alpha-Bixin (BioDeep_00000003867)

Main id: BioDeep_00000407566

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid

化学式: C25H30O4 (394.2144)
中文名称: 胭脂树橙
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=CC(=O)OC)C=CC=C(C)C=CC(=O)O
InChI: InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-

描述信息

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
Principal colouring matter of Bixa orellana (annatto) seeds [DFC]
Principal colouring matter of Bixa orellana (annatto) seeds.
Bixin (BX), isolated from the seeds of Bixa orellana, is a carotenoid, possessing anti-inflammatory, anti-tumor and anti-oxidant activities. Bixin treatment ameliorated cardiac dysfunction through inhibiting fibrosis, inflammation and reactive oxygen species (ROS) generation[1].

同义名列表

15 个代谢物同义名

(2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid; Methyl (9-cis)-hydrogen-6,6-diapo-psi,psi-carotenedioic acid; 6-Methyl hydrogen 9-cis-6,6-diapocarotene-6,6-dioic acid; Methyl (9-cis)-hydrogen-6,6-diapo-psi,psi-carotenedioate; 6-Methyl hydrogen 9-Z-6,6-diapocarotene-6,6-dioic acid; 6-Methyl hydrogen 9-cis-6,6-diapocarotene-6,6-dioate; 6-Methyl hydrogen 9-Z-6,6-diapocarotene-6,6-dioate; Stable bixin; alpha-Bixin; cis-Bixin; Isobixin; a-Bixin; Α-bixin; Bixin; Bixin



数据库引用编号

16 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)

22 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 14 BRAF, CAT, CYP1A1, KEAP1, MYD88, NFE2L2, NLRP3, PIK3CA, PPARG, SMAD3, SRARP, TLR4, TP53, TXNIP
Peripheral membrane protein 1 CYP1A1
Endosome membrane 2 MYD88, TLR4
Endoplasmic reticulum membrane 1 CYP1A1
Nucleus 10 BRAF, KEAP1, MYD88, NFE2L2, NLRP3, PPARA, PPARG, SMAD3, SRARP, TP53
cytosol 12 BRAF, CAT, GSR, KEAP1, MYD88, NFE2L2, NLRP3, PIK3CA, PPARG, SMAD3, TP53, TXNIP
centrosome 2 NFE2L2, TP53
nucleoplasm 6 KEAP1, NFE2L2, PPARA, PPARG, SMAD3, TP53
RNA polymerase II transcription regulator complex 2 NFE2L2, PPARG
Cell membrane 3 BRAF, TLR4, TNF
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 NLRP3
cell surface 3 MYD88, TLR4, TNF
glutamatergic synapse 1 BRAF
Golgi apparatus 1 NFE2L2
Golgi membrane 2 INS, NLRP3
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 TNF
postsynapse 1 BRAF
Cytoplasm, cytosol 2 NFE2L2, NLRP3
Presynapse 1 BRAF
plasma membrane 7 BRAF, MYD88, NFE2L2, PIK3CA, SMAD3, TLR4, TNF
Membrane 4 CAT, NLRP3, TLR4, TP53
extracellular exosome 3 CAT, GSR, MMP9
endoplasmic reticulum 3 KEAP1, NLRP3, TP53
extracellular space 4 IL6, INS, MMP9, TNF
perinuclear region of cytoplasm 3 PIK3CA, PPARG, TLR4
intercalated disc 1 PIK3CA
mitochondrion 6 BRAF, CAT, CYP1A1, GSR, NLRP3, TP53
protein-containing complex 3 CAT, MYD88, TP53
intracellular membrane-bounded organelle 4 BRAF, CAT, CYP1A1, PPARG
Microsome membrane 1 CYP1A1
Single-pass type I membrane protein 1 TLR4
Secreted 3 IL6, INS, NLRP3
extracellular region 6 CAT, IL6, INS, MMP9, NLRP3, TNF
Mitochondrion matrix 1 TP53
mitochondrial matrix 3 CAT, GSR, TP53
transcription regulator complex 2 SMAD3, TP53
centriolar satellite 1 KEAP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
external side of plasma membrane 3 GSR, TLR4, TNF
Secreted, extracellular space, extracellular matrix 1 MMP9
