2,6-Dimethoxy-1,4-benzoquinone (BioDeep_00000003859)

Main id: BioDeep_00000407536

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


3,5-Dimethoxy-1,4-benzoquinone; 3,5-Dimethoxybenzoquinone; NSC 24500

化学式: C8H8O4 (168.0423)
中文名称: 2,6-二甲氧基-1,4-苯醌
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(=CC(=O)C=C(C1=O)OC)OC
InChI: InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3

描述信息

2,6-Dimethoxy-1,4-benzoquinone is a natural product found in Diospyros eriantha, Iris milesii, and other organisms with data available.
2,6-Dimethoxyquinone is a methoxy-substituted benzoquinone and bioactive compound found in fermented wheat germ extracts, with potential antineoplastic and immune-enhancing activity. 2,6-Dimethoxyquinone (2,6-DMBQ) inhibits anaerobic glycolysis thereby preventing cellular metabolism and inducing apoptosis. As cancer cells use the anaerobic glycolysis pathway to metabolize glucose and cancer cells proliferate at an increased rate as compared to normal, healthy cells, this agent is specifically cytotoxic towards cancer cells. In addition, 2,6-DMBQ exerts immune-enhancing effects by increasing natural killer (NK) cell and T-cell activity against cancer cells.
See also: Acai fruit pulp (part of).
2,6-Dimethoxy-1,4-benzoquinone is found in common wheat. 2,6-Dimethoxy-1,4-benzoquinone is a constituent of bark of Phyllostachys heterocycla var. pubescens (moso bamboo)
Constituent of bark of Phyllostachys heterocycla variety pubescens (moso bamboo). 2,6-Dimethoxy-1,4-benzoquinone is found in green vegetables and common wheat.
2,6-Dimethoxy-1,4-benzoquinone, a natural phytochemical, is a known haustorial inducing factor. 2,6-Dimethoxy-1,4-benzoquinone exerts anti-cancer, anti-inflammatory, anti-adipogenic, antibacterial, and antimalaria effects[1].
2,6-Dimethoxy-1,4-benzoquinone, a natural phytochemical, is a known haustorial inducing factor. 2,6-Dimethoxy-1,4-benzoquinone exerts anti-cancer, anti-inflammatory, anti-adipogenic, antibacterial, and antimalaria effects[1].

同义名列表

51 个代谢物同义名

3,5-Dimethoxy-1,4-benzoquinone; 3,5-Dimethoxybenzoquinone; NSC 24500; 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-, radical ion(1-); InChI=1/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3; 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy- (9CI); 2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-; 2,6-dimethoxycyclohexa-2,5-diene-1,4-dione; 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione; 2,6-Dimethoxy-1,4-benzoquinone, 97\\%; 2,6-Dimethoxysemiquinone radicals; 2,6-dimethoxy-[1,4]benzoquinone; 2,6-Dimethoxysemiquinone anions; 2, 6-Dimethoxy-1,4-benzoquinone; 2,6-Dimethoxy-1,4-benzoquinone; p-Benzoquinone, 2,6-dimethoxy-; 3,5-Dimethoxy-1,4-benzoquinone; 2,6-Dimethoxybenzo-1,4-quinone; 2,6-dimethoxy[1,4]benzoquinone; 2, 6-Dimethoxy-p-benzoquinone; 2,6-dimethoxy-p-benzoquinone; p-Benzoquinone,6-dimethoxy-; 2,6-Dimetoxy-p-benzoquinone; DIMETHOXYBENZOQUINONE,2,6-; OLBNOBQOQZRLMP-UHFFFAOYSA-; 2,4-dione, 2,6-dimethoxy-; 2,6-Dimethoxybenzoquinone; 2,6-DIMETHOXYQUINONE [MI]; DIMETHOXYBENZOQUINONE,6-; Quinone, 2,6-dimethoxy-; 2,6-Dimethoxy-p-quinone; ghl.PD_Mitscher_leg0.4; 2, 6-Dimethoxyquinone; 2,6-Dimethoxyquinone; Maybridge1_002628; Spectrum5_000335; Spectrum2_000781; Spectrum4_001608; Spectrum3_000177; UNII-1Z701W789S; DivK1c_001380; KBio2_006339; KBio2_003771; KBio2_001203; KBio3_001173; NCI60_001958; CDS1_000340; 1Z701W789S; 2,6-DMBQ; DMBQ; KIA; 2,6-Dimethoxybenzoquinone; 2,6-Dimethoxy-1,4-benzoquinone



