Enzymatic remodeling of fatty acid molecules by SCDase demonstrated that fucosyl GM1a possessing a polyunsaturated fatty acid induces apoptosis in HL60 human promyelocyte leukemia cells

Xu Xu, Hatsumi M. Goda, Masanori Inagaki, Nozomu Okino, Makoto Ito

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Glycosphingolipids show heterogeneity in carbohydrate as well as lipid (ceramide) moieties. However, the biological relevance of the heterogeneity of ceramide has yet to be elucidated. To assess the significance of fatty acid molecules of glycosphingolipids, enzymatic remodeling of fatty acyl chains of glycosphingolipids was performed using sphingolipid ceramide N-deacylase which catalyzes a reversible reaction in which the N-acyl linkage of ceramide is cleaved or synthesized. Using the hydrolysis and condensation reactions of the enzyme, fucosyl GM1a having a single but different fatty acid molecule were synthesized. We found that fucosyl GM1a having polyunsaturated fatty acids (PUFA-Fuc-GM1a) inhibited the proliferation of human leukemia-derived HL60 cells, whereas parental fucosyl GM1a did not. PUFA-Fuc-GM1a, but not lyso-Fuc-GM1a which lacks fatty acid molecules, was found to induce apoptosis in HL60 cells. This study clearly shows that the fatty acid moiety of glycosphingolipids could significantly affect their pharmacological activities.

Original languageEnglish
Pages (from-to)433-437
Number of pages5
JournalJournal of the Faculty of Agriculture, Kyushu University
Volume54
Issue number2
Publication statusPublished - Oct 1 2009

Fingerprint

glycosphingolipids
Granulocyte Precursor Cells
Glycosphingolipids
ceramides
leukemia
Unsaturated Fatty Acids
polyunsaturated fatty acids
Ceramides
Leukemia
Fatty Acids
apoptosis
Apoptosis
fatty acids
HL-60 Cells
cells
sphingolipids
Hydrolysis
hydrolysis
Carbohydrates
Pharmacology

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Agronomy and Crop Science

Cite this

@article{85e4745bd397464a887b8e3fe92d3360,
title = "Enzymatic remodeling of fatty acid molecules by SCDase demonstrated that fucosyl GM1a possessing a polyunsaturated fatty acid induces apoptosis in HL60 human promyelocyte leukemia cells",
abstract = "Glycosphingolipids show heterogeneity in carbohydrate as well as lipid (ceramide) moieties. However, the biological relevance of the heterogeneity of ceramide has yet to be elucidated. To assess the significance of fatty acid molecules of glycosphingolipids, enzymatic remodeling of fatty acyl chains of glycosphingolipids was performed using sphingolipid ceramide N-deacylase which catalyzes a reversible reaction in which the N-acyl linkage of ceramide is cleaved or synthesized. Using the hydrolysis and condensation reactions of the enzyme, fucosyl GM1a having a single but different fatty acid molecule were synthesized. We found that fucosyl GM1a having polyunsaturated fatty acids (PUFA-Fuc-GM1a) inhibited the proliferation of human leukemia-derived HL60 cells, whereas parental fucosyl GM1a did not. PUFA-Fuc-GM1a, but not lyso-Fuc-GM1a which lacks fatty acid molecules, was found to induce apoptosis in HL60 cells. This study clearly shows that the fatty acid moiety of glycosphingolipids could significantly affect their pharmacological activities.",
author = "Xu Xu and Goda, {Hatsumi M.} and Masanori Inagaki and Nozomu Okino and Makoto Ito",
year = "2009",
month = "10",
day = "1",
language = "English",
volume = "54",
pages = "433--437",
journal = "Journal of the Faculty of Agriculture, Kyushu University",
issn = "0023-6152",
publisher = "Faculty of Agriculture, Kyushu University",
number = "2",

}

TY - JOUR

T1 - Enzymatic remodeling of fatty acid molecules by SCDase demonstrated that fucosyl GM1a possessing a polyunsaturated fatty acid induces apoptosis in HL60 human promyelocyte leukemia cells

AU - Xu, Xu

AU - Goda, Hatsumi M.

AU - Inagaki, Masanori

AU - Okino, Nozomu

AU - Ito, Makoto

PY - 2009/10/1

Y1 - 2009/10/1

N2 - Glycosphingolipids show heterogeneity in carbohydrate as well as lipid (ceramide) moieties. However, the biological relevance of the heterogeneity of ceramide has yet to be elucidated. To assess the significance of fatty acid molecules of glycosphingolipids, enzymatic remodeling of fatty acyl chains of glycosphingolipids was performed using sphingolipid ceramide N-deacylase which catalyzes a reversible reaction in which the N-acyl linkage of ceramide is cleaved or synthesized. Using the hydrolysis and condensation reactions of the enzyme, fucosyl GM1a having a single but different fatty acid molecule were synthesized. We found that fucosyl GM1a having polyunsaturated fatty acids (PUFA-Fuc-GM1a) inhibited the proliferation of human leukemia-derived HL60 cells, whereas parental fucosyl GM1a did not. PUFA-Fuc-GM1a, but not lyso-Fuc-GM1a which lacks fatty acid molecules, was found to induce apoptosis in HL60 cells. This study clearly shows that the fatty acid moiety of glycosphingolipids could significantly affect their pharmacological activities.

AB - Glycosphingolipids show heterogeneity in carbohydrate as well as lipid (ceramide) moieties. However, the biological relevance of the heterogeneity of ceramide has yet to be elucidated. To assess the significance of fatty acid molecules of glycosphingolipids, enzymatic remodeling of fatty acyl chains of glycosphingolipids was performed using sphingolipid ceramide N-deacylase which catalyzes a reversible reaction in which the N-acyl linkage of ceramide is cleaved or synthesized. Using the hydrolysis and condensation reactions of the enzyme, fucosyl GM1a having a single but different fatty acid molecule were synthesized. We found that fucosyl GM1a having polyunsaturated fatty acids (PUFA-Fuc-GM1a) inhibited the proliferation of human leukemia-derived HL60 cells, whereas parental fucosyl GM1a did not. PUFA-Fuc-GM1a, but not lyso-Fuc-GM1a which lacks fatty acid molecules, was found to induce apoptosis in HL60 cells. This study clearly shows that the fatty acid moiety of glycosphingolipids could significantly affect their pharmacological activities.

UR - http://www.scopus.com/inward/record.url?scp=70450171949&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70450171949&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:70450171949

VL - 54

SP - 433

EP - 437

JO - Journal of the Faculty of Agriculture, Kyushu University

JF - Journal of the Faculty of Agriculture, Kyushu University

SN - 0023-6152

IS - 2

ER -