Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil<sup>1a</sup>

Smith, Craig R.; Wilson, T. L.; Bates, Robert B.; Scholfield, C. R.

doi:10.1021/jo01056a031

Cited by 35 publications

(5 citation statements)

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“…6). Densipolic acid, OH 12 18:2 9,15 , identified earlier in Physaria densipila oil [22] was not detected in Physaria fendleri oil ( [9] and the current study).…”

Section: Resultscontrasting

confidence: 47%

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Lin

Chen

2013

J Americ Oil Chem Soc

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Castor oil has many industrial uses because of its high content (90 %) of the hydroxy fatty acid, ricinoleic acid (OH1218:19). Lesquerella oil containing lesquerolic acid (Ls, OH1420:111) is potentially useful in industry. Ten molecular species of diacylglycerols and 74 molecular species of triacylglycerols in lesquerella (Physaria fendleri) oil were identified by electrospray ionization mass spectrometry as lithium adducts of acylglycerols in the HPLC fractions of lesquerella oil. Among them were: LsLsO, LsLsLn, LsLsL, LsLn–OH20:2, LsO–OH20:2 and LsL–OH20:2. The structures of the four new hydroxy fatty acid constituents of acylglycerols were proposed by the MS of the lithium adducts of fatty acids as (comparing to those in castor oil): OH1218:29,14 (OH1218:29,13 in castor oil), OH1218:39,14,16 (OH18:3 not detected in castor oil), diOH12,1318:29,14 (diOH11,1218:29,13 in castor oil) and diOH13,1420:111 (diOH20:1 not detected in castor oil, diOH11,1218:19 in castor oil). Trihydroxy fatty acids were not detected in lesquerella oil. The differences in the structures of these C18 hydroxy fatty acids between lesquerella and castor oils indicated that the polyhydroxy fatty acids were biosynthesized and were not the result of autoxidation products.

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“…6). Densipolic acid, OH 12 18:2 9,15 , identified earlier in Physaria densipila oil [22] was not detected in Physaria fendleri oil ( [9] and the current study).…”

Section: Resultscontrasting

confidence: 47%

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Lin

Chen

2013

J Americ Oil Chem Soc

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“…This OH18:2 in castor oil is different from densipolic acid (12hydroxyoctadeca-9,15-dienoic acid, Fig. 1C) in Lesquerella densipila seed oil [13]. The MS spectrum of densipolic acid is as not detected because the second double bond at C-15 of densipolic acid is not adjacent to the hydroxyl group at C-12.…”

Section: Resultsmentioning

confidence: 88%

Identification of Minor Acylglycerols Less Polar than Triricinolein in Castor Oil by Mass Spectrometry

Lin

Chen

2012

J Americ Oil Chem Soc

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Acylglycerols in castor oil less polar than triricinolein were identified by electrospray ionization-mass spectrometry using the lithium adducts of the acylglycerols in the HPLC fractions of castor oil. Thirty four new molecular species of acylglycerols containing hydroxy fatty acids in castor oil were identified by MS. The chain lengths of fatty acid substituents were C16, C18, C20, C22 and C23. The numbers of double bonds of the fatty acids were from zero to three. The numbers of hydroxyl groups on the fatty acid chains were from zero to three as previously reported. The structure of fatty acid, OH18:2, was proposed as 12-hydroxy-9,13-octadecadienoic acid. An unusual odd-numbered long-chain fatty acid, 23:0 (tricosanoic acid), was identified. Some new estolides and tetraacylglycerols, were identified as (12-ricinoleoylricinoleoyl)-ricinoleoyl-linoleoyl-glycerol (RRRL), (12-ricinoleoylricinoleoyl)-ricinoleoyl-oleoyl-glycerol (RRRO), (12-ricinoleoylricinoleoyl)-ricinoleoyl-palmitoyl-glycerol (RRRP), (12-ricinoleoylricinoleoyl)-ricinoleoyl-stearoylglycerol (RRRS) and (12-ricinoleoylricinoleoyl)-ricinoleoyl-linolenoyl-glycerol (RRRLn). The normal fatty acid (non-hydroxylated) of these tetraacylglycerols were directly attached to the glycerol backbone. The biosynthetic pathway of castor oil is proposed.

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“…We only mention a few examples that occur in dietary sources. The most important seem to be the previously mentioned 2-hydroxylinolenic acid and two hydroxy acids occurring in plants of the genus Lesquerella— densipolic and auricolic acid [ 130 , 163 , 164 , 165 , 166 ]. One of them, densipolic acid, was found in Linum usitatissimum [ 132 ].…”

Section: Sources Of Omega-3 Fatty Acidsmentioning

confidence: 99%

A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty Acids

2018

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Omega-3 fatty acids, one of the key building blocks of cell membranes, have been of particular interest to scientists for many years. However, only a small group of the most important omega-3 polyunsaturated fatty acids are considered. This full-length review presents a broad and relatively complete cross-section of knowledge about omega-3 monounsaturated fatty acids, polyunsaturates, and an outline of their modifications. This is important because all these subgroups undoubtedly play an important role in the function of organisms. Some monounsaturated omega-3s are pheromone precursors in insects. Polyunsaturates with a very long chain are commonly found in the central nervous system and mammalian testes, in sponge organisms, and are also immunomodulating agents. Numerous modifications of omega-3 acids are plant hormones. Their chemical structure, chemical binding (in triacylglycerols, phospholipids, and ethyl esters) and bioavailability have been widely discussed indicating a correlation between the last two. Particular attention is paid to the effective methods of supplementation, and a detailed list of sources of omega-3 acids is presented, with meticulous reference to the generally available food. Both the oral and parenteral routes of administration are taken into account, and the omega-3 transport through the blood-brain barrier is mentioned. Having different eating habits in mind, the interactions between food fatty acids intake are discussed. Omega-3 acids are very susceptible to oxidation, and storage conditions often lead to a dramatic increase in this exposure. Therefore, the effect of oxidation on their bioavailability is briefly outlined.

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Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil^1a

Cited by 35 publications

References 1 publication

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Identification of Minor Acylglycerols Less Polar than Triricinolein in Castor Oil by Mass Spectrometry

A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty Acids

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Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil1a

Cited by 35 publications

References 1 publication

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Identification of TAG and DAG and their FA Constituents in Lesquerella (Physaria fendleri) Oil by HPLC and MS

Identification of Minor Acylglycerols Less Polar than Triricinolein in Castor Oil by Mass Spectrometry

A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty Acids

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Product

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Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil^1a