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  1. Article ; Online: Chemical cues that attract cannibalistic cane toad (Rhinella marina) larvae to vulnerable embryos

    Michael R. Crossland / Angela A. Salim / Robert J. Capon / Richard Shine

    Scientific Reports, Vol 11, Iss 1, Pp 1-

    2021  Volume 8

    Abstract: Abstract Chemical cues produced by late-stage embryos of the cane toad (Rhinella marina) attract older conspecific larvae, which are highly cannibalistic and can consume an entire clutch. To clarify the molecular basis of this attraction response, we ... ...

    Abstract Abstract Chemical cues produced by late-stage embryos of the cane toad (Rhinella marina) attract older conspecific larvae, which are highly cannibalistic and can consume an entire clutch. To clarify the molecular basis of this attraction response, we presented captive tadpoles with components present in toad eggs. As previously reported, attractivity arises from the distinctive toxins (bufadienolides) produced by cane toads, with some toxins (e.g., bufagenins) much stronger attractants than others (e.g., bufotoxins). Extracts of frozen toad parotoid glands (rich in bufagenins) were more attractive than were fresh MeOH extracts of the parotoid secretion (rich in bufotoxins), and purified marinobufagin was more effective than marinobufotoxin. Cardenolide aglycones (e.g., digitoxigenin) were active attractors, whereas C-3 glycosides (e.g., digoxin, oubain) were far less effective. A structure–activity relationship study revealed that tadpole attractant potency strongly correlated with Na+/K+ ATPase inhibitory activity, suggesting that tadpoles monitor and rapidly react to perturbations to Na+/K+ ATPase activity.
    Keywords Medicine ; R ; Science ; Q
    Language English
    Publishing date 2021-06-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  2. Article ; Online: Methods in Microbial Biodiscovery

    Angela A. Salim / Zeinab G. Khalil / Ahmed H. Elbanna / Taizong Wu / Robert J. Capon

    Marine Drugs, Vol 19, Iss 503, p

    2021  Volume 503

    Abstract: This review presents an account of the microbial biodiscovery methodology developed and applied in our laboratory at The University of Queensland, Institute for Molecular Bioscience, with examples drawn from our experiences studying natural products ... ...

    Abstract This review presents an account of the microbial biodiscovery methodology developed and applied in our laboratory at The University of Queensland, Institute for Molecular Bioscience, with examples drawn from our experiences studying natural products produced by Australian marine-derived (and terrestrial) fungi and bacteria.
    Keywords microbial biodiscovery ; microbial isolation ; media MATRIX ; chemical profiling ; molecular networking ; artifacts ; Biology (General) ; QH301-705.5
    Language English
    Publishing date 2021-09-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article ; Online: New from Old

    Shamsunnahar Khushi / Angela A. Salim / Ahmed H. Elbanna / Laizuman Nahar / Robert J. Capon

    Marine Drugs, Vol 19, Iss 2, p

    Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889)

    2021  Volume 97

    Abstract: Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was ... ...

    Abstract Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A ( 1 ), with the GNPS cluster revealing a halo of related alkaloids 1a – 1n . In considering biosynthetic origins, we propose that Thorectandra choanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin ( 2 ), 6-bromoaplysinopsin ( 3 ), aplysinopsin ( 4 ), and 1′,8-dihydroaplysinopsin ( 10 ), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase- like (IDO) enzyme to 1a – 1n . Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a – 1b , and 1h – 1j , respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c – 1g , and 1k – 1n , respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme.
    Keywords Thorectandra choanoides ; tryptophan alkaloid ; indoleamine 2,3-dioxygenase ; aplysinopsins ; GNPS molecular network ; Biology (General) ; QH301-705.5
    Subject code 540
    Language English
    Publishing date 2021-02-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  4. Article ; Online: Talarolides Revisited

    Angela A. Salim / Waleed M. Hussein / Pradeep Dewapriya / Huy N. Hoang / Yahao Zhou / Kaumadi Samarasekera / Zeinab G. Khalil / David P. Fairlie / Robert J. Capon

    Marine Drugs, Vol 21, Iss 487, p

    Cyclic Heptapeptides from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp. CMB-TU011

    2023  Volume 487

    Abstract: Application of a miniaturized 24-well plate system for cultivation profiling (MATRIX) permitted optimization of the cultivation conditions for the marine-derived fungus Talaromyces sp. CMB-TU011, facilitating access to the rare cycloheptapeptide ... ...

