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| fatty alcoholsSummarySummary: Usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4 carbons, derived from natural fats and oils, including lauryl, stearyl, oleyl, and linoleyl alcohols. They are used in pharmaceuticals, cosmetics, detergents, plastics, and lube oils and in textile manufacture. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Top Publications
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Three Arabidopsis fatty acyl-coenzyme A reductases, FAR1, FAR4, and FAR5, generate primary fatty alcohols associated with suberin depositionFrederic Domergue
Laboratoire de Biogenese Membranaire, Universite Victor Segalen Bordeaux 2, CNRS, UMR 5200, 33076 Bordeaux Cedex, France
Plant Physiol 153:1539-54. 2010..consisting of phenolics, glycerol, and a variety of fatty acid derivatives, including C18:0-C22:0 primary fatty alcohols. An eight-member gene family encoding alcohol-forming fatty acyl-coenzyme A reductases (FARs) has been ..
Skin permeation enhancement effect and skin irritation of saturated fatty alcoholsN Kanikkannan
College of Pharmacy and Pharm Science, Florida A and M University, Tallahassee 32307, USA
Int J Pharm 248:219-28. 2002..of this study was to evaluate the skin permeation enhancement effect and skin irritation of saturated fatty alcohols using melatonin as a model compound...
Nutritional significance and metabolism of very long chain fatty alcohols and acids from dietary waxesJames L Hargrove
Department of Foods and Nutrition, University of Georgia, Athens, Georgia 30602, USA
Exp Biol Med (Maywood) 229:215-26. 2004Very long chain fatty alcohols obtained from plant waxes and beeswax have been reported to lower plasma cholesterol in humans...
Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot pureeAndreas Czepa
, Lichtenbergstrasse 4, D-85748 Garching, Germany
J Agric Food Chem 51:3865-73. 2003..04 mmol/kg, thus demonstrating that this acetylenic diol significantly contributes to the bitter taste of the carrot products investigated...
A pheromone-binding protein mediates the bombykol-induced activation of a pheromone receptor in vitroEwald Grosse-Wilde
Institute of Physiology 230, University of Hohenheim, Garbenstrasse 30, 70599 Stuttgart, Germany
Chem Senses 31:547-55. 2006..This study provides evidence that both distinct pheromone receptors and PBPs play an important role in insect pheromone recognition...
Sexual attraction in the silkworm moth. Nature of binding of bombykol in pheromone binding protein--an ab initio studyVojtech Klusák
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, and Center for Complex Molecular Systems and Biomolecules, Flemingovo nam 2, Praha 6, 166 10, Czech Republic
Chem Biol 10:331-40. 2003..All of these interactions are well defined and cannot be considered as nonspecific hydrophobic interactions, one of the major conclusions of this work...
Pheromone discrimination by the pheromone-binding protein of Bombyx moriFrauke Gräter
Department of Theoretical and Computational Biophysics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Gottingen, Germany
Structure 14:1577-86. 2006..While BmorPBP might filter out other physiologically irrelevant compounds hitting the sensillar lymph, discrimination between the natural pheromone compounds must be achieved by molecular interactions with their cognate receptors...
Molecular switches for pheromone release from a moth pheromone-binding proteinWei Xu
Maeda Duffey Laboratory, Department of Entomology, University of California, 1 Shields Avenue, Davis, CA 95616, USA
Biochem Biophys Res Commun 372:559-64. 2008..The former leads to the formation of a new alpha-helix, which competes with pheromone for the binding pocket, whereas positive charge repulsion of the histidines opens the opposite side of the binding pocket...
Comparative lipid-lowering effects of policosanol and atorvastatin: a randomized, parallel, double-blind, placebo-controlled trialLuigi X Cubeddu
Division of Cardiology and Department of Internal Medicine, Mount Sinai Medical Center, Miami Beach, FL 33140, USA
Am Heart J 152:982.e1-5. 2006..We propose that policosanol should be added to the list of nutritional supplements lacking scientific validity to support their use...
Comparison of the efficacy, safety and tolerability of original policosanol versus other mixtures of higher aliphatic primary alcohols in patients with type II hypercholesterolemiaG Castano
Medical and Surgical Research Center, National Center for Scientific Research, Havana, Cuba
Int J Clin Pharmacol Res 22:55-66. 2002..Thus, policosanol reached the efficacy criterion for LDL-C reduction in both steps, while Octa-60 failed to reach this goal. In addition, policosanol was better tolerated than Octa-60...
Lack of cholesterol-lowering efficacy of Cuban sugar cane policosanols in hypercholesterolemic personsAmira N Kassis
School of Dietetics and Human Nutrition, McGill University, Ste-Anne-de-Bellevue, , Quebec, Canada
Am J Clin Nutr 84:1003-8. 2006..CONCLUSION: Present results show no beneficial effects of Cuban SCPs on lipid indicators in hypercholesterolemic persons and question the clinical usefulness of policosanol mixtures as cholesterol-lowering neutraceutical agents...
Policosanol inhibits cholesterol synthesis in hepatoma cells by activation of AMP-kinaseDev K Singh
College of Pharmacy, University of Kentucky, Lexington, KY 40536-0082, USA
J Pharmacol Exp Ther 318:1020-6. 2006..Because AMP-kinase is activated by phosphorylation and is well established to suppress HMG-CoA reductase activity, these results suggest that policosanol or a metabolite decreases HMG-CoA reductase activity by activating AMP-kinase...
Effects of policosanol and lovastatin on lipid profile and lipid peroxidation in patients with dyslipidemia associated with type 2 diabetes mellitusG Castano
Medical Surgical Research Center, Havana City, Cuba
Int J Clin Pharmacol Res 22:89-99. 2002..Nevertheless, since this was a pilot study, further clinical studies performed in larger sample sizes of diabetic patients are needed for definitive conclusions...
