Lawsone methyl ether (BioDeep_00000269381)

 

Secondary id: BioDeep_00000863463

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2-Methoxy-1,4-naphthoquinone

化学式: C11H8O3 (188.0473)
中文名称: 2-甲氧基-1,4-萘醌, 二氯甲基甲醚, 2-甲氧基-1,4-萘并醌
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 95.45%

分子结构信息

SMILES: c1ccc2c(c1)C(=O)C(=CC2=O)OC
InChI: InChI=1S/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3

描述信息

A naphthoquinone that is naphthalene-1,4-dione substituted by a methoxy group at position 2. It has been isolated from the roots of Rubia yunnanensis.
Lawsone methyl ether (2-Methoxy-1,4-naphthoquinone), isolated from Impatiens balsamina L. and Swertia calycina, exhibits potent antifungal and antibacterial activities[1].
Lawsone methyl ether (2-Methoxy-1,4-naphthoquinone), isolated from Impatiens balsamina L. and Swertia calycina, exhibits potent antifungal and antibacterial activities[1].

同义名列表

3 个代谢物同义名

2-Methoxy-1,4-naphthoquinone; Lawsone methyl ether; 2-?Methoxy-?1,?4-?naphthoquinone



数据库引用编号

9 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)

2 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


文献列表

  • Beatrycze Nowicka, Jan Walczak, Maja Kapsiak, Karolina Barnaś, Julia Dziuba, Aleksandra Suchoń. Impact of cytotoxic plant naphthoquinones, juglone, plumbagin, lawsone and 2-methoxy-1,4-naphthoquinone, on Chlamydomonas reinhardtii reveals the biochemical mechanism of juglone toxicity by rapid depletion of plastoquinol. Plant physiology and biochemistry : PPB. 2023 Apr; 197(?):107660. doi: 10.1016/j.plaphy.2023.107660. [PMID: 36996637]
  • R R Bazmi, P Panichayupakaranant. Synergistic interactions between artocarpin-rich extract, lawsone methyl ether and ampicillin on anti-MRSA and their antibiofilm formation. Letters in applied microbiology. 2022 May; 74(5):777-786. doi: 10.1111/lam.13662. [PMID: 35100449]
  • M S Meah, M Lertcanawanichakul, P Pedpradab, W Lin, K Zhu, G Li, P Panichayupakaranant. Synergistic effect on anti-methicillin-resistant Staphylococcus aureus among combinations of α-mangostin-rich extract, lawsone methyl ether and ampicillin. Letters in applied microbiology. 2020 Nov; 71(5):510-519. doi: 10.1111/lam.13369. [PMID: 32770753]
  • Lian Chee Foong, Jian Yi Chai, Anthony Siong Hock Ho, Brandon Pei Hui Yeo, Yang Mooi Lim, Sheh May Tam. Comparative transcriptome analysis to identify candidate genes involved in 2-methoxy-1,4-naphthoquinone (MNQ) biosynthesis in Impatiens balsamina L. Scientific reports. 2020 09; 10(1):16123. doi: 10.1038/s41598-020-72997-2. [PMID: 32999341]
  • Meixia Guo, Jun Liu, Zhenlin Xu, Jie Wang, Taotao Li, Hongtao Lei, Xuewu Duan, Yuanming Sun, Xiaoyong Zhang, Riming Huang. 2-Methoxy-1,4-naphthoquinone Induces Metabolic Shifts in Penicillium Digitatum Revealed by High-Dimensional Biological Data. Journal of agricultural and food chemistry. 2020 Sep; 68(36):9697-9706. doi: 10.1021/acs.jafc.0c03396. [PMID: 32803964]
  • M Chen, M L Vial, L Gee, R A Davis, J A St John, J A K Ekberg. The plant natural product 2-methoxy-1,4-naphthoquinone stimulates therapeutic neural repair properties of olfactory ensheathing cells. Scientific reports. 2020 01; 10(1):951. doi: 10.1038/s41598-020-57793-2. [PMID: 31969642]
