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

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.

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NMR251s1.pdf (Supplementary material), 13MB
 
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 Creators:
Chen, Yu1, Author           
Paetz, Christian1, Author           
Schneider, Bernd1, Author           
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1Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              

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 Abstract: 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.

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 Dates: 2018-032018-03-062018-04-27
 Publication Status: Published in print
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 Identifiers: Other: NMR251
DOI: 10.1021/acs.jnatprod.7b00885
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Title: Journal of Natural Products
  Other : J. Nat. Prod.
Source Genre: Journal
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Publ. Info: Cincinnati, Ohio : American Society of Pharmacognosy.
Pages: - Volume / Issue: 81 (4) Sequence Number: - Start / End Page: 879 - 884 Identifier: ISSN: 0163-3864
CoNE: https://pure.mpg.de/cone/journals/resource/954927550329