Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

Noriyasu Hada; Yukihiko Shida; Hiroshi Shimamura; Yoshiko Sonoda; Tadashi Kasahara; Mutsumi Sugita; Tadahiro Takeda

doi:10.1016/j.carres.2008.05.001

Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

Noriyasu Hada, Yukihiko Shida, Hiroshi Shimamura, Yoshiko Sonoda, Tadashi Kasahara, Mutsumi Sugita, Tadahiro Takeda

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (1) and PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNFα-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production.

Original language	English
Pages (from-to)	2221-2228
Number of pages	8
Journal	Carbohydrate Research
Volume	343
Issue number	13
DOIs	https://doi.org/10.1016/j.carres.2008.05.001
Publication status	Published - 2008 Sep 8

Keywords

Amphoteric glycosphingolipid
IL-8 production
Pheretima hilgendorfi
Phosphocholine

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2008.05.001

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Hada, N., Shida, Y., Shimamura, H., Sonoda, Y., Kasahara, T., Sugita, M., & Takeda, T. (2008). Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. Carbohydrate Research, 343(13), 2221-2228. https://doi.org/10.1016/j.carres.2008.05.001

Synthetic studies on glycosphingolipids from Protostomia phyla : syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. / Hada, Noriyasu; Shida, Yukihiko; Shimamura, Hiroshi; Sonoda, Yoshiko; Kasahara, Tadashi; Sugita, Mutsumi; Takeda, Tadahiro.

In: Carbohydrate Research, Vol. 343, No. 13, 08.09.2008, p. 2221-2228.

Research output: Contribution to journal › Article › peer-review

Hada, N, Shida, Y, Shimamura, H, Sonoda, Y, Kasahara, T, Sugita, M & Takeda, T 2008, 'Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi', Carbohydrate Research, vol. 343, no. 13, pp. 2221-2228. https://doi.org/10.1016/j.carres.2008.05.001

Hada, Noriyasu ; Shida, Yukihiko ; Shimamura, Hiroshi ; Sonoda, Yoshiko ; Kasahara, Tadashi ; Sugita, Mutsumi ; Takeda, Tadahiro. / Synthetic studies on glycosphingolipids from Protostomia phyla : syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. In: Carbohydrate Research. 2008 ; Vol. 343, No. 13. pp. 2221-2228.

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abstract = "Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (1) and PC(→6)-β-d-Galp-(1→6)-β-d-Galp-(1→6)-β-d-Galp-(1→1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNFα-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production.",

keywords = "Amphoteric glycosphingolipid, IL-8 production, Pheretima hilgendorfi, Phosphocholine",

author = "Noriyasu Hada and Yukihiko Shida and Hiroshi Shimamura and Yoshiko Sonoda and Tadashi Kasahara and Mutsumi Sugita and Tadahiro Takeda",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 19590011) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and Open Research Center project of the MEXT. The authors are grateful to Ms. J. Hada for providing HR-FAB MS data.",

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Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

Abstract

Keywords

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