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
Identification
| Name | glaucarubin |
| CAS Number | 1448-23-3 |
| FDA UNII | EH6H7VS52J |
| Molecular Formula | C25 H36 O10 |
| Molecular Weight | 496.55392000 |
Regulatory
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) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-mouse LD50 1200 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 28 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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.