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Truncatones A–D, benzo[j]fluoranthenes from Annulohypoxylon species (Xylariaceae, Ascomycota)

Author:
Sudarman, Enge, Kuhnert, Eric, Hyde, Kevin D., Sir, Esteban Benjamin, Surup, Frank, Stadler, Marc
Source:
Tetrahedron 2016 v.72 pp. 6450-6454
ISSN:
0040-4020
Subject:
Xylariaceae, chemical reactions, chemical structure, circular dichroism spectroscopy, cytotoxicity, fibroblasts, fruiting bodies, fungi, mice, nuclear magnetic resonance spectroscopy, organic compounds
Abstract:
From stromata (fruiting bodies) of three xylariaceous fungi belonging to the genus Annulohypoxylon (A. leptascum, A. cf. truncatum and an unidentified Annulohypoxylon sp.), truncatone A (1), three unprecedented derivatives named truncatones B–D (2–4) besides the known 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (BNT, 5), hypoxylonol C (6) and hypoxylonol F (7) were isolated. Planar structures of the new benzo[j]fluoranthene derivatives 2–4 were determined on the basis of NMR and HRESIMS data. While the relative configuration of 4 was demonstrated by ROESY NMR data and 1H,1H coupling constants, absolute configurations of 1, 2, 4 were determined by CD spectroscopy. Compounds 1, 3 and 4 exhibited cytotoxicity against the mouse fibroblast cell line L929.
Agid:
5515694