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C22 Ceramide (d18:1/22:0)

(Synonyms: C22 Ceramide;Cer(d18:1/22:0);Ceramide (d18:1/22:0)) 目录号 : GC43069

A bioactive sphingolipid

C22 Ceramide (d18:1/22:0) Chemical Structure

Cas No.:27888-44-4

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产品描述

C-22 ceramide is an endogenous bioactive sphingolipid. Ceramides are involved in permeabilization of the mitochondrial outer membrane during apoptosis via the intrinsic pathway.[1] C-22 ceramide forms small channels in liposomes, whereas C-16 ceramide forms channels that can grow in size, suggesting that acyl chain length of ceramides is important in mitochondrial-mediated apoptosis. In addition, the mitochondrial-to-cytosolic stress response (MCSR) in C. elegans fed C-22 ceramide decreases following inhibition of Hsp6 (mortalin/Grp75/mtHsp70) using RNAi.[2]

Reference:
[1]. Stiban, J., and Perera, M. Very long chain ceramides interfere with C16-ceramide-induced channel formation: A plausible mechanism for regulating the initiation of intrinsic apoptosis. Biochim. Biophys. Acta 1848(2), 561-567 (2015).
[2]. Kim, H.E., Grant, A.R., Simic, M.S., et al. Lipid biosynthesis coordinates a mitochondrial-to-cytosolic stress response. Cell 166(6), 1539-1552 (2016).

Chemical Properties

Cas No. 27888-44-4 SDF
别名 C22 Ceramide;Cer(d18:1/22:0);Ceramide (d18:1/22:0)
化学名 N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-docosanamide
Canonical SMILES OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
分子式 C40H79NO3 分子量 622.1
溶解度 0.15mg/ml in DMF 储存条件 Store at -20°C
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1 mM 1.6075 mL 8.0373 mL 16.0746 mL
5 mM 0.3215 mL 1.6075 mL 3.2149 mL
10 mM 0.1607 mL 0.8037 mL 1.6075 mL
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Research Update

Plasma levels of ceramides relate to ischemic stroke risk and clinical severity

Brain Res Bull 2020 May;158:122-127.PMID:32165273DOI:10.1016/j.brainresbull.2020.03.009.

Recent studies have suggested that specific plasma ceramides are independently associated with atherosclerosis and cardiovascular diseases, but it is currently unknown whether plasma ceramide levels are associated with ischemic stroke. Here, we examined whether ceramides were associated with both ischemic stroke risk and clinical severity at admission. We measured three previously identified high-risk plasma ceramide molecules [Cer(d18:1/16:0), Cer(d18:1/22:0), and Cer(d18:1/24:0)] in 202 patients with acute ischemic stroke and 202 age and sex matched control cases. Plasma ceramides levels were measured by a targeted liquid chromatography-tandem mass spectrometry assay at baseline. The median age of the 202 stroke patients was 66 (interquartile range [IQR], 58-75) years and 54.0 % were men. Plasma levels of C16:0, C22:0, and C24:0 ceramides in stroke patients were significantly higher than in those control cases (P < 0.001, all). In multivariate logistic regression analysis adjusted for other risk factors, higher levels of C16:0, C22:0, and C24:0 ceramides were associated with higher risk of ischemic stroke (odd ratio [OR] for one IQR increase: 2.15[1.42-2.99]; 2.90[2.13-4.01] and 1.29[1.10-1.69]; respectively). At admission, 103 patients (51.0 %) had a minor stroke (NIHSS < 6). In these patients, plasma levels of C16:0, C22:0, and C24:0 ceramides were lower than that observed in patients with moderate-to-high clinical severity (P < 0.001, all). In multivariate logistic regression analysis adjusted for other risk factors, higher levels of C16:0, C22:0, and C24:0 ceramides were associated with higher risk of moderate-to-high stroke (OR for one IQR increase: 2.96 [2.05-4.22], 3.03 [2.01-4.25] and 1.72 [1.25-3.31], respectively). An elevated plasma levels of ceramides were predictors of both risk and severity at admission in ischemic stroke patients. The underlying mechanisms of these associations remain to be investigated.

Effect of Korean Red Ginseng on Plasma Ceramide Levels in Postmenopausal Women with Hypercholesterolemia: A Pilot Randomized Controlled Trial

Metabolites 2021 Jun 24;11(7):417.PMID:34202864DOI:10.3390/metabo11070417.

Cardiovascular disease (CVD) is a crucial cause of death in postmenopausal women. Plasma ceramide concentrations are correlated with the development of atherosclerosis and are significant predictors of CVD. Here, we conducted a 4-week, double-blinded, placebo-controlled clinical pilot study to investigate the effect of Korean red ginseng (KRG) on serum ceramide concentrations in 68 postmenopausal women with hypercholesterolemia. Patients were randomly assigned to two groups: the experimental group (n = 36) received KRG and the control (n = 32) group received placebo, 2 g each, once daily. Serum ceramides were measured using liquid chromatography-tandem mass spectrometry at baseline and study completion, with changes in serum ceramide levels as the primary end point. We detected significantly greater mean changes in C16 ceramide levels (d18:1/16:0: -6.4 ± 6.3 pmol/mL vs. 14.6 ± 6.8 pmol/mL, respectively, p = 0.040; d18:1/22:0: -20.8 ± 24.4 pmol/mL vs. 71.1 ± 26.2 pmol/mL, respectively, p = 0.020). Additionally, changes in the median C16 (d18:1/16:0) and C22 (d18:1/22:0) ceramide levels were significantly greater in KRG-group subjects with metabolic syndrome than those without. Therefore, we found that KRG decreases the serum levels of several ceramides in postmenopausal women with hypercholesterolemia, suggesting it may be beneficial for preventing CVD in these individuals.