Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

In order to further expand the NatureBank open access compound library, chemical investigations of the Australian marine sponge, Ianthella basta, were undertaken since UHPLC–MS analysis of the extract from this sponge indicated the presence of a new alkaloid. Large-scale extraction and mass-directed isolation studies on the CH2Cl2/MeOH I. basta extract resulted in the purification of a new bromotyrosine-derived alkaloid, 5-debromopurealidin H (1), along with the known marine natural product, ianthesine E (2). The chemical structure of the new compound was determined following detailed spectroscopic and spectrometric data analysis. These two compounds (1 and 2) along with seven previously reported marine bromotyrosine alkaloids from the NatureBank open access library, which included psammaplysins F (3) and H (4), bastadins 4 (5), 8 (6) and 13 (7), aerothionin (8) and hexadellin A (9), were evaluated for their nematocidal activity against exsheathed third-stage larvae of Haemonchus contortus, a highly pathogenic parasite of ruminants. Of the nine compounds, bastadin 8 (6), hexadellin A (9) and bastadin 4 (5) showed inhibition towards larval motility after 72 h of exposure with IC50 values of 1.6 µM, 10.0 µM and 33.3 µM, respectively.

[1]  A. Carroll,et al.  Marine natural products. , 2022, Natural product reports.

[2]  A. Hofmann,et al.  Dysidenin from the Marine Sponge Citronia sp. Affects the Motility and Morphology of Haemonchus contortus Larvae In Vitro , 2021, Marine drugs.

[3]  Bill C. H. Chang,et al.  High Throughput Screening of the NatureBank ‘Marine Collection’ in a Haemonchus Bioassay Identifies Anthelmintic Activity in Extracts from a Range of Sponges from Australian Waters , 2021, Molecules.

[4]  Bill C. H. Chang,et al.  High-Throughput Phenotypic Assay to Screen for Anthelmintic Activity on Haemonchus contortus , 2021, Pharmaceuticals.

[5]  C. Nelson,et al.  Synthesis of a Unique Psammaplysin F Library and Functional Evaluation in Prostate Cancer Cells by Multiparametric Quantitative Single Cell Imaging. , 2020, Journal of natural products.

[6]  I. Tietjen,et al.  Comatulins A-E, Taurine-Conjugated Anthraquinones from the Australian Crinoid Comatula rotalaria. , 2020, Journal of natural products.

[7]  C. Hellio,et al.  Quorum Sensing Inhibitory and Antifouling Activities of New Bromotyrosine Metabolites from the Polynesian Sponge Pseudoceratina n. sp. , 2020, Marine drugs.

[8]  S. Bornstein,et al.  Anti-Tumor Activity vs. Normal Cell Toxicity: Therapeutic Potential of the Bromotyrosines Aerothionin and Homoaerothionin In Vitro , 2020, Marine drugs.

[9]  Bill C. H. Chang,et al.  Identification of Fromiamycalin and Halaminol A from Australian Marine Sponge Extracts with Anthelmintic Activity against Haemonchus contortus , 2019, Marine drugs.

[10]  N. Holroyd,et al.  The global diversity of Haemonchus contortus is shaped by human intervention and climate , 2019, Nature Communications.

[11]  Bill C. H. Chang,et al.  Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro , 2019, International journal for parasitology. Drugs and drug resistance.

[12]  J. Yli-Kauhaluoma,et al.  Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives , 2018, Marine drugs.

[13]  Andrew M. Piggott,et al.  Enantiodivergence in the Biosynthesis of Bromotyrosine Alkaloids from Sponges? , 2017, Journal of natural products.

[14]  N. Khashab,et al.  Synthesis and anticancer evaluation of spermatinamine analogues. , 2016, Bioorganic & medicinal chemistry letters.

[15]  P. Chanvorachote,et al.  Synthesis and Absolute Configuration of Acanthodendrilline, a New Cytotoxic Bromotyrosine Alkaloid from the Thai Marine Sponge Acanthodendrilla sp. , 2016, Chemical & pharmaceutical bulletin.

