Decaspirones F−I, Bioactive Secondary Metabolites from the Saprophytic Fungus Helicoma viridis

Abstract

Decaspirones F-H (1-3), three new spirobisnaphthalene derivatives, and one new non-spirobisnaphthalene, decaspirone I (4), have been isolated from cultures of an isolate of the saprophytic fungus Helicoma viridis. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The absolute configuration of decaspirone F (1) was established by X-ray crystallographic analysis of its mono-bromobenzoate derivative. In standard disk assays, compounds 1-4 showed modest activity against Pseudomonas aeruginosa (multiple antibiotic-resistant strain, ATCC 27853), and decaspirone G (2) also displayed activity against Lactococcus lacti (PCM 2379).

Metabolic Products of the Endophytic Fungus Microsphaeropsis sp. from Larix decidua

“…[11] They proved that the socalled degenerate coupling between the two benzoates is fully responsible for the observed CD of 1c, while non-degenerate benzoate-naphthalene couplings give much weaker effects (see Supporting Information). In two recent papers Jiao et al [2] and Hu et al [3] reported on the isolation of related spirodioxynaphthalenes from the aquatic fungus Descaisnelle thyridoides and the saprophytic fungus Helicoma virids, respectively. Palmarumycin M 1 (1a) is the 6,7-dihydro derivative of decaspirone A.…”

“…The known decaspirone (2) and the papyracillic acids A (4) and B (5) ( Figure 1) were also identified. The publication of related spirodioxynaphthalenes [2,3] and the termination of the biological activity screening of our compounds at BASF AG prompted us to disclose the isolation, structural elucidation and herbicidal, antifungal and antibacterial activities of these new compounds.…”

Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues

“…Since then, several new spirobisnaphthalene natural products have been isolated and the total syntheses of some of these have been accomplished by different research groups. In addition, many non-natural derivatives have been prepared by synthesis and evaluated for their biological activities [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. The spirobisnaphthalenes isolated from fungi along with their biological activities were further reviewed in 2010 [19,20].…”

Regioselective Synthesis of Spiro-2-aminopyrimidinone Derivatives in Ionic Liquid as Green Solvent

“…In addition to their medical uses, some spiro-compounds have found other uses in the agricultural and industrial fields. For example, they are used as antifungal agents 30 , pesticides 31 , laser dyes 32 and electroluminescent devices 33 . Spiro-compounds have also been recently used as antioxidants 34 .…”