Natural Product Research, Vol. 19, No. 7, October 2005, 653–659 Aurasperone F – a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C-433 NOUREDDINE BOURASy, FLORENCE MATHIEUy, YANNICK COPPELz and AHMED LEBRIHIy* yLaboratoire de Ge´nie Chimique, E ´ quipe ‘‘Ge´nie des Syste`mes Microbiens’’ UMR 5503 (CNRS, INPT, UPS), ENSAT, 1, Avenue de l’Agrobiopoˆle, B.P. 107, F-31 326 Auzeville-Tolosane Cedex, France zLaboratoire de Chimie de Coordination UPR8241 (CNRS) 205 route de Narbonne, 31 077 Toulouse cedex 4, France (Received 7 May 2004; in final form 7 July 2004) A novel dimeric naphtho--pyrone, named aurasperone F (1), was isolated from the fermentation broth of the culture extracts of Aspergillus niger C-433, isolated from grapes, along with the known compounds fonsecin (2), aurasperone B (3), aurasperone C (4), aurasperone D (5) and aurasperone E (6). The chemical structure of the new natural product was established by extensive one- and two-dimensional NMR spectroscopic studies ( 1 H, 13 C, COSY, HMQC, 1D NOE spectra), as well as on the UV, MS and IR spectral analysis. Keywords: Aspergillus niger; Deuteromycete; Naphtho--pyrones; Aurasperone F 1. Introduction Monomeric and dimeric naphthopyrones are widespread in nature. These compounds have been found in higher plants belonging to the genera Senna (S. longiracemosa [1], S. rugosa [2]), Cassia (C. quinquangulata [3], C. obtusifolia [4], C. pudibunda [5], C. tora [6]) and Paepalanthus bromelioides [7], and in a wide variety of filamentous fungi (deuteromycetes) which belong to the genera Fusarium (F. culmorum, F. gramineum) [8,9] and Aspergillus (A. fonsecaus [10], A. awamori [11,12], A. niger [13–17]). The fungus A. niger is the most common species responsible for the post-harvest decay of fresh fruits, including apples, pears, peaches, citrus, figs, melons, mangoes and grapes [26]. A. niger produced many unknown naphthopyrones which could not be characterized until now [18,19]. The interest of many investigators in this class of compounds is due to their broad-range biological actions: antimicrobial [6], anti- mycobacterial [20], hepatoprotective [4,21], antimutagenic [22], antioxidant [13], *Corresponding author. Tel.: (þ33)-5-62-19-39-44; Fax: (þ33)-5-62-19-39-01. Email: lebrihi@ensat.fr Natural Product Research ISSN 1478-6419 print: ISSN 1029-2349 online ß 2005 Taylor & Francis Group Ltd http://www.tandf.co.uk/journals DOI: 10.1080/14786410412331286955