Beauvetetraones A-C, phomaligadione-derived polyketide dimers from the entomopathogenic fungus, Beauveria bassiana

Seoung Rak Lee; Michelle Küfner; Minji Park; Won Hee Jung; Sang Un Choi; Christine Beemelmanns; Ki Hyun Kim

doi:10.1039/c8qo01009a

Beauvetetraones A-C, phomaligadione-derived polyketide dimers from the entomopathogenic fungus, Beauveria bassiana

Seoung Rak Lee
, Michelle Küfner
, Minji Park
, Won Hee Jung
, Sang Un Choi
, Christine Beemelmanns
, Ki Hyun Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

We report the isolation of two novel epimeric phomaligadione-derived polyketides, beauvetetraones A-B (1-2), from the entomopathogenic fungus Beauveria bassiana. Beauvetetraones A and B feature an unprecedented methylene-bridged phloroglucinol skeleton with a highly rearranged scaffold. In addition, a dimer of two phomaligadiones, named beauvetetraone C, was isolated for the first time from a natural source. The structures of compounds 1-3 including their absolute configurations were unambiguously assigned by NMR spectroscopic analyses, phenylglycine methyl ester (PGME) analysis, and quantum chemical ECD calculations. A putative biosynthetic pathway for beauvetetraones A-C is proposed.

Original language	English
Pages (from-to)	162-166
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	2
DOIs	https://doi.org/10.1039/c8qo01009a
State	Published - 21 Jan 2019

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title = "Beauvetetraones A-C, phomaligadione-derived polyketide dimers from the entomopathogenic fungus, Beauveria bassiana",

abstract = "We report the isolation of two novel epimeric phomaligadione-derived polyketides, beauvetetraones A-B (1-2), from the entomopathogenic fungus Beauveria bassiana. Beauvetetraones A and B feature an unprecedented methylene-bridged phloroglucinol skeleton with a highly rearranged scaffold. In addition, a dimer of two phomaligadiones, named beauvetetraone C, was isolated for the first time from a natural source. The structures of compounds 1-3 including their absolute configurations were unambiguously assigned by NMR spectroscopic analyses, phenylglycine methyl ester (PGME) analysis, and quantum chemical ECD calculations. A putative biosynthetic pathway for beauvetetraones A-C is proposed.",

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doi = "10.1039/c8qo01009a",

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T1 - Beauvetetraones A-C, phomaligadione-derived polyketide dimers from the entomopathogenic fungus, Beauveria bassiana

AU - Lee, Seoung Rak

AU - Küfner, Michelle

AU - Park, Minji

AU - Jung, Won Hee

AU - Choi, Sang Un

AU - Beemelmanns, Christine

AU - Kim, Ki Hyun

PY - 2019/1/21

Y1 - 2019/1/21

N2 - We report the isolation of two novel epimeric phomaligadione-derived polyketides, beauvetetraones A-B (1-2), from the entomopathogenic fungus Beauveria bassiana. Beauvetetraones A and B feature an unprecedented methylene-bridged phloroglucinol skeleton with a highly rearranged scaffold. In addition, a dimer of two phomaligadiones, named beauvetetraone C, was isolated for the first time from a natural source. The structures of compounds 1-3 including their absolute configurations were unambiguously assigned by NMR spectroscopic analyses, phenylglycine methyl ester (PGME) analysis, and quantum chemical ECD calculations. A putative biosynthetic pathway for beauvetetraones A-C is proposed.

AB - We report the isolation of two novel epimeric phomaligadione-derived polyketides, beauvetetraones A-B (1-2), from the entomopathogenic fungus Beauveria bassiana. Beauvetetraones A and B feature an unprecedented methylene-bridged phloroglucinol skeleton with a highly rearranged scaffold. In addition, a dimer of two phomaligadiones, named beauvetetraone C, was isolated for the first time from a natural source. The structures of compounds 1-3 including their absolute configurations were unambiguously assigned by NMR spectroscopic analyses, phenylglycine methyl ester (PGME) analysis, and quantum chemical ECD calculations. A putative biosynthetic pathway for beauvetetraones A-C is proposed.

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U2 - 10.1039/c8qo01009a

DO - 10.1039/c8qo01009a

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JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 2

ER -

Beauvetetraones A-C, phomaligadione-derived polyketide dimers from the entomopathogenic fungus, Beauveria bassiana

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