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Bixin

Properties and Applications

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Handbook of Food Bioactive Ingredients

Abstract

Bixin is the first cis-carotenoid and an apocarotenoid to be known from nature which exists in the seed of achiote tree or annatto (Bixa orellana L.) belonging to the Bixaceae family that grows in the tropical countries. Bixin possesses high colorant range from reddish-orange tonality to yellow hues in the visible region. It is chemically unstable during isolation or in different thermal, light, pH, and oxygen conditions, then it converts into trans-bixin (β-bixin). Bixin is soluble in fats, alcohols, and organic solvents but insoluble in water and known as a hydrophobic compound. In the presence of alkali, the methyl ester of bixin is hydrolyzed and converted to norbixin, a water-soluble derivative. Bixin, as the most apocarotenoid constituent (70–80%) of annatto seeds, is used widely in food and drug industry, cosmetics, textiles, and as antioxidant or pharmacologic agent to manage various diseases and their underling signaling targets. It mediates multiple organ toxicity including cancer, metabolic syndrome, renal dysfunction, neurodegeneration, cardiovascular diseases, and inflammation related to their up/downstream signaling pathways by its antioxidant, anti-inflammatory, and antiapoptotic effects. Consequently, bixin is approved as canonical Nrf2 induction, PPAR α/γ agonist, and TLR4/NFκB antagonist. This chapter covers the bixin properties and applications thanks to its biological and financial benefits, in term of chemical and curing features, focusing on its pharmacological and molecular mechanism of action. Subsequently, it highlights animal and clinical studies on biological effects of bixin along with its dietary contribution.

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Notes

  1. 1.

    FDA: Food and Drug Administration.

  2. 2.

    PCR: Polymerase chain reaction.

  3. 3.

    IUPAC: International Union of Pure and Applied Chemistry.

  4. 4.

    HPLC: High-Performance Liquid Chromatography.

  5. 5.

    NMR: Nuclear Magnetic Resonance.

  6. 6.

    UV-vis: Ultraviolet-visible light.

  7. 7.

    DRIFTS: Diffuse Reflectance Infrared Fourier Transform Spectroscopy.

  8. 8.

    MS: Mass spectrometry.

  9. 9.

    UPLC-DAD-MS/MS: Ultraperformance liquid chromatography method with diode array detection coupled with tandem mass spectrometry.

  10. 10.

    DNA: Deoxyribonucleic Acid.

  11. 11.

    ATP: Adenosine triphosphate.

  12. 12.

    UVC: Ultraviolet light with wavelengths between 200 and 280 nm.

  13. 13.

    UVA: Ultraviolet light with wavelengths between 320 and 400 nm.

  14. 14.

    ADI: Acceptable daily intake.

  15. 15.

    WHO: World Health Organization.

  16. 16.

    CFU: Colony-forming unit.

  17. 17.

    eV: Electron-volt.

Abbreviations

A549:

Human lung cancer cell line

ACO:

Acyl-CoA oxidase

Acox1:

Acyl-CoA Oxidase 1

ADI:

Acceptable daily intake

Akt:

Protein kinase B

ALT:

Aminotransferase

ANP:

A-type natriuretic peptides

AOPP:

Advanced oxidation protein products

aP2:

Adipocyte-specific fatty acid–binding protein

ASC:

Apoptosis Speck-like protein containing a CARD

AST:

Aminotransferase

ATP:

Adenosine triphosphate

AWT:

Anterior wall thickness

Bax:

Bcl-2-associated X protein

BW:

Body weight

CAT:

Catalase

α-SMA:

Alpha smooth muscle actin

CD3 + :

Cluster of differentiation 3

CFU:

Colony-forming unit

COP:

Cholesterol oxidation products

CPT1:

Carnitine palmitoyl transferase 1

CPTII:

Carnitine palmitoyltransferase II

DNA:

Deoxyribonucleic acid

DRIFTS:

Diffuse Reflectance Infrared Fourier Transform Spectroscopy

EAE:

Experimental autoimmune encephalomyelitis

ECM:

Extracellular matrix

EF:

Ejection fraction

EMT:

Epithelial-mesenchymal transition

eV:

Electron-volt

FasL:

Fas and Fas Ligand

FAT/CD36:

