Avellanin C, an inhibitor of quorum-sensing signaling in Staphylococcus aureus, from Hamigera ingelheimensis

H. ingelheimensis NRRL 29060 was cultured in A-3M liquid medium for 6 days on a rotary shaker and the whole culture broth was extracted with 1-butanol. After evaporation, the crude extract was subsequently subjected to silica gel and octadecylsilyl (ODS) column chromatography, followed by HPLC purification to yield avellanin C (1).

Avellanin C (1) was obtained as a white amorphous solid. HR-ESITOFMS analysis gave a pseudomolecular ion [M+Na]⁺ at m/z 618.2681 corresponding to the molecular formula of C₃₄H₃₇N₅O₅ (Δ −0.6 mmu, for C₃₄H₃₇N₅O₅Na), which was consistent with the NMR data. ¹³C NMR and HSQC spectral analyses revealed the presence of 34 carbons assignable to five carbonyl carbons, four sp² quaternary carbons, 10 sp² methines, four sp³ methines, five sp³ methylenes and two methyls. The ¹H NMR spectrum displayed resonances for the aromatic protons, four methine protons ascribed to the α-protons of amino acids and three NH protons. These spectral features suggested the peptidic structure of 1 and the presence of aromatic groups within.

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