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. 2016 Mar 25;79(3):455-62.
doi: 10.1021/acs.jnatprod.5b00604. Epub 2015 Oct 21.

1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus

Peng Fu  1 , Scott La  1 , John B MacMillan  1
Affiliations

1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus

Peng Fu et al. J Nat Prod. .

Abstract

Two new 1,3-oxazin-6-one derivatives (1 and 2) and six new bohemamine-type pyrrolizidine alkaloids (3-8) were isolated from the marine-derived Streptomyces spinoverrucosus strain SNB-048. Their structures including the absolute configurations were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Compounds 1 and 2 possess a γ-lactam moiety and a 1,3-oxazin-6-one system.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Chart 1
Chart 1
Scheme 1
Scheme 1. Mechanism for the Conversion of N-Acyl-β-lactams into 1,3-Oxazin-6-ones
Figure 1
Figure 1
Key correlations for the structural assignment of 1–8.
Figure 2
Figure 2
Two structures, 1 and 1a, in general agreement with the NMR data.
Figure 3
Figure 3
Selected NOESY correlations of 1, 3a, and 4–8.
Figure 4
Figure 4
(a) ECD spectra of 1 and 2. (b) Ring chirality and ECD sign of γ-lactams and the conformation of 1.
Figure 5
Figure 5
Measured and calculated ECD spectra for 1.
Figure 6
Figure 6
ECD spectra and the representation of the octant rule and helicity rule for the cyclopentenone moiety of 3 (a) and 9 (b).
Figure 7
Figure 7
ECD spectra of 4–8.
Scheme 2
Scheme 2. Plausible Biogenetic Pathway of Compounds 1–3
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