glaucarubin
(1beta,2alpha,11beta,12alpha,15beta(S))-11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy) picras-3-en-16-one
 
Notes:
(1 beta,2 alpha,11 beta,12 alpha,15 beta(s))-11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. a quassinoid (simaroubolide) from simaruba glauca, a tropical shrub. it has been used as an antiamebic agent and is found to be cytotoxic. it may be of use in cancer chemotherapy. Isol. from Simarouba glauca (aceituno)
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CAS Number: 1448-23-3Picture of molecule3D/inchi
Other: 1392-07-0
FDA UNII: EH6H7VS52J
XlogP3-AA: -0.20 (est)
Molecular Weight: 496.55392000
Formula: C25 H36 O10
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 690.90 °C. @ 760.00 mm Hg (est)
Flash Point: 448.00 °F. TCC ( 231.20 °C. ) (est)
logP (o/w): -0.436 (est)
Soluble in:
 water, 1800 mg/L @ 25 °C (exp)
 water, 6270 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
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:
oral-mouse LD50  1200 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 114, Pg. 307, 1958.

oral-rat LD50  800 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.

Dermal Toxicity:
subcutaneous-mouse LD50 28 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for glaucarubin usage levels up to:
 not for fragrance use.
 
Recommendation for glaucarubin flavor usage levels up to:
 not for flavor use.
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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 : 56840806
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0001448233
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 56840806
Pubchem (sid): 134979999
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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
KEGG (GenomeNet): C08760
HMDB (The Human Metabolome Database): HMDB35626
FooDB: FDB014332
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 simarouba glauca
Search Trop  Picture
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Synonyms:
(1beta,2alpha,11beta,12alpha,15beta(S))-11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy) picras-3-en-16-one
 glarubin
 glaucarubina
 glaumeba
alpha-kirondrin
 MK-53
 simarubaceae
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Articles:
PubMed: Glaucarubinone and gemcitabine synergistically reduce pancreatic cancer growth via down-regulation of P21-activated kinases.
PubMed: The phytochemical glaucarubinone promotes mitochondrial metabolism, reduces body fat, and extends lifespan of Caenorhabditis elegans.
PubMed: Cytotoxic activity of Brazilian Cerrado plants used in traditional medicine against cancer cell lines.
PubMed: Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition.
PubMed: Antiviral activity of simalikalactone D, a quassinoid from Quassia africana.
PubMed: Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture.
PubMed: Aphrodisiac evaluation in non-copulator male rats after chronic administration of Eurycoma longifolia Jack.
PubMed: Insect antifeedant and growth regulating activities of quassinoids from Samadera indica.
PubMed: Total synthesis of (+)-quassin.
PubMed: Nematocidal activity of quassinoids against a species of Diplogastridae.
PubMed: Studies on the anxiolytic activity of Eurycoma longifolia Jack roots in mice.
PubMed: Quassinoids from the twigs and thorns of Castela polyandra.
PubMed: Anti-malarial activities of acylated bruceolide derivatives.
PubMed: In vitro anti-trichomonic activity of Castela texana.
PubMed: Anticancer activity of glaucarubinone analogues.
PubMed: Mode of action of the anticancer quassinoids--inhibition of the plasma membrane NADH oxidase.
PubMed: Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and their structure-activity relationships.
PubMed: Effect of the quassinoids glaucarubolone and simalikalactone D on growth of cells permanently infected with feline and human immunodeficiency viruses and on viral infections.
PubMed: Anti-tuberculosis activity of quassinoids.
PubMed: Synthesis of cytotoxic fluorinated quassinoids.
PubMed: [Weitz' aminium salt initiated electron transfer reactions and application to the synthesis of natural products].
PubMed: Bruceine B, a potent inhibitor of leukocyte-endothelial cell adhesion.
PubMed: Inhibitory effects of quassinoid derivatives on Epstein-Barr virus early antigen activation.
PubMed: Quassinoids as inhibitors of Epstein-Barr virus early antigen activation.
PubMed: Antifertility activity of Quassia amara in male rats - in vivo study.
PubMed: Indonesian medicinal plants. XVII. Characterization of quassinoids from the stems of Quassia indica.
PubMed: Two new quassinoids, ailantinols A and B, and related compounds from Ailanthus altissima.
PubMed: Effect of 7-day daily replacement of culture medium containing Eurycoma longifolia Jack constituents on the Malaysian Plasmodium falciparum isolates.
PubMed: Bruceanols G and H cytotoxic quassinoids from Brucea antidysenterica.
PubMed: Bruceosides D, E, and F, three new cytotoxic quassinoid glucosides from Brucea javanica.
PubMed: Antifertility activity of Quassia amara: quassin inhibits the steroidogenesis in rat Leydig cells in vitro.
