Next Article in Journal
Marine Compounds Selectively Induce Apoptosis in Female Reproductive Cancer Cells but Not in Primary-Derived Human Reproductive Granulosa Cells
Previous Article in Journal
Purification, Characterization and Antitumor Activities of a New Protein from Syngnathus acus, an Officinal Marine Fish
Open AccessArticle

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
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.
Mar. Drugs 2012, 10(1), 51-63; https://doi.org/10.3390/md10010051
Received: 28 November 2011 / Revised: 22 December 2011 / Accepted: 23 December 2011 / Published: 4 January 2012
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. View Full-Text
Keywords: ascidian; sulfoxide; stereochemical analysis; computational methods; ECD ascidian; sulfoxide; stereochemical analysis; computational methods; ECD
Show Figures

Figure 1

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Article Access Map

1
Only visits after 24 November 2015 are recorded.
Back to TopTop