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. 2013 Jun 28;76(6):1007-15.
doi: 10.1021/np3008842. Epub 2013 Jun 19.

Peptaibols, tetramic acid derivatives, isocoumarins, and sesquiterpenes from a Bionectria sp. (MSX 47401)

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Peptaibols, tetramic acid derivatives, isocoumarins, and sesquiterpenes from a Bionectria sp. (MSX 47401)

Mario Figueroa et al. J Nat Prod. .

Abstract

An extract of the filamentous fungus Bionectria sp. (MSX 47401) showed both promising cytotoxic activity (>90% inhibition of H460 cell growth at 20 μg/mL) and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). A bioactivity-directed fractionation study yielded one new peptaibol (1) and one new tetramic acid derivative (2), and the fungus biosynthesized diverse secondary metabolites with mannose-derived units. Five known compounds were also isolated: clonostachin (3), virgineone (4), virgineone aglycone (5), AGI-7 (6), and 5,6-dihydroxybisabolol (7). Compounds 5 and 7 have not been described previously from natural sources. Compound 1 represents the second member of the peptaibol structural class that contains an ester-linked sugar alcohol (mannitol) instead of an amide-linked amino alcohol, and peptaibols and tetramic acid derivatives have not been isolated previously from the same fungus. The structures of the new compounds were elucidated primarily by high-field NMR (950 and 700 MHz), HRESIMS/MS, and chemical degradations (Marfey's analysis). All compounds (except 6) were examined for antibacterial and antifungal activities. Compounds 2, 4, and 5 showed antimicrobial activity against S. aureus and several MRSA isolates.

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Figures

Figure 1
Figure 1
Full-scan HRESIMS spectra of peptaibols 3 and 1 (Source voltage: 4.5 kV; Tube lens voltage: 115 V; Capillary voltage: 46 V).
Figure 2
Figure 2
Positive HRESIMS/MS mass fragmentation patterns (HCD) of peptaibols 3 and 1, exhibiting bn or an* [an + Na] ions.
Figure 3
Figure 3
(a) Expansion of the TOCSY spectrum (in methanol-d3: ω2 = 7.7–8.3 ppm, ω1 = 0.8–4.4 ppm), and (b) Key NOESY and HMBC correlations observed in 1

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