nucleolus 1 TP53
midbody 1 KEAP1
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 CAT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 1 MMP9
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
nuclear inner membrane 1 SMAD3
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 3 PPARG, SMAD3, TLR4
neuron projection 1 BRAF
chromatin 5 NFE2L2, PPARA, PPARG, SMAD3, TP53
mediator complex 1 NFE2L2
phagocytic cup 2 TLR4, TNF
actin filament 1 KEAP1
site of double-strand break 1 TP53
Cul3-RING ubiquitin ligase complex 1 KEAP1
Endomembrane system 1 NLRP3
endosome lumen 1 INS
microtubule organizing center 1 NLRP3
cell body 1 BRAF
germ cell nucleus 1 TP53
replication fork 1 TP53
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 2 CAT, MMP9
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
tertiary granule lumen 1 MMP9
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
[Isoform 1]: Nucleus 1 TP53
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
heteromeric SMAD protein complex 1 SMAD3
SMAD protein complex 1 SMAD3
protein-DNA complex 1 NFE2L2
extrinsic component of plasma membrane 1 MYD88
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Kleiton Lima de Godoy Machado, Daniele Vidal Faria, Marcos Bruno Silva Duarte, Lázara Aline Simões Silva, Tadeu Dos Reis de Oliveira, Thais Castilho Arruda Falcão, Diego Silva Batista, Marcio Gilberto Cardoso Costa, Claudete Santa-Catarina, Vanildo Silveira, Elisson Romanel, Wagner Campos Otoni, Fabio Tebaldi Silveira Nogueira. Plant age-dependent dynamics of annatto pigment (bixin) biosynthesis in Bixa orellana L. Journal of experimental botany. 2023 Nov; ?(?):. doi: 10.1093/jxb/erad458. [PMID: 37975812]
  • Asma Ashraf, Muhammad Umar Ijaz, Saima Muzammil, Muhammad Muzammil Nazir, Saima Zafar, S M Neamul Kabir Zihad, Shaikh Jamal Uddin, Md Saquib Hasnain, Amit Kumar Nayak. The role of bixin as antioxidant, anti-inflammatory, anticancer, and skin protecting natural product extracted from Bixa orellana L. Fitoterapia. 2023 Jul; 169(?):105612. doi: 10.1016/j.fitote.2023.105612. [PMID: 37454777]
  • Ayesheh Enayati, Atefe Rezaei, Seid Reza Falsafi, Hadis Rostamabadi, Narjes Malekjani, Sahar Akhavan-Mahdavi, Mohammad Saeed Kharazmi, Seid Mahdi Jafari. Bixin-loaded colloidal nanodelivery systems, techniques and applications. Food chemistry. 2023 Jan; 412(?):135479. doi: 10.1016/j.foodchem.2023.135479. [PMID: 36709686]
  • Lia Kusmita, Yuvianti Dwi Franyoto, Mutmainah Mutmainah, Ika Puspitaningrum, Agustina D R Nurcahyanti. Bixa orellana L. carotenoids: antiproliferative activity on human lung cancer, breast cancer, and cervical cancer cells in vitro. Natural product research. 2022 Dec; 36(24):6421-6427. doi: 10.1080/14786419.2022.2036144. [PMID: 35133226]
  • Alexia Thamara Gasparin, Evelize Stacoviaki Rosa, Carlos Henrique Alves Jesus, Izonete Cristina Guiloski, Helena Cristina da Silva de Assis, Olair Carlos Beltrame, Rosângela Locatelli Dittrich, Samanta Daliana Golin Pacheco, Janaina Menezes Zanoveli, Joice Maria da Cunha. Bixin attenuates mechanical allodynia, anxious and depressive-like behaviors associated with experimental diabetes counteracting oxidative stress and glycated hemoglobin. Brain research. 2021 09; 1767(?):147557. doi: 10.1016/j.brainres.2021.147557. [PMID: 34107278]
