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cis-Vaccenic Acid

(Synonyms: 顺-十八碳烯酸) 目录号 : GC41587

An ω-7 fatty acid

cis-Vaccenic Acid Chemical Structure

Cas No.:506-17-2

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产品描述

cis-Vaccenic acid is an ω-7 fatty acid that has been found in mango pulp.[1] It induces differentiation of, and γ-globin synthesis in, K562 and JK-1 cells, as well as isolated sickle cell transgenic mouse bone marrow erythroid progenitor cells (TMbmEPSCs).[2]

Reference:
[1]. Shibahara, A., Yamamoto, K., Nakayama, T., et al. cis-Vaccenic acid in mango pulp lipids. Lipids 21(6), 388-394 (1986).
[2]. Aimola, I.A., Inuwa, H.M., Nok, A.J., et al. Cis-vaccenic acid induces differentiation and up-regulates gamma globin synthesis in K562, JK1 and transgenic mice erythroid progenitor stem cells. Eur. J. Pharmacol. 776, 9-18 (2016).

Chemical Properties

Cas No. 506-17-2 SDF
别名 顺-十八碳烯酸
化学名 11Z-octadecenoic acid
Canonical SMILES OC(CCCCCCCCC/C=C\CCCCCC)=O
分子式 C18H34O2 分子量 282.5
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 500 mg/ml,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml 储存条件 Store at -20°C
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Research Update

Baker's Yeast Deficient in Storage Lipid Synthesis Uses cis-Vaccenic Acid to Reduce Unsaturated Fatty Acid Toxicity

Lipids 2015 Jul;50(7):621-30.PMID:25908426DOI:10.1007/s11745-015-4022-z.

The role of cis-Vaccenic Acid (18:1n-7) in the reduction of unsaturated fatty acids toxicity was investigated in baker's yeast Saccharomyces cerevisiae. The quadruple mutant (QM, dga1Δ lro1Δ are1Δ are2Δ) deficient in enzymes responsible for triacylglycerol and steryl ester synthesis has been previously shown to be highly sensitive to exogenous unsaturated fatty acids. We have found that cis-Vaccenic Acid accumulated during cultivation in the QM cells but not in the corresponding wild type strain. This accumulation was accompanied by a reduction in palmitoleic acid (16:1n-7) content in the QM cells that is consistent with the proposed formation of cis-Vaccenic Acid by elongation of palmitoleic acid. Fatty acid analysis of individual lipid classes from the QM strain revealed that cis-Vaccenic Acid was highly enriched in the free fatty acid pool. Furthermore, production of cis-Vaccenic Acid was arrested if the mechanism of fatty acids release to the medium was activated. We also showed that exogenous cis-Vaccenic Acid did not affect viability of the QM strain at concentrations toxic for palmitoleic or oleic acids. Moreover, addition of cis-Vaccenic Acid to the growth medium provided partial protection against the lipotoxic effects of exogenous oleic acid. Transformation of palmitoleic acid to cis-Vaccenic Acid is thus a rescue mechanism enabling S. cerevisiae cells to survive in the absence of triacylglycerol synthesis as the major mechanism for unsaturated fatty acid detoxification.

Palmitoleic (16:1 cis-9) and cis-vaccenic (18:1 cis-11) acid alter lipogenesis in bovine adipocyte cultures

Lipids 2012 Dec;47(12):1143-53.PMID:23077002DOI:10.1007/s11745-012-3723-9.

Our objectives were to: (1) confirm elongation products of palmitoleic acid (16:1 cis-9) elongation in vitro using stable isotopes and (2) evaluate if exogenous supplementation of palmitoleic acid, elongation products, or both are responsible for decreased desaturation and lipogenesis rates observed with palmitoleic acid supplementation in bovine adipocytes. Stromal vascular cultures were isolated from adipose tissue of two beef carcasses, allowed to reach confluence, held for 2 days, and differentiated with a standard hormone cocktail (day 0). On day 2, secondary differentiation media containing 1 of 4 fatty acid treatments [0 μM fatty acid (control), or 150 μM palmitic (16:0), palmitoleic, or cis-vaccenic (18:1 cis-11)] was added for 4 days. On day 6, cells were incubated with [(13)C] 16:1, [(13)C] 2, or [(13)C] 18:0 to estimate elongation, lipogenic, and desaturation rates using gas chromatography-mass spectrometry. Enrichment of [(13)C] 18:1 cis-11 confirmed 18:1 cis-11 is an elongation product of 16:1. Additionally, [(13)C] label was seen in 20:1 cis-13 and cis-9, cis-11 CLA. Synthesis of [(13)C] 16:0 from [(13)C] 2 was reduced (P < 0.05) in palmitoleic acid and cis-vaccenic acid-treated compared with control cells following 36 h incubation. By 12 h of [(13)C] 18:0 incubation, cells supplemented with palmitoleic acid had reduced (P < 0.05) [(13)C] 18:1 cis-9 compared with all other treatments. Gene expression and fatty acid results support isotopic data for lipogenesis and desaturation. Therefore, palmitoleic acid is actively elongated in vitro and its elongation product, cis-Vaccenic Acid, can also reduce lipogenesis. However, inhibition of desaturation can be directly attributed to palmitoleic acid and not its elongation products, 18:1 cis-11 or 20:1 cis-13.

