Isolation of Δ9 Heptadecenoic Acid from Lamb Caul Fat

Shorland, F. B.; Jessop, A. S.

doi:10.1038/176737a0

Cited by 24 publications

(6 citation statements)

References 5 publications

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“…The previous knowledge about the physiological roles of heptadecenoic acid is very limited. Heptadecenoic acid has been recognized as a minor constituent of ruminant fats and used as a potential marker of microbial biomass [23, 24]. It was assumed that the rumen microbial originated odd chain fatty acids are exported to milk fat after intestinal absorption.…”

Section: Discussionmentioning

confidence: 99%

C. Elegans Fatty Acid Two-Hydroxylase Regulates Intestinal Homeostasis by Affecting Heptadecenoic Acid Production

Wang

Huang

et al. 2018

Cell Physiol Biochem

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Background/Aims: The hydroxylation of fatty acids at the C-2 position is the first step of fatty acid α-oxidation and generates sphingolipids containing 2-hydroxy fatty acyl moieties. Fatty acid 2-hydroxylation is catalyzed by Fatty acid 2-hydroxylase (FA2H) enzyme. However, the precise roles of FA2H and fatty acid 2-hydroxylation in whole cell homeostasis still remain unclear. Methods: Here we utilize Caenorhabditis elegans as the model and systemically investigate the physiological functions of FATH-1/C25A1.5, the highly conserved worm homolog for mammalian FA2H enzyme. Immunostaining, dye-staining and translational fusion reporters were used to visualize FATH-1 protein and a variety of subcellular structures. The “click chemistry” method was employed to label 2-OH fatty acid in vivo. Global and tissue-specific RNAi knockdown experiments were performed to inactivate FATH-1 function. Lipid analysis of the fath-1 deficient mutants was achieved by mass spectrometry. Results: C. elegans FATH-1 is expressed at most developmental stages and in most tissues. Loss of fath-1 expression results in severe growth retardation and shortened lifespan. FATH-1 function is crucially required in the intestine but not the epidermis with stereospecificity. The “click chemistry” labeling technique showed that the FATH-1 metabolites are mainly enriched in membrane structures preferable to the apical side of the intestinal cells. At the subcellular level, we found that loss of fath-1 expression inhibits lipid droplets formation, as well as selectively disrupts peroxisomes and apical endosomes. Lipid analysis of the fath-1 deficient animals revealed a significant reduction in the content of heptadecenoic acid, while other major FAs remain unaffected. Feeding of exogenous heptadecenoic acid (C17: 1), but not oleic acid (C18: 1), rescues the global and subcellular defects of fath-1 knockdown worms. Conclusion: Our study revealed that FATH-1 and its catalytic products are highly specific in the context of chirality, C-chain length, spatial distribution, as well as the types of cellular organelles they affect. Such an unexpected degree of specificity for the synthesis and functions of hydroxylated FAs helps to regulate protein transport and fat metabolism, therefore maintaining the cellular homeostasis of the intestinal cells. These findings may help our understanding of FA2H functions across species, and offer potential therapeutical targets for treating FA2H-related diseases.

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Section: Discussionmentioning

confidence: 99%

C. Elegans Fatty Acid Two-Hydroxylase Regulates Intestinal Homeostasis by Affecting Heptadecenoic Acid Production

Wang

Huang

et al. 2018

Cell Physiol Biochem

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“…Although odd-numbered unsaturated normal fatty acids have not formerly been isolated from butterfat, a straight-chain C17 mono-unsaturated fatty acid (n-heptadecenoic acid) has been found in human-hair fat (Weitkamp, Smiljanic & Rothman, 1947), lamb-caul fat (Shorland & Jessop, 1955), musk-ox body fat (Chisholn & Hopkins, 1957) show that the trace amounts of C17 unsaturated acids present inhuman-hair fat yieldedn-undecanoic and n-nonanoic acids on oxidation with potassium permanganate in acetone and comprised a mixture of 80 % of A" and 20 % of A8 isomers of n-heptadecenoic acid.…”

