Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia

During a high-throughput screen of 300 Australian marine invertebrate extracts, the extract of the marine sponge Clathria (Thalysias) cf. hesperia was identified with α-synuclein binding activity. The bioassay-guided purification of this extract resulted in the isolation of 1-methyl-1,2,7,8-tetrahyd...

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Main Authors: Dale W. Prebble, Tanja M. Voser, Safak Er, Irena Hlushchuk, Andrii Domanskyi, Mikko Airavaara, Merrick G. Ekins, George D. Mellick, Anthony R. Carroll
Format: Article
Language:English
Published: Elsevier 2022-01-01
Series:Results in Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715622000212
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author Dale W. Prebble
Tanja M. Voser
Safak Er
Irena Hlushchuk
Andrii Domanskyi
Mikko Airavaara
Merrick G. Ekins
George D. Mellick
Anthony R. Carroll
author_facet Dale W. Prebble
Tanja M. Voser
Safak Er
Irena Hlushchuk
Andrii Domanskyi
Mikko Airavaara
Merrick G. Ekins
George D. Mellick
Anthony R. Carroll
author_sort Dale W. Prebble
collection DOAJ
description During a high-throughput screen of 300 Australian marine invertebrate extracts, the extract of the marine sponge Clathria (Thalysias) cf. hesperia was identified with α-synuclein binding activity. The bioassay-guided purification of this extract resulted in the isolation of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine (2) as the α-syn binder along with one new compound, hesperine (1), and five known compounds, indole-3-carboxaldehyde (3), (Z)-2′-demethylaplysinopsin (4), 2-amino-4′-hydroxyacetophenone (5), 4-hydroxybenzoic acid (6) and 4-hydroxybenzaldehyde (7). Herein, we report the structure elucidation of hesperine (1) and α-syn binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine (2)
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spelling doaj.art-d9b1edf9ef4c4f8cb9d92ed987c40d022022-12-22T03:52:28ZengElsevierResults in Chemistry2211-71562022-01-014100302Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperiaDale W. Prebble0Tanja M. Voser1Safak Er2Irena Hlushchuk3Andrii Domanskyi4Mikko Airavaara5Merrick G. Ekins6George D. Mellick7Anthony R. Carroll8School of Environment and Science, Griffith University (Gold Coast Campus), Parklands Drive, Southport, QLD 4222, Australia; Griffith Institute for Drug Discovery, Griffith University (Brisbane Innovation Park), Don Young Road, Nathan, QLD 4111, AustraliaSchool of Environment and Science, Griffith University (Gold Coast Campus), Parklands Drive, Southport, QLD 4222, AustraliaFaculty of Pharmacy, University of Helsinki, Helsinki 00014, Finland; Institute of Biotechnology, HiLIFE, University of Helsinki, Helsinki 00014, FinlandFaculty of Pharmacy, University of Helsinki, Helsinki 00014, FinlandInstitute of Biotechnology, HiLIFE, University of Helsinki, Helsinki 00014, FinlandFaculty of Pharmacy, University of Helsinki, Helsinki 00014, Finland; Neuroscience Center, HiLIFE, University of Helsinki, Helsinki 00014, FinlandGriffith Institute for Drug Discovery, Griffith University (Brisbane Innovation Park), Don Young Road, Nathan, QLD 4111, Australia; Queensland Museum, South Brisbane BC, QLD 4101, AustraliaSchool of Environment and Science, Griffith University (Gold Coast Campus), Parklands Drive, Southport, QLD 4222, Australia; Griffith Institute for Drug Discovery, Griffith University (Brisbane Innovation Park), Don Young Road, Nathan, QLD 4111, AustraliaSchool of Environment and Science, Griffith University (Gold Coast Campus), Parklands Drive, Southport, QLD 4222, Australia; Griffith Institute for Drug Discovery, Griffith University (Brisbane Innovation Park), Don Young Road, Nathan, QLD 4111, Australia; Corresponding author at: School of Environment and Science, Griffith University (Gold Coast Campus), Parklands Drive, Southport, QLD 4222, Australia.During a high-throughput screen of 300 Australian marine invertebrate extracts, the extract of the marine sponge Clathria (Thalysias) cf. hesperia was identified with α-synuclein binding activity. The bioassay-guided purification of this extract resulted in the isolation of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine (2) as the α-syn binder along with one new compound, hesperine (1), and five known compounds, indole-3-carboxaldehyde (3), (Z)-2′-demethylaplysinopsin (4), 2-amino-4′-hydroxyacetophenone (5), 4-hydroxybenzoic acid (6) and 4-hydroxybenzaldehyde (7). Herein, we report the structure elucidation of hesperine (1) and α-syn binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine (2)http://www.sciencedirect.com/science/article/pii/S2211715622000212Amyloidα-SynucleinClathria (Thalysias) cf. hesperiaAlkaloids
spellingShingle Dale W. Prebble
Tanja M. Voser
Safak Er
Irena Hlushchuk
Andrii Domanskyi
Mikko Airavaara
Merrick G. Ekins
George D. Mellick
Anthony R. Carroll
Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
Results in Chemistry
Amyloid
α-Synuclein
Clathria (Thalysias) cf. hesperia
Alkaloids
title Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
title_full Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
title_fullStr Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
title_full_unstemmed Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
title_short Hesperine, a new imidazole alkaloid and α-synuclein binding activity of 1-methyl-1,2,7,8-tetrahydro-2,8-dioxoadenosine from the marine sponge Clathria (Thalysias) cf. hesperia
title_sort hesperine a new imidazole alkaloid and α synuclein binding activity of 1 methyl 1 2 7 8 tetrahydro 2 8 dioxoadenosine from the marine sponge clathria thalysias cf hesperia
topic Amyloid
α-Synuclein
Clathria (Thalysias) cf. hesperia
Alkaloids
url http://www.sciencedirect.com/science/article/pii/S2211715622000212
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