3-Methoxynobiletin (BioDeep_00000017370)

   

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-

化学式: C22H24O9 (432.14202539999997)
中文名称: 3,5,6,7,8,3',4'-七甲氧基黄酮, 3,5,6,7,8,3,4-七甲氧基黄酮, 3,5,6,7,8,3',4'-七甲氧基黄酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.51%

分子结构信息

SMILES: c1(c(c(c2c(c1OC)oc(c(c2=O)OC)c1ccc(c(c1)OC)OC)OC)OC)OC
InChI: InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3

描述信息

3-Methoxynobiletin is a member of flavonoids and an ether.
3,3,4,5,6,7,8-Heptamethoxyflavone is a natural product found in Croton caudatus, Melicope triphylla, and other organisms with data available.
See also: Tangerine peel (part of); Citrus aurantium fruit rind (part of).
Isolated from Citrus subspecies peels. 3-Methoxynobiletin is found in sweet orange, sweet bay, and citrus.
3-Methoxynobiletin is found in citrus. 3-Methoxynobiletin is isolated from Citrus species peels.
3,5,6,7,8,3',4'-heptamethoxyflavone, a flavonoid in Citrus reticulata peels, exhibits anti-tumor-initiating effect and Anti-neuroinflammatory activity[1][2][3]. 3,5,6,7,8,3',4'-heptamethoxyflavone inhibits collagenase activity and increased type I procollagen content in HDFn cells[1]. 3,5,6,7,8,3',4'-heptamethoxyflavone induces brain-derived neurotrophic factor (BDNF) expression via cAMP/ERK/CREB signaling and reduces phosphodiesterase activity in C6 cells[4].
3,5,6,7,8,3',4'-heptamethoxyflavone, a flavonoid in Citrus reticulata peels, exhibits anti-tumor-initiating effect and Anti-neuroinflammatory activity[1][2][3]. 3,5,6,7,8,3',4'-heptamethoxyflavone inhibits collagenase activity and increased type I procollagen content in HDFn cells[1]. 3,5,6,7,8,3',4'-heptamethoxyflavone induces brain-derived neurotrophic factor (BDNF) expression via cAMP/ERK/CREB signaling and reduces phosphodiesterase activity in C6 cells[4].

同义名列表

25 个代谢物同义名

4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-; 2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-1-benzopyran-4-one; 2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-chromen-4-one; 2-(3,4-Dimethoxy-phenyl)-3,5,6,7,8-pentamethoxy-chromen-4-one; 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one; 3,?5,?6,?7,?8,?3,?4-?Heptemthoxyflavone; 3, 5, 6, 7, 8, 3, 4-Heptemthoxyflavone; Flavone, 3,3,4,5,6,7,8-heptamethoxy-; 5.3,5,6,7,8,3,4-Heptamethoxyflavone; 3,5,6,7,8,3’,4’- heptemthoxyflavone; 3,5,6,7,8,3,4-Heptamethphoxyflavone; 3,5,6,7,8,3,4-Heptamethoxy-Flavone; 3,3,4,5,6,7,8-heptamethoxyflavone; 3,5,6,7,8,3,4-heptamethoxyflavone; 3,4,3,5,6,7,8-heptamethoxyflavone; 3,5,6,7,8,3,4-heptemthoxyflavone; 3567834-Heptamethoxy-flavone; SSXJHQZOHUYEGD-UHFFFAOYSA-N; 3567834-Heptamethoxyflavone; 3-Methoxynobiletin; NCI60_005664; C22H24O9; Hepta-3; 3-Hptmf; 3,?5,?6,?7,?8,?3',?4'-?Heptemthoxyflavone



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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

