• Title/Summary/Keyword: pyrone

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CONFORMATIONAL ANALYSIS ON THE C$_4$-PHOTOCYCLODIMERS OF 4,$5^1$,8-TRIMETHYLPSORALEN

  • Kim, Ja-Hong
    • Journal of Photoscience
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    • v.2 no.2
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    • pp.99-101
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    • 1995
  • A semiempirical methods(PM3-CI-UHF, MM2) for the evaluation of ground and excited state electronic structures of electron-donating substituents are applied to 4, 5', 8-trimethylpsoralen(TMP) with TMP dimer. Three types of product have been proposed; (1) pyrone< >pyrone, (2) pyrone< >furan, (3) hetero dimer resulting from the C$_4$-cycloaddition between the furan end of one TMP moiety and the pyrone end of the other, with cis-syn configuration.

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Total Synthesis of (±)-Aspidospermidine Starting from 3-Ethyl-5-bromo-2-pyrone

  • Cho, Hyun-Kyu;Tam, Nguyen Thanh;Cho, Cheon-Gyu
    • Bulletin of the Korean Chemical Society
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    • v.31 no.11
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    • pp.3382-3384
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    • 2010
  • A new synthetic route to ($\pm$)-aspidospermidine was devised, starting from the cycloadduct of 3-ethyl-5-bromo-2-pyrone with vinyl sulfide through a tandem conjugate addition-alkylation sequence. The requisite 3-ethyl-5-bromo-2-pyrone was prepared via the C3-selective Pd-catalyzed coupling reaction with $Et_3Al$-dimethylaminoethanol complex.

Building Triketide α-Pyrone-Producing Yeast Platform Using Heterologous Expression of Sporopollenin Biosynthetic Genes

  • Kim, Sung Soo
    • Journal of Microbiology and Biotechnology
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    • v.25 no.11
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    • pp.1796-1800
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    • 2015
  • Sporopollenin is a poorly characterized mixed aliphatic and aromatic polymer with ester and ether linkages. Recent studies have reported that α-pyrone polyketide compounds generated by Arabidopsis thaliana, polyketide synthase A (PKSA) and tetraketide α-pyrone reductase 1 (TKPR1), are previously unknown sporopollenin precursors. Here, the yeast Saccharomyces cerevisiae was introduced to test potential sporopollenin biosynthetic pathways in vivo. A PKSA/TKPR1 dual expressor was generated and various chain-length alkyl α-pyrones were identified by GC-MS. The growth rate of the strain containing PKSA/TKPR1 appeared normal. These results indicate that PKSA/TKPR1-expressing yeast would be a starting platform to investigate in vivo sporopollenin metabolism.

Violapyrone J, α-Pyrone Derivative from a Marine-derived Actinomycetes, Streptomyces sp.

  • Leutou, Alain S.;Yang, Inho;Seong, Chi Nam;Ko, Jaeyoung;Nam, Sang-Jip
    • Natural Product Sciences
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    • v.21 no.4
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    • pp.248-250
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    • 2015
  • A new ${\alpha}-pyrone$ derivative, violapyrone J (1), and along with the two known violapyrones B (2) and C (3) were isolated from the fermentation broth of a marine actinomycete Streptomyces sp. SC0718. The structure of violapyrone J (1) was elucidated from 1D and 2D NMR spectroscopic analyses.

Microbial Metabolism of Yangonin, a Styryl Lactone from Piper methysticum (Kava)

  • Kim, Ji-Hye;Kim, Hyun-Jung;Lee, Ik-Soo
    • Natural Product Sciences
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    • v.16 no.3
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    • pp.148-152
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    • 2010
  • Microbial metabolism studies of yangonin (1), a major styryl lactone from Piper methysticum, have resulted in the production of three hydroxylated metabolites (2-4). The chemical structures of these compounds were elucidated to be 4-methoxy-6-(12-hydroxystyryl)-2-pyrone (2),4-methoxy-6-(11,12-dihydroxystyryl)-2-pyrone (3),and 4,12-dimethoxy-6-(7,8-dihydroxy-7,8-dihydrostyryl)-2-pyrone (4) on the basis of the chemical and spectroscopic analyses. The compounds 3 and 4 are reported herein as microbial metabolites of yangonin for the first time.