Chris Ireland and Lab

Chris Ireland

Professor of Medicinal Chemistry

 

CONTACT

Phone: 801.581.8305

Email: chris.ireland@utah.edu

Education

  • Ph.D. Scripps Institution of Oceanography 1977

  • B.A. University of California, San Diego 1973

Research Interests

Ireland Lab Summary

The Ireland research group is part of the Department of Medicinal Chemistry and is led by Chris Ireland. The main focus of our research group is the study of marine natural products and their biological activities. In particular our group has extensively studied the chemistry of marine invertebrates such as sponges and ascidians. These organisms have proven to be a prolific source of diverse chemical structures with potential anticancer use.

Our group has multidisciplinary interests and studies several aspects of marine natural products including isolation, structure elucidation, synthesis, mechanism of action, and structure-activity relationships. In all projects our end goal is the discovery of compounds having potential benefit in the treatment of disease or the understanding of biological systems implicated in disease. Our group participates in the Biological Chemistry Program.

cop orange sponge ireland lab

Rationale

molecule model orange ireland lab

Our research focuses on the isolation and structure determination of compounds from marine invertebrates, the detection of their effects on biological systems, and the characterization of their mode of action and structural determinants contributing to their biological activity. Our emphasis on organisms from tropical reefs is based on the hypothesis that competitive environments select for potent biological activities. Reefs are highly diverse ecosystems that are subject to a variety of selective mechanisms such as predation, fouling by microorganisms, and limited benthic substrates for settlement of sessile organisms. A common strategy for competing in such environments adopted by several organisms that are structurally vulnerable to these pressures is the production or accumulation of chemicals that can be used defensively or offensively.

Although the human body and its pathogens are foreign to a typical marine community, many of the biological pathways implicated in diseases such as cancer, infection, and autoimmune disorders are similar enough to those of competitors in tropical reefs that high potency of biological activity is frequently found in marine natural products. While the ecological roles of most marine natural products are unknown, the high potency and selectivity observed in marine natural products and the observation that structure-activity relationships are often highly optimized in marine natural products suggests that acquiring and maintaining high potency in these systems is a dominant selective pressure acting on their biosynthetic pathways. Add in the fact that marine invertebrates often host diverse and complex microbial communities where invasive disruption on a short time scale is a distinct possibility and that sponges and, to a lesser extent, ascidians have long evolutionary histories among the metazoans and it is no wonder that such potent compounds are to be found in these organisms.

Approach

Given our broad interests in marine natural products and their biological activities our group has adopted an approach that is both multidisciplinary and collaborative. The basis for most of our work is purifying compounds using predominantly chromatography and other chemical techniques and characterizing their structures using various analytical techniques including one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV) spectrophotometry, and chemical modification. Structure determination is a challenging but rewarding process that requires careful experimental technique, the ability to organize and correlate disparate items of data, and extensive consultation of structure databases and the chemical literature.

blue sponge ireland lab

However, making natural product discoveries of high significance demands a broader skill set. There is a need for innovative biological screens to maximize the potential of finding compounds with biomedical value. In order to reduce the likelihood of rediscovering a known compound with a previously documented biological activity, high-throughput assays and high-throughput analytical processes must be coordinated with an efficient dereplication process. Determining the mechanism of action for an agent is necessary before it will be of use as a therapeutic or biochemical tool. Chemical synthesis or modification is often needed to fully characterize a structure or determine structure-activity relationships (SAR).

molecule model blue ireland lab

The usual path for graduate students in the Ireland research group starts with projects involving the isolation and identification of compounds associated with biological activity as detected through screening. The student will then identify a central topic of research involving a marine natural product family or scaffold for which there are pressing questions regarding their structure or activities. They will formulate a plan for studying this topic that often involves working in the laboratory of collaborators to develop the skills needed for proving or refuting their central hypotheses. In the course of doing this, past group members have generally developed an outlook where the scientific problem itself, rather than the techniques known by the researcher, direct the path of study on new projects.

Lab Information

Ryan Van Wagoner

Location: 309 Skaggs Hall

Phone: 801-581-4932

Mary Kay Harper

Location: 309 Skaggs Hall

Phone: 801-581-4932

Xiaomei Wei

Location: 309 Skaggs Hall

Phone: 801-581-4932

Zhenyu Lu

Location: 309 Skaggs Hall

Phone: 801-581-4932

Opportunities

Positions Available

Our laboratory has opportunities in undergraduate and graduate research. If you are interested in joining the Ireland lab, please email Dr. Van Wagoner. Students considering graduate research in the Ireland laboratory are encouraged to contact Dr. Van Wagoner and to check out the Biological Chemistry Program.

Highlights

Phenotypic Activity of Pyridoacridines in Zebrafish

In collaboration with Ireland group alumnus Dr. Imelda Sandoval in the David Jones research laboratory, fraction libraries from marine invertebrates were screened for phenotypic activity in embryos of the zebrafish Danio rerio. The fraction library was generated using protocols developed in the Ireland laboratory that allow high-throughput fractionation of crude extracts. (references 1–2) The screens identified extracts from Xestospongia cf. carbonaria (Figure 1) as causing abnormal notochord development (Figure 2).

marine sponge xestospongia
Figure 1. An example of the marine sponge Xestospongia
cop ireland lab zebrafish embryos
Figure 2. Phenotypic abnormalities elicited by fractions from Xestospongia cf. carbonaria in zebrafish embryos. Top– Control. Bottom– Treated embryos. Note abnormalities in backbone and in the size of the yolk sac.

Based on these observations, extraction and isolation was carried out on Xestospongia cf. carbonaria by Dr. Xiaomei Wei. This work led to the isolation of several pyridoacridines, a family of heterocyclic natural products from numerous marine animals that have been noted for disrupting the process of DNA replication. (reference 3) The compounds isolated included amphimedine (1), (reference 4) neoamphimedine (2), (reference 5) and several minor congeners (Figure 3). Interestingly, the two regioisomers 1 and 2 displayed differential activity in the zebrafish assay: Only 1 was capable of eliciting the originally observed phenotype whereas 2 caused death and no additional phenotypes at sublethal doses. It is interesting to note that 2 exhibits activity mediated by topoisomerase II whereas 1 does not. (reference 6) This work was recently published in the journal Marine Drugs. (reference 7)

pyridoacridines ireland lab
Figure 3. The two major pyridoacridines isolated from Xestospongia cf. carbonaria amphimedine (1) and neoamphimedine (2).

Collaborating Groups and Professional Societies

Collaborating Groups

  • Lou Barrows- Our lab are coinvestigators on Professor Barrows's International Cooperative Biodiversity Grant focusing on Papua New Guinea.
  • David Bearss- Professor Bearss's lab and ours maintain a library of natural products available to researchers at the Huntsman Cancer Institute.
  • David Jones- We have had many ongoing collaborations with Professor Jones on exploring the mechanism of action of marine natural products. Our most recent collaborations involve screening for phenotypic activities in zebrafish larvae.

Professional Societies

  • American Society of Pharmacognosy- This is the largest American organization dedicated to natural product research. In conjunction with the American Chemical Society, the ASP provides editorial support for the Journal of Natural Products, the premiere publication in natural product research.
  • American Chemical Society- The ACS organizes regional and national meetings for the dissemination of chemical knowledge. They also publish many high profile journals in the field of chemistry.

