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α-Parinaric acid is a conjugated polyunsaturated fatty acid.
Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds.
The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH2−).
CAS Number: 593-38-4
IUPAC Name: (9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid
Chemical Formula: C18H28O2
Molar Mass: 276.41372
Other names: cis-parinaric acid, alpha-parinaric acid, 593-38-4, cis-Parinaric acid [MI], (9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid, UNII-KM4KXM284R, 9Z,11E,13E,15Z-octadecatetraenoic acid, KM4KXM284R, .ALPHA.-PARINARIC ACID, PARINARIC ACID, (Z)-, (9Z,11E,13E,15Z)-9,11,13,15-Octadecatetraenoic acid, CHEBI:32409, PARINARIC ACID CIS-FORM [MI], (9Z,11E,13E,15Z)-octadecatetraenoic acid, 18427-44-6, C18:4n-3,5,7,9, 9,11,13,15-Octadecatetraenoic acid, (9Z,11E,13E,15Z)-, a-Parinarate, a-parinaric acid, a-Parinarinsaeure, alpha-Parinarinsaeure, (Z)-parinaric acid, SCHEMBL516994, PARINARIC ACID CIS-FORM, CHEMBL3785424, Parinaric acid, (all-e)-isomer, DTXSID501027236, HMS3650B15, 9c11t13t15c-18:4, HY-N7858, Parinaric acid, (Z,Z,e,e)-isomer, LMFA01030764, Octadeca-9c,11t,13t,15c-tetraensaeure, (9Z,11E,13E,15Z)-Octadecatetraenoate, octadeca-9c,11t,13t,15c-tetraenoic acid, C18:4, n-3 cis, 5 cis, 7 trans, 9 trans, SR-01000946323, (Z,E,E,Z)-octadeca-9,11,13,15-tetraenoic acid, Q2823297, SR-01000946323-1, cis,trans,trans,cis-Octadeca-9,11,13,15-tetraenoate, 9,11,13,15-cis,trans,trans,cis-octadecatetraenoic acid, 9-cis,11-trans,13-trans,15-cis-octadecatetraenoic acid, cis-9,trans-11,trans-13,cis-15-Octadecatetraensaeure, cis,trans,trans,cis-octadeca-9,11,13,15-tetraenoic acid
Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.
α-Parinaric acid occurs naturally in the seeds of the makita tree (Parinari laurina), a tree found in Fiji and other Pacific islands.
Makita seeds contain about 46% α-parinaric acid, 34% α-eleostearic acid as major components, with lesser amounts of saturated fatty acids, oleic acid and linoleic acid.
α-Parinaric acid is also found in the seed oil of Impatiens balsamina, a member of the family Balsaminaceae.
The major fatty acids of Impatiens balsamina are 4.7% palmitic acid, 5.8% stearic acid, 2.8% arachidic acid, 18.3% oleic acid, 9.2% linoleic acid, 30.1% linolenic acid and 29.1% α-parinaric acid.
α-Parinaric acid is also present in the fungus Clavulina cristata, and the plant Sebastiana brasiliensis (family Euphorbiaceae).
Biosynthesis
The biochemical mechanism by which α-parinaric acid is formed in the plant Impatiens balsamina was elaborated using techniques of molecular biology. The enzyme responsible for the creation of the conjugated double bonds was identified using expressed sequence tags, and called a "conjugase". This enzyme is related to the family of fatty acid desaturase enzymes responsible for putting double bonds into fatty acids.
Chemical synthesis
α-Parinaric acid may be synthesized chemically using α-linolenic acid as a starting compound.
This synthesis enables the transformation of 1,4,7-octatriene methylene-interrupted cis double bonds of naturally occurring polyunsaturated fatty acids to 1,3,5,7-octatetraenes in high yield.
More recently (2008), Lee et al. reported a simple and efficient chemical synthesis using a modular design method called iterative cross-coupling.
Uses
Membrane probes
Both the alpha and beta (all trans) isomers of parinaric acid are used as molecular probes of lipid-lipid interactions, by monitoring phase transitions in bilayer lipid membranes.
