Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Recent advances in the chemistry and biology of azaphilones

“…BS4 37 Antimicrobial (Staphylococcus aureus: 5.0 mg mL À1 ) Colletotrichone C (56) Colletotrichum sp. BS4 37 Antimicrobial (Escherichia coli: 5.0 mg mL À1 ) Coniellin A (57) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 21.5 mM, inhibit NF-kB activation: 4.4 mM) Coniellin B (58) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 19.6 mM) Coniellin C (59) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 21.0 mM) Coniellin D (60) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 18.6 mM, inhibit NF-kB activation: 37.8 mM) Coniellin E (61) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 79.3 mM, inhibit NF-kB activation: 29.4 mM) Coniellin F (62) Coniella fragariae 9 Anti-tumor (inhibit NF-kB activation: 70.7 mM) Coniellin G (63) Coniella fragariae 9 Anti-tumor (MDA-MB-231: 21.6 mM, inhibit NF-kB activation: 11.3 mM) Coniellins H-I (64)(65) Coniella fragariae 35 5 0 ,6 0 -Dihydroxyacetosellin (66) Epicoccum nigrum strain 749 38 Monakaocinol 67Monascus kaoliang 39 Monascuspirolide A (68) Monascus purpureus BCRC 38110 42 Anti-inammatory (inhibit NO production: 17.5 mM) Monascuspirolide B (69) Monascus purpureus BCRC 38110 42 Anti-inammatory (inhibit NO production: 23.5 mM) Thielavialides A-E (70)(71)(72)(73)(74) Thielavia sp. PA0001 40…”

“…Among them, 168 displayed cytotoxic activities and toxic effects on zebrash embryos. 74 As a novel antineoplastic and antibacterial azaphilone, penicilazaphilone C (171) was found from the marine derived fungus Penicillium sclerotiorum M-22, which showed cytotoxicity against human tumor cells B-16 (IC 50 ¼ 0.065 mM) and SGC7901 (IC 50 ¼ 0.720 mM), and also indicated signicant antibacterial activity against four bacteria. 75 Moreover, penicilazaphilones D and E (172-173) were obtained from the sponge-derived fungus Penicillium sclerotiorum and the structure of 172 was further conrmed by single-crystal X-ray diffraction.…”

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“…[141] For example, broccoli is genomically modified food that contains important biomolecules such as glucosinolates and plant pigments including kaempferol, quercetin, lutein and carotenoids, various vitamins, minerals, and amino acids. Broccoli and broccoli extracts also regulate the progression of cancer through anti-inflammatory effects (Son et al, 2016). [142] Pigments such as polyphenols and flavonoids are used in alcoholic beverages.…”

“…Broccoli and broccoli extracts also regulate the progression of cancer through anti-inflammatory effects (Son et al, 2016). [142] Pigments such as polyphenols and flavonoids are used in alcoholic beverages. Dried raw ginseng roots possess ginsenoside that provides light color and its consumption shows antiproliferative activities.…”

Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum

“…[4][5][6][7][8] In the course of our ongoing investigation on new bioactive secondary metabolites from the genus Penicillium in the South China Sea, 9-14 a sponge-derived fungal strain, P. sclerotiorum GDST-2013-0415, attracted our attention, because the extract of the fungal culture showed antibacterial activity. Chemical investigation of the EtOAc crude extract led to the isolation of two new azaphilone derivatives, penicilazaphilones D and E (1 and 2), together with four known compounds (+)-sclerotiorin (3), 15 geumsanol C (4), 16 WB (CAS no. 1701443-52-8, 6H-2benzopyran-6-one, 5-chloro-3-[(1E,3R,4R,5S)-3,4-dihydroxy-3,5dimethyl-1-hepten-1-yl]-1,7,8,8a-tetrahydro-7,8-dihydroxy-7-methyl-(7R,8R,8aS)) (5) 17,18 and geumsanol G (6).…”