PubMed: In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant Plasmodium falciparum isolates.
PubMed: In vitro cytotoxicity of chaparrin from Castela texana.
PubMed: Effects of chaparrin, nordihydroguaiaretic acid and their structural analogues on Entamoeba histolytica cultures.
PubMed: Antimalarial activity of cedronin.
PubMed: Bruceanols D, E, and F three new cytotoxic quassinoids from Brucea antidysenterica.
PubMed: A new antimalarial quassinoid from Simaba guianensis.
PubMed: Quassinoids exhibit greater selectivity against Plasmodium falciparum than against Entamoeba histolytica, Giardia intestinalis or Toxoplasma gondii in vitro.
PubMed: Effect of quassin on the metabolism of catecholamines in different life cycle stages of Culex quinquefasciatus.
PubMed: Cytotoxic quassinoids from Cedronia granatensis.
PubMed: Mode of action of the antitumor compound girodazole (RP 49532A, NSC 627434).
PubMed: Antitumor agents, 127. Bruceoside C, a new cytotoxic quassinoid glucoside, and related compounds from Brucea javanica.
PubMed: Larvicidal efficacy of Quassin against Culex quinquefasciatus.
PubMed: Picrasinoside H, a new quassinoid glucoside, and related compounds from the stem wood of Picrasma ailanthoides.
PubMed: In vitro cytotoxicity of a series of quassinoids from Brucea javanica fruits against KB cells.
PubMed: Antitumor agents, 118. The isolation and characterization of bruceanic acid A, its methyl ester, and the new bruceanic acids B, C, and D, from Brucea antidysenterica.
PubMed: [Studies on pharmacologically active principles from Indonesian crude drugs. III. Toxic components from Brucea javanica (L.) Merr].
PubMed: [Studies on the chemical constituents of Brucea javanica (L.) Merr].
PubMed: Studies on the constituents of Indonesian Picrasma javanica. III. Structures of new quassinoids, javanicins A, C and D.
PubMed: Antitumor agents, 104. Isolation of yadanziosides M and P from Brucea antidysenterica and identification of bruceantinoside B as a mixture of yadanzioside P and bruceantinoside C.
PubMed: Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids.
PubMed: 1H- and 13C-NMR spectroscopic studies of selected quassinoids.
PubMed: Antitumor activity of novel ailanthone derivatives in vitro and in vivo.
PubMed: Antitumor agents, 93. Bruceanol C, a new cytotoxic quassinoid from Brucea antidysenterica.
PubMed: Metabolism of plant-derived anticancer agents.
PubMed: Antitumor agents, 90. Bruceantinoside C, a new cytotoxic quassinoid glycoside from Brucea antidysenterica.
PubMed: Antimalarial agents, 4. Synthesis of a brusatol analog and biological activity of brusatol-related compounds.
PubMed: Acute insecticidal activity of quassin and its congeners against the American cockroach.
PubMed: Plants as sources of antimalarial drugs, Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo.
PubMed: [Therapeutic trials of experimental murine malaria with the quassinoid, glaucarubinone].
PubMed: Yadanzioside P, a new antileukemic quassinoid glycoside from Brucea javanica (L.) Merr with the 3-O-(beta-D-glucopyranosyl)bruceantin structure.
PubMed: Plants as sources of antimalarial drugs: in vitro antimalarial activities of some quassinoids.
PubMed: Two new quassinoids from Simaba multiflora fruits.
PubMed: [Castela texana: screening for its anti-amoebic activity].
PubMed: Antitumor agents, 74. Bruceanol-A and -B, two new antileukemic quassinoids from Brucea antidysenterica.
PubMed: Growth inhibitory, insecticidal and antifeedant effects of some antileukemic and cytotoxic quassinoids on two species of agricultural pests.
PubMed: Quassinoid bitter principles. II.
PubMed: Evaluation of bleomycin, chlorozotocin, MGBG, and bruceantin in patients with advanced soft tissue sarcoma, bone sarcoma, or mesothelioma.
PubMed: Antitumor agents, 65. Brusatol and cleomiscosin-A, antileukemic principles from Brucea javanica.
PubMed: Reversibility of protein synthesis inhibition by quassinoid antineoplastic agents in a rabbit reticulocyte system.
PubMed: An enzyme-linked immunosorbent assay for quassin and closely related metabolites.
PubMed: Anti-inflammatory agents III: Structure-activity relationships of brusatol and related quassinoids.
PubMed: Antimalarial activity of bruceantin in vitro.
PubMed: Antitumor agents LIX: effects of quassinoids on protein synthesis of a number of murine tumors and normal cells.
PubMed: Structure-activity relationships for binding and inactivation of rabbit reticulocyte ribosomes by quassinoid antineoplastic agents.
