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  1. Article ; Online: Sycosterol A, an α-Synuclein Inhibitory Sterol from the Australian Ascidian

    Prebble, Dale W / Xu, Mingming / Mellick, George D / Carroll, Anthony R

    Journal of natural products

    2021  Volume 84, Issue 12, Page(s) 3039–3043

    Abstract: During a recent biodiscovery study to identify new α-synuclein (α-syn) aggregation inhibitors, we screened 29 Australian marine sponge and ascidian extracts in an MS binding assay. This resulted in an extract from the ... ...

    Abstract During a recent biodiscovery study to identify new α-synuclein (α-syn) aggregation inhibitors, we screened 29 Australian marine sponge and ascidian extracts in an MS binding assay. This resulted in an extract from the ascidian
    MeSH term(s) Animals ; Australia ; Magnetic Resonance Spectroscopy/methods ; Mass Spectrometry/methods ; Molecular Structure ; Sterols/chemistry ; Sterols/pharmacology ; Urochordata/chemistry ; alpha-Synuclein/antagonists & inhibitors
    Chemical Substances Sterols ; alpha-Synuclein
    Language English
    Publishing date 2021-11-17
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.1c00768
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  2. Article ; Online: α-Synuclein Aggregation Inhibitory and Antiplasmodial Activity of Constituents from the Australian Tree

    Prebble, Dale W / Holland, Darren C / Ferretti, Francesca / Hayton, Joshua B / Avery, Vicky M / Mellick, George D / Carroll, Anthony R

    Journal of natural products

    2023  Volume 86, Issue 9, Page(s) 2171–2184

    Abstract: Amyloid protein aggregates are linked to the progression of neurodegenerative conditions and may play a role in life stages ... ...

    Abstract Amyloid protein aggregates are linked to the progression of neurodegenerative conditions and may play a role in life stages of
    MeSH term(s) Antimalarials/pharmacology ; Eucalyptus ; Trees ; alpha-Synuclein ; Plant Extracts/chemistry ; Australia ; Plasmodium falciparum
    Chemical Substances Antimalarials ; alpha-Synuclein ; Plant Extracts
    Language English
    Publishing date 2023-08-23
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.3c00458
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  3. Article ; Online: Amphiphilic Polyamine α-Synuclein Aggregation Inhibitors from the Sponge

    Voser, Tanja M / Hayton, Joshua B / Prebble, Dale W / Jin, Ju / Grant, Gary / Ekins, Merrick G / Carroll, Anthony R

    Journal of natural products

    2023  Volume 86, Issue 3, Page(s) 475–481

    Abstract: Bioassay-guided investigation of the ... ...

    Abstract Bioassay-guided investigation of the sponge
    MeSH term(s) Animals ; alpha-Synuclein ; Antineoplastic Agents/pharmacology ; Cell Line ; Staphylococcus aureus ; Polyamines/pharmacology ; Porifera
    Chemical Substances alpha-Synuclein ; Antineoplastic Agents ; Polyamines
    Language English
    Publishing date 2023-02-16
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.2c01125
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  4. Article: Sycosterol A, an α-Synuclein Inhibitory Sterol from the Australian Ascidian Sycozoa cerebriformis

    Prebble, Dale W. / Xu, Mingming / Mellick, George D. / Carroll, Anthony R.

    Journal of natural products. 2021 Nov. 17, v. 84, no. 12

    2021  

    Abstract: During a recent biodiscovery study to identify new α-synuclein (α-syn) aggregation inhibitors, we screened 29 Australian marine sponge and ascidian extracts in an MS binding assay. This resulted in an extract from the ascidian Sycozoa cerebriformis ... ...

    Abstract During a recent biodiscovery study to identify new α-synuclein (α-syn) aggregation inhibitors, we screened 29 Australian marine sponge and ascidian extracts in an MS binding assay. This resulted in an extract from the ascidian Sycozoa cerebriformis showing activity toward α-syn. The bioassay and MS guided isolation process led to the identification of one new polyoxygenated sterol sulfate, sycosterol A (1). The structure of this low-yielding steroid was elucidated from HRMS and NMR analysis. Sycosterol A displayed moderate antiaggregation activity with 46.2% (±1.8) inhibition when screened against α-syn at a 5:1 (sycosterol A:α-syn) molar ratio. The α-syn antiaggregation activity displayed by 1 and the recent discovery of similar sterols with α-syn antiaggregation activity and potent antiprion activity suggest this unique class may be useful antineurodegenerative compounds.
    Keywords Ascidiacea ; Porifera ; bioassays ; sterols ; sulfates
    Language English
    Dates of publication 2021-1117
    Size p. 3039-3043.
    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.1c00768
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  5. Article ; Online: α-Synuclein binding activity of the plant growth promoter asterubine.

