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Chris Ireland and Lab

Professor of Medicinal Chemistry

 

CONTACT

Phone: 801.581.8305

Fax: 801.585.6208

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

Research Lab Members

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 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 Communications20105, 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 Medica201076, 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 Drugs20108, 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 Drugs20108, 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." Fitoterapia200980, 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 Medica200975, 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 Drugs200920, 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 Drugs20097, 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 Chemistry200917, 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 Products200972, 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 Chemistry200974, 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 Chemistry200974, 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 Products200871, 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." Molecules200813, 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 Chemistry200851, 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 Products200871, 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 Products200871, 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 Chemistry200750, 4561–4571.

    15. D. V. La Barbera, T. S. Bugni and C. M. Ireland "The Total Synthesis of Neoamphimedine." Journal of Organic Chemistry200772, 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 Products200770, 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 Letters2007277, 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." ChemBioChem20067, 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 Chemistry200671, 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 Antibiotics200659, 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 Antibiotics200659, 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 Letters20068, 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 Products200669, 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 Research200666, 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 Products200669, 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 Chemistry200513, 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." Mycologia200597, 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 Products200568, 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 Drugs200516, 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 Products200467, 1239–1251.

    31. T. S. Bugni and C. M. Ireland "Marine-derived fungi: a chemically and biologically diverse group of microorganisms." Natural Product Reports200421, 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 Products200467, 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." Tetrahedron200460, 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 Chemistry200469, 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 Products200467, 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 Chemistry2004279, 34397–34405.

    37. A. D. Richardson and C. M. Ireland "A profile of the in vitro antitumor activity of lissoclinolide." Toxicology and Applied Pharmacology2004195, 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 Research200418, 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 Chemistry200447, 2062–2070.

    40. H. Abou, Gazar, D. Tasdemir, C. M. Ireland and I. Calis "Irinoids and triterpene saponins from Verbascum wiedemannianum." Biochemical Systematics and Ecology200331, 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 Chemistry200368, 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 Chemistry200368, –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 Letters20035, 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." Tetrahedron200359, 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 Drugs20031, 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)200341, 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 Therapeutics20032, 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 Pharmacology200366, 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 Biotechnology20035, 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 Chemistry200327, 273–279.

    51. R. M. Van Wagoner and C. M. Ireland "An Improved Solution Structure for ψ-Conotoxin PIIIE." Biochemistry200342, 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." Biochemistry200342, 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." Phytochemistry200260, 361–363.

    54. I. Calis, H. Kirmizibekmez, D. Tasdemir and C. M. Ireland "Iridoid glycosides from Globularia davisiana." Chemical & Pharmaceutical Bulletin200250, 678–680.

    55. I. Calis, D. Tasdemir, C. M. Ireland and O. Sticher "Lucidin type anthraquinone glycosides from Putoria calabrica." Chemical & Pharmaceutical Bulletin200250, 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 Biosciences200257, 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." Tetrahedron200258, 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 Pharmacology200263, 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 Chemistry200226, 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 Biosciences200257, 221–225.

    61. T. Ersoz, D. Tasdemir, I. Calis and C. M. Ireland "Phenylethanoid glycosides from Scutellaria galericulata." Turkish Journal of Chemistry200226, 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." Pharmazie200257, 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 Chemistry200245, 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 Products200265, 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 Biosciences200257, 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 Chemistry200267, 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 Chemistry200267, 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 Products200164, 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 Society2001123, 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 Chemistry200166, 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]." Tetrahedron200157, –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 Bulletin200149, 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 Products200164, 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 Chemistry200065, 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 Products200063, 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 Medica200066, 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 Products200063, 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." Tetrahedron200056, 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 Chemistry199964, 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 Products199962, 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 Drugs199910, 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 Products199962, 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 Chemistry199863, 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 Chemistry199841, 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 Chemistry199863, 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 Chemistry199863, 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." Biochemistry199837, 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 Chemistry199863, 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 Chemistry199762, 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 Products199760, 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 Products199760, 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 Letters199738, 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 Products199760, 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 Chemistry199649, 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 Products199659, 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 Drugs19967, 758–765.

    19. S. S. Mitchell, K. J. Shon, B. Olivera and C. M. Ireland "NMR structures of conotoxins." Journal of Natural Toxins19965, 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 Products199659, 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 Chemistry199538, 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." Tetrahedron199551, 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 Products199457, 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 Chemistry199437, 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 Drugs19945, 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 Products199457, 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 Society1994116, 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 Design19938, 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 Chemotherapy199332, 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 Letters199334, 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." Toxicon199331, 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 Society1993115, 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 Products199255, 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 Chemistry199264, 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 Society1992114, 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 Chemistry199257, 6671–5.

