Xylaria arbuscula was collected from a “Cypress” tree, Cupressus lusitanica. The whole cells of this endophytic fungus were used in screening for microbial bioreduction of aryl acids. Different p-substituted benzoic acids were evaluated. However, only p-bromobenzoic acid, p-chlorobenzoic acid and p-nitrobenzoic acid were converted to their corresponding alcohols. Aryl acid metabolism of X. arbuscula included GABA incorporation and glycosylation when the substrates were p-bromobenzoic and p-chlorobenzoic acids were also observed. The substrates p-hydroxybenzoic and p-aminobenzoic acids were not transformed. These results could suggest that electron-withdrawing groups at para orientation activate the substrate for reduction.

glycosylation, Xylaria arbuscula, aromatic carboxylic acid reduction, GABA, amino acid conjugation

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
7	aDGlcp	99.4	73.5	75.1	71.8	74.0	62.7
	Subst


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
7	aDGlcp	4.80	3.32	3.57	3.20	3.50	3.56-3.70
	Subst	-	7.49	7.35	-	7.35	7.49	4.50-4.69


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
7	aDGlcp	99.4/4.80	73.5/3.32	75.1/3.57	71.8/3.20	74.0/3.50	62.7/3.56-3.70
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

OC[C@H]1O[C@H](OCc2ccc(Br)cc2)[C@H](O)[C@@H](O)[C@@H]1O

349.177 g/mol (C₁₃H₁₇BrO₆)

Xylaria arbuscula was collected from a “Cypress” tree, Cupressus lusitanica. The whole cells of this endophytic fungus were used in screening for microbial bioreduction of aryl acids. Different p-substituted benzoic acids were evaluated. However, only p-bromobenzoic acid, p-chlorobenzoic acid and p-nitrobenzoic acid were converted to their corresponding alcohols. Aryl acid metabolism of X. arbuscula included GABA incorporation and glycosylation when the substrates were p-bromobenzoic and p-chlorobenzoic acids were also observed. The substrates p-hydroxybenzoic and p-aminobenzoic acids were not transformed. These results could suggest that electron-withdrawing groups at para orientation activate the substrate for reduction.

glycosylation, Xylaria arbuscula, aromatic carboxylic acid reduction, GABA, amino acid conjugation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

OC[C@H]1O[C@H](OCc2ccc(Cl)cc2)[C@H](O)[C@@H](O)[C@@H]1O

304.726 g/mol (C₁₃H₁₇ClO₆)