    Prebble, Dale W / Er, Safak / Hlushchuk, Irena / Domanskyi, Andrii / Airavaara, Mikko / Ekins, Merrick G / Mellick, George D / Carroll, Anthony R

    Bioorganic & medicinal chemistry letters

    2022  Volume 64, Page(s) 128677

    Abstract: Preventing the aggregation of certain amyloid proteins has the potential to slow down the progression of diseases like Alzheimer's, Parkinson's, and type 2 diabetes mellitus. During a high-throughput screen of 300 Australian marine invertebrate extracts, ...

    Abstract Preventing the aggregation of certain amyloid proteins has the potential to slow down the progression of diseases like Alzheimer's, Parkinson's, and type 2 diabetes mellitus. During a high-throughput screen of 300 Australian marine invertebrate extracts, the extract of the marine sponge Thorectandra sp. 4408 displayed binding activity to the Parkinson's disease-associated protein, α-synuclein. Isolation of the active component led to its identification as the known plant growth promoter asterubine (1). This molecule shares distinct structural similarities with potent amyloid beta aggregation inhibitors tramiprosate (homotaurine) and ALZ-801. Herein we report the isolation, NMR data acquired in DMSO and α-synuclein binding activity of asterubine (1).
    MeSH term(s) Amyloid/metabolism ; Amyloid beta-Peptides/metabolism ; Australia ; Diabetes Mellitus, Type 2 ; Humans ; Parkinson Disease/metabolism ; alpha-Synuclein
    Chemical Substances Amyloid ; Amyloid beta-Peptides ; alpha-Synuclein
    Language English
    Publishing date 2022-03-14
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2022.128677
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  6. Article ; Online: Citronamine A, an Antiplasmodial Isoquinoline Alkaloid from the Australian Marine Sponge

    Prebble, Dale W / Holland, Darren C / Robertson, Luke P / Avery, Vicky M / Carroll, Anthony R

    Organic letters

    2020  Volume 22, Issue 24, Page(s) 9574–9578

    Abstract: Citronamine A ( ...

    Abstract Citronamine A (
    MeSH term(s) Alkaloids/chemistry ; Animals ; Antimalarials/chemistry ; Antimalarials/pharmacology ; Australia ; Isoquinolines/chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Plant Extracts/chemistry ; Plant Extracts/isolation & purification ; Plant Extracts/pharmacology ; Plasmodium falciparum ; Porifera/chemistry
    Chemical Substances Alkaloids ; Antimalarials ; Isoquinolines ; Plant Extracts
    Language English
    Publishing date 2020-11-24
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.0c03633
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  7. Article ; Online: α-Synuclein Aggregation Inhibitory Procerolides and Diphenylalkanes from the Ascidian

    Prebble, Dale W / Holland, Darren C / Hayton, Joshua B / Ferretti, Francesca / Jennings, Laurence K / Everson, Jack / Xu, Mingming / Kiefel, Milton J / Mellick, George D / Carroll, Anthony R

    Journal of natural products

    2023  Volume 86, Issue 3, Page(s) 533–540

    Abstract: The aggregation of the neuronal protein α-synuclein (α-syn) is intrinsically linked to the development and progression of Parkinson's disease (PD). Recently we screened the MeOH extracts from 283 marine invertebrates for α-syn binding activity using an ... ...

    Abstract The aggregation of the neuronal protein α-synuclein (α-syn) is intrinsically linked to the development and progression of Parkinson's disease (PD). Recently we screened the MeOH extracts from 283 marine invertebrates for α-syn binding activity using an affinity mass spectrometry (MS) binding assay and found that the extract of the ascidian
    MeSH term(s) Animals ; Humans ; alpha-Synuclein/metabolism ; Urochordata/metabolism ; Parkinson Disease/metabolism
    Chemical Substances alpha-Synuclein ; Procera ; butenolide (8KXK25H388)
    Language English
    Publishing date 2023-02-14
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.2c01140
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  8. Article: Citronamine A, an Antiplasmodial Isoquinoline Alkaloid from the Australian Marine Sponge Citronia astra

    Prebble, Dale W / Holland, Darren C / Robertson, Luke P / Avery, Vicky M / Carroll, Anthony R

    Organic letters. 2020 Nov. 24, v. 22, no. 24

    2020  

    Abstract: Citronamine A (1), an isoquinoline alkaloid containing an unprecedented pentacyclic ring system, was isolated from the Australian marine sponge Citronia astra. Based on the combination of MS and NMR analyses and comparison of experimental and TDDFT ... ...

