomoya Sakamoto, Chie Ohyane, Joo-Young Lee, Young-Il Kim, Taku Uemura, Shizuka Hirai, Teruo Kawada. Bixin regulates mRNA expression involved in adipogenesis and enhances insulin sensitivity in 3T3-L1 adipocytes through PPARgamma activation. Biochemical and biophysical research communications. 2009 Dec; 390(4):1372-6. doi: 10.1016/j.bbrc.2009.10.162. [PMID: 19891958]
  • A E Croissant, E J Kang, R E Campbell, E Bastian, M A Drake. The effect of bleaching agent on the flavor of liquid whey and whey protein concentrate. Journal of dairy science. 2009 Dec; 92(12):5917-27. doi: 10.3168/jds.2009-2535. [PMID: 19923595]
  • H Noppe, S Abuin Martinez, K Verheyden, J Van Loco, R Companyo Beltran, H F De Brabander. Determination of bixin and norbixin in meat using liquid chromatography and photodiode array detection. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2009 Jan; 26(1):17-24. doi: 10.1080/02652030802322564. [PMID: 19680866]
  • Veronica Galindo-Cuspinera, Scott A Rankin. Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts. Journal of agricultural and food chemistry. 2005 Apr; 53(7):2524-9. doi: 10.1021/jf048056q. [PMID: 15796589]
  • A de Oliveira Rios, A Z Mercadante. Novel method for the determination of added annatto colour in extruded corn snack products. Food additives and contaminants. 2004 Feb; 21(2):125-33. doi: 10.1080/02652030310001642771. [PMID: 14754634]
  • A Hagiwara, N Imai, T Ichihara, M Sano, S Tamano, H Aoki, K Yasuhara, T Koda, M Nakamura, T Shirai. A thirteen-week oral toxicity study of annatto extract (norbixin), a natural food color extracted from the seed coat of annatto (Bixa orellana L.), in Sprague-Dawley rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Aug; 41(8):1157-64. doi: 10.1016/s0278-6915(03)00104-2. [PMID: 12842184]
  • M J Scotter, L Castle, C A Honeybone, C Nelson. Method development and analysis of retail foods for annatto food colouring material. Food additives and contaminants. 2002 Mar; 19(3):205-22. doi: 10.1080/02652030110085386. [PMID: 11834073]
  • K Kovary, T S Louvain, M C Costa e Silva, F Albano, B B Pires, G A Laranja, C L Lage, I Felzenszwalb. Biochemical behaviour of norbixin during in vitro DNA damage induced by reactive oxygen species. The British journal of nutrition. 2001 Apr; 85(4):431-40. doi: 10.1079/bjn2000287. [PMID: 11348557]
  • L W Levy, E Regalado, S Navarrete, R H Watkins. Bixin and norbixin in human plasma: determination and study of the absorption of a single dose of Annatto food color. The Analyst. 1997 Sep; 122(9):977-80. doi: 10.1039/a701304c. [PMID: 9374027]
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