title: Isolation and Total Synthesis of Stolonines A-C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera.
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 (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.
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia. trong.tran@griffithuni.edu.au.
authors.forename: Trong D
authors.initials: TD
authors.lastname: Tran
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia. n.pham@griffith.edu.au.
authors.forename: Ngoc B
authors.initials: NB
authors.lastname: Pham
authors.affiliation: Queensland Museum, Brisbane, Queensland 4101, Australia. merrick.ekins@qm.qld.gov.au.
authors.forename: Merrick
authors.initials: M
authors.lastname: Ekins
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia. john.hooper@qm.qld.gov.au.|Queensland Museum, Brisbane, Queensland 4101, Australia. john.hooper@qm.qld.gov.au.
authors.forename: John N A
authors.initials: JN
authors.lastname: Hooper
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia. r.quinn@griffith.edu.au.
authors.forename: Ronald J
authors.initials: RJ
authors.lastname: Quinn
mesh_terms: D000577:Amides / Q000302:isolation & purification; D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002243:Carbolines / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002853:Chromatography, Liquid; D005455:Fluorescent Antibody Technique; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D011471:Prostatic Neoplasms / Q000188:drug therapy; D021241:Spectrometry, Mass, Electrospray Ionization; D013654:Taurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D014561:Urochordata / Q000737:chemistry*
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D002243:Carbolines; D007211:Indoles; C000606991:stolonine A; C000606992:stolonine C; D013654:Taurine
keywords: Cnemidocarpa stolonifera; PC3 cell line; immunofluorescence assay; taurine amide