EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

cycloartenol
9beta,19-cyclo-24-lanosten-3beta-ol

Supplier Sponsors

CAS Number: 469-38-5Picture of molecule3D/inchi
FDA UNII: YU32VE82N3
Nikkaji Web:J11.335B
Beilstein Number:2224850
XlogP3-AA:9.80 (est)
Molecular Weight:426.72770000
Formula:C30 H50 O
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
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 505.46 °C. @ 760.00 mm Hg (est)
Flash Point: 431.00 °F. TCC ( 221.90 °C. ) (est)
logP (o/w): 10.305 (est)
Soluble in:
 water, 2.31e-005 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.
Cycloartenol 95%
ExtraSynthese
For experimental / research use only.
Cycloarterenol (HPLC) ≥90%
Sigma-Aldrich: Sigma
For experimental / research use only.
Cycloartenol ≥90% (GC)
 
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 cycloartenol usage levels up to:
 not for fragrance use.
 
Recommendation for cycloartenol 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 :92110
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000469385
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92110
Pubchem (sid):135048168
Pherobase:View
 
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
CHEMBL:View
KEGG (GenomeNet):C01902
HMDB (The Human Metabolome Database):HMDB36591
FooDB:FDB015503
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 artemesia monosperma
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 artocarpus integrifolia fruit
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 avocado plant
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 banana fruit
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 breadfruit fruit
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 cantaloupe seed
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 coconut seed oil
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 corn root
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 corn shoot
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 cotton flower
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 cucumber seed
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 dandelion leaf
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 dandelion pollen
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 elder black elder flower
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 evening-primrose seed
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 flax seed
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 grape stem
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 irish moss thallus
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 melon bitter melon seed oil
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 onion bulb
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 papaya seed oil
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 pea black-eyed pea seed
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 pea sprout
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 pepper bell pepper seed
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 poppy opium poppy latex
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 potato tuber
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 rice plant
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 sesame seed
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 sesame seed oil
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 soybean seed
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 soybean sprout
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 sunflower seed
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 tomato seed
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Synonyms:
9beta,19-cyclo-24-lanosten-3beta-ol
 cycloarterenol
(3beta)-9,19-cyclolanost-24-en-3-ol
9,19-cyclolanost-24-en-3-ol, (3beta)-
9,19-cyclolanost-24-en-3-ol, (3beta)-
 

Articles:

PubMed:Preparative mass-spectrometry profiling of bioactive metabolites in Saudi-Arabian propolis fractionated by high-speed countercurrent chromatography and off-line atmospheric pressure chemical ionization mass-spectrometry injection.
PubMed:Cloning and Functional Characterization of Three Branch Point Oxidosqualene Cyclases From Withania somnifera (L.) Dunal.
PubMed:The effect of drought stress on the expression of key genes involved in the biosynthesis of triterpenoid saponins in liquorice (Glycyrrhiza glabra).
PubMed:Sterol partitioning by HMGR and DXR for routing intermediates towards withanolide biosynthesis.
PubMed:Genetic biomarkers of the sterol-biosynthetic pathway in microalgae.
PubMed:Hemp ( Cannabis sativa L.) seed oil: analytical and phytochemical characterization of the unsaponifiable fraction.
PubMed:Triterpenes from Euphorbia hirta and their cytotoxicity.
PubMed:Dynamics of withanolide biosynthesis in relation to temporal expression pattern of metabolic genes in Withania somnifera (L.) Dunal: a comparative study in two morpho-chemovariants.
PubMed:C-24-methylation of 26-fluorocycloartenols by recombinant sterol C-24-methyltransferase from soybean: evidence for channel switching and its phylogenetic implications.
PubMed:Phytochemical profiles of black, red, brown, and white rice from the Camargue region of France.
PubMed:Quantitative analysis of phytosterols in edible oils using APCI liquid chromatography-tandem mass spectrometry.
PubMed:Phytochemical profile of a Japanese black-purple rice.
PubMed:Cycloartenyl trans-ferulate, a component of the bran byproduct of sake-brewing rice, inhibits mammalian DNA polymerase and suppresses inflammation.
PubMed:Isolation of six isoprenylated biflavonoids from the leaves of Garcinia subelliptica.
PubMed:Structure-fragmentation relationship and rapid dereplication of Buxus steroidal alkaloids by electrospray ionization-quadrupole time-of-flight mass spectrometry.