数据库引用编号

21 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)

201 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。

亚细胞结构定位 关联基因列表
Cytoplasm 17 ADIG, ANXA5, ANXA6, CCNB1, CDH1, CRYZ, EIF4EBP1, FASN, MAPK14, MTOR, NQO1, PIK3CA, PIK3R6, PRKAA2, PRKX, RPS6KA2, STAT3
Peripheral membrane protein 4 ANXA5, ANXA6, MTOR, PIK3R6
Endoplasmic reticulum membrane 1 MTOR
Nucleus 13 ADIG, CCNB1, CDH1, CEBPA, EIF4EBP1, MAPK14, MTOR, NQO1, PPARGC1A, PRKAA2, PRKX, RPS6KA2, STAT3
cytosol 15 ANXA5, CCNB1, CDH1, CRYZ, EIF4EBP1, FASN, MAPK14, MTOR, NQO1, PIK3CA, PIK3R6, PPARGC1A, PRKAA2, RPS6KA2, STAT3
dendrite 3 MTOR, NQO1, PRKAA2
phagocytic vesicle 1 MTOR
trans-Golgi network 1 CDH1
centrosome 1 CCNB1
nucleoplasm 10 CCNB1, CDH1, CEBPA, MAPK14, MTOR, PPARGC1A, PRKAA2, PRKX, RPS6KA2, STAT3
RNA polymerase II transcription regulator complex 2 CEBPA, STAT3
Cell membrane 2 CDH1, PIK3R6
Cytoplasmic side 1 MTOR
lamellipodium 2 CDH1, PIK3CA
Golgi apparatus membrane 1 MTOR
Synapse 2 NQO1, RPS6KA2
cell junction 1 CDH1
glutamatergic synapse 2 CDH1, MAPK14
Golgi apparatus 3 CDH1, FASN, PRKAA2
Golgi membrane 1 MTOR
lysosomal membrane 3 ANXA6, EGF, MTOR
neuronal cell body 2 NQO1, PRKAA2
postsynapse 1 CDH1
sarcolemma 2 ANXA5, ANXA6
Cytoplasm, cytosol 1 NQO1
Lysosome 1 MTOR
endosome 1 CDH1
plasma membrane 6 CDH1, EGF, FASN, PIK3CA, PIK3R6, STAT3
Membrane 11 ADIG, ANXA5, ANXA6, CCNB1, CDH1, EGF, FASN, MTOR, NQO1, PIK3R6, PRKAA2
axon 1 PRKAA2
extracellular exosome 6 ANXA5, ANXA6, CDH1, CRYZ, EGF, FASN
Lysosome membrane 1 MTOR
extracellular space 1 EGF
perinuclear region of cytoplasm 3 ANXA6, CDH1, PIK3CA
adherens junction 1 CDH1
intercalated disc 1 PIK3CA
mitochondrion 3 ANXA6, CRYZ, MAPK14
intracellular membrane-bounded organelle 1 CEBPA
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 CDH1
Secreted 1 ADIG
extracellular region 5 ADIG, ANXA5, CDH1, EGF, MAPK14
cytoplasmic side of plasma membrane 1 CDH1
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 1 ADIG
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 1 CCNB1
transcription regulator complex 2 CEBPA, STAT3
nuclear membrane 1 CDH1
external side of plasma membrane 1 ANXA5
actin cytoskeleton 1 CDH1
nucleolus 1 CEBPA
focal adhesion 2 ANXA5, ANXA6
Cell junction, adherens junction 1 CDH1
flotillin complex 1 CDH1
Nucleus, PML body 2 MTOR, PPARGC1A
PML body 2 MTOR, PPARGC1A
collagen-containing extracellular matrix 2 ANXA5, ANXA6
lateral plasma membrane 1 CDH1
nuclear speck 2 MAPK14, PRKAA2
Zymogen granule membrane 2 ANXA5, ANXA6
chromatin 3 CEBPA, PPARGC1A, STAT3
Late endosome membrane 1 ANXA6
Golgi apparatus, trans-Golgi network 1 CDH1
spindle pole 2 CCNB1, MAPK14
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
Lipid droplet 1 ADIG
Melanosome 2 ANXA6, FASN
cytoplasmic stress granule 1 PRKAA2
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
platelet alpha granule lumen 1 EGF
phosphatidylinositol 3-kinase complex 2 PIK3CA, PIK3R6
phosphatidylinositol 3-kinase complex, class IA 2 PIK3CA, PIK3R6
anaphase-promoting complex 1 CDH1
outer kinetochore 1 CCNB1
vesicle membrane 2 ANXA5, ANXA6
