Phytotoxic Azaphilones From the Mangrove-Derived Fungus Penicillium sclerotiorum HY5

Abstract

Graphical AbstractRepresentative phytotoxic azaphilones from Penicillium sclerotiorum HY5.

Secondary Metabolites from Aspergillus sparsus NBERC_28952 and Their Herbicidal Activities

“…Azaphilones are a large family of metabolites derived from fungi with variable structures, exhibiting a wide range of biological activities [ 22 ]; however, at present, there are relatively few reports about their herbicidal activities [ 23 ]. As reported in our previous study [ 24 ], Chaetomugilin O, an azaphilone with tetrahydrofuranone, exhibited the most potent inhibition among the tested azaphilones of seedling growth of several weeds.…”

Comprehensive Analysis of Penicillium Sclerotiorum: Biology, Secondary Metabolites, and Bioactive Compound Potential─A Review

“…30,31,29 In this review, total, 85 secondary metabolites were described to be biosynthesized by this P. sclerotiorum (Table 1), encompassing azaphilonidal derivatives, meroterpenoids, polyketides, and peptides. Most of the metabolites that can be extracted and isolated from P. sclerotiorum azaphilones groups such Chlorogeumasnol (1), 39 epi-geumsanol D (2), 38 8a-epi-eupenicilazaphilone C (3), 30 8a-epi-hypocrellone A (4), 30 eupenicilazaphilone C (5), 30 5-bromoisorotiorin (6), 40 5bromosclerotiorin (7), 40 5-chloro-3-[(1E,3R,4R,5S)-3,4-dihydroxy-3,5-dimethyl-1-hepten-1-yl]-1,7,8,8a-tetrahydro-7,8-dihydroxy-7-methyl-(7R,8R,8aS)-6H-2-benzopyran-6-one (8), 27 7-deacetylisochromophilone VI (9), 39 ((1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (10), 30 Isochromophilone IV (11), 30 Isochromophilone H (12), 33 Isochromophilone J (13), 33 Ochlephilone (14), 33 Penazaphilones A−I (15−23), 31 Penazaphilone J−L (24− 26), 31,32 Peniazaphilone A−E (27−31), 31,34,39 Penicilazaphilone B (32), 24 Penicilazaphilone C (33), 35 Penicilazaphilones D-E (34−35), 36 Penicilazaphilone F−G (36−37), 37 Penicilazaphilone I−N (38−43), 38 42 They are most frequently linked to the Aspergillus and Penicillium species. These compounds, known for their diverse structures and significant pharmacological activities, are distributed widely among various organisms, including plants, animals, bacteria, and fungi.…”

“…39 These compounds, sourced from a fungus known for producing azaphilones, hold promise for various biological applications, including the food industry. 39 However, substances like 5bromoisorotiorin (6), penicilazaphilones H (44), and 5bromosclerotiorin (7) showed limited antimicrobial activity against Staphylococcus aureus ATCC 25923 30,33,40 (Table 1).…”

“…Some of the methods are by using column chromatography such as Thin Layer Chromatography (TLC), High Performance Liquid Chromatography (HPLC), High-resolution electrospray ionization mass spectrometry (HRESIMS), Mass Spectroscopy (MS), Nuclear Magnetic Resonance (NMR), X-ray single-crystal diffraction, and Ultraviolet Visible Spectroscopy (UV–vis). ,, In this review, total, 85 secondary metabolites were described to be biosynthesized by this P. sclerotiorum (Table ), encompassing azaphilonidal derivatives, meroterpenoids, polyketides, and peptides. Most of the metabolites that can be extracted and isolated from P. sclerotiorum azaphilones groups such Chlorogeumasnol ( 1 ), epi -geumsanol D ( 2 ), 8a- epi -eupenicilazaphilone C ( 3 ), 8a- epi -hypocrellone A ( 4 ), eupenicilazaphilone C (5) , 5-bromoisorotiorin ( 6 ), 5-bromosclerotiorin (7) , 5-chloro-3-[(1E,3R,4R,5S)-3,4-dihydroxy-3,5-dimethyl-1-hepten-1-yl]-1,7,8,8a-tetrahydro-7,8-dihydroxy-7-methyl-(7R,8R,8aS)-6 H -2-benzopyran-6-one (8) , 7-deacetylisochromophilone VI (9) , ((1 E ,3 E )-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (10) , Isochromophilone IV (11) , Isochromophilone H (12) , Isochromophilone J (13) , Ochlephilone (14) , Penazaphilones A–I (15–23) , Penazaphilone J–L (24–26) , , Peniazaphilone A–E (27–31) , ,, Penicilazaphilone B (32) , Penicilazaphilone C (33) , Penicilazaphilones D-E (34–35), Penicilazaphilone F–G (36–37) , Penicilazaphilone I–N (38–43) , Penicilazaphilones H (44) , Penidioxolane C–D (45–46) , Sclerazaphilone A–I (47–55) , Sclerotioramine (56) , Sclerotiorin (57) , Sclerotiorin A–E (58–62) , and Sclerketide B-C (63–64) (Figures –). According to Jiang et al meroterpenoids are a family of secondary metabolites that are frequently discovered in plants, marine creatures, and fungus .…”

“…Regarding phytotoxicity, compounds such as isochromophilone H (12), sclerotiorins A (58) and B (59), ochlephilone (14), isochromophilone IV (11) , and isochromophilone J (13) displayed effects on Amaranthus retroflexus L. Sclerotiorins A (58) and B (59) showed strong phytotoxicity against radicle and plumule formation, while ochlephilone (14) exhibited growth-inhibiting properties against velvet leaf. , Among these, sclerotiorin B and ochlephilone demonstrated pronounced phytotoxicity toward the development of A. retroflexus L.’s plumule and radicle , (Table ).…”