Juglone (BioDeep_00000000449)
Secondary id: BioDeep_00000867266
human metabolite PANOMIX_OTCML-2023 Endogenous
描述信息
Juglone is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities. It has a role as a herbicide, a reactive oxygen species generator and a geroprotector.
Juglone is a natural product found in Talaromyces diversus, Carya alba, and other organisms with data available.
Occurs in Juglans subspecies and pecan nuts (Carya illinoensis). Juglone is found in many foods, some of which are common walnut, liquor, black walnut, and nuts.
Juglone is found in black walnut. Juglone occurs in Juglans species and pecan nuts (Carya illinoensis
D000074385 - Food Ingredients > D005503 - Food Additives > D005520 - Food Preservatives
D009676 - Noxae > D003603 - Cytotoxins
D000970 - Antineoplastic Agents
D004791 - Enzyme Inhibitors
同义名列表
75 个代谢物同义名
InChI=1/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12; 4-08-00-02368 (Beilstein Handbook Reference); 1,4-dihydro-1,4-dioxo-5-hydroxynaphthalene; 5-hydroxy-1,4-dihydronaphthalene-1,4-dione; 5-Hydroxy-1,4-naphthalenedione, 9CI; 5-Hydroxy-1,4-naphthoquinone, 97\\%; 5-Hydroxy-1,4-naftochinon [Czech]; 1,4-NAPHTHALENEDIONE, 5-HYDROXY-; 5-Hydroxy-1,4-naphthosemiquinone; 5-hydroxy-naphthalene-1,4-dione; 5-hydroxy-1,4-naphthoquinone, 4; 1,4-Naphthoquinone, 8-hydroxy-; 5-Hydroxy-1,4-naphthalenedione; 5-Hydroxynaphthalene-1,4-dione; 1,4-Naphthoquinone, 5-hydroxy-; 8-Hydroxy-1,4-naphthalenedione; 5-Hydroxy-[1,4]Naphthoquinone; -Hydroxy-1,4-naphthalenedione; 8-Hydroxy-1,4-naphthoquinone; 5-hydroxy-1,4-naphthoquinone; 5-Hydroxy-p-naphthoquinone; 5-Hydroxy-1,4-naftochinon; 5-Hydroxynaphthoquinone; JUGLONE CRYSTALLIZED; C.I. Natural Brown 7; WLN: L66 BV EVJ GQ; Spectrum5_000357; Spectrum2_000778; Spectrum4_001769; Spectrum3_001228; UNII-W6Q80SK9L6; walnut extract; Antibiotic PD7; 1, 8-hydroxy-; DivK1c_001026; KBio1_001026; KBio2_003463; KBio3_000914; KBio2_005038; KBio3_002948; KBio2_006031; KBio2_002470; KBio2_007606; JUGLONE [MI]; KBio2_005633; KBio2_000895; KBio3_000913; KBio2_000497; KBio3_002176; KBio2_003065; IDI1_001026; IDI1_002164; SMP1_000168; Bio2_000409; Bio1_001419; Bio1_000441; Bio2_000889; Bio1_000930; W6Q80SK9L6; CI 75500; Regianin; Juglone; Jugnlon; Juglane; Lawsone; Yuglon; Juglon; Iuglon; Akhnot; 5-HNQ; Nucin; 3b7j; PD7; Juglone; Juglone
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:15794
- KEGG: C03840
- PubChem: 3806
- HMDB: HMDB0030773
- Metlin: METLIN44061
- ChEMBL: CHEMBL43612
- Wikipedia: Juglone
- MeSH: juglone
- ChemIDplus: 0000481390
- MetaCyc: HYDROXYNAPHTHOQUINONE
- KNApSAcK: C00000144
- foodb: FDB002708
- chemspider: 3674
- CAS: 481-39-0
- CAS: 481-13-0
- medchemexpress: HY-N6949
- PMhub: MS000011188
- PubChem: 6579
- PDB-CCD: JUG
- 3DMET: B00645
- NIKKAJI: J5.777K
- RefMet: Juglone
- KNApSAcK: 15794
- LOTUS: LTS0110862
- wikidata: Q900912
分类词条
相关代谢途径
Reactome(0)
BioCyc(5)
PlantCyc(4)
代谢反应
3 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(2)
- juglone biosynthesis:
1,4-naphthoquinone + A(H2) + O2 ⟶ A + H2O + juglone - juglone degradation:
3,5-dihydroxy-1,4-naphthoquinol + H2O + O2 ⟶ 2,3-dihydroxybenzoate + H+ + pyruvate
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(1)
- juglone biosynthesis:
1,4-dihydroxy-2-naphthoate + A + H+ ⟶ 1,4-naphthoquinone + A(H2) + CO2
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
20 个相关的物种来源信息
- 483143 - Biancaea sappan: 10.1007/978-1-4020-4585-1_2417
- 53846 - Caesalpinia pulcherrima: 10.1007/978-1-4020-4585-1_2417
- 1620028 - Carya alba: 10.1021/JF60221A027
- 32201 - Carya illinoinensis:
- 60418 - Carya ovata: 10.1021/JF60221A027
- 91227 - Carya tomentosa: 10.1021/JF60221A027
- 173410 - Drosera madagascariensis:
- 85202 - Euclea natalensis: 10.1248/BPB.31.1429
- 9606 - Homo sapiens: -
- 16714 - Juglandaceae: 10.1016/J.BBRC.2015.04.124
- 16718 - Juglans: 10.1016/J.FCT.2012.01.002
- 91213 - Juglans cathayensis: 10.1080/10286020.2011.575365
- 91218 - Juglans mandshurica:
- 16719 - Juglans nigra:
- 51240 - Juglans regia:
- 321550 - Libidibia coriaria: 10.1007/978-1-4020-4585-1_2417
- 85252 - Pterocarya fraxinifolia: 10.1016/0031-9422(73)80528-X
- 16723 - Pterocarya rhoifolia: 10.1016/S0031-9422(00)81321-7
- 66424 - Streptomyces hiroshimensis: 10.1007/BF02238336
- 128434 - Talaromyces diversus: 10.1248/CPB.34.1497
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
- Nina V Terletskaya, Elvira A Shadenova, Yuliya A Litvinenko, Kazhybek Ashimuly, Malika Erbay, Aigerim Mamirova, Irada Nazarova, Nataliya D Meduntseva, Nataliya O Kudrina, Nazym K Korbozova, Erika D Djangalina. Influence of Cold Stress on Physiological and Phytochemical Characteristics and Secondary Metabolite Accumulation in Microclones of Juglans regia L.
