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155. Marine Natural Products

Author

Blunt, John W., primary, Copp, Brent R., additional, Munro, Murray H. G., additional, Northcote, Peter T., additional, and Prinsep, Michele R., additional

Published
2004
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163. Marine Natural Products

Author

Blunt, John W., primary, Copp, Brent R, additional, Munro, Murray H. G., additional, Northcote, Peter T., additional, and Prinsep, Michele R., additional

Published
2003
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168. Marine natural products

Author

Blunt, John W., primary, Copp, Brent R., additional, Munro, Murray H. G., additional, Northcote, Peter T., additional, and Prinsep, Michèle R., additional

Published
2002
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175. Biologically Active Acetylenic Amino Alcohol and N-Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian Pseudodistoma opacum

Author

Wang, Jiayi, Pearce, A. Norrie, Chan, Susanna T. S., Taylor, Richard B., Page, Michael J., Valentin, Alexis, Bourguet-Kondracki, Marie-Lise, Dalton, James P., Wiles, Siouxsie, and Copp, Brent R.

Abstract

The first occurrence of an acetylenic 1-amino-2-alcohol, distaminolyne A (1), isolated from the New Zealand ascidian Pseudodistoma opacum, is reported. The isolation and structure elucidation of 1and assignment of absolute configuration using the exciton coupled circular dichroism technique are described. In addition, a new N-9 hydroxy analogue (2) of the known P. opacummetabolite 7-bromohomotrypargine is also reported. Antimicrobial screening identified modest activity of 1toward Escherichia coli, Staphylococcus aureus, and Mycobacterim tuberculosis, while 2exhibited a moderate antimalarial activity (IC503.82 μM) toward a chloroquine-resistant strain (FcB1) of Plasmodium falciparum.

Published
2016
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189. Antimicrobial Polyketide Metabolites from Penicillium bissettii and P. glabrum.

Author

Cadelis, Melissa M., Nipper, Natasha S. L., Grey, Alex, Geese, Soeren, van de Pas, Shara J., Weir, Bevan S., Copp, Brent R., and Wiles, Siouxsie

Subjects
NATURAL products, METABOLITES, ESCHERICHIA, ANTI-infective agents, PENICILLIUM, MYCOBACTERIUM, STAPHYLOCOCCUS aureus
Abstract

Screening of several fungi from the New Zealand International Collection of Microorganisms from Plants identified two strains of Penicillium, P. bissettii and P. glabrum, which exhibited antimicrobial activity against Escherichia coli,Klebsiella pneumoniae, and Staphylococcus aureus. Further investigation into the natural products of the fungi, through extraction and fractionation, led to the isolation of five known polyketide metabolites, penicillic acid (1), citromycetin (2), penialdin A (3), penialdin F (4), and myxotrichin B (5). Semi-synthetic derivatization of 1 led to the discovery of a novel dihydro (1a) derivative that provided evidence for the existence of the much-speculated open-chained form of 1. Upon investigation of the antimicrobial activities of the natural products and derivatives, both penicillic acid (1) and penialdin F (4) were found to inhibit the growth of Methicillin-resistant S. aureus. Penialdin F (4) was also found to have some inhibitory activity against Mycobacterium abscessus and M. marinum along with citromycetin (2). [ABSTRACT FROM AUTHOR]

Published
2022
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190. Isolation and Stereospecific Synthesis of Janolusimide B from a New Zealand Collection of the Bryozoan Bugula flabellata

Author

Wang, Jiayi, Prinsep, Michèle R., Gordon, Dennis P., Page, Michael J., and Copp, Brent R.

Abstract

NMR-directed screening of New Zealand marine organisms has led to the isolation of the modified tripeptide janolusimide B from the common invasive bryozoan Bugula flabellata. The structure was established by NMR and MS analysis, degradative hydrolysis and derivatization, and stereoselective fragment synthesis. The bryozoan natural product is an N-methyl analogue of janolusimide, previously reported from the Mediterranean nudibranch Janolus cristatus, a species known to prey upon bryozoa.

Published
2015
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192. Xenovulene A, a Novel GABA-Benzodiazepine Receptor Binding Compound Produced by Acremonium strictum.

