3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis

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Abstract

Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood. Eleven dihydroflavonols were isolated from propolis collected in Fallon, NV, including pinobanksin-3-octanoate. This hitherto unknown derivative and five other 3-acyl-dihydroflavonols showed inhibitory activity against both P. larvae (IC50 = 17–68 μM) and Ascosphaera apis (IC50 = 8–23 μM), the fungal agent of chalkbrood. A structure-activity relationship between acyl group size and antimicrobial activity was found, with longer acyl groups increasing activity against P. larvae and shorter acyl groups increasing activity against A. apis. Finally, it was determined that the isolated 3-acyl-dihydroflavonols originated from Populus fremontii, and further analysis showed these compounds can also be found in other North American Populus spp.

Original languageEnglish (US)
Pages (from-to)83-92
Number of pages10
JournalPhytochemistry
Volume138
DOIs
StatePublished - Jun 1 2017

Fingerprint

propolis
Paenibacillus
Honey
Bees
Larva
Propolis
Paenibacillus larvae
Ascosphaera apis
Apoidea
resins
honey bees
antimicrobial agents
pathogens
Inborn Errors Amino Acid Metabolism
Pathogens
Populus
Populus fremontii
chalk brood
American foul brood
beekeepers

Keywords

  • Antimicrobial activity
  • Ascospharea apis
  • Dihydroflavonol
  • Honey bees (Apis mellifera)
  • Paenibacillus larvae
  • Plant resins
  • Populus
  • Propolis
  • Salicaceae

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

MeSH PubMed subject areas

  • Journal Article

Cite this

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title = "3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis",
abstract = "Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood. Eleven dihydroflavonols were isolated from propolis collected in Fallon, NV, including pinobanksin-3-octanoate. This hitherto unknown derivative and five other 3-acyl-dihydroflavonols showed inhibitory activity against both P. larvae (IC50 = 17–68 μM) and Ascosphaera apis (IC50 = 8–23 μM), the fungal agent of chalkbrood. A structure-activity relationship between acyl group size and antimicrobial activity was found, with longer acyl groups increasing activity against P. larvae and shorter acyl groups increasing activity against A. apis. Finally, it was determined that the isolated 3-acyl-dihydroflavonols originated from Populus fremontii, and further analysis showed these compounds can also be found in other North American Populus spp.",
keywords = "Antimicrobial activity, Ascospharea apis, Dihydroflavonol, Honey bees (Apis mellifera), Paenibacillus larvae, Plant resins, Populus, Propolis, Salicaceae",
author = "Wilson, {Michael B.} and Pawlus, {Alison D.} and Doug Brinkman and Gary Gardner and Hegeman, {Adrian D.} and Marla Spivak and Cohen, {Jerry D.}",
year = "2017",
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volume = "138",
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journal = "Phytochemistry",
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T1 - 3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis

AU - Wilson,Michael B.

AU - Pawlus,Alison D.

AU - Brinkman,Doug

AU - Gardner,Gary

AU - Hegeman,Adrian D.

AU - Spivak,Marla

AU - Cohen,Jerry D.

PY - 2017/6/1

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