PubMed:Flavonoids bearing an O-arabinofuranosyl-(1-->3)-rhamnoside moiety from Cladocolea micrantha: inhibitory effect on human melanoma cells.
PubMed:Protein engineering of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase into parkeol synthase.
PubMed:[Cloning and bioinformatics analysis of cycloartenol synthase (HcCAS1) gene in Huperzia carinata].
PubMed:Salt-dependent increase in triterpenoids is reversible upon transfer to fresh water in mangrove plants Kandelia candel and Bruguiera gymnorrhiza.
PubMed:[Chemical constituents from the fruits of Areca catechu].
PubMed:Overexpression of 3β-hydroxysteroid dehydrogenases/C-4 decarboxylases causes growth defects possibly due to abnormal auxin transport in Arabidopsis.
PubMed:Evolutionarily conserved Delta(25(27))-olefin ergosterol biosynthesis pathway in the alga Chlamydomonas reinhardtii.
PubMed:Investigation of unsaponifiable matter of plant oils and isolation of eight phytosterols by means of high-speed counter-current chromatography.
PubMed:γ-Oryzanol reduces adhesion molecule expression in vascular endothelial cells via suppression of nuclear factor-κB activation.
PubMed:Three new cycloartenol glycosides from the roots of Cimicifuga simplex.
PubMed:Divergent evolution of oxidosqualene cyclases in plants.
PubMed:Asymmetric somatic hybridization between Bupleurum scorzonerifolium Willd. and Taxus chinensis var. mairei.
PubMed:Three New Cycloartenol Triterpenoid Saponins from the Roots of Cimicifuga simplex Wormsk.
PubMed:Molecular cloning and expression of squalene synthase and 2,3-oxidosqualene cyclase genes in persimmon (Diospyros kaki L.) fruits.
PubMed:Metabolic engineering of soybean affords improved phytosterol seed traits.
PubMed:Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases.
PubMed:Investigation of the potential for triterpene synthesis in rice through genome mining and metabolic engineering.
PubMed:[Anti-HBV constituents from Euphorbia fischeriana].
PubMed:A dynamic role for sterols in embryogenesis of Pisum sativum.
PubMed:Gene identification in black cohosh (Actaea racemosa L.): expressed sequence tag profiling and genetic screening yields candidate genes for production of bioactive secondary metabolites.
PubMed:Gene regulation patterns in triterpene biosynthetic pathway driven by overexpression of squalene synthase and methyl jasmonate elicitation in Bupleurum falcatum.
PubMed:Lipid components of olive oil from Tunisian Cv. Sayali: characterization and authenticity.
PubMed:Commercial peanut (Arachis hypogaea L.) cultivars in the United States: phytosterol composition.
PubMed:Cloning, mechanistic and functional analysis of a fungal sterol C24-methyltransferase implicated in brassicasterol biosynthesis.
PubMed:Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids.
PubMed:Characterization of a potential nutraceutical ingredient: pomegranate (Punica granatum L.) seed oil unsaponifiable fraction.
PubMed:Upregulation of phytosterol and triterpene biosynthesis in Centella asiatica hairy roots overexpressed ginseng farnesyl diphosphate synthase.
PubMed:Selective cholinesterase inhibitory activities of a new monoterpene diglycoside and other constituents from Nelumbo nucifera stamens.
PubMed:Functional characterization of the Chlamydomonas reinhardtii ERG3 ortholog, a gene involved in the biosynthesis of ergosterol.
PubMed:Antioxidant, free radical-scavenging, and NF-kappaB-inhibitory activities of phytosteryl ferulates: structure-activity studies.
PubMed:Steroidal triterpenes: design of substrate-based inhibitors of ergosterol and sitosterol synthesis.
PubMed:Regulation of ginsenoside and phytosterol biosynthesis by RNA interferences of squalene epoxidase gene in Panax ginseng.
PubMed:Cloning, functional expression and phylogenetic analysis of plant sterol 24C-methyltransferases involved in sitosterol biosynthesis.
PubMed:Albinism and cell viability in cycloartenol synthase deficient Arabidopsis.
PubMed:Separation and identification of some common isomeric plant triterpenoids by thin-layer chromatography and high-performance liquid chromatography.
PubMed:Phytosterols accumulation in the seeds of Linum usitatissimum L.
