Caelestines A-D, Brominated Quinolinecarboxylic Acids from the Australian Ascidian Aplidium caelestis

Article

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
Article Title

Caelestines A-D, Brominated Quinolinecarboxylic Acids from the Australian Ascidian Aplidium caelestis

ERA Journal ID40471
Article CategoryArticle
AuthorsYin, Sheng (Author), Boyle, Glen M. (Author), Carroll, Anthony R. (Author), Kotiw, Michael (Author), Dearnaley, John (Author), Quinn, Ronald J. (Author) and Davis, Rohan A. (Author)
Journal TitleJournal of Natural Products
Journal Citation73 (9), pp. 1586-1589
Number of Pages4
Year2010
Place of PublicationUnited States
ISSN0163-3864
1520-6025
Digital Object Identifier (DOI)https://doi.org/10.1021/np100329w
Web Address (URL)https://pubs.acs.org/doi/10.1021/np100329w
Abstract

Four new brominated natural products, caelestines A-D (1-4), have been isolated from the Australian ascidian Aplidium caelestis. The structures of 1-4 were determined by analysis of their NMR and MS data. This is the first report of brominated quinolinecarboxylic acids from nature. Compound 1 has been previously synthesized but not spectroscopically characterized. Compounds 1-4 were tested against three mammalian cell lines (MCF-7, NFF, and MM96L) and a panel of microbial strains and showed only minor cytotoxicity.

