lactones

Summary

Summary: Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES.

Top Publications

  1. Mejia E, Loveridge S, Stepan G, Tsai A, Jones G, Barnes T, et al. Study of marine natural products including resorcyclic acid lactones from Humicola fuscoatra that reactivate latent HIV-1 expression in an in vitro model of central memory CD4+ T cells. J Nat Prod. 2014;77:618-24 pubmed publisher
    ..We report the bioassay-guided isolation and structure determination of several resorcyclic acid lactones, including four known compounds, radicicol (1, aka...
  2. Jia Q, Wang J, Long J, Zhao Y, Chen S, Zhai J, et al. Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-?B activation and MCP-1 and TGF-?1 expression in rat mesangial cells. Molecules. 2013;18:13061-77 pubmed publisher
    ..We selected and synthesized several sesquiterpene lactones (SLs), and then used the MTT assay to detect rat mesangial cells (MCs) proliferation, ELISA to measure the ..
  3. Ding Y, Fan H, Long J, Zhang Q, Chen Y. The application of Heck reaction in the synthesis of guaianolide sesquiterpene lactones derivatives selectively inhibiting resistant acute leukemic cells. Bioorg Med Chem Lett. 2013;23:6087-92 pubmed publisher
    A series of guaianolide-type sesquiterpene lactones derivatives with arylation of ?-methylene-?-lactone moiety was synthesized using Heck reactions, and was evaluated for their activities against acute myelogenous leukemia (AML) cell line ..
  4. Lopes A, Pina E, Silva D, Pereira A, da Silva M, da Costa F, et al. A biosynthetic pathway of sesquiterpene lactones in Smallanthus sonchifolius and their localization in leaf tissues by MALDI imaging. Chem Commun (Camb). 2013;49:9989-91 pubmed publisher
    The biosynthetic route for epoxyangelate esters of the sesquiterpene lactones (STL) uvedalin and enhydrin from in vitro cultures of Smallanthus sonchifolius (Asteraceae) was investigated with (13)C-precursors for the first time in the ..
  5. Luo Z, Du H, Li L, An M, Zhang Z, Wan X, et al. Fuzhuanins A and B: the B-ring fission lactones of flavan-3-ols from Fuzhuan brick-tea. J Agric Food Chem. 2013;61:6982-90 pubmed publisher
    ..Our phytochemical research of the material led to the isolation of two new B-ring fission lactones of flavan-3-ols, fuzhuanins A (1) and B (2)...
  6. Albrecht A, Morana F, Fraile A, Jørgensen K. Organophosphorus reagents in organocatalysis: synthesis of optically active ?-methylene-?-lactones and ?-lactams. Chemistry. 2012;18:10348-54 pubmed publisher
    ..paper we describe new asymmetric, catalytic strategies for the synthesis of biologically important ?-methylene-?-lactones and ?-lactams...
  7. Lohberger B, Rinner B, Stuendl N, Kaltenegger H, Steinecker Frohnwieser B, Bernhart E, et al. Sesquiterpene lactones downregulate G2/M cell cycle regulator proteins and affect the invasive potential of human soft tissue sarcoma cells. PLoS ONE. 2013;8:e66300 pubmed publisher
    ..The present study investigates the effects of the sesquiterpene lactones costunolide and dehydrocostus lactone on cell cycle, MMP expression, and invasive potential of three human STS ..
  8. Tsuchikama K, Lowery C, Janda K. Probing autoinducer-2 based quorum sensing: the biological consequences of molecules unable to traverse equilibrium states. J Org Chem. 2011;76:6981-9 pubmed publisher
  9. Belinskaya T, Pattabiraman N, diTargiani R, Choi M, Saxena A. Differences in amino acid residues in the binding pockets dictate substrate specificities of mouse senescence marker protein-30, human paraoxonase1, and squid diisopropylfluorophosphatase. Biochim Biophys Acta. 2012;1824:701-10 pubmed publisher
    ..We purified SMP-30 from mouse (Mo) liver and compared its hydrolytic activity towards various esters, lactones, and G-type nerve agents with that of human paraoxonase1 (Hu PON1) and squid diisopropylfluorophosphatase (DFPase)..