PubMed:Cycloartenyl ferulate, a component of rice bran oil-derived gamma-oryzanol, attenuates mast cell degranulation.
PubMed:New principles from seeds of Nigella sativa.
PubMed:Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis.
PubMed:Cyclobranol: a substrate for C25-methyl sterol side chains and potent mechanism-based inactivator of plant sterol methyltransferase.
PubMed:Development of liquid chromatographic methods for the determination of phytosterols in Standard Reference Materials containing saw palmetto.
PubMed:Allelic mutant series reveal distinct functions for Arabidopsis cycloartenol synthase 1 in cell viability and plastid biogenesis.
PubMed:Squalene cyclase and oxidosqualene cyclase from a fern.
PubMed:Mechanism-based enzyme inactivators of phytosterol biosynthesis.
PubMed:Sterol C24-methyltransferase: mechanistic studies of the C-methylation reaction with 24-fluorocycloartenol.
PubMed:[Analysis of lipid compounds of high-yielded rhizoma pinelliae growing in the west of Hubei province by gas chromatography-mass spectrometry].
PubMed:Biosynthesis of phytosterol esters: identification of a sterol o-acyltransferase in Arabidopsis.
PubMed:Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26.
PubMed:Cloning and functional expression of cycloartenol synthases from mangrove species Rhizophora stylosa Griff. and Kandelia candel (L.) Druce.
PubMed:Structural revision of terpenoids with a (3Z)-2-methyl-3-penten-2-ol moiety by the synthesis of (23E)- and (23Z)-cycloart-23-ene-3beta,25-diols.
PubMed:Formation of triterpenoids throughout Olea europaea fruit ontogeny.
PubMed:Sterol biosynthesis inhibitors: potential for transition state analogs and mechanism-based inactivators targeted at sterol methyltransferase.
PubMed:Diterpenoids and triterpenoids from Euphorbia guyoniana.
PubMed:Enhancement of seed phytosterol levels by expression of an N-terminal truncated Hevea brasiliensis (rubber tree) 3-hydroxy-3-methylglutaryl-CoA reductase.
PubMed:A different function for a member of an ancient and highly conserved cytochrome P450 family: from essential sterols to plant defense.
PubMed:The effect of methyl jasmonate on triterpene and sterol metabolisms of Centella asiatica, Ruscus aculeatus and Galphimia glauca cultured plants.
PubMed:Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides.
PubMed:Lanosterol synthase in dicotyledonous plants.
PubMed:Plant lanosterol synthase: divergence of the sterol and triterpene biosynthetic pathways in eukaryotes.
PubMed:Lanosterol biosynthesis in plants.
PubMed:Cloning and characterization of a lupeol synthase involved in the synthesis of epicuticular wax crystals on stem and hypocotyl surfaces of Ricinus communis.
PubMed:Mechanism involved in the spasmolytic effect of a mixture of two triterpenes, cycloartenol and cycloeucalenol, isolated from Herissanthia tiubae in the guinea-pig ileum.
PubMed:Probing the sterol binding site of soybean sterol methyltransferase by site-directed mutagenesis: functional analysis of conserved aromatic amino acids in Region 1.
PubMed:Enzyme redesign: two mutations cooperate to convert cycloartenol synthase into an accurate lanosterol synthase.
PubMed:Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship.
PubMed:[Study on chemical constituents in rhizome of Pinellia ternata].
PubMed:Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran.
PubMed:[Studies on chemical constituents of Ervatamia hainanensis].
PubMed:New constituents from Crinum latifolium with inhibitory effects against tube-like formation of human umbilical venous endothelial cells.
PubMed:New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta.
PubMed:Oxidosqualene cyclase second-sphere residues profoundly influence the product profile.
PubMed:Evaluation of the antioedematogenic, free radical scavenging and antimicrobial activities of aerial parts of Tillandsiastreptocarpa Baker-Bromeliaceae.
PubMed:New aspects on lanosterol 14alpha-demethylase and cytochrome P450 evolution: lanosterol/cycloartenol diversification and lateral transfer.
PubMed:Enhanced triterpene and phytosterol biosynthesis in Panax ginseng overexpressing squalene synthase gene.
PubMed:Characterization of carrot root oil arising from supercritical fluid carbon dioxide extraction.
PubMed:Differential expression of three oxidosqualene cyclase mRNAs in Glycyrrhiza glabra.
PubMed:New cycloartenol esters from Ixora coccinea.