  • Qian Lou, Xiangdong Pu, Jingyuan Song. [Advances in the biosynthesis and application of bixin]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2021 Jun; 37(6):1986-1997. doi: 10.13345/j.cjb.200724. [PMID: 34227289]
  • Darío R Gómez-Linton, Silvestre Alavez, Arturo Navarro-Ocaña, Angélica Román-Guerrero, Luis Pinzón-López, Laura J Pérez-Flores. Achiote (Bixa orellana) Lipophilic Extract, Bixin, and δ-tocotrienol Effects on Lifespan and Stress Resistance in Caenorhabditis elegans. Planta medica. 2021 Apr; 87(5):368-374. doi: 10.1055/a-1266-6674. [PMID: 33124008]
  • Ana María Naranjo-Durán, Julián Quintero-Quiroz, John Rojas-Camargo, Gelmy Luz Ciro-Gómez. Modified-release of encapsulated bioactive compounds from annatto seeds produced by optimized ionic gelation techniques. Scientific reports. 2021 01; 11(1):1317. doi: 10.1038/s41598-020-80119-1. [PMID: 33446706]
  • Jie-Qiong Ma, Yu-Jia Zhang, Zhi-Kai Tian, Chan-Min Liu. Bixin attenuates carbon tetrachloride induced oxidative stress, inflammation and fibrosis in kidney by regulating the Nrf2/TLR4/MyD88 and PPAR-γ/TGF-β1/Smad3 pathway. International immunopharmacology. 2021 Jan; 90(?):107117. doi: 10.1016/j.intimp.2020.107117. [PMID: 33162346]
  • Shasha Tao, Youjing Yang, Jianzhong Li, Hongyan Wang, Yu Ma. Bixin Attenuates High-Fat Diet-Caused Liver Steatosis and Inflammatory Injury through Nrf2/PPARα Signals. Oxidative medicine and cellular longevity. 2021; 2021(?):6610124. doi: 10.1155/2021/6610124. [PMID: 33603948]
  • Jianzhong Li, Youjing Yang, Shuhui Wei, Ling Chen, Lian Xue, Hailin Tian, Shasha Tao. Bixin Confers Prevention against Ureteral Obstruction-Caused Renal Interstitial Fibrosis through Activation of the Nuclear Factor Erythroid-2-Related Factor2 Pathway in Mice. Journal of agricultural and food chemistry. 2020 Aug; 68(31):8321-8329. doi: 10.1021/acs.jafc.0c03674. [PMID: 32706966]
  • 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]
  • Suparmi Suparmi, Laura de Haan, Albertus Spenkelink, Jochem Louisse, Karsten Beekmann, Ivonne M C M Rietjens. Combining In Vitro Data and Physiologically Based Kinetic Modeling Facilitates Reverse Dosimetry to Define In Vivo Dose-Response Curves for Bixin- and Crocetin-Induced Activation of PPARγ in Humans. Molecular nutrition & food research. 2020 01; 64(2):e1900880. doi: 10.1002/mnfr.201900880. [PMID: 31846197]
  • Daniele Vidal Faria, Ludmila Nayara de Freitas Correia, Maria Victoria Costa Souza, Anyela Marcela Ríos-Ríos, Camilo Elber Vital, Diego Silva Batista, Marcio Gilberto Cardoso Costa, Wagner Campos Otoni. Irradiance and light quality affect two annatto (Bixa orellana L.) cultivars with contrasting bixin production. Journal of photochemistry and photobiology. B, Biology. 2019 Aug; 197(?):111549. doi: 10.1016/j.jphotobiol.2019.111549. [PMID: 31302348]
  • M Sankari, H Hridya, P Sneha, C George Priya Doss, J Godwin Christopher, Jill Mathew, Hatem Zayed, Siva Ramamoorthy. Implication of salt stress induces changes in pigment production, antioxidant enzyme activity, and qRT-PCR expression of genes involved in the biosynthetic pathway of Bixa orellana L. Functional & integrative genomics. 2019 Jul; 19(4):565-574. doi: 10.1007/s10142-019-00654-7. [PMID: 30694406]