More Information

Publications62

  1. Toh S, Kamiya Y, Kawakami N, Nambara E, McCourt P, Tsuchiya Y. Thermoinhibition uncovers a role for strigolactones in Arabidopsis seed germination. Plant Cell Physiol. 2012;53:107-17 pubmed publisher
    ..Thus, our simple assay system using Arabidopsis thermoinhibition allows comparisons to determine similarities and differences between parasitic plants and model experimental systems for the use of strigolactones. ..
  2. Littrell M, Gatakaa H, Evance I, Poyer S, Njogu J, Solomon T, et al. Monitoring fever treatment behaviour and equitable access to effective medicines in the context of initiatives to improve ACT access: baseline results and implications for programming in six African countries. Malar J. 2011;10:327 pubmed publisher
    ..Supporting interventions to inform caregiver demand for ACT and to improve provider behaviour in both the public and private sectors are needed to achieve maximum gains in the context of improved access to effective treatment. ..
  3. Blagojević P, Radulović N. Conformational analysis of antistaphylococcal sesquiterpene lactones from Inula helenium essential oil. Nat Prod Commun. 2012;7:1407-10 pubmed
    Isomeric eudesmane-type sesquiterpene lactones: alantolactone (1), isoalantolactone (2) and diplophyllin (3), the main constituents of Inula helenium L. root essential oil, are strong antistaphylococcal agents...
  4. Ruyter Spira C, Al Babili S, van der Krol S, Bouwmeester H. The biology of strigolactones. Trends Plant Sci. 2013;18:72-83 pubmed publisher
  5. Brewer P, Koltai H, Beveridge C. Diverse roles of strigolactones in plant development. Mol Plant. 2013;6:18-28 pubmed publisher
    ..This hormonal response is a key adaption that radically alters whole-plant architecture in order to optimize growth and development under diverse environmental conditions...
  6. Akweongo P, Agyei Baffour P, Sudhakar M, Simwaka B, Konate A, Adongo P, et al. Feasibility and acceptability of ACT for the community case management of malaria in urban settings in five African sites. Malar J. 2011;10:240 pubmed publisher
    ..Urban CCMm is feasible, but it struggles against other sources of established healthcare providers. Innovation is required by everyone to make it viable. ..
  7. Zhang Q, Lu Y, Ding Y, Zhai J, Ji Q, Ma W, et al. Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells. J Med Chem. 2012;55:8757-69 pubmed publisher
    ..Here we report a series of guaianolide sesquiterpene lactones (GSLs) and their derivatives that can selectively eradicate acute myelogenous leukemia (AML) stem or progenitor ..
  8. Guan J, Koch K, Suzuki M, Wu S, Latshaw S, Petruff T, et al. Diverse roles of strigolactone signaling in maize architecture and the uncoupling of a branching-specific subnetwork. Plant Physiol. 2012;160:1303-17 pubmed publisher
    ..Our findings indicate that in maize, uncoupling of the Tb1 subnetwork from SL signaling has profoundly altered the balance between conserved roles of SLs in branching and diverse aspects of plant architecture...
  9. Guo M, Gamby S, Nakayama S, Smith J, Sintim H. A pro-drug approach for selective modulation of AI-2-mediated bacterial cell-to-cell communication. Sensors (Basel). 2012;12:3762-72 pubmed publisher
    ..Such differences could be utilized to selectively target QS in specific bacteria amongst a consortium of other species that also use AI-2 signaling. ..
  10. Lei J, Yu J, Yin Y, Liu Y, Zou G. Alantolactone induces activation of apoptosis in human hepatoma cells. Food Chem Toxicol. 2012;50:3313-9 pubmed publisher
    ..In addition, a significant and progressive increase in the level of p53 protein in alantolactone-treated cells was observed. Taken together, our data suggest that alantolactone could be developed as an agent against human liver cancer. ..
