Bosseopentaenoic acid

Last updated
Bosseopentaenoic acid
Bosseopentaenoic acid structure.svg
Names
Preferred IUPAC name
(5Z,8Z,10E,12E,14Z)-Icosa-5,8,10,12,14-pentaenoic acid
Other names
20:5Δ5Z,8Z,10E,12E,14Z
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-13,15-16H,2-5,14,17-19H2,1H3,(H,21,22)/b7-6-,9-8+,11-10+,13-12-,16-15- X mark.svgN
    Key: QQXWWCIEPUFZQL-JMFSJNRSSA-N X mark.svgN
  • InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-13,15-16H,2-5,14,17-19H2,1H3,(H,21,22)/b7-6-,9-8+,11-10+,13-12-,16-15-
    Key: QQXWWCIEPUFZQL-JMFSJNRSBI
  • OC(=O)CCC/C=C\C/C=C\C=C\C=C\C=C/CCCCC
Properties
C20H30O2
Molar mass 302.458 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bosseopentaenoic acid (BPA) is a conjugated polyunsaturated fatty acid. Bosseopentaenoic acid can be extracted from the red coralline algae, Bossiella orbigniana. [1] The first total synthesis of methyl bosseopentaenoate by consecutive palladium-catalyzed reactions was reported in 2011. [2] In 2017, bosseopentaenoic acid was obtained from the ester hydrolysis of methyl bosseopentaenoate in good yield using mild condition and the synthesis of its sulfur-bridged analogue of BPA; thiophene analogue was achieved by Mohamed and Solum [3] In this study, a comparison between the thiophene analogue and BPA with respect to their antioxidant activity was accomplished. It was shown that the rigidified analogue; the thiophene analogue exhibited higher free radical scavenging potential than the bosseopentaenoic acid. The results showed that by lowering the flexibility of the BPA as lead compound by incorporation thiophene ring in its structure, an increased antioxidant activity was observed. This study opens the door to investigate the relationship between the flexibility of other polyunsaturated fatty acids (PUFAs) and enhancement in the biological activity.

Related Research Articles

<span class="mw-page-title-main">Fatty acid</span> Carboxylic acid

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

Omega−3 fatty acids, also called Omega−3 oils, ω−3 fatty acids, Ω-3 Fatty acids or n−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond three atoms away from the terminal methyl group in their chemical structure. They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology. The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). ALA can be found in plants, while DHA and EPA are found in algae and fish. Marine algae and phytoplankton are primary sources of omega−3 fatty acids. DHA and EPA accumulate in fish that eat these algae. Common sources of plant oils containing ALA include walnuts, edible seeds, and flaxseeds as well as hempseed oil, while sources of EPA and DHA include fish and fish oils, and algae oil.

<span class="mw-page-title-main">Lipoic acid</span> Chemical compound

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α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond.

<span class="mw-page-title-main">Thioester</span> Organosulfur compounds of the form R–SC(=O)–R’

In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.

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<span class="mw-page-title-main">Docosahexaenoic acid</span> Chemical compound

Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina. It is given the fatty acid notation 22:6(n-3). It can be synthesized from alpha-linolenic acid or obtained directly from maternal milk, fatty fish, fish oil, or algae oil. The consumption of DHA contributes to numerous physiological benefits, including cognition. As the primary structural component of nerve cells in the brain, the function of DHA is to support neuronal conduction and to allow optimal function of neuronal membrane proteins.

Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

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<span class="mw-page-title-main">Conjugated fatty acid</span>

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<span class="mw-page-title-main">2,4 Dienoyl-CoA reductase</span> Class of enzymes

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References

  1. Burgess, J.R.; De la Rosa, R.I.; Jacobs, R.S.; Butler, A (1991). "A new eicosapentaenoic acid formed from arachidonic acid in the coralline red algae Bossiella orbigniana". Lipids. 26 (2): 1057–1059. doi:10.1007/BF02544012. S2CID   43372222.
  2. Mohamed, Y. M. A.; Hansen, T. V. (2011). "Synthesis of methyl-(5Z,8Z,10E,12E,14Z)-eicosapentaenoate". Tetrahedron Letters. 52 (10): 1057–1059. doi:10.1016/j.tetlet.2010.12.078.
  3. Mohamed, Y. M. A.; Solum, E. J. (2017). "An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent". Arkivoc. 2017 (part v): 10–19. doi: 10.24820/ark.5550190.p010.086 . hdl: 11250/2492670 .