α-Parinaric acid was shown to integrate normally into the phospholipid bilayer of mammalian cells, nervous tissue, with minimal effects on the biophysical properties of the membrane. Molecular interactions with neighboring membrane lipids will affect the fluorescence of α-parinaric acid in predictable ways, and the subsequent subtle changes in energy intensities may be measured spectroscopically.
Researchers have put α-parinaric to good use in the study of membrane biophysics. For example, it was used to help establish the existence of a "fluidity gradient" across the membrane bilayer of some tumor cells ― the inner monolayer of the membrane is less fluid than the outer monolayer.[12]
Lipid-protein interactions
α-Parinaric acid is also used as a chromophore to study interactions between membrane proteins and lipids. Because of the similarity of α-parinaric acid to normal membrane lipids, it has minimal perturbing influence.
By measuring shifts in the absorption spectrum, enhancement of α-parinaric acid fluorescence, induced circular dichroism, and energy transfer between tryptophan amino acids in the protein and the bound chromophore, information may be gleaned about the molecular interactions between protein and lipid.
For example, this technique is used to investigate how fatty acids bind to serum albumin (a highly abundant blood protein), lipid transport processes including structural characterization of lipoproteins, and phospholipid-transfer proteins.
Clinical uses
The concentrations of fatty acids in blood serum or plasma can be measured using α-parinaric acid, which will compete for binding sites on serum albumin.
Food chemistry
α-Parinaric acid has been used to study the hydrophobicity and foaming characteristics of food proteins, as well as the foam stability of beer.
In this latter research, α-parinaric acid was used in a fluorescent assay to assess the lipid–binding potential of the proteins in the beer, as these proteins help protect beer from foam–reducing medium– and long–chain fatty acids.
Cytotoxic effects on tumor cells
α-Parinaric acid is cytotoxic to human leukemia cells in cell culture at concentrations of 5 μM or less, by sensitizing the tumor cells to lipid peroxidation, the process where free radicals react with electrons from cell membrane lipids, resulting in cell damage.
α-Parinaric acid is similarly cytotoxic to malignant gliomas grown in cell culture.
Normal (non-tumorous) astrocytes grown in culture are far less sensitive to the cytotoxic effects of α-parinaric acid.
This preferential toxicity towards tumor cells is due to a differential regulation of c-Jun N-terminal kinase, and forkhead transcription factors between malignant and normal cells.
α-Parinaric acid is a conjugated polyunsaturated fatty acid.
Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds.
The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH2−).
Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.
Natural sources:
α-Parinaric acid occurs naturally in the seeds of the makita tree (Parinari laurina), a tree found in Fiji and other Pacific islands.
Makita seeds contain about 46% α-parinaric acid, 34% α-eleostearic acid as major components, with lesser amounts of saturated fatty acids, oleic acid and linoleic acid.
α-Parinaric acid is also found in the seed oil of Impatiens balsamina, a member of the family Balsaminaceae.
The major fatty acids of Impatiens balsamina are 4.7% palmitic acid, 5.8% stearic acid, 2.8% arachidic acid, 18.3% oleic acid, 9.2% linoleic acid, 30.1% linolenic acid and 29.1% α-parinaric acid.
It is also present in the fungus Clavulina cristata, and the plant Sebastiana brasiliensis (family Euphorbiaceae).
Biosynthesis:
The biochemical mechanism by which α-parinaric acid is formed in the plant Impatiens balsamina was elaborated using techniques of molecular biology.
The enzyme responsible for the creation of the conjugated double bonds was identified using expressed sequence tags, and called a "conjugase".
This enzyme is related to the family of fatty acid desaturase enzymes responsible for putting double bonds into fatty acids.
Chemical Synthesis:
α-Parinaric acid may be synthesized chemically using α-linoleic acid as a starting compound.
This synthesis enables the transformation of 1,4,7-octatriene methylene-interrupted cis double bonds of naturally occurring polyunsaturated fatty acids to 1,3,5,7-octatetraenes in high yield.
More recently (2008), Lee et al. reported a simple and efficient chemical synthesis using a modular design method called iterative cross-coupling.
Membrane Probes:
Both the alpha and beta (all trans) isomers of parinaric acid are used as molecular probes of lipid-lipid interactions, by monitoring phase transitions in bilayer lipid membranes.
