epi-Neozaline, a chemotaxonomic marker for Penicillium tulipae

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Type Article
Original languageEnglish
Pages (from-to)345-348
Number of pages4
JournalBiochemical Systematics and Ecology
Volume34
Issue number4
DOI
Publication statusPublished - Apr 2006
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Abstract

Reported here is the structural confirmation of the metabolites meleagrin (1) and the new metabolite, epi-neoxaline (2) obtained from the Penicillium tulipae Overy & Frisvad type strain (IBT 3458; IBT culture collection, BioCentrum-DTU). P. tulipae belongs to the Penicillium ser. Corymbifera; therefore, to establish the chemotaxonomic significance of epi-neoxaline (2), metabolite production of 10 strains of each Corymbifera taxa were compared: P. albocoremium (Frisvad) Frisvad (IBT: 3457, 3891, 10672, 10673, 10683, 10688, 13001, 21071, 21502, 22521), P. allii Vincent & Pitt (IBT: 3772, 4112, 5460, 5553, 5555, 11735, 13030, 14490, 20212, 21503), P. hirsutum Dierckx (IBT: 3061, 3096, 10623, 10624, 10702 12398, 13033, 18398, 19340, 21531), P. hordei Stolk (IBT: 3083, 3084, 3097, 4154, 4900, 11204, 11478, 12904, 21532, 23024), P. radicicola Overy & Frisvad (IBT: 3489, 3491, 10629, 10693, 10695, 10696, 11646, 12914, 18894, 22526), P. tulipae Overy & Frisvad (IBT: 3458, 10632, 10674, 10676, 10677, 10678, 10676, 10681, 10684, 10686) and P. venetum (Frisvad) Frisvad (IBT: 3053, 10655, 16215, 16308, 21549, 22111, 23039, 23040, 23814, 24614). During the recent description of P. tulipae, a distinguishing metabolite produced by all of the 26 strains surveyed was suggested as being similar to neoxaline (Overy and Frisvad, 2003 D.P. Overy and J.C. Frisvad, Syst. Appl. Microbiol. 26 (2003), p. 631. Abstract | PDF (488 K) | Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (14)Overy and Frisvad, 2003). This metabolite was easily visualized by TLC following CeSO4 spray application. Further studies investigating the in vitro and in planta production of roquefortine/oxaline biosynthesis pathway metabolites demonstrated that meleagrin (1) accumulated in the mycelia of P. tulipae, while 2 was excreted into the surrounding environment (Overy et al., 2005c). This lead to the conclusion that 2 is the endproduct of the roquefortine/epi-neoxaline biogenesis pathway in P. tulipae.

Keywords

  • Penicillium tulipae, epi-Neoxaline, Meleagrin, Chemotaxonomy, Secondary metabolite profiling