clathrin-coated endocytic vesicle membrane 1 EGF
[Isoform 2]: Nucleus 1 CDH1
[Isoform 1]: Nucleus 1 PPARGC1A
apical junction complex 1 CDH1
nucleotide-activated protein kinase complex 1 PRKAA2
Cell junction, desmosome 1 CDH1
desmosome 1 CDH1
Cytoplasmic vesicle, phagosome 1 MTOR
catenin complex 1 CDH1
ribosome 1 RPS6KA2
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
C/EBP complex 1 CEBPA
CHOP-C/EBP complex 1 CEBPA
phosphatidylinositol 3-kinase complex, class IB 2 PIK3CA, PIK3R6
glycogen granule 1 FASN
[Isoform 4]: Nucleus, nucleolus 1 CEBPA
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Anuphon Laohavisit, Takanori Wakatake, Nobuaki Ishihama, Hugh Mulvey, Kaori Takizawa, Takamasa Suzuki, Ken Shirasu. Quinone perception in plants via leucine-rich-repeat receptor-like kinases. Nature. 2020 11; 587(7832):92-97. doi: 10.1038/s41586-020-2655-4. [PMID: 32879491]
  • Christoph Otto, Theresa Hahlbrock, Kilian Eich, Ferdi Karaaslan, Constantin Jürgens, Christoph-Thomas Germer, Armin Wiegering, Ulrike Kämmerer. Antiproliferative and antimetabolic effects behind the anticancer property of fermented wheat germ extract. BMC complementary and alternative medicine. 2016 Jun; 16(?):160. doi: 10.1186/s12906-016-1138-5. [PMID: 27245162]
  • Songkui Cui, Takanori Wakatake, Kei Hashimoto, Simon B Saucet, Kiminori Toyooka, Satoko Yoshida, Ken Shirasu. Haustorial Hairs Are Specialized Root Hairs That Support Parasitism in the Facultative Parasitic Plant Phtheirospermum japonicum. Plant physiology. 2016 Mar; 170(3):1492-503. doi: 10.1104/pp.15.01786. [PMID: 26712864]
  • Patricia L Judson, Entidhar Al Sawah, Douglas C Marchion, Yin Xiong, Elona Bicaku, Nadim Bou Zgheib, Hye Sook Chon, Xiaomang B Stickles, Ardeshir Hakam, Robert M Wenham, Sachin M Apte, Jesus Gonzalez-Bosquet, Dung-Tsa Chen, Johnathan M Lancaster. Characterizing the efficacy of fermented wheat germ extract against ovarian cancer and defining the genomic basis of its activity. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society. 2012 Jul; 22(6):960-7. doi: 10.1097/igc.0b013e318258509d. [PMID: 22740002]
  • Netiya Karaket, Kanyaratt Supaibulwatana, Supatsara Ounsuk, Valérie Bultel-Poncé, Van Cuong Pham, Bernard Bodo. Chemical and bioactivity evaluation of the bark of Neonauclea purpurea. Natural product communications. 2012 Feb; 7(2):169-70. doi: . [PMID: 22474944]
  • Pradeepa C G Bandaranayake, Alexey Tomilov, Natalya B Tomilova, Quy A Ngo, Norman Wickett, Claude W dePamphilis, John I Yoder. The TvPirin gene is necessary for haustorium development in the parasitic plant Triphysaria versicolor. Plant physiology. 2012 Feb; 158(2):1046-53. doi: 10.1104/pp.111.186858. [PMID: 22128136]
  • Nikolai Scherbak, Anneli Ala-Häivälä, Mikael Brosché, Nathalie Böwer, Hilja Strid, John R Gittins, Elin Grahn, Leif A Eriksson, Åke Strid. The pea SAD short-chain dehydrogenase/reductase: quinone reduction, tissue distribution, and heterologous expression. Plant physiology. 2011 Apr; 155(4):1839-50. doi: 10.1104/pp.111.173336. [PMID: 21343423]
