Three New Naphthoquinone Pigments Isolated from the Freshwater Fungus, Astrosphaeriella papuana

Abstract

Three new naphthoquinones, astropaquinones A – C (1–3), were isolated from cultures of the freshwater fungus Astrosphaeriella papuana YMF 1.01181, together with the known compound, 6-hydroxy-2,4-dimethoxy-7-methylanthraquinone (4). The structures of the compounds were settled mainly by interpretation of their 1D and 2D NMR spectra. Astropaquinone B (2) and C (3) were found to possess a rare pyranonaphthoquinone skeleton containing a lactol ring. Furthermore, compounds 1–4 showed moderate antagonistic activity against nine fungi and four bacterial strains.

freshwater fungus - Astrosphaeriella papuana - pyranonaphthoquinone - astropaquinones - lactol ring - antimicrobial activity - Melanommataceae

References

• 1 Claudio A, Raffaele P, Mara F, Antonio E, Angelo V. Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum.  J Agric Food Chem. 2004;  52 2997-3001
• 2 Cragg G M, Newman D J, Snader K M. Natural products in drug discovery and development.  J Nat Prod. 1997;  60 52-60
• 3 Dreyfuss M M, Chapela I H. The discovery of natural products with therapeutic potential. Boston; Butterworth-Heinemann 1994
• 4 Henkel T, Brunne R M, Muller H, Reichel F. Statistical investigation into the structural complementarity of natural products and synthetic compounds.  Angew Chem Int Ed. 1999;  38 643-647
• 5 Gloer J B. The chemistry of fungal antagonism and defence.  Can J Bot. 1995;  73 S1265-S1274
• 6 Gloer J B. TOR: environmental and microbial relationships. Wicklow DT, Soderstrom BE TOR-mycota. Heidelberg; Springer Verlag 1997: 249-268
• 7 Grabley I S, Thiericke R, Zeeck A. TOR: the chemical screening approach. Grabley S, Thiericke R TOR – drug discovery from nature. Berlin; Springer Verlag 1999: 124-148
• 8 Jiao P, Swenson D C, Gloer J B, Campbell J, Shearer C A. Decaspirones A–E, bioactive spirodioxynaphthalenes from the freshwater aquatic fungus Decaisnella thyridioides.  J Nat Prod. 2006;  69 1667-1671
• 9 Dong J Y, Li R, He H P, Zhang K Q. Nematicidal sphingolipids from the fresh water fungus Paraniesslia sp. YMF 1.01400.  Eur J Lipid Sci Technol. 2005;  107 779-785
• 10 Dong J Y, Zhu Y H, Song H C, Li R, He H P, Zhang K Q. Nematicidal resorcylides from the aquatic fungus Caryospora callicarpa YMF 1.01026.  J Chem Ecol. 2007;  33 1115-1126
• 11 Dong J Y, Zhou Y P, Li R, Zhou W, Li L, Zhang K Q. New nematicidal azaphilones from the aquatic fungus Pseudohalonectria adversaria YMF 1.01019.  FEMS Microbiol Lett. 2006;  264 65-69
• 12 Oh H, Gloer J B, Shearer C A. Massarinolins A–C: new bioactive sesquiterpenoids from the aquatic fungus Massarina tunicata.  J Nat Prod. 1999;  62 497-501
• 13 Reátegui R F, Gloer J B, Campbell J, Shearer C A. Ophiocerins A–D and ophioceric acid: tetrahydropyran derivatives and an africane sesquiterpenoid from the freshwater aquatic fungus Ophioceras venezuelense. .  J Nat Prod. 2005;  68 701-705
• 14 Oh H, Swenson D C, Gloer J B, Shearer C A. New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicate.  J Nat Prod. 2003;  66 73-79
• 15 Wicklow D T, Joshi B K, Gamble W R, Gloer J B, Dowd P F. Antifungal metabolites (Monorden, Monocillin IV, and Cerebrosides) from Humicola fuscoatra traaen NRRL 22980, a mycoparasite of Aspergillus flavus sclerotia.  Appl Environ Microbiol. 1998;  64 4482-4484
• 16 Jain R K, Ravindra K, Srivastava S D, Savitri D. Two new anthraquinones in the roots of Morinda citrifolia.  Proceedings of the National Academy of Sciences, India, Section A. Physical Sciences. 1992;  62 11-13
• 17 Sendl A, Chen J L, Jolad S D, Stoddart C, Rozhon E, Kernan M. Two new naphthoquinones with antiviral activity from Rhinacanthus nasutus.  J Nat Prod. 1996;  59 808-811
• 18 Singh S B, Michael G C, Richard G B, Jack L S, Anne W D, Michael A G. Structure of stereochemistry of thysanone: a novel human rhinovirus 3C-protease inhibitor from Thysanophora penicilloides.  Tetrahderon Lett. 1991;  39 5279-5282
• 19 Han L, Huang X S, Dahse H M, Moellmann U, Fu H Z, Grabley S, Sattler I, Lin W. Unusual naphthoquinone derivatives from the twigs of Avicennia marina.  J Nat Prod. 2007;  70 923-927
• 20 Gill M, Donner C D. Synthesis and absolute stereochemistry of thysanone.  Tetrahedron Lett. 1999;  40 3921
• 21 Thomson R H. Naturally occuring quinines, 2nd edition. London; Academic 1971: 282
• 22 Iwata D, Ishibashi M, Yamamoto Y, Cribrarione B. A new naphthoquinone pigment from the myxomycete Cribraria cancellata.  J Nat Prod. 2003;  66 1611-1612
• 23 Puyvelde L V, Hady S E, Kimpe N D, Feneau-Dupont J, Declercq J P. Isagarin, a new type of tetracyclic naphthoquinone from the roots of Pentas longiflora.  J Nat Prod. 1998;  61 1020-1021
• 24 Fujiwara A, Mori T, Iida A, Ueda S, Hano Y, Nomura T. Antitumor-promoting naphthoquinones from Catalpa ovata. .  J Nat Prod. 1998;  61 629-632
• 25 Wang W, Li T, Milburn R, Yates J, Hinnant E, Luzzio Noble M J.SA, Attardo G. Novel 1, 3-disubstituted-5, 10-dihydro-5, 10-dioxo-1H-benzo[g]isochromene-3-carboxamides as potent antitumor agents.  Bioorg Med Chem Lett. 1998;  8 1579-1584
• 26 Lee H, Hong S S, Kim Y H. Synthesis and in vitro evaluation of 3-substituted-1-azaanthraquinones.  Bioorg Med Chem Lett. 1996;  6 933-936
• 27 Paranagama P A, Wijeratne E MK, Burns A M, Marron M T, Gunatilaka M K, Arnold A E, Gunatilaka A ALJ. Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa: first report of metabolites of an endolichemic fungus.  J Nat Prod. 2007;  70 1700-1705
• 28 Nagarajan R, Narasimhachari N, Kadkol M V, Gopalkrishnan K S. Structure of herbarin.  J Antibiot. 1971;  24 249-252

1 These authors contributed equally to this work.