    Abstract Application of a miniaturized 24-well plate system for cultivation profiling (MATRIX) permitted optimization of the cultivation conditions for the marine-derived fungus Talaromyces sp. CMB-TU011, facilitating access to the rare cycloheptapeptide talarolide A ( 1 ) along with three new analogues, B–D ( 2 – 4 ). Detailed spectroscopic analysis supported by Marfey’s analysis methodology was refined to resolve N -Me- l -Ala from N -Me- d -Ala, l - allo -Ile from l -Ile and l -Leu, and partial and total syntheses of 2 , and permitted unambiguous assignment of structures for 1 (revised) and 2 – 4 . Consideration of diagnostic ROESY correlations for the hydroxamates 1 and 3 – 4 , and a calculated solution structure for 1 , revealed how cross-ring H-bonding to the hydroxamate moiety influences (defines/stabilizes) the cyclic peptide conformation. Such knowledge draws attention to the prospect that hydroxamates may be used as molecular bridges to access new cyclic peptide conformations, offering the prospect of new biological properties, including enhanced oral bioavailability.
    Keywords talarolides ; Talaromyces ; cycloheptapeptide ; N -OH glycine ; MATRIX ; GNPS molecular networking ; Biology (General) ; QH301-705.5
    Subject code 540
    Language English
    Publishing date 2023-09-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  5. Article ; Online: Cacolides

    Shamsunnahar Khushi / Laizuman Nahar / Angela A. Salim / Robert J. Capon

    Marine Drugs, Vol 16, Iss 11, p

    Sesterterpene Butenolides from a Southern Australian Marine Sponge, Cacospongia sp.

    2018  Volume 456

    Abstract: Chemical analysis of a marine sponge, Cacospongia sp. (CMB-03404), obtained during deep sea commercial fishing activities off the southern coast of Australia, yielded an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides, cacolides A⁻L ( ...

    Abstract Chemical analysis of a marine sponge, Cacospongia sp. (CMB-03404), obtained during deep sea commercial fishing activities off the southern coast of Australia, yielded an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides, cacolides A⁻L ( 1 ⁻ 12 ), together with biosynthetically related norsesterterpene carboxylic acids, cacolic acids A⁻C ( 13 ⁻ 15 ). Structures were assigned on the basis of detailed spectroscopic analysis with comparisons to known natural products and biosynthetic considerations. In addition to revealing new chemical diversity, this study provided a valuable platform for comparing and contrasting the capabilities of the traditional dereplication technologies of HPLC-DAD, HPLC-MS and NMR, with those of the emerging HPLC-MS/MS approach known as global natural products social molecular networking (GNPS), as applied to marine sponge sesterterpene tetronic acids.
    Keywords Cacospongia sp ; sesterterpene butenolides ; dereplication ; GNPS ; sesterterpene tetronic acids ; Biology (General) ; QH301-705.5
    Language English
    Publishing date 2018-11-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  6. Article ; Online: Solvolysis Artifacts

    Pritesh Prasad / Angela A. Salim / Shamsunnahar Khushi / Zeinab G. Khalil / Michelle Quezada / Robert J. Capon

    Marine Drugs, Vol 17, Iss 2, p

    Leucettazoles as Cryptic Macrocyclic Alkaloid Dimers from a Southern Australian Marine Sponge, Leucetta sp.

