Murray H. G. Munro

University of Canterbury, Christchurch, Canterbury Region, New Zealand

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Publications (143)387.37 Total impact

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    Carolina Santiago, Lin Sun, Murray Herbert Gibson Munro, Jacinta Santhanam
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    ABSTRACT: Objective To study bioactivity and compounds produced by an endophytic Phoma sp. fungus isolated from the medicinal plant Cinnamomum mollissimum. Methods Compounds produced by the fungus were extracted from fungal broth culture with ethyl acetate. This was followed by bioactivity profiling of the crude extract fractions obtained via high performance liquid chromatography. The fractions were tested for cytotoxicity to P388 murine leukemic cells and antimicrobial activity against bacteria and pathogenic fungi. Compounds purified from active fractions which showed antibacterial, antifungal and cytotoxic activities were identified using capillary nuclear magnetic resonance analysis, mass spectrometry and admission to AntiMarin database. Results Three known compounds, namely 4-hydroxymellein, 4,8-dihydroxy-6-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one and 1-(2,6-dihydroxyphenyl) ethanone, were isolated from the fungus. The polyketide compound 4-hydroxymellein showed high inhibitory activity against P388 murine leukemic cells (94.6%) and the bacteria Bacillus subtilis (97.3%). Meanwhile, 4,8-dihydroxy-6-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one, a benzopyran compound, demonstrated moderate inhibitory activity against P388 murine leukemic cells (48.8%) and the fungus Aspergillus niger (56.1%). The second polyketide compound, 1 (2,6-dihydroxyphenyl) ethanone was inactive against the tested targets. Conclusions These findings demonstrate the potential of endophytes as producers of pharmacologically important compounds, including polyketides which are major secondary metabolites in fungi.
    Asia Pacific Journal of Tropical Biomedicine. 08/2014; 4(8):627-632.
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    ABSTRACT: This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1241 for 2012), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
    Natural Product Reports 02/2014; 31(2):160-258. · 10.18 Impact Factor
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    ABSTRACT: Two further lasiodiplodins, (3R,4R)-4-hydroxy-de-O-methyl-lasiodiplodin and (E)-9-etheno-de-O-methyl-lasiodiplodin, together with three known lasiodiplodins from a cytotoxic extract obtained from a culture of Lasiodiplodia theobromae, an endophyte from the root tissues of Mapania kurzii (Cyperaceae) from the Malaysian rain forest, were characterized on microgram scale.
    Tetrahedron Letters 01/2014; 55(2):453–455. · 2.40 Impact Factor
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    ABSTRACT: Coverage period: 1965 to 2012This review covers the literature published for marine natural products isolated from macroalgae and addresses the taxonomic details of source organisms, the chemical types of isolated compounds and the location of sampling sites. The emphasis of this review is on the identification of the most bioprospected taxa and regions, as well as on how these trends have shifted over time.
    Natural Product Reports 08/2013; · 10.18 Impact Factor
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    ABSTRACT: This 2011 review of marine natural products describes 1152 new compounds and reports structural revisions and assignments of absolute configurations for previously described compounds. Included is an example of the development of genome mining for the discovery of new compounds from marine microbes leading to the finding of salinosporamide K from Salinispora pacifica.
    Natural Product Reports 02/2013; 30:237-323. · 10.18 Impact Factor
  • John W. Blunt, Murray H. G. Munro
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    ABSTRACT: Research on all aspects of marine natural products has become increasingly dependent on access to databases of information on bibliography, taxonomy, compound structures, spectroscopic and physical properties data, and biological activities. Convenient access to and effective use of these databases, especially a 1H NMR database, can lead to a more efficient use of time and effort in (marine) natural product investigations. A survey of the available databases is presented and how appropriate application can markedly reduce the effort required in the process of dereplication.
    Phytochemistry Reviews 01/2013; · 4.15 Impact Factor
  • Andrea M. Contreras, Islay D. Marsden, Murray H. G. Munro
