Mapping the structure-activity relationship of <em>β</em>-sitosteryl fatty acid esters in condensing phospholipid monolayers

doi:10.1007/s11705-015-1502-x

Front. Chem. Sci. Eng.

2015, Vol. 9

Issue (1) : 105-113 https://doi.org/10.1007/s11705-015-1502-x

RESEARCH ARTICLE

Mapping the structure-activity relationship of β-sitosteryl fatty acid esters in condensing phospholipid monolayers

Worawan PANPIPAT¹,Hasene KESKIN^1,²,Zheng GUO^1,^*(

)

1. Department of Engineering, Faculty of Science, Aarhus University, Gustav Wieds Vej 10, 8000 Aarhus C, Denmark
2. Department of Food Engineering, Faculty of Engineering, University of Gaziantep, 27310 Gaziantep, Turkey

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Abstract

The phase behavior of twelve synthesized β-sitosteryl fatty acid esters with acyl moieties with different chain lengths (C2:0-C18:0) and different degrees of unsaturation (C18:1-C18:3) were investigated in pure and mixed Langmuir monolayers with phospholipids. The surface-pressure isotherms showed that short chain β-sitosteryl fatty acid esters gave smaller mean molecular areas and had decreased monolayer stability and the long chain steryl esters did not produce collapsed plateaus. All the steryl esters displayed strong condensing effects, but there was a pronounced structural dependency: medium chain esters (C8 and C10) were less efficient than short and long chain esters. Atomic force microscopy imaging demonstrated that monolayers mixed with dipalmitoyl phosphatidylcholine (DPPC) displayed both DPPC-rich and steryl lipid-rich domains. However, the height and area differences between the two phases and the roughness and morphologic patterns were very dependent on the steryl lipid concentrations as well as the length, the degree of unsaturation and the molecular conformations of the acyl segments. These findings not only provide a better understanding of the interactions between phytosteryl hydrophobic derivatives and biomembranes, but also may be of general use for the design and engineering of phytosterol structural derivations for specific food and pharmaceutical applications.

Keywords β-sitosteryl fatty acid esters dipalmitoyl phosphatidylcholine Langmuir monolayer condensing effect structure-activity relationship

Corresponding Author(s): Zheng GUO

Online First Date: 05 March 2015 Issue Date: 07 April 2015

Cite this article:

Worawan PANPIPAT,Hasene KESKIN,Zheng GUO. Mapping the structure-activity relationship of β-sitosteryl fatty acid esters in condensing phospholipid monolayers[J]. Front. Chem. Sci. Eng., 2015, 9(1): 105-113.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-015-1502-x
https://academic.hep.com.cn/fcse/EN/Y2015/V9/I1/105

Fig.1 Scheme 1 The molecular structures of cholesterol, β-sitosterol and the β-sitosteryl fatty acid esters used in this study

Fig.2 The surface pressure-area isotherms of pure DPPC, cholestrol, β-sitosterol and β-sitosteryl fatty acid esters monolayers at the air/water interface

Tab.1 Area at collapse (?²) of DPPC-sterol/steryl lipid monolayers

Fig.3 Excess free energy of mixing (ΔG^exc) vs. composition (X, molar fraction of steryl lipid) for mixed monolayers of DPPC/sterol with different fatty acyl carbon chain lengths (a) and different degrees of unsaturation (b) in β-sitosterol

Fig.4 Condensation effects (%) vs. composition (X, molar fraction of steryl lipid) for mixed monolayers of DPPC/sterol with different fatty acyl carbon chain lengths (a) and different degree of unsaturation (b) in β-sitosterol

Fig.5 AFM images of DPPC, cholesterol, β-sitosterol, selected β-sitosteryl fatty acid esters and mixed DPPC-steryl lipid with 0.1 and 0.3 mole fractions of steryl lipid

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