Inhibitory effects of [6]-gingerol on PMA-induced COX-2 expression and activation of NF-kappaB and p38 MAPK in mouse skinSue Ok Kim
College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
Biofactors 21:27-31. 2004..In addition, [6]-gingerol inhibited the phoshorylation of p38 mitogen-activated protein kinase which may account for its inactivation of NF-kappaB and suppression of COX-2 expression...
Effects of policosanol and ticlopidine in patients with intermittent claudication: a double-blinded pilot comparative studyGladys Castaño
Medical Surgical Research Center, Havana City, Cuba
Angiology 55:361-71. 2004..This study is, however, just a pilot comparison, so that further studies in larger sample sizes are needed for definitive conclusions of the comparative effects of both drugs on patients with IC...
Wheat germ policosanol failed to lower plasma cholesterol in subjects with normal to mildly elevated cholesterol concentrationsYuguang Lin
Unilever Health Institute, Unilever R and D, Vlaardingen, The Netherlands
Metabolism 53:1309-14. 2004..In conclusion, WGP at 20 mg/d had no beneficial effects on blood lipid profiles. It therefore seems unlikely that the long chain (C24-34) alcohols have any cholesterol-lowering activity...
Virucidal activities of medium- and long-chain fatty alcohols and lipids against respiratory syncytial virus and parainfluenza virus type 2: comparison at different pH levelsH Hilmarsson
Institute of Biology, University of Iceland, Reykjavik, Iceland
Arch Virol 152:2225-36. 2007Recent studies have shown that some lipids and fatty alcohols have microbicidal activities against a broad variety of pathogens...
Gingerol metabolite and a synthetic analogue Capsarol inhibit macrophage NF-kappaB-mediated iNOS gene expression and enzyme activityFugen Aktan
Faculty of Pharmacy, University of Sydney, New South Wales, Australia
Planta Med 72:727-34. 2006....
Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheresDjalil Coowar
Laboratoire de Chimie Organique des Substances Naturelles, UMR 7123 CNRS, , 5 rue Blaise Pascal, 67084 Strasbourg, France
J Med Chem 47:6270-82. 2004..neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared...
Ginger (Zingiber officinale Roscoe) and the gingerols inhibit the growth of Cag A+ strains of Helicobacter pyloriGail B Mahady
Department of Pharmacy Practice, UIC NIH Center for Botanical Dietary Supplements Research, PAHO WHO Collaborating Centre for Traditional Medicine, University of Illinois at Chicago, 833 S Wood St, MC 877, Chicago, IL 60612, USA
Anticancer Res 23:3699-702. 2003..Since Helicobacter pylori (HP) is the primary etiological agent associated with dyspepsia, peptic ulcer disease and the development of gastric and colon cancer, the anti-HP effects of ginger and its constituents were tested in vitro...
Analgesic and anti-inflammatory activities of [6]-gingerolHaw-Yaw Young
TzuHui Institute of Technology, 926 Ping'Tung, Taiwan, ROC
J Ethnopharmacol 96:207-10. 2005..6]-Gingerol (50 mg/kg-100 mg/kg) also produced an inhibition of paw edema induced by carrageenin. These results suggested that [6]-gingerol possessed analgesic and anti-inflammatory activities...
Dietary ginger constituents, galanals A and B, are potent apoptosis inducers in Human T lymphoma Jurkat cellsNoriyuki Miyoshi
Laboratory of Food and Biodynamics, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya 464-8601, Japan
Cancer Lett 199:113-9. 2003..In conclusion, the results from this study provide biological evidence that ginger-specific constituents other than curcuminoids are potential anticancer agents...
Antibacterial activity of long-chain fatty alcohols against Staphylococcus aureusNaoko Togashi
Department of Microbiology, Showa Pharmaceutical University, Machida, 194 8543 Tokyo, Japan
Molecules 12:139-48. 2007The antibacterial activity against Staphylococcus aureus of long-chain fatty alcohols was investigated, with a focus on normal alcohols...
Male gametophyte development in bread wheat (Triticum aestivum L.): molecular, cellular, and biochemical analyses of a sporophytic contribution to pollen wall ontogenyAiming Wang
Plant Biotechnology Institute, National Research Council of Canada, 110 Gymnasium Place, Saskatoon, Saskatchewan, Canada S7N 0W9
Plant J 30:613-23. 2002..the assembly of wall-impregnated sporopollenin, a phenylpropanoid-lipid polymer containing very long chain fatty alcohols (VLCFAlc), described in the literature...
The metabolism of fatty alcohols in lipid nanoparticles by alcohol dehydrogenaseX Dong
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky 40536-0082, USA
Drug Dev Ind Pharm 32:973-80. 2006b>Fatty alcohols are commonly used in lipid-based drug delivery systems including parenteral emulsions and solid lipid nanoparticles (NPs)...
Biphasic effect of falcarinol on caco-2 cell proliferation, DNA damage, and apoptosisJette F Young
Danish Institute of Agricultural Sciences, Department of Food Science, Research Centre Foulum, P O Box 50, DK 8830 Tjele, Denmark
J Agric Food Chem 55:618-23. 2007..Thus, the effects of falcarinol on CaCo-2 cells appear to be biphasic, inducing pro-proliferative and apoptotic characteristics at low and high concentrations of falcarinol, respectively...
In vitro and in vivo study of octacosanol metabolismRoberto Menendez
Center of Natural Products, National Center for Scientific Research, Havana City, Cuba
Arch Med Res 36:113-9. 2005..Scarce data about the metabolism of octacosanol and the other fatty alcohols composing policosanol have been published.
Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activitiesY Sekiwa
Graduate School of Humanities and Sciences, Laboratory of Food Chemistry, Department of Nutrition and Food Science, Ochanomizu University, 2 1 1 Ohtsuka, Bunkyo ku, Tokyo 112 8610, Japan
J Agric Food Chem 48:373-7. 2000..Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements...
Sexual attraction in the silkworm moth: structure of the pheromone-binding-protein-bombykol complexB H Sandler
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853 1301, USA
Chem Biol 7:143-51. 2000..The structure of the pheromone-binding protein, its binding and recognition of bombykol, and its full role in signal transduction are not known...
[6]-Gingerol, a pungent ingredient of ginger, inhibits angiogenesis in vitro and in vivoEok-Cheon Kim
Department of Biochemistry, College of Natural Sciences, Yonsei University, Seoul, Republic of Korea
Biochem Biophys Res Commun 335:300-8. 2005..Taken together, these results demonstrate that [6]-gingerol inhibits angiogenesis and may be useful in the treatment of tumors and other angiogenesis-dependent diseases...
Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substancesY Surh
Laboratory of Biochemistry and Molecular Toxicology, College of Pharmacy, Seoul National University, Shinlim Dong, Kwanak gu, Seoul, South Korea
Mutat Res 428:305-27. 1999..In addition, these compounds have ability to suppress proliferation of human cancer cells via induction of apoptosis...
Comparison of composition and absorption of sugarcane policosanolsChristopher P F Marinangeli
School of Dietetics and Human Nutrition, McGill University, Ste Anne de Bellevue, Quebec, H9X 3V9 Canada
Br J Nutr 97:381-8. 2007..05) than hamsters receiving APC1. If the cholesterol-lowering efficacy of PC mixtures is dependent on their purity and composition, then sugarcane-derived APC products should possess similar therapeutic properties as the OPC supplement...
Suppressive effects of mioga ginger and ginger constituents on reactive oxygen and nitrogen species generation, and the expression of inducible pro-inflammatory genes in macrophagesHa Won Kim
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8501, Japan
Antioxid Redox Signal 7:1621-9. 2005..Taken together, these results suggest that aframodial has potent antioxidative and anti-inflammatory potentials, and may be a promising candidate in prevention and/or therapy for chronic inflammationassociated carcinogenesis...
Cancer preventive properties of ginger: a brief reviewYogeshwer Shukla
Environmental Carcinogenesis Division, Industrial Toxicology Research Centre, P O Box 80, M G Marg, Lucknow 226 001, Uttar Pradesh, India
Food Chem Toxicol 45:683-90. 2007..A number of mechanisms that may be involved in the chemopreventive effects of ginger and its components have been reported from the laboratory studies in a wide range of experimental models...
Policosanol is ineffective in the treatment of hypercholesterolemia: a randomized controlled trialMichael F Dulin
Carolinas Medical Center Department of Family Medicine, Charlotte, NC, USA
Am J Clin Nutr 84:1543-8. 2006..Recent studies have challenged these findings, but there have been no trials conducted in North America that have examined the ability of sugar cane-derived policosanol to lower cholesterol...
Inhibitory effects of feeding with carrots or (-)-falcarinol on development of azoxymethane-induced preneoplastic lesions in the rat colonMorten Kobaek-Larsen
Biomedical Laboratory, University of Southern Denmark, Winsloewparken 23, DK 5000 Odense C, Denmark
J Agric Food Chem 53:1823-7. 2005..The present study provides a new perspective on the known epidemiological associations between high intake of carrots and reduced incidence of cancers...
Kinetics and molecular properties of pheromone binding and releaseWalter S Leal
Maeda Duffey Laboratory, Department of Entomology, University of California, Davis, CA 95616, USA
Proc Natl Acad Sci U S A 102:5386-91. 2005..Fluorescence studies shed light on the contributions of Trp-37 and Trp-127 emissions to the overall fluorescence...
Very long chain fatty acids (policosanols) and phytosterols affect plasma lipid levels and cholesterol biosynthesis in hamstersYanwen Wang
School of Dietetics and Human Nutrition, GcGill University, Ste-Anne-de-Bellevue, Quebec, Canada
Metabolism 54:508-14. 2005..05) in animals fed VLCFA25 and VLCFA50 than those fed control or VLCFA25/LT or VLCFA25/PS. Results suggest that PSs can decrease total and non-HDL-C cholesterol, whereas VLCFA may increase HDL-C in hamsters...
Policosanol modulates HMG-CoA reductase activity in cultured fibroblastsR Menendez
Laboratorio de Bioquimica, Centro de Productos Naturales, Centro Nacional de Investigación Científica, Havana, Cuba
Arch Med Res 32:8-12. 2001..Cholesterol biosynthesis is strictly controlled by 3-hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) reductase...
Pheromone reception in fruit flies expressing a moth's odorant receptorZainulabeuddin Syed
Department of Entomology, University of California, Davis, CA 95616, USA
Proc Natl Acad Sci U S A 103:16538-43. 2006..We also found an endogenous receptor in one of the sensillum types on Drosophila antenna that responds to bombykol and bombykal with sensitivity comparable to the pheromone-detecting sensilla on B. mori male antennae...
Functional expression of five Arabidopsis fatty acyl-CoA reductase genes in Escherichia coliThuy T P Doan
Department of Plant Breeding and Biotechnology, Swedish University of Agricultural Sciences, P O Box 101, 23053 Alnarp, Sweden
J Plant Physiol 166:787-96. 2009..The five functional FAR enzymes yielded distinctly different compositions of fatty alcohols when expressed in E...
