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Article: In vivo transformations of artemisinic acid in Artemisia annua plants

TitleIn vivo transformations of artemisinic acid in Artemisia annua plants
Authors
KeywordsAutoxidation
Biogenesis
Nmr
Terpenes And Terpenoids
Issue Date2007
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2007, v. 63 n. 38, p. 9548-9566 How to Cite?
AbstractArtemisinic acid labeled with both 13C and 2H at the 15-position has been fed to intact plants of Artemisia annua via the cut stem, and its in vivo transformations studied by 1D- and 2D-NMR spectroscopy. Seven labeled metabolites have been isolated, all of which are known as natural products from this species. The transformations of artemisinic acid-as observed both for a group of plants, which was kept alive by hydroponic administration of water and for a group, which was allowed to die by desiccation-closely paralleled those, which have been recently described for its 11,13-dihydro analog, dihydroartemisinic acid. It seems likely therefore that similar mechanisms, involving spontaneous autoxidation of the Δ4,5 double bond in both artemisinic acid and dihydroartemisinic acid and subsequent rearrangements of the resultant allylic hydroperoxides, may be involved in the biological transformations, which are undergone by both compounds. All of the sesquiterpene metabolites, which were obtained from in vivo transformations of artemisinic acid retained their unsaturation at the 11,13-position, and there was no evidence for conversion into any 11,13-dihydro metabolite, including artemisinin, the antimalarial drug, which is produced by A. annua. This observation led to the proposal of a unified biosynthetic scheme, which accounts for the biogenesis of many of the amorphane and cadinane sesquiterpenes that have been isolated as natural products from A. annua. In this scheme, there is a bifurcation in the biosynthetic pathway starting from amorpha-4,11-diene leading to either artemisinic acid or dihydroartemisinic acid; these two committed precursors are then, respectively, the parents for the two large families of highly oxygenated 11,13-dehydro and 11,13-dihydro sesquiterpene metabolites, which are known from this species. © 2007 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/168132
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorBrown, GDen_US
dc.contributor.authorSy, LKen_US
dc.date.accessioned2012-10-08T03:15:28Z-
dc.date.available2012-10-08T03:15:28Z-
dc.date.issued2007en_US
dc.identifier.citationTetrahedron, 2007, v. 63 n. 38, p. 9548-9566en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttp://hdl.handle.net/10722/168132-
dc.description.abstractArtemisinic acid labeled with both 13C and 2H at the 15-position has been fed to intact plants of Artemisia annua via the cut stem, and its in vivo transformations studied by 1D- and 2D-NMR spectroscopy. Seven labeled metabolites have been isolated, all of which are known as natural products from this species. The transformations of artemisinic acid-as observed both for a group of plants, which was kept alive by hydroponic administration of water and for a group, which was allowed to die by desiccation-closely paralleled those, which have been recently described for its 11,13-dihydro analog, dihydroartemisinic acid. It seems likely therefore that similar mechanisms, involving spontaneous autoxidation of the Δ4,5 double bond in both artemisinic acid and dihydroartemisinic acid and subsequent rearrangements of the resultant allylic hydroperoxides, may be involved in the biological transformations, which are undergone by both compounds. All of the sesquiterpene metabolites, which were obtained from in vivo transformations of artemisinic acid retained their unsaturation at the 11,13-position, and there was no evidence for conversion into any 11,13-dihydro metabolite, including artemisinin, the antimalarial drug, which is produced by A. annua. This observation led to the proposal of a unified biosynthetic scheme, which accounts for the biogenesis of many of the amorphane and cadinane sesquiterpenes that have been isolated as natural products from A. annua. In this scheme, there is a bifurcation in the biosynthetic pathway starting from amorpha-4,11-diene leading to either artemisinic acid or dihydroartemisinic acid; these two committed precursors are then, respectively, the parents for the two large families of highly oxygenated 11,13-dehydro and 11,13-dihydro sesquiterpene metabolites, which are known from this species. © 2007 Elsevier Ltd. All rights reserved.en_US
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_US
dc.relation.ispartofTetrahedronen_US
dc.subjectAutoxidationen_US
dc.subjectBiogenesisen_US
dc.subjectNmren_US
dc.subjectTerpenes And Terpenoidsen_US
dc.titleIn vivo transformations of artemisinic acid in Artemisia annua plantsen_US
dc.typeArticleen_US
dc.identifier.emailSy, LK:sylk@hkucc.hku.hken_US
dc.identifier.authoritySy, LK=rp00784en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/j.tet.2007.06.062en_US
dc.identifier.scopuseid_2-s2.0-34547699424en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-34547699424&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume63en_US
dc.identifier.issue38en_US
dc.identifier.spage9548en_US
dc.identifier.epage9566en_US
dc.identifier.isiWOS:000252091900030-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridBrown, GD=7406468149en_US
dc.identifier.scopusauthoridSy, LK=35874602700en_US

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