Penilumamide, a novel lumazine peptide isolated from the marine-derived fungus, Penicillium sp. CNL-338

Abstract

A novel lumazine peptide, penilumamide (1), was isolated from the fermentation broth of a marine-derived fungal strain, identified as Penicillium sp. (strain CNL-338) and the structure of the new metabolite was determined by analysis of ESI-TOF MS data combined with 1D and 2D NMR experiments.

Fungal Endosymbionts of Seaweeds

“…Although marine-derived fungi are marine isolates of terrestrial species, they are prolific producers of novel metabolites of unprecedented structures (Bugni and Ireland 2004;Oh et al 2006;Meyer et al 2010;Kjer et al 2010;Gao et al 2011) which are not produced by their terrestrial conspecifics (Osterhage et al 2000). These metabolites exhibit anticancer, antibacterial, antiplasmodial, anti-inflammatory, nematicidal, antiviral and antiangiogenic activities (Bhadury et al 2006;Newman and Hill 2006;Bhatnagar and Kim 2010;Ohkawa et al 2010).…”

Secondary Metabolites from the Marine Algal-Derived Endophytic Fungi: Chemical Diversity and Biological Activity

“…CNL-338 (isolated from the red alga Laurencia sp. that was collected in the Bahamas islands), yielded a novel lumazine peptide, penilumamide (179) [83]. Application of OSMAC (one strain-many compounds) methodology to Asteromyces cruciatus 763, isolated from an unidentified decaying green alga (La Jolla shore, San Diego), resulted in the isolation of the pentapeptide lajollamide A (180) and the absolute configuration was solved by total synthesis [84].…”

“…(strain no. 6580), associated with a red algal Polysiphonia species (Baltic Sea, Germany), was cultured to produce 11 new botryane sesquiterpenoids(79)(80)(81)(82)(83)(84)(85)(86)(87)(88)(89)…”

Lumazine Peptides from the Marine-Derived Fungus Aspergillus terreus

“…and Aspergillus sp. fungi are structurally distinct, which is primarily due to their peptide nature and anthranilic methyl ester [ 12 , 13 ]. Because terrelumamide A ( 1 ) contains a lumazine moiety, an amino acid residue and a methyl anthranilic ester, it is structurally related to these fungi-derived lumazine peptides.…”

“…and Aspergillus sp. Fungi [ 12 , 13 ]. However, to the best of our knowledge, the 1-methyllumazine-6-carboxylic acid moiety of these terrelumamide compounds is the first such example among natural products.…”