PubMed:A gene cluster for secondary metabolism in oat: implications for the evolution of metabolic diversity in plants.
PubMed:Mechanism-based active site modification of the soybean sterol methyltransferase by 26,27-dehydrocycloartenol.
PubMed:Plant sterol biosynthesis: identification of two distinct families of sterol 4alpha-methyl oxidases.
PubMed:Sterol methyltransferase2: purification, properties, and inhibition.
PubMed:Evaluation of the antiviral and antimicrobial activities of triterpenes isolated from Euphorbia segetalis.
PubMed:Co-expression of N-terminal truncated 3-hydroxy-3-methylglutaryl CoA reductase and C24-sterol methyltransferase type 1 in transgenic tobacco enhances carbon flux towards end-product sterols.
PubMed:Synthesis and structure-activity studies of novel orally active non-terpenoic 2,3-oxidosqualene cyclase inhibitors.
PubMed:Biosynthesis of phytosterols. Kinetic mechanism for the enzymatic C-methylation of sterols.
PubMed:Inhibition of benzoyl peroxide and ultraviolet-B radiation induced oxidative stress and tumor promotion markers by cycloartenol in murine skin.
PubMed:[Studies on chemical constituents of Fragaria ananassa Duch].
PubMed:[Studies on chemical constituents of two plants from Costus].
PubMed:Oxidosqualene cyclases from cell suspension cultures of Betula platyphylla var. japonica: molecular evolution of oxidosqualene cyclases in higher plants.
PubMed:Up-regulation of soyasaponin biosynthesis by methyl jasmonate in cultured cells of Glycyrrhiza glabra.
PubMed:Phylogeny of choanozoa, apusozoa, and other protozoa and early eukaryote megaevolution.
PubMed:Mechanistic insights into oxidosqualene cyclizations through homology modeling.
PubMed:Subcellular localization of oxidosqualene cyclases from Arabidopsis thaliana, Trypanosoma cruzi, and Pneumocystis carinii expressed in yeast.
PubMed:Co-ordinate regulation of sterol biosynthesis enzyme activity during accumulation of sterols in developing rape and tobacco seed.
PubMed:Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca.
PubMed:A genomics approach to the early stages of triterpene saponin biosynthesis in Medicago truncatula.
PubMed:Brassinosteroids. Plant counterparts to animal steroid hormones?
PubMed:Directed evolution experiments reveal mutations at cycloartenol synthase residue His477 that dramatically alter catalysis.
PubMed:Antitubercular constituents from the hexane fraction of Morinda citrifolia Linn. (Rubiaceae).
PubMed:Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase.
PubMed:Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed.
PubMed:Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols.
PubMed:Conversion of a plant oxidosqualene-cycloartenol synthase to an oxidosqualene-lanosterol cyclase by random mutagenesis.
PubMed:The Pneumocystis carinii drug target S-adenosyl-L-methionine:sterol C-24 methyl transferase has a unique substrate preference.
PubMed:Molecular cloning and functional expression of cDNAs encoding oxidosqualene cyclases from Costus speciosus.
PubMed:Directed evolution to generate cycloartenol synthase mutants that produce lanosterol.
PubMed:Two novel long-chain alkanoic acid esters of lupeol from alecrim-propolis.
PubMed:Polyene substrates with unusual methylation patterns to probe the active sites of three catalytic antibodies.
PubMed:Influence of the parasite Viscum cruciatum Sieber on the chemical constituents of Crataegus monogyna Jacq.
PubMed:Molecular cloning and characterization of isomultiflorenol synthase, a new triterpene synthase from Luffa cylindrica, involved in biosynthesis of bryonolic acid.
PubMed:An immunosuppressive tryptophan-derived alkaloid from Lepidagathis cristata.
PubMed:Soybean sterol composition and utilization by Phytophthora sojae.
PubMed:Cloning and characterization of a cDNA encoding beta-amyrin synthase involved in glycyrrhizin and soyasaponin biosyntheses in licorice.
PubMed:Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.
PubMed:Molecular cloning and expression in yeast of 2,3-oxidosqualene-triterpenoid cyclases from Arabidopsis thaliana.
PubMed:Investigation of avenacin-deficient mutants of Avena strigosa.