Section: Discussionmentioning

confidence: 99%

The isolation of cis-Δ9-heptadecenoic acid from butterfat

Hansen¹,

Shorland²,

Cooke³

1960

Biochemical Journal

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Butterfat contains a wide range of fatty acids extending from C2 to C26 (cf. Hilditch, 1956;Jack & Smith, 1956;. Although the better-known constituents are the evennumbered saturated homologues from C4 to C18, and the even-numbered mono-unsaturated acids from C10 to C22, it has been established in recent years that trace quantities of saturated branched-chain acids, saturated normal odd-numbered acids and saturated high-molecular-weight (C20 to C26) components are also present. In addition, there is evidence for the occurrence in butterfat of C18 conjugated and unconjugated diand poly-unsaturated acids, and C20 and C22 diand poly-unsaturated non-conjugated acids (cf. Hilditch, 1956;Riemenschneider, 1957), as well as trans C01 and C18 acids (Bertram, 1928;Cornwell, Backderf, Wilson & Brown, 1953;Backderf & Brown, 1958).In the present paper is reported the isolation from butterfat of an odd-numbered mono-unsaturated fatty acid: ci8-A9-heptadecenoic acid. Oddnumbered unsaturated fatty acids have not formerly been isolated from butterfat.

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“…Feeding palmitic acid could affect fat fatty acid composition, for instance feeding highly concentrated sources of palmitic acid to dairy cows increases significantly C16:0 in milk fat (De Souza and Lock, 2019; Ghasemi et al., 2020;., Loften et al., 2014). Therefore, also considering the extent of the decrease observed, soybean GMB151 does not represent a concern in animal nutrition. ˗The monounsaturated heptadecenoic acid is a minor constituent of ruminant fats (Shorland and Jessop, 1955); along with other odd‐chain fatty acids, is assumed to be mainly of rumen microbial origin and, after intestinal absorption, is deposited in tissues or exported to milk fat (Alves et al., 2006; Pfeuffer and Jaudszus, 2016). Considering that no toxicological concerns related to heptadecenoic acid are known, the very low concentration of this fatty acid in soybean GMB151, and the magnitude of the increase, no nutritional concern is identified.…”

Section: Assessmentmentioning

confidence: 99%

Assessment of genetically modified soybean GMB151 for food and feed uses, under Regulation (EC) No 1829/2003 (application EFSA‐GMO‐NL‐2018‐153)

Naegeli¹,

Bresson²,

Dalmay³

et al. 2021

EFS2

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Soybean GMB 151 was developed to confer tolerance to 4‐hydroxyphenylpyruvate dioxygenase ( HPPD ) inhibitor herbicides and resistance to nematodes. The molecular characterisation data and bioinformatic analyses do not identify issues requiring food/feed safety assessment. None of the identified differences in the agronomic/phenotypic and compositional characteristics tested between soybean GMB 151 and its conventional counterpart needs further assessment, except for palmitic acid and heptadecenoic acid in seeds and carbohydrate and crude protein in forage, which does not raise nutritional and safety concerns. The GMO Panel does not identify safety concerns regarding the toxicity and allergenicity of the HPPD ‐4 and Cry14Ab‐1 proteins as expressed in soybean GMB 151, and finds no evidence that the genetic modification would change the overall allergenicity of soybean GMB 151. In the context of this application, the consumption of food and feed from soybean GMB 151 does not represent a nutritional concern in humans and animals. The GMO Panel concludes that soybean GMB 151 is as safe as the conventional counterpart and non‐ GM soybean reference varieties tested, and no post‐market monitoring of food/feed is considered necessary. In the case of accidental release of viable soybean GMB 151 seeds into the environment, this would not raise environmental safety concerns. The post‐market environmental monitoring plan and reporting intervals are in line with the intended uses of soybean GMB 151. The GMO Panel concludes that soybean GMB 151 is as safe as its conventional counterpart and the tested non‐ GM soybean reference varieties with respect to potential effects on human and animal health and the environment.

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Isolation of Δ9 Heptadecenoic Acid from Lamb Caul Fat

Cited by 24 publications

References 5 publications

C. Elegans Fatty Acid Two-Hydroxylase Regulates Intestinal Homeostasis by Affecting Heptadecenoic Acid Production

C. Elegans Fatty Acid Two-Hydroxylase Regulates Intestinal Homeostasis by Affecting Heptadecenoic Acid Production

The isolation of cis-Δ9-heptadecenoic acid from butterfat

Assessment of genetically modified soybean GMB151 for food and feed uses, under Regulation (EC) No 1829/2003 (application EFSA‐GMO‐NL‐2018‐153)

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