Publications

    Peer-Reviewed Publications, Book Chapters, and Patents

    Peer-reviewed Articles

    2010-2019

    1. Z. Lu, R. M. Van Wagoner, M. K. Harper, J. N. A. Hooper, C. M. Ireland "Two ring-A-aromatized bile acids from the marine sponge Sollasella moretonensis." Natural Product Communications, 2010, 5, 1571–1574.

    2. M. Koch, T. S. Bugni, M. Sondossi, C. M. Ireland, L. R. Barrows "Exocarpic acid inhibits mycolic acid biosynthesis in Mycobacterium tuberculosis." Planta Medica, 2010, 76, 1678–1682.

    3. X. Wei, T. S. Bugni, M. K. Harper, I. T. Sandoval, E. J. Manos, J. Swift, R. M. Van Wagoner, D. A. Jones, C. M. Ireland "Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay." Marine Drugs, 2010, 8, 1769–1778. Online Text

    4. S. M. Pimentel-Elardo, S. Kozytska, T. S. Bugni, C. M. Ireland, H. Moll and U. Hentschel "Anti-parasitic compounds from Streptomyces sp. strains isolated from Mediterranean sponges." Marine Drugs, 2010, 8, 373–380. Online Text

    2000-2009

    1. T. S. Bugni, C. D. Andjelic, A. R. Pole, P. Rai, C. M. Ireland and L. R. Barrows "Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation." Fitoterapia, 2009, 80, 270–273.

    2. M. Koch, T. S. Bugni, C. D. Pond, M. Sondossi, M. Dindi, P. Piskaut, C. M. Ireland and L. R. Barrows "Antimycobacterial activity of Exocarpos latifolius is due to exocarpic acid." Planta Medica, 2009, 75, 1326–1330.

    3. D. V. La Barbera, K. Modzelewska, A. I. Glazar, P. D. Gray, M. Kaur, T. Liu, D. Grossman, M. K. Harper, S. K. Kuwada, N. Moghal and C. M. Ireland "The marine alkaloid naamidine A promotes caspase-dependent apoptosis in tumor cells." Anti-Cancer Drugs, 2009, 20, 425–436.

    4. K. M. Marshall, C. D. Andjelic, D. Tasdemir, G. P. Concepcion, C. M. Ireland and L. R. Barrows "Deoxyamphimedine, a pyridoacridine alkaloid, damages DNA via the production of reactive oxygen species." Marine Drugs, 2009, 7, 196–209. Online Text

    5. M. W. B. McCulloch, G. S. Coombs, N. Banerjee, T. S. Bugni, K. M. Cannon, M. K. Harper, C. A. Veltri, D. M. Virshup and C. M. Ireland "Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives." Bioorganic & Medicinal Chemistry, 2009, 17, 2189–2198.

    6. M. W. B. McCulloch, T. S. Bugni, G. P. Concepcion, G. S. Coombs, M. K. Harper, S. Kaur, G. C. Mangalindan, M. M. Mutizwa, C. A. Veltri, D. M. Virshup and C. M. Ireland "Carteriosulfonic Acids A-C, GSK-3β Inhibitors from a Carteriospongia sp." Journal of Natural Products, 2009, 72, 1651–1656.

    7. E. L. Whitson, A. S. Ratnayake, T. S. Bugni, M. K. Harper and C. M. Ireland "Isolation, Structure Elucidation, and Synthesis of Eudistomides A and B, Lipopeptides from a Fijian Ascidian Eudistoma sp." Journal of Organic Chemistry, 2009, 74, 1156–1162.

    8. E. L. Whitson, T. S. Bugni, P. S. Chockalingam, G. P. Concepcion, X. Feng, G. Jin, M. K. Harper, G. C. Mangalindan, L. A. McDonald and C. M. Ireland "Fibrosterol Sulfates from the Philippine Sponge Lissodendoryx (Acanthodoryx) fibrosa: Sterol Dimers that Inhibit PKCζ." Journal of Organic Chemistry, 2009, 74, 5902–5908.

    9. T. S. Bugni, B. Richards, L. Bhoite, D. Cimbora, M. K. Harper and C. M. Ireland "Marine Natural Product Libraries for High-Throughput Screening and Rapid Drug Discovery." Journal of Natural Products, 2008, 71, 1095–1098.

    10. T. S. Bugni, M. K. Harper, M. W. B. McCulloch, J. Reppart and C. M. Ireland "Fractionated marine invertebrate extract libraries for drug discovery." Molecules, 2008, 13, 1372–1383. Online Text

    11. K. A. Mohammed, R. C. Jadulco, T. S. Bugni, M. K. Harper, M. Sturdy and C. M. Ireland "Strongylophorines: Natural Product Inhibitors of Hypoxia-Inducible Factor-1 Transcriptional Pathway." Journal of Medicinal Chemistry, 2008, 51, 1402–1405.

    12. J. C. Noro, L. R. Barrows, O. G. Gideon, C. M. Ireland, M. Koch, T. Matainaho, P. Piskaut, C. D. Pond and T. S. Bugni "Tetrahdroxysqualene from Rhus taitensis Shows Antimycobacterial Activity against Mycobacterium tuberculosis." Journal of Natural Products, 2008, 71, 1623–1624.

    13. E. L. Whitson, T. S. Bugni, P. S. Chockalingam, G. P. Concepcion, M. K. Harper, M. He, J. N. A. Hooper, G. C. Mangalindan, F. Ritacco and C. M. Ireland "Spheciosterol Sulfates, PKCζ Inhibitors from a Philippine Sponge Spheciospongia sp." Journal of Natural Products, 2008, 71, 1213–1217.

    14. H. Hoang, D. V. La Barbera, K. A. Mohammed, C. M. Ireland and E. B. Skibo "Synthesis and Biological Evaluation of Imidazoquinoxalinones, Imidazole Analogues of Pyrroloiminoquinone Marine Natural Products." Journal of Medicinal Chemistry, 2007, 50, 4561–4571.

    15. D. V. La Barbera, T. S. Bugni and C. M. Ireland "The Total Synthesis of Neoamphimedine." Journal of Organic Chemistry, 2007, 72, 8501–8505.

    16. D. W. Laird, D. V. La Barbera, X. Feng, T. S. Bugni, M. K. Harper and C. M. Ireland "Halogenated Cyclic Peptides Isolated from the Sponge Corticium sp." Journal of Natural Products, 2007, 70, 741–746.

    17. A. A. Sertan-de Guzman, R. Z. Predicala, E. B. Bernardo, B. A. Neilan, S. P. Elardo, G. C. Mangalindan, D. Tasdemir, C. M. Ireland, W. L. Barraquio and G. P. Concepcion "Pseudovibrio denitrificans strain Z143-1, a heptylprodigiosin-producing bacterium isolated from a Philippine tunicate." FEMS Microbiology Letters, 2007, 277, 188–196.

    18. M. D. Alexander, M. D. Burkart, M. S. Leonard, P. Portonovo, B. Liang, X. Ding, M. M. Joullie, B. M. Gulledge, J. B. Aggen, A. R. Chamberlin, J. Sandler, W. Fenical, J. Cui, S. J. Gharpure, A. Polosukhin, H.-R. Zhang, P. A. Evans, A. D. Richardson, M. K. Harper, C. M. Ireland, B. G. Vong, T. P. Brady, E. A. Theodorakis and J. J. La, Clair "A central strategy for converting natural products into fluorescent probes." ChemBioChem, 2006, 7, 409–416.