Keywordsaplidium caelestis; quinolinecarboxylic acid; antibacterial activity; drug synthesis; high performance liquid chromatography; microorganism
Contains Sensitive ContentDoes not contain sensitive content
ANZSRC Field of Research 2020320701. Medical bacteriology
340502. Natural products and bioactive compounds
320799. Medical microbiology not elsewhere classified
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Byline AffiliationsGriffith University
Queensland Institute of Medical Research, Australia
Department of Biological and Physical Sciences
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Kotiw, Michael, Zhang, Gwang W., Daggard, Grant, Reiss-Levy, Elizabeth, Tapsall, John W. and Numa, Andrew. 2003. "Late-onset and recurrent neonatal group B streptococcal disease associated with breast milk transmission." Pediatric and Developmental Pathology. 6 (3), pp. 251-256. https://doi.org/10.1007/s10024-001-0276-y
Further advances in orchid mycorrhizal research
Dearnaley, John D. W.. 2007. "Further advances in orchid mycorrhizal research." Mycorrhiza. 17 (6), pp. 475-486. https://doi.org/10.1007/s00572-007-0138-1
Pterostylis nutans (Orchidaceae) has a specific association with two ceratobasidium root-associated fungi across its range in eastern Australia
Irwin, Mathew John, Bougoure, Jeremy James and Dearnaley, John David William. 2007. "Pterostylis nutans (Orchidaceae) has a specific association with two ceratobasidium root-associated fungi across its range in eastern Australia." Mycoscience. 48, pp. 231-239. https://doi.org/10.1007/s10267-007-0360-x
Recent studies of the biology of the yellow hyacinth orchid - Dipodium Hamiltonianum
Dearnaley, John. 2006. "Recent studies of the biology of the yellow hyacinth orchid - Dipodium Hamiltonianum." The Orchadian. 15 (3), pp. 129-130.
Expression of a polygalacturonase enzyme in germinating pollen of Brassica napus
Dearnaley, John and Daggard, Grant. 2001. "Expression of a polygalacturonase enzyme in germinating pollen of Brassica napus." Sexual Plant Reproduction. 13 (5), pp. 265-271. https://doi.org/10.1007/s004970000062
Molecular identification of the primary root fungal endophytes of Dipodium hamiltonianum (Orchidaceae)
Dearnaley, John and Le Brocque, Andrew F.. 2006. "Molecular identification of the primary root fungal endophytes of Dipodium hamiltonianum (Orchidaceae)." Australian Journal of Botany. 54 (5), pp. 487-491. https://doi.org/10.1071/BT05149
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
Isotopic and molecular evidence for saprotrophic Marasmiaceae mycobionts in rhizomes of Gastrodia sesamoides
Dearnaley, John D. W. and Bougoure, Jeremy J.. 2010. "Isotopic and molecular evidence for saprotrophic Marasmiaceae mycobionts in rhizomes of Gastrodia sesamoides." Fungal Ecology. 3 (4), pp. 288-294. https://doi.org/10.1016/j.funeco.2009.11.003
Detection of anti-TNFα activity in canine hyperimmune serum using a TNFα inhibition assay
Kotiw, Michael, Morgan, Michael, Taylor, Stephen M. and Shiels, Ian A.. 2010. "Detection of anti-TNFα activity in canine hyperimmune serum using a TNFα inhibition assay ." Veterinary Clinical Pathology. 39 (1), pp. 46-52. https://doi.org/10.1111/j.1939-165X.2009.00166.x
Phosphate transporter expression in the soybean AM symbiosis
Dearnaley, John, Learmonth, Barbara A. and Bougoure, Damian S.. 2002. "Phosphate transporter expression in the soybean AM symbiosis." 7th International Mycological Congress (IMC7). Oslo, Norway 11 - 17 Aug 2002 Australia.
Orchid mycorrhizas - a disproportionate focus on the minutiae?
Dearnaley, John. 2010. "Orchid mycorrhizas - a disproportionate focus on the minutiae?" 2010 Joint Australasian Mycological Society and the Australian Society for Mycrobiology Meeting. Sydney, Australia 04 - 08 Jul 2010
Anti-inflammatory activity of hyperimmune plasma in a lipopolysaccharide-mediated rat air pouch model of inflammation
Essien, Bryan E. and Kotiw, Michael. 2012. "Anti-inflammatory activity of hyperimmune plasma in a lipopolysaccharide-mediated rat air pouch model of inflammation." Inflammation. 35 (1), pp. 58-64. https://doi.org/10.1007/s10753-010-9289-x
Molecular identification of mycorrhizal fungi in Australian threatened plant species
Dearnaley, John D. W., Downie, Alex F., Murray, Andrew J. and Le Brocque, Andrew F.. 2008. "Molecular identification of mycorrhizal fungi in Australian threatened plant species." Schenk, Peer (ed.) 1st International Conference on Biotic Plant Interactions (ICBPI 2008). Brisbane, Australia 27 - 29 Mar 2008 Brisbane, Australia.
Molecular identification of a mycorrhizal Sebacinaceae from the endangered Caladenia atroclavia (black clubbed spider orchid)
Dearnaley, J. D. W., Murray, A. J. and Mathieson, M. T.. 2009. "Molecular identification of a mycorrhizal Sebacinaceae from the endangered Caladenia atroclavia (black clubbed spider orchid)." Australasian Mycologist. 28 (2-3), pp. 45-50.
Defence gene expression in single mycorrhizal roots of soybean
Dearnaley, John and Learmonth, Barbara A.. 2003. "Defence gene expression in single mycorrhizal roots of soybean." 4th International Conference on Mycorrhizae (ICOM4) . Montreal, Canada 10 - 15 Aug 2003 Québec, Canada.
Effect of canine hyperimmune plasma on TNFa and inflammatory cell levels in a lipopolysaccharide-mediated rat air pouch model of inflammation
Strunin, Dmitry, Essien, Bryan, Kotiw, Michael and Butler, Harry. 2009. "Effect of canine hyperimmune plasma on TNFa and inflammatory cell levels in a lipopolysaccharide-mediated rat air pouch model of inflammation." Reinhart, Konrad (ed.) Sepsis 2009: Critical Care Conference. Amsterdam, Netherlands 11 - 14 Nov 2009 https://doi.org/10.1186/cc8064
The mycorrhizal fungal associations of the vunerable Sophora fraseri (Fabaceae)
Downie, A. F., Le Brocque, A. F. and Dearnaley, J. D. W.. 2008. "The mycorrhizal fungal associations of the vunerable Sophora fraseri (Fabaceae)." Australasian Mycologist. 27 (2), pp. 57-65.
Lantana invades the soil too! Effects of Lantana camara on soil fungal dominance