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    ABSTRACT: Algal blooms produced by toxic dinoflagellates have increased worldwide, resulting in economic losses to aquaculture and fisheries. Bivalve species differ in their ability to feed on toxin-producing dinoflagellates and this could result in differences in toxin accumulation among species. In New Zealand, the effects of paralytic shellfish poisoning (PSP) toxins on the physiology of bivalve molluscs are relatively unknown. We hypothesised that the feeding responses of five New Zealand bivalve species exposed to PSP-toxic dinoflagellates would be species-specific, affecting their accumulation of toxins. Each species was exposed to toxic and non-toxic species of Alexandrium spp. and clearance rate used as an index of sensitivity to PSP toxins. Clearance rates for the mussel Perna canaliculus and the clam Dosinia anus were unaffected by the presence of toxic dinoflagellates, whereas the rate in the scallop Pecten novaezelandiae decreased significantly. There were variable results for the clam Paphies donacina and the oyster Ostrea chilensis. Species-specific biotransformation of PSP-toxins had taken place in the bivalve tissues. We conclude that the rate of accumulation of PSP toxins in the tissues of the bivalve species was influenced by their feeding behaviour and the different chemical processes that had taken place in their tissues.
    Marine and Freshwater Research 02/2012; 63(2):166-174. · 1.98 Impact Factor
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    ABSTRACT: Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
    Natural Product Reports 02/2012; 29(2):144-222. · 10.18 Impact Factor
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    ABSTRACT: The application of an HPLC bioactivity profiling/microtiter plate technique in conjunction with microprobe NMR instrumentation and access to the AntiMarin database has led to the isolation of a new 1. In this example, 1 was isolated from a cytotoxic fraction of an extract obtained from marine-derived Streptomyces sp. cultured on Starch Casein Agar (SCA) medium. The 1D and 2D (1)H NMR and ESIMS data obtained from 20 μg of compound 1 fully defined the structure. The known 2 was also isolated and readily dereplicated using this approach.
    BioMed Research International 01/2012; 2012:894708. · 2.71 Impact Factor
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    ABSTRACT: An endophytic fungus isolated from the plant Cinnamomum mollissimum was investigated for the bioactivity of its metabolites. The fungus, similar to a Phoma sp., was cultured in potato dextrose broth for two weeks, followed by extraction with ethyl acetate. The crude extract obtained was fractionated by high-performance liquid chromatography. Both crude extract and fractions were assayed for cytotoxicity against P388 murine leukemic cells and inhibition of bacterial and fungal pathogens. The bioactive extract fraction was purified further and characterized by nuclear magnetic resonance, mass spectral and X-ray crystallography analysis. A polyketide compound, 5-hydroxyramulosin, was identified as the constituent of the bioactive fungal extract fraction. This compound inhibited the fungal pathogen Aspergillus niger (IC(50) 1.56 μg/mL) and was cytotoxic against murine leukemia cells (IC(50) 2.10 μg/mL). 5-Hydroxyramulosin was the major compound produced by the endophytic fungus. This research suggests that fungal endophytes are a good source of bioactive metabolites which have potential applications in medicine.
    Evidence-based Complementary and Alternative Medicine 01/2012; 2012:689310. · 1.72 Impact Factor
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    ABSTRACT: Compounds 2-5, incorporating various elements of the 3,4'-bis(piperidine) core associated with the sponge-derived alkaloid haliclonacyclamine A (HA, 1), have been prepared through, inter alia, aldol-type reactions of N-substituted piperidin-4-ones and certain derivatives. Screening of these compounds in various assays, including an ecological one, reveals that compound 5 exhibits allelochemical properties similar to those associated with HA itself.
    Organic & Biomolecular Chemistry 11/2011; 10(1):154-61. · 3.57 Impact Factor
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    ABSTRACT: Compounds that modulate microtubule dynamics include highly effective anticancer drugs, leading to continuing efforts to identify new agents and improve the activity of established ones. Here, we demonstrate that [(3)H]-labeled halichondrin B (HB), a complex, sponge-derived natural product, is bound to and dissociated from tubulin rapidly at one binding site per αβ-heterodimer, with an apparent K(d) of 0.31 μM. We found no HB-induced aggregation of tubulin by high-performance liquid chromatography, even following column equilibration with HB. Binding of [(3)H]HB was competitively inhibited by a newly approved clinical agent, the truncated HB analogue eribulin (apparent K(i), 0.80 μM) and noncompetitively by dolastatin 10 and vincristine (apparent K(i)'s, 0.35 and 5.4 μM, respectively). Our earlier studies demonstrated that HB inhibits nucleotide exchange on β-tubulin, and this, together with the results presented here, indicated the HB site is located on β-tubulin. Using molecular dynamics simulations, we determined complementary conformations of HB and β-tubulin that delineated in atomic detail binding interactions of HB with only β-tubulin, with no involvement of the α-subunit in the binding interaction. Moreover, the HB model served as a template for an eribulin binding model that furthered our understanding of the properties of eribulin as a drug. Overall, these results established a mechanistic basis for the antimitotic activity of the halichondrin class of compounds.
    Journal of Chemical Information and Modeling 05/2011; 51(6):1393-404. · 4.30 Impact Factor
