Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp.

Comparative Biological Evaluation of Four Endophytic Fungi Isolated From Nigella Sativa Seeds

“…Endophytic fungi can be considered as a source of chemically novel bioactive secondary metabolites belonging to different chemical classes (Tenguria et al, 2011). Several bioactive metabolites have been characterized from endophytic fungi over last years, and those isolated compounds found to be belong to diverse structural groups such as; alkaloids (Metwaly et al, 2015), isochromenes, (Metwaly, A.M. et al, 2014b) benzopyranones (Metwaly, A. et al, 2014), α-pyrones (Metwaly, A.M. et al, 2014a;Metwaly et al, 2017), steroids (Hussain et al, 2009), terpenoids (Bilal et al, 2018), peptides (Tawfike et al, 2018), polyketones (Zheng et al, 2018), quinones (Stierle and Stierle, 2015), phenolics (Das et al, 2018), xanthones (Li et al, 2016, isocoumarines (Orfali et al, 2015), perylene derivatives (Chagas et al, 2016), furandiones (Li et al, 2015) and butenolide derivatives (Guo et al, 2016) . Recently, there has been a noticeable interest of researches on endophytic fungi producing important metabolites with a great diversity of biological activities such as antileukemic (Metwaly, A.M. et al, 2014a), anti-cancer (Chandra, 2012), antimicrobial(Kumar and Kaushik, 2012), anti-inflammatory (Deshmukh et al, 2009), antimalarial (Wiyakrutta et al, 2004), antileishmanial (Metwaly et al, 2013) and antioxidant (Huang et al, 2007).…”

Recent advances in the chemistry and biology of azaphilones

“…Annulohypoxylomans A-C (1-3) Annulohypoxylon truncatum JS540 11 Annulohypoxylomanols A-B (4)(5) Annulohypoxylon truncatum JS540 11 Annulohypoxyloside (6) Annulohypoxylon truncatum JS540 11 7 Talaromyces stipitatus ATCC 10500 18 (3S,4R)-6-Hydroxy-8-methoxy-3,5-dimethyl isochromanol (8) Penicillium 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.…”

“…21 Colletobredin A (15) exhibited weak NO inhibitory activity in LPS activated murine macrophage RAW264.7 cells. 21 Besides, Monascus pilosus BCRC 38072 and Monascus purpureus BCRC 31499 also produced the isochroman glycoside metabolites, monascuspilorin (19) 22 and monascupurpurin (20), 23 respectively.…”

“…18 The fungus Penicillium sp., collected in the sediment of the hyper saline lake Wadi El-Natrun in Egypt, produced two novel cytotoxic citrinin analogues, (3S,4R)-6-hydroxy-8-methoxy-3,5dimethyl isochromanol (8) and (3S)-6-hydroxy-8-methoxy-3methylisochroman (9). 19 An endophytic fungus from Cordyceps sinensis, Aspergillus fumigatus, gave ve new isochromanes (10)(11)(12)(13)(14), among which 10 and 11 were determined as a pair of enantiomers puried by chiral HPLC methods. 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.…”

Comparative Biological Evaluation of Six Endophytic Fungi Isolated From Vinca Rosea Leaves

“…Over last years, A huge amounts of bioactive secondary metabolites have been isolated from endophytic fungi belonging to different chemical groups such as; tetralones (Kokubun et al, 2003), cytochalasins (Wagenaar et al, 2000), xanthones (Krohn et al, 2009 terpenoids (Bilal et al, 2018), alkaloids (Metwaly et al, 2015), steroids (Hussain et al, 2009), polyketones (Zheng et al, 2018), quinones (Stierle and Stierle, 2015), phenolics (Das et al, 2018), isocoumarines (Orfali et al, 2015), isochromenes, (Metwaly, A.M. et al, 2014b), benzopyranones (Metwaly, A. et al, 2014), furandiones (Li et al, 2015), α-pyrones (Metwaly, A.M. et al, 2014a;Metwaly et al, 2017), and butenolide derivatives (Guo et al, 2016) .…”