Case, Heidi, Dearnaley, John and Le Brocque, Andrew F.. 2008. "Lantana invades the soil too! Effects of Lantana camara on soil fungal dominance." Ecological Society of Australia Annual Conference 2008: Interactions in Science, Interactions in Nature (ESA 2008). Sydney, Australia 01 - 05 Dec 2008 Australia.
A mathematical model to account for quantitative iterative effect of TNF-α positive feedback mechanism on inflammatory cascade in TLR-4 mediated TNF-α signaling pathway
Roberts, Tony, Essien, Bryan, Kotiw, Michael, Butler, Harry and Strunin, Dmitry. 2008. "A mathematical model to account for quantitative iterative effect of TNF-α positive feedback mechanism on inflammatory cascade in TLR-4 mediated TNF-α signaling pathway." Ragan, Mark (ed.) 19th International Conference on Genome Informatics (GIW 2008). Gold Coast, Australia 01 - 03 Dec 2008 London, United Kingdom.
In vitro effect of canine hyperimmune sera on TNFa activity
Kotiw, Michael, Shiels, I. A., Wilson, R. P. and Reeve-Johnson, Lloyd. 2006. "In vitro effect of canine hyperimmune sera on TNFa activity." Journal of Veterinary Pharmacology and Therapeutics. 29 (Supplement 1), pp. 100-101. https://doi.org/10.1111/j.1365-2885.2006.00761.x
The effect of equine hyperimmune sera on TNF alpha activity in a L929 cell bioassay
Kotiw, M., Raghaven, C., Johnson, M., Shiels, I. A. and Wilson, R. P.. 2006. "The effect of equine hyperimmune sera on TNF alpha activity in a L929 cell bioassay." Bryden, W. L. (ed.) AESS 2006: Australian Equine Science Symposium: Research for the 21st Century Horse Industry: From Genomics to the Winning Post. Gold Coast, Australia 13 - 14 Jun 2006 Gold Coast, Australia.
Biological methods: a novel course in undergraduate biology
Kotiw, Michael, Learmonth, Robert P. and Sutherland, Mark W.. 1999. "Biological methods: a novel course in undergraduate biology." Biochemical Education. 27 (3), pp. 131-134. https://doi.org/10.1016/S0307-4412(99)00002-3
The relevance of human rights to health status in Australian Aboriginal and Torres Strait Islander communities
Smallwood, Gracelyn, White, Colin and Kotiw, Michael. 1997. "The relevance of human rights to health status in Australian Aboriginal and Torres Strait Islander communities." Health and Human Rights: an international journal. 2 (2), pp. 127-136.
In vitro and in vivo determination of ant-TNFa activity in canine plasma from donors subject to pre conditioning with endotoxin
Kotiw, Michael, Morgan, Michael, Lopez, Jesus, Taylor, Steven and Shiels, Ian. 2007. "In vitro and in vivo determination of ant-TNFa activity in canine plasma from donors subject to pre conditioning with endotoxin." Marshall, John (ed.) SEPSIS 2007: International Sepsis Forum ISF . Paris, France 26 - 29 Sep 2007 London, United Kingdom. https://doi.org/10.1186/cc6002
In the footsteps of Florey: utilising cultured microfungi in the search for new antibiotics
Parker, C., Barrow, Russell, Bloor, S. J., Grace, Emily J., Michael, Adam P., Thompson, Christopher and Kotiw, Michael. 2001. "In the footsteps of Florey: utilising cultured microfungi in the search for new antibiotics." Bernhardt, Debra (ed.) FACS 2001: 9th Asian Chemical Congress . Brisbane, Australia 02 - 04 Jul 2001 Brisbane, Australia.
Endophytic fungi associated with Australian orchids
Dearnaley, John and Le Brocque, Andrew F.. 2006. "Endophytic fungi associated with Australian orchids." Australasian Plant Conservation: Bulletin of the Australian Network for Plant Conservation. 15 (2), pp. 7-9.
Exploring the potential for dual vaccination against Hepatitis B virus and Helicobacter pylori using a recombinant virus like particle
Kotiw, Michael, Olive, C., Johnson, Megan, Pandy, M., Fry, Scott Robert, Hazell, Stuart L., Netter, H. and Good, M.. 2006. "Exploring the potential for dual vaccination against Hepatitis B virus and Helicobacter pylori using a recombinant virus like particle." Sirtori, Patrizia (ed.) 6th National Congress of the Italian Society of Virology - a joint meeting with the Virus Group of the Society for General Microbiology (UK). Orvieto, Italy 18 - 20 Sep 2006 Italy.
Molecular identification of fungal endophytes in Australian myco-heterotrophic orchids
Dearnaley, John. 2006. "Molecular identification of fungal endophytes in Australian myco-heterotrophic orchids." Meyer, Wieland (ed.) 8th International Mycological Congress (IMC8). Cairns, Australia 20 - 25 Aug 2006 Australia.
Fungal endophytes in Australian myco-heterotrophic orchids
Dearnaley, John. 2006. "Fungal endophytes in Australian myco-heterotrophic orchids." Meyer, Wieland (ed.) 8th International Mycological Congress (IMC8). Cairns, Australia 20 - 25 Aug 2006 Australia.
The fungal endophytes of erythrorchis cassythoides - is this orchid saprophytic or parasitic?
Dearnaley, John. 2006. "The fungal endophytes of erythrorchis cassythoides - is this orchid saprophytic or parasitic?" Australasian Mycologist. 25 (2), pp. 51-57.
The fungal endophytes of dipodium variegatum (orchidaceae)
Bougoure, Jeremy J. and Dearnaley, John. 2005. "The fungal endophytes of dipodium variegatum (orchidaceae)." Australasian Mycologist. 24 (1), pp. 15-19.
ITS-RFLP and sequence analysis of endophytes from Acianthus, Caladenia and Pterostylis (orchidaceae) in southeastern Queensland
Bougoure, Jeremy J., Bougoure, Damian S., Cairney, John W. G. and Dearnaley, John D. W.. 2005. "ITS-RFLP and sequence analysis of endophytes from Acianthus, Caladenia and Pterostylis (orchidaceae) in southeastern Queensland." Mycological Research. 109 (4), pp. 452-460. https://doi.org/10.1017/S095375620500225X
Isochromophilone IX, a novel GABA-containing metabolite isolated from a cultured fungus, Penicillium sp.
Michael, Adam P., Grace, Emily J., Kotiw, Michael and Barrow, Russell A.. 2003. "Isochromophilone IX, a novel GABA-containing metabolite isolated from a cultured fungus, Penicillium sp." Australian Journal of Chemistry: an international journal for chemical science. 56 (1), pp. 13-15. https://doi.org/10.1071/CH02021