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Article: In vivo transformations of dihydro-epi-deoxyarteannuin B in Artemisia annua plants

TitleIn vivo transformations of dihydro-epi-deoxyarteannuin B 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. 9536-9547 How to Cite?
Abstract[15-13C2H3]-dihydro-epi-deoxyarteannuin B (4a) has been fed to intact Artemisia annua plants via the root and three labeled metabolites (17a-19a) have been identified by 1D- and 2D-NMR spectroscopies. The in vivo transformations of 4a in A. annua are proposed to involve enzymatically-mediated processes in addition to possible spontaneous autoxidation. In the hypothetical spontaneous autoxidation pathway, the tri-substituted double bond in 4a appears to have undergone 'ene-type' reaction with oxygen to form an allylic hydroperoxide, which subsequently rearranges to the allylic hydroxyl group in the metabolite 3α-hydroxy-dihydro-epi-deoxyarteannuin B (17a). In the enzymatically-mediated pathways, compound 17a has then been converted to its acetyl derivative, 3α-acetoxy-dihydro-epi-deoxyarteannuin B (18a), while oxidation of 4a at the 'unactivated' 9-position has yielded 9β-hydroxy-dihydro-epi-deoxyarteannuin B (19a). Although all of the natural products artemisinin (1), arteannuin K (7), arteannuin L (8), and arteannuin M (9) have been suggested previously as hypothetical metabolites from dihydro-epi-deoxyarteannuin B in A. annua, none were isolated in labeled form in this study. It is argued that the nature of the transformations undergone by compound 4a are more consistent with a degradative metabolism, designed to eliminate this compound from the plant, rather than with a role as a late precursor in the biosynthesis of artemisinin or other natural products from A. annua. © 2007 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/168131
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. 9536-9547en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttp://hdl.handle.net/10722/168131-
dc.description.abstract[15-13C2H3]-dihydro-epi-deoxyarteannuin B (4a) has been fed to intact Artemisia annua plants via the root and three labeled metabolites (17a-19a) have been identified by 1D- and 2D-NMR spectroscopies. The in vivo transformations of 4a in A. annua are proposed to involve enzymatically-mediated processes in addition to possible spontaneous autoxidation. In the hypothetical spontaneous autoxidation pathway, the tri-substituted double bond in 4a appears to have undergone 'ene-type' reaction with oxygen to form an allylic hydroperoxide, which subsequently rearranges to the allylic hydroxyl group in the metabolite 3α-hydroxy-dihydro-epi-deoxyarteannuin B (17a). In the enzymatically-mediated pathways, compound 17a has then been converted to its acetyl derivative, 3α-acetoxy-dihydro-epi-deoxyarteannuin B (18a), while oxidation of 4a at the 'unactivated' 9-position has yielded 9β-hydroxy-dihydro-epi-deoxyarteannuin B (19a). Although all of the natural products artemisinin (1), arteannuin K (7), arteannuin L (8), and arteannuin M (9) have been suggested previously as hypothetical metabolites from dihydro-epi-deoxyarteannuin B in A. annua, none were isolated in labeled form in this study. It is argued that the nature of the transformations undergone by compound 4a are more consistent with a degradative metabolism, designed to eliminate this compound from the plant, rather than with a role as a late precursor in the biosynthesis of artemisinin or other natural products from A. annua. © 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 dihydro-epi-deoxyarteannuin B 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.2007.06.016en_US
dc.identifier.scopuseid_2-s2.0-34547656015en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-34547656015&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume63en_US
dc.identifier.issue38en_US
dc.identifier.spage9536en_US
dc.identifier.epage9547en_US
dc.identifier.isiWOS:000252091900029-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridBrown, GD=7406468149en_US
dc.identifier.scopusauthoridSy, LK=35874602700en_US

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