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Mar. Drugs 2015, 13(7), 4556-4575; doi:10.3390/md13074556

Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

1
Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia
2
Queensland Museum, Brisbane, Queensland 4101, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Sylvia Urban
Received: 19 June 2015 / Revised: 12 July 2015 / Accepted: 14 July 2015 / Published: 22 July 2015
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Abstract

Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A–C (13), belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A–C (13), respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells. View Full-Text
Keywords: Cnemidocarpa stolonifera; taurine amide; PC3 cell line; immunofluorescence assay Cnemidocarpa stolonifera; taurine amide; PC3 cell line; immunofluorescence assay
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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. (CC BY 4.0).

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MDPI and ACS Style

Tran, T.D.; Pham, N.B.; Ekins, M.; Hooper, J.N.A.; Quinn, R.J. Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera. Mar. Drugs 2015, 13, 4556-4575.

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