ELOVL5 Is a Critical and Targetable Fatty Acid Elongase in Prostate Cancer

Cancer Res 2021 Apr 1;81(7):1704-1718.PMID:33547161DOI:10.1158/0008-5472.CAN-20-2511.

The androgen receptor (AR) is the key oncogenic driver of prostate cancer, and despite implementation of novel AR targeting therapies, outcomes for metastatic disease remain dismal. There is an urgent need to better understand androgen-regulated cellular processes to more effectively target the AR dependence of prostate cancer cells through new therapeutic vulnerabilities. Transcriptomic studies have consistently identified lipid metabolism as a hallmark of enhanced AR signaling in prostate cancer, yet the relationship between AR and the lipidome remains undefined. Using mass spectrometry-based lipidomics, this study reveals increased fatty acyl chain length in phospholipids from prostate cancer cells and patient-derived explants as one of the most striking androgen-regulated changes to lipid metabolism. Potent and direct AR-mediated induction of ELOVL fatty acid elongase 5 (ELOVL5), an enzyme that catalyzes fatty acid elongation, was demonstrated in prostate cancer cells, xenografts, and clinical tumors. Assessment of mRNA and protein in large-scale data sets revealed ELOVL5 as the predominant ELOVL expressed and upregulated in prostate cancer compared with nonmalignant prostate. ELOVL5 depletion markedly altered mitochondrial morphology and function, leading to excess generation of reactive oxygen species and resulting in suppression of prostate cancer cell proliferation, 3D growth, and in vivo tumor growth and metastasis. Supplementation with the monounsaturated fatty acid cis-Vaccenic Acid, a direct product of ELOVL5 elongation, reversed the oxidative stress and associated cell proliferation and migration effects of ELOVL5 knockdown. Collectively, these results identify lipid elongation as a protumorigenic metabolic pathway in prostate cancer that is androgen-regulated, critical for metastasis, and targetable via ELOVL5. SIGNIFICANCE: This study identifies phospholipid elongation as a new metabolic target of androgen action that is critical for prostate tumor metastasis.

Plasma cis-Vaccenic Acid and risk of heart failure with antecedent coronary heart disease in male physicians

Clin Nutr 2014 Jun;33(3):478-82.PMID:23880347DOI:10.1016/j.clnu.2013.07.001.

Background & aims: Although an inverse association of red blood cell cis-Vaccenic Acid and risk of myocardial infarction has been reported, it is unclear whether cis-Vaccenic Acid might lower the risk of heart failure (HF) with antecedent coronary heart disease (CHD). We sought to examine the relation of plasma cis-Vaccenic Acid with HF with antecedent CHD. Methods: This nested case-control study was based on 788 incident HF cases (of whom 258 cases had antecedent CHD) and 788 controls. Each control was selected using a risk set sampling technique at the time of the occurrence of the index case and matched on year of birth, age at blood collection, and race. Fatty acids were measured using gas chromatography and incident HF was self-reported on annual questionnaires and validation in a subsample using medical records. Results: In a multivariable conditional logistic regression, the odds ratio (95% confidence interval) for HF with prior CHD were 1.0 (ref), 0.72 (0.33-1.57), 0.28 (0.12-0.67), and 0.23 (0.09-0.58) across consecutive quartiles of cis-Vaccenic Acid (p_trend 0.0004). Each standard deviation of cis-Vaccenic Acid was associated with a 41% lower risk of HF with antecedent CHD (95% CI: 17%-59%) in a multivariable adjusted model. Conclusions: Our data suggest that higher plasma levels of plasma cis-Vaccenic Acid may be associated with a lower risk of HF with antecedent CHD. Confirmation of these results in the general population including women and other ethnic groups is warranted.

On the origin of cis-Vaccenic Acid photodegradation products in the marine environment

Lipids 2003 Oct;38(10):1085-92.PMID:14669974DOI:10.1007/s11745-006-1164-z.

The origin of 11-hydroxyoctadec-trans-12-enoic and 12-hydroxyoctadec-trans-10-enoic acids (photodegradation products of cis-Vaccenic Acid) in the marine environment was investigated. cis-Vaccenic Acid is commonly used as a bacterial biomarker; however, in heterotrophic bacteria the observed rates of cis-Vaccenic Acid photodegradation are negligible. Here, two hypotheses explaining the source of the photoproducts were tested. According to the first hypothesis, the photoproducts originate from aerobic anoxygenic bacteria, i.e., photoheterotrophic organisms using bacteriochlorophyll-containing reaction centers. Alternatively, the photoproducts come from a heterotrophic bacterial community closely associated with senescent phytoplanktonic cells. cis-Vaccenic Acid photodegradation was detected in both experimental setups. However, a detailed comparison of the cis-Vaccenic Acid photodegradation patterns with those observed in particulate matter samples of the DYFAMED station (Mediterranean Sea) suggests that photodegradation of heterotrophic bacteria attached to senescent phytoplanktonic cells constitutes the more likely source of cis-Vaccenic Acid oxidation products detected in situ.