Novel odd-chain cyclopropane fatty acids: detection in a mammalian lipidome and uptake by hepatosplanchnic tissues

被引：0

作者：

Sobhi, Hany F. ^{[1
]}

Mercer, Kelly E. ^{[2
,3
,8
]}

Lan, Renny S. ^{[2
,3
]}

Yeruva, Laxmi ^{[2
,3
,4
]}

Ten Have, Gabriella A. M. ^{[5
]}

Deutz, Nicolaas E. P. ^{[5
]}

Piccolo, Brian D. ^{[2
,3
]}

Debedat, Jean ^{[6
,7
]}

Pack, Lindsay M. ^{[3
]}

Adams, Sean H. ^{[6
,7
]}

机构：

[1] Coppin State Univ, Ctr Organ Synth, Dept Nat Sci, Baltimore, MD 21216 USA

[2] Univ Arkansas Med Sci, Dept Pediat, Little Rock, AR USA

[3] Arkansas Childrens Nutr Ctr, Little Rock, AR USA

[4] USDA ARS Southeast Area, Arkansas Childrens Nutr Ctr, Microbiome & Metab Res Unit, Little Rock, AR USA

[5] Texas A&M Univ, Ctr Translat Res Aging & Longev, Dept Hlth & Kinesiol, College Stn, TX USA

[6] Univ Calif Davis, Sch Med, Dept Surg, Sacramento, CA 95616 USA

[7] Univ Calif Davis, Sch Med, Ctr Alimentary & Metab Sci, Sacramento, CA 95616 USA

[8] US FDA, Natl Ctr Toxicol Res, Div Syst Biol, Jefferson, AR 72079 USA

来源：

JOURNAL OF LIPID RESEARCH | 2024年 / 65卷 / 10期

关键词：

xenometabolite; xenometabolism; microbial metabolism; microbiome; microbiota; URINARY METABOLITES; HEXANEDIOIC ACID; CHEMICAL NATURE; GUT MICROBIOME; IDENTIFICATION; LIVER; OXIDATION; ACYLCARNITINE; PURIFICATION; INVOLVEMENT;

D O I：

10.1016/j.jlr.2024.100632

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Microbe-produced molecules (xenometabolites) found in foods or produced by gut microbiota are increasingly implicated in microbe- microbe and microbe-host communication. Xenolipids, in particular, are a class of metabolites for which the full catalog remains to be elaborated in mammalian systems. We and others have observed that cis-3,4-methylene-heptanoylcarnitine is a lipid derivative that is one of the most abundant medium- chain acylcarnitines in human blood, hypothesized to be a product of incomplete beta-oxidation of one or more "odd-chain" long-chain cyclopropane fatty acids (CpFAs). We deduced two possible candidates, cis11,12-methylene-pentadecanoic acid (cis-11,12-MPD) and cis-13,14-methylene-heptadecanoic acid (cis-13,14MHD). Authentic standards were synthesized: cis-11pentadecenoic acid and cis-13-heptadecenoic acid were generated (using Jones reagent) from cis-11pentadecene-1-ol and cis-13-heptadecene-1-ol, respectively, and these were converted to CpFAs via a reaction involving diiodomethane. Using these standards in mass spectrometry analyses, we determined the presence/absence of cis-11,12-MPD and cis-13,14MHD in archived piglet biospecimens. Both CpFAs were detected in rectal contents of sow and soy-fed piglets. Archived mass spectra were analyzed post hoc from a second independent study that used tissue-specific catheterization to monitor net metabolite flux in growing pigs. This confirmed the presence of both CpFAs in plasma and revealed a significant net uptake of the odd-chain CpFAs across the splanchnic tissue bed and liver. The results confirm that the novel xenolipids cis-11,12-MPD and cis-13,14-MHD can be components of the mammalian lipidome and are viable candidate precursors of cis 3,4-methylene-heptanoylcarnitine produced from partial beta-oxidation in liver or other tissues.

引用

页数：9