Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus

Abstract

Bioassay-guided fractionation of a culture extract of Beauveria felina EN-135, an entomopathogenic fungus isolated from a marine bryozoan, led to the isolation of a new cyclodepsipeptide, iso-isariin D (1); two new O-containing heterocyclic compounds that we have named felinones A and B (2 and 3); and four known cyclodepsipeptides (4–7). The structures were elucidated via spectroscopic analysis, and the absolute configurations of 1 and 2 were determined using single-crystal X-ray diffraction and CD, respectively. All isolated compounds were evaluated for antimicrobial activity and brine-shrimp (Artemia salina) lethality.

Discovery of McrA, a master regulator of Aspergillus secondary metabolism

“…Although not detected by HPLC-DAD-MS, a minor compound, felinone A (14), a recently discovered antibiotic (Du et al, 2014), was also isolated from large-scale cultures of LO8111. We have characterized all the nonreducing polyketide synthase (NR-PKS) products produced by A. nidulans (Ahuja et al, 2012).…”

Identification of cyclosporin C from Amphichorda felina using a Cryptococcus neoformans differential temperature sensitivity assay

“…However, strains of this species have also been recovered from soils, marine sediments, and prepared yeast (Anonymous 2017; de Hoog 1972; Langenfeld et al 2011; Yurchenko et al 2014). Various secondary metabolites have been reported from A. felina , including the isariins (Deffieux et al 1981), isarfelins (Guo et al 2005), oxirapentyns (Yurchenko et al 2014), isariketides (Smetanina et al 2017), and felinones (Du et al 2014). Thus, its genome sequence will offer the raw data needed to link this rich array of secondary metabolites to their cognate gene clusters.…”

Recent advances in the chemistry and biology of azaphilones

“…3 and Table 1), including fusaraisochromenone (28), 25 7(S)-7-hydroxy-3,7dimethyl-isochromene-6,8-dione (32), 26 nemanecins A-C (34-36), 27 and perangustols A and B (37)(38). 28 Felinone A (29) was obtained from a marine bryozoan derived fungus Beauveria felina EN-135 with weak activity against brine shrimp with the lethal rate of 61.4% (100 mg mL À1 ), 16 while absolute conguration of which was revised by chemical synthesis. 29 Moreover, xylariphilone (30), the diastereoisomer of 29, was metabolized by the seagrass-derived fungus Xylariales sp.…”

“…19 Cytotoxic (L5178Y: 26.20% at 10 mg mL À1 ) (3S)-6-Hydroxy-8-methoxy-3-methylisochroman (9) Penicillium sp. 19 Cytotoxic (L5178Y: 16.10% at 10 mg mL À1 ) (S)-3,6-Dihydroxy-8-methoxy-3methylisochroman-4-one (10) Aspergillus fumigatus 20 Cytotoxic (MV4-11: 38.39 mM) (R)-3,6-Dihydroxy-8-methox-3methylisochroman-4-one (11) Aspergillus fumigatus 20 8-Methoxy-3-methylisochromane-3,6-diol (12) Aspergillus fumigatus 20 Cytotoxic (MV4-11: 30.00 mM) 3,8-Dimethoxy-3-methylisochroman-6-ol (13) Aspergillus fumigatus 20 3,6,7,8-Tetramethoxy-3-methylisochromane (14) Aspergillus fumigatus 20 Colletobredin A (15) Colletotrichum aotearoa BCRC 09F0161 21 Anti-inammatory (inhibit NO production: 182.2 mM) Colletobredins B-D (16)(17)(18) Colletotrichum aotearoa BCRC 09F0161 21 Monascuspilorin (19) Monascus pilosus BCRC 38072 22 Monascupurpurin (20) Monascus purpureus BCRC 31499 23 Peyronellone A (21) Peyronellaea glomerate 6 Antioxidant (ABTS: 88.8 mM, DPPH: 126.3 mM) Peyronellone B (22) Peyronellaea glomerate 6 Antioxidant (ABTS: 95.2 mM, DPPH: 83.5 mM); hypoxia-protective activity (improved the survival rate of H/R-treated human umbilical vein endothelial cells from 35% to 70% at 5 mM) Penicitol A (23) Penicillium chrysogenum HND11-24 24 Cytotoxic (HeLa: 4.6 mM, BEL-7402: 10.5 mM, HEK-293: 6.7 mM, HCT-116: 5.6 mM, A549: 7.6 mM) Citrifuran A (24) Aspergillus sp. 7 Anti-inammatory (inhibit NO production: 18.3 mM) Citrifuran B (25) Aspergillus sp.…”

“…20 Meanwhile, 10 and 12 exhibited moderate activities against MV4-11 cell line with IC 50 values of 38.4 and 30.0 mM, respectively. 20 As the rst report on isochroman glycoside metabolites from the genus Colletotrichum, colletobredins A-D (15)(16)(17)(18) were extracted from Colletotrichum aotearoa BCRC 09F0161, an endophytic fungus found in the leaves of an endemic Formosan plant Bredia oldhamii Hook. f. (Melastomataceae).…”