Design and Synthesis of Structure-Simplified Derivatives of Gonytolide for the Promotion of Innate Immune Responses

Haruhisa Kikuchi; Tsuyoshi Hoshikawa; Shoichiro Kurata; Yasuhiro Katou; Yoshiteru Oshima

doi:10.1021/acs.jnatprod.5b00829

Design and Synthesis of Structure-Simplified Derivatives of Gonytolide for the Promotion of Innate Immune Responses

Haruhisa Kikuchi, Tsuyoshi Hoshikawa, Shoichiro Kurata, Yasuhiro Katou, Yoshiteru Oshima

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

15 Citations (Scopus)

Abstract

Gonytolide A (1), a dimeric chromanone substituted with the-lactone, shows promoting activity of innate immune responses. However, biological studies on this compound have been limited by the low amounts of 1 available from natural resources and the difficulty of its synthesis. In this study, we designed and synthesized structure-simplified gonytolide derivatives. Bischromone 10 and biflavone 13 both promoted the mammalian TNF-α signaling pathway and Drosophila innate immunity. They did not contain a chiral center and were easy to synthesize. Hence, they can be used as lead compounds for a new type of immunostimulating drugs and as research reagents.

Original language	English
Pages (from-to)	1259-1266
Number of pages	8
Journal	Journal of Natural Products
Volume	79
Issue number	5
DOIs	https://doi.org/10.1021/acs.jnatprod.5b00829
Publication status	Published - 2016 May 27
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.5b00829

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abstract = "Gonytolide A (1), a dimeric chromanone substituted with the-lactone, shows promoting activity of innate immune responses. However, biological studies on this compound have been limited by the low amounts of 1 available from natural resources and the difficulty of its synthesis. In this study, we designed and synthesized structure-simplified gonytolide derivatives. Bischromone 10 and biflavone 13 both promoted the mammalian TNF-α signaling pathway and Drosophila innate immunity. They did not contain a chiral center and were easy to synthesize. Hence, they can be used as lead compounds for a new type of immunostimulating drugs and as research reagents.",

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AU - Kikuchi, Haruhisa

AU - Hoshikawa, Tsuyoshi

AU - Kurata, Shoichiro

AU - Katou, Yasuhiro

AU - Oshima, Yoshiteru

PY - 2016/5/27

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AB - Gonytolide A (1), a dimeric chromanone substituted with the-lactone, shows promoting activity of innate immune responses. However, biological studies on this compound have been limited by the low amounts of 1 available from natural resources and the difficulty of its synthesis. In this study, we designed and synthesized structure-simplified gonytolide derivatives. Bischromone 10 and biflavone 13 both promoted the mammalian TNF-α signaling pathway and Drosophila innate immunity. They did not contain a chiral center and were easy to synthesize. Hence, they can be used as lead compounds for a new type of immunostimulating drugs and as research reagents.

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Design and Synthesis of Structure-Simplified Derivatives of Gonytolide for the Promotion of Innate Immune Responses

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