  • Yoshiko Furukawa, Satoshi Okuyama, Yoshiaki Amakura, Atsushi Sawamoto, Mitsunari Nakajima, Morio Yoshimura, Michiya Igase, Naohiro Fukuda, Takahisa Tamai, Takashi Yoshida. Isolation and Characterization of Neuroprotective Components from Citrus Peel and Their Application as Functional Food. Chemical & pharmaceutical bulletin. 2021; 69(1):2-10. doi: 10.1248/cpb.c20-00265. [PMID: 33390517]
  • Atsushi Sawamoto, Masayuki Nakanishi, Satoshi Okuyama, Yoshiko Furukawa, Mitsunari Nakajima. Heptamethoxyflavone inhibits adipogenesis via enhancing PKA signaling. European journal of pharmacology. 2019 Dec; 865(?):172758. doi: 10.1016/j.ejphar.2019.172758. [PMID: 31672599]
  • Konglong Feng, Xiaoai Zhu, Tong Chen, Bo Peng, Muwen Lu, Hui Zheng, Qingrong Huang, Chi-Tang Ho, Yunjiao Chen, Yong Cao. Prevention of Obesity and Hyperlipidemia by Heptamethoxyflavone in High-fat Diet-induced Rats. Journal of agricultural and food chemistry. 2019 Mar; 67(9):2476-2489. doi: 10.1021/acs.jafc.8b05632. [PMID: 30740980]
  • Norihiro Yoshizaki, Ron Hashizume, Hitoshi Masaki. A polymethoxyflavone mixture extracted from orange peels, mainly containing nobiletin, 3,3',4',5,6,7,8-heptamethoxyflavone and tangeretin, suppresses melanogenesis through the acidification of cell organelles, including melanosomes. Journal of dermatological science. 2017 Oct; 88(1):78-84. doi: 10.1016/j.jdermsci.2017.06.008. [PMID: 28629701]
  • Yu Wang, Pei-Sheng Lee, Yi-Fen Chen, Chi-Tang Ho, Min-Hsiung Pan. Suppression of Adipogenesis by 5-Hydroxy-3,6,7,8,3',4'-Hexamethoxyflavone from Orange Peel in 3T3-L1 Cells. Journal of medicinal food. 2016 Sep; 19(9):830-5. doi: 10.1089/jmf.2016.0060. [PMID: 27542074]
  • Thi Van Anh Tran, Clemens Malainer, Stefan Schwaiger, Atanas G Atanasov, Elke H Heiss, Verena M Dirsch, Hermann Stuppner. NF-κB inhibitors from Eurycoma longifolia. Journal of natural products. 2014 Mar; 77(3):483-8. doi: 10.1021/np400701k. [PMID: 24467387]
  • Mei-Chun Kou, Shih-Hang Fu, Jui-Hung Yen, Ching-Yi Weng, Shiming Li, Chi-Tang Ho, Ming-Jiuan Wu. Effects of citrus flavonoids, 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone and 3,5,6,7,8,3',4'-heptamethoxyflavone, on the activities of macrophage scavenger receptors and the hepatic LDL receptor. Food & function. 2013 Apr; 4(4):602-9. doi: 10.1039/c3fo30301b. [PMID: 23370792]
  • Matsutake Higa, Megumi Imamura, Kanae Shimoji, Kazuhito Ogihara, Toshimasa Suzuka. Isolation of six new flavonoids from Melicope triphylla. Chemical & pharmaceutical bulletin. 2012; 60(9):1112-7. doi: 10.1248/cpb.c12-00213. [PMID: 22976318]
  • Yoshiko Furukawa, Satoshi Okuyama, Yoshiaki Amakura, Sono Watanabe, Takahiro Fukata, Mitsunari Nakajima, Morio Yoshimura, Takashi Yoshida. Isolation and characterization of activators of ERK/MAPK from citrus plants. International journal of molecular sciences. 2012; 13(2):1832-1845. doi: 10.3390/ijms13021832. [PMID: 22408427]
  • Saem Han, Hye Min Kim, Jeong Min Lee, So-Youn Mok, Sanghyun Lee. Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong. Journal of agricultural and food chemistry. 2010 Sep; 58(17):9488-91. doi: 10.1021/jf102730b. [PMID: 20698540]
  • Guo-An Zou, Zhi-Heng Su, Hong-Wu Zhang, Yuan Wang, Jun-Shan Yang, Zhong-Mei Zou. Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook. Molecules (Basel, Switzerland). 2010 Feb; 15(3):1097-102. doi: 10.3390/molecules15031097. [PMID: 20335965]
  • Guodong Zheng, Depo Yang, Dongmei Wang, Fang Zhou, Xue Yang, Lin Jiang. Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection. Journal of agricultural and food chemistry. 2009 Aug; 57(15):6552-7. doi: 10.1021/jf901225e. [PMID: 19722565]