PubMed:Oxidosqualene Cyclase Residues that Promote Formation of Cycloartenol, Lanosterol, and Parkeol We are grateful to Bridget M. Joubert for advice regarding mutagenesis. We thank Elizabeth A. Hart for an authentic parkeol standard, and for chromatographic and spectroscopic information. This research was funded by the National Institutes of Health (grant no. AI 41598) and the Robert A. Welch Foundation (grant no. C-1323). M.M.M. was an American Society of Pharmacognosy Undergraduate Fellow. M.J.R.S. was a Robert A. Welch Fellow and was supported by an NIH Biotechnology Training Grant (grant no. T32 GM08362).
PubMed:Steric bulk at cycloartenol synthase position 481 influences cyclization and deprotonation.
PubMed:Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects.
PubMed:Sterol C-methyl transferase from Prototheca wickerhamii mechanism, sterol specificity and inhibition.
PubMed:Biosynthesis of avenacins and phytosterols in roots of Avena sativa cv. Image.
PubMed:Sterol methyltransferase 1 controls the level of cholesterol in plants.
PubMed:Functional cloning of an Arabidopsis thaliana cDNA encoding cycloeucalenol cycloisomerase.
PubMed:Plant sterol-C24-methyl transferases: different profiles of tobacco transformed with SMT1 or SMT2.
PubMed:Cloning and characterization of the Dictyostelium discoideum cycloartenol synthase cDNA.
PubMed:Molecular cloning and characterization of a cDNA for Glycyrrhiza glabra cycloartenol synthase.
PubMed:Nonpolar components of the latex of Euphorbia peplus.
PubMed:New triterpenoid sulfates from the red alga Tricleocarpa fragilis.
PubMed:Natural products with hypoglycemic, hypotensive, hypocholesterolemic, antiatherosclerotic and antithrombotic activities.
PubMed:Two branches of the lupeol synthase gene in the molecular evolution of plant oxidosqualene cyclases.
PubMed:Characterization and catalytic properties of the sterol 14alpha-demethylase from Mycobacterium tuberculosis.
PubMed:Enzymology of phytosterol transformations.
PubMed:4,4,14 alpha-trimethyl 9 beta,19-cyclo-5 alpha-26-homocholesta-24,26-dien-3 beta-ol: a potent mechanism-based inactivator of delta 24(25)- to delta 25(27)-sterol methyl transferase.
PubMed:Cloning and characterization of the Arabidopsis thaliana lupeol synthase gene.
PubMed:Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stage carcinogenesis in mouse skin.
PubMed:Beta-amyrin synthase--cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants.
PubMed:Two families of sterol methyltransferases are involved in the first and the second methylation steps of plant sterol biosynthesis.
PubMed:Molecular cloning of pea cDNA encoding cycloartenol synthase and its functional expression in yeast.
PubMed:Identification of cDNAs encoding sterol methyl-transferases involved in the second methylation step of plant sterol biosynthesis.
PubMed:Substrate-based inhibitors of the (S)-adenosyl-L-methionine:delta24(25)- to delta24(28)-sterol methyl transferase from Saccharomyces cerevisiae.
PubMed:The effects of a triterpene fraction isolated from Crataegus monogyna Jacq. on different acute inflammation models in rats and mice. Leucocyte migration and phospholipase A2 inhibition.
PubMed:Triterpene alcohols from the flowers of compositae and their anti-inflammatory effects.
PubMed:Cytotoxic triterpenoids from the leaves of Euphorbia pulcherrima.
PubMed:Identification and characterization of an S-adenosyl-L-methionine: delta 24-sterol-C-methyltransferase cDNA from soybean.
PubMed:Antibacterial hydroperoxysterols from Xanthosoma robustum.
PubMed:Is the Reaction Catalyzed by 3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase a Rate-Limiting Step for Isoprenoid Biosynthesis in Plants?
PubMed:Novel sterol transformations promoted by Saccharomyces cerevisiae strain GL7: evidence for 9 beta, 19-cyclopropyl to 9(11)-isomerization and for 14-demethylation to 8(14)-sterols.
PubMed:Expression of the Hevea brasiliensis (H.B.K.) Mull. Arg. 3-Hydroxy-3-Methylglutaryl-Coenzyme A Reductase 1 in Tobacco Results in Sterol Overproduction.
PubMed:A new monodesmosidic triterpenoid saponin from the seeds of Vigna unguiculata subsp. unguiculata.
PubMed:Growth of Cucurbita maxima L. plants in the presence of the cycloartenol synthase inhibitor U18666A.
