Summary: Salts and esters of the 12-carbon saturated monocarboxylic acid--lauric acid.

Top Publications

  1. Dietrich C, Bagatolli L, Volovyk Z, Thompson N, Levi M, Jacobson K, et al. Lipid rafts reconstituted in model membranes. Biophys J. 2001;80:1417-28 pubmed
    ..Overall, the notion that in biomembranes selected lipids could laterally aggregate to form more ordered, detergent-resistant lipid rafts into which glycosphingolipids partition is strongly supported by this study. ..
  2. Yu W, So P, French T, Gratton E. Fluorescence generalized polarization of cell membranes: a two-photon scanning microscopy approach. Biophys J. 1996;70:626-36 pubmed
    ..Our results also show local GP variations within the plasma and nuclear membranes. ..
  3. Lin Y, Schlievert P, Anderson M, Fair C, Schaefers M, Muthyala R, et al. Glycerol monolaurate and dodecylglycerol effects on Staphylococcus aureus and toxic shock syndrome toxin-1 in vitro and in vivo. PLoS ONE. 2009;4:e7499 pubmed publisher
    ..aureus growth and exotoxin production, which may reduce toxic shock syndrome. GML is proposed as a more effective anti-staphylococcal topical anti-infective candidate than DDG, despite its potential degradation by S. aureus lipase. ..
  4. Strandberg K, Peterson M, Schaefers M, Case L, Pack M, Chase D, et al. Reduction in Staphylococcus aureus growth and exotoxin production and in vaginal interleukin 8 levels due to glycerol monolaurate in tampons. Clin Infect Dis. 2009;49:1711-7 pubmed publisher
    ..These results suggest that GML added to tampons provides additional safety relative to menstrual toxic shock syndrome as well as benefits for vaginal health generally, thus supporting the addition of GML to tampons. ..
  5. Strandberg K, Peterson M, Lin Y, Pack M, Chase D, Schlievert P. Glycerol monolaurate inhibits Candida and Gardnerella vaginalis in vitro and in vivo but not Lactobacillus. Antimicrob Agents Chemother. 2010;54:597-601 pubmed publisher
    ..No adverse events were reported by participating women. GML is antimicrobial for Candida and G. vaginalis in vitro. Vaginal GML gels in women do not affect Lactobacillus negatively but significantly reduce Candida and G. vaginalis. ..
  6. Vetter S, Schlievert P. Glycerol monolaurate inhibits virulence factor production in Bacillus anthracis. Antimicrob Agents Chemother. 2005;49:1302-5 pubmed
    ..These data will be useful in developing therapeutic tools to treat anthrax disease, whether in animals or humans. These results also suggest that mechanisms of virulence regulation exist independent of atxA. ..
  7. Bagatolli L, Gratton E. Two photon fluorescence microscopy of coexisting lipid domains in giant unilamellar vesicles of binary phospholipid mixtures. Biophys J. 2000;78:290-305 pubmed
    ..In all cases the domains span the inner and outer leaflets of the membrane, suggesting a strong coupling between the inner and outer monolayers of the lipid membrane. This observation is also novel for unsupported lipid bilayers...
  8. Bagatolli L, Gratton E. A correlation between lipid domain shape and binary phospholipid mixture composition in free standing bilayers: A two-photon fluorescence microscopy study. Biophys J. 2000;79:434-47 pubmed
    ..This last finding extends previous observations of GUVs composed of DPPE/DPPC and DLPC/DPPC mixtures (, Biophys. J. 78:290-305)...
  9. Kubiak J, Brewer J, Hansen S, Bagatolli L. Lipid lateral organization on giant unilamellar vesicles containing lipopolysaccharides. Biophys J. 2011;100:978-86 pubmed publisher
    ..Our results indicate that LPSs can cluster into gel-like domains in these bacterial model membranes, and that the size of these domains depends on the chemical structure and concentration of the LPSs. ..

