Eremophilane sesquiterenes from the marine fungus Penicillium sp. BL27-2

Fifty years of marine mycology

“…collected on mangrove wood in Thailand (Lin et al 2002a); alkaloids: two new diketopiperazines were obtained from a Penicillium sp. isolated from a deep ocean sediment sample, and roquefortine H, J and I (Du et al 2010); cyclic peptides: marine fungi produce a wide range of peptides as illustrated with Beauveria felina isolated from the marine alga Caulerpa yielding two new cyclic depsipeptides; pseudodestruxin C and β-Me-pro destruxin E chlorohydrin (Lira et al 2006); Spicellum roseum isolated from a Caribbean sponge Ectyplasia perox produced two new cyclohexadepsiptides spicellamide A and B (Kralj et al 2007); mangrove strain #2516 yielded three new cyclotetrapeptides and four cyclic dipeptides, while strain #2524 isolated from seeds of Avicennia marina produced two new cyclic pentapeptides (cyclo-(L-Phe-L-Leu 1 -L-Leu 2 -L-Leu 3 -llle, and cyclo-(Phe-Val-Leu-Leu-Leu), the former exhibiting cytotoxic activity against human cancer cell line Bel-7401 (Li et al 2004), and the hexacylic dipeptide azonazine was isolated from the marine derived fungus Aspergillus insulicola (Wu et al 2010); isocumarins: two new isocumarins avicennin A and B, and vermopyrone were isolated from the leaf endophyte of Avicennia marina (Lin et al 2001c), while isoculmorin was obtained from the mangrove fungus Kallichroma tethys (Alam et al 1996;Kong and Kim 2002); terpenes: a number of marine fungi produce these compounds: Dendryphiella salina (dendryphielins A-D, Guerriero et al 1988); endophyte #2492 and Halorosellinia oceanica (two unique dipterpenes isomers hypoxylin A and B, and a sesquiterpene lactone: Luo et al 2004;Li et al 2001); unidentified marine fungus (MPUC 046), isolated from a brown alga Ishige okamurae (phomactin I, 13-epi-phomactin I and phomatcin J: Ishino et al 2010); Penicillium sp., isolated from sea mud (two new eremophilane sesquiterpenes: 3-acetyl-9,7(11)-dien-7a hydroxyl-8-oxoeremophilane and 3-acetyl-13-deoxyphemenon: Huang et al 2008); diketopiperazines: an Aspergillus sp. isolated from Mytilus edulis (mussel) yielded a series of prenylated diketopiperazines, notoamides A-D and F-K (Kato et al 2007); while another species A. fumigatus isolated from Stichopus japonics (holothurian) produced seven such compounds including spiro-3-indolinone, spirotryprostatin C, D and E, and Eurotium rubrum and P. bilaii yielded dehydroariecolorin L and dehydroechinulin and bilains A, B and C respectively ); lactones: Helicascus kanaolanus, a mangrove ascomycete yielded helicascolides A and B (Poch and Gloer 1989), while a Eutypa sp.…”

Terpenes from Marine-Derived Fungi

“…BL27-2, isolated from sea mud in the Bering sea [8]. 13 had been synthesized in the course of the structure elucidation of sporogen A0 I from a mycophilic Hansfordia sp.…”

Four New Chloro-Eremophilane Sesquiterpenes from an Antarctic Deep-Sea Derived Fungus, Penicillium sp. PR19N-1

“…The IR spectrum showed the presence of hydroxyl, carbonyl and double bond moieties, displaying characteristic absorption bands at 3418, 1715, 1656 cm −1 , respectively. The 1 H and 13 C NMR resonances (Table 1, Table 2) of 3 were reminiscent of the known eremophilane-type sesquiterpenes that possessed an 8-oxo-7(11),9(10)-diene units [17,18]. The related HMBC correlations were further confirmed as shown in Figure 2.…”