    2019  Volume 106

    Abstract: Chemical analysis of a southern Australian sponge, Leucetta sp., led to the discovery of a pair of solvolysis adducts, leucettazoles A1 ( 1a ) and B1 ( 2a ), as artifacts of an unprecedented family of 15-membered macrocyclic alkaloid dimers featuring a ... ...

    Abstract Chemical analysis of a southern Australian sponge, Leucetta sp., led to the discovery of a pair of solvolysis adducts, leucettazoles A1 ( 1a ) and B1 ( 2a ), as artifacts of an unprecedented family of 15-membered macrocyclic alkaloid dimers featuring a pair of imino bridged 2-aminoimidazoles, together with a putative monomeric precursor, leucettazine A ( 3 ). The dimeric alkaloids 1a and 2a , and monomer 3 , were identified by detailed spectroscopic analysis, supported by chemical transformations, analytical mass spectrometry, and biosynthetic considerations. Global natural product social networking (GNPS) molecular analysis of crude sponge extracts and solvent partitions, supported by single ion extraction (SIE) and diagnostic MS/MS fragmentations, revealed the associated natural products, leucettazoles A ( 1 ) and B ( 2 ). This study highlights that the study of natural product artifacts can be useful, and can on occasion serve as a pathway to discover cryptic new classes of natural products.
    Keywords ethanolysis ; solvolysis ; artifact ; leucettazoles ; leucettazines ; macrocyclic alkaloids ; Leucetta ; Australian sponge ; GNPS ; Biology (General) ; QH301-705.5
    Subject code 820
    Language English
    Publishing date 2019-02-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article ; Online: Talaropeptides A-D

    Pradeep Dewapriya / Zeinab G. Khalil / Pritesh Prasad / Angela A. Salim / Pablo Cruz-Morales / Esteban Marcellin / Robert J. Capon

    Frontiers in Chemistry, Vol

    Structure and Biosynthesis of Extensively N-methylated Linear Peptides From an Australian Marine Tunicate-Derived Talaromyces sp.

    2018  Volume 6

    Abstract: An Australian marine tunicate-derived fungus, Talaromyces sp. CMB-TU011 was subjected to a program of analytical microbioreactor (MATRIX) cultivations, supported by UHPLC-QTOF profiling, to reveal conditions for producing a new class of extensively N- ... ...

    Abstract An Australian marine tunicate-derived fungus, Talaromyces sp. CMB-TU011 was subjected to a program of analytical microbioreactor (MATRIX) cultivations, supported by UHPLC-QTOF profiling, to reveal conditions for producing a new class of extensively N-methylated 11-12 residue linear peptides, talaropeptides A-D (2-5). The structures for 2-5, inclusive of absolute configurations, were determined by a combination of detailed spectroscopic and chemical (e.g., C3 and C18 Marfey's) analyses. We report on the biological properties of 2-5, including plasma stability, as well as antibacterial, antifungal and cell cytotoxicity. The talaropeptide mega non-ribosomal peptide synthetase (NRPS) is described, as second only in size to that for the fungus-derived immunosuppressant cyclosporine (an 11-residue extensively N-methylated cyclic peptide).
    Keywords marine-derived ; fungus ; Talaromyces ; talaropeptide ; NRPS ; linear peptide ; Chemistry ; QD1-999
    Language English
    Publishing date 2018-09-01T00:00:00Z
    Publisher Frontiers Media S.A.
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  8. Article: Trichodermides A–E: New Peptaibols Isolated from the Australian Termite Nest-Derived Fungus Trichoderma virens CMB-TN16

    Jiao, Wei-Hua / Angela A. Salim / Hou-Wen Lin / Pradeep Dewapriya / Robert J. Capon / Zeinab Khalil

    Journal of natural products. 2018 Mar. 12, v. 81, no. 4

    2018  

    Abstract: Chemical analysis of a fermentation of the Australian termite nest-derived fungus Trichoderma virens CMB-TN16 yielded five new acyclic nonapeptides, trichodermides A–E (1–5). Amino acid residues, configurations, and sequences were determined by a ... ...