  11. Zhu J, Hixon M, Globisch D, Kaufmann G, Janda K. Mechanistic insights into the LsrK kinase required for autoinducer-2 quorum sensing activation. J Am Chem Soc. 2013;135:7827-30 pubmed publisher
  12. Shinohara N, Taylor C, Leyser O. Strigolactone can promote or inhibit shoot branching by triggering rapid depletion of the auxin efflux protein PIN1 from the plasma membrane. PLoS Biol. 2013;11:e1001474 pubmed publisher
  13. Alder A, Jamil M, Marzorati M, Bruno M, Vermathen M, Bigler P, et al. The path from ?-carotene to carlactone, a strigolactone-like plant hormone. Science. 2012;335:1348-51 pubmed publisher
    Strigolactones, phytohormones with diverse signaling activities, have a common structure consisting of two lactones connected by an enol-ether bridge...
  14. Armbruster C, Pang B, Murrah K, Juneau R, Perez A, Weimer K, et al. RbsB (NTHI_0632) mediates quorum signal uptake in nontypeable Haemophilus influenzae strain 86-028NP. Mol Microbiol. 2011;82:836-50 pubmed publisher
    ..Based on these data, we conclude that in NTHI 86-028NP, RbsB is a LuxS/AI-2 regulated protein that is required for uptake of and response to AI-2...
  15. Srivastava A, Talaue M, Liu S, Degen D, Ebright R, Sineva E, et al. New target for inhibition of bacterial RNA polymerase: 'switch region'. Curr Opin Microbiol. 2011;14:532-43 pubmed publisher
    ..This review summarizes the switch region, switch-region inhibitors, and implications for antibacterial drug discovery. ..
  16. Kuang H, Yang B, Xia Y, Wang Q. Two new withanolide lactones from flos daturae. Molecules. 2011;16:5833-9 pubmed publisher
  17. Agusti J, Herold S, Schwarz M, Sanchez P, Ljung K, Dun E, et al. Strigolactone signaling is required for auxin-dependent stimulation of secondary growth in plants. Proc Natl Acad Sci U S A. 2011;108:20242-7 pubmed publisher
  18. Ueno K, Nomura S, Muranaka S, Mizutani M, Takikawa H, Sugimoto Y. Ent-2'-epi-Orobanchol and its acetate, as germination stimulants for Striga gesnerioides seeds isolated from cowpea and red clover. J Agric Food Chem. 2011;59:10485-90 pubmed publisher
    ..Identity of the stimulants produced by cowpea to those produced by red clover (Trifolium pratense) was confirmed...
  19. Xiang D, Kolb P, Fedorov A, Xu C, Fedorov E, Narindoshivili T, et al. Structure-based function discovery of an enzyme for the hydrolysis of phosphorylated sugar lactones. Biochemistry. 2012;51:1762-73 pubmed publisher
    ..Enzymes within cog1735 of the AHS have previously been shown to catalyze the hydrolysis of substituted lactones. Computational docking of the high-energy intermediate form of the KEGG database to the three-dimensional ..
  20. Stojanović Radić Z, Comic L, Radulovic N, Blagojević P, Denić M, Miltojević A, et al. Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage. Eur J Clin Microbiol Infect Dis. 2012;31:1015-25 pubmed publisher
    ..Sesquiterpene lactones were found to be the most active principles of the oil, whose eudesmane core olefinic bonds, along with the ?,?-..
  21. Wu M, Tao Y, Liu X, Zang J. Structural basis for phosphorylated autoinducer-2 modulation of the oligomerization state of the global transcription regulator LsrR from Escherichia coli. J Biol Chem. 2013;288:15878-87 pubmed publisher
    ..Based on these observations, we propose that phosphorylated autoinducer-2 triggers the disassembly of the LsrR tetramer to activate the transcription of its target genes...