Effects of a policosanol supplement on serum lipid concentrations in hypercholesterolaemic and heterozygous familial hypercholesterolaemic subjectsA Greyling
School of Physiology, Nutrition and Consumer Sciences, North-West University (Potchefstroom Campus, South Africa
Br J Nutr 95:968-75. 2006..An intake of 20 mg/d policosanol for 12 weeks had no significant effect on serum lipid levels in hypercholesterolaemic and heterozygous familial hypercholesterolaemic patients when compared with placebo intake...
Olefin cross-metathesis as a tool in natural product degradation. The stereochemistry of (+)-falcarindiolAnokha S Ratnayake
Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, Hawaii 96822, USA
Org Lett 4:4667-9. 2002..Degradation of (+)-falcarindiol from Tetraplasandra hawaiiensis yields a meso product as shown by chiral HPLC. Hence, (+)-falcarindiol from this source has a (3R,8S)-configuration...
[6]-Gingerol inhibits COX-2 expression by blocking the activation of p38 MAP kinase and NF-kappaB in phorbol ester-stimulated mouse skinSue Ok Kim
College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
Oncogene 24:2558-67. 2005..Taken together, our data suggest that [6]-gingerol inhibits TPA-induced COX-2 expression in mouse skin in vivo by blocking the p38 MAP kinase-NF-kappaB signaling pathway...
Insect sex-pheromone signals mediated by specific combinations of olfactory receptorsTakao Nakagawa
Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Chiba 277 8562, Japan
Science 307:1638-42. 2005..The same effects were also observed for general ORs. Both odorant and pheromone signaling pathways are mediated by means of a common mechanism in insects...
Dual bioactivity of resveratrol fatty alcohols: differentiation of neural stem cells and modulation of neuroinflammationFrédérique Hauss
Laboratoire de Chimie Organique des Substances Naturelles, UMR 7177 CNRS, Universite Louis Pasteur, 67084 Strasbourg Cedex, France
Bioorg Med Chem Lett 17:4218-22. 2007The synthesis of resveratrol fatty alcohols (RFAs), a new class of small molecules presenting strong potential for the treatment of neurological diseases, is described...
Effect of 6-gingerol on pro-inflammatory cytokine production and costimulatory molecule expression in murine peritoneal macrophagesSudipta Tripathi
Department of Surgery, SUNY Upstate Medical University, Syracuse, New York 13210, USA
J Surg Res 138:209-13. 2007....
Effects of policosanols and phytosterols on lipid levels and cholesterol biosynthesis in hamstersY W Wang
School of Dietetics and Human Nutrition, McGill University, Macdonald Campus, Ste-Anne-de-Bellevue, QC, Canada H9X 3V9
Lipids 38:165-70. 2003..Results suggest that, although phytosterols reduce T-C and HDL-C levels, policosanols have no significant favorable effect in changing lipid levels in hamsters...
Inhibition of epidermal growth factor-induced cell transformation and activator protein 1 activation by [6]-gingerolA M Bode
The Hormel Institute, University of Minnesota, Austin 55912, USA
Cancer Res 61:850-3. 2001..Our results provide the first evidence that both block EGF-induced cell transformation but act by different mechanisms...
Topical vehicles based on natural surfactant/fatty alcohols mixed emulsifier: The influence of two polyols on the colloidal structure and in vitro/in vivo skin performanceSnezana Savic
Faculty of Pharmacy, Institute of Pharmaceutical Technology and Cosmetology, Belgrade Vojvode Stepe 450, 11221 Belgrade, Serbia
J Pharm Sci 98:2073-90. 2009..Contrary to the effect of PG, the results obtained with GL suggest that it may have a permeation-retarding rather than a permeation-enhancing effect in topical vehicles of this type...
Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C)Lei Zhu
Department of Chemistry, Hunter College/CUNY, 695 Park Avenue, New York, New York 10021, USA
J Org Chem 69:3154-7. 2004..The synthesis confirms the structure of the natural product, and its convergent design makes it especially attractive for analogue synthesis...
Synthesis of pyragonicinDaniel Strand
KTH Chemistry, Organic Chemistry, SE-100 44 Stockholm, Sweden
Org Lett 7:2779-81. 2005..A reagent controlled zinc-mediated stereoselective coupling, joining the two highly functionalized intermediates 3 and 4, then provided the core structure...
Total synthesis of the proposed structure for pyragonicinShunya Takahashi
RIKEN The Institute of Physical and Chemical Research, Wako, Saitama 351 0198, Japan
Org Lett 7:2783-6. 2005..Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation...
Total synthesis of (+)-muconinTakehiko Yoshimitsu
Meiji Pharmaceutical University, 2 522 1 Noshio, Kiyose, Tokyo 204 8588, Japan
J Org Chem 69:1993-8. 2004..In this study, a new route was established for obtaining (+)-muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofuran...
Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategiesRadha S Narayan
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA
J Org Chem 71:1416-29. 2006..On the basis of detailed spectroscopic analysis of the synthesized molecule, we reason that the spectral discrepancies are due to stereochemical misassignment of the natural product...
Total synthesis of jimenezin via an intramolecular allylborationNina G Bandur
Fachbereich Chemie, Philipps Universitat Marburg, Hans Meerwein Strasse, 35032 Marburg, Germany
Org Lett 8:3829-31. 2006..The key steps used were a highly stereoselective intramolecular allylboration to establish the tetrahydropyran ring and an intramolecular Williamson reaction to close the tetrahydrofuran ring...
On the proof and disproof of natural product stereostructures: characterization and analysis of a twenty-eight member stereoisomer library of murisolins and their Mosher ester derivativesDennis P Curran
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
J Am Chem Soc 128:9943-56. 2006..The structure of murisolin was proved to be the 4R,15R,16R,19R,20R,34S isomer, whereas the assignment of 16,19-cis-murisolin as RRRSSS was changed to the RSSRRS diastereomer and murisolin A is suggested to be RSRRRS...