    19. C. Chevallier, T. S. Bugni, X. Feng, M. K. Harper, A. M. Orendt and C. M. Ireland "Tedanolide C: A potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp." Journal of Organic Chemistry, 2006, 71, 2510–2513.

    20. J. E. H. Lazaro, J. Nitcheu, N. Mahmoudi, J. A. Ibana, G. C. Mangalindan, G. P. Black, A. G. Howard-Jones, C. G. Moore, D. A. Thomas, D. Mazier, C. M. Ireland, G. P. Concepcion, P. J. Murphy and B. Diquet "Antimalarial activity of crambescidin 800 and synthetic analogues against liver and blood stage of Plasmodium sp." Journal of Antibiotics, 2006, 59, 583–590.

    21. S. P. Lira, A. M. Vita-Marques, M. H. R. Seleghim, T. S. Bugni, D. V. La Barbera, L. D. Sette, S. R. P. Sponchiado, C. M. Ireland and R. G. S. Berlinck "New destruxins from the marine-derived fungus Beauveria felina." Journal of Antibiotics, 2006, 59, 553–563.

    22. A. S. Ratnayake, T. S. Bugni, C. A. Veltri, J. J. Skalicky and C. M. Ireland "Chemical Transformation of Prostaglandin-A2: A Novel Series of C-10 Halogenated, C-12 Hydroxylated Prostaglandin-A2 Analogues." Organic Letters, 2006, 8, 2171–2174.

    23. A. S. Ratnayake, T. S. Bugni, X. Feng, M. K. Harper, J. J. Skalicky, K. A. Mohammed, C. D. Andjelic, L. R. Barrows and C. M. Ireland "Theopapuamide, a Cyclic Depsipeptide from a Papua New Guinea Lithistid Sponge Theonella swinhoei." Journal of Natural Products, 2006, 69, 1582–1586.

    24. D. N. Shelton, I. T. Sandoval, A. Eisinger, S. Chidester, A. Ratnayake, C. M. Ireland and D. A. Jones "Up-regulation of CYP26A1 in adenomatous polyposis coli-deficient vertebrates via a WNT-dependent mechanism: implications for intestinal cell differentiation and colon tumor development." Cancer Research, 2006, 66, 7571–7577.

    25. E. L. Whitson, S. M. V. Damayanthi, Mala, C. A. Veltri, T. S. Bugni, E. Dilip, de Silva and C. M. Ireland "Oppositines A and B, Sesquiterpene Pyridine Alkaloids from a Sri Lankan Pleurostylia opposita." Journal of Natural Products, 2006, 69, 1833–1835.

    26. M.-G. Dijoux, P. C. Schnabel, Y. F. Hallock, J. L. Boswell, T. R. Johnson, J. A. Wilson, C. M. Ireland, R. van Soest, M. R. Boyd, L. R. Barrows and J. H. Cardellina "Antitumor activity and distribution of pyrroloiminoquinones in the sponge genus Zyzzya." Bioorganic & Medicinal Chemistry, 2005, 13, 6035–6044.

    27. J. E. Janso, V. S. Bernan, M. Greenstein, T. S. Bugni and C. M. Ireland "Penicillium dravuni, a new marine-derived species from an alga in Fiji." Mycologia, 2005, 97, 444–453.

    28. A. S. Ratnayake, R. A. Davis, M. K. Harper, C. A. Veltri, C. D. Andjelic, L. R. Barrows and C. M. Ireland "Aurantosides G, H, and I: Three new tetramic acid glycosides from a Papua New Guinea Theonella swinhoei." Journal of Natural Products, 2005, 68, 104–107.

    29. A. D. Richardson, W. Aalbersberg and C. M. Ireland "The patellazoles inhibit protein synthesis at nanomolar concentrations in human colon tumor cells." Anti-Cancer Drugs, 2005, 16, 533–541.

    30. R. J. Andersen, C. M. Ireland, T. F. Molinski and C. A. Bewley "Research Achievement Award-D. John Faulkner." Journal of Natural Products, 2004, 67, 1239–1251.

    31. T. S. Bugni and C. M. Ireland "Marine-derived fungi: a chemically and biologically diverse group of microorganisms." Natural Product Reports, 2004, 21, 143–163.

    32. T. S. Bugni, J. E. Janso, R. T. Williamson, X. Feng, V. S. Bernan, M. Greenstein, G. T. Carter, W. M. Maiese and C. M. Ireland "Dictyosphaeric acids A and B: new decalactones from an undescribed Penicillium sp. obtained from the alga Dictyosphaeria versluyii." Journal of Natural Products, 2004, 67, 1396–1399.

    33. T. S. Bugni, M. P. Singh, L. Chen, D. A. Arias, M. K. Harper, M. Greenstein, W. M. Maiese, G. P. Concepcion, G. C. Mangalindan and C. M. Ireland "Kalihinols from two Acanthella cavernosa sponges: inhibitors of bacterial folate biosynthesis." Tetrahedron, 2004, 60, 6981–6988.

    34. R. A. Davis, G. C. Mangalindan, Z. P. Bojo, R. R. Antemano, N. O. Rodriguez, G. P. Concepcion, S. C. Samson, D. De Guzman, L. J. Cruz, D. Tasdemir, M. K. Harper, X. Feng, G. T. Carter and C. M. Ireland "Microcionamides A and B, bioactive peptides from the Philippine sponge Clathria (Thalysias) abietina." Journal of Organic Chemistry, 2004, 69, 4170–4176.

    35. M. K. Harper, C. M. Ireland and R. K. Okuda "Special Issue in Honor of D. John Faulkner and Paul J. Scheuer." Journal of Natural Products, 2004, 67, 1201–1203.

    36. C. Jette, P. W. Peterson, I. T. Sandoval, E. J. Manos, E. Hadley, C. M. Ireland and D. A. Jones "The Tumor Suppressor Adenomatous Polyposis Coli and Caudal Related Homeodomain Protein Regulate Expression of Retinol Dehydrogenase L." Journal of Biological Chemistry, 2004, 279, 34397–34405.

    37. A. D. Richardson and C. M. Ireland "A profile of the in vitro antitumor activity of lissoclinolide." Toxicology and Applied Pharmacology, 2004, 195, 55–61.

    38. I. T. Sandoval, R. A. Davis, T. S. Bugni, G. P. Concepcion, M. K. Harper and C. M. Ireland "Cytotoxic isoquinoline quinones from sponges of the genus Petrosia." Natural Product Research, 2004, 18, 89–93.

    39. S. M. Verbitski, J. E. Mullally, F. A. Fitzpatrick and C. M. Ireland "Punaglandins, chlorinated prostaglandins, function as potent michael receptors to inhibit ubiquitin isopeptidase activity." Journal of Medicinal Chemistry, 2004, 47, 2062–2070.

    40. H. Abou, Gazar, D. Tasdemir, C. M. Ireland and I. Calis "Irinoids and triterpene saponins from Verbascum wiedemannianum." Biochemical Systematics and Ecology, 2003, 31, 433–436.

