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Article: In vivo transformations of dihydro-epi-deoxyarteannuin B in Artemisia annua plants
Title | In vivo transformations of dihydro-epi-deoxyarteannuin B in Artemisia annua plants |
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Authors | |
Keywords | Autoxidation Biogenesis Nmr Terpenes And Terpenoids |
Issue Date | 2007 |
Publisher | Pergamon. 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 Identifier | http://hdl.handle.net/10722/168131 |
ISSN | 2023 Impact Factor: 2.1 2023 SCImago Journal Rankings: 0.406 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Brown, GD | en_US |
dc.contributor.author | Sy, LK | en_US |
dc.date.accessioned | 2012-10-08T03:15:28Z | - |
dc.date.available | 2012-10-08T03:15:28Z | - |
dc.date.issued | 2007 | en_US |
dc.identifier.citation | Tetrahedron, 2007, v. 63 n. 38, p. 9536-9547 | en_US |
dc.identifier.issn | 0040-4020 | en_US |
dc.identifier.uri | http://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.language | eng | en_US |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet | en_US |
dc.relation.ispartof | Tetrahedron | en_US |
dc.subject | Autoxidation | en_US |
dc.subject | Biogenesis | en_US |
dc.subject | Nmr | en_US |
dc.subject | Terpenes And Terpenoids | en_US |
dc.title | In vivo transformations of dihydro-epi-deoxyarteannuin B in Artemisia annua plants | en_US |
dc.type | Article | en_US |
dc.identifier.email | Sy, LK:sylk@hkucc.hku.hk | en_US |
dc.identifier.authority | Sy, LK=rp00784 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1016/j.tet.2007.06.016 | en_US |
dc.identifier.scopus | eid_2-s2.0-34547656015 | en_US |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-34547656015&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 63 | en_US |
dc.identifier.issue | 38 | en_US |
dc.identifier.spage | 9536 | en_US |
dc.identifier.epage | 9547 | en_US |
dc.identifier.isi | WOS:000252091900029 | - |
dc.publisher.place | United Kingdom | en_US |
dc.identifier.scopusauthorid | Brown, GD=7406468149 | en_US |
dc.identifier.scopusauthorid | Sy, LK=35874602700 | en_US |
dc.identifier.issnl | 0040-4020 | - |