Author

AINSWORTH, A. MARTYN, primary, CHICARELLI-ROBINSON, M. INÊS, additional, COPP, BRENT R., additional, FAUTH, URSULA, additional, HYLANDS, PETER J., additional, HOLLOWAY, JACQUELINE A., additional, LATIF, MOHAMMED, additional, O''BEIRNE, GERARD B., additional, PORTER, NEIL, additional, RENNO, DIDIER V., additional, RICHARDS, MICHELLE, additional, and ROBINSON, NEIL, additional

Published
1995
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193. Rapid synthesis of indole cis-enamides via hydroamidation of indolic alkynes.

Author

Dickson, Emma, Copp, Brent R., and Barker, David

Subjects
*INDOLE, *HETEROCYCLIC compounds synthesis, *AMIDATION, *ALKYNES, *RUTHENIUM, *AMIDES, *CHEMICAL research
Abstract

Abstract: The synthesis of indolic cis-enamides using a ruthenium-mediated hydroamidation of indole alkynes with primary oxalamides or α-keto amides is reported. Using this method the total synthesis of igzamide and Z-coscinamides A and B has been achieved. [Copyright &y& Elsevier]

Published
2013
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194. Discovery and Evaluation of Thiazinoquinones as Anti-Protozoal Agents.

Author

Lam, Cary F. C., Norrie Pearce, A., Tan, Shen H., Kaiser, Marcel, and Copp, Brent R.

Abstract

Pure compound screening has identified the dioxothiazino-quinoline-quinone ascidian metabolite ascidiathiazone A (2) to be a moderate growth inhibitor of Trypanosoma brucei rhodesiense (IC50 3.1 μM) and Plasmodium falciparum (K1 dual drug resistant strain) (IC50 3.3 μM) while exhibiting low levels of cytotoxicity (L6, IC50 167 μM). A series of C-7 amide and ▵ 2(3) analogues were prepared that explored the influence of lipophilicity and oxidation state on observed anti-protozoal activity and selectivity. Little variation in anti-malarial potency was observed (IC50 0.62-6.5 μM), and no correlation was apparent between anti-malarial and anti-T. brucei activity. Phenethylamide 7e and ▵ 2(3) -glycine analogue 8k exhibited similar anti-Pf activity to 2 but with slightly enhanced selectivity (SI 72 and 93, respectively), while ▵2(3) -phenethylamide 8e (IC50 0.67 μM, SI 78) exhibited improved potency and selectivity towards T. brucei rhodesiense compared to the natural product hit. A second series of analogues were prepared that replaced the quinoline ring of 2 with benzofuran or benzothiophene moieties. While esters 10a/10b and 15 were once again found to exhibit cytotoxicity, carboxylic acid analogues exhibited potent anti-Pf activity (IC50 0.34-0.035 μM) combined with excellent selectivity (SI 560-4000). In vivo evaluation of a furan carboxylic acid analogue against P. berghei was undertaken, demonstrating 85.7% and 47% reductions in parasitaemia with ip or oral dosing respectively. [ABSTRACT FROM AUTHOR]

Published
2013
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195. Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues.

Author

Fong, Hugo K. H. and Copp, Brent R.

Abstract

A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a panel of human tumor cell lines. Overall it was found that styelsamine analogues were stronger DNA binders, with the natural products styelsamines B and D having particularly high affinity (Kapp 5.33 × 106 and 3.64 × 106 M-1, respectively). In comparison, the cystodytin iminoquinone alkaloids showed lower affinity for DNA, but were typically just as active as styelsamine analogues at inhibiting proliferation of tumor cells in vitro. Sub-panel selectivity towards non-small cell lung, melanoma and renal cancer cell lines were observed for a number of the analogues. Correlation was observed between whole cell activity and clogP, with the most potent antiproliferative activity being observed for 3-phenylpropanamide analogues 37 and 41 (NCI panel average GI50 0.4 µM and 0.32 µM, respectively) with clogP ~4.0-4.5. [ABSTRACT FROM AUTHOR]

Published
2013
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196. Synthesis of Hemitectol, Tectol, and Tecomaquinone I.

Author

Cadelis, Melissa M., Barker, David, and Copp, Brent R.

Subjects
CHEMICAL synthesis, TEAK, MONOMERS, TECTONA, DIMERS
Abstract

The first total syntheses of Tectona grandis (teak) natural products hemitectol and tectol are described. The observation of spontaneous dimerisation of hemitectol to tectol suggests the monomer is the true natural product and that the dimer is an artifact of isolation. [ABSTRACT FROM AUTHOR]

Published
2013
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