  • Raimundo Gonçalves de Oliveira Júnior, Antoine Bonnet, Estelle Braconnier, Hugo Groult, Grégoire Prunier, Laureen Beaugeard, Raphäel Grougnet, Jackson Roberto Guedes da Silva Almeida, Christiane Adrielly Alves Ferraz, Laurent Picot. Bixin, an apocarotenoid isolated from Bixa orellana L., sensitizes human melanoma cells to dacarbazine-induced apoptosis through ROS-mediated cytotoxicity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Mar; 125(?):549-561. doi: 10.1016/j.fct.2019.02.013. [PMID: 30738990]
  • Ana Delia Pinzón-García, Laura Alejandra Ariza Orellano, Marcela Guimarães Takahashi de Lazari, Paula Peixoto Campos, Maria Esperanza Cortes, Ruben Dario Sinisterra. Evidence of hypoglycemic, lipid-lowering and hepatoprotective effects of the Bixin and Bixin: β-CD inclusion compound in high-fat-fed obese mice. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Oct; 106(?):363-372. doi: 10.1016/j.biopha.2018.06.144. [PMID: 29966982]
  • Antônio P R Bitencourt, Jonatas L Duarte, Anna E M F M Oliveira, Rodrigo A S Cruz, José C T Carvalho, Antônio T A Gomes, Irlon M Ferreira, Roseane M Ribeiro-Costa, José O C Silva-Júnior, Caio P Fernandes. Preparation of aqueous nanodispersions with annatto (Bixa orellana L.) extract using an organic solvent-free and low energy method. Food chemistry. 2018 Aug; 257(?):196-205. doi: 10.1016/j.foodchem.2018.02.067. [PMID: 29622198]
  • Jaime A Teixeira da Silva, Judit Dobránszki, Renata Rivera-Madrid. The biotechnology (genetic transformation and molecular biology) of Bixa orellana L. (achiote). Planta. 2018 Aug; 248(2):267-277. doi: 10.1007/s00425-018-2909-7. [PMID: 29748818]
  • Sankari Mohan, Hridya Hemachandran, P Sneha, C George Priya Doss, J Godwin Christopher, Gurunathan Jayaraman, Siva Ramamoorthy. Structural insights into the binding mode and conformational changes of BSA induced by bixin and crocin. Journal of biomolecular structure & dynamics. 2018 Jun; 36(8):2085-2098. doi: 10.1080/07391102.2017.1342565. [PMID: 28665186]
  • Montserrat Rojo de la Vega, Andrea Krajisnik, Donna D Zhang, Georg T Wondrak. Targeting NRF2 for Improved Skin Barrier Function and Photoprotection: Focus on the Achiote-Derived Apocarotenoid Bixin. Nutrients. 2017 Dec; 9(12):. doi: 10.3390/nu9121371. [PMID: 29258247]
  • M Sankari, H Hridya, P Sneha, C George Priya Doss, Siva Ramamoorthy. Effect of UV radiation and its implications on carotenoid pathway in Bixa orellana L. Journal of photochemistry and photobiology. B, Biology. 2017 Nov; 176(?):136-144. doi: 10.1016/j.jphotobiol.2017.10.002. [PMID: 28992607]
  • 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]
  • Sylvia C Alcázar-Alay, J Felipe Osorio-Tobón, Tânia Forster-Carneiro, M Angela A Meireles. Obtaining bixin from semi-defatted annatto seeds by a mechanical method and solvent extraction: Process integration and economic evaluation. Food research international (Ottawa, Ont.). 2017 09; 99(Pt 1):393-402. doi: 10.1016/j.foodres.2017.05.032. [PMID: 28784497]
