Synthesis of (6Z,9Z,11E)-octadecatrienoic and (8Z,11Z,13E)-eicosatrienoic acids and their [1-14C]-radiolabeled analogs

Gnädig, Silke; Berdeaux, Olivier; Loreau, Olivier; Noël, Jean‐Pierre; Sébédio, Jean‐Louis

doi:10.1016/s0009-3084(01)00170-0

Cited by 9 publications

(5 citation statements)

References 35 publications

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“…The radio-GC and GC-FID results obtained after injection on a BPX-70 column (Fig. 2B) confirmed that the 6c,9c,11t-18:3 was elongated into its corresponding conjugated 20:3, as evidenced by comparing the retention time with that of the 8c,11c,13t-20:3 standard obtained by total synthesis (17). Moreover, 23:0 and 24:0 (lignoceric acid) were added to the conjugated 20:3 metabolite formed from 6c,9c,11t-18:3 in liver microsomes and to 8c,11c,13t-20:3 standard to calculate the ECL by GC on a polar column (CP-Sil, 60-190°C) as carried out for the ∆6-desaturation study.…”

Section: Resultssupporting

confidence: 67%

“…of unlabeled and labeled methyl octadecatrienoate, respectively. The conjugated 18:3 metabolite formed from 9c,11t-18:2 in liver microsomes was identified as 6c,9c,11t-18:3 by GC on a polar column (BPX-70) by comparison with a standard obtained by total synthesis with an isomeric purity >95% (17). Moreover, 19:0 and 22:0 (behenic acid) were added to the conjugated 18:3 metabolite formed from 9c,11t-18:2 in liver microsomes and to the synthetic 6c,9c,11t-18:3 standard for calculation of the ECL by GC on a polar column (CP-Sil, 60-190°C).…”

Section: Resultsmentioning

confidence: 99%

“…To investigate further the hypothetical metabolic pathway of rumenic acid into conjugated PUFA, an in vitro elongation study was carried out using radiolabeled 6c,9c,11t-18:3 obtained by total stereoselective synthesis (17). The elongation of 6c,9c,11t-18:3 was compared to that of γ-linolenic acid as its nonconjugated homolog.…”

Section: Resultsmentioning

confidence: 99%

“…[1-14 C]6c,9c,11t-18:3, [1-14 C]-8c,11c,13t-20:3, and their unlabeled homologs were obtained by total synthesis (17). Coenzymes and chemicals were supplied by Sigma Chemicals.…”

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confidence: 99%

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In vitro desaturation and elongation of rumenic acid by rat liver microsomes

Berdeaux

Gnädig

Chardigny

et al. 2002

Lipids

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Various nutritional studies on CLA, a mixture of isomers of linoleic acid, have reported the occurrence of conjugated long-chain PUFA after feeding experimental animals with rumenic acid, 9c,11t-18:2, the major CLA isomer, probably as a result of successive desaturation and chain elongation. In the present work, in vitro studies were carried out to obtain information on the conversion of rumenic acid. Experiments were first focused on the in vitro delta6-desaturation of rumenic acid, the regulatory step in the biosynthesis of long-chain n-6 PUFA. The conversion of rumenic acid was compared to that of linoleic acid (9c,12c-18:2). Isolated rat liver microsomes were incubated with radiolabeled 9c,12c-18:2 and 9c,11t-18:2 under desaturation conditions. The data indicated that [1-(14)C]9c,11t-18:2 was a poorer substrate for delta6-desaturase than [1-(14)C]9c,12c-18:2. Next, in vitro elongation of 6c,9c,11t-18:3 and 6c,9c,12c-18:3 (gamma-linolenic acid) was investigated in rat liver microsomes. Under elongation conditions, [1-(14)C]6c,9c,11t-18:3 was 1.5-fold better converted into [3-(14)C]8c,11c,13t-20:3 than [1-(14)C]6c,9c,12c-18:3 into [3-(14)C]8c,11c,14c-20:3. Finally, in vitro delta5-desaturation of 8c,11c,13t-20:3 compared to 8c,11c,14c-20:3 was investigated. The conversion level of [1-(14)C]8c,11c,13t-20:3 into [1-(14)C]5c,8c,11c,13t-20:4 was 10 times lower than that of [1-(14)C]8c,11c,14c-20:3 into [1-(14)C]5c,8c,11c,14c-20:4 at low substrate concentrations and 4 times lower at the saturating substrate level, suggesting that conjugated 20:3 is a poor substrate for the delta5-desaturase.

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Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…[1-14 C]6c,9c,11t-18:3, [1-14 C]-8c,11c,13t-20:3, and their unlabeled homologs were obtained by total synthesis (17). Coenzymes and chemicals were supplied by Sigma Chemicals.…”

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confidence: 99%

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In vitro desaturation and elongation of rumenic acid by rat liver microsomes

Berdeaux

Gnädig

Chardigny

et al. 2002

Lipids

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“…One OH group of this diol was protected as THP-acetal, and the other was converted to the I substituent using a known method with 1H-imidazole, Ph 3 P, and I 2 CHEMISTRY & BIODIVERSITY -Vol. 6 (2009) 1390 [14]. Treatment of 1-iodo-4-[(tetrahydropyran-2-yl)oxy]butane (4) with Ph 3 P in MeCN yielded the phosphonium salt 5 which was coupled with (Z)-dec-4-enal using sodium hexamethyldisilazide (NaHMDS) as a base to generate the phosphonium ylide.…”

mentioning

confidence: 99%

Syntheses, Characterizations, and Biological Activities of Tetradeca‐4,8‐dien‐1‐yl Acetates as Sex Attractants of Leaf‐Mining Moth of the Genus Phyllonorycter (Lepidoptera: Gracillariidae)

Liblikas

Mozūraitis

Santangelo

et al. 2009

Chemistry & Biodiversity

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The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.

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Phosphorus Ylides and Related Compounds

2019

Organophosphorus Chemistry

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Synthesis of (6Z,9Z,11E)-octadecatrienoic and (8Z,11Z,13E)-eicosatrienoic acids and their [1-14C]-radiolabeled analogs

Cited by 9 publications

References 35 publications

In vitro desaturation and elongation of rumenic acid by rat liver microsomes

In vitro desaturation and elongation of rumenic acid by rat liver microsomes

Syntheses, Characterizations, and Biological Activities of Tetradeca‐4,8‐dien‐1‐yl Acetates as Sex Attractants of Leaf‐Mining Moth of the Genus Phyllonorycter (Lepidoptera: Gracillariidae)

Phosphorus Ylides and Related Compounds

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