More Information


  1. Bagatolli L. To see or not to see: lateral organization of biological membranes and fluorescence microscopy. Biochim Biophys Acta. 2006;1758:1541-56 pubmed
    ..Additionally, the advantages of utilizing visual information, to correlate the lateral structure of compositionally simple membranes with complex situations, i.e., biological membranes, will be addressed...
  2. Peterson M, Schlievert P. Glycerol monolaurate inhibits the effects of Gram-positive select agents on eukaryotic cells. Biochemistry. 2006;45:2387-97 pubmed
    ..GML may be useful in the management of Gram-positive exotoxin illnesses; its action appears to be membrane stabilization with inhibition of signal transduction. ..
  3. Kaiser H, Lingwood D, Levental I, Sampaio J, Kalvodova L, Rajendran L, et al. Order of lipid phases in model and plasma membranes. Proc Natl Acad Sci U S A. 2009;106:16645-50 pubmed publisher
    ..Thus, lipid-mediated coalescence of the GM1 raft domain seems to be distinct from the formation of a Lo phase, suggesting additional interactions between proteins and lipids to be effective. ..
  4. Sanchez S, Bagatolli L, Gratton E, Hazlett T. A two-photon view of an enzyme at work: Crotalus atrox venom PLA2 interaction with single-lipid and mixed-lipid giant unilamellar vesicles. Biophys J. 2002;82:2232-43 pubmed
    ..These studies emphasize the importance of lateral packing of the lipids in C. atrox sPLA2 enzymatic hydrolysis of a membrane surface...
  5. Moench T, Mumper R, Hoen T, Sun M, Cone R. Microbicide excipients can greatly increase susceptibility to genital herpes transmission in the mouse. BMC Infect Dis. 2010;10:331 pubmed publisher
    ..However, excipients have not previously been tested in susceptibility models...
  6. Li Q, Estes J, Schlievert P, Duan L, Brosnahan A, Southern P, et al. Glycerol monolaurate prevents mucosal SIV transmission. Nature. 2009;458:1034-8 pubmed publisher
  7. Dodes Traian M, González Flecha F, Levi V. Imaging lipid lateral organization in membranes with C-laurdan in a confocal microscope. J Lipid Res. 2012;53:609-16 pubmed publisher
    ..These findings show that C-laurdan can be successfully employed for studies of membrane lateral organization using a conventional confocal microscope and can open the possibility of studying a wide variety of membrane-related processes. ..
  8. Sezgin E, Kaiser H, Baumgart T, Schwille P, Simons K, Levental I. Elucidating membrane structure and protein behavior using giant plasma membrane vesicles. Nat Protoc. 2012;7:1042-51 pubmed publisher
    ..GPMV preparation and isolation, including fluorescent labeling and observation, can be accomplished within 4 h...
  9. Bagatolli L, Parasassi T, Fidelio G, Gratton E. A model for the interaction of 6-lauroyl-2-(N,N-dimethylamino)naphthalene with lipid environments: implications for spectral properties. Photochem Photobiol. 1999;70:557-64 pubmed
    ..In the context of variable excitation wavelengths, information concerning solvent dipolar relaxation through excitation generalized polarization function is also discussed. ..
  10. Schlievert P, Strandberg K, Brosnahan A, Peterson M, Pambuccian S, Nephew K, et al. Glycerol monolaurate does not alter rhesus macaque (Macaca mulatta) vaginal lactobacilli and is safe for chronic use. Antimicrob Agents Chemother. 2008;52:4448-54 pubmed publisher
    ..The studies suggest that GML is safe for chronic use in monkeys when applied vaginally; it does not alter either mucosal microflora or integrity. ..
