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. 2008 Sep;71(9):1574-8.
doi: 10.1021/np800292n. Epub 2008 Aug 28.

Detection of VM55599 and preparaherquamide from Aspergillus japonicus and Penicillium fellutanum: biosynthetic implications

Yousong Ding  1 , Sabine Gruschow, Thomas J Greshock, Jennifer M Finefield, David H Sherman, Robert M Williams
Affiliations

Detection of VM55599 and preparaherquamide from Aspergillus japonicus and Penicillium fellutanum: biosynthetic implications

Yousong Ding et al. J Nat Prod. 2008 Sep.

Abstract

The secondary metabolites VM55599 (4) and preparaherquamide (5) have been identified by LC-MS(n) analysis as natural metabolites in cultures of Penicillium fellutanum, whereas preparaherquamide has been identified only in cultures of Aspergillus japonicus. In accord with a previous proposal, the identification of both metabolites, which have a diastereomeric relationship, provides indirect support for a unified biosynthetic scheme.

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Figures

Figure 1
Figure 1
Selected-ion monitoring (SIM) chromatographs corresponding to authentic paraherquamide A (6) (m/z 494) (A), authentic paraherquamide B (m/z 464) (B), isolation from P. fellutanum culture (m/z 464 and 494) (C), and isolation from A. japonicus JV-23 (m/z 360, 464, and 494) (D).
Figure 2
Figure 2
MSn spectra of paraherquamide A (6) (A) and paraherquamide B (B) from the isolation of P. fellutanum cultures, and asperparaline A (7) (C) from the extracts of A. japonicus JV-23. The integral m/z values of ions for each MSn analysis are included in corresponding graphs.
Figure 3
Figure 3
Selected-ion monitoring (SIM) chromatographs corresponding to the LC-MSn analysis of authentic VM55599 (4) (m/z 350) (A), authentic pre-paraherquamide (5) (m/z 350) (B), isolation from P. fellutanum cultures (m/z 350) (C), and isolation from A. japonicus JV-23 (m/z 350) (D).
Figure 4
Figure 4
MS and MS2 spectra of VM55599 (4) (A) and pre-paraherquamide (5) from the isolation from P. fellutanum culture (B), and pre-paraherquamide (5) from the extracts of A. japonicus JV-23 cultures (C). The integral m/z values of ions for each analysis are included in corresponding graphs.
Scheme 1
Scheme 1
Proposed intramolecular Diels-Alder construction of the bicyclo[2.2.2]diazaoctane core.
Scheme 2
Scheme 2
Proposed unified biogenesis of paraherquamides and asperparalines.
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