Possible Role of Bent Structure of Methylated Lithocholic Acid on Artificial and Plasma Membranes

Tomoyuki Iwasaki, Nobuyuki Endo, Yuta Nakayama, Toshiyuki Kamei, Toshinori Shimanouchi, Hidemi Nakamura, Keita Hayashi

Research output: Contribution to journalArticlepeer-review


Bile acids form micelles that are essential for the absorption of dietary lipids. However, excessive bile acid micelles can disrupt the plasma membrane by removing phospholipids, resulting in cell death. We hypothesized that the bent geometrical structure of the steroid scaffold of bile acids decreases the lipid order (similar to unsaturated phospholipids with cis double bonds), disrupting the plasma membrane. Here, lithocholic acid (LCA), a bile acid, was methylated to prevent micellization. Methylated lithocholic acid (Me-LCA) was mixed with a thin phase-separated lipid bilayer comprising 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and cholesterol (Chol). Me-LCA was not localized in the DPPC-rich rigid phase but localized in the DOPC-rich fluid phase, and excess Me-LCA did not affect the phase separation. Me-LCA is distributed in the plasma and organelle membranes. However, Me-LCA with bent structure did not affect the membrane properties, membrane fluidity, and hydrophobicity of liposomes composed of DOPC, DPPC, and Chol and also did not affect the proliferation of cells.

Original languageEnglish
Article number997
Issue number10
Publication statusPublished - Oct 2022


  • lipid membrane
  • membrane property
  • steroid molecule

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Process Chemistry and Technology
  • Filtration and Separation


Dive into the research topics of 'Possible Role of Bent Structure of Methylated Lithocholic Acid on Artificial and Plasma Membranes'. Together they form a unique fingerprint.

Cite this