International journal of molecular sciences.
2024 May; 25(9):. doi:
10.3390/ijms25094991. [PMID: 38732208] - Yukie Akutsu, Takaaki Fujiwara, Rintaro Suzuki, Yuki Nishigaya, Toshimasa Yamazaki. Juglone, a plant-derived 1,4-naphthoquinone, binds to hydroxylamine oxidoreductase and inhibits the electron transfer to cytochrome c554.
Applied and environmental microbiology.
2023 Dec; 89(12):e0129123. doi:
10.1128/aem.01291-23. [PMID: 38009977] - Pei-Ling Yen, Ting-An Lin, Wei Lin Chuah, Chih-Yi Chang, Yen-Hsueh Tseng, Chia-Yin Huang, Jeng-Chuann Yang, Fu-Lan Hsu, Vivian Hsiu-Chuan Liao. Methanol Extracts from Cirsium japonicum DC. var. australe Kitam. and Their Active Components Reduce Intracellular Oxidative Stress in Caenorhabditis elegans.
Molecules (Basel, Switzerland).
2023 Oct; 28(19):. doi:
10.3390/molecules28196923. [PMID: 37836767] - Sara Thabit, Heba Handoussa, Nesrine S ElSayed, Hans-Georg Breitinger, Ulrike Breitinger, Michael Wink. A fruit extract of Styphnolobium japonicum (L.) counteracts oxidative stress and mediates neuroprotection in Caenorhabditis elegans.
BMC complementary medicine and therapies.
2023 Sep; 23(1):330. doi:
10.1186/s12906-023-04149-8. [PMID: 37726773] - Leeladarshini Sujeeun, Sean C Thomas. Biochar mitigates allelopathic effects in temperate trees.
Ecological applications : a publication of the Ecological Society of America.
2023 06; 33(4):e2832. doi:
10.1002/eap.2832. [PMID: 36864680] - Kaihua Wang, Beibei Wang, Henan Ma, Ziwen Wang, Yuxiu Liu, Qingmin Wang. Natural Products for Pesticides Discovery: Structural Diversity Derivation and Biological Activities of Naphthoquinones Plumbagin and Juglone.
Molecules (Basel, Switzerland).
2023 Apr; 28(8):. doi:
10.3390/molecules28083328. [PMID: 37110562] - Weijia Chen, Lei He, Hongyan Pei, Jianming Li, Yan Zhao, Ying Zong, Hong Kan, Zhongmei He, Rui Du. Neuroprotective effect of total flavonoids in stems and leaves of Glycyrrhiza uralensis Fisch. on oxidative stress in HT-22 cells and Caenorhabditis elegans.
Aging.
2023 Apr; 15(12):5290-5303. doi:
10.18632/aging.204627. [PMID: 37367832] - 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] - Wu-Heng Yue, Lan-Qun Qin, Juan Cai, Rui Mei, Han-Qing Qian, Zheng-Yun Zou. Jug-PLGA-NPs, a New Form of Juglone with Enhanced Efficiency and Reduced Toxicity on Melanoma.
Chinese journal of integrative medicine.
2022 Oct; 28(10):909-917. doi:
10.1007/s11655-021-3461-y. [PMID: 34913148] - Xiang Li, Kewei Cai, Qinhui Zhang, Xiaona Pei, Song Chen, Luping Jiang, Zhiming Han, Minghui Zhao, Yan Li, Xinxin Zhang, Yuxi Li, Shikai Zhang, Su Chen, Guanzheng Qu, Mulualem Tigabu, Vincent L Chiang, Ronald Sederoff, Xiyang Zhao. The Manchurian Walnut Genome: Insights into Juglone and Lipid Biosynthesis.
GigaScience.
2022 06; 11(?):. doi:
10.1093/gigascience/giac057. [PMID: 35764602] - Muhammad Furqan, Alishba Fayyaz, Farhat Firdous, Hadeeqa Raza, Aishah Bilal, Rahman Shah Zaib Saleem, Syed Shahzad-Ul-Hussan, Daijie Wang, Fadia S Youssef, Nawal M Al Musayeib, Mohamed L Ashour, Hidayat Hussain, Amir Faisal. Identification and Characterization of Natural and Semisynthetic Quinones as Aurora Kinase Inhibitors.
Journal of natural products.
2022 06; 85(6):1503-1513. doi:
10.1021/acs.jnatprod.1c01222. [PMID: 35687347] - Yu Ting Tang, Yang Li, Peng Chu, Xiao Dong Ma, Ze Yao Tang, Zhao Lin Sun. Molecular biological mechanism of action in cancer therapies: Juglone and its derivatives, the future of development.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2022 Apr; 148(?):112785. doi:
10.1016/j.biopha.2022.112785. [PMID: 35272138] - Jialei Mao, Yinzhu Bian, Qun Zhang, Linghui Kong, Xiao Shi, Jing Hu, Mi Yang, Li Li, Hanqing Qian, Baorui Liu, Xiaoping Qian. Antitumor activity of iRGD-modified red blood cell membrane nanoparticles loaded with Juglone and Oxaliplatin against colorectal cancer.
