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manoalide
2(5H)-furanone, 4-(3,6-dihydro-6-hydroxy-5-(4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-

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Name:(2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
CAS Number: 75088-80-1Picture of molecule3D/inchi
FDA UNII: E1DK0157K9
Nikkaji Web:J11.639D
MDL:MFCD00153826
XlogP3-AA:3.50 (est)
Molecular Weight:416.55792000
Formula:C25 H36 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 609.60 °C. @ 760.00 mm Hg (est)
Flash Point: 398.00 °F. TCC ( 203.30 °C. ) (est)
logP (o/w): 5.190 (est)
Soluble in:
 water, 0.01023 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Manoalide
Santa Cruz Biotechnology
For experimental / research use only.
Manoalide 98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Manoalide oil, ≥75% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for manoalide usage levels up to:
 not for fragrance use.
 
Recommendation for manoalide flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6437368
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
Chemidplus:0075088801
 
References:
 (2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6437368
Pubchem (sid):135066692
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C17156
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2(5H)-furanone, 4-((2R,6R)-3,6-dihydro-6-hydroxy-5-((3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-, (5R)-
2(5H)-furanone, 4-(3,6-dihydro-6-hydroxy-5-(4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-
(2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
 

Articles:

PubMed:Evaluation of single and joint effect of metabolites isolated from marine sponges, Fasciospongia cavernosa and Axinella donnani on antimicrobial properties.
PubMed:A comprehensive strategy to discover inhibitors of the translesion synthesis DNA polymerase κ.
PubMed:Inhibition of hepatitis C virus NS3 helicase by manoalide.
PubMed:Therapeutic application of natural inhibitors against snake venom phospholipase A(2).
PubMed:Influence of experimental subarachnoid hemorrhage on nicotine-induced contraction of the rat basilar artery in relation to arachidonic acid metabolites signaling pathway.
PubMed:Anti-biofilm compounds derived from marine sponges.
PubMed:Hippolides A-H, acyclic manoalide derivatives from the marine sponge Hippospongia lachne.
PubMed:A ClpP protein model as tuberculosis target for screening marine compounds.
PubMed:Marine natural products targeting phospholipases A2.
PubMed:Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance.
PubMed:Retinoids as a perspective in treatment of Alzheimer's disease.
PubMed:ESI FTICR-MS analysis of larvae from the marine sponge Luffariella variabilis.
PubMed:Deoxymanoalides from the nudibranch Chromodoris willani.
PubMed:Aromatic cyclic peroxides and related keto-compounds from the Plakortis sp. component of a sponge consortium.
PubMed:Coordinate regulation of TLR-mediated arachidonic acid mobilization in macrophages by group IVA and group V phospholipase A2s.
PubMed:24-O-ethylmanoalide, a manoalide-related sesterterpene from the marine sponge Luffariella cf. variabilis.
PubMed:Clinical status of anti-cancer agents derived from marine sources.
PubMed:Nox1 downstream of 12-lipoxygenase controls cell proliferation but not cell spreading of colon cancer cells.
PubMed:Phospholipase A2-like activity of human bocavirus VP1 unique region.
PubMed:Quorum sensing antagonism from marine organisms.
PubMed:Production of manoalide and its analogues by the sponge Luffariella variabilis Is hardwired.
PubMed:Scalaradial, a dialdehyde-containing marine metabolite that causes an unexpected noncovalent PLA2 Inactivation.
PubMed:Activation and inactivation of the volume-sensitive taurine leak pathway in NIH3T3 fibroblasts and Ehrlich Lettre ascites cells.
PubMed:Effect of serum from cardiovascular patients on catalytic activity of secretory phospholipase A2 (IIA).
PubMed:Acetylated sesterterpenes from the Great Barrier Reef sponge Luffariella variabilis.
PubMed:Roles of phospholipase A2 isoforms in swelling- and melittin-induced arachidonic acid release and taurine efflux in NIH3T3 fibroblasts.
PubMed:Manoalide derivatives from a sponge, Luffariella sp.
PubMed:PLA2 inhibitory activity of marine sesterterpenoids cladocorans, their diastereomers and analogues.
PubMed:Phospholipase A2 is involved in muscarinic receptor-mediated sAPPalpha release independently of cyclooxygenase or lypoxygenase activity in SH-SY5Y cells.
PubMed:L-selectin expression on neutrophils from allergic patients.
PubMed:Late-gestation rat myometrial cells express multiple isoforms of phospholipase A2 that mediate PCB 50-induced release of arachidonic acid with coincident prostaglandin production.
