Fungal Biotransformation Products of Dehydroabietic Acid

Abstract

Dehydroabietic acid (DHA) (1) is one of the main compounds in Scots pine wood responsible for aquatic and microbial toxicity. The degradation of 1 by Trametes versicolor and Phlebiopsis gigantea in liquid stationary cultures was followed by HPLC-DAD-ELSD. Both fungi rapidly degraded DHA relative to a control. More breakdown products were observed for T. versicolor than for P. gigantea. After 13 days, four compounds were identified by means of spectroscopic methods in P. gigantea cultures: 1beta-hydroxy-DHA (2), 1beta,7alpha-dihydroxy-DHA (3), 1beta,16-dihydroxy-DHA (5), and tentatively 1beta-hydroxy-7-oxo-DHA (4). In T. versicolor cultures, 1beta,16-dihydroxy-DHA (5), 7beta,16-dihydroxy-DHA (6), 1beta,7beta,16-trihydroxy-DHA (7), 1beta,16-dihydroxy-7-oxo-DHA (8), 1beta,15-dihydroxy-DHA (9), and 1beta,7alpha,16-trihydroxy-DHA (10) were identified after 9 days of incubation. Thus the biotransformation of 1 by the two fungi was different, with only 5 being produced by both strains. Compounds 3, 7, 8, and 10 are reported for the first time as natural products.

Pollutants Biodegradation by Fungi

“…Moreover, van Beek et al [77] reported the degradation of dehydroabietic acid (DHA) (6) from Scots pine wood by Trametes versicolor and Phlebiopsis gigantea in liquid stationary cultures, isolating some biodegradation products from P. gigantea cultures: 1 -hydroxy-DHA (7), 1 ,7 -dihydroxy-DHA (8), 1 ,16-dihydroxy-DHA (9), and tentatively 1 -hydroxy-7-oxo-DHA (10) dihydroxy-DHA (9), 7 ,16-dihydroxy-DHA (11), 1 ,7 ,16-trihydroxy-DHA (12), 1 ,16-dihydroxy-7-oxo-DHA (13), 1 ,15-dihydroxy-DHA (14), and 1 ,7 ,16-trihydroxy-DHA (15) (Scheme 2). Also, Candida tropicalis was tested on the reduction of free gossypol (16), a polyphenol derived from the cotton plant.…”

“…For instance, Irpex lacteus was used for mutagenicity assays showing that all dyes except Congo Red (CR) (74) were mutagenic, indicating that the combined biodegradation process may be useful for reducing the mutagenicity associated with wastewater from textile industries [189]. The biodegradation of Methyl Orange (75), Yellow RR Gran, Congo Red (74), Bismarck Brown (76), Brilliant Red K-2BP (77), and the azo dye Remazol Red RR Gran in cultures of the white rot fungus Phaenerochaete chrysosporium was demonstrated by decolourization studies [190,191,192,193]. Moreover, the ability to decolourize eight chemically different synthetic dyes (Orange G (78), Amaranth (79), Orange I (80), Remazol Brilliant Blue R (RBBR) (73), Cuphthalocyanin, Poly R-478 (81), Malachite Green (71) and Crystal Violet (70)) by the white rot fungus Dichomitus squalens was evaluated showing high decolourization capacity for all dyes tested, but not to the same extent [194].…”

Analysis of Fuzhisan and quantitation of baicalin and ginsenoside Rb1 by HPLC-DAD-ELSD

“…The combined use of HPLC-DAD-ELSD has been shown to be suitable for detection of the multiple and complex analytes in TCM (Wei et al, 2007;van Nederkassel et al, 2005;Shao and Cheng, 2006;Qi et al, 2008;Yu et al, 2007;van Beek et al, 2007). Previous research confirmed that chromatographic fingerprinting coupled with principal component analysis would be a critical strategy to comprehensively control the quality of the combined TCM formula (Chen et al, 2007;Li et al, 2007;Qi et al, 2006).…”

Aromatic abietane diterpenoids: total syntheses and synthetic studies

“…4 Some abietanes have also been isolated from fungal species. 9 To date, there are around two hundred known compounds belonging to this group of natural products, commonly known as dehydroabietic derivatives (dehydroabietanes). Generally, aromatic abietanes are not functionalised on A-ring carbons.…”

“…2). Other are obtained directly from natural sources as for example, abieta-8,11,13-triene (8), trans-communic acid (9), pisiferic acid (10) and callitrisic acid (4) (Fig. 2).…”