Journal of biomaterials applications.
2022 02; 36(7):1301-1316. doi:
10.1177/08853282211052386. [PMID: 34802305] - Falak Niaz, Muhammad Faheem, Mutiullah Khattak, Iqra Anam Khawaja, Mi-Jeong Ahn, Umakanta Sarker, Syed Babar Jamal, Riaz Ullah, Atif Ali Khan Khalil. Antibacterial and Antibiofilm Activity of Juglone Derivatives against Enterococcus faecalis: An In Silico and In Vitro Approach.
BioMed research international.
2022; 2022(?):6197375. doi:
10.1155/2022/6197375. [PMID: 36408282] - Qiqi Han, Luoluo Feng, Yani Zhang, Runguang Zhang, Guoliang Wang, Youlin Zhang. Effect of Juglone against Pseudomonas syringae pv Actinidiae Planktonic Growth and Biofilm Formation.
Molecules (Basel, Switzerland).
2021 Dec; 26(24):. doi:
10.3390/molecules26247580. [PMID: 34946659] - Jiahua Cui, Jinping Jia. Discovery of juglone and its derivatives as potent SARS-CoV-2 main proteinase inhibitors.
European journal of medicinal chemistry.
2021 Dec; 225(?):113789. doi:
10.1016/j.ejmech.2021.113789. [PMID: 34438124] - Qiqi Han, Xinpeng Yan, Runguang Zhang, Guoliang Wang, Youlin Zhang. Juglone Inactivates Pseudomonas aeruginosa through Cell Membrane Damage, Biofilm Blockage, and Inhibition of Gene Expression.
Molecules (Basel, Switzerland).
2021 Sep; 26(19):. doi:
10.3390/molecules26195854. [PMID: 34641398] - Waseem-Ul- Arifeen, Fazal-Ur- Rehman, Shahid Adeel, Muhammad Zuber, Mirza Nadeem Ahmad, Tanvir Ahmad. Environmental friendly extraction of walnut bark-based juglone natural colorant for dyeing studies of wool fabric.
Environmental science and pollution research international.
2021 Sep; 28(36):49958-49966. doi:
10.1007/s11356-021-14277-8. [PMID: 33948834] - Yongzhi Hua, Ruiqi Liu, Min Lu, Xueneng Guan, Suyang Zhuang, Yaozhou Tian, Zhenhai Zhang, Li Cui. Juglone regulates gut microbiota and Th17/Treg balance in DSS-induced ulcerative colitis.
International immunopharmacology.
2021 Aug; 97(?):107683. doi:
10.1016/j.intimp.2021.107683. [PMID: 33915494] - Yuan-Yuan Zhang, Zhi-Jing Ni, Elnur Elam, Fan Zhang, Kiran Thakur, Shaoyun Wang, Jian-Guo Zhang, Zhao-Jun Wei. Juglone, a novel activator of ferroptosis, induces cell death in endometrial carcinoma Ishikawa cells.
Food & function.
2021 Jun; 12(11):4947-4959. doi:
10.1039/d1fo00790d. [PMID: 34100505] - Bolor Tsolmon, Yang Fang, Tao Yang, Ling Guo, Kaize He, Guo-You Li, Hai Zhao. Structural identification and UPLC-ESI-QTOF-MS2 analysis of flavonoids in the aquatic plant Landoltia punctata and their in vitro and in vivo antioxidant activities.
Food chemistry.
2021 May; 343(?):128392. doi:
10.1016/j.foodchem.2020.128392. [PMID: 33191012] - Alagesan Seetha, Halagowder Devaraj, Ganapasam Sudhandiran. Effects of combined treatment with Indomethacin and Juglone on AOM/DSS induced colon carcinogenesis in Balb/c mice: Roles of inflammation and apoptosis.
Life sciences.
2021 Jan; 264(?):118657. doi:
10.1016/j.lfs.2020.118657. [PMID: 33148421] - Xiaojie Zhao, Dan Wang, Shanshan Wan, Xiuheng Liu, Wei Wang, Lei Wang. The Suppression of Pin1-Alleviated Oxidative Stress through the p38 MAPK Pathway in Ischemia- and Reperfusion-Induced Acute Kidney Injury.
Oxidative medicine and cellular longevity.
2021; 2021(?):1313847. doi:
10.1155/2021/1313847. [PMID: 34373763] - Xue Zhang, Changyin Zhou, Wenxiu Cheng, Ruixin Tao, Hongxia Xu, Honglin Liu. Vitamin C protects early mouse embryos against juglone toxicity.
Reproductive toxicology (Elmsford, N.Y.).
2020 12; 98(?):200-208. doi:
10.1016/j.reprotox.2020.09.011. [PMID: 33010468] - Gisela A González-Montiel, Elizabeth N Kaweesa, Nicolas Feau, Richard C Hamelin, Jeffrey K Stone, Sandra Loesgen. Chemical, Bioactivity, and Biosynthetic Screening of Epiphytic Fungus Zasmidium pseudotsugae.
Molecules (Basel, Switzerland).
2020 May; 25(10):. doi:
10.3390/molecules25102358. [PMID: 32438585] - Jun-Yu Shi, Zhe Ren Huang, Hong Yan Gao, Xiao Li Xu. Anticancer effects of juglone in OVCAR-3 human ovarian carcinoma are facilitated through programmed cell death, endogenous ROS production, inhibition of cell migration and invasion and cell cycle arrest.