Fatty acid translocase/CD36

FDA:

Food and Drug Administration

FN:

Fibronectin

FS:

Fractional shortening

GAL4:

Gal4 transcription factor

GATA4:

GATA Binding Protein 4

GCLM:

Glutamate cysteine ligase modifier

GPx:

Glutathione peroxidase

GR:

Glutathione reductase

GSH:

Glutathione

HbA1:

Blood glycated hemoglobin

H9C2:

Human cardiac muscle cell

HDL:

High-density lipoprotein

HeLa:

Human cervical cancer cell line

HFD:

High-fat diet group

HMVEC-L:

Normal lung microvascular endothelial cells

HO-1:

Heme oxygenase-1

HOMA-IR:

Homeostasis model assessment of insulin resistance

HPLC:

High-Performance Liquid Chromatography

IBA1:

Ionized calcium binding adaptor molecule 1

IC50:

Half-maximal inhibitory concentration

IFN-γ:

Interferon gamma

IL-1β:

Interleukin-1β

IP:

Intraperionetally

IUPAC:

International Union of Pure and Applied Chemistry

Keap1:

Kelch-like ECH-associated protein 1

Ki67:

A nuclear protein that is tightly linked to the cell cycle (marker of cell proliferation)

LDL:

Low-density lipoprotein

LOOH:

Lipid hydroperoxides

LPL:

Lipoprotein lipase

LVEDd:

Left ventricular end-diastolic diameter

LVESd:

Left ventricular end-systolic diameter

LVSP:

Left ventricular systolic pressure

MBP:

Myelin basic protein

MDA:

Malondialdehyde

MMP:

Mitochondrial membrane potential

MMP9:

Matrix metalloproteinase 9

MPO:

Myeloperoxidase

MS:

Mass Spectrometry

MyD88:

Myeloid differentiation primary response gene 88

NF-κBp65:

Nuclear factor-κB p65

NFATc3:

Nuclear factor of activated T cells isoforms c3

NHBE:

Normal human bronchial epithelial cells

NLRP3:

NOD-like receptor family pyrin domain containing 3

NMR:

Nuclear Magnetic Resonance

NOx:

Nitric oxide metabolites

NPSH:

Nonprotein sulfhydryl groups

NQO1:

NADPH quinone oxidoreductase

Nrf2:

Nuclear factor erythroid 2-related factor 2

PCO:

Protein carbonyl groups

PCR:

Polymerase chain reaction

PI3K:

Phosphatidylinositol 3–kinase

PON1:

Paraoxonase 1

PPAR-γ:

Peroxisome proliferator-activated receptor gamma

RBC:

Red blood cells

R f :

Retardation factor

ROS:

Reactive oxygen species

S/F:

Solvent mass to feed mass

SiGel:

Silica gel

SiO2:

Silica dioxide

SOD:

Superoxide anion dismutase

Smad3:

SMAD family member 3

STAT6:

Signal transducer and activator of transcription 6

STZ:

Streptozotocin

TBARS:

Thiobarbituric acid reactive substance

TC:

Total cholesterol

TFA:

Trifluoracetic acid

TG:

Triacylglycerol

TGF-β:

Transforming growth factor β

Th:

T helper

TLR4:

Toll-like receptor 4

TNFα:

Tumor necrosis factor-alpha

TOS:

Total oxidant status

TrxR-1:

Thioredoxin reductase-1

TXNIP:

Thioredoxin interacting protein

UCP2:

Uncoupling protein-2

UPLC-DAD-MS/MS:

Ultraperformance liquid chromatography method with diode array detection coupled with tandem mass spectrometry

UUO:

Unilateral ureteral obstruction

UV-vis:

Ultraviolet-visible light

UVA:

Ultraviolet light with wavelengths between 320 and 400 nm

UVC:

Ultraviolet light with wavelengths between 200 and 280 nm

WHO:

World Health Organization

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Enayati, A., Assadpour, E., Jafari, S.M. (2023). Bixin. In: Jafari, S.M., Rashidinejad, A., Simal-Gandara, J. (eds) Handbook of Food Bioactive Ingredients. Springer, Cham. https://doi.org/10.1007/978-3-030-81404-5_56-1

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