PubMed:The catalytically active secretory phospholipase A2 type IIA is involved in restenosis development after PTCA in human coronary arteries and generation of atherogenic LDL.
PubMed:A phospholipase C-dependent intracellular Ca2+ release pathway mediates the capsaicin-induced apoptosis in HepG2 human hepatoma cells.
PubMed:Role of intracellular Ca2+ signal in the ascorbate-induced apoptosis in a human hepatoma cell line.
PubMed:Antitubercular sesterterpenes from the Thai sponge Brachiaster sp.
PubMed:Lipoxygenase-dependent superoxide release in skeletal muscle.
PubMed:Characterisation of some pharmacological effects of the venom from Vipera lebetina.
PubMed:Advanced glycation end products stimulate an enhanced neutrophil respiratory burst mediated through the activation of cytosolic phospholipase A2 and generation of arachidonic Acid.
PubMed:Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement.
PubMed:Modulatory effect of bolinaquinone, a marine sesquiterpenoid, on acute and chronic inflammatory processes.
PubMed:Role of intracellular Ca2+ in endothelium-dependent contraction and relaxation of rabbit intrapulmonary arteries.
PubMed:Molecular basis of phospholipase A2 inhibition by petrosaspongiolide M.
PubMed:Inhibition of crotoxin phospholipase A(2) activity by manoalide associated with inactivation of crotoxin toxicity and dissociation of the heterodimeric neurotoxic complex.
PubMed:4-Bromophenacyl bromide induces Ca2+ influx in human gingival fibroblasts.
PubMed:The VP1 unique region of parvovirus B19 and its constituent phospholipase A2-like activity.
PubMed:ATP-induced histamine release is in part related to phospholipase A2-mediated arachidonic acid metabolism in rat peritoneal mast cells.
PubMed:Protamine augments stretch induced calcium increase in vascular endothelium.
PubMed:New sesquiterpene derivatives from the sponge Dysidea species with a selective inhibitor profile against human phospholipase A2 and other leukocyte functions.
PubMed:Dysidotronic acid, a new sesquiterpenoid, inhibits cytokine production and the expression of nitric oxide synthase.
PubMed:Effects of mercuric chloride exposure on the glutamate uptake by cultured retinal pigment epithelial cells.
PubMed:The involvement of phospholipase A(2) in ethanol-induced gastric muscle contraction.
PubMed:Role of pertussis toxin-sensitive G-proteins in intracellular Ca2+ release and apoptosis induced by inhibiting cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channels in HepG2 human hepatoblastoma cells.
PubMed:Activation of human neutrophils by the plant lectin Viscum album agglutinin-I: modulation of de novo protein synthesis and evidence that caspases are involved in induction of apoptosis.
PubMed:Mediation by platelet-activating factor of 12-hydroxyeicosatetraenoic acid-induced cytosolic free calcium concentration elevation in neutrophils.
PubMed:PLA(2) dependence of diaphragm mitochondrial formation of reactive oxygen species.
PubMed:Light activation of phospholipase A2 in the photoreceptor of the crayfish (Procambarus clarkii).
PubMed:Tumor necrosis factor-alpha augments contraction and cytosolic Ca(2+) sensitivity through phospholipase A(2) in bovine tracheal smooth muscle.
PubMed:New pyridinium alkaloids from a marine sponge of the genus Spongia with a human phospholipase A(2) inhibitor profile.
PubMed:Simultaneous inhibition of renal phospholipase A(2) and glutathione synthesis by manoalide and DL-buthionine sulfoximine induces acute tubular dysfunction in rats.
PubMed:Phospholipase A2 is involved in chemotaxis of human leukocytes.
PubMed:Activation of cPLA2 in vascular smooth muscle.
PubMed:An 18.5 kDa protein from the amebocyte of Limulus polyphemus, homologous to the previously described amebocyte aggregation factor, expresses alternative phospholipase A2 activity.
PubMed:Formation of reactive oxygen species by the contracting diaphragm is PLA(2) dependent.
PubMed:Effect of manoalide on apoptosis induced by deprivation of growth factors in vascular endothelial cells.
PubMed:Effect of protein kinase C and phospholipase A2 inhibitors on the impaired ability of human diabetic platelets to cause vasodilation.
PubMed:Role of prostaglandin H synthase isoforms in murine ear edema induced by phorbol ester application on skin.
PubMed:Stimulation of pregnant rat uterine contraction by the polychlorinated biphenyl (PCB) mixture aroclor 1242 may be mediated by arachidonic acid release through activation of phospholipase A2 enzymes.