PubMed:2,3-Oxidosqualene cyclase: from azasqualenes to new site-directed inhibitors.
PubMed:Zymomonas mobilis squalene-hopene cyclase gene (shc): cloning, DNA sequence analysis, and expression in Escherichia coli.
PubMed:Comparative studies of metabolism of 4-desmethyl, 4-monomethyl and 4,4-dimethyl sterols in Manduca sexta.
PubMed:Isolation and characterization of the gene encoding 2,3-oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae.
PubMed:Molecular cloning, characterization, and overexpression of ERG7, the Saccharomyces cerevisiae gene encoding lanosterol synthase.
PubMed:New cycloartanol sulfates from the alga Tydemania expeditionis: inhibitors of the protein tyrosine kinase pp60v-src.
PubMed:Isolation of an Arabidopsis thaliana gene encoding cycloartenol synthase by functional expression in a yeast mutant lacking lanosterol synthase by the use of a chromatographic screen.
PubMed:Effect of the rice bran-derived phytosterol cycloartenol ferulic acid ester on the central nervous system.
PubMed:Plant sterol biosynthesis. Identification and characterization of two distinct microsomal oxidative enzymatic systems involved in sterol C4-demethylation.
PubMed:The structural requirements of sterols for membrane function in Saccharomyces cerevisiae.
PubMed:Inhibition of 2,3-oxidosqualene cyclases.
PubMed:Affinity labeling of vertebrate oxidosqualene cyclases with a tritiated suicide substrate.
PubMed:Nutritional and biochemical aspects of the hypolipidemic action of rice bran oil: a review.
PubMed:Differential effects of plant sterols on water permeability and on acyl chain ordering of soybean phosphatidylcholine bilayers.
PubMed:Structural requirements for transformation of substrates by the (S)-adenosyl-L-methionine:delta 24(25)-sterol methyl transferase.
PubMed:Regulation of sterol biosynthesis in sunflower by 24(R,S),25-epiminolanosterol, a novel C-24 methyl transferase inhibitor.
PubMed:Application of modern NMR techniques in the structure determination of microbial transformation products from sterols.
PubMed:Biosynthetic studies of marine lipids. 35. The demonstration of de novo sterol biosynthesis in sponges using radiolabeled isoprenoid precursors.
PubMed:Sterol phylogenesis and algal evolution.
PubMed:Soybean phosphatidylcholine vesicles containing plant sterols: a fluorescence anisotropy study.
PubMed:Triterpenoid biosynthesis in tissue cultures of Glycyrrhiza glabra var. glandulifera.
PubMed:Concerning the role of 24,25-dihydrolanosterol and lanostanol in sterol biosynthesis by cultured cells.
PubMed:Polyterpenoids as cholesterol and tetrahymanol surrogates in the ciliate Tetrahymena pyriformis.
PubMed:New Cycloartenol Derivatives from Aglaia roxburghiana1.
PubMed:Effects of gamma-oryzanol and cycloartenol ferulic acid ester on cholesterol diet induced hyperlipidemia in rats.
PubMed:Sterol conjugates of two phenotypically different calli of Beta vulgaris.
PubMed:Sterol biosynthesis via cycloartenol and other biochemical features related to photosynthetic phyla in the amoeba Naegleria lovaniensis and Naegleria gruberi.
PubMed:The action of the systemic fungicides tridemorph and fenpropimorph on sterol biosynthesis by the soil amoeba Acanthamoeba polyphaga.
PubMed:Microbial lipids betrayed by their fossils.
PubMed:Constituents of Shashen (Adenophora axilliflora).
PubMed:N-[(1,5,9)-trimethyl-decyl]-4 alpha,10-dimethyl-8-aza-trans-decal-3 beta-ol a novel potent inhibitor of 2,3-oxidosqualene cycloartenol and lanosterol cyclases.
PubMed:The squalene-2,3-epoxide cyclase as a model for the development of new drugs.
PubMed:Sterol biosynthesis de nova via cycloartenol by the soil amoeba Acanthamoeba polyphaga.
PubMed:Effects of cycloartenol on absorption and serum levels of cholesterol in rats.
PubMed:Sterol Composition of the Corn Cyst Nematode, Heterodera zeae, and Corn Roots.
