Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

Article

Khokhar, Shahan, Feng, Yunjiang, Campitelli, Mark R., Ekins, Merrick G., Hooper, John N. A., Beattie, Karren D., Sadowski, Martin C., Nelson, Colleen C. and Davis, Rohan A.. 2014. "Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp." Bioorganic and Medicinal Chemistry Letters. 24 (15), pp. 3329-3332. https://doi.org/10.1016/j.bmcl.2014.05.104
Article Title

Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.

ERA Journal ID1566
Article CategoryArticle
AuthorsKhokhar, Shahan (Author), Feng, Yunjiang (Author), Campitelli, Mark R. (Author), Ekins, Merrick G. (Author), Hooper, John N. A. (Author), Beattie, Karren D. (Author), Sadowski, Martin C. (Author), Nelson, Colleen C. (Author) and Davis, Rohan A. (Author)
Journal TitleBioorganic and Medicinal Chemistry Letters
Journal Citation24 (15), pp. 3329-3332
Number of Pages4
Year2014
PublisherElsevier
ISSN0960-894X
1464-3405
Digital Object Identifier (DOI)https://doi.org/10.1016/j.bmcl.2014.05.104
Web Address (URL)http://www.ncbi.nlm.nih.gov/pubmed/24973030
Abstract

Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine sponge Hyrtios sp. resulted in the isolation of two new tryptophan alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1–4 were evaluated for their cytotoxicity against a prostate cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 μM.

Keywordstryptophan alkaloid; marine sponge; Hyrtios; DFT-NMR; cytotoxicity
ANZSRC Field of Research 2020340399. Macromolecular and materials chemistry not elsewhere classified
340502. Natural products and bioactive compounds
340799. Theoretical and computational chemistry not elsewhere classified
321105. Chemotherapy
Public Notes

Files associated with this item cannot be displayed due to copyright restrictions.

Byline AffiliationsGriffith University
Queensland Museum, Australia
Australian Prostate Cancer Research Centre, Australia
Queensland University of Technology
Institution of OriginUniversity of Southern Queensland
Permalink -

https://research.usq.edu.au/item/q28qx/isolation-structure-determination-and-cytotoxicity-studies-of-tryptophan-alkaloids-from-an-australian-marine-sponge-hyrtios-sp

Log in to edit
  • 1733
    total views
  • 7
    total downloads
  • 2
    views this month
  • 0
    downloads this month

