Synthesis of alkyl glycerolipids with various cationic groups linked directly to the glycerol backbone

1999 ◽  
Vol 48 (7) ◽  
pp. 1369-1372 ◽  
Author(s):  
M. A. Maslov ◽  
E. V. Sycheva ◽  
N. G. Morozova ◽  
G. A. Serebrennikova
Keyword(s):  
Glycerol Backbone ◽  
Alkyl Glycerolipids

ChemInform Abstract: Synthesis of Alkyl Glycerolipids with Various Cationic Groups Linked Directly to the Glycerol Backbone.

ChemInform ◽  
2010 ◽  
Vol 31 (4) ◽  
pp. no-no
Author(s):  
M. A. Maslov ◽  
E. V. Sycheva ◽  
N. G. Morozova ◽  
G. A. Serebrennikova
Keyword(s):  
Glycerol Backbone ◽  
Alkyl Glycerolipids

scholarly journals iPLA2β-mediated lipid detoxification controls p53-driven ferroptosis independent of GPX4

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Delin Chen ◽  
Bo Chu ◽  
Xin Yang ◽  
Zhaoqi Liu ◽  
Ying Jin ◽  
...  
Keyword(s):  
Tumor Suppression ◽  
Normal Development ◽  
Oxygen Species ◽  
Glycerol Backbone ◽  
Independent Manner ◽  
Obvious Effect ◽  
Normal Tissues ◽  
Induced Stress ◽  
Promising Therapeutic Target ◽  
Oxidized Fatty Acids

AbstractHere, we identify iPLA2β as a critical regulator for p53-driven ferroptosis upon reactive oxygen species (ROS)-induced stress. The calcium-independent phospholipase iPLA2β is known to cleave acyl tails from the glycerol backbone of lipids and release oxidized fatty acids from phospholipids. We found that iPLA2β-mediated detoxification of peroxidized lipids is sufficient to suppress p53-driven ferroptosis upon ROS-induced stress, even in GPX4-null cells. Moreover, iPLA2β is overexpressed in human cancers; inhibition of endogenous iPLA2β sensitizes tumor cells to p53-driven ferroptosis and promotes p53-dependent tumor suppression in xenograft mouse models. These results demonstrate that iPLA2β acts as a major ferroptosis repressor in a GPX4-independent manner. Notably, unlike GPX4, loss of iPLA2β has no obvious effect on normal development or cell viability in normal tissues but iPLA2β plays an essential role in regulating ferroptosis upon ROS-induced stress. Thus, our study suggests that iPLA2β is a promising therapeutic target for activating ferroptosis-mediated tumor suppression without serious toxicity concerns.

scholarly journals Structure and Interdigitation of Chain-Asymmetric Phosphatidylcholines and Milk Sphingomyelin in the Fluid Phase

Symmetry ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1441
Author(s):  
Moritz P. K. Frewein ◽  
Milka Doktorova ◽  
Frederick A. Heberle ◽  
Haden L. Scott ◽  
Enrico F. Semeraro ◽  
...  
Keyword(s):  
Chain Length ◽  
Hydration Shell ◽  
Fluid Phase ◽  
Hydrocarbon Chain ◽  
Specific Model ◽  
Glycerol Backbone ◽  
Membrane Composition ◽  
Membrane Structures ◽  
Hydrocarbon Chain Length ◽  
Dynamics Simulations

We addressed the frequent occurrence of mixed-chain lipids in biological membranes and their impact on membrane structure by studying several chain-asymmetric phosphatidylcholines and the highly asymmetric milk sphingomyelin. Specifically, we report trans-membrane structures of the corresponding fluid lamellar phases using small-angle X-ray and neutron scattering, which were jointly analyzed in terms of a membrane composition-specific model, including a headgroup hydration shell. Focusing on terminal methyl groups at the bilayer center, we found a linear relation between hydrocarbon chain length mismatch and the methyl-overlap for phosphatidylcholines, and a non-negligible impact of the glycerol backbone-tilting, letting the sn1-chain penetrate deeper into the opposing leaflet by half a CH2 group. That is, penetration-depth differences due to the ester-linked hydrocarbons at the glycerol backbone, previously reported for gel phase structures, also extend to the more relevant physiological fluid phase, but are significantly reduced. Moreover, milk sphingomyelin was found to follow the same linear relationship suggesting a similar tilt of the sphingosine backbone. Complementarily performed molecular dynamics simulations revealed that there is always a part of the lipid tails bending back, even if there is a high interdigitation with the opposing chains. The extent of this back-bending was similar to that in chain symmetric bilayers. For both cases of adaptation to chain length mismatch, chain-asymmetry has a large impact on hydrocarbon chain ordering, inducing disorder in the longer of the two hydrocarbons.

scholarly journals Synthesis and biochemical studies of analogs of platelet-activating factor bearing a methyl group at C2 of the glycerol backbone.

