Isolation and total synthesis of stolonines A-C, unique taurine amides from the Australian marine tunicate Cnemidocarpa stolonifera

Trong D Tran; N B Pham; M Ekins; J N A Hooper; R J Quinn

doi:10.3390/md13074556

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Isolation and total synthesis of stolonines A-C, unique taurine amides from the Australian marine tunicate Cnemidocarpa stolonifera

Journal article

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Isolation and total synthesis of stolonines A-C, unique taurine amides from the Australian marine tunicate Cnemidocarpa stolonifera

Trong D Tran, N B Pham, M Ekins, J N A Hooper and R J Quinn

Marine Drugs, Vol.13(7), pp.4556-4576

2015

DOI: https://doi.org/10.3390/md13074556

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Abstract

cnemidocarpa stolonifera

taurine amide

PC3 cell line

immunofluorescence assay

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 (1-3), 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 (1-3), 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. © 2015 by the authors; licensee MDPI, Basel, Switzerland.

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Title: Isolation and total synthesis of stolonines A-C, unique taurine amides from the Australian marine tunicate Cnemidocarpa stolonifera
Authors: Trong D Tran (Author) - Griffith University
N B Pham (Author) - Griffith University
M Ekins (Author) - Queensland Herbarium
J N A Hooper (Author) - Griffith University
R J Quinn (Author) - Griffith University
Publication details: Marine Drugs, Vol.13(7), pp.4556-4576
Publisher: MDPI AG
Date published: 2015
DOI: 10.3390/md13074556
ISSN: 1660-3397
Copyright note: Copyright © 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
Language: English
Record Identifier: 99450597502621
Output Type: Journal article

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