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RESEARCH ARTICLE
Contents Vol 67(9)

Acanthocyclamine A From the Indonesian Marine Sponge Acanthostrongylophora ingens

Ariyanti S. Dewi A B , Tri A. Hadi C , Nurrahmi D. Fajarningsih B , Joanne T. Blanchfield A , Paul V. Bernhardt A D and Mary J. Garson A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, Qld 4072, Australia.

B Research and Development Center for Marine and Fisheries Product Processing and Biotechnology, Ministry of Marine Affairs and Fisheries, Jakarta 10260, Indonesia.

C Research Center for Oceanography, Indonesian Institute of Sciences, Jakarta 14430, Indonesia.

D Corresponding authors. Email: m.garson@uq.edu.au; p.bernhardt@uq.edu.au

Australian Journal of Chemistry 67(9) 1205-1210 https://doi.org/10.1071/CH14107
Submitted: 28 February 2014  Accepted: 20 March 2014   Published: 8 May 2014

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.


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