New Furan Derivatives from a Mangrove-Derived Endophytic Fungus Coriolopsis sp. J5

Abstract

Six new furan derivatives, named 5-(3-methoxy-3-oxopropyl)-furan-2-carboxylic acid (1), 1-(5-(2-hydroxypropanoyl)-furan-2-yl)-pentan-3-one (2), 2-hydroxy-1-(5-(1-hydroxypentyl)-furan-2-yl)-propan-1-one (3), 1-(5-(1,2-dihydroxypropyl)-furan-2-yl)-pentan-1-one (4), 5-(1-hydroxypent-4-en-1-yl)-furan-2-carboxylic acid (5) and 5-(3-hydroxypentyl)-furan-2-carboxylic acid (6), together with two new natural products, named 5-(1-hydroxypentyl)-furan-2-carboxylic acid (7) and (E)-5-(2-carboxyvinyl)-furan-2-carboxylic acid (8), were isolated from the solid rice fermentation of endophytic fungus Coriolopsis sp. J5, which was derived from mangrove plant Ceriops tagal. Their structures were unambiguously elucidated based on 1D and 2D NMR spectroscopy, and by HRESIMS measurements, as well as by comparison with the literature.

Macrocyclic polyketides with siderophore mode of action from marine heterotrophic Shewanella algae : Prospective anti‐infective leads attenuate drug‐resistant pathogens

“…The previously reported furan carboxylic acid compounds recorded protons at δ H 7·10/6·21 ( δ C 142·8, 121·3, 108·8, 163·1) (Chen et al . 2017), which were found to be lesser when compared with the presently reported compound ( δ H 7·33/6·89; δ C 149·7, 128·7, 115·3, 115·5). This might be due to the presence of hydroxyl group in compound 1 , whereas the previously reported compound enclosed carboxylic acid at C‐2' (Chen et al .…”

“…This might be due to the presence of hydroxyl group in compound 1 , whereas the previously reported compound enclosed carboxylic acid at C‐2' (Chen et al . 2017). The HMBCs from δ 7·44 (H‐2) to δ 149·7 (C‐1') attributed that benzene ring was bonded to 5′‐hydroxy furan through the oxygen atom between C‐1 of benzene and C‐1′ of furan rings.…”

The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus

“…The furan compound 5-(hydroxymethyl)furan-3-carboxylic acid was identified for the first time as a natural product in cultures of Polyporus ciliatus [20], and afterwards reported from other fungi (Table 1). Although furan derivatives are not an extensive class of fungal compounds [35], over the past few years the literature concerning these natural products has been enriched by new reports [36,37,38,39,40]. According to their biosynthetic origin, the structure of natural furan derivatives shows the presence of furan rings substituted in position 2 and 5 [35].…”

Marine natural products

“…292 Sesquiterpenes 755, 756 (ref. 293) and furan derivatives 757-764, 294 were obtained from Coriolopsis strains, of which 763 and 764 were obtained for the rst time as NPs. Diaporthe species were the source of a number of alkaloids including 765-768, 295 isoindolinones 769, 770, 295 diaporisoindoles A 771, B 772, C 773 (an unusual diisoprenylisoindole dimer) and tenellone C 774.…”