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    ABSTRACT: This review covers the literature published in 2011 for marine natural products, with 870 citations (558 for the period January to December 2011) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1152 for 2011), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
    Natural Product Reports 02/2011; 28(2):196-268. · 10.18 Impact Factor
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 10/2010; 26(44).
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    ABSTRACT: Investigations of four different sponge populations of Latrunculia species collected in New Zealand waters has led to the characterization of a new diastereomer of discorhabdin H, named discorhabdin H(2), confirmation of the structure of discorhabdin K ((+)-7), and presentation of a new diastereomer, discorhabdin K(2) ((-)-8). In each case the structures were established by extensive NMR and MS studies and the absolute configurations interrogated by electronic circular dichroism (ECD). Absolute configurations were assigned to the known metabolites discorhabdins H, D, 2-hydroxy-D, N, and Q by comparison of ECD spectra with those recorded for discorhabdin alkaloids of defined absolute configuration, while the configurations of discorhabdins S, T, and U were assigned by semisynthesis from (+)-(6S,8S)-discorhabdin B.
    Journal of Natural Products 09/2010; 73:1686-1693. · 3.29 Impact Factor
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 09/2010; 26(37).
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    ABSTRACT: Microbial natural products (NP) cover a high chemical diversity, and in consequence extracts from microorganisms are often complex to analyze and purify. A distribution analysis of calculated pK(a) values from the 34390 records in Antibase2008 revealed that within pH 2-11, 44% of all included compounds had an acidic functionality, 17% a basic functionality, and 9% both. This showed a great potential for using ion-exchange chromatography as an integral part of the separation procedure, orthogonal to the classic reversed-phase strategy. Thus, we investigated the use of an "explorative solid-phase extraction" (E-SPE) protocol using SAX, Oasis MAX, SCX, and LH-20 columns for targeted exploitation of chemical functionalities. E-SPE provides a minimum of fractions (15) for chemical and biological analyses and implicates development into a preparative scale methodology. Overall, this allows fast extract prioritization, easier dereplication, mapping of biological activities, and formulation of a purification strategy.
    Journal of Natural Products 06/2010; 73(6):1126-32. · 3.29 Impact Factor
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    ABSTRACT: The marine bacterium Vibrio sp. DS40M4 has been found to produce a new triscatechol amide siderophore, trivanchrobactin (1), a related new biscatecholamide compound, divanchrobactin (2), and the previously reported siderophores vanchrobactin (3) and anguibactin (4). Vanchrobactin is comprised of l-serine, d-arginine, and 2,3-dihydroxybenzoic acid, while trivanchrobactin is a linear trimer of vanchrobactin joined by two serine ester linkages. The cyclic trivanchrobactin product was not detected. In addition to siderophore production, extracts of Vibrio sp. DS40M4 were screened for biologically active molecules; anguibactin was found to be cytotoxic against the P388 murine leukemia cell line (IC(50) < 15 microM).
    Journal of Natural Products 06/2010; 73(6):1038-43. · 3.29 Impact Factor
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    ABSTRACT: Chemical analysis of an Indonesian sponge sample has provided three new 3-alkylpiperidine alkaloids, tetradehydrohaliclonacyclamine A, its mono-N-oxide derivative, and a 2-epi isomer. The absolute structure of tetradehydrohaliclonacyclamine A has been established by X-ray crystallography from anomalous dispersion effects using Cu radiation, which determined that the absolute configuration is 2S, 3S, 7S, 9S while an HPLC study revealed that the alkaloid is enantiomerically pure.Graphical abstractThe structure and relative configuration of three new 3-alkylpiperidines, tetradehydrohaliclonacyclamine A 10, its mono-N-oxide 11, and the C-2 epimer 12, have been deduced by 2D NMR spectroscopy. An X-ray crystallographic study has provided the absolute configuration of 10.
    Tetrahedron 04/2010; 66(14):2752-2760. · 2.80 Impact Factor
  • ChemInform 01/2010; 28(40).

Publication Stats

3k Citations
387.37 Total Impact Points

Institutions

  • 1980–2014
    • University of Canterbury
      • Department of Chemistry
      Christchurch, Canterbury Region, New Zealand
  • 2012
    • Putra University, Malaysia
      • Faculty of Food Science and Technology
      Klang, Selangor, Malaysia
  • 2011
    • Australian National University
      • Research School of Chemistry
      Canberra, Australian Capital Territory, Australia
  • 2006
    • University of Colombo
      • Department of Chemistry
      Colombo, Western Province, Sri Lanka
  • 2005
    • Technical University of Denmark
      • Center for Microbial Biotechnology
      Copenhagen, Capital Region, Denmark
  • 2004–2005
    • University of Copenhagen
      • Department of Chemistry
      Copenhagen, Capital Region, Denmark
  • 1988–1989
    • The National Institute of Diabetes and Digestive and Kidney Diseases
      Maryland, United States
  • 1963–1966
    • University of Otago
      • Department of Chemistry
      Dunedin, Otago, New Zealand