Ymf 1029A−E, Preussomerin Analogues from the Fresh-Water-Derived Fungus YMF 1.01029

Abstract

Five new preussomerin analogues, ymf 1029A (1), B (2), C (3), D (4), and E (5), were isolated from the liquid cultures of an unidentified freshwater fungus YMF 1.01029, along with four known compounds, preussomerin C (6), preussomerin D (7), (4RS)-4,8-dihydroxy-3,4-dihydronaphthalen-1(2H)-one (8), and 4,6,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one (9). The structures of new metabolites were determined by analysis of NMR and MS data and by analogy with the data for the known bis-spirobisnaphthalene preussomerins. In vitro immersion experiments showed that these metabolites displayed weak nematicidal activity against Bursaphelenchus xylophilus, while compound 7 was the most potent. This is the first report of these compounds, which antagonize the Bursaphelenchus xylophilus nematode.

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].…”

Metabolites from Two Dominant Thermophilic Fungal Species Thermomyces lanuginosus and Scytalidium thermophilum

“…CR1546 C . Compound 6 was also reported from red oak pathogenic fungus Tubakia dryina , fresh‐water‐derived unidentified fungus YMF1.01029, marine‐associated fungus Daldinia eschscholzii , endophytic Microsphaeropsis arundinis , and Paraphoma sp . Compound 6 was non‐specific phytotoxin that caused large necrosis when placed on leaves of red oak .…”

“…In 2003, 19 , together with five analogs of 17 , was isolated from pathogen Cytospora eucalypticola of Eucalyptus spp . In 2008, 19 and 6 , together with six bis‐spirobisnaphthalene preussomerins, were reported from fresh‐water‐derived unidentified fungus YMF1.01029 . In 2012, 19 and its two hydroxy analogs were isolated from an endophytic fungus Aspergillus fumigatus from Chinaberry or Persian lilac tree Melia azedarach .…”

Cytotoxic hydroanthraquinones from the mangrove-derived fungus Paradictyoarthrinium diffractum BCC 8704

“…The culture was filtered to separate broth (filtrate) and mycelia (residue). The filtrate was extracted with EtOAc (2 × 10 l), and the combined organic layer was concentrated under reduced pressure to obtain a dark brown gum (3.19 (4). X-ray diffraction data were measured on a Bruker-Nonius kappaCCD diffractometer with graphite monochromated MoKα radiation (λ = 0.71073 Å) at 298(2) K. The structure was solved by direct methods using SIR97, 13 and refined with full-matrix leastsquares calculations on F 2 using SHELXL-97.…”

“…To our knowledge, there has been no report of bioactive secondary metabolites from Paradictyoarthrinium or a related genus Dictyoarthrinium. We report here the isolation, structure elucidation and cytotoxic activities of two new hydroanthraquinones, paradictyoarthrins A (1) and B (2), together with three known compounds, preussomerin C (3), 3 ymf 1029C (4) 4 and altenusin (5) 5 (Figure 1).…”