Glaucarubin (BioDeep_00000006959)

 

Secondary id: BioDeep_00001869667

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


4,5,16,17-Tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-8-yl 2-hydroxy-2-methylbutanoic acid

化学式: C25H36O10 (496.2308)
中文名称: 格劳卡昔
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 72.52%

分子结构信息

SMILES: CCC(C)(C(=O)OC1C2C(C(C3(C4C2(CO3)C(CC5C4(C(C(C=C5C)O)O)C)OC1=O)O)O)C)O
InChI: InChI=1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3/t11-,12+,13+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1

描述信息

Glaucarubin is found in fats and oils. Glaucarubin is isolated from Simarouba glauca (aceituno
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
Isolated from Simarouba glauca (aceituno). Glaucarubin is found in fats and oils.
D000970 - Antineoplastic Agents

同义名列表

10 个代谢物同义名

4,5,16,17-Tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-8-yl 2-hydroxy-2-methylbutanoic acid; 4,5,16,17-tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-8-yl 2-hydroxy-2-methylbutanoate; Picras-3-en-16-one,11,20-epoxy-1,2,11,12-tetrahydroxy-15-[(2S)-2-hydroxy-2-methyl-1-oxobutoxy]-,(1b,2a,11b,12a,15b)-; alpha-Kirondrin; Glaucarubina; Simarubaceae; Glaucarubin; b-Kirondrin; Kirondrin; Glaucarubin