    Abstract Citronamine A (1), an isoquinoline alkaloid containing an unprecedented pentacyclic ring system, was isolated from the Australian marine sponge Citronia astra. Based on the combination of MS and NMR analyses and comparison of experimental and TDDFT calculated ECD spectra, the absolute structure of 1 was determined. Compound 1 displayed moderate activity against drug sensitive (3D7) and drug resistant (Dd2) strains of the parasite, Plasmodium falciparum, responsible for malaria.
    Keywords Plasmodium falciparum ; Porifera ; alkaloids ; antimalarials ; drug resistance ; malaria ; parasites
    Language English
    Dates of publication 2020-1124
    Size p. 9574-9578.
    Publishing place American Chemical Society
    Document type Article
    Note NAL-AP-2-clean
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.0c03633
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  9. Article: α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian Synoicum prunum

    Holland, Darren C. / Prebble, Dale W. / Er, Safak / Hayton, Joshua B. / Robertson, Luke P. / Avery, Vicky M. / Domanskyi, Andrii / Kiefel, Milton J. / Hooper, John N. A. / Carroll, Anthony R.

    Journal of natural products. 2022 Jan. 20, v. 85, no. 2

    2022  

    Abstract: Seven new polyaromatic bis-spiroketal-containing butenolides, the prunolides D–I (4–9) and cis-prunolide C (10), a new dibrominated β-carboline sulfamate named pityriacitrin C (11), alongside the known prunolides A–C (1–3) were isolated from the ... ...

    Abstract Seven new polyaromatic bis-spiroketal-containing butenolides, the prunolides D–I (4–9) and cis-prunolide C (10), a new dibrominated β-carboline sulfamate named pityriacitrin C (11), alongside the known prunolides A–C (1–3) were isolated from the Australian colonial ascidian Synoicum prunum. The prunolides D–G (4–7) represent the first asymmetrically brominated prunolides, while cis-prunolide C (10) is the first reported with a cis-configuration about the prunolide’s bis-spiroketal core. The prunolides displayed binding activities with the Parkinson’s disease-implicated amyloid protein α-synuclein in a mass spectrometry binding assay, while the prunolides (1–5 and 10) were found to significantly inhibit the aggregation (>89.0%) of α-synuclein in a ThT amyloid dye assay. The prunolides A–C (1–3) were also tested for inhibition of pSyn aggregate formation in a primary embryonic mouse midbrain dopamine neuron model with prunolide B (2) displaying statistically significant inhibitory activity at 0.5 μM. The antiplasmodial and antibacterial activities of the isolates were also examined with prunolide C (3) displaying only weak activity against the 3D7 parasite strain of Plasmodium falciparum. Our findings reported herein suggest that the prunolides could provide a novel scaffold for the exploration of future therapeutics aimed at inhibiting amyloid protein aggregation and the treatment of numerous neurodegenerative diseases.
    Keywords Ascidiacea ; Plasmodium falciparum ; amyloid ; antimalarials ; brain ; bromination ; dopamine ; dyes ; mass spectrometry ; mice ; models ; parasites ; therapeutics
    Language English
    Dates of publication 2022-0120
    Size p. 441-452.
    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.1c01172
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  10. Article ; Online: α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian

    Holland, Darren C / Prebble, Dale W / Er, Safak / Hayton, Joshua B / Robertson, Luke P / Avery, Vicky M / Domanskyi, Andrii / Kiefel, Milton J / Hooper, John N A / Carroll, Anthony R

    Journal of natural products

    2022  Volume 85, Issue 2, Page(s) 441–452

    Abstract: Seven new polyaromatic bis-spiroketal-containing butenolides, the prunolides D-I ( ...

    Abstract Seven new polyaromatic bis-spiroketal-containing butenolides, the prunolides D-I (
    MeSH term(s) Animals ; Australia ; Carbolines ; Mice ; Sulfonic Acids ; Urochordata/chemistry ; alpha-Synuclein
    Chemical Substances Carbolines ; Sulfonic Acids ; alpha-Synuclein ; sulfamic acid (9NFU33906Q)
    Language English
    Publishing date 2022-01-20
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.1c01172
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