    37. L. A. McDonald and C. M. Ireland "Patellamide E: a new cyclic peptide from the ascidian Lissoclinum patella." Journal of Natural Products199255, 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 Chemistry199257, 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 Chemistry199156, 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 Society1991113, 4709–10.

    41. J. C. Swersey, L. R. Barrows and C. M. Ireland "Mamanuthaquinone: an antimicrobial and cytotoxic metabolite of Fasciospongia sp." Tetrahedron Letters199132, 6687–90.

    42. B. S. Davidson and C. M. Ireland "Lissoclinolide, the first non-nitrogenous metabolite from a Lissoclinum tunicate." Journal of Natural Products199053, 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 Letters199031, 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 Society1990112, 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 Letters198930, 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 Chemistry19893, 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 Letters198930, 3053–6.

    4. T. F. Molinski and C. M. Ireland "Varamines A and B, new cytotoxic thioalkaloids from Lissoclinum vareau." Journal of Organic Chemistry198954, 4256–9.

    5. T. M. Zabriskie and C. M. Ireland "The isolation and structure of modified bioactive nucleosides from Jaspis johnstoni." Journal of Natural Products198952, 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 Society1988110, 1308–9.

    7. T. F. Molinski and C. M. Ireland "Dysidazirine, a cytotoxic azacyclopropene from the marine sponge Dysidea fragilis." Journal of Organic Chemistry198853, 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 Chemistry198853, 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 Society1988110, 7919–20.

    10. T. C. McKee and C. M. Ireland "Cytotoxic and antimicrobial alkaloids from the Fijian sponge Xestospongia caycedoi." Journal of Natural Products198750, 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 Letters198728, 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 Society1986108, 6680–2.

    13. D. F. Sesin, S. J. Gaskell and C. M. Ireland "The chemistry of Lissoclinum patella." Bulletin des Societes Chimiques Belges198695, 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 Society1986108, 3123–4.

    15. J. E. Biskupiak and C. M. Ireland "Cytotoxic metabolites from the mollusc Peronia peronii." Tetrahedron Letters198526, 4307–10.

    16. D. M. Roll and C. M. Ireland "Citorellamine, a new bromoindole derivative from Polycitorella mariae." Tetrahedron Letters198526, 4303–6.

    17. J. E. Biskupiak and C. M. Ireland "Revised absolute configuration of dysidenin and isodysidenin." Tetrahedron Letters198425, 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 Chemistry198449, 559–61.

    19. D. F. Sesin and C. M. Ireland "Iodinated phenethylamine products from a didemnid tunicate." Tetrahedron Letters198425, 403–4.

    20. J. E. Biskupiak and C. M. Ireland "Absolute configuration of thiazole amino acids in peptides." Journal of Organic Chemistry198348, 2302–4.

    21. J. E. Biskupiak and C. M. Ireland "Pectinatone, a new antibiotic from the mollusk Siphonaria pectinata." Tetrahedron Letters198324, 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 Chemistry198348, 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 Chemistry198247, 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 Chemistry198247, 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 Products198144, 360–1.

    26. C. Ireland and D. J. Faulkner "The metabolites of the marine mollusks Tridachiella diomedea and Tridachia crispata." Tetrahedron, Supplement1981, 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 Society1980102, 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 Society1979101, 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)1979205, 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 Society1978100, 1002–3.

    4. C. Ireland and D. J. Faulkner "The defensive secretion of the opisthobranch mollusc Onchidella binneyi." Bioorganic Chemistry19787, 125–31.

    5. D. J. Faulkner and C. Ireland "The chemistry of some opisthobranch molluscs." NATO Conference Series IV: Marine Sciences19771, 23–34.

    6. C. Ireland and D. J. Faulkner "Diterpenes from Dolabella californica." Journal of Organic Chemistry197742, 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 Chemistry197641, 2461–5.

    8. C. Ireland, D. J. Faulkner, J. Finer and J. Clardy "A novel diterpene from Dollabella californica." Journal of the American Chemical Society197698, 4664–5.

    9. D. J. Faulkner, M. O. Stallard and C. Ireland "Prepacifenol epoxide, a halogenated sesquiterpene diepoxide." Tetrahedron Letters1974, 3571–4.

    10. M. Ramenofsky, D. J. Faulkner and C. Ireland "Effect of juvenile hormone on cirriped metamorphosis." Biochemical and Biophysical Research Communications197460, 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)1973179, 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, 200421, 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.