Comatulins A-E, Taurine-Conjugated Anthraquinones from the Australian Crinoid Comatula rotalaria

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Author(s)
Lum, Kah Yean
Taki, Aya C
Gasser, Robin B
Tietjen, Ian
Ekins, Merrick G
White, Jonathan M
Addison, Russell S
Hayes, Sasha
St John, James
Davis, Rohan A
Year published
2020
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Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (1–5), together with 11 known marine natural products (6–16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 6–13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the ...
View more >Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (1–5), together with 11 known marine natural products (6–16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 6–13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 μM. Furthermore, compounds 1, 2, 6–10, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 μM) and development (IC50 = 31 μM) and induced the eviscerated (Evi) phenotype.
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View more >Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (1–5), together with 11 known marine natural products (6–16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 6–13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 μM. Furthermore, compounds 1, 2, 6–10, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 μM) and development (IC50 = 31 μM) and induced the eviscerated (Evi) phenotype.
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Journal Title
Journal of Natural Products
Volume
83
Issue
6
Copyright Statement
This document is the Accepted Manuscript versionof a Published Work that appeared in final form in Journal of Natural Products, copyright 2020 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.jnatprod.0c00267
Subject
Chemical sciences
Biological sciences
Biomedical and clinical sciences
Traditional, complementary and integrative medicine
Science & Technology
Life Sciences & Biomedicine
Plant Sciences
Chemistry, Medicinal
Pharmacology & Pharmacy