Synthesis of Kalasinamide, a Putative Plant Defense Phototoxin

Michael Gandy, Matthew Piggott

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported C-13 NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.
Original languageEnglish
Pages (from-to)866-868
JournalJournal of Natural Products
Volume71
Issue number5
DOIs
Publication statusPublished - 2008

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Anthraquinones
Singlet Oxygen
Photooxidation
Poisons
Biosynthesis
Pathogens
Biological Products
Freezing
Melting point
Nuclear magnetic resonance
kalasinamide
benzoquinone
marcanine A

Cite this

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abstract = "The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported C-13 NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.",
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Synthesis of Kalasinamide, a Putative Plant Defense Phototoxin. / Gandy, Michael; Piggott, Matthew.

In: Journal of Natural Products, Vol. 71, No. 5, 2008, p. 866-868.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of Kalasinamide, a Putative Plant Defense Phototoxin

AU - Gandy, Michael

AU - Piggott, Matthew

PY - 2008

Y1 - 2008

N2 - The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported C-13 NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.

AB - The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported C-13 NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.

U2 - 10.1021/np070582z

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EP - 868

JO - Journal of Natural Products

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