  11. Zhang H, Cui Y, Zhu S, Feng F, Zheng X. Characterization and antimicrobial activity of a pharmaceutical microemulsion. Int J Pharm. 2010;395:154-60 pubmed publisher
  12. Preuss H, Echard B, Enig M, Brook I, Elliott T. Minimum inhibitory concentrations of herbal essential oils and monolaurin for gram-positive and gram-negative bacteria. Mol Cell Biochem. 2005;272:29-34 pubmed
  13. Brewer J, Bernardino de la Serna J, Wagner K, Bagatolli L. Multiphoton excitation fluorescence microscopy in planar membrane systems. Biochim Biophys Acta. 2010;1798:1301-8 pubmed publisher
    ..This correspondence occurs when the lateral pressure of the monolayer is 26+/-2 mN/m and 28+/-3 mN/m for DOPC and DPPC, respectively. ..
  14. Schlievert P, Peterson M. Glycerol monolaurate antibacterial activity in broth and biofilm cultures. PLoS ONE. 2012;7:e40350 pubmed publisher
    ..GML may be useful as a broad-spectrum human or animal topical microbicide and may be useful as an environmental surface microbicide for management of bacterial infections and contamination. ..
  15. Kim H, Choo H, Jung S, Ko Y, Park W, Jeon S, et al. A two-photon fluorescent probe for lipid raft imaging: C-laurdan. Chembiochem. 2007;8:553-9 pubmed
    ..Lipid rafts can be visualized by two-photon microscopy by using C-laurdan as a probe. Our results show that the lipid rafts cover 38 % of the cell surface. ..
  16. Pechous R, Ledala N, Wilkinson B, Jayaswal R. Regulation of the expression of cell wall stress stimulon member gene msrA1 in methicillin-susceptible or -resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2004;48:3057-63 pubmed
  17. Stock R, Brewer J, Wagner K, Ramos Cerrillo B, Duelund L, Jernshøj K, et al. Sphingomyelinase D activity in model membranes: structural effects of in situ generation of ceramide-1-phosphate. PLoS ONE. 2012;7:e36003 pubmed publisher
  18. Antollini S, Barrantes F. Laurdan studies of membrane lipid-nicotinic acetylcholine receptor protein interactions. Methods Mol Biol. 2007;400:531-42 pubmed
    ..The application of this technique to the paradigm integral membrane protein, the nicotinic acetylcholine receptor, is described in this chapter. ..
  19. Vest R, Wallis R, Jensen L, Haws A, Callister J, Brimhall B, et al. Use of steady-state laurdan fluorescence to detect changes in liquid ordered phases in human erythrocyte membranes. J Membr Biol. 2006;211:15-25 pubmed
  20. Roche Y, Klymchenko A, Gerbeau Pissot P, Gervais P, Mely Y, Simon Plas F, et al. Behavior of plant plasma membranes under hydrostatic pressure as monitored by fluorescent environment-sensitive probes. Biochim Biophys Acta. 2010;1798:1601-7 pubmed publisher
    ..We thus suggested that BY-2 PM undergoes a complex phase behavior in response to the hydrostatic pressure and we also emphasized the role of phytosterols to regulate the effects of high hydrostatic pressure on plant PM...
  21. Fu X, Feng F, Huang B. Physicochemical characterization and evaluation of a microemulsion system for antimicrobial activity of glycerol monolaurate. Int J Pharm. 2006;321:171-5 pubmed
    ..The conclusion of this study was that GML loaded in microemulsion had much higher anti-microbial activity than GML alone. ..
  22. Jaikishan S, Slotte J. Stabilization of sphingomyelin interactions by interfacial hydroxyls - a study of phytosphingomyelin properties. Biochim Biophys Acta. 2013;1828:391-7 pubmed publisher
    ..The 2-hydroxylated acyl chains in phytoPSM did not markedly alter sterol affinity. We conclude that phytoPSM is a more ordered sphingolipid than PSM, and is fully capable of interacting with cholesterol. ..