  • Renata Pires Assis, Carlos Alberto Arcaro, Vânia Ortega Gutierres, Juliana Oriel Oliveira, Paulo Inácio Costa, Amanda Martins Baviera, Iguatemy Lourenço Brunetti. Combined Effects of Curcumin and Lycopene or Bixin in Yoghurt on Inhibition of LDL Oxidation and Increases in HDL and Paraoxonase Levels in Streptozotocin-Diabetic Rats. International journal of molecular sciences. 2017 Mar; 18(4):. doi: 10.3390/ijms18040332. [PMID: 28333071]
  • Luceia Fatima Souza, Niara da Silva Medeiros, Paula Cilene Pereira Dos Santos, Carlos Henrique Pagno, Cleice Dalla Nora, Erna Vogt de Jong, Alessandro de Oliveira Rios. Antioxidants from Annatto Seeds as Possible Inhibitory Agents of the Hepatotoxicity Induced by the Antitumor Agent Cisplatin. Natural product communications. 2016 Sep; 11(9):1233-1236. doi: . [PMID: 30807008]
  • Mohan Sankari, Hridya Hemachandran, Amirtha Anantharaman, Subramanian Babu, Renata Rivera Madrid, George Priya Doss C, Devanand P Fulzele, Ramamoorthy Siva. Identifying a Carotenoid Cleavage Dioxygenase 4a Gene and Its Efficient Agrobacterium-Mediated Genetic Transformation in Bixa orellana L. Applied biochemistry and biotechnology. 2016 Jul; 179(5):697-714. doi: 10.1007/s12010-016-2025-8. [PMID: 26922728]
  • J S Park, B D Mathison, B M Zawlocki, B P Chew. Bixin uptake and antioxidative effect and role in immunoregulation in domestic cats. Journal of animal science. 2016 Jan; 94(1):125-34. doi: 10.2527/jas.2015-9478. [PMID: 26812319]
  • J S Park, B D Mathison, B P Chew. Uptake and immunomodulatory role of bixin in dogs. Journal of animal science. 2016 Jan; 94(1):135-43. doi: 10.2527/jas.2015-9479. [PMID: 26812320]
  • Yair Cárdenas-Conejo, Víctor Carballo-Uicab, Meric Lieberman, Margarita Aguilar-Espinosa, Luca Comai, Renata Rivera-Madrid. De novo transcriptome sequencing in Bixa orellana to identify genes involved in methylerythritol phosphate, carotenoid and bixin biosynthesis. BMC genomics. 2015 Oct; 16(?):877. doi: 10.1186/s12864-015-2065-4. [PMID: 26511010]
  • Bruno C Figueirêdo, Neura Bragagnolo, Leif H Skibsted, Vibeke Orlien. Inhibition of Cholesterol and Polyunsaturated Fatty Acids Oxidation through the Use of Annatto and Bixin in High-Pressure Processed Fish. Journal of food science. 2015 Aug; 80(8):C1646-53. doi: 10.1111/1750-3841.12964. [PMID: 26219922]
  • Sabrina Somacal, Cassieli G Figueiredo, Andréia Quatrin, Amanda R Ruviaro, Lisiane Conte, Paula R Augusti, Miguel Roehrs, Ione T Denardin, Jocieli Kasten, Marcelo L da Veiga, Marta M F Duarte, Tatiana Emanuelli. The antiatherogenic effect of bixin in hypercholesterolemic rabbits is associated to the improvement of lipid profile and to its antioxidant and anti-inflammatory effects. Molecular and cellular biochemistry. 2015 May; 403(1-2):243-53. doi: 10.1007/s11010-015-2354-x. [PMID: 25702177]
  • Madipatla Prathyusha Rao, Kopparam Manjunath, Siddalingappa Tippanna Bhagawati, Boreddy Shivanandappa Thippeswamy. Bixin loaded solid lipid nanoparticles for enhanced hepatoprotection--preparation, characterisation and in vivo evaluation. International journal of pharmaceutics. 2014 Oct; 473(1-2):485-92. doi: 10.1016/j.ijpharm.2014.07.027. [PMID: 25066077]
