AI Article Synopsis

  • Two new compounds, Talaromycin A and Talaromycin B, were discovered from a liquid culture and their structures were determined using various spectroscopic methods.
  • Known compounds were also isolated during the study.
  • When tested for specific inhibitory activities (monoamine oxidase, acetylcholinesterase, and PI3K), the newly discovered compounds showed only weak effects.

Article Abstract

Two new compounds Talaromycin A () and Talaromycin B () were isolated from a liquid culture of The structures of and were elucidated by IR, MS, 1D and 2D NMR spectra and comparison of the experimental and calculated electronic circular dichroism spectra. Additional known compounds () were also isolated. These compounds were tested for monoamine oxidase, acetylcholinesterase and PI3K inhibitory activity, but showed only weak activity.

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http://dx.doi.org/10.1080/14786419.2019.1593163DOI Listing

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Article Synopsis
  • Two new compounds, Talaromycin A and Talaromycin B, were discovered from a liquid culture and their structures were determined using various spectroscopic methods.
  • Known compounds were also isolated during the study.
  • When tested for specific inhibitory activities (monoamine oxidase, acetylcholinesterase, and PI3K), the newly discovered compounds showed only weak effects.
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The active metabolites investigation of Talaromyces sp. (strain No. MH551540) associated with Xanthoparmelia angustiphylla afforded one new δ-lactone, talaromycin A (1), together with six known compounds, clearanol A (2), 6-methylbiphenyl-3,3',4,5'-tetraol (3), desmethylaltenusin (4), ergone (5), ergosterol (6), and palmitic acid (7).

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Bioactive diphenyl ether derivatives from a gorgonian-derived fungus Talaromyces sp.

Chem Biodivers

March 2015

Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China, (phone/fax: +86-532-82031536).

Three new diphenyl ether derivatives, talaromycins A-C (1-3, resp.), together with six known analogs, 4-9, were isolated from a gorgonian-derived fungus, Talaromyces sp. The structures of the new compounds were determined by analysis of extensive NMR spectroscopic data.

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Hetero-Diels-Alder reaction of the steroidal exocyclic enol ethers 14 and 15, obtained from the secoestrones 8 and 9 by reduction, iodoetherification, and elimination, with ethyl O-benzoyldiformylacetate (16) leads to the spiroacetals 17 and 18 as a mixture of four diastereomers. Reduction of the major diastereomers 17a and 18a with DIBAH and subsequent hydrogenation yields the novel natural product hybrids 21, 23, 24, and 25, which possess the structural features of the steroid estrone (7) and the mycotoxin talaromycin 6.

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Numerous pharmacologically interesting compounds are available by the synthesis of hybrid natural products. Thus, for instance, the estrone-talaromycin hybrid 2, which is synthesized in a few steps from the estrone derivative 1 by a sequence in which a hetero-Diels-Alder reaction is the key step, exhibits notable cytotoxic activity.

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