  • Juliane K Ishida, Satoko Yoshida, Masaki Ito, Shigetou Namba, Ken Shirasu. Agrobacterium rhizogenes-mediated transformation of the parasitic plant Phtheirospermum japonicum. PloS one. 2011; 6(10):e25802. doi: 10.1371/journal.pone.0025802. [PMID: 21991355]
  • Pedro Sanchez-Cruz, Carmelo Garcia, Antonio E Alegria. Role of quinones in the ascorbate reduction rates of S-nitrosoglutathione. Free radical biology & medicine. 2010 Nov; 49(9):1387-94. doi: 10.1016/j.freeradbiomed.2010.07.022. [PMID: 20691779]
  • Myung-Hee Kim, Sung-Hoon Jo, Kyung-Soo Ha, Ji-Hye Song, Hae-Dong Jang, Young-In Kwon. Antimicrobial activities of 1,4-benzoquinones and wheat germ extract. Journal of microbiology and biotechnology. 2010 Aug; 20(8):1204-9. doi: 10.4014/jmb.1004.04037. [PMID: 20798583]
  • Guy Merlin Kuigoua, Simeon F Kouam, Bonaventure T Ngadjui, Barbara Schulz, Ivan R Green, M Iqbal Choudhary, Karsten Krohn. Minor secondary metabolic products from the stem bark of Plumeria rubra Linn. displaying antimicrobial activities. Planta medica. 2010 Apr; 76(6):620-5. doi: 10.1055/s-0029-1240611. [PMID: 19937550]
  • Rickie B Turley, Earl Taliercio. Cotton benzoquinone reductase: up-regulation during early fiber development and heterologous expression and characterization in Pichia pastoris. Plant physiology and biochemistry : PPB. 2008 Aug; 46(8-9):780-5. doi: 10.1016/j.plaphy.2008.04.016. [PMID: 18534861]
  • Xiao-lan Wang, Kai-bei Yu, Shu-lin Peng. [Chemical constituents of aerial part of Acalypha australis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jun; 33(12):1415-7. doi: . [PMID: 18837345]
  • James T Heimbach, Gyula Sebestyen, Gabor Semjen, Elke Kennepohl. Safety studies regarding a standardized extract of fermented wheat germ. International journal of toxicology. 2007 May; 26(3):253-9. doi: 10.1080/10915810701369709. [PMID: 17564907]
  • Yao-Lan Li, Guan Wang, Jun-Yi Xue, Ying-Zhou Cen. [Studies on chemical constituents from Serissa serissoides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(7):605-8. doi: ". [PMID: 17583202]
  • Luc Meva'a Mbaze, Herve Martial P Poumale, Jean Duplex Wansi, Jean Alexandre Lado, Shamsun Nahar Khan, Muhammad Choudhary Iqbal, Bonaventure Tchaleu Ngadjui, Hartmut Laatsch. alpha-Glucosidase inhibitory pentacyclic triterpenes from the stem bark of Fagara tessmannii (Rutaceae). Phytochemistry. 2007 Mar; 68(5):591-5. doi: 10.1016/j.phytochem.2006.12.015. [PMID: 17270224]
  • Rudiyansyah, Mary J Garson. Secondary metabolites from the wood bark of Durio zibethinus and Durio kutejensis. Journal of natural products. 2006 Aug; 69(8):1218-21. doi: 10.1021/np050553t. [PMID: 16933881]
  • Manuel J Torres, Alexey A Tomilov, Natalya Tomilova, Russell L Reagan, John I Yoder. Pscroph, a parasitic plant EST database enriched for parasite associated transcripts. BMC plant biology. 2005 Nov; 5(?):24. doi: 10.1186/1471-2229-5-24. [PMID: 16288663]
  • Ru-Wei Lin, Ian-Lih Tsai, Chang-Yih Duh, Kuo-Hsiung Lee, Ih-Sheng Chen. New lignans and cytotoxic constituents from Wikstroemia lanceolata. Planta medica. 2004 Mar; 70(3):234-8. doi: 10.1055/s-2004-815540. [PMID: 15114500]