Export as

Related outputs

The long non-coding RNA GHSROS reprograms prostate cancer cell lines toward a more aggressive phenotype
Thomas, Patrick B., Jeffrey, Penny, Gahete, Manuel D., Whiteside, Eliza, Walpole, Carina, Maugham, Michelle, Jovanovic, Lidija, Gunter, Jennifer, Williams, Elizabeth, Nelson, Colleen, Herington, Adrian, Luque, Raul M., Veedu, Rakesh, Chopin, Lisa K. and Seim, Inge. 2021. "The long non-coding RNA GHSROS reprograms prostate cancer cell lines toward a more aggressive phenotype." PEERJ. 9, pp. 1-29. https://doi.org/10.7717/peerj.10280
The long non-coding RNA GHSROS facilitates breast cancer cell migration and orthotopic xenograft tumour growth
Thomas, Patrick B., Seim, Inge, Jeffery, Penny L., Gahete, Manuel D., Maugham, Michelle, Crisp, Gabrielle J., Stacey, Andrew, Shah, Esha T., Walpole, Carina, Whiteside, Eliza J., Nelson, Colleen C., Herington, Adrian C., Luque, Raul M., Veedu, Rakesh N. and Chopin, Lisa K.. 2019. "The long non-coding RNA GHSROS facilitates breast cancer cell migration and orthotopic xenograft tumour growth." International Journal of Oncology. 55 (6), pp. 1223-1236. https://doi.org/10.3892/ijo.2019.4891
Dysregulated expression of the human long noncoding RNA GHSROS may influence prostate cancer progression and resistance to docetaxel
Thomas, Patrick B., Jeffrey, Penny L., Manuel, Gahete D., Whiteside, Eliza J., Maugham, Michelle, Walpole, Carina, Gunter, Jennifer H., Williams, Elizabeth D., Nelson, Colleen C., Herington, Adrian C., Luque, Raul M., Veedu, Rakesh N., Chopin, Lisa K. and Seim, Inge. 2018. "Dysregulated expression of the human long noncoding RNA GHSROS may influence prostate cancer progression and resistance to docetaxel." Annual Meeting of 2018 American Association for Cancer Research (AACR 2018). Chicago, United States 14 - 18 Apr 2018 United States. American Association for Cancer Research (AACR). https://doi.org/10.1158/1538-7445.AM2018-2452
The long non-coding RNA, GHSROS, mediates prostate cancer growth
Thomas, Patrick, Walpole, Carina Maree, Jeffery, Penny, Jovanovic, Lidija, Herington, Adrian, Nelson, Colleen, Whiteside, Eliza, Veedu, Rakesh, Seim, Inge and Chopin, Lisa. 2018. "The long non-coding RNA, GHSROS, mediates prostate cancer growth ." Annual Scientific Meeting of the Endocrine Society of Australia 2016. Gold Coast, Australia 21 - 24 Aug 2016 United Kingdom . John Wiley & Sons. https://doi.org/10.1111/cen.13259
The discovery, synthesis and antimalarial evaluation of natural product ​based polyamine alkaloids
Choomuenwai, Vanida, Schwartz, Brett D., Beattie, Karren D., Andrews, Katherine T., Khokhar, Shahan and Davis, Rohan A.. 2013. "The discovery, synthesis and antimalarial evaluation of natural product ​based polyamine alkaloids." Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry. 54 (38), pp. 5188-5191. https://doi.org/10.1016/j.tetlet.2013.07.058
Austrocolorone B and Austrocolorin B1, cytotoxic anthracenone dimers from the Tasmanian mushroom Cortinarius vinosipes Gasparini
Beattie, Karren D., Thompson, Dion R., Tiralongo, Evelin, Ratkowsky, David, May, Tom W. and Gill, Melvyn. 2011. "Austrocolorone B and Austrocolorin B1, cytotoxic anthracenone dimers from the Tasmanian mushroom Cortinarius vinosipes Gasparini." Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry. 52 (42), pp. 5448-5451. https://doi.org/10.1016/j.tetlet.2011.08.015
Targeting the Long Non-Coding RNA GHSROS, a Mediator of Prostate Cancer Tumour Growth, with Antisense Oligonucleotides
Thomas, Patrick B, Walpole, Carina M, Jeffrey, Penny L, Jovanovic, Lidija, Herington, Adrian C, Nelson, Colleen C, Whiteside, Eliza, Veedu, Rakesh N, Seim, Inge and Chopin, Lisa K.. 2016. "Targeting the Long Non-Coding RNA GHSROS, a Mediator of Prostate Cancer Tumour Growth, with Antisense Oligonucleotides." 17th Asia‐Pacific Prostate Cancer Conference. Australia 03 - 31 Aug 2016 United Kingdom . John Wiley & Sons.
Solving the supply of Resveratrol Tetramers from Papua New Guinean rainforest Anisoptera species (Dipterocarpaceae) that inhibit bacterial type III secretion systems
Davis, Rohan A., Beattie, Karren D., Xu, Min, Yang, Xinzhou, Yin, Sheng, Holla, Harish, Healy, Peter C., Sykes, Melissa, Shelper, Todd, Avery, Vicky M., Elofsson, Mikael, Sundin, Charlotta and Quinn, Ronald. 2014. "Solving the supply of Resveratrol Tetramers from Papua New Guinean rainforest Anisoptera species (Dipterocarpaceae) that inhibit bacterial type III secretion systems." Journal of Natural Products. 77 (12), pp. 2633-2640. https://doi.org/10.1021/np500433z
Phytochemical studies and bioactivity of Centipeda and Eremophila species
Beattie, Karren D.. 2009. Phytochemical studies and bioactivity of Centipeda and Eremophila species. PhD Thesis Doctor of Philosophy. Southern Cross University.
Cloning of a novel insulin-regulated ghrelin transcript in prostate cancer
Seim, Inge, Lubik, Amy A., Lehman, Melanie L., Tomlinson, Nadine, Whiteside, Eliza J., Herington, Adrian C., Nelson, Colleen C. and Chopin, Lisa K.. 2013. "Cloning of a novel insulin-regulated ghrelin transcript in prostate cancer." Journal of Molecular Endocrinology. 50 (2), pp. 179-191. https://doi.org/10.1530/JME-12-0150
