Diversity in the fatty-acid conformation and chain packing of cis-unsaturated lipids

Kaneko, Fumitoshi; Yano, Junko; Sato, Kiyotaka

doi:10.1016/s0959-440x(98)80117-6

Cited by 56 publications

(51 citation statements)

References 39 publications

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“…Detailed conformational analyses of mono-and poly-cisunsaturated chains indicate that torsion angles of saturated C-C bonds next to the double bond have broad distributions around the skew, skewЈ, and trans conformations, with a low probability of conformations between gauche Ϫ and gauche ϩ (10,32,41). On the other hand, molecular mechanics calculations indicated that the gauche probability for the second next torsions to the double bond is higher than that in a fully saturated chain (39)(40)(41).…”

Section: Discussionmentioning

confidence: 99%

“…Experimental (10)(11)(12)(13) and molecular modeling (14) studies of model membranes show that in the membrane, a double bond in the cis conformation located near the middle of the chain interferes with the hydrocarbon chain packing. This decreases the cooperativity of the chain interactions and causes a substantial decline in the main phase transition temperature (13,(15)(16)(17)(18).…”

mentioning

confidence: 99%

“…Scarce experimental (10,39) and molecular modeling (40-42) studies of mixed-chain phospholipids indicate that in mono-cis -unsaturated chains, torsion angles of the single bonds next to the double bond are highly distributed around skew (120 Њ ), skew Ј (240 Њ ), and trans (180 Њ ) conformations. The estimated distribution of angles ranges from 90 to 175 Њ and Ϫ 90 to Ϫ 175 Њ for the skew and skew Ј conformations (10).…”

mentioning

confidence: 99%

“…The estimated distribution of angles ranges from 90 to 175 Њ and Ϫ 90 to Ϫ 175 Њ for the skew and skew Ј conformations (10). This follows from the steric energy profile (41), which has two broad minima centered at Ϯ 110 Њ , a relatively narrow and low-energy barrier centered at 180 Њ , and a broad, higher energy barrier extending from Ϫ 60 Њ ( gauche Ϫ ) to 60 Њ ( gauche ϩ ) with a small maximum at 0 Њ .…”

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confidence: 99%

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Effects of phospholipid unsaturation on the bilayer nonpolar region

Róg

Murzyn

Gurbiel

et al. 2004

Journal of Lipid Research

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Molecular dynamics simulations of two monounsaturated phosphatidylcholine (PC) bilayers made of 1-palmitoyl-2-oleoyl-PC (POPC; cis -unsaturated) and 1-palmitoyl-2-elaidoyl-PC (PEPC; trans -unsaturated) were carried out to investigate the effect of a double bond in the PC ␤ -chain and its conformation on the bilayer core. Four nanosecond trajectories were used for analyses. A fully saturated 1,2-dimyristoyl-PC (DMPC) bilayer was used as a reference system. In agreement with experimental data, this study shows that properties of the PEPC bilayer are more similar to those of the DMPC than to the POPC bilayer. The differences between POPC and PEPC bilayers may be attributed to the different ranges of angles covered by the torsion angles ␤ 10 and ␤ 12 of the single bonds next to the double bond in the oleoyl (O) and elaidoyl (E) chains. Broader distributions of ␤ 10 and ␤ 12 in the E chain than in the O chain make the E chain more flexible. In effect, the packing of chains in the PEPC bilayer is similar to that in the DMPC bilayer, whereas that in the POPC bilayer is looser than that in the DMPC bilayer. The effect of the cis -double bond on torsions at the beginning of the O chain ( ␤ 4 and ␤ 5) is similar to that of cholesterol on these torsions in a myristoyl chain. Phospholipids with two asymmetric hydrocarbon chains, of which one is fully saturated in the ␥ position and the other is mono-cis -or poly-cis -unsaturated in the ␤ position, are the most common in nature (1). Among mono-cisunsaturated phosphatidylcholines (PCs), 1-palmitoyl-2-oleoyl-PC (POPC) is the most abundant. In the past, phospholipids with trans -unsaturated hydrocarbon chains were believed to be rare in nature. They were found in photosynthetic membranes of higher plants (2) and algae (3) as well as in some marine bacteria (4). With advances in separation and quantification techniques, new trans -unsaturated lipids have been identified in membranes of prokaryotes (5) and algal chloroplasts (6). In membranes of gram-negative bacteria, the relative proportion of transunsaturated lipids increases under physiologically stressful conditions, such as increased temperature (7), starvation and desiccation (8), and organic solvents (9). The increase of the trans -to-cis ratio results from an enzymatically controlled direct cis -trans isomerization that does not shift the position of the double bond and occurs only at the ␤ position of the glycerol moiety (7). The cis -trans conversion in the bacterial membrane is believed to be a fast and inexpensive mechanism enabling the membrane to maintain constant fluidity (5).Experimental (10-13) and molecular modeling (14) studies of model membranes show that in the membrane, a double bond in the cis conformation located near the middle of the chain interferes with the hydrocarbon chain packing. This decreases the cooperativity of the chain interactions and causes a substantial decline in the main phase transition temperature (13,(15)(16)(17)(18). The effect of a trans double bond on the main phase trans...

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Effects of phospholipid unsaturation on the bilayer nonpolar region

Róg

Murzyn

Gurbiel

et al. 2004

Journal of Lipid Research

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“…For the subjects of (a) and (c), it is recommended to refer to recent reviews/articles and the references therein contributed by Hernqvist [4], Kaneko et al [5], Goto et al [6] concerning the fat crystal structures, and Dickinson and McClements [7], Marangoni and Hartel [8] concerning the fat crystals in dispersed phases. Before going into the details of the solidification problems, a brief look will be taken at the relationships between the structures and functions of the food fats.…”

Section: Introductionmentioning

confidence: 99%

Solidification and phase transformation behaviour of food fats — a review

Sato¹

1999

Fett/Lipid

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Polymorphism in Fats and Oils

Sato

Ueno

2005

Bailey's Industrial Oil and Fat Products

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This chapter reviews the polymorphism of principal triacylglycerols in single and binary mixture states. First, basic concepts of fat polymorphism, namely, thermal stability, subcell structure and chain length structure are explained together with phase equilibria of binary mixture systems. Then, polymorphic behavior of principal triacylglycerols are described. The phase behavior of the mixture systems of the principal TAGs is discussed with an emphasis of the influence of the polymorphism.

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Diversity in the fatty-acid conformation and chain packing of cis-unsaturated lipids

Cited by 56 publications

References 39 publications

Effects of phospholipid unsaturation on the bilayer nonpolar region

Effects of phospholipid unsaturation on the bilayer nonpolar region

Solidification and phase transformation behaviour of food fats — a review

Polymorphism in Fats and Oils

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