New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of SolaminGuillaume Prestat
CEA, CE-Saclay, , , , 91191 Gif sur Yvette, France
J Org Chem 69:5770-3. 2004..The flexibility of the strategy should be useful in preparing various natural and unnatural annonaceous acetogenins...
Function of the alkyl side chains of Deltalac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)Naoya Ichimaru
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan
Bioorg Med Chem Lett 16:3555-8. 2006..This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane...
Zooxanthellamide B, a novel large polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium spKen-ichi Onodera
Graduate School of Bioagricultural Sciences, Nagoya University, Japan
Biosci Biotechnol Biochem 68:955-8. 2004....
Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF ringsMasato Abe
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
Bioorg Med Chem Lett 14:779-82. 2004..Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect...
In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex IJosé R Tormo
CIBE Merck Research Laboratories, Merck, SHARP and DOHME de ESPANA S A, C Josefa Valcárcel, 38, Madrid 28027, Spain
Oncol Res 14:147-54. 2003....
Cytotoxic monotetrahydrofuran acetogenins from Disepalum plagioneurumVéronique Eparvier
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 1 Avenue de la Terrasse, 91198 Gif sur Yvette Cedex, France
J Nat Prod 69:1289-94. 2006..The new monotetrahydrofuran (mono-THF) acetogenins exhibited significant in vitro cytotoxicity against the KB cancer cell line, with IC(50) values in the nanomolar range...
ABC synthesis and antitumor activity of a series of Annonaceous acetogenin analogs with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unitJames A Marshall
Department of Chemistry, University of Virginia, Charlottesville, VA 22904, USA
Bioorg Med Chem Lett 17:2434-7. 2007..Side-chain analogs of Annonaceous acetogenins with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit have been prepared and tested for cytotoxicity against HCT-116 human colon cancer cells...
Polyporolide, a new acetogenin from the mycelial culture of a Polyporus fungusZhihui Chen
South China Botanical Garden, Chinese Academy of Sciences, Leyiju, Guangzhou 510650, China
Nat Prod Res 20:1145-9. 2006..Its structure was elucidated as 4-hydroxy-5-(1-hydroxyhexyl)-dihydrofuran-2-one by spectroscopic methods. Its toxicity to brine shrimps was assessed...
Synthesis and mitochondrial complex I inhibition of dihydroxy-cohibin A, non-THF annonaceous acetogenin analogueHiroyuki Konno
Department of Biological Science and Technology, Faculty of Engineering, University of Tokushima, 2 1Minamijosanjima cho, Tokushima 770 8506, Japan
Bioorg Med Chem Lett 14:629-32. 2004..Our results indicate that these hydroxy groups are an essential structural factor though it is not effective as bis-THF hydroxy groups combination...
[Determination of annonaceous acetogenins in annonaceae plants by HPLC]L Sun
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100094, China
Yao Xue Xue Bao 36:683-5. 2001..3% and 100.0%, respectively. CONCLUSION: This method was developed for the analysis of acetogenins by HPLC for the first time. The method is rapid, accurate and suitable for the analysis of the antitumor acetogenins in Annonaceae plants...
Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex IYasunao Hattori
Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minaniminowa Kami ina, Nagano 399 4598, Japan
Org Lett 10:717-20. 2008..The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin...
Biogenetic relationships between Annonaceous acetogenins: squamocin is not a precursor of chamuvarinin based on a semisynthetic studySéverine Derbré
Laboratoire de Pharmacognosie Associé au CNRS BioCIS, UMR 8076, Universite Paris Sud 11, Faculte de Pharmacie, 5 Rue Jean Baptiste Clement, 92296 Chatenay Malabry Cedex, France
J Nat Prod 70:300-3. 2007..Based on this, a plausible relative configuration was proposed for 2, demonstrating the absence of any biogenetic link between 1 and 2. The new analogues 3, 4, and 7 were also tested for their ability to induce apoptosis...
Novel cytotoxic monotetrahydrofuranic Annonaceous acetogenins from Annona montanaChih-Chuang Liaw
Graduate Institute of Natural Products, Kaohsiung Medical University, 100, Shih-Chuan 1st Road, Kaohsiung, Taiwan
Bioorg Med Chem 13:4767-76. 2005..The absolute stereochemical structures of new isolates were elucidated and characterized by spectral and chemical methods. Interestingly, these compounds show special cytotoxicity against human hepatoma cells, Hep G2...
An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogueJames A Marshall
Department of Chemistry, P O Box 400319, University of Virginia, Charlottesville, Virginia 22904, USA
Org Lett 8:3557-60. 2006..reaction: see text] A synthesis of the Annonaceous acetogenin asimicin and a side-chain analogue has been achieved by a highly convergent route in which Grubbs cross-metathesis plays a key role...
In vitro antitumor structure-activity relationships of threo/trans/threo/trans/erythro bis-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex IJosé R Tormo
CIBE Merck Research Laboratories, Merck, SHARP and DOHME de ESPANA S A, C Josefa Valcdrcel, 38, Madrid 28027, Spain
Oncol Res 15:129-38. 2005..For example, some of the guanacone derivatives prepared were two orders of magnitude more potent than the parent compound for specific cell lines...
Stereochemically general approach to adjacent bis(tetrahydrofuran) cores of annonaceous acetogeninsLaura M Wysocki
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA
Org Lett 8:5637-40. 2006..The stereochemistry of four of these isomers has been found in the biologically active annonaceous acetogenin natural products. [reaction: see text]...