    41. T. S. Bugni, V. S. Bernan, M. Greenstein, J. E. Janso, W. M. Maiese, C. L. Mayne and C. M. Ireland "Brocaenols A-C: Novel polyketides from a marine-derived Penicillium brocae." Journal of Organic Chemistry, 2003, 68, 2014–2017.

    42. T. S. Bugni, V. S. Bernan, M. Greenstein, J. E. Janso, W. M. Maiese, C. L. Mayne and C. M. Ireland "Brocaenols A-C: Novel Polyketides from a Marine-Derived Penicillium brocae." Journal of Organic Chemistry, 2003, 68, –6846.

    43. C. Chevallier, A. D. Richardson, M. C. Edler, E. Hamel, M. K. Harper and C. M. Ireland "A New cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp." Organic Letters, 2003, 5, 3737–3739.

    44. R. A. Davis, I. T. Sandoval, G. P. Concepcion, R. Moreira, da Rocha and C. M. Ireland "Lissoclinotoxins E and F, novel cytotoxic alkaloids from a Philippine didemnid ascidian." Tetrahedron, 2003, 59, 2855–2859.

    45. R. A. Davis, L. V. Christensen, A. D. Richardson, R. Moreira, da Rocha and C. M. Ireland "Rigidin E, a new pyrrolopyrimidine alkaloid from a Papua New Guinea tunicate Eudistoma species." Marine Drugs, 2003, 1, 27–33. Online Text

    46. C. Ireland, W. Aalbersberg, R. Andersen, S. Ayral-Kaloustian, R. Berlinck, V. Bernan, G. Carter, A. Churchill, J. Clardy, G. Concepcion, D. De Silva, C. Discafani, T. Fojo, P. Frost, D. Gibson, L. Greenberger, M. Greenstein, M. K. Harper, R. Mallon, F. Loganzo, M. Nunes, M. Poruchynsky and A. Zask "Anticancer agents from unique natural products surces." Pharmaceutical Biology (Lisse, Netherlands), 2003, 41, 15–38.

    47. R. D. James, D. A. Jones, W. Aalbersberg and C. M. Ireland "Naamidine A Intensifies the Phosphotransferase Activity of Extracellular Signal-regulated Kinases Causing A-431 Cells to Arrest in G1." Molecular Cancer Therapeutics, 2003, 2, 747–751.

    48. K. M. Marshall, S. S. Matsumoto, J. A. Holden, G. P. Concepcion, D. Tasdemir, C. M. Ireland and L. R. Barrows "The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine." Biochemical Pharmacology, 2003, 66, 447–458.

    49. S. M. V. Pimentel, Z. P. Bojo, A. V. D. Roberto, J. E. H. Lazaro, G. C. Mangalindan, L. M. Florentino, P. Lim-Navarro, D. Tasdemir, C. M. Ireland and G. P. Concepcion "Platelet Aggregation Inhibitors from Philippine Marine Invertebrate Samples Screened in a New Microplate Assay." Marine Biotechnology, 2003, 5, 395–400.

    50. D. Tasdemir, T. S. Bugni, G. C. Mangalindan, G. P. Concepcion, M. K. Harper and C. M. Ireland "Bisabolane type sesquiterpenes from a marine Didiscus sponge." Turkish Journal of Chemistry, 2003, 27, 273–279.

    51. R. M. Van Wagoner and C. M. Ireland "An Improved Solution Structure for ψ-Conotoxin PIIIE." Biochemistry, 2003, 42, 6347–6352.

    52. R. M. Van Wagoner, R. B. Jacobsen, B. M. Olivera and C. M. Ireland "Characterization and Three-Dimensional Structure Determination of ψ-Conotoxin PIIIF, a Novel Noncompetitive Antagonist of Nicotinic Acetylcholine Receptors." Biochemistry, 2003, 42, 6353–6362.

    53. T. S. Bugni, G. P. Concepcion, G. C. Mangalindan, M. K. Harper, R. D. James and C. M. Ireland "p-Sulfooxyphenylpyruvic acid from the red macro alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis." Phytochemistry, 2002, 60, 361–363.

    54. I. Calis, H. Kirmizibekmez, D. Tasdemir and C. M. Ireland "Iridoid glycosides from Globularia davisiana." Chemical & Pharmaceutical Bulletin, 2002, 50, 678–680.

    55. I. Calis, D. Tasdemir, C. M. Ireland and O. Sticher "Lucidin type anthraquinone glycosides from Putoria calabrica." Chemical & Pharmaceutical Bulletin, 2002, 50, 701–702.

    56. I. Calis, H. Kirmizibekmez, D. Tasdemir, O. Sticher and C. M. Ireland "Sugar esters from Globularia orientalis." Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 2002, 57, 591–596.

    57. R. A. Davis, W. Aalbersberg, S. Meo, R. Moreira, da Rocha and C. M. Ireland "The isolation and synthesis of polyandrocarpamines A and B. Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp." Tetrahedron, 2002, 58, 3263–3269.

    58. M. C. Edler, A. M. Fernandez, P. Lassota, C. M. Ireland and L. R. Barrows "Inhibition of tubulin polymerization by vitilevuamide, a bicyclic marine peptide, at a site distinct from colchicine, the vinca alkaloids, and dolastatin 10." Biochemical Pharmacology, 2002, 63, 707–715.

    59. T. Ersoz, M. Z. Berkman, D. Tasdemir, I. Calis and C. M. Ireland "Iridoid and phenylethanoid glycosides from Euphrasia pectinata." Turkish Journal of Chemistry, 2002, 26, 179–188.

    60. T. Ersoz, I. Saracoglu, D. Tasdemir, H. Kirmizibekmez, A. A. Donmez, C. M. Ireland and I. Calis "Neolignan glucosides from Phlomis chimerae Boiss." Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 2002, 57, 221–225.

    61. T. Ersoz, D. Tasdemir, I. Calis and C. M. Ireland "Phenylethanoid glycosides from Scutellaria galericulata." Turkish Journal of Chemistry, 2002, 26, 465–471.

    62. H. Kirmizibekmez, D. Tasdemir, T. Ersoz, C. M. Ireland and I. Calis "A new pregnane glycoside and a furostanol glycoside from Digitalis cariensis." Pharmazie, 2002, 57, 716–720.

    63. D. Tasdemir, R. Mallon, M. Greenstein, L. R. Feldberg, S. C. Kim, K. Collins, D. Wojciechowicz, G. C. Mangalindan, G. P. Concepcion, M. K. Harper and C. M. Ireland "Aldisine Alkaloids from the Philippine Sponge Stylissa massa Are Potent Inhibitors of Mitogen-Activated Protein Kinase Kinase-1 (MEK-1)." Journal of Medicinal Chemistry, 2002, 45, 529–532.

    64. D. Tasdemir, G. C. Mangalindan, G. P. Concepcion, S. M. Verbitski, S. Rabindran, M. Miranda, M. Greenstein, J. N. A. Hooper, M. K. Harper and C. M. Ireland "Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata." Journal of Natural Products, 2002, 65, 210–214.

    65. D. Tasdemir, T. S. Bugni, G. C. Mangalindan, G. P. Concepcion, M. K. Harper and C. M. Ireland "Cytotoxic bromoindole derivatives and terpenes from the Philippine marine sponge Smenospongia sp." Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 2002, 57, 914–922.

