Isochromanone derivatives from the endophytic fungus Fusarium sp. PDB51F5

Recent advances in the chemistry and biology of azaphilones

“…This subgroup of azaphilones is characterized by an austdiol core with nineteen members (28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46) (Fig. 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.…”

“…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. 7 Anti-inammatory (inhibit NO production: 22.6 mM) Citrifuran C (26) Aspergillus sp.…”

“…The plausible biosynthetic pathway for citrifurans A-D (24)(25)(26)(27) was assumed by Yin, et al in 2017. 7 The presumed precursors 332 and 333 were originated from acetate and S-adenosyl methionine.…”

“…Aerward, deprotonation of 335 afforded two kinds of enolate anions, 336 and 337, which subsequently heterodimerized with 332 and 334 through a Michael addition reaction to form adducts 338 and 339, respectively. A subsequent intramolecular nucleophilic addition and reduction of 339 constructed a dihydropyran ring in citrifuran A (24), which further went via oxidization to form the epimers, citrifuran B (25) and citrifuran C (26). Similarly, the Scheme 18 Biosynthesis of 6 00 -hydroxy-(R)-mitorubrinic acid, purpurquinone D (À)-mitorubrinic acid, (À)-mitorubrin, and purpurquinone A.…”

“…6 Chemical investigation of a mangrove-derived fungus Penicillium chrysogenum HND11-24, led to the characterization of penicitol A (23), a citrinin dimer with a novel tetracyclic skeleton, which was found with cytotoxicity against HeLa, BEL-7402, HEK-293, HCT-116, and A549 cell lines (IC 50 ¼ 4.6-10.5 mM). 24 Citrifurans A-D (24)(25)(26)(27), four uncommon heterodimers of azaphilone and furanone derivatives, were discovered from Aspergillus sp., meanwhile structure of 24 was conrmed by single-crystal X-ray diffraction, among which 24-26 displayed moderate inhibitory on NO production in RAW 264.7 macrophages with IC 50 values of 18.3, 22.6, and 25.3 mM, respectively. 7…”