Isolation of thuridillins D−F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring

Somerville, Michael J., Katavic, Peter L., Lambert, Lynette K., Pierens, Gregory K., Blanchfield, Joanne T., Cimino, Guido, Mollo, Ernesto, Gavagnin, Margherita, Banwell, Martin G. and Garson, Mary J. (2012) Isolation of thuridillins D−F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring. Journal of Natural Products, 75 9: 1618-1624. doi:10.1021/np300442s


Author Somerville, Michael J.
Katavic, Peter L.
Lambert, Lynette K.
Pierens, Gregory K.
Blanchfield, Joanne T.
Cimino, Guido
Mollo, Ernesto
Gavagnin, Margherita
Banwell, Martin G.
Garson, Mary J.
Title Isolation of thuridillins D−F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring
Formatted title
Isolation of thuridillins D−F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
1520-6025
Publication date 2012-09-01
Year available 2012
Sub-type Article (original research)
DOI 10.1021/np300442s
Open Access Status Not yet assessed
Volume 75
Issue 9
Start page 1618
End page 1624
Total pages 7
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Abstract This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Delta(10,11) and Delta(11,12)-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and H-1-H-1 coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).
Formatted abstract
This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D–F (1–3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D–F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H–1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).
Keyword Plant Sciences
Chemistry, Medicinal
Pharmacology & Pharmacy
Plant Sciences
Pharmacology & Pharmacy
CHEMISTRY, MEDICINAL
PHARMACOLOGY & PHARMACY
PLANT SCIENCES
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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Created: Fri, 21 Sep 2012, 00:27:25 EST by Sandrine Ducrot on behalf of Centre for Advanced Imaging