PubMed: A Phase II study of Bruceantin (NSC-165, 563) in advanced malignant melanoma.
PubMed: Phase II trial of bruceantin in metastatic breast carcinoma.
PubMed: Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica.
PubMed: Antitumor agents XLVIII: Structure-activity relationships of quassinoids as in vitro protein synthesis inhibitors of P-388 lymphocytic leukemia tumor cell metabolism.
PubMed: Antitumor agents XLVI: In vitro effects of esters of brusatol, bisbrusatol, and related compounds on nucleic acid and protein synthesis of P-388 lymphocytic leukemia cells.
PubMed: Antitumor agents XLV: Bisbrusatolyl and brusatolyl esters and related compounds as novel potent antileukemic agents.
PubMed: Antitumor agents XLVII: The effects of bisbrusatolyl malonate on P-388 lymphocytic leukemia cell metabolism.
PubMed: Clinical pharmacology of bruceantin by radioimmunoassay.
PubMed: [Mode of action of new antitumor compounds].
PubMed: In vitro activity of certain quassinoid anti-tumor agents against Entamoeba histolytica.
PubMed: Antitumor agents XLII: Comparison of antileukemic activity of helenalin, brusatol, and bruceantin and their esters on different strains of P-388 lymphocytic leukemic cells.
PubMed: Phase I study on bruceantin administered on a weekly schedule.
PubMed: Mechanism of eukaryotic protein synthesis inhibition by brusatol.
PubMed: Antitumor agents. 39. Bruceantinoside-A and -B, novel antileukemic quassinoid glucosides from Brucea antidysenterica.
PubMed: Soularubinone, a new antileukemic quassionoid from Soulamea tomentosa.
PubMed: Antimalarial activity of quassinoids against chloroquine-resistant Plasmodium falciparum in vitro.
PubMed: Bruceolides from Filjian Brucea javanica.
PubMed: [Antiamebic properties of some derivatives of ailantone and quassin].
PubMed: [The chemical constituents of the Chinese drug "Yadanzi." I. Isolation and identification of daucosterol, brucein D and brucein E (author's transl)].
PubMed: Radioimmunoassay for the detection and quantitation of bruceantin.
PubMed: The antineoplastic quassinoids of Simaba cuspidata spruce and Ailanthus grandis Prain.
PubMed: Bruceantin, an inhibitor of the initiation of protein synthesis in eukaryotes [proceedings].
PubMed: Structural requirements of quassinoids for the inhibition of cell transformation.
PubMed: Cytotoxic bruceolides from Brucea javanica [proceedings].
PubMed: Phase I trial of bruceantin.
PubMed: Initial clinical studies with bruceantin.
PubMed: Antitumor agents. XXXIV: Mechanism of action of bruceoside A and brusatol on nucleic acid metabolism of P-388 lymphocytic leukemia cells.
PubMed: Antitumor agents. XXXV: Effects of brusatol, bruceoside A, and bruceantin on P-388 lymphocytic leukemia cell respiration.
PubMed: Disposition and metabolism of bruceantin in the mouse.
PubMed: Potential anticancer agents IX. Isolation of a new simaroubolide, 6alpha-tigloyloxychaparrinone, from Ailanthus integrifolia ssp. calycina (Simaroubaceae).
PubMed: Plant antitumor agents. XVI. 6alpha-Senecioyloxy-chaparrinone, a new antileukemic quassinoid from Simaba multiflora.
PubMed: New natural products of interest under development at the National Cancer Institute.
PubMed: Potential anticancer agents vi. Constituents of Ailanthus excelsa (Simaroubaceae).
PubMed: Antitumor plants. IV. Constituents of Simarouba versicolor.
PubMed: Structural requirements for biological activity among antileukemic glaucarubolone ester quassinoids.
PubMed: Treatment of amebic abscess of the liver.
PubMed: Effects of amebicides on growth of Acanthamoeba sp.
PubMed: CRYSTAL AND MOLECULAR STRUCTURE OF GLAUCARUBIN.
PubMed: [The treatment of intestinal amebiasis with glaucarubin. Apropos of 173 case].
PubMed: [Treatment of autochthonous chronic non-dy-senteric amebiasis with glaucarubin].
PubMed: [The treatment of intestinal amebiasis by glaucarubin].
PubMed: Chemotherapeutic and pharmacological studies on glaucarubin, a specific amebacide.
PubMed: The use of glaucarubin (a crystalline glycoside isolated from Simarouba glauca) in the treatment of human colonic amebiasis.
PubMed: Symposium on the treatment of human amoebiasis. II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics.
PubMed: Clinical trial of glaucarubin in treatment of amebiasis.
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