  22. Rubensam G, Barreto F, Hoff R, Kist T, Pizzolato T. A liquid-liquid extraction procedure followed by a low temperature purification step for the analysis of macrocyclic lactones in milk by liquid chromatography-tandem mass spectrometry and fluorescence detection. Anal Chim Acta. 2011;705:24-9 pubmed publisher
    In this work a method is proposed and demonstrated for the analysis of the macrocyclic lactones abamectin, doramectin, eprinomectin, ivermectin and moxidectin in bovine milk by liquid chromatography coupled to mass spectrometry (LC-MS/MS) ..
  23. Morris M, Lane P, Lee K, PARKS D. An integrated analysis of liver safety data from orlistat clinical trials. Obes Facts. 2012;5:485-94 pubmed publisher
    ..This shows that there is no signal for hepatic damage in clinical studies of orlistat. While idiosyncratic liver injury following exposure to orlistat cannot be excluded, it is likely to be extremely rare. ..
  24. Li Y, Ding Y, Wang J, Su Y, Wang X. Pd-catalyzed C-H lactonization for expedient synthesis of biaryl lactones and total synthesis of cannabinol. Org Lett. 2013;15:2574-7 pubmed publisher
    A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C-H activation/C-O cyclization to construct biaryl lactones has been developed...
  25. Qiu F, Friesen J, McAlpine J, Pauli G. Design of countercurrent separation of Ginkgo biloba terpene lactones by nuclear magnetic resonance. J Chromatogr A. 2012;1242:26-34 pubmed publisher
    Terpene lactones such as bilobalide, ginkgolides A, B, C, and J are major bioactive compounds of Ginkgo biloba L. Purification of these compounds is tedious due to their similar chemical properties...
  26. Kosoglou T, Reyderman L, Tiessen R, van Vliet A, Fales R, Keller R, et al. Pharmacodynamics and pharmacokinetics of the novel PAR-1 antagonist vorapaxar (formerly SCH 530348) in healthy subjects. Eur J Clin Pharmacol. 2012;68:249-58 pubmed publisher
    ..Adverse events were generally mild, transient, and unrelated to dose. Vorapaxar provided rapid and sustained dose-related inhibition of platelet aggregation without affecting bleeding or clotting times. ..
  27. Kretzschmar T, Kohlen W, Sasse J, Borghi L, Schlegel M, Bachelier J, et al. A petunia ABC protein controls strigolactone-dependent symbiotic signalling and branching. Nature. 2012;483:341-4 pubmed publisher
    ..PDR1 is the first known component in strigolactone transport, providing new opportunities for investigating and manipulating strigolactone-dependent processes...
  28. Roy V, Meyer M, Smith J, Gamby S, Sintim H, Ghodssi R, et al. AI-2 analogs and antibiotics: a synergistic approach to reduce bacterial biofilms. Appl Microbiol Biotechnol. 2013;97:2627-38 pubmed publisher
  29. Duraipandiyan V, Al Harbi N, Ignacimuthu S, Muthukumar C. Antimicrobial activity of sesquiterpene lactones isolated from traditional medicinal plant, Costus speciosus (Koen ex.Retz.) Sm. BMC Complement Altern Med. 2012;12:13 pubmed publisher
    ..The plant has been found to possess diverse pharmacological activities. Rhizomes are used to treat pneumonia, rheumatism, dropsy, urinary diseases, jaundice, skin diseases and leaves are used to treat mental disorders...
  30. Dun E, de Saint Germain A, Rameau C, Beveridge C. Dynamics of strigolactone function and shoot branching responses in Pisum sativum. Mol Plant. 2013;6:128-40 pubmed publisher
    ..Altogether, these results reveal new insights into the dynamics of SL function and support the premise that SLs or SL-derived metabolites function dynamically as a shoot branching hormone and that they act directly in axillary buds...
  31. Schomburg C, Schuehly W, da Costa F, Klempnauer K, Schmidt T. Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships. Eur J Med Chem. 2013;63:313-20 pubmed publisher
    ..We recently discovered that some sesquiterpene lactones suppress Myb-dependent gene expression which is a new mechanism for these natural products' potential anti-cancer ..
