Identification and Synthesis of Novel Chlorinated <i>p</i>-Anisylpropanoid Metabolites from <i>Bjerkandera</i> Species

Swarts, Hans J. M.; Verhagen, Frank J. M.; Field, Jim A.; Wijnberg, J. B. P. A.

doi:10.1021/np980164h

Cited by 17 publications

(5 citation statements)

References 22 publications

(75 reference statements)

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“…On the surfaces of decaying leaves, high aromatic Cl org concentrations have been found to coincide spatially with fungal colonies [ Leri et al , 2007]. Specific chlorinated metabolites, many of which contain aromatic Cl org functionalities, have been isolated from certain soil fungi and lichen specimens [ Gribble , 2003; Turner and Aldridge , 1983; Swarts et al , 1998; Yosioka et al , 1968], and such molecules may be incorporated into NOM through adsorption and/or humification processes. However, chloroperoxidase (CPO)‐like activity has been detected in forest soils [ Asplund et al , 1993; Latumus et al , 1995], and the organic substrates of CPO‐mediated reactions could be nonspecific.…”

Section: Resultsmentioning

confidence: 99%

Organochlorine turnover in forest ecosystems: The missing link in the terrestrial chlorine cycle

Leri¹,

Myneni²

2010

Global Biogeochemical Cycles

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Research in the last 20 years has shown that chlorine undergoes transformations between inorganic and organic forms as part of a complex biogeochemical cycle in terrestrial systems. Natural organochlorine production appears to be associated with the decomposition of plant material on the soil surface, though the chlorine cycle budget implies that a proportion of natural organochlorine enters soil through plant litter and atmospheric deposition as well. Organochlorine compounds may form through biotic and abiotic pathways, but the rates and magnitude of production in the field remain undefined. We have performed a time‐dependent trace of chlorine concentration through forest ecosystems, revealing distinct fractions of naturally produced organochlorine in plant biomass. Aliphatic organochlorine constitutes an intrinsic component of healthy leaves that persists through senescence and humification of the plant material, making a substantial contribution to the pool of soil organochlorine. Plant leaves also contain soluble aromatic organochlorine compounds that leach from leaf litter during early decay stages. As decay progresses, high concentrations of insoluble aromatic organochlorine accrue in the humus, through de novo production as well as adsorption. The rates of aromatic organochlorine production and degradation vary seasonally and conversely. This study presents the first unambiguous evidence that there exist multiple pools of chlorinated organic matter in the soil environment and that leaf litter deposition makes a significant and refractory contribution to the soil organochlorine pool, providing key insights into the biogeochemical chlorine cycle.

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Section: Resultsmentioning

confidence: 99%

Organochlorine turnover in forest ecosystems: The missing link in the terrestrial chlorine cycle

Leri¹,

Myneni²

2010

Global Biogeochemical Cycles

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“…Esto se podría explicar porque la especie de los hongos Bjerkandera puede también catalizar la reacción de clorinación de compuestos aromáticos (Swarts et al, 1998). Así, cuando el toxafeno se oxidó, los átomos de los cloruros pudieran ser liberados al medio y pudieran ser rápidamente utilizados por los hongos para clorar otras moléculas (Ilustración 5).…”

Section: Discussionunclassified

Degradación de toxafeno en medio líquido por Bjerkandera sp BOL13 utilizando diferentes sustratos

2006

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ESTE TRABAJO INVESTIGA LA DEGRADACIÓN DEL PLAGUICIDA toxafeno utilizando hongos producidos por la descomposición de la madera (white-rot fungus) Bjerkandera sp BOL13. La especie Bjerkandera sp BOL13 degradó el toxafeno al utilizar tres diferentes sustratos (virutas de madera, cáscara de trigo y melaza de caña) en medio líquido por un período de 38 días. Aproximadamente el 85% del toxafeno fue degradado cuando se utilizó la cáscara de trigo como sustrato principal. La producción de lignina peroxidasa (LiP) fue solamente estimulada cuando la cáscara de trigo estuvo presente en el medio líquido. Aunque la enzima xilanasa se encontró en todos los sustratos, la cáscara de trigo soportó la más alta producción de xilanasa. Una cantidad insignificante de ß-glucosidasa y celulasa fueron encontradas en las muestras del medio líquido. Según la literatura, éste es el primer trabajo de investigación referente a la degradación de toxafeno con hongos Bjerkandera sp producidos por la descomposición de la madera

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“…In the well-studied white rot fungus Bjerkandera adusta, compound 48 was detected after supplementation of the culture medium with p-anisaldehyde (ring 13 C 6substituted) using gas chromatography-mass spectrometry [48]. However, the main focus of these investigations was on chloroarylpropane diols, some of which had already been described in 1998 by Swarts et al for species of Bjerkandera [49]. Silk et al also detected such diols after supplementation with 13 C 9 -L-phenylalanine [50].…”

Section: Supplementation With L-tyrosine and Formation Of 2-hppmentioning

confidence: 99%

Production of an Anise- and Woodruff-like Aroma by Monokaryotic Strains of Pleurotus sapidus Grown on Citrus Side Streams

et al. 2022

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The production of natural flavors by means of microorganisms is of great interest for the food and flavor industry, and by-products of the agro-industry are particularly suitable as substrates. In the present study, Citrus side streams were fermented using monokaryotic strains of the fungus Pleurotus sapidus. Some of the cultures exhibited a pleasant smell, reminiscent of woodruff and anise, as well as herbaceous notes. To evaluate the composition of the overall aroma, liquid/liquid extracts of submerged cultures of a selected monokaryon were prepared, and the volatiles were isolated via solvent-assisted flavor evaporation. Aroma extract dilution analyses revealed p-anisaldehyde (sweetish, anisic- and woodruff-like) with a flavor dilution factor of 218 as a character impact compound. The coconut-like, herbaceous, and sweetish smelling acyloin identified as (2S)-hydroxy-1-(4-methoxyphenyl)-1-propanone also contributed to the overall aroma and was described as an aroma-active substance with an odor threshold in air of 0.2 ng L−1 to 2.4 ng L−1 for the first time. Supplementation of the culture medium with isotopically substituted l-tyrosine elucidated this phenolic amino acid as precursor of p-anisaldehyde as well as of (2S)-hydroxy-1-(4-methoxyphenyl)-1-propanone. Chiral analysis via HPLC revealed an enantiomeric excess of 97% for the isolated product produced by P. sapidus.

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Identification and Synthesis of Novel Chlorinated p-Anisylpropanoid Metabolites from Bjerkandera Species

Cited by 17 publications

References 22 publications

Organochlorine turnover in forest ecosystems: The missing link in the terrestrial chlorine cycle

Organochlorine turnover in forest ecosystems: The missing link in the terrestrial chlorine cycle

Degradación de toxafeno en medio líquido por Bjerkandera sp BOL13 utilizando diferentes sustratos

Production of an Anise- and Woodruff-like Aroma by Monokaryotic Strains of Pleurotus sapidus Grown on Citrus Side Streams

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