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

37 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Simone A M Badal, Malyn M Asuncion Valenzuela, Dain Zylstra, George Huang, Pallavi Vendantam, Sheena Francis, Ashley Quitugua, Louisa H Amis, Willie Davis, Tzuen-Rong J Tzeng, Helen Jacobs, David J Gangemi, Greg Raner, Leah Rowland, Jonathan Wooten, Petreena Campbell, Eileen Brantley, Rupika Delgoda. Glaucarubulone glucoside from Castela macrophylla suppresses MCF-7 breast cancer cell growth and attenuates benzo[a]pyrene-mediated CYP1A gene induction. Journal of applied toxicology : JAT. 2017 07; 37(7):873-883. doi: 10.1002/jat.3436. [PMID: 28138972]
  • K Zarse, A Bossecker, L Müller-Kuhrt, K Siems, M A Hernandez, W G Berendsohn, M Birringer, M Ristow. The phytochemical glaucarubinone promotes mitochondrial metabolism, reduces body fat, and extends lifespan of Caenorhabditis elegans. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2011 Apr; 43(4):241-3. doi: 10.1055/s-0030-1270524. [PMID: 21264793]
  • Mariana Laundry de Mesquita, José Elias de Paula, Cláudia Pessoa, Manoel Odorico de Moraes, Letícia Veras Costa-Lotufo, Raphael Grougnet, Sylvie Michel, François Tillequin, Laila Salmen Espindola. Cytotoxic activity of Brazilian Cerrado plants used in traditional medicine against cancer cell lines. Journal of ethnopharmacology. 2009 Jun; 123(3):439-45. doi: 10.1016/j.jep.2009.03.018. [PMID: 19501276]
  • John A Beutler, Moon-Il Kang, Francis Robert, Jason A Clement, Jerry Pelletier, Nancy H Colburn, Tawnya C McKee, Ekaterina Goncharova, James B McMahon, Curtis J Henrich. Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition. Journal of natural products. 2009 Mar; 72(3):503-6. doi: 10.1021/np800732n. [PMID: 19199792]
  • Sandra Apers, Kanyanga Cimanga, Dirk Vanden Berghe, Els Van Meenen, Albert Otshudi Longanga, André Foriers, Arnold Vlietinck, Luc Pieters. Antiviral activity of simalikalactone D, a quassinoid from Quassia africana. Planta medica. 2002 Jan; 68(1):20-4. doi: 10.1055/s-2002-19870. [PMID: 11842321]
  • H H Ang, T H Ngai. Aphrodisiac evaluation in non-copulator male rats after chronic administration of Eurycoma longifolia Jack. Fundamental & clinical pharmacology. 2001 Aug; 15(4):265-8. doi: 10.1046/j.1472-8206.2001.00038.x. [PMID: 11564133]
  • T R Govindachari, G N Krishna Kumari, G Gopalakrishnan, G Suresh, S D Wesley, T Sreelatha. Insect antifeedant and growth regulating activities of quassinoids from Samadera indica. Fitoterapia. 2001 Jun; 72(5):568-71. doi: 10.1016/s0367-326x(00)00342-7. [PMID: 11429258]
  • H H Ang, H S Cheang. Studies on the anxiolytic activity of Eurycoma longifolia Jack roots in mice. Japanese journal of pharmacology. 1999 Apr; 79(4):497-500. doi: 10.1254/jjp.79.497. [PMID: 10361892]
  • G François, C Diakanamwa, G Timperman, G Bringmann, T Steenackers, G Atassi, M Van Looveren, J Holenz, J P Tassin, L A Assi, R Vanhaelen-Fastre, M Vanhaelen. Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and their structure-activity relationships. International journal for parasitology. 1998 Apr; 28(4):635-40. doi: 10.1016/s0020-7519(98)00008-3. [PMID: 9602388]
  • D J Morré, H Zeichhardt, H G Maxeiner, H P Grünert, D Sawitzky, P Grieco. Effect of the quassinoids glaucarubolone and simalikalactone D on growth of cells permanently infected with feline and human immunodeficiency viruses and on viral infections. Life sciences. 1998; 62(3):213-9. doi: 10.1016/s0024-3205(97)01089-8. [PMID: 9488099]
  • D J Morré, P A Grieco, D M Morré. Mode of action of the anticancer quassinoids--inhibition of the plasma membrane NADH oxidase. Life sciences. 1998; 63(7):595-604. doi: 10.1016/s0024-3205(98)00310-5. [PMID: 9718085]
  • C Calzado-Flores, E M Guajardo-Touche, M P Carranza-Rosales, J J Segura-Luna. In vitro anti-trichomonic activity of Castela texana. Proceedings of the Western Pharmacology Society. 1998; 41(?):173-4. doi: ". [PMID: 9836284]
  • Y Raji, A F Bolarinwa. Antifertility activity of Quassia amara in male rats - in vivo study. Life sciences. 1997; 61(11):1067-74. doi: 10.1016/s0024-3205(97)00615-2. [PMID: 9307052]
  • I Kitagawa, T Mahmud, K Yokota, S Nakagawa, T Mayumi, M Kobayashi, H Shibuya. Indonesian medicinal plants. XVII. Characterization of quassinoids from the stems of Quassia indica. Chemical & pharmaceutical bulletin. 1996 Nov; 44(11):2009-14. doi: 10.1248/cpb.44.2009. [PMID: 8945767]
  • H H Ang, K L Chan, J W Mak. Effect of 7-day daily replacement of culture medium containing Eurycoma longifolia Jack constituents on the Malaysian Plasmodium falciparum isolates. Journal of ethnopharmacology. 1995 Dec; 49(3):171-5. doi: 10.1016/0378-8741(95)01321-0. [PMID: 8824743]
  • K Imamura, N Fukamiya, M Nakamura, M Okano, K Tagahara, K H Lee. Bruceanols G and H cytotoxic quassinoids from Brucea antidysenterica. Journal of natural products. 1995 Dec; 58(12):1915-9. doi: 10.1021/np50126a019. [PMID: 8691212]