Journal of B.U.ON. : official journal of the Balkan Union of Oncology.
2020 Mar; 25(2):779-784. doi:
. [PMID: 32521867] - Fatemeh Abyar, Leila Tabrizi. Experimental and theoretical investigations of novel oxidovanadium(IV) juglone complex: DNA/HSA interaction and cytotoxic activity.
Journal of biomolecular structure & dynamics.
2020 02; 38(2):474-487. doi:
10.1080/07391102.2019.1580221. [PMID: 30831056] - Inés Reigada, Cristina Moliner, Marta Sofía Valero, David Weinkove, Elisa Langa, Carlota Gómez Rincón. Antioxidant and Antiaging Effects of Licorice on the Caenorhabditis elegans Model.
Journal of medicinal food.
2020 Jan; 23(1):72-78. doi:
10.1089/jmf.2019.0081. [PMID: 31545123] - Xue Zhang, Weijian Li, Xiaofan Sun, Juan Li, Wangjun Wu, Honglin Liu. Vitamin C protects against defects induced by juglone during porcine oocyte maturation.
Journal of cellular physiology.
2019 11; 234(11):19574-19581. doi:
10.1002/jcp.28555. [PMID: 30980384] - Qin Yang, Qing-Shou Yao, Yi Kuang, Yue-Zhi Zhang, Ling-Ling Feng, Lu Zhang, Lin Guo, Ze-Ping Xie, Shu-Min Zhang. Antimicrobial and cytotoxic juglones from the immature exocarps of Juglans mandshurica.
Natural product research.
2019 Nov; 33(22):3203-3209. doi:
10.1080/14786419.2018.1468326. [PMID: 29726709] - Peng Wang, Sun-Dong Zhang, Jiao Jiao, Wei Wang, Liang Yu, Xue-Lian Zhao, Li-Tao Wang, Dong Meng, Yu-Jie Fu. ROS -mediated p53 activation by juglone enhances apoptosis and autophagy in vivo and in vitro.
Toxicology and applied pharmacology.
2019 09; 379(?):114647. doi:
10.1016/j.taap.2019.114647. [PMID: 31283929] - Panthakarn Rangsinth, Anchalee Prasansuklab, Chatrawee Duangjan, Xiaojie Gu, Krai Meemon, Michael Wink, Tewin Tencomnao. Leaf extract of Caesalpinia mimosoides enhances oxidative stress resistance and prolongs lifespan in Caenorhabditis elegans.
BMC complementary and alternative medicine.
2019 Jul; 19(1):164. doi:
10.1186/s12906-019-2578-5. [PMID: 31286949] - Yuan-Yuan Zhang, Fan Zhang, Ying-Shuo Zhang, Kiran Thakur, Jian-Guo Zhang, Yun Liu, Huan Kan, Zhao-Jun Wei. Mechanism of Juglone-Induced Cell Cycle Arrest and Apoptosis in Ishikawa Human Endometrial Cancer Cells.
Journal of agricultural and food chemistry.
2019 Jul; 67(26):7378-7389. doi:
10.1021/acs.jafc.9b02759. [PMID: 31184118] - Xin Fan, Huaiyu He, Jiao Li, Guoyong Luo, Yuanyuan Zheng, Jian-Kang Zhou, Juan He, Wenchen Pu, Yun Zhao. Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis.
Bioorganic & medicinal chemistry.
2019 06; 27(11):2235-2244. doi:
10.1016/j.bmc.2019.04.028. [PMID: 31027708] - Atif Ali Khan Khalil, Woo Sung Park, Jeehoon Lee, Hye-Jin Kim, Kazi-Marjahan Akter, Young-Min Goo, Ji-Yeong Bae, Man-Seog Chun, Jung-Hwan Kim, Mi-Jeong Ahn. A new anti-Helicobacter pylori juglone from Reynoutria japonica.
Archives of pharmacal research.
2019 Jun; 42(6):505-511. doi:
10.1007/s12272-019-01160-x. [PMID: 31073878] - Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11.
Chemico-biological interactions.
2019 May; 305(?):12-20. doi:
10.1016/j.cbi.2019.03.026. [PMID: 30926317] - Wuguo Li, Qing Zhang, Kaotan Chen, Zhenhua Sima, Jingli Liu, Qiang Yu, Jiawei Liu. 2-Ethoxystypandrone, a novel small-molecule STAT3 signaling inhibitor from Polygonum cuspidatum, inhibits cell growth and induces apoptosis of HCC cells and HCC Cancer stem cells.
BMC complementary and alternative medicine.
2019 Feb; 19(1):38. doi:
10.1186/s12906-019-2440-9. [PMID: 30709346] - Hubert Sytykiewicz, Agnieszka Kozak, Bogumił Leszczyński, Cezary Sempruch, Iwona Łukasik, Iwona Sprawka, Katarzyna Kmieć, Monika Kurowska, Aldona Kopczyńska, Paweł Czerniewicz. Transcriptional profiling of catalase genes in juglone-treated seeds of maize (Zea mays L.) and wheat (Triticum aestivum L.).
Acta biologica Hungarica.