  • Priscila R Moreira, Marcos A Maioli, Hyllana C D Medeiros, Marieli Guelfi, Flávia T V Pereira, Fábio E Mingatto. Protective effect of bixin on carbon tetrachloride-induced hepatotoxicity in rats. Biological research. 2014 Sep; 47(?):49. doi: 10.1186/0717-6287-47-49. [PMID: 25299839]
  • Pollyanna Francielli de Oliveira, Kelly Jacqueline Barbosa de Andrade, Marcela Cristina Ferreira Paula, Nathália Oliveira Acésio, Thais da Silva Moraes, Priscilla Scalon Freitas Borges, Gustavo Rafael Mazzaron Barcelos, Denise Crispim Tavares. Bixin protects hepatocytes against 1,2-dimethylhydrazine-induced genotoxicity but does not suppress DNA damage and pre-neoplastic lesions in the colon of Wistar rats. Mutation research. Genetic toxicology and environmental mutagenesis. 2014 Jan; 759(?):37-42. doi: 10.1016/j.mrgentox.2013.07.017. [PMID: 24246722]
  • 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]
  • Renata Machado Piva, Aline Cristina Batista Rodrigues Johann, Camila Kocler Costa, Obdulio Gomez Miguel, Edvaldo Ribeiro Rosa, Luciana Reis de Azevedo-Alanis, Paula Cristina Trevilatto, Sergio Aparecido Ignacio, Patrícia Vida Cassi Bettega, Ana Maria Trindade Gregio. Bixin action in the healing process of rats mouth wounds. Current pharmaceutical biotechnology. 2013; 14(9):785-91. doi: 10.2174/1389201014666131227111026. [PMID: 24372269]
  • 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]
  • Ramasamy S Annadurai, Vasanthan Jayakumar, Raja C Mugasimangalam, Mohan A V S K Katta, Sanchita Anand, Sreeja Gopinathan, Santosh Prasad Sarma, Sunjay Jude Fernandes, Nandita Mullapudi, S Murugesan, Sudha Narayana Rao. Next generation sequencing and de novo transcriptome analysis of Costus pictus D. Don, a non-model plant with potent anti-diabetic properties. BMC genomics. 2012 Nov; 13(?):663. doi: 10.1186/1471-2164-13-663. [PMID: 23176672]
  • 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]
  • Yue Zhang, Qixin Zhong. Effects of thermal denaturation on binding between bixin and whey protein. Journal of agricultural and food chemistry. 2012 Aug; 60(30):7526-31. doi: 10.1021/jf3021656. [PMID: 22784187]
  • Kazuhiro Tsuruma, Hiroki Shimazaki, Ken-Ichi Nakashima, Mika Yamauchi, Sou Sugitani, Masamitsu Shimazawa, Munekazu Iinuma, Hideaki Hara. Annatto prevents retinal degeneration induced by endoplasmic reticulum stress in vitro and in vivo. Molecular nutrition & food research. 2012 May; 56(5):713-24. doi: 10.1002/mnfr.201100607. [PMID: 22648618]
  • Yue Zhang, Qixin Zhong. Binding between bixin and whey protein at pH 7.4 studied by spectroscopy and isothermal titration calorimetry. Journal of agricultural and food chemistry. 2012 Feb; 60(7):1880-6. doi: 10.1021/jf2050262. [PMID: 22268806]
  • 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]
  • N L Rodríguez-Ávila, J A Narváez-Zapata, J E Ramírez-Benítez, M L Aguilar-Espinosa, R Rivera-Madrid. Identification and expression pattern of a new carotenoid cleavage dioxygenase gene member from Bixa orellana. Journal of experimental botany. 2011 Nov; 62(15):5385-95. doi: 10.1093/jxb/err201. [PMID: 21813796]
  • 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]