    66. Y. R. Torres, T. S. Bugni, R. G. S. Berlinck, C. M. Ireland, A. Magalhaes, A. G. Ferreira and R. Moreira, da Rocha "Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei." Journal of Organic Chemistry, 2002, 67, 5429–5432.

    67. S. M. Verbitski, C. L. Mayne, R. A. Davis, G. P. Concepcion and C. M. Ireland "Isolation, structure determination, and biological activity of a novel alkaloid, perophoramidine, from the Philippine ascidian Perophora namei." Journal of Organic Chemistry, 2002, 67, 7124–7126.

    68. I. Calis, J. Heilmann, D. Tasdemir, A. Linden, C. M. Ireland and O. Sticher "Flavonoid, iridoid, and lignan glycosides from Putoria calabrica." Journal of Natural Products, 2001, 64, 961–964.

    69. H. He, W.-D. Ding, V. S. Bernan, A. D. Richardson, C. M. Ireland, M. Greenstein, G. A. Ellestad and G. T. Carter "Lomaiviticins A and B, Potent Antitumor Antibiotics from Micromonospora lomaivitiensis." Journal of the American Chemical Society, 2001, 123, 5362–5363.

    70. D. Tasdemir, K. M. Marshall, G. C. Mangalindan, G. P. Concepcion, L. R. Barrows, M. K. Harper and C. M. Ireland "Deoxyamphimedine, a new pyridoacridine alkaloid from two tropical Xestospongia sponges." Journal of Organic Chemistry, 2001, 66, 3246–3248.

    71. D. Tasdemir, G. P. Concepcion, G. C. Mangalindan, M. K. Harper, E. Hajdu and C. M. Ireland "Corrigendum to "New Terpenoids from a Cacospongia sp. from the Philippines" [Tetrahedron 56 (2000) 9025-9030]." Tetrahedron, 2001, 57, –5681.

    72. D. Tasdemir, G. C. Mangalindan, G. P. Concepcion, M. K. Harper and C. M. Ireland "3,7-Dimethylguanine, a new purine from a Philippine sponge Zyzzya fuliginosa." Chemical & Pharmaceutical Bulletin, 2001, 49, 1628–1630.

    73. R. M. Van Wagoner, J. Jompa, A. Tahir and C. M. Ireland "A novel modified pterin from a Eudistoma species ascidian." Journal of Natural Products, 2001, 64, 1100–1101.

    74. T. S. Bugni, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein, R. M. Van Wagoner and C. M. Ireland "Yanuthones: novel metabolites from a marine isolate of Aspergillus niger." Journal of Organic Chemistry, 2000, 65, 7195–7200.

    75. T. Ersoez, M. Z. Berkman, D. Tasdemir, C. M. Ireland and I. Calis "An iridoid glucoside from Euphrasia pectinata." Journal of Natural Products, 2000, 63, 1449–1450.

    76. G. C. Mangalindan, M. T. Talaue, L. J. Cruz, S. G. Franzblau, L. B. Adams, A. D. Richardson, C. M. Ireland and G. P. Concepcion "Agelasine F from a Philippine Agelas sp. sponge exhibits in vitro antituberculosis activity." Planta Medica, 2000, 66, 364–365.

    77. C. J. Smith, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein, J. Jompa, A. Tahir and C. M. Ireland "Novel polyketide metabolites from a species of marine fungi." Journal of Natural Products, 2000, 63, 142–145.

    78. D. Tasdemir, G. P. Concepcion, G. C. Mangalindan, M. K. Harper, E. Hajdu and C. M. Ireland "New terpenoids from a Cacospongia sp. from the Philippines." Tetrahedron, 2000, 56, 9025–9030.

    1990-1999

    1. F. S. De Guzman, B. Carte, N. Troupe, D. J. Faulkner, M. K. Harper, G. P. Concepcion, G. C. Mangalindan, S. S. Matsumoto, L. R. Barrows and C. M. Ireland "Neoamphimedine: a new pyridoacridine topoisomerase II inhibitor which catenates DNA." Journal of Organic Chemistry, 1999, 64, 1400–1402.

    2. B. S. Lindsay, A. M. P. Almeida, C. J. Smith, R. G. S. Berlinck, R. M. d. Rocha and C. M. Ireland "6-Methoxy-7-methyl-8-oxoguanine, an unusual purine from the ascidian Symplegma rubra." Journal of Natural Products, 1999, 62, 1573–1575.

    3. S. S. Matsumoto, H. M. Haughey, D. M. Schmehl, D. A. Venables, C. M. Ireland, J. A. Holden and L. R. Barrows "Makaluvamines vary in ability to induce dose-dependent DNA cleavage via topoisomerase II interaction." Anti-Cancer Drugs, 1999, 10, 39–45.

    4. R. M. Van Wagoner, J. Jompa, A. Tahir and C. M. Ireland "Trypargine Alkaloids from a Previously Undescribed Eudistoma sp. Ascidian." Journal of Natural Products, 1999, 62, 794–797.

    5. F. S. De Guzman, B. R. Copp, C. L. Mayne, G. P. Concepcion, G. C. Mangalindan, L. R. Barrows and C. M. Ireland "Bolinaquinone: A Novel Cytotoxic Sesquiterpene Hydroxyquinone from a Philippine Dysidea Sponge." Journal of Organic Chemistry, 1998, 63, 8042–8044.

    6. B. R. Copp, C. R. Fairchild, L. Cornell, A. M. Casazza, S. Robinson and C. M. Ireland "Naamidine A Is an Antagonist of the Epidermal Growth Factor Receptor and an in Vivo Active Antitumor Agent." Journal of Medicinal Chemistry, 1998, 41, 3909–3911.

    7. B. R. Copp, J. Jompa, A. Tahir and C. M. Ireland "Styelsamines A-D: New Tetracyclic Pyridoacridine Alkaloids from the Indonesian Ascidian Eusynstyela latericius." Journal of Organic Chemistry, 1998, 63, 8024–8026.

    8. T. C. McKee, D. L. Galinis, L. K. Pannell, I. Cardellina, John H., J. Laakso, C. M. Ireland, L. Murray, R. J. Capon and M. R. Boyd "The Lobatamides, Novel Cytotoxic Macrolides from Southwestern Pacific Tunicates." Journal of Organic Chemistry, 1998, 63, 7805–7810.

    9. S. S. Mitchell, K. J. Shon, M. P. Foster, B. M. Olivera and C. M. Ireland "Three-Dimensional Solution Structure of Conotoxin ψ-PIIIE, an Acetylcholine Gated Ion Channel Antagonist." Biochemistry, 1998, 37, 1215–1220.

    10. C. J. Smith, R. L. Hettich, J. Jompa, A. Tahir, M. V. Buchanan and C. M. Ireland "Cadiolides A and B, new metabolites from an ascidian of the genus Botryllus." Journal of Organic Chemistry, 1998, 63, 4147–4150.

    11. T. A. Foderaro, L. R. Barrows, P. Lassota and C. M. Ireland "Bengacarboline, a new β-carboline from a marine ascidian Didemnum sp." Journal of Organic Chemistry, 1997, 62, 6064–6065.