2018 Dec; 69(4):449-463. doi:
10.1556/018.69.2018.4.7. [PMID: 30587016] - Andréia Limana Tambara, Liliana de Los Santos Moraes, Ana Helena Dal Forno, Jean Ramos Boldori, Ana Thalita Gonçalves Soares, Cristiane de Freitas Rodrigues, Lilian Regina Barros Mariutti, Adriana Zerlotti Mercadante, Daiana Silva de Ávila, Cristiane Casagrande Denardin. Purple pitanga fruit (Eugenia uniflora L.) protects against oxidative stress and increase the lifespan in Caenorhabditis elegans via the DAF-16/FOXO pathway.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2018 Oct; 120(?):639-650. doi:
10.1016/j.fct.2018.07.057. [PMID: 30077708] - Peng Wang, Chang Gao, Wei Wang, Li-Ping Yao, Jing Zhang, Sun-Dong Zhang, Ji Li, Shao-Hong Fang, Yu-Jie Fu. Juglone induces apoptosis and autophagy via modulation of mitogen-activated protein kinase pathways in human hepatocellular carcinoma cells.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2018 Jun; 116(Pt B):40-50. doi:
10.1016/j.fct.2018.04.004. [PMID: 29627502] - Alexandra G Durán, Nuria Chinchilla, José Mg Molinillo, Francisco A Macías. Influence of lipophilicity in O-acyl and O-alkyl derivatives of juglone and lawsone: a structure-activity relationship study in the search for natural herbicide models.
Pest management science.
2018 Mar; 74(3):682-694. doi:
10.1002/ps.4764. [PMID: 29024464] - Mansour Sobeh, Mona F Mahmoud, Mohamed A O Abdelfattah, Haroan Cheng, Assem M El-Shazly, Michael Wink. A proanthocyanidin-rich extract from Cassia abbreviata exhibits antioxidant and hepatoprotective activities in vivo.
Journal of ethnopharmacology.
2018 Mar; 213(?):38-47. doi:
10.1016/j.jep.2017.11.007. [PMID: 29126990] - Beatrycze Nowicka, Andrzej Żądło, Bartosz Pluciński, Jerzy Kruk, Paulina Kuczyńska. The oxidative stress in allelopathy: Participation of prenyllipid antioxidants in the response to juglone in Chlamydomonas reinhardtii.
Phytochemistry.
2017 Dec; 144(?):171-179. doi:
10.1016/j.phytochem.2017.09.012. [PMID: 28942064] - Mansour Sobeh, Mona F Mahmoud, Rehab A Hasan, Haroan Cheng, Assem M El-Shazly, Michael Wink. Senna singueana: Antioxidant, Hepatoprotective, Antiapoptotic Properties and Phytochemical Profiling of a Methanol Bark Extract.
Molecules (Basel, Switzerland).
2017 Sep; 22(9):. doi:
10.3390/molecules22091502. [PMID: 28885586] - Pan Zhao, Guihua Gao, Lianjun Zhang, Qianqian Cai, Nan Lu, Li Cheng, Shuaikang Li, Xiaohong Hou. Drug-protein binding mechanism of juglone for early pharmacokinetic profiling: Insights from ultrafiltration, multi-spectroscopic and molecular docking methods.
Journal of pharmaceutical and biomedical analysis.
2017 07; 141(?):262-269. doi:
10.1016/j.jpba.2017.03.036. [PMID: 28372900] - Ming Liu, Peng Yu, Hong Jiang, Xue Yang, Ji Zhao, Yunzeng Zou, Junbo Ge. The Essential Role of Pin1 via NF-κB Signaling in Vascular Inflammation and Atherosclerosis in ApoE-/- Mice.
International journal of molecular sciences.
2017 Mar; 18(3):. doi:
10.3390/ijms18030644. [PMID: 28300760] - D Wianowska, S Garbaczewska, A Cieniecka-Roslonkiewicz, A L Dawidowicz, A Jankowska. Comparison of antifungal activity of extracts from different Juglans regia cultivars and juglone.
Microbial pathogenesis.
2016 Nov; 100(?):263-267. doi:
10.1016/j.micpath.2016.10.009. [PMID: 27744101] - Xue Liu, Ershun Liang, Xiuhui Song, Zhanhui Du, Yun Zhang, Yuxia Zhao. Inhibition of Pin1 alleviates myocardial fibrosis and dysfunction in STZ-induced diabetic mice.
Biochemical and biophysical research communications.
2016 10; 479(1):109-15. doi:
10.1016/j.bbrc.2016.09.050. [PMID: 27634219] - Jiayi Wang, Yuhuan Cheng, Rina Wu, Donghua Jiang, Bing Bai, Dehong Tan, Tingcai Yan, Xiyun Sun, Qi Zhang, Zhaoxia Wu. Antibacterial Activity of Juglone against Staphylococcus aureus: From Apparent to Proteomic.
International journal of molecular sciences.
2016 Jun; 17(6):. doi:
10.3390/ijms17060965. [PMID: 27322260] - Jiayi Wang, Zixue Wang, Rina Wu, Donghua Jiang, Bing Bai, Dehong Tan, Tingcai Yan, Xiyun Sun, Qi Zhang, Zhaoxia Wu. Proteomic Analysis of the Antibacterial Mechanism of Action of Juglone against Staphylococcus aureus.
Natural product communications.
2016 Jun; 11(6):825-7. doi:
". [PMID: 27534127] - Roongpetch Keowkase, Natthida Weerapreeyakul. Cratoxylum formosum Extract Protects against Amyloid-Beta Toxicity in a Caenorhabditis elegans Model of Alzheimer's Disease.
Planta medica.
2016 Apr; 82(6):516-23. doi:
10.1055/s-0041-111621. [PMID: 26845710] - Soraya Sajadimajd, Razieh Yazdanparast, Fariba Roshanzamir. Augmentation of oxidative stress-induced apoptosis in MCF7 cells by ascorbate-tamoxifen and/or ascorbate-juglone treatments.