[16]  D. Youssef,et al.  Bioactive Secondary Metabolites from the Red Sea Marine Verongid Sponge Suberea Species , 2015, Marine drugs.

[17]  Hyi-Seung Lee,et al.  Cytotoxic psammaplysin analogues from a Suberea sp. marine sponge and the role of the spirooxepinisoxazoline in their activity. , 2013, Journal of natural products.

[18]  Rohan A Davis,et al.  Drug-like properties: guiding principles for the design of natural product libraries. , 2012, Journal of natural products.

[19]  D. Muñoz,et al.  Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida , 2011, Marine drugs.

[20]  D. Youssef,et al.  Brominated arginine-derived alkaloids from the red sea sponge Suberea mollis. , 2011, Journal of natural products.

[21]  G. Birrell,et al.  Psammaplysin H, a new antimalarial bromotyrosine alkaloid from a marine sponge of the genus Pseudoceratina. , 2011, Bioorganic & medicinal chemistry letters.

[22]  V. Avery,et al.  Antimalarial bromotyrosine derivatives from the Australian marine sponge Hyattella sp. , 2010, Journal of natural products.

[23]  Jongki Hong,et al.  Cytotoxic bromotyrosine derivatives from a two-sponge association of Jaspis sp. and Poecillastra sp. , 2008, Bioorganic & medicinal chemistry letters.

[24]  J. Kalaitzis,et al.  Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp. , 2008, Natural product research.

[25]  Rohan A. Davis,et al.  Isolation and structure elucidation of the new fungal metabolite (-)-xylariamide A. , 2005, Journal of natural products.

[26]  D. Watters,et al.  The isolation and synthesis of 3-chloro-4-hydroxy-phenylacetamide produced by a plant-associated microfungus of the genus Xylaria , 2005 .

[27]  J. Luna-Herrera,et al.  Aerothionin, a Bromotyrosine Derivative with Antimycobacterial Activity from the Marine Sponge Aplysina gerardogreeni (Demospongia) , 2003 .

[28]  M. Ojika,et al.  Ianthesines A–D, Four Novel Dibromotyrosine-Derived Metabolites from a Marine Sponge, Ianthella sp. , 2000 .

[29]  A. Carroll,et al.  New lamellarin alkaloids from the australian ascidian, didemnum chartaceum , 1999, Journal of natural products.

[30]  M. Kelly-Borges,et al.  Psammaplysin F, a new bromotyrosine derivative from a sponge, Aplysinella sp. , 1997, Journal of natural products.

[31]  H. Hirota,et al.  Ceratinamides A and B: New Antifouling Dibromotyrosine Derivatives from the Marine Sponge Pseudoceratina purpurea , 1996 .

[32]  M. Tsuda,et al.  Lipopurealins D and E and Purealidin H, New Bromotyrosine Alkaloids from the Okinawan Marine Sponge Psammaplysilla purea , 1995 .

[33]  M. Kelly-Borges,et al.  Three bromotyrosine derivatives, one terminating in an unprecedented diketocyclopentenylidene enamine , 1993 .

[34]  Butler,et al.  The Bastadins Revisited - New Chemistry From the Australian Marine Sponge Ianthella-Basta , 1991 .

[35]  R. Andersen,et al.  Cytotoxic metabolites from the sponge Ianthella basta collected in Papua New Guinea. , 1990, Journal of natural products.

[36]  F. Schmitz,et al.  Brominated tyrosine metabolites from an unidentified sponge , 1987 .

[37]  D. Faulkner,et al.  Screening and bioassays for biologically-active substances from forty marine sponge species from San Diego, California, USA , 1985 .

[38]  Y. Kashman,et al.  Two new antibiotics from the red sea sponge Psammaplysilla purpurea , 1983 .

[39]  John Bunt,et al.  The Australian Institute of Marine Science , 1982 .

[40]  E. Fattorusso,et al.  Aerothionin and homoaerothionin: two tetrabromo spirocyclohexadienylisoxazoles from Verongia sponges , 1972 .