    12. S. S. Mitchell, A. B. Whitehill, H. G. Trapido-Rosenthal and C. M. Ireland "Isolation and characterization of 1,3-dimethylisoguanine from the Bermudian sponge Amphimedon viridis." Journal of Natural Products, 1997, 60, 727–728.

    13. C. J. Smith, D. A. Venables, C. Hopmann, C. E. Salomon, J. Jompa, A. Tahir, D. J. Faulkner and C. M. Ireland "Plakinidine D, a new pyrroloacridine alkaloid from two ascidians of the genus Didemnum." Journal of Natural Products, 1997, 60, 1048–1050.

    14. D. A. Venables, L. R. Barrows, P. Lassota and C. M. Ireland "Veiutamine. A new alkaloid from the Fijian sponge Zyzzya fuliginosa." Tetrahedron Letters, 1997, 38, 721–722.

    15. D. A. Venables, G. P. Concepcion, S. S. Matsumoto, L. R. Barrows and C. M. Ireland "Makaluvamine N: a new pyrroloiminoquinone from Zyzzya fuliginosa." Journal of Natural Products, 1997, 60, 408–410.

    16. A. R. Carroll, J. C. Coll, D. J. Bourne, J. K. MacLeod, T. M. Zabriskie, C. M. Ireland and B. F. Bowden "Patellins 1-6 and trunkamide A: novel cyclic hexa-, hepta- and octa-peptides from colonial ascidians, Lissoclinum sp." Australian Journal of Chemistry, 1996, 49, 659–667.

    17. J. M. Kokoshka, C. M. Ireland and L. R. Barrows "Cell-Based Screen for Identification of Inhibitors of Tubulin Polymerization." Journal of Natural Products, 1996, 59, 1179–1182.

    18. J. M. Kokoshka, T. L. Capson, J. A. Holden, C. M. Ireland and L. R. Barrows "Differences in the topoisomerase I cleavage complexes formed by camptothecin and wakayin, a DNA-intercalating marine natural product." Anti-Cancer Drugs, 1996, 7, 758–765.

    19. S. S. Mitchell, K. J. Shon, B. Olivera and C. M. Ireland "NMR structures of conotoxins." Journal of Natural Toxins, 1996, 5, 191–208.

    20. S. S. Mitchell, S. C. Pomerantz, G. P. Concepcion and C. M. Ireland "Tubercidin analogs from the ascidian Didemnum voeltzkowi." Journal of Natural Products, 1996, 59, 1000–1001.

    21. G. P. Concepcion, T. A. Foderaro, G. S. Eldredge, E. Lobkovsky, J. Clardy, L. R. Barrows and C. M. Ireland "Topoisomerase II-Mediated DNA Cleavage by Adocia- and Xestoquinones from the Philippine Sponge Xestospongia sp." Journal of Medicinal Chemistry, 1995, 38, 4503–7.

    22. L. A. McDonald, J. C. Swersey, C. M. Ireland, A. R. Carroll, J. C. Coll, B. F. Bowden, C. R. Fairchild and L. Cornell "Botryllamides A-D, new brominated tyrosine derivatives from styelid ascidians of the genus Botryllus." Tetrahedron, 1995, 51, 5237–44.

    23. J.-F. Biard, C. Roussakis, J.-M. Kornprobst, D. Gouiffes-Barbin, J.-F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland and C. Debitus "Bistramides A, B, C, D, and K: a new class of bioactive cyclic polyethers from Lissoclinum bistratum." Journal of Natural Products, 1994, 57, 1336–45.

    24. L. A. McDonald, G. S. Eldredge, L. R. Barrows and C. M. Ireland "Inhibition of Topoisomerase II Catalytic Activity by Pyridoacridine Alkaloids from a Cystodytes sp. Ascidian: A Mechanism for the Apparent Intercalator-Induced Inhibition of Topoisomerase II." Journal of Medicinal Chemistry, 1994, 37, 3819–27.

    25. D. S. Swaffar, C. M. Ireland and L. R. Barrows "a rapid mechanism-based screen to detect potential anticancer agents." Anti-Cancer Drugs, 1994, 5, 15–23.

    26. J. C. Swersey, C. M. Ireland, L. M. Cornell and R. W. Peterson "Eusynstyelamide, a highly modified dimer peptide from the ascidian Eusynstyela misakiensis." Journal of Natural Products, 1994, 57, 842–5.

    27. J. A. Trischman, D. M. Tapiolas, P. R. Jensen, R. Dwight, W. Fenical, T. C. McKee, C. M. Ireland, T. J. Stout and J. Clardy "Salinamides A and B: anti-inflammatory depsipeptides from a marine streptomycete." Journal of the American Chemical Society, 1994, 116, 757–8.

    28. L. R. Barrows, C. Radisky, Derek, B. R. Copp, S. Swaffar, Diane, R. A. Kramer, R. L. Warters and C. M. Ireland "Makaluvamines, marine natural products, are active anti-cancer agents and DNA topo II inhibitors." Anti-Cancer Drug Design, 1993, 8, 333–47.

    29. V. S. Bernan, D. M. Roll, C. M. Ireland, M. Greenstein, W. M. Maiese and D. A. Steinberg "A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana." Journal of Antimicrobial Chemotherapy, 1993, 32, 539–50.

    30. M. P. Foster and C. M. Ireland "Nairaiamides A and B. Two novel di-proline heptapeptides isolated from a Fijian Lissoclinum bistratum ascidian." Tetrahedron Letters, 1993, 34, 2871–4.

    31. J. M. McIntosh, T. A. Foderaro, W. Li, C. M. Ireland and B. M. Olivera "Presence of serotonin in the venom of Conus imperialis." Toxicon, 1993, 31, 1561–6.

    32. D. C. Radisky, E. S. Radisky, L. R. Barrows, B. R. Copp, R. A. Kramer and C. M. Ireland "Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya." Journal of the American Chemical Society, 1993, 115, 1632–8.

    33. B. R. Copp, C. M. Ireland and L. R. Barrows "Psammaplysin C: a new cytotoxic dibromotyrosine-derived metabolite from the marine sponge Druinella (Psammaplysilla) purpurea." Journal of Natural Products, 1992, 55, 822–3.

    34. R. Dunkel, C. L. Mayne, M. P. Foster, C. M. Ireland, D. Li, N. L. Owen, R. J. Pugmire and D. M. Grant "Applications of the improved computerized analysis of 2D INADEQUATE spectra." Analytical Chemistry, 1992, 64, 3150–60.

    35. M. P. Foster, C. L. Mayne, R. Dunkel, R. J. Pugmire, D. M. Grant, J. M. Kornprobst, J. F. Verbist, J. F. Biard and C. M. Ireland "Revised structure of bistramide A (bistratene A): application of a new program for the automated analysis of 2D INADEQUATE spectra." Journal of the American Chemical Society, 1992, 114, 1110–11.

    36. M. P. Foster, G. P. Concepcion, G. B. Caraan and C. M. Ireland "Bistratamides C and D. Two new oxazole-containing cyclic hexapeptides isolated from a Philippine Lissoclinum bistratum ascidian." Journal of Organic Chemistry, 1992, 57, 6671–5.

    37. L. A. McDonald and C. M. Ireland "Patellamide E: a new cyclic peptide from the ascidian Lissoclinum patella." Journal of Natural Products, 1992, 55, 376–9.

