Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

H. Kikuchi; Y. Saito; J. Komiya; Y. Takaya; S. Honma; N. Nakahata; A. Ito; Y. Oshima

doi:10.1021/jo015657x

Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

H. Kikuchi, Y. Saito, J. Komiya, Y. Takaya, S. Honma, N. Nakahata, A. Ito, Y. Oshima

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

62 Citations (Scopus)

Abstract

We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

Original language	English
Pages (from-to)	6982-6987
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	66
Issue number	21
DOIs	https://doi.org/10.1021/jo015657x
Publication status	Published - 2001 Oct 19
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo015657x

Cite this

@article{da0916adcdaf481ebf0f64e89ea4ea7c,

title = "Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity",

abstract = "We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.",

author = "H. Kikuchi and Y. Saito and J. Komiya and Y. Takaya and S. Honma and N. Nakahata and A. Ito and Y. Oshima",

year = "2001",

month = oct,

day = "19",

doi = "10.1021/jo015657x",

language = "English",

volume = "66",

pages = "6982--6987",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Furanodictine A and B

T2 - Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

AU - Kikuchi, H.

AU - Saito, Y.

AU - Komiya, J.

AU - Takaya, Y.

AU - Honma, S.

AU - Nakahata, N.

AU - Ito, A.

AU - Oshima, Y.

PY - 2001/10/19

Y1 - 2001/10/19

N2 - We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

AB - We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

UR - http://www.scopus.com/inward/record.url?scp=0035914080&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035914080&partnerID=8YFLogxK

U2 - 10.1021/jo015657x

DO - 10.1021/jo015657x

M3 - Article

C2 - 11597217

AN - SCOPUS:0035914080

SN - 0022-3263

VL - 66

SP - 6982

EP - 6987

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this