  • Toshifumi Hirata, Misato Fujii, Kazuhiro Akita, Noriyuki Yanaka, Kaori Ogawa, Masanori Kuroyanagi, Daiki Hongo. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & medicinal chemistry. 2009 Jan; 17(1):25-8. doi: 10.1016/j.bmc.2008.11.039. [PMID: 19054677]
  • John A Manthey, Philip Bendele. Anti-inflammatory activity of an orange peel polymethoxylated flavone, 3',4',3,5,6,7,8-heptamethoxyflavone, in the rat carrageenan/paw edema and mouse lipopolysaccharide-challenge assays. Journal of agricultural and food chemistry. 2008 Oct; 56(20):9399-403. doi: 10.1021/jf801222h. [PMID: 18816060]
  • Yoshiki Miyata, Takashi Sato, Keisuke Imada, Akira Dobashi, Masamichi Yano, Akira Ito. A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells. Biochemical and biophysical research communications. 2008 Feb; 366(1):168-73. doi: 10.1016/j.bbrc.2007.11.100. [PMID: 18053806]
  • Zhenyu Wang, Shiming Li, Stephen Ferguson, Robert Goodnow, Chi-Tang Ho. Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. Journal of separation science. 2008 Jan; 31(1):30-7. doi: 10.1002/jssc.200700331. [PMID: 18095294]
  • Shiming Li, Min-Hsiung Pan, Ching-Shu Lai, Chih-Yu Lo, Slavik Dushenkov, Chi-Tang Ho. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic & medicinal chemistry. 2007 May; 15(10):3381-9. doi: 10.1016/j.bmc.2007.03.021. [PMID: 17391969]
  • Ernestina Almada-Ruiz, Miguel Angel Martínez-Téllez, Maria M Hernández-Alamos, Socorro Vallejo, Eduardo Primo-Yúfera, Irasema Vargas-Arispuro. Fungicidal potential of methoxylated flavones from citrus for in vitro control of Colletotrichum gloeosporioides, causal agent of anthracnose disease in tropical fruits. Pest management science. 2003 Nov; 59(11):1245-9. doi: 10.1002/ps.747. [PMID: 14620052]
  • H Wangensteen, E Molden, H Christensen, K E Malterud. Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel. European journal of clinical pharmacology. 2003 Feb; 58(10):663-8. doi: 10.1007/s00228-002-0537-3. [PMID: 12610742]
  • A Ortuño, M C Arcas, J M Botía, M D Fuster, J A Del Río. Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels. Journal of agricultural and food chemistry. 2002 May; 50(10):2836-9. doi: 10.1021/jf011382a. [PMID: 11982408]
  • B Delaney, K Phillips, C Vasquez, A Wilson, D Cox, H-B Wang, J Manthey. Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2002 May; 40(5):617-24. doi: 10.1016/s0278-6915(02)00007-8. [PMID: 11955667]
  • B Delaney, K Phillips, D Buswell, B Mowry, D Nickels, D Cox, H B Wang, J Manthey. Immunotoxicity of a standardized citrus polymethoxylated flavone extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Nov; 39(11):1087-94. doi: 10.1016/s0278-6915(01)00058-8. [PMID: 11527568]
  • Y Iwase, Y Takemura, M Ju-ichi, M Yano, C Ito, H Furukawa, T Mukainaka, M Kuchide, H Tokuda, H Nishino. Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants. Cancer letters. 2001 Feb; 163(1):7-9. doi: 10.1016/s0304-3835(00)00691-1. [PMID: 11163102]
  • T Ikegawa, F Ushigome, N Koyabu, S Morimoto, Y Shoyama, M Naito, T Tsuruo, H Ohtani, Y Sawada. Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer letters. 2000 Nov; 160(1):21-8. doi: 10.1016/s0304-3835(00)00549-8. [PMID: 11098080]
  • Y Iwase, Y Takemura, M Ju-ichi, C Ito, H Furukawa, S Kawaii, M Yano, X Y Mou, J Takayasu, H Tokuda, H Nishino. Inhibitory effect of flavonoids from citrus plants on Epstein-Barr virus activation and two-stage carcinogenesis of skin tumors. Cancer letters. 2000 Jun; 154(1):101-5. doi: 10.1016/s0304-3835(00)00386-4. [PMID: 10799745]
  • S Qian, L Chen. [Studies on the chemical constituents of Citrus reticulata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 1998 Jun; 21(6):301-2. doi: ". [PMID: 12567525]
  • M Itoigawa, K Takeya, H Furukawa. Cardiotonic flavonoids from Citrus plants (Rutaceae). Biological & pharmaceutical bulletin. 1994 Nov; 17(11):1519-21. doi: 10.1248/bpb.17.1519. [PMID: 7703977]