  32. Li Y, Ni Z, Zhu M, Dong M, Wang S, Shi Q, et al. Antitumour activities of sesquiterpene lactones from Inula helenium and Inula japonica. Z Naturforsch C. 2012;67:375-80 pubmed
    Eight sesquiterpene lactones were isolated from the roots of Inula helenium and flowers of I. japonica...
  33. Jamil M, Rodenburg J, Charnikhova T, Bouwmeester H. Pre-attachment Striga hermonthica resistance of New Rice for Africa (NERICA) cultivars based on low strigolactone production. New Phytol. 2011;192:964-75 pubmed publisher
  34. Liu G, Shirley M, Romo D. A diastereoselective, nucleophile-promoted aldol-lactonization of ketoacids leading to bicyclic-?-lactones. J Org Chem. 2012;77:2496-500 pubmed publisher
    ..This more practical protocol shortens reaction times for the construction of bicyclic ?-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsCl) as ..
  35. Li Z, Yao L, Li J, Zhang W, Wu X, Liu Y, et al. Celastrol nanoparticles inhibit corneal neovascularization induced by suturing in rats. Int J Nanomedicine. 2012;7:1163-73 pubmed publisher
    ..CNPs significantly inhibited suture-induced CNV by suppressing macrophage infiltration and the expression of vascular endothelial growth factor and matrix metalloproteinase 9 in the rat cornea. ..
  36. Ramirez A, Saillard N, Yang T, Franssen M, Bouwmeester H, Jongsma M. Biosynthesis of sesquiterpene lactones in pyrethrum (Tanacetum cinerariifolium). PLoS ONE. 2013;8:e65030 pubmed publisher
    ..Pyrethrum flowers also contain other potential defense compounds, particularly sesquiterpene lactones (STLs), which represent problematic allergenic residues in the extracts that are removed by the pyrethrum ..
  37. Olsen P, Borke T, Odelius K, Albertsson A. ?-Decalactone: a thermoresilient and toughening comonomer to poly(L-lactide). Biomacromolecules. 2013;14:2883-90 pubmed publisher
    ..These properties result in phase separation to soft and hard domains, which provides the basis for the elastomeric behavior. ..
  38. Zhang C, Tian X, Luo Y, Meng X. Ginkgolide B attenuates ethanol-induced neurotoxicity through regulating NADPH oxidases. Toxicology. 2011;287:124-30 pubmed publisher
    ..Moreover, expression and activities of NADPH oxidases were down-regulated by GB. These results indicate that ethanol-induced neurotoxicity is ameliorated by GB mainly through regulating expression and activity of NADPH oxidases. ..
  39. Amaya S, Pereira J, Borkosky S, Valdez J, Bardon A, Arena M. Inhibition of quorum sensing in Pseudomonas aeruginosa by sesquiterpene lactones. Phytomedicine. 2012;19:1173-7 pubmed publisher
    Six sesquiterpene lactones (SLs) of the goyazensolide and isogoyazensolide-type isolated from the Argentine herb Centratherum punctatum were evaluated on their ability to inhibit virulence factors of Pseudomonas aeruginosa ATCC 27853...
  40. Sgariglia M, Soberón J, Cabanes A, Sampietro D, Vattuone M. Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark. J Ethnopharmacol. 2013;147:63-73 pubmed publisher
    ..Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their "vulnerary" properties...
  41. Khan M, Yi F, Rasul A, Li T, Wang N, Gao H, et al. Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction. IUBMB Life. 2012;64:783-94 pubmed publisher
    ..Therefore, alantolactone may become a potential lead compound for future development of antiglioma therapy. ..
  42. Minagawa S, Inami H, Kato T, Sawada S, Yasuki T, Miyairi S, et al. RND type efflux pump system MexAB-OprM of Pseudomonas aeruginosa selects bacterial languages, 3-oxo-acyl-homoserine lactones, for cell-to-cell communication. BMC Microbiol. 2012;12:70 pubmed publisher
    ..Gram-negative bacteria use a variety of self-produced autoinducers such as acylated homoserine lactones (acyl-HSLs) as signal compounds for quorum sensing (QS) within and between bacterial species...