In vitro cellular & developmental biology. Animal.
2016 Feb; 52(2):193-203. doi:
10.1007/s11626-015-9961-4. [PMID: 26559067] - Serena Fiorito, Salvatore Genovese, Vito Alessandro Taddeo, Véronique Mathieu, Robert Kiss, Francesco Epifano. Novel juglone and plumbagin 5-O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells.
Bioorganic & medicinal chemistry letters.
2016 Jan; 26(2):334-337. doi:
10.1016/j.bmcl.2015.12.017. [PMID: 26706169] - Xue-Bang Zhang, Chang-Lin Zou, Yu-Xia Duan, Fang Wu, Gang Li. Activity guided isolation and modification of juglone from Juglans regia as potent cytotoxic agent against lung cancer cell lines.
BMC complementary and alternative medicine.
2015 Nov; 15(?):396. doi:
10.1186/s12906-015-0920-0. [PMID: 26530090] - Shan Su, Michael Wink. Natural lignans from Arctium lappa as antiaging agents in Caenorhabditis elegans.
Phytochemistry.
2015 Sep; 117(?):340-350. doi:
10.1016/j.phytochem.2015.06.021. [PMID: 26141518] - De-Jiang Zhou, Dong Mu, Ming-De Jiang, Shu-Mei Zheng, Yong Zhang, Sheng He, Min Weng, Wei-Zheng Zeng. Hepatoprotective effect of juglone on dimethylnitrosamine-induced liver fibrosis and its effect on hepatic antioxidant defence and the expression levels of α-SMA and collagen III.
Molecular medicine reports.
2015 Sep; 12(3):4095-4102. doi:
10.3892/mmr.2015.3992. [PMID: 26126609] - Irena Matławska, Wiesława Bylka, Ewa Widy-Tyszkiewicz, Beata Stanisz. Determination of the Juglone Content of Juglans regia Leaves by GC/MS.
Natural product communications.
2015 Jul; 10(7):1239-42. doi:
". [PMID: 26411020] - Therese Ellendorff, Reto Brun, Marcel Kaiser, Jandirk Sendker, Thomas J Schmidt. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.
Molecules (Basel, Switzerland).
2015 May; 20(6):10082-94. doi:
10.3390/molecules200610082. [PMID: 26035104] - Shailima R D Vardhini. Exploring the antiviral activity of juglone by computational method.
Journal of receptor and signal transduction research.
2014 Dec; 34(6):456-7. doi:
10.3109/10799893.2014.917325. [PMID: 24846583] - Petr Babula, Veronika Vaverkova, Zuzana Poborilova, Ludmila Ballova, Michal Masarik, Ivo Provaznik. Phytotoxic action of naphthoquinone juglone demonstrated on lettuce seedling roots.
Plant physiology and biochemistry : PPB.
2014 Nov; 84(?):78-86. doi:
10.1016/j.plaphy.2014.08.027. [PMID: 25240266] - Nian Xin, Murtaza Hasan, Wei Li, Yan Li. Juglans mandshurica Maxim extracts exhibit antitumor activity on HeLa cells in vitro.
Molecular medicine reports.
2014 Apr; 9(4):1313-8. doi:
10.3892/mmr.2014.1979. [PMID: 24566804] - Leila Rezaizadehnajafi, Michael Wink. EPs7630(®) from Pelargonium sidoides increases stress resistance in Caenorhabditis elegans probably via the DAF-16/FOXO pathway.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2014 Mar; 21(4):547-50. doi:
10.1016/j.phymed.2013.10.027. [PMID: 24252337] - Veronika Vaverkova, Oldrich Vrana, Vojtech Adam, Tomas Pekarek, Josef Jampilek, Petr Babula. The study of naphthoquinones and their complexes with DNA by using Raman spectroscopy and surface enhanced Raman spectroscopy: new insight into interactions of DNA with plant secondary metabolites.
BioMed research international.
2014; 2014(?):461393. doi:
10.1155/2014/461393. [PMID: 25045679] - Violeta Nour, Ion Trandafir, Sina Cosmulescu. HPLC determination of phenolic acids, flavonoids and juglone in walnut leaves.
Journal of chromatographic science.
2013 Oct; 51(9):883-90. doi:
10.1093/chromsci/bms180. [PMID: 23135132] - Huali Xu, Xiaofeng Yu, Shaochun Qu, Dayun Sui. Juglone, isolated from Juglans mandshurica Maxim, induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells.
Bioorganic & medicinal chemistry letters.
2013 Jun; 23(12):3631-4. doi:
10.1016/j.bmcl.2013.04.007. [PMID: 23643730] - Wei Chen, Leila Rezaizadehnajafi, Michael Wink. Influence of resveratrol on oxidative stress resistance and life span in Caenorhabditis elegans.
The Journal of pharmacy and pharmacology.
2013 May; 65(5):682-8. doi:
10.1111/jphp.12023. [PMID: 23600385] - Jin-Jian Lu, Jiao-Lin Bao, Guo-Sheng Wu, Wen-Shan Xu, Ming-Qing Huang, Xiu-Ping Chen, Yi-Tao Wang. Quinones derived from plant secondary metabolites as anti-cancer agents.
Anti-cancer agents in medicinal chemistry.
2013 Mar; 13(3):456-63. doi:
. [PMID: 22931417] - Wei Chen, Ikhwan Resmala Sudji, Erjia Wang, Elizabeth Joubert, Ben-Erik van Wyk, Michael Wink. Ameliorative effect of aspalathin from rooibos (Aspalathus linearis) on acute oxidative stress in Caenorhabditis elegans.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2013 Feb; 20(3-4):380-6. doi:
10.1016/j.phymed.2012.10.006. [PMID: 23218401] - Thilo Christopher Fischer, Christian Gosch, Beate Mirbeth, Markus Gselmann, Veronika Thallmair, Karl Stich. Potent and specific bactericidal effect of juglone (5-hydroxy-1,4-naphthoquinone) on the fire blight pathogen Erwinia amylovora.