  • Renata Aparecida Soriano Sancho, Fabíola Aliaga de Lima, Gabriel Guerra Costa, Lilian Regina Barros Mariutti, Neura Bragagnolo. Effect of annatto seed and coriander leaves as natural antioxidants in fish meatballs during frozen storage. Journal of food science. 2011 Aug; 76(6):C838-45. doi: 10.1111/j.1750-3841.2011.02224.x. [PMID: 22417481]
  • 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]
  • Yunbao Liu, Muraleedharan G Nair. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products. 2010 Jul; 73(7):1193-5. doi: 10.1021/np1000945. [PMID: 20565070]
  • 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]
  • 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]
  • Jens Rehbein, Benjamin Dietrich, Marc David Grynbaum, Petra Hentschel, Karsten Holtin, Maximilian Kuehnle, Paul Schuler, Marc Bayer, Klaus Albert. Characterization of bixin by LC-MS and LC-NMR. Journal of separation science. 2007 Oct; 30(15):2382-90. doi: 10.1002/jssc.200700089. [PMID: 17763517]
  • Carla Bittencourt, Marcella P Felicissimo, Jean-Jacques Pireaux, Laurent Houssiau. ToF-SIMS characterization of thermal modifications of bixin from Bixa orellana fruit. Journal of agricultural and food chemistry. 2005 Aug; 53(16):6195-200. doi: 10.1021/jf0505271. [PMID: 16076093]
  • Ferenc Zsila, Péter Molnár, József Deli, Samuel F Lockwood. Circular dichroism and absorption spectroscopic data reveal binding of the natural cis-carotenoid bixin to human alpha1-acid glycoprotein. Bioorganic chemistry. 2005 Aug; 33(4):298-309. doi: 10.1016/j.bioorg.2005.03.003. [PMID: 16023489]
  • Ferenc Zsila, Péter Molnár, József Deli. Analysis of binding interaction between the natural apocarotenoid bixin and human serum albumin by circular dichroism and fluorescence spectroscopy. Chemistry & biodiversity. 2005 Jun; 2(6):758-72. doi: 10.1002/cbdv.200590053. [PMID: 17192019]
  • A C A X De-Oliveira, I B Silva, D A Manhaes-Rocha, F J R Paumgartten. Induction of liver monooxygenases by annatto and bixin in female rats. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2003 Jan; 36(1):113-8. doi: 10.1590/s0100-879x2003000100015. [PMID: 12532234]
  • 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]
  • C R Silva, L M Antunes, M L Bianchi. Antioxidant action of bixin against cisplatin-induced chromosome aberrations and lipid peroxidation in rats. Pharmacological research. 2001 Jun; 43(6):561-6. doi: 10.1006/phrs.2001.0822. [PMID: 11419966]
  • C Jewell, N M O'Brien. Effect of dietary supplementation with carotenoids on xenobiotic metabolizing enzymes in the liver, lung, kidney and small intestine of the rat. The British journal of nutrition. 1999 Mar; 81(3):235-42. doi: . [PMID: 10434850]
  • 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]
  • K C Thresiamma, J George, R Kuttan. Protective effect of curcumin, ellagic acid and bixin on radiation induced toxicity. Indian journal of experimental biology. 1996 Sep; 34(9):845-7. doi: . [PMID: 9014516]
  • L X Zhang, R V Cooney, J S Bertram. Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: relationship to their cancer chemopreventive action. Carcinogenesis. 1991 Nov; 12(11):2109-14. doi: 10.1093/carcin/12.11.2109. [PMID: 1934296]
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