Studies in the usnic acid series. IX. The biodegradation of (+)-usnic acid by <i>Mucor</i><i>globosus</i>

Kutney, James P.; Leman, Jeffrey D.; Salisbury, Phillip J.; Yee, Trevor; Sánchez, I. H.

doi:10.1139/v84-056

Cited by 10 publications

(6 citation statements)

References 5 publications

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“…Compounds 6a and 6b were therefore found to have novel scaffolds. The structures of 6c – 6e were analyzed from their 1 H‐ and 13 C‐NMR spectra and by reference to the literature [17,18] …”

Section: Resultsmentioning

confidence: 99%

α‐Glucosidase Inhibition by Usnic Acid Derivatives

Nguyen

Devi

Nguyen

et al. 2021

Chemistry & Biodiversity

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This study investigated a set of new potential antidiabetes agents. Derivatives of usnic acid were designed and synthesized. These analogs and nineteen benzylidene analogs from a previous study were evaluated for enzyme inhibition of α‐glucosidase. Analogs synthesized using the Dakin oxidative method displayed stronger activity than the pristine usnic acid (IC50>200 μM). Methyl (2E,3R)‐7‐acetyl‐4,6‐dihydroxy‐2‐(2‐methoxy‐2‐oxoethylidene)‐3,5‐dimethyl‐2,3‐dihydro‐1‐benzofuran‐3‐carboxylate (6b) and 1,1′‐(2,4,6‐trihydroxy‐5‐methyl‐1,3‐phenylene)di(ethan‐1‐one) (6e) were more potent than an acarbose positive control (IC50 93.6±0.49 μM), with IC50 values of 42.6±1.30 and 90.8±0.32 μM, respectively. Most of the compounds synthesized from the benzylidene series displayed promising activity. (9bR)‐2,6‐Bis[(2E)‐3‐(2‐chlorophenyl)prop‐2‐enoyl]‐3,7,9‐trihydroxy‐8,9b‐dimethyldibenzo[b,d]furan‐1(9bH)‐one (1c), (9bR)‐3,7,9‐trihydroxy‐8,9b‐dimethyl‐2,6‐bis[(2E)‐3‐phenylprop‐2‐enoyl]dibenzo[b,d]furan‐1(9bH)‐one (1g), (9bR)‐2‐acetyl‐6‐[(2E)‐3‐(2‐chlorophenyl)prop‐2‐enoyl]‐3,7,9‐trihydroxy‐8,9b‐dimethyldibenzo[b,d]furan‐1(9bH)‐one (2d), (9bR)‐2‐acetyl‐6‐[(2E)‐3‐(3‐chlorophenyl)prop‐2‐enoyl]‐3,7,9‐trihydroxy‐8,9b‐dimethyldibenzo[b,d]furan‐1(9bH)‐one (2e), (6bR)‐8‐acetyl‐3‐(4‐chlorophenyl)‐6,9‐dihydroxy‐5,6b‐dimethyl‐2,3‐dihydro‐1H‐[1]benzofuro[2,3‐f][1]benzopyran‐1,7(6bH)‐dione (3e), (6bR)‐8‐acetyl‐6,9‐dihydroxy‐5,6b‐dimethyl‐3‐phenyl‐2,3‐dihydro‐1H‐[1]benzofuro[2,3‐f][1]benzopyran‐1,7(6bH)‐dione (3h), (6bR)‐3‐(2‐chlorophenyl)‐8‐[(2E)‐3‐(2‐chlorophenyl)prop‐2‐enoyl]‐6,9‐dihydroxy‐5,6b‐dimethyl‐2,3‐dihydro‐1H‐[1]benzofuro[2,3‐f][1]benzopyran‐1,7(6bH)‐dione (4b), and (9bR)‐6‐acetyl‐3,7,9‐trihydroxy‐8,9b‐dimethyl‐2‐[(2E)‐3‐phenylprop‐2‐enoyl]dibenzo[b,d]furan‐1(9bH)‐one (5c) were the most potent α‐glucosidase enzyme inhibitors, with IC50 values of 7.0±0.24, 15.5±0.49, 7.5±0.92, 10.9±0.56, 1.5±0.62, 15.3±0.54, 19.0±1.00, and 12.3±0.53 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

α‐Glucosidase Inhibition by Usnic Acid Derivatives

Nguyen

Devi

Nguyen

et al. 2021

Chemistry & Biodiversity

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“…1977b), the saprophytic fungi Mortierella (Bandoni & Towers 1967; Kutney et al . 1977a, 1984) and Mucor (Kutney et al . 1984) have the capacity to degrade (+)‐usnic acid.…”

Section: Discussionmentioning

confidence: 99%

“…Should usnic acid enter the soil in lichen fragments, however, it would be degraded in soil either through microbial degradation or chemical breakdown. Various micro-organisms, such as pseudomonad bacteria (Bandoni & Towers 1967;Kutney et al 1977b), the saprophytic fungi Mortierella (Bandoni & Towers 1967;Kutney et al 1977aKutney et al , 1984 and Mucor (Kutney et al 1984) have the capacity to degrade (+)-usnic acid. The Table 1.…”

Section: Discussionmentioning

confidence: 99%

No allelopathic effect of the dominant forest‐floor lichen Cladonia stellaris on pine seedlings

Kytöviita

Stark²

2009

Functional Ecology

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Summary 1.The lichen Cladonia stellaris forms dense mats and dominates the forest-floor vegetation in latesuccessional oligotrophic boreal forests. This lichen is rich in polyphenolic secondary compounds, and through allelochemical effects of these compounds the dense mat formed by C . stellaris is assumed to have negative effect on forest regeneration and soil microbial functioning. 2. We examined the effect of C . stellaris and its secondary metabolite usnic acid on nutrient uptake and growth of pine ( Pinus sylvestris ) seedlings in symbiosis with the ectomycorrhizal fungus Suillus variegatus and in non-symbiotic condition. 3. Contrary to our expectations, usnic acid had no effect on nitrogen uptake and growth in pine seedlings. The addition of lichen fragments into the growth substrate significantly increased biomass accumulation in mycorrhizal pine seedlings and needle nitrogen acquisition in nonmycorrhizal seedlings. 4. These results suggest that lichen mats do not have direct allelopathic effects on pine seedling nitrogen acquisition or growth.

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“…Laboratory studies have shown that the bacteria Pseudomonas sp. (Kutney, Leman et al 1977), the mould fungus Mucor globosus (Kutney et al 1984) and the soil fungus Mortierella isabellina (Kutney, Baarschers et al 1977) can take part in the decomposition of usnic acid derivatives.…”

Section: Introductionmentioning

confidence: 99%