|
Unusual fatty acids from marine biota.
Our research group is particularly interested in isolating new antimicrobial
and/or cytotoxic lipids from marine invertebrates and microörganisms with potential applications in pharmacology and/or medicine. Marine biota from the Caribbean are under scrutiny. The group collaborates actively with the Department of Marine Sciences of the University of Puerto Rico, Mayagüez
Campus. The following specific projects are in progress:
Isolation and identification of new phospholipid fatty acids from marine invertebrates. (Anemone, algae, gorgonians and sponges) resulting from unusual biosynthetic schemes previously unrecognized in nature. GC-MS and modern techniques in lipidology are used to elucidate unusual marine lipids.
Isolation of new bacterial lipids from marine microorganisms. The role of symbiotic marine bacteria in the production of unusual fatty acids is also studied in Dr. Carballeira's laboratory. Of special interest is the identification of unusual symbiotic marine bacteria in nature and in using fatty acids as biomarkers for toxicity, such as the study of fatty acid composition of bacteria associated with toxic benthic dinoflagellates such as Ostreopsis lenticularis partially responsible for the production of potent toxins such as ciguatoxin.
Synthesis of bioactive and/or unusual marine fatty acids and phospholipids with the highest potential as antimicrobial agents. Some marine fatty acids, such as (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid, are antibacterial against Gram-positive bacteria, such as Staphylococcus and Streptococcus. An ongoing synthetic program for novel marine fatty acids aims at determining their antimicrobial activity.
Study of fatty acids as chemotaxonomic guides in the systematics of marine invertebrates. Some
marine invertebrates share similar fatty acid profiles; hence the utility of using these as chemotaxonomic
guides. Under study is the fatty acid composition of Caribbean gorgonians, such as Eunicea and Pseudopterogorgia,
since these are unique in biosynthesizing high amounts of polyunsaturated fatty acids 24:5(n-6) and 24:6(n-3).
Chemistry of methylene-interrupted fatty acids. The
chemistry of methylene interrupted fatty acids is of importance for the food industry. The aim is to understand rearrangement products from electrophilic additions to methylene-interrupted fatty acids such as linoleic acid.
Selected Publications
N. M. Carballeira “New
Advances in Fatty Acids as Antimalarial, Antimycobacterial,
and Antifungal Agents”, Prog. Lipid
Res., in press (2008).
N. M. Carballeira, D. Oyola, J. Vicente, and A. D. Rodríguez “Identification
of Novel α-Methoxylated Phospholipid Fatty Acids in the Caribbean Sponge Erylus
goffrilleri”, Lipids, 42,
1047-1053 (2007).
D. Tasdemir, B. Topaloglu,
R. Perozzo, R. Brun, R. O’Neill, N. M. Carballeira,
X. Zhang, P. J. Tonge, A. Linden, and P. Rüedi “Marine
Natural Products from the Turkish Sponge Agelas
oroides that Inhibit the Enoyl Reductases
from Plasmodium
falciparum, Mycobacterium tuberculosis and Escherichia
coli”, Bioorg. Med. Chem., 15,
6834-6845 (2007).
N. M. Carballeira,
R. O’Neill,
and K. Parang “Synthesis
and Antifungal Properties of a -Methoxy and a -Hydroxyl
Substituted 4-Thiatetradecanoic Acids”, Chem.
Phys. Lipids, 150, 82-88 (2007).
D.
Tasdemir, M. Cartagena, and N. M. Carballeira “Comparative
Analyses on Fatty Acid Composition of Bioactive
Organic Extracts from Different Anatomical Organs
of Five Turkish Rhododendron Species”, Planta
Medica, 73, 948 (2007).
N. M.
Carballeira, N. Montano, J. Vicente, and A. D.
Rodríguez “Novel Cyclopropane
Fatty Acids from the Phospholipids of the Caribbean
Sponge Pseudospongosorites suberitoides”, Lipids, 42,
519-524 (2007).
N. M. Carballeira,
D. Sanabria, and D. J. Oyola “An
Improved Synthesis for the (Z)-14-Methyl-9-pentadecenoic
Acid and its Topoisomerase I Inhibitory Activity”, Arkivoc-Archive
for Organic Chemistry, (viii),
49-57 (2007).
N.
M. Carballeira, N. Montano, and L. F. Padilla “First
Total Synthesis of (Z)-15-Methyl-10-hexadecenoic
Acid and the (Z)-13-Methyl-8-tetradecenoic
Acid”, Chem. Phys. Lipids, 145,
37-44 (2007).
back
|