1987 ◽  
Vol 28 (6) ◽  
pp. 733-738
Author(s):  
R Bittman ◽  
N M Witzke ◽  
T C Lee ◽  
M L Blank ◽  
F Snyder
Keyword(s):  
Platelet Activating Factor ◽  
Glycerol Backbone ◽  
Methyl Group ◽  
Biochemical Studies

Synthesis of new carbohydrate-containing cationic alkyl glycerolipids with antitumor activity

2015 ◽  
Vol 64 (7) ◽  
pp. 1648-1654 ◽  
Author(s):  
E. V. Shmendel ◽  
K. A. Perevoshchikova ◽  
D. K. Shishova ◽  
T. S. Kubasova ◽  
L. L. Tyutyunnik ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Alkyl Glycerolipids

Synthesis and anti-tumor-promoting activity of glycoglycerolipid analogues lacking the glycerol backbone

2003 ◽  
Vol 11 (6) ◽  
pp. 909-912 ◽  
Author(s):  
Diego Colombo ◽  
Fiamma Ronchetti ◽  
Antonio Scala ◽  
Lucio Toma ◽  
Harukuni Tokuda ◽  
...  
Keyword(s):  
Glycerol Backbone

Effect of the Alkanoyl Group Position at the Glycerol Backbone on the Monolayer Characteristics Demonstrated by 2-Monopalmitoyl-rac-glycerol

Langmuir ◽  
2017 ◽  
Vol 33 (44) ◽  
pp. 12559-12568 ◽  
Author(s):  
D. Vollhardt ◽  
G. Brezesinski ◽  
R. Rudert ◽  
A. Gonzalez
Keyword(s):  
Glycerol Backbone ◽  
Group Position

scholarly journals Metabolism of Glycerol, Glucose, and Lactate in the Citric Acid Cycle Prior to Incorporation into Hepatic Acylglycerols

2013 ◽  
Vol 288 (20) ◽  
pp. 14488-14496 ◽  
Author(s):  
Eunsook S. Jin ◽  
A. Dean Sherry ◽  
Craig R. Malloy
Keyword(s):  
Citric Acid ◽  
Citric Acid Cycle ◽  
Hepatic Lipogenesis ◽  
Glycerol Backbone ◽  
Substantial Fraction ◽  
Acid Cycle ◽  
Glycerol Moiety ◽  
The Third ◽  
Relative Contribution ◽  
C Nmr

During hepatic lipogenesis, the glycerol backbone of acylglycerols originates from one of three sources: glucose, glycerol, or substrates passing through the citric acid cycle via glyceroneogenesis. The relative contribution of each substrate source to glycerol in rat liver acylglycerols was determined using 13C-enriched substrates and NMR. Animals received a fixed mixture of glucose, glycerol, and lactate; one group received [U-13C6]glucose, another received [U-13C3]glycerol, and the third received [U-13C3]lactate. After 3 h, the livers were harvested to extract fats, and the glycerol moiety from hydrolyzed acylglycerols was analyzed by 13C NMR. In either fed or fasted animals, glucose and glycerol provided the majority of the glycerol backbone carbons, whereas the contribution of lactate was small. In fed animals, glucose contributed >50% of the total newly synthesized glycerol backbone, and 35% of this contribution occurred after glucose had passed through the citric acid cycle. By comparison, the glycerol contribution was ∼40%, and of this, 17% of the exogenous glycerol passed first through the cycle. In fasted animals, exogenous glycerol became the major contributor to acylglycerols. The contribution from exogenous lactate did increase in fasted animals, but its overall contribution remained small. The contributions of glucose and glycerol that had passed through the citric acid cycle first increased in fasted animals from 35 to 71% for glucose and from 17 to 24% for glycerol. Thus, a substantial fraction from both substrate sources passed through the cycle prior to incorporation into the glycerol moiety of acylglycerols in the liver.

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