A bidirectional approach to the synthesis of a complete library of adjacent-bis-THF annonaceous acetogeninsSanjib Das
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
J Org Chem 70:5922-31. 2005..Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved...
Divergence en route to nonclassical annonaceous acetogenins. Synthesis of pyranicin and pyragonicinDaniel Strand
KTH Chemical Science and Engineering, Organic Chemistry, SE-100 44 Stockholm, Sweden
J Org Chem 71:1879-91. 2006..The methodology is further expanded by a divergent synthesis of all stereoisomers of the 2,3,6-trisubstituted tetrahydropyran subunit...
Solution-phase parallel synthesis with oligoethylene glycol sorting tags. Preparation of all four stereoisomers of the hydroxybutenolide fragment of murisolin and related acetogeninsVenugopal Gudipati
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
J Org Chem 71:3599-607. 2006..The experimental features (reaction, analysis, separation, and characterization) of OEG mixture synthesis are detailed and are compared to and contrasted with those of fluorous mixture synthesis...
Induction of cell death of gastric cancer cells by a modified compound of the annonaceous acetogenin familyGuo-Rui Huang
Laboratory of Molecular Cell Biology, Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 320 Yue-Yang Road, Shanghai 200031, China
Chembiochem 4:1216-21. 2003..These results show for the first time that the polyether mimic AA005 acts on the same biological target as the natural annonaceous acetogenins...
Structure-antiemetic-activity of some diarylheptanoids and their analoguesY Yang
Department of Pharmacognosy and Phytochemistry, Meiji Pharmaceutical University, Tokyo, Japan
Phytomedicine 9:146-52. 2002..Among them, two types of essential functional structure of diarylheptanoids and their analogues showed the inhibitory effects against emesis...
Stability of [6]-gingerol and [6]-shogaol in simulated gastric and intestinal fluidsSushila Bhattarai
Faculty of Pharmacy, University of Sydney, NSW 2006, Australia
J Pharm Biomed Anal 45:648-53. 2007..The degradation profile of [6]-gingerol and [6]-shogaol under simulated physiological conditions reported in this study will provide insight into the stability of these compounds when administered orally...
Cytotoxic components from the dried rhizomes of Zingiber officinale RoscoeJu Sin Kim
College of Pharmacy, Woosuk University, Samrye, Korea
Arch Pharm Res 31:415-8. 2008..6-shogaol inhibited proliferation of the transgenic mouse ovarian cancer cell lines, C1 (genotype: p53(-/-), c-myc, K-ras) and C2 (genotype: p53(-/-), c-myc, Akt), with ED(50) values of 0.58 microM (C1) and 10.7 microM (C2)...
Nine new cytotoxic monotetrahydrofuranic Annonaceous acetogenins from Annona montanaChih-Chuang Liaw
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
Planta Med 70:948-59. 2004..These monotetrahydrofuranic Annonaceous acetogenins showed selectively potent cytotoxicity against two human cancer cell lines, 1A9 and Hep G2...
Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of annonaceous acetogeninsRomain A Duval
Laboratoire de Pharmacognosie BioCIS, UMR 8076 CNRS, Faculte de Pharmacie, University Paris Sud, rue J B Clement, 92296 Chatenay Malabry Cedex, France
Biochemistry 45:2721-8. 2006..This result supports the existence of a large cooperatively regulated inhibitor/ubiquinone-binding pocket located within the catalytic core of the enzyme, consisting of the association of the previously defined affinity sites A and B...
Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated worldMurray B Isman
Faculty of Land and Food Systems, University of British Columbia, Vancouver, Canada
Annu Rev Entomol 51:45-66. 2006....
Atemoyacin E, a bis-tetrahydrofuran annonaceous acetogenin from Annona atemoya seedsP Wu
South China Institute of Botany, Chinese Academy of Sciences, Guangzhou
J Asian Nat Prod Res 3:177-82. 2001..Atemoyacin E (I), a new adjacent bis-tetrahydrofuran annonaceous acetogenin was isolated and characterized from the seeds of Annona atemoya...
Cardiovascular effects of ginger aqueous extract and its phenolic constituents are mediated through multiple pathwaysMuhammad Nabeel Ghayur
Department of Biological and Biomedical Sciences, The Aga Khan University Medical College, Karachi 74800, Pakistan
Vascul Pharmacol 43:234-41. 2005....
Evaluation of the topical anti-inflammatory activity of ginger dry extracts from solutions and plastersPaola Minghetti
Istituto di Chimica Farmaceutica e Tossicologica Pietro Pratesi, Universita degli Studi di Milano, Milano, Italy
Planta Med 73:1525-30. 2007..3). This preliminary result suggests that the anti-inflammatory effect observed in mice could also be exerted in humans...
The anti-staphylococcal activity of Angelica dahurica (Bai Zhi)Doris Lechner
Centre for Pharmacognosy and Phytotherapy, The School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK
Phytochemistry 65:331-5. 2004..These MIC values compare favourably with some of the newest agents in development for the treatment of MRSA infection and indicate that further evaluation of the antibiotic activity of acetylenes is warranted...
Guanaconetins, new antitumoral acetogenins, mitochondrial complex I and tumor cell growth inhibitorsNadia Chahboune
, Facultad de Farmacia, Universidad de Valencia, Burjassot, Spain
Bioorg Med Chem 14:1089-94. 2006..Placement of acetyl groups along the alkyl chain modulated the potency of the bis-tetrahydrofuranic acetogenins and could be important for future utilization of these compounds as chemotherapeutic agents...
A structure-activity guided strategy for fluorescent labeling of annonaceous acetogenin mimetics and their application in cell biologyHai-xia Liu
State Key Laboratory of Bioorganic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
Chembiochem 8:172-7. 2007
Halogenated metabolites from Japanese Laurencia sppMinoru Suzuki
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan
Phytochemistry 66:2787-93. 2005..Their structures were deduced from analysis of spectroscopic data...
Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of actionAlmudena Bermejo
Laboratoire de Pharmacognosie, associe au CNRS BIOCIS, Faculte de Pharmacie, Universite Paris Sud, 92296, Chatenay Malabry, France
Nat Prod Rep 22:269-303. 2005..In fact, of the 417 isolated compounds reviewed, over 176 have been added during the period from 1998 to 2004...
Convergent synthesis of pyragonicinShunya Takahashi
RIKEN The Institute of Physical and Chemical Research, Wako Shi, Saitama, 351 0198, Japan
J Org Chem 71:6305-8. 2006..A novel MOM-migrating reaction found in a cyclization reaction is also discussed...
Structural identification of the beta-hydroxy fatty acid-based diester preen gland waxes of shorebirdsW Irene C Rijpstra
Departments of Marine Biogeochemistry and Toxicology and Marine Ecology and Evolution, Royal Netherlands Institute for Sea Research NIOZ, PO Box 59, 1790 AB Den Burg, The Netherlands
J Nat Prod 70:1804-7. 2007..using synthesized standards, to comprise predominantly C12-C16 beta-hydroxy fatty acids esterified with a C8-C18 fatty acid at the beta-hydroxy position and with predominantly C12-C20 fatty alcohols esterified at the carboxyl group.
Inhibitory effect of tumor cell proliferation and induction of G2/M cell cycle arrest by panaxytriolJi Yeon Kim
Department of Food Science and Technology and School of Agricultural Biotechnology, Seoul National University, Suwon, Korea
Planta Med 68:119-22. 2002..There were corresponding decreases in the proportion of cells at the G0/G1 phase. The S phase also decreased during the 36-h treatment...
[6]-gingerol induces Ca2+ mobilization in Madin-Darby canine kidney cellsChung Yi Chen
School of Medicine and Health Sciences, Department of Medical Technology, Fooyin University, Kaohsiung County, Taiwan, Republic of China
J Nat Prod 71:137-40. 2008....
Analysis of a ginger extract by high-performance liquid chromatography coupled to nuclear magnetic resonance spectroscopy using superheated deuterium oxide as the mobile phaseShikha Saha
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK
J Chromatogr A 991:143-50. 2003..On-line and off-line HPLC-NMR analysis yielded spectra for vanillin, dihydroferulic acid, zingerone and ferulic acid. The identification of dihydroferulic acid and zingerone were confirmed by mass spectroscopy...
Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterasesMaria del Carmen Ramirez-Ahumada
Arizona Center for Phytomedicine Research and Department of Pharmacology and Toxicology, University of Arizona, Tucson, AZ 85721-0036, USA
Phytochemistry 67:2017-29. 2006..These activities may shunt phenylpropanoid pathway intermediates away from the production of curcuminoids and gingerols, thereby potentially playing a regulatory role in the biosynthesis of these compounds...
Effects of D-003, a mixture of very long chain saturated fatty acids, and policosanol on in vivo lipid peroxidation in ratsYohani Perez
Center of Natural Products, National Center for Scientific Research, Havana City, Cuba
Arzneimittelforschung 58:126-30. 2008....
A comparison of the effects of D-003 and policosanol (5 and 10 mg/day) in patients with type II hypercholesterolemia: a randomized, double-blinded studyG Castano
Medical Surgical Research Center, Havana City, Cuba
Drugs Exp Clin Res 31:31-44. 2005..D-003 could be useful for treating type II hypercholesterolemia, but this subject deserves further clinical research...
Molecular simplification in bioactive molecules: formal synthesis of (+)-muconinFernando R Pinacho Crisóstomo
Instituto Universitario de Bio Organica Antonio Gonzalez, Universidad de La Laguna, Astrofísico Astrofísico Francisco Sanchez 2, 38206 La Laguna, Tenerife, Islas Canarias, Spain
J Org Chem 71:2339-45. 2006..The strategy opens the way to preparing novel bioactive acetogenin analogues by shorter synthetic routes...
[Systematic synthesis of antitumor annonaceous acetogenins]Naoto Kojima
Graduate School of Pharmaceutical Sciences, Osaka University, Suite, Osaka 565 0871, Japan
Yakugaku Zasshi 124:673-81. 2004..In addition, the total synthesis of murisolin, which shows cytotoxic activity against human tumor cell lines with potency from 10(5) to 10(6) times that of adriamycin, was also achieved...
Research Grants
- 9 CIS RETINOL DEHYDROGENASE--PROPERTIES AND PHYSIOLOGYWILLIAM BLANER; Fiscal Year: 2004..13-cis- and all-trans-retinol but not other retinoids or long chain fatty acids, short chain fatty acids or fatty alcohols. For the mouse, this protein is 54 percent identical at the amino acid level to cellular retinol-binding ..
- ICHTHYOSIS IN SJOGREN/LARSSON SYNDROMEWILLIAM RIZZO; Fiscal Year: 2000..This knowledge is critical for developing effective therapeutic approaches to this disease. ..
- Ichthyosis in Sjogren-Larsson SyndromeWilliam B Rizzo; Fiscal Year: 2010..and are hypothesized to arise from the deranged metabolism of fatty aldehydes and precursor lipids such as fatty alcohols, which cannot be metabolized by FALDH...
- Ichthyosis in Sjogren-Larsson SyndromeWILLIAM RIZZO; Fiscal Year: 2007..and are hypothesized to arise from the deranged metabolism of fatty aldehydes and precursor lipids such as fatty alcohols, which cannot be metabolized by FALDH...
