Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant

Takashi Tokunaga; Noboru Takada; Minoru Ueda

doi:10.1016/j.tetlet.2004.07.094

Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant

Takashi Tokunaga, Noboru Takada, Minoru Ueda

SCI - Chemistry

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

49 Citations (Scopus)

Abstract

Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of 1 reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of 1 are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity.

Original language	English
Pages (from-to)	7115-7119
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.094
Publication status	Published - 2004 Sept 13

Keywords

Antifeedant
Plumbagin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.07.094

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title = "Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant",

abstract = "Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of 1 reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of 1 are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity.",

keywords = "Antifeedant, Plumbagin",

author = "Takashi Tokunaga and Noboru Takada and Minoru Ueda",

note = "Funding Information: This work was supported by the Ministry of Education, Science, Sports and Culture (Japan) Grant-in-Aid for Scientific Research (No. 15681013) and JSPS Grant for TS. This work was also supported by Grant-in-Aid for the 21st Century COE program of Tohoku University from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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AU - Tokunaga, Takashi

AU - Takada, Noboru

AU - Ueda, Minoru

N1 - Funding Information: This work was supported by the Ministry of Education, Science, Sports and Culture (Japan) Grant-in-Aid for Scientific Research (No. 15681013) and JSPS Grant for TS. This work was also supported by Grant-in-Aid for the 21st Century COE program of Tohoku University from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2004/9/13

Y1 - 2004/9/13

N2 - Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of 1 reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of 1 are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity.

AB - Dionaea muscipula Ellis accumulates a large amount of plumbagin (1), which operates as an antifeedant against predators. Content of 1 reached 0.5% weight of the fresh trap lobes. It was found that other carnivorous plants also accumulated similar naphthoquinone-type strong antifeedant. Thus, naphthoquinone analogs are widely used as an antifeedant among the carnivorous plants. By using several analogs of 1, we clarified that both the high volatility and high redox potential of 1 are important for its strong antifeedant activity. It was known that plumbagin stimulates the mitochondrial electron transport system as a result of intercepting electrons. These results suggested that the Droseraceae family possesses a universal defensive mechanism against predators, that is, accumulation of volatile naphthoquinone with high redox potential as defensive substance. Thus, it is estimated that highly volatile naphthoquinone of moderately high redox potential would be used as an antifeedant of weak toxicity.

KW - Antifeedant

KW - Plumbagin

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Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant

Abstract

Keywords

ASJC Scopus subject areas

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