PubMed:Involvement of phospholipase A2 activation in anthrax lethal toxin-induced cytotoxicity.
PubMed:Manoalide.
PubMed:Cyclosporin A, but not FK506, increases arachidonic acid release and inhibits proliferation of pituitary corticotrope tumor cells.
PubMed:Effects of petrosaspongiolide M, a novel phospholipase A2 inhibitor, on acute and chronic inflammation.
PubMed:Modulation of acute and chronic inflammatory processes by cacospongionolide B, a novel inhibitor of human synovial phospholipase A2.
PubMed:Phospholipase A2 is not responsible for lysophosphatidylcholine-induced damage in cardiomyocytes.
PubMed:Manoalide, a phospholipase A2 inhibitor, inhibits arachidonate incorporation and turnover in brain phospholipids of the awake rat.
PubMed:Calcium influx inhibition by steroids and analogs in C2C12 skeletal muscle cells.
PubMed:Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
PubMed:A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
PubMed:Effects of local anesthetics on acetylcholine-induced desensitization of guinea pig ileal longitudinal muscle.
PubMed:Role of protein kinase C alpha in endothelin-1 stimulation of cytosolic phospholipase A2 and arachidonic acid release in cultured cat iris sphincter smooth muscle cells.
PubMed:Paraquat-induced phosphatidylserine oxidation and apoptosis are independent of activation of PLA2.
PubMed:Petrosaspongiolides M-R: new potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra.
PubMed:Norepinephrine stimulates arachidonic acid release from vascular smooth muscle via activation of cPLA2.
PubMed:Investigation on the effect of experimental phospholipase A2 inhibitors on the formyl-methionyl-leucyl-phenylalanine-stimulated chemotaxis of human leukocytes in vitro.
PubMed:Novel aspect on metal fume fever: zinc stimulates oxygen radical formation in human neutrophils.
PubMed:Intracellular Ca2+ homeostasis in trypomastigotes of Trypanosoma cruzi.
PubMed:A phospholipase A2-related snake venom (from Crotalus durissus terrificus) stimulates neuroendocrine and immune functions: determination of different sites of action.
PubMed:Purification and characterization of a catalytic domain of rat intestinal phospholipase B/lipase associated with brush border membranes.
PubMed:Endotoxin-induced macrophage gene expression depends on platelet-activating factor.
PubMed:Endothelin-1 stimulates the release of arachidonic acid and prostaglandins in cultured human ciliary muscle cells: activation of phospholipase A2.
PubMed:The mechanisms of compound 48/80-induced superoxide generation mediated by A-kinase in rat peritoneal mast cells.
PubMed:Protection against methoxyacetic-acid-induced spermatocyte apoptosis with calcium channel blockers in cultured rat seminiferous tubules: possible mechanisms.
PubMed:Inhibitors of phospholipase promote apoptosis of human endothelial cells.
PubMed:Upregulation of Na(+)-K(+)-2Cl- cotransporter activity in rat parotid acinar cells by muscarinic stimulation.
PubMed:Luffasterols A-C, 9,11-secosterols from the Palauan sponge Luffariella sp.
PubMed:Pharmacological targeting of signaling pathways in protein kinase C-stimulated superoxide generation in neutrophil-like HL-60 cells: effect of phorbol ester, arachidonic acid and inhibitors of kinase(s), phosphatase(s) and phospholipase A2.
PubMed:Regulation of intracellular pH by phospholipase A2 and protein kinase C upon neutrophil adhesion to solid substrata.
PubMed:Endothelin-1-evoked arachidonic acid release: a Ca(2+)-dependent pathway.
PubMed:The effects of the phospholipase A2 inhibitor, manoalide, on cartilage degradation, stromelysin expression, and synovial fluid cell count induced by intraarticular injection of human recombinant interleukin-1 alpha in the rabbit.
PubMed:Effect of manoalide on human 5-lipoxygenase activity.
PubMed:Involvement of secretory phospholipase A2 activity in the zymosan rat air pouch model of inflammation.
PubMed:Prostaglandin E2 production by endotoxin-stimulated alveolar macrophages is regulated by phospholipase C pathways.
PubMed:Phospholipase A2 is involved in the mechanism of activation of neutrophils by polychlorinated biphenyls.
PubMed:Possible involvement of endothelial leukotrienes in acetylcholine-induced contraction in rabbit coronary artery.