PubMed:Inhibition of S-adenosyl-L-methionine sterol-C-24-methyltransferase by analogues of a carbocationic ion high-energy intermediate. Structure activity relationships for C-25 heteroatoms (N, As, S) substituted triterpenoid derivatives.
PubMed:Inhibition of 2,3-oxidosqualene: beta-amyrin-cyclase, S-adenosyl-L-methionine: cycloartenol C-24-methyltransferase and cycloeucalenol: obtusifoliol isomerase by rationally designed molecules containing a tertiary amine function.
PubMed:Hypocholesterolemic effect of triterpene alcohols with soysterol on plasma cholesterol in rats.
PubMed:[Triterpenes and steroids in callus cultures of Solanum dulcamara].
PubMed:[Triterpenes and steroids in seeds of Solanum dulcamara].
PubMed:Cycloartenol-derived sterol biosynthesis in the Peronosporales.
PubMed:Annual Variation in Sterol Levels in Leaves of Taraxacum officinale Weber.
PubMed:Sterols of Delphinium ajacis; production and metabolic relationships in whole plants and callus tissue.
PubMed:Effects of cycloartenol and lanosterol on artificial and natural membranes.
PubMed:25-Azacycloartanol, a potent inhibitor of S-adenosyl-L-methionine-sterol-C-24 and C-28 methyltransferases in higher plant cells.
PubMed:Comparative responses of the yeast mutant strain GL7 to lanosterol, cycloartenol, and cyclolaudenol.
PubMed:Sterol requirement of Mycoplasma capricolum.
PubMed:Occurrence of lanosterol and lanostenol in seeds of red pepper (Capsicum annuum).
PubMed:Analysis of methylsterol fractions from twenty vegetable oils.
PubMed:[Studies on the constituents of Lyonia ovalifolia Drude var. elliptica Hand.-Mazz. XX. Structure of triterpenoid glucoside, lyofolic acid. (4). Correlation of protolyofoligenic acid with cycloartenol (author's transl)].
PubMed:2,3-Oxidosqualene cyclase and cycloartenol-s-adenosylmethionine methyltransferase activities in vivo in the cotyledon and axis tissues of germinating pea seeds.
PubMed:Letter: On the role of cycloartenol in the formation of phytosterols. Biosynthesis of (19-2H)sitosterol in deuterium oxide germinated peas.
PubMed:Uptake of [2-(14)C] mevalonic acid by lipid and glycoside sterols.
PubMed:Inhibition of Sterol Biosynthesis in Chlorella sorokiniana by Triparanol.
PubMed:S-adenosyl-L-methionine-cycloartenol methyltransferase activity in cell-free systems from Trebouxia sp. and Scenedesmus obliquus.
PubMed:Properties of a 2,3-oxidosqualene-cycloartenol cyclase from Ochromonas malhamensis.
PubMed:Sterol and triterpene synthesis in the developing and germinating pea seed.
PubMed:Concerning the role of lanosterol and cycloartenol in steroid biosynthesis.
PubMed:[Steroidal alkaloids 98. Chemical constitution of the seeds of Holarrhena floribunda (G. Don) Dur. and Schiz: cycloartenol, nor-31 lanosterol, dehydro-24 lophenol, desmosterol and steroidal alkaloids: conessine, isoconessimine, conamine and conarrhimine].
PubMed:[Synthesis of labeled tetracyclic triterpenes. I. Lanosterol, cycloartenol, parkeol and 31-norcycloartenol(25-14C) or (26,27-D). II. Lanosterol and cycloartenol (2-T)].
PubMed:Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.
PubMed:2,3-oxidosqualene cycloartenol cyclase from Ochromonas malhamensis.
PubMed:[Anerobic cyclization of squalen-2,3-epoxide to cycloartenol in Nicotiana tabacum L. tissue cultures].
PubMed:The conversion of lanosterol, cycloartenol and 24-methylenecycloartanol into poriferasterol by Ochromonas malhamensis.
PubMed:The conversion of [14C]cycloartenol and [14C)lanosterol into phytosterols by cultures of Nicotiana tabacum.
PubMed:Studies in phytosterol biosynthesis. Mechanism of biosynthesis of cycloartenol.
PubMed:Cyclization of 2,3-oxidosqualene to cycloartenol in a cell-free system from higher plants.
PubMed:The biosynthesis of sterols in higher plants.
 
Notes:
found in chlorophyll-containing plants. Constit. of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol.
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