Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans

Abstract

A scale-up fermentation of the fungus Boreostereum vibrans facilitated the isolation of six new vibralactone biogenesis-associated analogues, namely vibralactamide A (1), vibralactone T (2), 13-O-lactyl vibralactone (3), 10-O-acetyl vibralactone G (4), (11R,12R)- and (11S,12R)-vibradiol (5, 6). Their structures were established via extensive spectroscopic analyses, specific optical rotation comparison, and Snatzke’s method. The biosynthetic pathway for vibralactamide A was postulated. The absolute configuration of vibralactone B was revised by single crystal X-ray diffraction analysis. This work puts the divergent vibralactone biosynthesis pathway one step further and expands the structural diversity of vibralactone-associated compounds.Graphical Abstract Electronic supplementary materialThe online version of this article (10.1007/s13659-017-0147-5) contains supplementary material, which is available to authorized users.

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

“…YMF1.1660 [ 72 ]; 4-hydroxybenzaldehyde (133) from S. insigne CGMCC5.57 [ 69 ]; erinapyrone C (134) and hericenols A-D (135-138), which possess a geranyl side chain attached to a resorcinol skeleton as a common structure, and 6-hydroxymethyl-2,2-dimethylchroman-4-one (139) from Stereum sp. 99123 [ 73 ]; 2-(3-methyl-2- buten-1-yl)-4-methoxyethyl-phenol (140), 5-hydroxy-4-(hydroxymethyl)-2-(3-methylbut-2-en-1- yl)cyclohex-4-en-1-one (141), 3-(hydroxymethyl)-4-methoxy-2-(3-methylbut-3-en-1-yn-1-yl)phenol (142), 4-methoxy-benzoic acid methyl ester (143), and niacinamide (144) from solid fermentation extracts of S. hirsutum FP-91666 [ 74 ]; (3S*,4R*)-6-acetoxymethyl-2,2-dimethyl-3,4-dihydro-2H- chromene-3,4-diol (145) and (11S,12R)-vibradiol (146) from S. vibrans [ 75 , 76 ]. 3,5-Dihydroxy-4-(3- methylbut-2-enyl) benzene-1,2-dicarbaldehyde (130) showed significant nematocidal activity against the nematode P. redivivus [ 61 ].…”

“…Later, a series of vibralactone-related compounds, vibralactones B–Q (154–169), 1,5-secovibralactone (173), and acetylated vibralactone (174) were obtained from cultures of the S. vibrans [ 75 , 89 , 90 , 91 , 92 ]. The absolute configuration of vibralactone B (154) was amended by X-ray analysis [ 76 ]. The absolute configuration of 1,5-secovibralactone (173) was suggested to be S by computational methods [ 89 ].…”

“…Vibralactone T (172), vibralactamide A (175), 13-O-lactyl vibralactone (176) and 10-O-acetyl vibralactone G (177) were obtained from the fungus S. vibrans [ 76 ]. A new vibralactone derivative, dihydro-1,5-secovibralactone (178), was isolated from Stereum sp.…”

“…Vibralactones G-J (159-162), L (164), M (165) and R (170), sharing the γ-lactone moiety, presumably derive from 1,5-seco-vibralactone by ester hydrolysis and decarboxylation. Vibralactone T (172), vibralactamide A (175), 13-O-lactyl vibralactone (176) and 10-O-acetyl vibralactone G (177) were obtained from the fungus S. vibrans [76]. A new vibralactone derivative, dihydro-1,5-secovibralactone (178), was isolated from Stereum sp.…”

Irlactane and Tremulane Sesquiterpenes from the Cultures of the Medicinal Fungus Irpex lacteus HFG1102

“…2). The remaining two methylenes was assigned to an aminoethanol group same as that harbored in vibralactamide A [8] according to the chemical shifts of C-1′ (δ C 41.3), C-2′ (δ C 60.4) and the 1 H-1 H COSY correlations between H-1′ (δ H 3.56)/H-2′ (δ H 3.63). The HMBC correlations from H-1′ to two carbonyls at C-11 and C-12, revealed a succinamide moiety.…”