  43. Geetha B, Nair M, Latha P, Remani P. Sesquiterpene lactones isolated from Elephantopus scaber L. inhibits human lymphocyte proliferation and the growth of tumour cell lines and induces apoptosis in vitro. J Biomed Biotechnol. 2012;2012:721285 pubmed publisher
    ..The results, therefore, indicate that the antiproliferative property of deoxyelephantopin and isodeoxyelephantopin could be used in regimens for treating tumors with extensive proliferative potencies. ..
  44. Andberg M, Maaheimo H, Boer H, Penttil M, Koivula A, Richard P. Characterization of a novel Agrobacterium tumefaciens galactarolactone cycloisomerase enzyme for direct conversion of D-galactarolactone to 3-deoxy-2-keto-L-threo-hexarate. J Biol Chem. 2012;287:17662-71 pubmed publisher
  45. Foo E, Davies N. Strigolactones promote nodulation in pea. Planta. 2011;234:1073-81 pubmed publisher
  46. Rui F, Marques J, Miller S, Maycock C, Xavier K, Ventura M. Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli. Bioorg Med Chem. 2012;20:249-56 pubmed publisher
    ..65?M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. ..
  47. O Connell K, Gatakaa H, Poyer S, Njogu J, Evance I, Munroe E, et al. Got ACTs? Availability, price, market share and provider knowledge of anti-malarial medicines in public and private sector outlets in six malaria-endemic countries. Malar J. 2011;10:326 pubmed publisher
    ..The data will also be useful for monitoring the impact of interventions such as the Affordable Medicines Facility for malaria. ..
  48. Xiao D, Shi D, Yang D, Barthel B, Koch T, Yan B. Carboxylesterase-2 is a highly sensitive target of the antiobesity agent orlistat with profound implications in the activation of anticancer prodrugs. Biochem Pharmacol. 2013;85:439-47 pubmed publisher
    ..In addition, orlistat has been linked to various types of organ toxicities, and this study provides an alternative target potentially involved in these toxicological responses. ..
  49. Hamiaux C, Drummond R, Janssen B, Ledger S, Cooney J, Newcomb R, et al. DAD2 is an ?/? hydrolase likely to be involved in the perception of the plant branching hormone, strigolactone. Curr Biol. 2012;22:2032-6 pubmed publisher
    ..They are carotenoid-derived lactones, synthesized in the roots and transported acropetally to modulate axillary bud outgrowth (i.e., branching)...
  50. Wei W, Huang H, Zhao S, Liu W, Liu C, Chen L, et al. Alantolactone induces apoptosis in chronic myelogenous leukemia sensitive or resistant to imatinib through NF-?B inhibition and Bcr/Abl protein deletion. Apoptosis. 2013;18:1060-70 pubmed publisher
    ..Collectively, these findings suggest that alantolactone is a promising potent agent to fight against CML cells via the inhibition of the NF-?B signaling pathway and depletion of the Bcr/Abl protein. ..
  51. Waters M, Nelson D, Scaffidi A, Flematti G, Sun Y, Dixon K, et al. Specialisation within the DWARF14 protein family confers distinct responses to karrikins and strigolactones in Arabidopsis. Development. 2012;139:1285-95 pubmed publisher
    ..Our results support the existence of an endogenous, butenolide-based signalling mechanism that is distinct from the strigolactone pathway, providing a molecular basis for the adaptive response of plants to smoke. ..
  52. Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara Tsukashima A, Kiyohara H, et al. In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). J Nat Med. 2012;66:558-61 pubmed publisher
    ..to discover new antitrypanosomal compounds, eight known plant compounds (three phenolic compounds and five kawa lactones) were evaluated for in vitro activity against Trypanosoma brucei brucei...
  53. Braun N, de Saint Germain A, Pillot J, Boutet Mercey S, Dalmais M, Antoniadi I, et al. The pea TCP transcription factor PsBRC1 acts downstream of Strigolactones to control shoot branching. Plant Physiol. 2012;158:225-38 pubmed publisher
    ..This phenotype indicates a localized regulation of branching at these nodes specific to pea...