α-Parinaric acid was shown to integrate normally into the phospholipid bilayer of mammalian cells, nervous tissue, with minimal effects on the biophysical properties of the membrane.
Molecular interactions with neighboring membrane lipids will affect the fluorescence of α-parinaric acid in predictable ways, and the subsequent subtle changes in energy intensities may be measured spectroscopically.
Researchers have put α-parinaric to good use in the study of membrane biophysics.
For example, it was used to help establish the existence of a "fluidity gradient" across the membrane bilayer of some tumor cells ― the inner monolayer of the membrane is less fluid than the outer monolayer.
Lipid-protein Interactions:
α-Parinaric acid is also used as a chromophore to study interactions between membrane proteins and lipids.
Because of the similarity of α-parinaric acid to normal membrane lipids, it has minimal perturbing influence.
By measuring shifts in the absorption spectrum, enhancement of α-parinaric acid fluorescence, induced circular dichroism, and energy transfer between tryptophan amino acids in the protein and the bound chromophore, information may be gleaned about the molecular interactions between protein and lipid.
For example, this technique is used to investigate how fatty acids bind to serum albumin (a highly abundant blood protein), lipid transport processes including structural characterization of lipoproteins, and phospholipid-transfer proteins.
Product Description
cis-Parinaric acid is a naturally occurring polyunsaturated fatty acid containing an unusual conjugated (Z,E,E,Z) tetraene.
This chromophore provides for a natural fluorescence at 432 nm with an excitation wavelength at 320 nm.
a-Parinaric acid occurs naturally in the seeds of the Makita tree, a tropical rainforest tree indigenous to Fiji. Makita seeds are inedible, and this toxicity may be due at least in part to the unstable conjugated fatty acids, including cis-parinaric acid, contained within the seed.
a-Parinaric acid has been used for the measurement of phospholipase activity, lipase activity, and as an indicator of lipid peroxidation.
A simple and reliable method for synthesizing four isomers of parinaric acid from α-linolenic acid (ALA) in high yields is described.
The methylene-interrupted, cis triene system (1,4,7-octatriene) of ALA and common to other naturally occurring polyunsaturated fatty acids was transformed to a conjugated tetraene system (1,3,5,7-octatetraene).
The synthesis involves bromination of ALA using 0.l M Br2 in a saturated solution of NaBr in methanol, esterification of the fatty acid dibromides, double dehydrobromination by 1,8-diazabicyclo[5.4.0]undec-7-ene and saponification of the conjugated esters to a mixture of free conjugated acids.
Addition of one molecule of bromine to the 12,13-double bond of ALA and subsequent dehydrobromination produces α-parinaric acid (9Z,11E,13E,15Z-octadecatetraenoic acid); addition of Br2 to the 9,10-double bond or 15,16-double bond and then dehydrobromination and rearrangement yields 9E,11E,13E,15Z-octadecatetraenoic or 9E,11E,13E,15Z-octadecatetraenoic acids, respectively.
The mixture of parinaric acid isomers is obtained in 65% yield, and the isomers can be purified by preparative HPLC; alternatively, the isomers can be converted by base catalyzed cis–trans isomerization.
cis-Parinaric acid is a naturally occurring polyunsaturated fatty acid containing an unusual conjugated (Z,E,E,Z) tetraene.
This chromophore provides for a natural fluorescence at 432 nm with an excitation wavelength at 320 nm. cis-Parinaric acid occurs naturally in the seeds of the Makita tree, a tropical rainforest tree indigenous to Fiji.
Makita seeds are inedible, and this toxicity may be due at least in part to the unstable conjugated fatty acids, including cis-parinaric acid, contained within the seed.
cis-Parinaric acid has been used for the measurement of phospholipase activity, lipase activity, and as an indicator of lipid peroxidation.
parinaric acid, also known as 18:4 (N-3) or parinarate, belongs to the class of organic compounds known as lineolic acids and derivatives.
These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
Based on a literature review a small amount of articles have been published on parinaric acid.
This compound has been identified in human blood as reported by (PMID: 31557052 ).
Cis-parinaric acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives.
Technically cis-Parinaric acid is part of the human exposome.
The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health.
An individual's exposure begins before birth and includes insults from environmental and occupational sources.