  23. Samartsev V, Chezganova S, Polishchuk L, Paydyganov A, Vidyakina O, Zeldi I. Temperature dependence of rat liver mitochondrial respiration with uncoupling of oxidative phosphorylation by fatty acids. Influence of inorganic phosphate. Biochemistry (Mosc). 2003;68:618-26 pubmed
    ..Possible mechanisms of involvement of the phosphate carrier in the uncoupling effect of fatty acids are discussed. ..
  24. Szilagyi A, Selstam E, Akerlund H. Laurdan fluorescence spectroscopy in the thylakoid bilayer: the effect of violaxanthin to zeaxanthin conversion on the galactolipid dominated lipid environment. Biochim Biophys Acta. 2008;1778:348-55 pubmed
    ..Similar results were obtained in the liposomal systems in the presence of these xanthophyll cycle pigments. We conclude from these results that the conversion of violaxanthin to zeaxanthin makes the thylakoid membrane more ordered. ..
  25. Fuciños P, Dominguez A, Sanroman M, Longo M, Rúa M, Pastrana L. Production of thermostable lipolytic activity by thermus species. Biotechnol Prog. 2005;21:1198-205 pubmed
    ..The results suggest the occurrence of a specific mechanism of lipase/esterase secretion that might be due to the different composition and permeability of the cell membranes and those surrounding the rotund bodies. ..
  26. Chavant P, Gaillard Martinie B, Hebraud M. Antimicrobial effects of sanitizers against planktonic and sessile Listeria monocytogenes cells according to the growth phase. FEMS Microbiol Lett. 2004;236:241-8 pubmed
    ..Other sanitizers did not succeed in inhibiting totally the pathogen but acted in a similar way on both sessile and planktonic cells. Renewing the medium or not do not seem to be the major cause of a resistance emergence. ..
  27. Puff N, Watanabe C, Seigneuret M, Angelova M, Staneva G. Lo/Ld phase coexistence modulation induced by GM1. Biochim Biophys Acta. 2014;1838:2105-14 pubmed publisher
    ..GM1 could act on the line tension, "arresting" domain growth and thereby stabilizing Lo nanodomains. ..
  28. Bagatolli L, Sanchez S, Hazlett T, Gratton E. Giant vesicles, Laurdan, and two-photon fluorescence microscopy: evidence of lipid lateral separation in bilayers. Methods Enzymol. 2003;360:481-500 pubmed
  29. Vaish V, Sanyal S. Non steroidal anti-inflammatory drugs modulate the physicochemical properties of plasma membrane in experimental colorectal cancer: a fluorescence spectroscopic study. Mol Cell Biochem. 2011;358:161-71 pubmed publisher
    ..It may be stated that sulindac and celecoxib, the two NSAIDs may exert their anti-neoplastic role in colorectal cancer via modifying the physicochemical properties of the membranes. ..
  30. Jie M, Bakare O, Cheung Y, Chau S. Gas-liquid chromatographic properties of positional isomers of methyl thia, selena, and tellura laurate analogs. Lipids. 1997;32:679-81 pubmed
  31. Wawrik B, Harriman B. Rapid, colorimetric quantification of lipid from algal cultures. J Microbiol Methods. 2010;80:262-6 pubmed publisher
    ..Considering reagents and time, the total cost per assay was estimated at less than $5, representing a significant cost savings over traditional lipid quantification procedures. ..
  32. Toro C, Sanchez S, Zanocco A, Lemp E, Gratton E, Gunther G. Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size. Chem Phys Lipids. 2009;157:104-12 pubmed publisher
    ..ii) Insertion of cholesterol molecules into the lipid bilayer protects it from solubilizaton and (iii) the microscopic mechanism of solubilization by MMS implies the decrease in size of the individual liposomes. ..
  33. Samuni A, Lipman A, Barenholz Y. Damage to liposomal lipids: protection by antioxidants and cholesterol-mediated dehydration. Chem Phys Lipids. 2000;105:121-34 pubmed
    ..The relevance of cholesterol's presence, as a 'drying agent', in membranes containing PUFA to resistance of biological membranes to oxidative damage is discussed...
