Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides

dc.contributor.author Crispin, Matthew
dc.contributor.author Hur, Manhoi
dc.contributor.author Park, Taeseong
dc.contributor.author Kim, Young Hwan
dc.contributor.author Wurtele, Eve
dc.contributor.department Genetics, Development and Cell Biology
dc.date 2018-02-18T04:17:20.000
dc.date.accessioned 2020-06-30T04:02:43Z
dc.date.available 2020-06-30T04:02:43Z
dc.date.copyright Tue Jan 01 00:00:00 UTC 2013
dc.date.issued 2013-07-01
dc.description.abstract <p>Species of the genus Hypericum contain a rich array of unusual polyketides, however, only a small proportion of the over 450 Hypericum species, other than the popular medicinal supplement St. John’s Wort (H. perforatum), have even been chemically characterized. H. gentianoides, a small annual used medicinally by Cherokee Americans, contains bioactive acylphloroglucinols. Here, we identify acylphloroglucinol constituents of H. gentianoides and determine a potential pathway to their synthesis. Liquid chromatography/electrospray ionization-mass spectrometry (LC/ESIMS) and HPLC-UV indicate that the level of accumulation and profile of acylphloroglucinols in H. gentianoides vary little seasonally when grown in a greenhouse, but do vary with development and are highly dependent on the accession, highlighting the importance of the selection of plant material for study. We identify the chemical structures of the nine prevalent polyketides, based on LC/ESI-MS and hybrid quadrupole orthogonal time-of-flight mass (Q-TOF) spectrometry; these metabolites include one monomeric phlorisobutyrophenone (PIB) derivative and eight dimeric acylphloroglucinols. Q-TOF spectrometry was used to identify eight additional PIB derivatives that were not detected by LC/ESI-MS. These data lead us to propose that diacylphloroglucinols are synthesized via modification of PIB to yield diverse phloroglucinol and filicinic acids moieties, followed by dimerization of a phloroglucinol and a filicinic acid monomer to yield the observed complement of diacylphloroglucinols. The metabolomics data from H. gentianoides are accessible in PMR (http://www.metnetdb.org/pmr), a public metabolomics database with analysis software for plants and microbial organisms.</p>
dc.description.comments <p>This is the peer reviewed version of the following article: Crispin, M. C., Hur, M., Park, T., Kim, Y. H. and Wurtele, E. S. (2013), Identification and biosynthesis of acylphloroglucinols in <em>Hypericum gentianoides</em>. Physiol Plantarum, 148: 354–370, which has been published in final form at doi: <a href="http://dx.doi.org/10.1111/ppl.12063" target="_blank">10.1111/ppl.12063</a>. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/gdcb_las_pubs/70/
dc.identifier.articleid 1072
dc.identifier.contextkey 9650110
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath gdcb_las_pubs/70
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/37982
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/gdcb_las_pubs/70/2013_Wurtle_IdentificationBiosynthesis.pdf|||Sat Jan 15 01:40:25 UTC 2022
dc.source.uri 10.1111/ppl.12063
dc.subject.disciplines Botany
dc.subject.disciplines Cell and Developmental Biology
dc.subject.disciplines Genetics
dc.title Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication a7de6326-d86c-4395-b9e6-51187c7f1782
relation.isOrgUnitOfPublication 9e603b30-6443-4b8e-aff5-57de4a7e4cb2
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