Antibacterial metabolites from Australian macrofungi from the genus Cortinarius
Beattie, Karren D., Rouf, Razina, Gander, Louisa, May, Tom W., Ratkowsky, David, Donner, Christopher D., Gill, Melvyn, Grice, I. Darren and Tiralongo, Evelin. 2010. "Antibacterial metabolites from Australian macrofungi from the genus Cortinarius." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 71 (8-9), pp. 948-955. https://doi.org/10.1016/j.phytochem.2010.03.016
(3R,4S,5S,8S,10R,13R)-3-Hydroxykaura-9(11),16-dien-18-oic acid
Beattie, Karren D., Bhadbhade, Mohan M., Craig, Donald C. and Leach, David N.. 2012. "(3R,4S,5S,8S,10R,13R)-3-Hydroxykaura-9(11),16-dien-18-oic acid." Acta Crystallographica Section E: Crystallographic Communications. 68 (2), pp. o526-o527. https://doi.org/10.1107/S1600536812002206
(2S,3S)-sulfated pterosin C, a cytotoxic sesquiterpene from the Bangladeshi mangrove fern Acrostichum aureum
Uddin, Shaikh J., Jason, Tracey L. H., Beattie, Karren D., Grice, I. Darren and Tiralongo, Evelin. 2011. "(2S,3S)-sulfated pterosin C, a cytotoxic sesquiterpene from the Bangladeshi mangrove fern Acrostichum aureum." Journal of Natural Products. 74 (9), pp. 2010-2013. https://doi.org/10.1021/np2004598
Chemical composition and cytotoxicity of oils and eremophilanes derived from various parts of Eremophila mitchellii Benth (Myoporaceae)
Beattie, Karren D., Waterman, Peter G., Forster, Paul I., Thompson, Dion R. and Leach, David N.. 2011. "Chemical composition and cytotoxicity of oils and eremophilanes derived from various parts of Eremophila mitchellii Benth (Myoporaceae)." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 72 (4-5), pp. 400-408. https://doi.org/10.1016/j.phytochem.2010.12.011
Ethanolic and aqueous extracts derived from Australian fungi inhibit cancer cell growth in vitro
Beattie, Karren D., Ulrich, Rahel, Grice, I. Darren, Uddin, Shaikh, Blake, Tony B., Wood, Kyle A., Steele, Jules, Iu, Fontaine, May, Tom W. and Tiralongo, Evelin. 2011. "Ethanolic and aqueous extracts derived from Australian fungi inhibit cancer cell growth in vitro." Mycologia. 103 (3), pp. 458-465. https://doi.org/10.3852/10-121
Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis
Levrier, Claire, Balastrier, Melodie, Beattie, Karren D., Carroll, Anthony R., Martin, Frederic, Choomuenwai, Vanida and Davis, Rohan A.. 2013. "Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 86, pp. 121-126. https://doi.org/10.1016/j.phytochem.2012.09.019
The diversity and antimicrobial activity of Preussia sp. Endophytes isolated from Australian dry rainforests
Mapperson, Rachel R., Kotiw, Michael, Davis, Rohan A. and Dearnaley, John D. W.. 2014. "The diversity and antimicrobial activity of Preussia sp. Endophytes isolated from Australian dry rainforests." Current Microbiology: an international journal. 68 (1), pp. 30-37. https://doi.org/10.1007/s00284-013-0415-5
Biologically active compounds isolated from Centipeda and their biological activity as antioxidant and antiinflammatory agents
Leach, David N., Stevenson, Lesley, Gabriel, Brigitte and Beattie, Karren. 2012. Biologically active compounds isolated from Centipeda and their biological activity as antioxidant and antiinflammatory agents. WO 2007062468 A1 Jun 7, 2007 WO 2006-AU1812 Nov 29, 2006NZ 594754 A Mar 28, 2013 NZ 2006-594754 Nov 26, 2006AU 2006319748 A1 Jun 7, 2007 AU 2006-319748 Nov 29, 2006AU 2006319748 B2 Sep 8, 2011 CA 2631127 A1 Jun 7, 2007 CA 2006-2631127 Nov 29, 2006EP 1963350 A1 Sep 3, 2008 EP 2006-817561 Nov 29, 2006NZ 568704 A Nov 25, 2011 NZ 2006-568704 Nov 29, 2006US 20090221517 A1 Sep 3, 2009 US 2009-85741 Mar 18, 2009US 8299119 B2 Oct 30, 2012
Xanthones from a microfungus of the genus Xylaria
Healy, Peter C., Hocking, Ailsa, Tran-Dinh, Nai, Pitt, John I., Shivas, Roger G., Mitchell, Jennifer K., Kotiw, Mike and Davis, Rohan A.. 2004. "Xanthones from a microfungus of the genus Xylaria." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 65 (16), pp. 2373-2378. https://doi.org/10.1016/j.phytochem.2004.07.019
Phomoxins B and C: polyketides from an endophytic fungus of the genus eupenicillium
Davis, Rohan A., Andjic, Vesna, Kotiw, Michael and Shivas, Roger G.. 2005. "Phomoxins B and C: polyketides from an endophytic fungus of the genus eupenicillium." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 66 (23), pp. 2771-2775. https://doi.org/10.1016/j.phytochem.2005.09.004
Synthesis of the fungal natural product (-)-xylariamide A
Kotiw, Michael and Davis, Rohan A.. 2005. "Synthesis of the fungal natural product (-)-xylariamide A." Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry. 46 (31), pp. 5199-5201. https://doi.org/10.1016/j.tetlet.2005.05.114
Caelestines A-D, Brominated Quinolinecarboxylic Acids from the Australian Ascidian Aplidium caelestis
Yin, Sheng, Boyle, Glen M., Carroll, Anthony R., Kotiw, Michael, Dearnaley, John, Quinn, Ronald J. and Davis, Rohan A.. 2010. "Caelestines A-D, Brominated Quinolinecarboxylic Acids from the Australian Ascidian Aplidium caelestis." Journal of Natural Products. 73 (9), pp. 1586-1589. https://doi.org/10.1021/np100329w