- Ichthyosis in Sjogren-Larsson SyndromeWILLIAM RIZZO; Fiscal Year: 2007..and are hypothesized to arise from the deranged metabolism of fatty aldehydes and precursor lipids such as fatty alcohols, which cannot be metabolized by FALDH...
- Ichthyosis in Sjogren-Larsson SyndromeWILLIAM RIZZO; Fiscal Year: 2005..These studies will provide fundamental information about the role of FALDH in epidermal lipid metabolism and promise to reveal new mechanisms for fatty aldehyde toxicity in SLS. ..
- Synthesis of Tumor Inhibitory Marine Natural ProductsJames Marshall; Fiscal Year: 2004..The main chemical issues to be addressed include the control of stereochemistry by means of chiral organometal chemistry and the design of new and efficient routes to structurally novel natural products. ..
- SYNTHESIS OF ANNONACEOUS ACETOGENINS AND ANALOGUESJames Marshall; Fiscal Year: 2001..The synthetic approach will employ chiral allylic and allenic organometal reagents to introduce stereogenic centers with concurrent formation of carbon-carbon bonds. ..
- Docosanol and Acyclovir for Treating Genital HerpesLAURA POPE; Fiscal Year: 2003..If proven safe and effective, it would provide a new single agent treatment as well as allow concurrent use with acyclovir. PROPOSED COMMERCIAL APPLICATION: Topical treatment for recurrent genital herpes infections. ..
- Purchase of a 600 MHz NMR Spectrometer with CryoprobeDENNIS CURRAN; Fiscal Year: 2007..This research often requires sophisticated NMR experiments on small samples, and the requested 600 MHz spectrometer will greatly expedite ongoing and planned work. ..
- Fluorous Mixture Synthesis of Natural Product LibrariesDENNIS CURRAN; Fiscal Year: 2007..To prove the concept, first eight diastereomers and later all sixteen isomers of passifloricin A will be synthesized. ..
- Efficacy of Turmeric Extract in Prevention of Post-menopausal OsteoporosisJanet Funk; Fiscal Year: 2007....
- BACCALAUREATE BRIDGE TO THE BIOMEDICAL SCIENCES PROGRAMPHIL CREWS; Fiscal Year: 2007..The structure of our program continues to build on concepts introduced in the original proposal. ..
- A Transdisciplinary Approach to the Evaluation of Social Determinants of Health sMichael F Dulin; Fiscal Year: 2010....
- MATHEMATICAL MODELING IN NUTRITIONJames Hargrove; Fiscal Year: 2003..Lastly, a panel will discuss the use of modeling in undergraduate and graduate education, and will make recommendations for appropriate activities of a new Research Interest Section on Mathematical Modeling. ..
- Anti-Trypanosomal Agents from a Neotropical CloudforestWILLIAM SETZER; Fiscal Year: 2004..The long-term benefit of this research project is the development of new medicines to treat patients with Chagas disease. ..
- Acquisition of a Varian 600 MHz High-Resolution NMRPHIL CREWS; Fiscal Year: 2004..The instrument and its complement of probes will be essential for maintaining modern research with competitive throughput and the training of our students in a modern research environment. ..
- NOVEL CYTOTOXIC NATURAL PRODUCTS FROM MARINE SPONGESPhillip Crews; Fiscal Year: 1993..Corresponding attention will be given to isolating analogs and preparing semisynthetic derivatives of these active lead compounds...
- NOVEL CYTOTOXIC NATURAL PRODUCTS FROM MARINE SPONGESPhillip Crews; Fiscal Year: 2002..An adjunct to the HFCC in vitro mammalian cell assays will be "bench-top assays" carried out at UCSC. ..
- DESIGN AND SYNTHESIS OF NONPEPTIDE PROTEASE INHIBITORSArun Ghosh; Fiscal Year: 2009..This research integrates organic synthesis, protein-ligand x-ray crystallography, molecular modeling and in-depth virus and cell-biological studies to design the next generation of HIV-1 protease inhibitors. ..
- Discovery of novel cytotoxic natural products from marine sponges and fungiPHIL CREWS; Fiscal Year: 2010..of California Santa Cruz (UCSC) lead by Prof. Crews and the Experimental Therapeutics Program at the Henry Ford Cancer Center (HFCC) lead by Prof. Valeriote. ..
- Botanicals for Chlamydia pneumonia infections-Revision 1Gail Mahady; Fiscal Year: 2005..Data and active standardized extracts developed during this work will be used as the basis for future clinical trials. ..
- ASYMMETRIC THERMAL ADDITION AND CYCLOADDITION REACTIONSDENNIS CURRAN; Fiscal Year: 1993..However, exciting preliminary results indicate that these goals are realistic, and that original and powerful solutions to important problems in the synthesis of biomedically active compounds will be forthcoming...
- Biochemistry and Biophysics of the Preocular Tear FilmIgor A Butovich; Fiscal Year: 2010....
- SYNTHESIS VIA SEQUENTIAL FREE RADICAL REACTIONSDENNIS CURRAN; Fiscal Year: 1991..The chemistry outlined int his proposal will contribute both to the understanding of free radical reactions and to the ability to prepare important cyclopentanoid natural products...
- FLUOROUS REAGENTS IN TRADITIONAL/COMBINATORIAL SYNTHESISDENNIS CURRAN; Fiscal Year: 1999....
- RADICAL REACTIONS FOR NATURAL PRODUCTSDENNIS CURRAN; Fiscal Year: 2002....
- FLUOROUS METHODS FOR TRADITIONAL AND PARALLEL SYNTHESISDENNIS CURRAN; Fiscal Year: 2003..In short, the work will help to move the very young field of fluorous chemistry from infancy into childhood. ..