  • Wipawee Nittayananta, Surasak Limsuwan, Teerapol Srichana, Chutha Sae-Wong, Thanaporn Amnuaikit. Oral spray containing plant-derived compounds is effective against common oral pathogens. Archives of oral biology. 2018 Jun; 90(?):80-85. doi: 10.1016/j.archoralbio.2018.03.002. [PMID: 29573647]
  • Alessio Cimmino, Véronique Mathieu, Marco Evidente, Marlène Ferderin, Laetitia Moreno Y Banuls, Marco Masi, Annelise De Carvalho, Robert Kiss, Antonio Evidente. Glanduliferins A and B, two new glucosylated steroids from Impatiens glandulifera, with in vitro growth inhibitory activity in human cancer cells. Fitoterapia. 2016 Mar; 109(?):138-45. doi: 10.1016/j.fitote.2015.12.016. [PMID: 26732071]
  • Jun-Ting Fan, Bin Kuang, Guang-Zhi Zeng, Si-Meng Zhao, Chang-Jiu Ji, Yu-Mei Zhang, Ning-Hua Tan. Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis. Journal of natural products. 2011 Oct; 74(10):2069-80. doi: 10.1021/np2002918. [PMID: 21973054]
  • Yuan-Chuen Wang, Wan-Yu Li, Deng-Chyang Wu, Jeh-Jeng Wang, Cheng-Hsun Wu, Jyun-Ji Liao, Cheng-Kun Lin. In Vitro Activity of 2-methoxy-1,4-naphthoquinone and Stigmasta-7,22-diene-3β-ol from Impatiens balsamina L. against Multiple Antibiotic-Resistant Helicobacter pylori. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):704721. doi: 10.1093/ecam/nep147. [PMID: 19773391]
  • Naomi Mori, Kazufumi Toume, Midori A Arai, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi. 2-methoxy-1,4-naphthoquinone isolated from Impatiens balsamina in a screening program for activity to inhibit Wnt signaling. Journal of natural medicines. 2011 Jan; 65(1):234-6. doi: 10.1007/s11418-010-0471-0. [PMID: 20886301]
  • Zhi-Shan Ding, Fu-Sheng Jiang, Ni-Pi Chen, Gui-Yuan Lv, Cheng-Gang Zhu. Isolation and identification of an anti-tumor component from leaves of Impatiens balsamina. Molecules (Basel, Switzerland). 2008 Jan; 13(2):220-9. doi: 10.3390/molecules13020220. [PMID: 18305414]
  • Martin J Mitchell, Aaron I Brescia, Stan L Smith, E David Morgan. Effects of the compounds 2-methoxynaphthoquinone, 2-propoxynaphthoquinone, and 2-isopropoxynaphthoquinone on ecdysone 20-monooxygenase activity. Archives of insect biochemistry and physiology. 2007 Sep; 66(1):45-52. doi: 10.1002/arch.20196. [PMID: 17694563]
  • Rex Munday, Barry L Smith, Christine M Munday. Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone. Journal of applied toxicology : JAT. 2007 May; 27(3):262-9. doi: 10.1002/jat.1206. [PMID: 17265417]
  • X Yang, D K Summerhurst, S F Koval, C Ficker, M L Smith, M A Bernards. Isolation of an antimicrobial compound from Impatiens balsamina L. using bioassay-guided fractionation. Phytotherapy research : PTR. 2001 Dec; 15(8):676-80. doi: 10.1002/ptr.906. [PMID: 11746859]
  • K Ishiguro, Y Ohira, H Oku. Antipruritic dinaphthofuran-7,12-dione derivatives from the pericarp of Impatiens balsamina. Journal of natural products. 1998 Sep; 61(9):1126-9. doi: 10.1021/np9704718. [PMID: 9748380]
  • S Rodriguez, J L Wolfender, E Hakizamungu, K Hostettmann. An antifungal naphthoquinone, xanthones and secoiridoids from Swertia calycina. Planta medica. 1995 Aug; 61(4):362-4. doi: 10.1055/s-2006-958102. [PMID: 7480185]