Journal of agricultural and food chemistry.
2012 Dec; 60(49):12074-81. doi:
10.1021/jf303584r. [PMID: 23163769] - Jian-Jun Luo, Ben Yang, Yong Zeng, Chong Li. [Chemical constituents from the flower of Juglans regia].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2012 Oct; 35(10):1614-6. doi:
". [PMID: 23627127] - Fu-Lan Hsu, Wen-Hsuan Li, Chan-Wei Yu, Yi-Chen Hsieh, Ying-Fei Yang, Jui-Tung Liu, Justin Shih, Yu-Ju Chu, Pei-Ling Yen, Shang-Tzen Chang, Vivian Hsiu-Chuan Liao. In vivo antioxidant activities of essential oils and their constituents from leaves of the Taiwanese Cinnamomum osmophloeum.
Journal of agricultural and food chemistry.
2012 Mar; 60(12):3092-7. doi:
10.1021/jf2045284. [PMID: 22380926] - Niladri Basu, Andrew Waye, Vance L Trudeau, John T Arnason. Extracts from hardwood trees used in commercial paper mills contain biologically active neurochemical disruptors.
The Science of the total environment.
2012 Jan; 414(?):205-9. doi:
10.1016/j.scitotenv.2011.10.061. [PMID: 22137476] - S Vargas, K Ndjoko Ioset, A-E Hay, J-R Ioset, S Wittlin, K Hostettmann. Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
Journal of pharmaceutical and biomedical analysis.
2011 Dec; 56(5):880-6. doi:
10.1016/j.jpba.2011.06.026. [PMID: 21872416] - Wen-Chang Chi, Shih-Feng Fu, Tsai-Lien Huang, Yun-An Chen, Chi-Cien Chen, Hao-Jen Huang. Identification of transcriptome profiles and signaling pathways for the allelochemical juglone in rice roots.
Plant molecular biology.
2011 Dec; 77(6):591-607. doi:
10.1007/s11103-011-9841-6. [PMID: 22065257] - Rafal Piskorski, Simon Ineichen, Silvia Dorn. Ability of the oriental fruit moth Grapholita molesta (Lepidoptera: Tortricidae) to detoxify juglone, the main secondary metabolite of the non-host plant walnut.
Journal of chemical ecology.
2011 Oct; 37(10):1110-6. doi:
10.1007/s10886-011-0015-4. [PMID: 21901444] - M R Sunil Kumar, B Kiran Aithal, N Udupa, M Sreenivasulu Reddy, V Raakesh, R S R Murthy, D Prudhvi Raju, B S Satish Rao. Formulation of plumbagin loaded long circulating pegylated liposomes: in vivo evaluation in C57BL/6J mice bearing B16F1 melanoma.
Drug delivery.
2011 Sep; 18(7):511-22. doi:
10.3109/10717544.2011.595840. [PMID: 21793763] - B Kiran Aithal, M R Sunil Kumar, B Nageshwar Rao, Raghavendra Upadhya, Vijendra Prabhu, Gopal Shavi, Karthik Arumugam, Shyama Prasad Sajankila, N Udupa, K Satyamoorthy, B S Satish Rao. Evaluation of pharmacokinetic, biodistribution, pharmacodynamic, and toxicity profile of free juglone and its sterically stabilized liposomes.
Journal of pharmaceutical sciences.
2011 Aug; 100(8):3517-3528. doi:
10.1002/jps.22573. [PMID: 21523783] - Rafal Piskorski, Silvia Dorn. How the oligophage codling moth Cydia pomonella survives on walnut despite its secondary metabolite juglone.
Journal of insect physiology.
2011 Jun; 57(6):744-50. doi:
10.1016/j.jinsphys.2011.02.014. [PMID: 21356213] - Hubert Sytykiewicz. Expression patterns of glutathione transferase gene (GstI) in maize seedlings under juglone-induced oxidative stress.
International journal of molecular sciences.
2011; 12(11):7982-95. doi:
10.3390/ijms12117982. [PMID: 22174645] - Sashka Boychova Krumova, Sergey Petrovich Laptenok, László Kovács, Tünde Tóth, Arie van Hoek, Gyozo Garab, Herbert van Amerongen. Digalactosyl-diacylglycerol-deficiency lowers the thermal stability of thylakoid membranes.
Photosynthesis research.
2010 Sep; 105(3):229-42. doi:
10.1007/s11120-010-9581-5. [PMID: 20645128] - S Abbas, M Wink. Epigallocatechin gallate inhibits beta amyloid oligomerization in Caenorhabditis elegans and affects the daf-2/insulin-like signaling pathway.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2010 Sep; 17(11):902-9. doi:
10.1016/j.phymed.2010.03.008. [PMID: 20382008] - Keiko Murakami, Miyako Haneda, Shouko Iwata, Masataka Yoshino. Effect of hydroxy substituent on the prooxidant action of naphthoquinone compounds.
Toxicology in vitro : an international journal published in association with BIBRA.
2010 Apr; 24(3):905-9. doi:
10.1016/j.tiv.2009.11.018. [PMID: 19961919] - Koichi Hasegawa, Satsuki Miwa, Kaname Tsutsumiuchi, Johji Miwa. Allyl isothiocyanate that induces GST and UGT expression confers oxidative stress resistance on C. elegans, as demonstrated by nematode biosensor.
