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Mar. Drugs 2012, 10(1), 51-63; doi:10.3390/md10010051
Article

Aplisulfamines, New Sulfoxide-Containing Metabolites from an Aplidium Tunicate: Absolute Stereochemistry at Chiral Sulfur and Carbon Atoms Assigned Through an Original Combination of Spectroscopic and Computational Methods

1
, 1
, 1
, 2
, 1,*  and 1
1 The NeaNat Group, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy 2 C.S.I.A.S. (Centro Servizi Interuniversitario di Analisi Strumentale), Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131 Napoli, Italy
* Author to whom correspondence should be addressed.
Received: 28 November 2011 / Revised: 22 December 2011 / Accepted: 23 December 2011 / Published: 4 January 2012
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Abstract

Two new sulfoxide-containing metabolites, aplisulfamines A (1) and B (2), have been isolated from an Aplidium sp. collected in the Bay of Naples. Their planar structure and geometry of a double bond were readily determined by using standard methods, mainly NMR spectroscopy. An original approach was used to assign the absolute configuration at the three contiguous chiral centers present in the structures of both aplisulfamines, two at carbon and one at sulfur. This involved Electronic Circular Dichroism (ECD) studies, J-based configuration analysis and Density Functional Theory (DFT) calculations and represents an interesting integration of modern techniques in stereoanalysis, which could contribute to the enhancement of theoretical protocols recently applied to solve stereochemical aspects in structure elucidation.
Keywords: ascidian; sulfoxide; stereochemical analysis; computational methods; ECD ascidian; sulfoxide; stereochemical analysis; computational methods; ECD
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Aiello, A.; Fattorusso, E.; Imperatore, C.; Luciano, P.; Menna, M.; Vitalone, R. Aplisulfamines, New Sulfoxide-Containing Metabolites from an Aplidium Tunicate: Absolute Stereochemistry at Chiral Sulfur and Carbon Atoms Assigned Through an Original Combination of Spectroscopic and Computational Methods. Mar. Drugs 2012, 10, 51-63.

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