    38. L. A. McDonald, M. P. Foster, D. R. Phillips, C. M. Ireland, A. Y. Lee and J. Clardy "Tawicyclamides A and B, new cyclic peptides from the Ascidian Lissoclinum patella: studies on the solution- and solid-state conformations." Journal of Organic Chemistry, 1992, 57, 4616–24.

    39. B. R. Copp, C. M. Ireland and L. R. Barrows "Wakayin: a novel cytotoxic pyrroloiminoquinone alkaloid from the ascidian Clavelina species." Journal of Organic Chemistry, 1991, 56, 4596–7.

    40. B. S. Davidson, T. F. Molinski, L. R. Barrows and C. M. Ireland "Varacin: a novel benzopentathiepin from Lissoclinum vareau that is cytotoxic toward a human colon tumor." Journal of the American Chemical Society, 1991, 113, 4709–10.

    41. J. C. Swersey, L. R. Barrows and C. M. Ireland "Mamanuthaquinone: an antimicrobial and cytotoxic metabolite of Fasciospongia sp." Tetrahedron Letters, 1991, 32, 6687–90.

    42. B. S. Davidson and C. M. Ireland "Lissoclinolide, the first non-nitrogenous metabolite from a Lissoclinum tunicate." Journal of Natural Products, 1990, 53, 1036–8.

    43. R. R. West, C. L. Mayne, C. M. Ireland, L. S. Brinen and J. Clardy "Plakinidines: cytotoxic alkaloid pigments from the Fijian sponge Plakortis sp." Tetrahedron Letters, 1990, 31, 3271–4.

    44. T. M. Zabriskie, M. P. Foster, T. J. Stout, J. Clardy and C. M. Ireland "Studies on the solution- and solid-state structure of patellin 2." Journal of the American Chemical Society, 1990, 112, 8080–4.

    1980-1989

    1. G. A. Charyulu, T. C. McKee and C. M. Ireland "Diplamine, a cytotoxic polyaromatic alkaloid from the tunicate Diplosoma sp." Tetrahedron Letters, 1989, 30, 4201–2.

    2. C. M. Ireland, T. F. Molinski, D. M. Roll, T. M. Zabriskie, T. C. McKee, J. C. Swersey and M. P. Foster "Natural product peptides from marine organisms." Bioorganic Marine Chemistry, 1989, 3, 1–46.

    3. T. C. McKee, C. M. Ireland, N. Lindquist and W. Fenical "The complete spectral assignment of didemnin B and nordidemnin B." Tetrahedron Letters, 1989, 30, 3053–6.

    4. T. F. Molinski and C. M. Ireland "Varamines A and B, new cytotoxic thioalkaloids from Lissoclinum vareau." Journal of Organic Chemistry, 1989, 54, 4256–9.

    5. T. M. Zabriskie and C. M. Ireland "The isolation and structure of modified bioactive nucleosides from Jaspis johnstoni." Journal of Natural Products, 1989, 52, 1353–6.

    6. N. Lindquist, W. Fenical, D. F. Sesin, C. M. Ireland, G. D. Van Duyne, C. J. Forsyth and J. Clardy "Isolation and structure determination of the didemnenones, novel cytotoxic metabolites from tunicates." Journal of the American Chemical Society, 1988, 110, 1308–9.

    7. T. F. Molinski and C. M. Ireland "Dysidazirine, a cytotoxic azacyclopropene from the marine sponge Dysidea fragilis." Journal of Organic Chemistry, 1988, 53, 2103–5.

    8. D. M. Roll, C. M. Ireland, H. S. M. Lu and J. Clardy "Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp." Journal of Organic Chemistry, 1988, 53, 3276–8.

    9. T. M. Zabriskie, C. L. Mayne and C. M. Ireland "Patellazole C: a novel cytotoxic macrolide from Lissoclinum patella." Journal of the American Chemical Society, 1988, 110, 7919–20.

    10. T. C. McKee and C. M. Ireland "Cytotoxic and antimicrobial alkaloids from the Fijian sponge Xestospongia caycedoi." Journal of Natural Products, 1987, 50, 754–6.

    11. R. M. Moriarty, D. M. Roll, Y. Y. Ku, C. Nelson and C. M. Ireland "A revised structure for the marine bromoindole derivative citorellamine." Tetrahedron Letters, 1987, 28, 749–52.

    12. D. M. Roll, J. E. Biskupiak, C. L. Mayne and C. M. Ireland "Muamvatin, a novel tricyclic spiro ketal from the Fijian mollusk Siphonaria normalis." Journal of the American Chemical Society, 1986, 108, 6680–2.

    13. D. F. Sesin, S. J. Gaskell and C. M. Ireland "The chemistry of Lissoclinum patella." Bulletin des Societes Chimiques Belges, 1986, 95, 853–67.

    14. T. M. Zabriskie, J. A. Klocke, C. M. Ireland, A. H. Marcus, T. F. Molinski, D. J. Faulkner, C. Xu and J. Clardy "Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity." Journal of the American Chemical Society, 1986, 108, 3123–4.

    15. J. E. Biskupiak and C. M. Ireland "Cytotoxic metabolites from the mollusc Peronia peronii." Tetrahedron Letters, 1985, 26, 4307–10.

    16. D. M. Roll and C. M. Ireland "Citorellamine, a new bromoindole derivative from Polycitorella mariae." Tetrahedron Letters, 1985, 26, 4303–6.

    17. J. E. Biskupiak and C. M. Ireland "Revised absolute configuration of dysidenin and isodysidenin." Tetrahedron Letters, 1984, 25, 2935–6.

    18. C. M. Ireland, J. E. Biskupiak, G. J. Hite, M. Rapposch, P. J. Scheuer and J. R. Ruble "Ilikonapyrone esters, likely defense allomones of the mollusk Onchidium verruculatum." Journal of Organic Chemistry, 1984, 49, 559–61.

    19. D. F. Sesin and C. M. Ireland "Iodinated phenethylamine products from a didemnid tunicate." Tetrahedron Letters, 1984, 25, 403–4.

    20. J. E. Biskupiak and C. M. Ireland "Absolute configuration of thiazole amino acids in peptides." Journal of Organic Chemistry, 1983, 48, 2302–4.

    21. J. E. Biskupiak and C. M. Ireland "Pectinatone, a new antibiotic from the mollusk Siphonaria pectinata." Tetrahedron Letters, 1983, 24, 3055–8.

    22. J. M. Wasylyk, J. E. Biskupiak, C. E. Costello and C. M. Ireland "Cyclic peptide structures from the tunicate Lissoclinum patella by FAB mass spectrometry." Journal of Organic Chemistry, 1983, 48, 4445–9.

    23. J. E. Hochlowski, R. P. Walker, C. Ireland and D. J. Faulkner "Metabolites of four nudibranchs of the genus Hypselodoris." Journal of Organic Chemistry, 1982, 47, 88–91.

    24. C. M. Ireland, J. Durso, Augustine R., R. A. Newman and M. P. Hacker "Antineoplastic cyclic peptides from the marine tunicate Lissoclinum patella." Journal of Organic Chemistry, 1982, 47, 1807–11.

    25. C. M. Ireland, J. Durso, Augustine R. and P. J. Scheuer "N,N'-diphenethylurea, a metabolite from the marine ascidian Didemnum ternatanum." Journal of Natural Products, 1981, 44, 360–1.