PubMed:The effects of two phospholipase A2 inhibitors on the neuromuscular blocking activities of homologous phospholipases A2 from the venom of Pseudechis australis, the Australian king brown snake.
PubMed:Regulation of prostaglandin H synthase 2 expression in human monocytes by the marine natural products manoalide and scalaradial. Novel effects independent of inhibition of lipid mediator production.
PubMed:Identification of two specific lysines responsible for the inhibition of phospholipase A2 by manoalide.
PubMed:Modulation of superoxide generation in in vivo lipopolysaccharide-primed rat alveolar macrophages by arachidonic acid and inhibitors of protein kinase C, phospholipase A2, protein serine-threonine phosphatase(s), protein tyrosine kinase(s) and phosphatase(s).
PubMed:Retinoic acid induced death of ovarian carcinoma cells correlates with c-myc stimulation.
PubMed:Chemical modification and inactivation of phospholipases A2 by a manoalide analogue.
PubMed:Endothelium-dependent contraction induced by acetylcholine in isolated rat renal arteries.
PubMed:Sodium orthovanadate increases phospholipase A2 activity in isolated rat fat pads: a role of phospholipase A2 in the vanadate-stimulated release of lipoprotein lipase activity.
PubMed:Cellular and topical in vivo inflammatory murine models in the evaluation of inhibitors of phospholipase A2.
PubMed:The endoperoxides/TxA2 analogue, U46619, inhibits human polymorphonuclear leukocyte function.
PubMed:Specificity of phospholipase D activation by cholecystokinin and phorbol myristate acetate but not by carbamylcholine and A23187 in rat pancreatic acini.
PubMed:Regulation of phospholipase A2 enzymes: selective inhibitors and their pharmacological potential.
PubMed:Mechanically induced calcium mobilization in cultured endothelial cells is dependent on actin and phospholipase.
PubMed:Biochemical and pharmacological comparison of a cytosolic, high molecular weight phospholipase A2, human synovial fluid phospholipase A2 and CoA-independent transacylase.
PubMed:Phospholipase A2 activation in cultured mouse hepatocytes exposed to tumor necrosis factor-alpha.
PubMed:Alpha 1-adrenoceptors in rat dorsal raphe neurons: regulation of two potassium conductances.
PubMed:Inactivation of bee venom phospholipase A2 by a sesquiterpene furanoic acid marine natural product.
PubMed:Rapid protein synthesis and turnover is involved in interleukin-1-induced relaxation of the rabbit isolated mesenteric artery. Analysis of the arachidonate cascade.
PubMed:Rapid induction of arachidonic acid release by monocyte chemotactic protein-1 and related chemokines. Role of Ca2+ influx, synergism with platelet-activating factor and significance for chemotaxis.
PubMed:Marine natural products. XXXII. Absolute configurations of C-4 of the manoalide family, biologically active sesterterpenes from the marine sponge Hyrtios erecta.
PubMed:An endothelium-dependent contraction in canine mesenteric artery caused by caffeine.
PubMed:Acyl transfer reactions associated with cis Golgi apparatus of rat liver.
PubMed:Modulation of superoxide generation in in vivo lipopolysaccharide-primed Kupffer cells by staurosporine, okadaic acid, manoalide, arachidonic acid, genistein and sodium orthovanadate.
PubMed:Initiation of RVD response in human platelets: mechanical-biochemical transduction involves pertussis-toxin-sensitive G protein and phospholipase A2.
PubMed:Phospholipase A2 activation influences the processing and secretion of the amyloid precursor protein.
PubMed:Regulation of CD11b/CD18 expression in human neutrophils by phospholipase A2.
PubMed:Involvement of phospholipase D in caerulein-induced phosphatidylcholine hydrolysis in rat pancreatic acini.
PubMed:Modulation of superoxide anion generation by manoalide, arachidonic acid and staurosporine in liver infiltrated neutrophils in a rat model of endotoxemia.
PubMed:Arachidonic acid, a growth signal in murine P815 mastocytoma cells.
PubMed:Molecular model of the interaction of bee venom phospholipase A2 with manoalide.
PubMed:Botulinum toxin inhibits arachidonic acid release associated with acetylcholine release from PC12 cells.
PubMed:A requirement for membrane-associated phospholipase A2 in platelet cytotoxicity activated by receptors for immunoglobulin G and complement.
PubMed:Degradation of membrane phospholipids in the cultured human astroglial cell line UC-11MG during ATP depletion.
PubMed:Luffariolides F and G, new manoalide derivatives from the Okinawan marine sponge Luffariella sp.
