Discovery of Naphthol Tetramers from Endolichenic Fungus Daldinia childiae 047219 Based on MS/MS Molecular Networking

Endolichenic Fungi: A Promising Medicinal Microbial Resource to Discover Bioactive Natural Molecules—An Update

“…Since 2015, 25 chromogenic ketones together with 22 isocoumarins have been reported. For example, Kim et al isolated two new chromones, phomalichenones C-D (44)(45), and three known chromone derivatives (46)(47)(48) from the endolichenic fungus Phoma sp. in 2018 [28].…”

“…In 2022, the compound 4,6dihydroxy-5-methylphthalide (118) was isolated from the endolichenic fungus Talaromyces sp., associated with Xanthoparmelia angustiphylla, by Yuan et al [35]. Kim et al developed an efficient methodology using a feature-based MS/MS molecular networking analysis to discover the novel secondary metabolites from the reported endolichenic fungus, and this successfully resulted in the isolation of four compounds, 1,8-dimethoxy naphthalene (119), 8-methoxy-1-naphthol (120), 1-(2,6-dihydroxyphenyl)butan-1-one (121), and 2,6dihydroxya-cetophenone (122), from Daldinia childae in 2023 [45].…”

“…In addition, aromatic naphthalene dimers, trimers, and tetramers (Figure 11) have been found in the secondary metabolites of endolichenic fungi. Kim et al obtained fourteen daldinol polyketides, including naphthol dimers, trimers, and tetramers, from Daldinia childae 047,219 by using a feature-based MS/MS molecular networking analysis in 2023 [45]. These aromatic polynaphthalenes mainly include six previously unreported naphthol tetramers: 1,1 ′ ,3 ′ ,3 ′′ ,1 ′′ ,1 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′tetraol (227), 1,1 ′ ,3 ′ ,1 ′′ ,3 ′′ ,3 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′ -tetraol (228), 3,3 ′ ,1 ′ ,1 ′′ ,3 ′′ ,3 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′ -tetraol (229), 1,1 ′ ,3 ′ ,3 ′′ ,1 ′′ ,3 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′ -tetraol (230), 3,1 ′ ,3 ′ , 1 ′′ ,3 ′′ ,3 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′ -tetraol (231), and 3,1 ′ ,3 ′ ,3 ′′ , 1 ′′ ,3 ′′′ -quaternaphthalene-5,5 ′ ,5 ′′ ,5 ′′′ -tetramethoxy-4,4 ′ ,4 ′′ 4 ′′′ -tetraol (232), and 8 known polyketides, daldinol (233), nodulisporin E (234), nodulisporin A (235), nodulisporin B (236), 1,1 ′ ,3 ′ ,3 ′′ -ternaphthalene-5,5 ′ ,5 ′′ -trimethoxy-4,4 ′ ,4 ′′ -triol (237), 3,1 ′ ,3 ′ ,3 ′′ -ternaphthalene-5,5 ′ ,5 ′′ -trimethoxy-4,4 ′ ,4 ′′ -triol (238), 1,1 ′ ,3 ′ ,1 ′′ -ternaphthalene-5,5 ′ ,5 ′′ -trimethoxy-4,4 ′ ,4 ′′triol (239), and 3,1 ′ ,3 ′ ,1 ′′ -ternaphthalene-5,5 ′ ,5 ′′ -trimethoxy-4,4 ′ ,4 ′′ -triol (240).…”

Cytotoxic Peptaibols from Trichoderma strigosum

“…Molecular networking (MN) arranges MS/MS spectra into a network-shaped map based on spectral similarity indicating structural similarity between molecules. , Molecular networking is a potent method for rapid and effective dereplication and targeted discovery of natural products, making it possible to predict the molecular composition of extracts before laborious chromatographic isolation and in-depth structure identification. , …”