    26. C. Ireland and D. J. Faulkner "The metabolites of the marine mollusks Tridachiella diomedea and Tridachia crispata." Tetrahedron, Supplement, 1981, 233–40.

    27. C. Ireland and P. J. Scheuer "Ulicyclamide and ulithiacyclamide, two new small peptides from a marine tunicate." Journal of the American Chemical Society, 1980, 102, 5688–91.

    1970-1979

    1. C. Ireland, D. J. Faulkner, J. S. Finer and J. Clardy "Crispatone, a metabolite of the opisthobranch mollusc Tridachia crispata." Journal of the American Chemical Society, 1979, 101, 1275–6.

    2. C. Ireland and P. J. Scheuer "Photosynthetic marine mollusks: in vivo carbon-14 incorporation into metabolites of the sacoglossan Placobranchus ocellatus." Science (Washington, DC, United States), 1979, 205, 922–3.

    3. C. Ireland, D. J. Faulkner, B. A. Solheim and J. Clardy "Tridachione, a propionate-derived metabolite of the opisthobranch mollusc Tridachiella diomedea." Journal of the American Chemical Society, 1978, 100, 1002–3.

    4. C. Ireland and D. J. Faulkner "The defensive secretion of the opisthobranch mollusc Onchidella binneyi." Bioorganic Chemistry, 1978, 7, 125–31.

    5. D. J. Faulkner and C. Ireland "The chemistry of some opisthobranch molluscs." NATO Conference Series IV: Marine Sciences, 1977, 1, 23–34.

    6. C. Ireland and D. J. Faulkner "Diterpenes from Dolabella californica." Journal of Organic Chemistry, 1977, 42, 3157–62.

    7. C. Ireland, M. O. Stallard, D. J. Faulkner, J. Finer and J. Clardy "Some chemical constituents of the digestive gland of the sea hare Aplysia californica." Journal of Organic Chemistry, 1976, 41, 2461–5.

    8. C. Ireland, D. J. Faulkner, J. Finer and J. Clardy "A novel diterpene from Dollabella californica." Journal of the American Chemical Society, 1976, 98, 4664–5.

    9. D. J. Faulkner, M. O. Stallard and C. Ireland "Prepacifenol epoxide, a halogenated sesquiterpene diepoxide." Tetrahedron Letters, 1974, 3571–4.

    10. M. Ramenofsky, D. J. Faulkner and C. Ireland "Effect of juvenile hormone on cirriped metamorphosis." Biochemical and Biophysical Research Communications, 1974, 60, 172–8.

    11. E. D. Gomez, D. J. Faulkner, W. A. Newman and C. Ireland "Juvenile hormone mimics. Effect on cirriped crustacean metamorphosis." Science (Washington, DC, United States), 1973, 179, 813–14.

    Book Chapters and Monographs

    1. Bugni, T.S.; Ireland, C.M. "Marine-Derived Fungi: A Chemically and Biologically Diverse Group of Microorganisms" in Natural Products Reports, 2004, 21, 143-163.

    2. Harper, M.K.; Bugni, T.S.; Copp, B.R.; James, R.D.; Lindsay, B.S.; Richardson, A.D.; Schnabel, P.C.; Tasdemir, D.; VanWagoner, R.M.; Verbitski, S.M.; Ireland, C.M. "Introduction to the Chemical Ecology of Marine Natural Products" in J.B. McClintock and B.J. Baker (eds.), Marine Chemical Ecology, Boca Raton: CRC Press, 2001, pp. 3-69.

    3. Ireland, C.M.; Copp, B.R.; Foster, M.P.; McDonald, L.A.; Radisky, D.C.; Swersey, J.C. "Bioactive Compounds from the Sea" in R.E. Martin, E.P. Carter, L. M. Davis and G. J. Flick Jr. (eds.), Marine and Freshwater Products Handbook, Lancaster: Technomic Publishing, 2000, pp. 641-62.

    4. Ireland, C.M.; Copp, B.R.; Foster, M.P.; McDonald, L.A.; Radisky, D.C.; Swersey, J.C. "Biomedical Potential of Marine Natural Products" in D.H. Attaway and O.R. Zaborsky (eds.), Marine Biotechnology, Vol. 1. New York: Plenum Press, 1993, pp. 43.

    5. Ireland, C.M. "Marine Natural Products in the 21st Century: The Importance of Maintaining Bio-Diversity and Promoting Biotechnology for Developing Pharmaceuticals from the Sea" Environment, Science and Technology: The Challange of the 21st Century (Proceeding of The Second Princess Chulabhorn Science Congress, Vol. 1) Bangkok, Chulabhorn Research Institute, 1992, pp.539-50.

    6. Ireland, C. M.; Molinski, T. F.; Roll, D. M.; Zabriskie, T. M.; McKee, T. C.; Swersey, J. C. and Foster, M. P. "Natural Product Peptides from Marine Organisms." In P. J. Scheuer (ed.), Bioorganic Marine Chemistry, Vol. 3. New York: Springer-Verlag, 1989, pp. 46.

    7. Faulkner, D.J. and Ireland, C. "The Chemistry of Some Opisthobranch Molluscs." In D.J. Faulkner and W.H. Fenical (eds.), Marine Natural Products Chemistry. New York: Plenum Press, 1977, pp. 23.

    8. Ireland, C. "The Chemistry of Some Opisthobranch Molluscs." Ph.D. thesis, University of California, 1977, 137 pgs.

    Patents

    1. D. M. Virshup, G. Coombs, N. Banerjee and C. Ireland "Methods of cancer treatment using Wnt inhibitors, and compound identification methods." PCT Int. Appl., 2010, 70 pp.

    2. G. P. Concepcion, C. M. Ireland, G. C. Mangalindan, R. A. Davis, D. Tasdemir, Z. P. Boho, N. O. Rodriquez, D. R. Antemano, D. D. De, Guzman, S. C. Samson and M. K. Harper "Cyclic hexapeptides from Clathria marine sponge, process and use thereof." PCT Int. Appl., 2005, 24 pp.

    3. C. M. Ireland and A. Fernandez "Vitilevuamide, a cyclic peptide antitumor agent from the ascidians Didemnum cuculliferum and Polysyncraton lithostrotum." PCT Int. Appl., 1998, 36 pp.

    4. C. M. Ireland and W. M. Maiese "Namenamicin, an enediyne antitumor antibiotic from the marine ascidian Polysyncraton lithostrotum, and antitumor, antimicrobial, and DNA-cleaving activity thereof." PCT Int. Appl., 1997, 34 pp.

    5. C. M. Ireland, B. R. Copp and C. R. Fairchild "Naamidine A extracted from sea sponges and methods for its use as an anti-tumor agent." U.S., 1996, 11 pp., Cont. of U.S. Ser. No. 13,030.

    6. C. M. Ireland "Isolation of cytotoxic patellazoles." U.S., 1995, 7 pp. Cont. of Ser. No. 871,583.

    7. C. M. Ireland, D. C. Radisky, L. R. Barrows and R. Kramer "Antineoplastic pyrrolo[4,3,2-de]quinolin-8(1H)-ones." U.S., 1995, 33 pp. Cont. of U.S. Ser. No. 890, 989.