The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

Haruhisa Kikuchi; Jun Komiya; Yoshinori Saito; Jun Ichi Sekiya; Shigeyoshi Honma; Norimichi Nakahata; Yoshiteru Oshima

doi:10.1016/S0040-4039(02)00038-2

The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

Haruhisa Kikuchi, Jun Komiya, Yoshinori Saito, Jun Ichi Sekiya, Shigeyoshi Honma, Norimichi Nakahata, Yoshiteru Oshima

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

17 Citations (Scopus)

Abstract

To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract of their fruit bodies, two novel acylated amino sugars were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-acetyl-D-glucosamine. Biological evaluation of 1 and 2 showed they induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

Original language	English
Pages (from-to)	1477-1480
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(02)00038-2
Publication status	Published - 2002 Feb 18
Externally published	Yes

Keywords

Amino sugars
Cellular slime molds
Differentiation
PC-12 cell

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)00038-2

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title = "The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity",

abstract = "To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract of their fruit bodies, two novel acylated amino sugars were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-acetyl-D-glucosamine. Biological evaluation of 1 and 2 showed they induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.",

keywords = "Amino sugars, Cellular slime molds, Differentiation, PC-12 cell",

author = "Haruhisa Kikuchi and Jun Komiya and Yoshinori Saito and Sekiya, {Jun Ichi} and Shigeyoshi Honma and Norimichi Nakahata and Yoshiteru Oshima",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (No. 12470474) from the Ministry of Education, Science, Sports, and Culture of Japan.",

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doi = "10.1016/S0040-4039(02)00038-2",

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T1 - The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

AU - Kikuchi, Haruhisa

AU - Komiya, Jun

AU - Saito, Yoshinori

AU - Sekiya, Jun Ichi

AU - Honma, Shigeyoshi

AU - Nakahata, Norimichi

AU - Oshima, Yoshiteru

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (No. 12470474) from the Ministry of Education, Science, Sports, and Culture of Japan.

PY - 2002/2/18

Y1 - 2002/2/18

N2 - To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract of their fruit bodies, two novel acylated amino sugars were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-acetyl-D-glucosamine. Biological evaluation of 1 and 2 showed they induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

AB - To clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and explore any biologically active substances which they may hold, constituents of two species were investigated. From a methanol extract of their fruit bodies, two novel acylated amino sugars were isolated, dictyoglucosamine A (1) from D. purpureum and dictyoglucosamine B (2) from D. discoideum. For further analysis, these compounds were then synthesized from N-acetyl-D-glucosamine. Biological evaluation of 1 and 2 showed they induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

KW - Amino sugars

KW - Cellular slime molds

KW - Differentiation

KW - PC-12 cell

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The isolation and synthesis of two novel N-acetyl glucosamine derivatives from Dictyostelium cellular slime molds which exhibit neurite outgrowth activity

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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