    Abstract Chemical analysis of a fermentation of the Australian termite nest-derived fungus Trichoderma virens CMB-TN16 yielded five new acyclic nonapeptides, trichodermides A–E (1–5). Amino acid residues, configurations, and sequences were determined by a combination of spectroscopic (NMR and MS-MS) and chemical (C3 Marfey’s) methods. The trichodermides adhere to the sequence homology pattern common to Trichoderma 11 amino acid residue peptaibols; however, unlike other peptaibols the trichodermides do not exhibit antibacterial or antifungal activity and exhibit low to no cytotoxicity against mammalian cells. This variability in biological activity highlights the importance of knowing both planar structures and absolute configurations when interpreting structure–activity relationships.
    Keywords amino acids ; antifungal properties ; chemical analysis ; cytotoxicity ; fermentation ; fungi ; Isoptera ; mammals ; nuclear magnetic resonance spectroscopy ; peptides ; sequence homology ; structure-activity relationships ; Trichoderma virens
    Language English
    Dates of publication 2018-0312
    Size p. 976-984.
    Publishing place American Chemical Society and American Society of Pharmacognosy
    Document type Article
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.7b01072
    Database NAL-Catalogue (AGRICOLA)

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  9. Article: Bromocatechol conjugates from a Chinese marine red alga, Symphyocladia latiuscula

    Xu, Xiuli / Angela A. Salim / Fuhang Song / Haijin Yang / Liyuan Yin / Robert J. Capon / Xue Xiao / Zeinab G. Khalil

    Phytochemistry. 2019 Feb., v. 158

    2019  

    Abstract: This study describes an investigation into polybromocatechol conjugates isolated from a marine red alga, Symphyocladia latiuscula (Harvey) Yamada, collected from coastal waters off Qingdao, China. We report on the isolation and characterisation of eight ... ...

    Abstract This study describes an investigation into polybromocatechol conjugates isolated from a marine red alga, Symphyocladia latiuscula (Harvey) Yamada, collected from coastal waters off Qingdao, China. We report on the isolation and characterisation of eight undescribed aconitic acid conjugates, symphyocladins R-X, including a likely solvolysis artifact of symphyocladin S, and an undescribed furanoyl conjugate, symphyocladin Y. Structure elucidation was achieved by detailed spectroscopic analysis. A plausible biosynthetic pathway linking all these co-metabolites through a cascade of quinone methide additions is proposed.
    Keywords aconitic acid ; biochemical pathways ; coastal water ; Rhodophyta ; solvolysis ; spectral analysis ; China
    Language English
    Dates of publication 2019-02
    Size p. 20-25.
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 208884-8
    ISSN 1873-3700 ; 0031-9422
    ISSN (online) 1873-3700
    ISSN 0031-9422
    DOI 10.1016/j.phytochem.2018.10.026
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

    Z 1586: Show issues
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  10. Article ; Online: Correction

    Jeroen Overman / Frank Fontaine / Mehdi Moustaqil / Deepak Mittal / Emma Sierecki / Natalia Sacilotto / Johannes Zuegg / Avril AB Robertson / Kelly Holmes / Angela A Salim / Sreeman Mamidyala / Mark S Butler / Ashley S Robinson / Emmanuelle Lesieur / Wayne Johnston / Kirill Alexandrov / Brian L Black / Benjamin M Hogan / Sarah De Val /
    Robert J Capon / Jason S Carroll / Timothy L Bailey / Peter Koopman / Ralf Jauch / Matthew A Cooper / Yann Gambin / Mathias Francois

    eLife, Vol

    Pharmacological targeting of the transcription factor SOX18 delays breast cancer in mice

    2023  Volume 12

    Keywords Medicine ; R ; Science ; Q ; Biology (General) ; QH301-705.5
    Language English
    Publishing date 2023-08-01T00:00:00Z
    Publisher eLife Sciences Publications Ltd
    Document type Article ; Online
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