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Precursor-directed biosynthesis of phenylbenzoisoquinolindione alkaloids and the discovery of a phenylphenalenone-based plant defense mechanism

MPG-Autoren
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Chen,  Yu
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Paetz,  Christian
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Schneider,  Bernd
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Zitation

Chen, Y., Paetz, C., & Schneider, B. (2018). Precursor-directed biosynthesis of phenylbenzoisoquinolindione alkaloids and the discovery of a phenylphenalenone-based plant defense mechanism. Journal of Natural Products, 81(4), 879-884. doi:10.1021/acs.jnatprod.7b00885.


Zitierlink: http://hdl.handle.net/21.11116/0000-0000-C1BA-4
Zusammenfassung
Phenylbenzoisochromenone glucosides (oxa-phenylphenalenone glucosides) occurring in some phenylphenalenone-producing plants of the Haemodoraceae undergo conversion to phenylbenzoisoquinolindiones (aza-phenylphenalenones) in extracts of Xiphidium caeruleum. Precursordirected biosynthetic experiments were used to generate a series of new phenylbenzoisoquinolindiones from native phenylbenzoisochromenone glucosides and external amines, amino acids, and peptides. Intermediates of the conversion were isolated, incubated with cell-free extracts, and exposed to reactions under oxidative or inert conditions, respectively, to elucidate the entire pathway from phenylbenzoisochromenones to phenylbenzoisoquinolindiones. An intermediate in this pathway, a reactive hydroxylactone/aldehyde, readily binds not only to amines in vitro but may also bind to the N-terminus of biogenic peptides and proteins of herbivores and pathogens in vivo. The deactivation of biogenic amino compounds by N-terminal modification is discussed as the key reaction of a novel phenylphenalenone-based plant defense mechanism. According to these data, the ecological function of phenylphenalenone-type compounds in the Haemodoraceae, subfamily Haemodoroideae, has been substantiated.