Synthesis

Gunstone, Frank D.; Harwood, John L.; Krog, N.

doi:10.1007/978-1-4899-2905-1_7

Cited by 7 publications

(8 citation statements)

References 122 publications

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“…Helium was used as a carrier gas at 1.2 mL per min and the oven temperature was maintained isothermally at 140 °C. cis-C18:1 isomers (∆8,9,11) were synthesized as described before17, processed to fatty acid methyl esters, and used for validation of the separation of cis-C18:1 isomers and confirmation of the retention times of respective cis-C18:1 fatty acid methyl esters. Evidence for separation of cis-8-C18:1 and cis-9-C18:1 is presented in Extended Data Figure 8b.…”

Section: Methodsmentioning

confidence: 99%

Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity

Vriens

Christen

Parik

et al. 2019

Nature

369

326

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Most tumors have an aberrantly activated lipid metabolism 1 , 2 , which enables them to synthesize, elongate and desaturate fatty acids to support proliferation. However, only particular subsets of cancer cells are sensitive toward approaches targeting fatty acid metabolism, and in particular fatty acid desaturation 3 . This suggests that many cancer cells harbor an unexplored plasticity in their fatty acid metabolism. Here, we discover that some cancer cells can exploit an alternative fatty acid desaturation pathway. We identify various cancer cell lines, murine hepatocellular carcinomas (HCC), and primary human liver and lung carcinomas that desaturate palmitate to the unusual fatty acid sapienate to support membrane biosynthesis during proliferation. Accordingly, we found that sapienate biosynthesis enables cancer cells to bypass the known stearoyl-CoA desaturase (SCD)-dependent fatty acid desaturation. Thus, only by targeting both desaturation pathways the in vitro and in vivo proliferation of sapienate synthesizing cancer cells is impaired. Our discovery explains metabolic plasticity in fatty acid desaturation and constitutes an unexplored metabolic rewiring in cancers.

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Section: Methodsmentioning

confidence: 99%

Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity

Vriens

Christen

Parik

et al. 2019

Nature

369

326

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“…in the oil of the nuts of the tung oil tree. [7] Tung oil is used as a drying oil for a number of products including varnishes, resins, inks, paints and coatings. Because of its excellent properties there are attempts to increase the production of tung oil in the United States and to introduce new uses of the oil in consumer products.…”

Section: Introductionmentioning

confidence: 99%

“…Because of its excellent properties there are attempts to increase the production of tung oil in the United States and to introduce new uses of the oil in consumer products. [8] Punicic acid (9,13-cis,11-trans-octadecatrienoic acid) (3) is the main fatty acid of the seed oil of pomegranate [7] (Figure 1). (1), α-eleostearic acid (9-cis,11,13-trans-octadecatrienoic acid) (2) and punicic acid (9,13-cis,11-trans-octadecatrienoic acid) (3).…”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Stereoselective Diels–Alder Additions of Maleic Anhydride to Conjugated Triene Fatty Acid Methyl Esters

et al. 2007

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Keywords: Diels-Alder reaction / Cyclization / Methyl calendulate / Methyl α-eleostearate / Maleic anhydride / Renewable feedstockThe thermal, solvent-free addition of maleic anhydride to methyl calendulate (methyl 8,10-trans,12-cis-octadecatrienoate) (1a) occurs with very high regio-and stereoselectivity at C-8 and C-11 of the fatty compound giving the endo-DielsAlder adduct 4 with retention of the cis-configured double bond. Analogously, the Diels-Alder addition of maleic anhydride to methyl α-eleostearate (methyl 9-cis,11,13-trans-octadecatrienoate) (2a) takes place regio-and stereoselectively

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“…Phenolic compounds and acids were the dominating ones in all of the studied samples due to their high ionization efficiencies. A range of fatty acids (i.e., palmitic, stearic, caprylic, pelargonic, and myristic acid) showed the highest abundance . In contrast, glucose was the most abundant compound observed in G6 (as the deprotonated molecule, [C 6 H 11 O 6 ] − , and the chloride adduct, [C 6 H 12 O 6 Cl] − ).…”

Section: Resultsmentioning

confidence: 99%

Analysis of Volatile and Nonvolatile Constituents in Gin by Direct-Infusion Ultrahigh-Resolution ESI/APPI FT-ICR Mass Spectrometry

Dou

Mäkinen

Jänis

2023

J. Agric. Food Chem.

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Gin is one of the most consumed distilled alcoholic spirits worldwide, with more than 400 million liters sold every year. It is most often produced through redistillation of agricultural ethanol in the presence of botanicals, most notably juniper berries, which give gin its characteristic flavor. Due to its natural ingredients, gin is a complex mixture of hundreds of volatile and nonvolatile chemical constituents. In this work, ultrahigh-resolution Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry was used for the compositional analysis of 16 commercially produced gins. Two complementary ionization methods, namely, electrospray ionization (ESI) and atmospheric-pressure photoionization (APPI), were employed to cover a wider compositional space. Each gin provided unique chemical fingerprints by ESI and APPI, which allowed semiquantitative analysis of 135 tentatively identified compounds, including terpene hydrocarbons, terpenoids, phenolics, fatty acids, aldehydes, and esters. Most of these compounds have not been previously reported in gins. While chemical fingerprints were rather similar between most products, some products contained unique compounds due to their special natural ingredients or the production methods applied. For instance, a barrel-matured gin contained a high content of syringaldehyde and sinapaldehyde, which are typical phenolic aldehydes originated from oak wood. In addition, the relative abundance of vanillin, vanillic acid, gallic acid, coniferyl aldehyde, and syringaldehyde was clearly higher than in the other gin samples. Ultrahigh-resolution FT-ICR MS serves as a powerful tool for direct chemical fingerprinting of gin or any other distilled spirit, which can be used for rapid product quality screening, product optimization, or possible counterfeit product discovery.

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Synthesis

Cited by 7 publications

References 122 publications

Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity

Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity

Regio‐ and Stereoselective Diels–Alder Additions of Maleic Anhydride to Conjugated Triene Fatty Acid Methyl Esters

Analysis of Volatile and Nonvolatile Constituents in Gin by Direct-Infusion Ultrahigh-Resolution ESI/APPI FT-ICR Mass Spectrometry

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