Acanthocyclamine A from the Indonesian marine sponge Acanthostrongylophora ingens

Dewi, Ariyanti S., Hadi, Tri A., Fajarningsih, Nurrahmi D., Blanchfield, Joanne T., Bernhardt, Paul V. and Garson, Mary J. (2014) Acanthocyclamine A from the Indonesian marine sponge Acanthostrongylophora ingens. Australian Journal of Chemistry, 67 8-9: 1205-1210. doi:10.1071/CH14107


Author Dewi, Ariyanti S.
Hadi, Tri A.
Fajarningsih, Nurrahmi D.
Blanchfield, Joanne T.
Bernhardt, Paul V.
Garson, Mary J.
Title Acanthocyclamine A from the Indonesian marine sponge Acanthostrongylophora ingens
Formatted title
Acanthocyclamine A from the Indonesian marine sponge Acanthostrongylophora ingens
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 0004-9425
1445-0038
Publication date 2014-01-01
Sub-type Article (original research)
DOI 10.1071/CH14107
Open Access Status Not yet assessed
Volume 67
Issue 8-9
Start page 1205
End page 1210
Total pages 6
Place of publication Collingwood, VIC, Australia
Publisher C S I R O Publishing
Language eng
Subject 1600 Chemistry
Abstract A new 3-alkylpiperidine compound (-)-acanthocyclamine A (1) has been obtained from the methanolic extract of Acanthostrongylophora ingens (order Haplosclerida, family Petrosiidae) collected from Wakatobi Marine National Park in South East Sulawesi, Indonesia. The structure of 1 was investigated by extensive 1D-and 2D-NMR experiments. The absolute configuration of 1 was established by X-ray crystallography from anomalous dispersion effects using Cu radiation as C2 (R), C3 (R), C7 (R), and C9 (R). A plausible biosynthetic scheme leading to 1 is presented, and compared with the biosynthetic pathway proposed for the manzamine alkaloids.
Formatted abstract
A new 3-alkylpiperidine compound (—)-acanthocyclamine A (1) has been obtained from the methanolic extract of Acanthostrongylophora ingens (order Haplosclerida, family Petrosiidae) collected from Wakatobi Marine National Park in South East Sulawesi, Indonesia. The structure of 1 was investigated by extensive 1D- and 2D-NMR experiments. The absolute configuration of 1 was established by X-ray crystallography from anomalous dispersion effects using Cu radiation as C2 (R), C3 (R), C7 (R), and C9 (R). A plausible biosynthetic scheme leading to 1 is presented, and compared with the biosynthetic pathway proposed for the manzamine alkaloids.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 19 Sep 2014, 22:57:50 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences