Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

Haruhisa Kikuchi; Yusuke Matsuo; Yasuhiro Katou; Yuzuru Kubohara; Yoshiteru Oshima

doi:10.1016/j.tet.2012.08.041

Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

Haruhisa Kikuchi, Yusuke Matsuo, Yasuhiro Katou, Yuzuru Kubohara, Yoshiteru Oshima

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

30 Citations (Scopus)

Abstract

From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material for biological evaluation. Compound 3 was the first example of nitrogen-containing natural m-terphenyls, and the isolation of novel classes of compounds such as 3 shows that cellular slime molds are promising sources in natural product chemistry. Moreover, dictyoterphenyl A (3) showed cancer cell-selective antiproliferative activity (IC ₅₀ 2.3-8.6 μM).

Original language	English
Pages (from-to)	8884-8889
Number of pages	6
Journal	Tetrahedron
Volume	68
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2012.08.041
Publication status	Published - 2012 Oct 28
Externally published	Yes

Keywords

Antiproliferative activity
Cellular slime molds
Dictyostelium
Structural elucidation
m-Terphenyl

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.tet.2012.08.041

Cite this

@article{5e41f07dc7df422a9a9f8dc18e2ec862,

title = "Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds",

abstract = "From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material for biological evaluation. Compound 3 was the first example of nitrogen-containing natural m-terphenyls, and the isolation of novel classes of compounds such as 3 shows that cellular slime molds are promising sources in natural product chemistry. Moreover, dictyoterphenyl A (3) showed cancer cell-selective antiproliferative activity (IC 50 2.3-8.6 μM).",

keywords = "Antiproliferative activity, Cellular slime molds, Dictyostelium, Structural elucidation, m-Terphenyl",

author = "Haruhisa Kikuchi and Yusuke Matsuo and Yasuhiro Katou and Yuzuru Kubohara and Yoshiteru Oshima",

note = "Funding Information: This work was supported in part by Grant-in-Aid for Scientific Research (No. 23710247 and No. 24590110 ) from the Ministry of Education, Science, Sports and Culture of Japan , and the SUNBOR GRANT from the Suntory Institute for Bioorganic Research . ",

year = "2012",

month = oct,

day = "28",

doi = "10.1016/j.tet.2012.08.041",

language = "English",

volume = "68",

pages = "8884--8889",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "43",

}

TY - JOUR

T1 - Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

AU - Kikuchi, Haruhisa

AU - Matsuo, Yusuke

AU - Katou, Yasuhiro

AU - Kubohara, Yuzuru

AU - Oshima, Yoshiteru

N1 - Funding Information: This work was supported in part by Grant-in-Aid for Scientific Research (No. 23710247 and No. 24590110 ) from the Ministry of Education, Science, Sports and Culture of Japan , and the SUNBOR GRANT from the Suntory Institute for Bioorganic Research .

PY - 2012/10/28

Y1 - 2012/10/28

N2 - From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material for biological evaluation. Compound 3 was the first example of nitrogen-containing natural m-terphenyls, and the isolation of novel classes of compounds such as 3 shows that cellular slime molds are promising sources in natural product chemistry. Moreover, dictyoterphenyl A (3) showed cancer cell-selective antiproliferative activity (IC 50 2.3-8.6 μM).

AB - From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material for biological evaluation. Compound 3 was the first example of nitrogen-containing natural m-terphenyls, and the isolation of novel classes of compounds such as 3 shows that cellular slime molds are promising sources in natural product chemistry. Moreover, dictyoterphenyl A (3) showed cancer cell-selective antiproliferative activity (IC 50 2.3-8.6 μM).

KW - Antiproliferative activity

KW - Cellular slime molds

KW - Dictyostelium

KW - Structural elucidation

KW - m-Terphenyl

UR - http://www.scopus.com/inward/record.url?scp=84866023423&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84866023423&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.08.041

DO - 10.1016/j.tet.2012.08.041

M3 - Article

AN - SCOPUS:84866023423

SN - 0040-4020

VL - 68

SP - 8884

EP - 8889

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this