PubMed:Inhibition of phospholipase A2 purified from human herniated disc.
PubMed:The novel natural product YM-26567-1 [(+)-trans-4-(3-dodecanoyl-2,4,6- trihydroxyphenyl)-7-hydroxy-2-(4-hydroxyphenyl)chroman]: a competitive inhibitor of group II phospholipase A2.
PubMed:Phospholipase A2 inhibitors from marine organisms.
PubMed:Phospholipase activation during monocyte adherence and spreading.
PubMed:Phospholipase A2 inhibition by alkylbenzoylacrylic acids.
PubMed:Natural products. Sponges to wipe away pain.
PubMed:Four new antibacterial sesterterpenes from a marine sponge of the genus Luffariella.
PubMed:Agonist-sensitive and -insensitive intracellular Ca2+ pools. Separate Ca(2+)-releasing mechanisms revealed by manoalide and benzohydroquinone.
PubMed:Kinetic characterization of phospholipase A2 modified by manoalogue.
PubMed:Inhibition of venom phospholipases A2 by manoalide and manoalogue. Stoichiometry of incorporation.
PubMed:[Inhibitors for enzymes involving arachidonate cascade].
PubMed:Antiflammin-2 (HDMNKVLDL) does not inhibit phospholipase A2 activities.
PubMed:AGN 190383, a novel phospholipase inhibitor with topical anti-inflammatory activity.
PubMed:Arachidonic acid is essential for IgG Fc receptor-mediated phagocytosis by human monocytes.
PubMed:Purification and characterization of a soluble phospholipase A2 from guinea pig lung.
PubMed:Inhibition by manoalide of fMLP-stimulated elastase release from human neutrophils.
PubMed:Inactivation of human synovial fluid phospholipase A2 by the marine natural product, manoalide.
PubMed:Macrophage phospholipase A2 activity and eicosanoid production: studies with phospholipase A2 inhibitors in P388D1 cells.
PubMed:Manoalide: structure-activity studies and definition of the pharmacophore for phospholipase A2 inactivation.
PubMed:Inhibition studies on the membrane-associated phospholipase A2 in vitro and prostaglandin E2 production in vivo of the macrophage-like P388D1 cell. Effects of manoalide, 7,7-dimethyl-5,8-eicosadienoic acid, and p-bromophenacyl bromide.
PubMed:Luffolide, a novel anti-inflammatory terpene from the sponge Luffariella sp..
PubMed:Platelet-activating factor-induced phosphoinositide metabolism in differentiated U-937 cells in culture.
PubMed:[Manoalide: a new phospholipase A2 inhibitor of marine origin with potential immunoregulatory effect].
PubMed:Inactivation of phospholipase A2 by manoalide. Localization of the manoalide binding site on bee venom phospholipase A2.
PubMed:Preferential inhibition of 5-lipoxygenase activity by manoalide.
PubMed:Purification and characterization of a lysophospholipase from a macrophage-like cell line P388D1.
PubMed:Solubilization, purification, and characterization of a membrane-bound phospholipase A2 from the P388D1 macrophage-like cell line.
PubMed:Regulation of eicosanoid biosynthesis in vitro and in vivo by the marine natural product manoalide: a potent inactivator of venom phospholipases.
PubMed:Inhibition of platelet aggregation by manoalide: preliminary results.
PubMed:The inhibition of release of endothelium-derived relaxant factor by manoalide, a potent inhibitor of phospholipase A2.
PubMed:Inhibition of phosphoinositide-specific phospholipase C by manoalide.
PubMed:Inactivation of bee venom phospholipase A2 by manoalide. A model based on the reactivity of manoalide with amino acids and peptide sequences.
PubMed:Manoalide, a natural sesterterpenoid that inhibits calcium channels.
PubMed:Differential effects of manoalide on secreted and intracellular phospholipases.
PubMed:The inhibition of phospholipase A2 by manoalide and manoalide analogues.
PubMed:The role of polyphosphoinositides and their breakdown products in A23187-induced release of arachidonic acid from rabbit polymorphonuclear leucocytes.
PubMed:Molecular pharmacology of manoalide. Inactivation of bee venom phospholipase A2.
PubMed:Cobra venom phospholipase A2 inhibition by manoalide. A novel type of phospholipase inhibitor.
PubMed:In vitro inactivation of the neurotoxic action of beta-bungarotoxin by the marine natural product, manoalide.
 
Notes:
phospholipase a2 inhibitor; sesterterpene from marine sponge l. variabilis.
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