  34. Ozolina N, Nesterkina I, Kolesnikova E, Salyaev R, Nurminsky V, Rakevich A, et al. Tonoplast of Beta vulgaris L. contains detergent-resistant membrane microdomains. Planta. 2013;237:859-71 pubmed publisher
    ..Thus, the presence of detergent-resistant lipid-protein microdomains in the tonoplast has been demonstrated...
  35. Du L, Li G, Jin Y, Wang L, Xu Q, Dong J. Riboflavin laurate nanosuspensions as an intramuscular injection for long-term riboflavin supplementation. Int J Pharm. 2013;450:338-44 pubmed publisher
    ..The nanosuspensions were also used to resist the riboflavin deficiency induced by methotrexate chemotherapy. RFL nanosuspensions are a promising nanomedicine for long-term riboflavin supplementation. ..
  36. Buffone M, Doncel G, Calamera J, Verstraeten S. Capacitation-associated changes in membrane fluidity in asthenozoospermic human spermatozoa. Int J Androl. 2009;32:360-75 pubmed publisher
    ..This defect in sperm plasma membrane rheology may be responsible for their poor functional quality and low fertilizing ability. ..
  37. Abu Huwaij R, Assaf S, Salem M, Sallam A. Potential mucoadhesive dosage form of lidocaine hydrochloride: II. In vitro and in vivo evaluation. Drug Dev Ind Pharm. 2007;33:437-48 pubmed
    ..It was postulated that the hypothetical release mechanism of the drug and oleic acid from TLP was controlled by their diffusion through the swollen polymer network and micelled gel. ..
  38. Lester K, Simmonds R. Zoocin A and lauricidin in combination reduce Streptococcus mutans growth in a multispecies biofilm. Caries Res. 2012;46:185-93 pubmed publisher
    ..The pH of treated biofilms remained above neutral as opposed to a value of 4.3 in untreated controls. We conclude that use of antimicrobial compounds that specifically target cariogenic bacteria should be further explored. ..
  39. Koskinen E, Andersson M, Katila T. Effect of 19-norandrostenololylaurate on testicular growth in colts. Acta Vet Scand. 1997;38:51-7 pubmed
    ..Growth similar to that in control animals started after a delay of 4-5 months. TW in treated animals nearly reached TW in controls within 12 months of cessation of treatment. ..
  40. Barucha Kraszewska J, Kraszewski S, Ramseyer C. Will C-Laurdan dethrone Laurdan in fluorescent solvent relaxation techniques for lipid membrane studies?. Langmuir. 2013;29:1174-82 pubmed publisher
    ..This study suggests that, besides the lipid raft imaging, the C-Laurdan marker can considerably extend the capabilities of fluorescent solvent relaxation method. ..
  41. Liangqi Z, Jingfan X, Tao F, Haibin W. Synthesis of poly (3-hydroxybutyrate-co-3-hydroxyoctanoate) by a Sinorhizobium fredii strain. Lett Appl Microbiol. 2006;42:344-9 pubmed
    ..The potential of a Sinorhizobium fredii strain to produce a copolymer from glucose and sodium dodecanoate substrates was investigated...
  42. Nasuti C, Gabbianelli R, Cantalamessa F, Falcioni G. Erythrocyte plasma membrane perturbations in rats fed a cholesterol-rich diet: effect of drinking sulphurous mineral water. Ann Nutr Metab. 2005;49:9-15 pubmed
    ..Hydropinic treatment with SMW is of interest from the biomedical point of view, because it could represent an alternative approach in interventions aimed at ameliorating biological injury deriving from hypercholesterolaemia. ..