  • C Calzado-Flores, J J Segura-Luna. In vitro cytotoxicity of chaparrin from Castela texana. Proceedings of the Western Pharmacology Society. 1995; 38(?):49-50. doi: . [PMID: 7480018]
  • C Calzado-Flores, J J Segura-Luna, E M Guajardo-Touche. Effects of chaparrin, nordihydroguaiaretic acid and their structural analogues on Entamoeba histolytica cultures. Proceedings of the Western Pharmacology Society. 1995; 38(?):105-6. doi: . [PMID: 7479999]
  • C Moretti, E Deharo, M Sauvain, C Jardel, P T David, M Gasquet. Antimalarial activity of cedronin. Journal of ethnopharmacology. 1994 Jun; 43(1):57-61. doi: 10.1016/0378-8741(94)90117-1. [PMID: 7967650]
  • J A Cabral, J D McChesney, W K Milhous. A new antimalarial quassinoid from Simaba guianensis. Journal of natural products. 1993 Nov; 56(11):1954-61. doi: 10.1021/np50101a014. [PMID: 8289064]
  • D A Evans, R K Raj. Larvicidal efficacy of Quassin against Culex quinquefasciatus. The Indian journal of medical research. 1991 Sep; 93(?):324-7. doi: ". [PMID: 1778621]
  • E Okuyama, L H Gao, M Yamazaki. [Studies on pharmacologically active principles from Indonesian crude drugs. III. Toxic components from Brucea javanica (L.) Merr]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1990 Nov; 110(11):834-8. doi: 10.1248/yakushi1947.110.11_834. [PMID: 2082013]
  • T Ohmoto, K Koike, K Mitsunaga, H Fukuda, K Kagei. Studies on the constituents of Indonesian Picrasma javanica. III. Structures of new quassinoids, javanicins A, C and D. Chemical & pharmaceutical bulletin. 1989 Nov; 37(11):2991-4. doi: 10.1248/cpb.37.2991. [PMID: 2632044]
  • C W Wright, M J O'Neill, J D Phillipson, D C Warhurst. Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. Antimicrobial agents and chemotherapy. 1988 Nov; 32(11):1725-9. doi: 10.1128/aac.32.11.1725. [PMID: 2908094]
  • G Cragg, M Suffness. Metabolism of plant-derived anticancer agents. Pharmacology & therapeutics. 1988; 37(3):425-61. doi: 10.1016/0163-7258(88)90006-x. [PMID: 3290912]
  • M J O'Neill, D H Bray, P Boardman, K L Chan, J D Phillipson, D C Warhurst, W Peters. 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. Journal of natural products. 1987 Jan; 50(1):41-8. doi: 10.1021/np50049a007. [PMID: 3298551]
  • T Sakaki, S Yoshimura, T Tsuyuki, T Takahashi, T Honda. Yadanzioside P, a new antileukemic quassinoid glycoside from Brucea javanica (L.) Merr with the 3-O-(beta-D-glucopyranosyl)bruceantin structure. Chemical & pharmaceutical bulletin. 1986 Oct; 34(10):4447-50. doi: 10.1248/cpb.34.4447. [PMID: 3829175]
  • M J O'Neill, D H Bray, P Boardman, J D Phillipson, D C Warhurst, W Peters, M Suffness. Plants as sources of antimalarial drugs: in vitro antimalarial activities of some quassinoids. Antimicrobial agents and chemotherapy. 1986 Jul; 30(1):101-4. doi: 10.1128/aac.30.1.101. [PMID: 3530122]
  • K H Lee, N Hayashi, M Okano, H Nozaki, M Ju-Ichi. Antitumor agents, 65. Brusatol and cleomiscosin-A, antileukemic principles from Brucea javanica. Journal of natural products. 1984 May; 47(3):550-1. doi: 10.1021/np50033a030. [PMID: 6481366]
  • R J Robins, M R Morgan, M J Rhodes, J M Furze. An enzyme-linked immunosorbent assay for quassin and closely related metabolites. Analytical biochemistry. 1984 Jan; 136(1):145-56. doi: 10.1016/0003-2697(84)90316-6. [PMID: 6711803]
  • F D Gillin, D S Reiner, M Suffness. Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. Antimicrobial agents and chemotherapy. 1982 Aug; 22(2):342-5. doi: 10.1128/aac.22.2.342. [PMID: 6100431]
  • K L Fong, D H Ho, R S Benjamin, N S Brown, A Bedikian, B S Yap, C L Wiseman, W Kramer, G P Bodey. Clinical pharmacology of bruceantin by radioimmunoassay. Cancer chemotherapy and pharmacology. 1982; 9(3):169-72. doi: 10.1007/bf00257747. [PMID: 7160053]
  • J Polonsky, Z Varon, C Moretti, G R Pettit, C L Herald, J A Rideout, S B Saha, H N Khastgir. The antineoplastic quassinoids of Simaba cuspidata spruce and Ailanthus grandis Prain. Journal of natural products. 1980 Jul; 43(4):503-9. doi: 10.1021/np50010a012. [PMID: 7431025]
  • W J Suling, C W Woolley, W M Shannon. Disposition and metabolism of bruceantin in the mouse. Cancer chemotherapy and pharmacology. 1979; 3(3):171-6. doi: 10.1007/bf00262418. [PMID: 527207]
  • M C Wani, H L Taylor, J B Thompson, M E Wall. Plant antitumor agents. XVI. 6alpha-Senecioyloxy-chaparrinone, a new antileukemic quassinoid from Simaba multiflora. Lloydia. 1978 Nov; 41(6):578-83. doi: . [PMID: 732540]
  • J Polonsky, Z Varon, H Jacquemin, G R Pettit. The isolation and structure of 13,18-dehydroglaucarubinone, a new antineoplastic quassinoid from Simarouba amara. Experientia. 1978 Sep; 34(9):1122-3. doi: 10.1007/bf01922904. [PMID: 720499]
  • P C Ghosh, J E Larrahondo, P W LeQuesne, R F Raffauf. Antitumor plants. IV. Constituents of Simarouba versicolor. Lloydia. 1977 Jul; 40(4):364-9. doi: . [PMID: 895397]