Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Abstract

A new coumarin, 4,6-dihydroxy-7-formyl-3-methylcoumarin (1), and an α-pyrone derivative, 6-[(7S,8R)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one (2), together with four known α-pyrone derivatives (3-6), were isolated from the broth extract of the plant endophytic fungus Pestalotiopsis versicolor. Their structures were elucidated by extensive spectroscopic analysis and by comparison of the chemical shift values with those of related known compounds.

Identification and characterization of compounds from Chrysosporium multifidum, a fungus with moderate antimicrobial activity isolated from Hermetia illucens gut microbiota

“…All the compounds (Fig 2) were identified by comparison of their spectroscopic data (HRMS and 1 H and 13 C NMR) with literature-reported values, as well as careful examination of their 2D NMR spectra (COSY, HSQC, HMBC). Optical rotations were also coherent with published data, except for ( 4 ), for which we found an optical rotation close to zero indicating the possible isolation of a racemic mixture (found [α] 20 D -4.3, c = 0.16, MeOH/CH 2 Cl 2 9/1; published [α] 25 D -98.7, c = 0.6, MeOH) [23].…”

“…Bioguided analysis of the ethyl acetate extract of C . multifidum broth resulted in the isolation of 4-methoxy-2H-pyran-2-one ( 1 ) [20], 4-methoxy-6-pentyl-2H-pyran-2-one ( 2 ) [21], 6-(1-hydroxypentyl)-4-methoxy-pyran-2-one ( 3 ) [21,22], 6-[8-propyloxiran-1-yl]-4-methoxy-pyran-2-one ( 4 ) [23], pestalotin ( 5 ) [24,25], 5,6-dihydro-4-methoxy-6-(pentanoyloxy)-2H-pyran-2-one ( 6 ) [22,25] and cyclo-(L-Pro-L-Val) ( 7 ) [26]. All the compounds (Fig 2) were identified by comparison of their spectroscopic data (HRMS and 1 H and 13 C NMR) with literature-reported values, as well as careful examination of their 2D NMR spectra (COSY, HSQC, HMBC).…”

Bioactive compounds from Chrysosporium multifidum, a fungus isolated from Hermetia illucens gut microbiota

“…All the compounds (Fig 2) were identified by comparison of their spectroscopic data (HRMS and 1 H and 13 C NMR) with literature, as well as careful examination of their 2D NMR spectra (COSY, HSQC, HMBC). Optical rotations were also coherent with those published, except for ( 4 ), for which we found an optical rotation close to zero indicating the possible isolation of a racemic mixture (found [α] 20 D −4.3, c=0.16, MeOH/CH 2 Cl 2 9/1; published [α] 25 D −98.7, c=0.6, MeOH) [31].…”

“…The bioguided isolation of ethyl acetate extract prepared from the C. multifidum broth resulted in the isolation of: 4-methoxy-2H-pyran-2-one ( 1 ) [28], 4-methoxy-6-pentyl-2H-pyran-2-one ( 2 )[29], 6-(1-hydroxypentyl)-4-methoxy-pyran-2-one ( 3 ) [29, 30], 6-[(7S,8R)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one ( 4 ) [31], pestalotin ( 5 ) [32, 33], 5,6-dihydro-4-methoxy-6-(pentanoyloxy)-2H-pyran-2-one ( 6 ) [30, 33] y cyclo-(L-Pro-L-Phe) ( 7 ) [34]. All the compounds (Fig 2) were identified by comparison of their spectroscopic data (HRMS and 1 H and 13 C NMR) with literature, as well as careful examination of their 2D NMR spectra (COSY, HSQC, HMBC).…”

Two New Isocoumarin Derivatives from an Endophytic Fungi Pestalotiopsis coffeae Isolated from a Mangrove Fishtail Palm

“…The plant endophytic fungi, an outstanding source of small molecules [1], is a kind of microorganism which spend their whole or part life cycle inhabiting the normal tissues of host plants without causing apparent sick symptoms [2][3][4][5]. Fungal endophytes were isolated from tissue of numerous species, such as land plants and marine algae [6].…”