Two new acaranoic acids, named seimatoporic acid A and B (1, and 2), together with six known compounds, R-(-)-mellein (3), cis-4-hydroxymellein (4), trans-4-hydroxymellein (5), 4R-hydroxy-5-methylmellein (6), (-)-5-hydroxymethylmellein (7), and ergosterol (8) were isolated from an endophytic fungus, Seimatosporium sp, by a bioassay-guided procedure. The structures of the new compounds have been assigned from analysis of the 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and NOESY experiments. A mixture of compounds 1 and 2 showed strong antifungal activity against Botrytis cinerea, Septoria tritici, and Pyricularia oryzae.
HussainH, KrohnK, FloerkeU, SchulzB, DraegerS, PescitelliG, AntusS, KurtánT. (2007) Absolute configurations of globosuxanthone A and secondary metabolites from Microdiplodia sp. – A novel solid-state CD/TDDFT approach. European Journal of Organic Chemistry, 292–295.
2.
SaleemM, HussainH, AhmedI, DraegerS, SchulzB, KrohnK. (2011) Viburspiran: A new member of new class octadride of anhydide family. European Journal of Organic Chemistry, 808–812.
3.
DaiJ, HussainH, DrägerS, SchulzB, KurtánT, PescitelliG, FlörkeU, KrohnK. (2010) Metabolites from the fungus Phoma sp. 7210, associated with Aizoon canariense. Natural Product Communications, 5, 1175–1180.
4.
QinS, HussainH, SchulzB, DraegerS, KrohnK. (2010) Two new metabolites, epoxydine A and B, from Phoma sp. Helvetica Chimica Acta, 93, 169–174.
5.
HussainH, AkhtarN, SchulzB, DraegerS, PescitelliG, AntusS, KurtanT, KrohnK. (2009) New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica. European Journal of Organic Chemistry, 749–756.
6.
KrohnK, KouamSF, KuigouaGM, HussainH, Cludius-BrandS, FlörkeU, KurtánT, PescitelliG, Di BariL, DraegerS, SchulzB. (2009) Xanthones and new oxepino[2,3-b]chromones from three endophytic fungi. Chemistry, a European Journal, 15, 12121–12132.
7.
HuneckS, HoefleG. (1980) Structure of acaranoic and acarenoic acids. Phytochemistry, 19, 2713–2715.
8.
FlörkeU, KrohnK, UllahZ, HussainH. (2006) An orthorhombic modification of (R)-(-)-8-hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one [(R)-(-)-mellein]. Acta Crystallography, o3539–o3541;
9.
KrohnK, KockI, ElsässerB, FlörkeU, SchulzBS, DraegerS, PescitelliG, AntusS, KurtanT. (2007) Bioactive natural products from the endophytic fungus ascochyta sp. from Meliotus dentatus-Configurational assignment by solid-state CD and TDDFT calculations. European Journal of Organic Chemistry, 1123–1129;
10.
OkunoT, OikawaS, GotoT, SawaiK, ShirahamaH, MatsumotoT. (1986) Structures and phytotoxicity of metabolites from Valsa ceratosperma. Agriculture Biological Chemistry, 50, 997–1001;
11.
GoulstonG, MercerEI, GoadLJ. (1975) The identification of 24-methylene-24,25-dihydrolanosterol and other possible ergosterol precursors in Phycomyces blakesleeanus and Agaricus campestris. Phytochemistry, 14, 457–462.
12.
SchulzB, SuckerJ, AustHJ, KrohnK, LudewigK, JonesPG, DoeringD. (1995) Biologically active secondary metabolites of endophytic Pezicula species. Mycological Research, 99, 1007–1015;