  43. Zolese G, Bacchetti T, Ambrosini A, Wozniak M, Bertoli E, Ferretti G. Increased plasma concentrations of palmitoylethanolamide, an endogenous fatty acid amide, affect oxidative damage of human low-density lipoproteins: an in vitro study. Atherosclerosis. 2005;182:47-55 pubmed
    ..1 microM), while the pro-oxidative effect is obtained at a higher PEA concentration (1 microM). Fluorescence and circular dichroism data indicate that the effect of PEA occurs mainly by affecting the conformational features of ApoB-100. ..
  44. Negre A, Dagan A, Gatt S. Pyrene-methyl lauryl ester, a new fluorescent substrate for lipases: use for diagnosis of acid lipase deficiency in Wolman's and cholesteryl ester storage diseases. Enzyme. 1989;42:110-7 pubmed
  45. Shin S, Cho C. Enhanced transdermal delivery of pranoprofen from the bioadhesive gels. Arch Pharm Res. 2006;29:928-33 pubmed
    ..74. The results of this study suggest that development of topical gel formulation of pranoprofen containing an enhancer is feasible. ..
  46. Zhang L, Yun Y, Liang Y, Cao D. Discovery of mass spectral characteristics and automatic identification of wax esters from gas chromatography mass spectrometry data. J Chromatogr A. 2010;1217:3695-701 pubmed publisher
  47. Owen D, Magenau A, Majumdar A, Gaus K. Imaging membrane lipid order in whole, living vertebrate organisms. Biophys J. 2010;99:L7-9 pubmed publisher
    ..The transition of membrane order imaging from cultured cell lines to living organisms is an important step forward in understanding the physiological relevance of membrane microdomains including lipid rafts...
  48. Wyss A, von Stockar U, Marison I. A novel reactive perstraction system based on liquid-core microcapsules applied to lipase-catalyzed biotransformations. Biotechnol Bioeng. 2006;93:28-39 pubmed
    ..5 to 9.0. The presence of an organic phase within the capsule core allowed direct product separation and lead to a decrease in product inhibition of the lipase-catalyzed reaction. ..
  49. Bainbridge B, Coats S, Pham T, Reife R, Darveau R. Expression of a Porphyromonas gingivalis lipid A palmitylacyltransferase in Escherichia coli yields a chimeric lipid A with altered ability to stimulate interleukin-8 secretion. Cell Microbiol. 2006;8:120-9 pubmed
    ..coli lipid A altered the activity of the LPS in monocytes but not endothelial cell assays and the difference in recognition does not appear to be related to differences in Toll-like receptor utilization. ..
  50. Lim P, Liu X, Kang L, Ho P, Chan Y, Chan S. Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol. Int J Pharm. 2006;311:157-64 pubmed
    ..The rheology of the gel matrix influenced drug release rate in a manner described by several experimentally-derived correlations. ..
  51. Wesołowska O, Gąsiorowska J, Petrus J, Czarnik Matusewicz B, Michalak K. Interaction of prenylated chalcones and flavanones from common hop with phosphatidylcholine model membranes. Biochim Biophys Acta. 2014;1838:173-84 pubmed publisher
    ..It was assumed that IXH-rich and IXH-poor microdomains appeared within membrane. Present work constitutes the first experimental report describing interactions of prenylated hop polyphenols with phospholipid model membranes. ..
  52. Jones P, Butt Y, Messmer B, Boriak R, Bennett M. Medium-chain fatty acids undergo elongation before beta-oxidation in fibroblasts. Biochem Biophys Res Commun. 2006;346:193-7 pubmed
    ..This previously undescribed metabolic step may have important implications for the metabolism of medium-chain triglycerides, components in the dietary treatment of a number of disorders. ..
  53. Ikegawa C, Ogita A, Doi T, Kumazawa F, Fujita K, Tanaka T. Involvement of Irreversible Vacuolar Membrane Fragmentation in the Lethality of Food Emulsifier Diglycerol Monolaurate against Budding Yeast. J Agric Food Chem. 2017;65:5650-5656 pubmed publisher
    ..Such an irreversible structural damage of the organelle membrane was considered a cause of DGL lethality. ..