PloS one.
2010 Feb; 5(2):e9267. doi:
10.1371/journal.pone.0009267. [PMID: 20174640] - Vladimir Chobot, Franz Hadacek. Iron and its complexation by phenolic cellular metabolites: from oxidative stress to chemical weapons.
Plant signaling & behavior.
2010 Jan; 5(1):4-8. doi:
10.4161/psb.5.1.10197. [PMID: 20592800] - Parisa Sadighara, Javad Ashrafihelan, Abbas Barin, Tahreh Ali Esfahani. Histopathology and cholinergic assessment of Pterocarya fraxinifolia on chicken embryo.
Interdisciplinary toxicology.
2009 Dec; 2(4):254-6. doi:
10.2478/v10102-009-0023-1. [PMID: 21217863] - Morris Nechama, Takafumi Uchida, Irit Mor Yosef-Levi, Justin Silver, Tally Naveh-Many. The peptidyl-prolyl isomerase Pin1 determines parathyroid hormone mRNA levels and stability in rat models of secondary hyperparathyroidism.
The Journal of clinical investigation.
2009 Oct; 119(10):3102-14. doi:
10.1172/jci39522. [PMID: 19770516] - Vladimir Chobot, Christoph Huber, Guenter Trettenhahn, Franz Hadacek. (+/-)-catechin: chemical weapon, antioxidant, or stress regulator?.
Journal of chemical ecology.
2009 Aug; 35(8):980-96. doi:
10.1007/s10886-009-9681-x. [PMID: 19701725] - S-H Kim, G-B Cai, Y-A Bae, E-G Lee, Y-S Lee, Y Kong. Two novel phospholipid hydroperoxide glutathione peroxidase genes of Paragonimus westermani induced by oxidative stress.
Parasitology.
2009 Apr; 136(5):553-65. doi:
10.1017/s0031182009005654. [PMID: 19265561] - Itsuko Fukuda, Atsushi Kaneko, Shin Nishiumi, Masaya Kawase, Rika Nishikiori, Nobuhide Fujitake, Hitoshi Ashida. Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
Journal of bioscience and bioengineering.
2009 Mar; 107(3):296-300. doi:
10.1016/j.jbiosc.2008.10.008. [PMID: 19269596] - V Chobot, F Hadacek. Milieu-dependent pro- and antioxidant activity of juglone may explain linear and nonlinear effects on seedling development.
Journal of chemical ecology.
2009 Mar; 35(3):383-90. doi:
10.1007/s10886-009-9609-5. [PMID: 19263168] - Mo-Long Sun, Zhan-Qian Song, Gui-Zhen Fang. [Insecticidal activity and active components of alcohol extract from Juglans mandshurica Maxim leaves].
Ying yong sheng tai xue bao = The journal of applied ecology.
2007 Dec; 18(12):2910-4. doi:
". [PMID: 18333475] - D A Wright, C L Mitchelmore, R Dawson, H G Cutler. The influence of water quality on the toxicity and degradation of juglone (5-hydroxy 1,4-naphthoquinone).
Environmental technology.
2007 Oct; 28(10):1091-101. doi:
10.1080/09593332808618873. [PMID: 17970515] - Guntram R von Kiparski, Linda S Lee, Andrew R Gillespie. Occurrence and fate of the phytotoxin juglone in alley soils under black walnut trees.
Journal of environmental quality.
2007 May; 36(3):709-17. doi:
10.2134/jeq2006.0231. [PMID: 17412906] - Henrik T Simonsen, Anne Adsersen, Louise Berthelsen, Søren B Christensen, Alfonso Guzmán, Per Mølgaard. Ethnopharmacological evaluation of radal (leaves of Lomatia hirsuta) and isolation of 2-methoxyjuglone.
BMC complementary and alternative medicine.
2006 Aug; 6(?):29. doi:
10.1186/1472-6882-6-29. [PMID: 16945129] - Byeoung-Soo Park, Hyun-Kyung Lee, Sung-Eun Lee, Xiang-Lan Piao, Gary R Takeoka, Rosalind Y Wong, Young-Joon Ahn, Jeong-Han Kim. Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori.
Journal of ethnopharmacology.
2006 Apr; 105(1-2):255-62. doi:
10.1016/j.jep.2005.11.005. [PMID: 16359837] - L-J Chen, E H Lebetkin, L T Burka. Metabolism and disposition of juglone in male F344 rats.
Xenobiotica; the fate of foreign compounds in biological systems.
2005 Oct; 35(10-11):1019-34. doi:
10.1080/00498250500356621. [PMID: 16393859] - A Neamatallah, L Yan, S J Dewar, B Austin. An extract from teak (Tectona grandis) bark inhibited Listeria monocytogenes and methicillin resistant Staphylococcus aureus.
Letters in applied microbiology.
2005; 41(1):94-6. doi:
10.1111/j.1472-765x.2005.01680.x. [PMID: 15960759] - Stefan Kepinski, Ottoline Leyser. Auxin-induced SCFTIR1-Aux/IAA interaction involves stable modification of the SCFTIR1 complex.
Proceedings of the National Academy of Sciences of the United States of America.
2004 Aug; 101(33):12381-6. doi:
10.1073/pnas.0402868101. [PMID: 15295098] - Angela M Hejl, Karen L Koster. Juglone disrupts root plasma membrane H+-ATPase activity and impairs water uptake, root respiration, and growth in soybean (Glycine max) and corn (Zea mays).
Journal of chemical ecology.
2004 Feb; 30(2):453-71. doi:
10.1023/b:joec.0000017988.20530.d5. [PMID: 15112735]