  • F Jakab, Y Shoenfeld, A Balogh, M Nichelatti, A Hoffmann, Zs Kahán, K Lapis, A Mayer, P Sápy, F Szentpétery, A Telekes, L Thurzó, A Vágvölgyi, M Hidvégi. A medical nutriment has supportive value in the treatment of colorectal cancer. British journal of cancer. 2003 Aug; 89(3):465-9. doi: 10.1038/sj.bjc.6601153. [PMID: 12888813]
  • Wei-Yu Lin, Yueh-Hsiung Kuo, Ya-Ling Chang, Che-Ming Teng, Eng-Chi Wang, Tsutomu Ishikawa, Ih-Sheng Chen. Anti-platelet aggregation and chemical constituents from the rhizome of Gynura japonica. Planta medica. 2003 Aug; 69(8):757-64. doi: 10.1055/s-2003-42796. [PMID: 14531028]
  • Fang-Rong Chang, Tian-Jye Hsieh, Ti-Lung Huang, Chung-Yi Chen, Reen-Yen Kuo, Yuh-Chwen Chang, Hui-Fen Chiu, Yang-Chang Wu. Cytotoxic constituents of the stem bark of Neolitsea acuminatissima. Journal of natural products. 2002 Mar; 65(3):255-8. doi: 10.1021/np010236w. [PMID: 11908960]
  • Mei-Ing Chung, Jing-Ru Weng, Jih-Pyang Wang, Che-Ming Teng, Chun-Nan Lin. Antiplatelet and anti-inflammatory constituents and new oxygenated xanthones from Hypericum geminiflorum. Planta medica. 2002 Jan; 68(1):25-9. doi: 10.1055/s-2002-19871. [PMID: 11842322]
  • A Zalatnai, K Lapis, B Szende, E Rásó, A Telekes, Resetár A, M Hidvégi. Wheat germ extract inhibits experimental colon carcinogenesis in F-344 rats. Carcinogenesis. 2001 Oct; 22(10):1649-52. doi: 10.1093/carcin/22.10.1649. [PMID: 11577004]
  • M Matvienko, M J Torres, J I Yoder. Transcriptional responses in the hemiparasitic plant Triphysaria versicolor to host plant signals. Plant physiology. 2001 Sep; 127(1):272-82. doi: 10.1104/pp.127.1.272. [PMID: 11553755]
  • T Estlander, R Jolanki, K Alanko, L Kanerva. Occupational allergic contact dermatitis caused by wood dusts. Contact dermatitis. 2001 Apr; 44(4):213-7. doi: 10.1034/j.1600-0536.2001.044004213.x. [PMID: 11260236]
  • R L Wrobel, J I Yoder. Differential RNA expression of alpha-expansin gene family members in the parasitic angiosperm Triphysaria versicolor (Scrophulariaceae). Gene. 2001 Mar; 266(1-2):85-93. doi: 10.1016/s0378-1119(01)00376-6. [PMID: 11290422]
  • M Matvienko, A Wojtowicz, R Wrobel, D Jamison, Y Goldwasser, J I Yoder. Quinone oxidoreductase message levels are differentially regulated in parasitic and non-parasitic plants exposed to allelopathic quinones. The Plant journal : for cell and molecular biology. 2001 Feb; 25(4):375-87. doi: 10.1046/j.1365-313x.2001.00971.x. [PMID: 11260494]
  • G Brambilla, L Robbiano, E Cajelli, A Martelli, F Turmolini, M Mazzei. Cytotoxic, DNA-damaging and mutagenic properties of 2,6-dimethoxy-1,4-benzoquinone, formed by dimethophrine-nitrite interaction. The Journal of pharmacology and experimental therapeutics. 1988 Mar; 244(3):1011-5. doi: . [PMID: 3252018]
  • B M Hausen, A Shoji, O Jarchow. Orchid allergy. Archives of dermatology. 1984 Sep; 120(9):1206-8. doi: . [PMID: 6476858]
  • S S Handa, A D Kinghorn, G A Cordell, N R Farnsworth. Plant anticancer agents. XXVI. Constituents of Peddiea fischeri. Journal of natural products. 1983 Mar; 46(2):248-50. doi: 10.1021/np50026a020. [PMID: 6875580]