1,4-Naphthoquinone (BioDeep_00000000301)
Secondary id: BioDeep_00000017294
human metabolite blood metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds
代谢物信息卡片
1,4-Dihydro-1,4-diketonaphthalene
化学式: C10H6O2 (158.0367776)
中文名称: 1,4-萘醌
谱图信息:
最多检出来源 Homo sapiens(blood) 0.07%
分子结构信息
SMILES: C1=CC=C2C(=O)C=CC(=O)C2=C1
InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
描述信息
1,4-naphtoquinone, also known as 1,4-naphthalenedione or 1,4-dihydro-1,4-diketonaphthalene, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 1,4-naphtoquinone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1,4-naphtoquinone can be synthesized from naphthalene. 1,4-naphtoquinone is also a parent compound for other transformation products, including but not limited to, 2,3-dimethoxynaphthalene-1,4-dione, alisiaquinone A, and 1,4-naphthoquinone-2-carboxylic acid. 1,4-naphtoquinone can be found in liquor, which makes 1,4-naphtoquinone a potential biomarker for the consumption of this food product. 1,4-naphtoquinone is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CONFIDENCE standard compound; INTERNAL_ID 18
1,4-Naphthoquinone is a potential pharmacophore for inhibition of both MAO (monoamine oxidase) and DNA topoisomerase activities, this latter associated with antitumor activity[1].
同义名列表
15 个代谢物同义名
1,4-Dihydro-1,4-diketonaphthalene; 1,4-dihydronaphthalene-1,4-dione; 1,4-naphthalene-dione; 1,4-Naphthalenedione; alpha-Naphthoquinone; 1,4-Naphthoquinone; [1,4]Naphthoquinon; 1,4-naphtoquinone; Α-naphthoquinone; a-naphthoquinone; p-Naphthoquinone; NAPHTHOQUINONE; Succivil; 1,4-NQ; 1,4-Naphthoquinone
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:27418
- KEGG: C02617
- KEGGdrug: D70977
- PubChem: 8530
- HMDB: HMDB0244221
- Metlin: METLIN65798
- ChEMBL: CHEMBL55934
- MetaCyc: CPD0-954
- foodb: FDB000340
- chemspider: 8215
- CAS: 130-15-4
- MoNA: UA001803
- MoNA: UA001805
- PMhub: MS000010698
- PubChem: 5602
- NIKKAJI: J5.430E
- RefMet: Naphthoquinone
- medchemexpress: HY-W015490
- KNApSAcK: 27418
- HERB: HBIN001534
- LOTUS: LTS0176662
- wikidata: Q161542
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
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)
4 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 16719 - Juglans nigra: 10.1016/S0031-9422(00)98092-0
- 51240 - Juglans regia:
- 141191 - Lawsonia inermis: -
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
- 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] - Tatyana N Goleva, Konstantin G Lyamzaev, Anton G Rogov, Ljudmila S Khailova, Khoren K Epremyan, Galina P Shumakovich, Lidia V Domnina, Olga Yu Ivanova, Natalia V Marmiy, Tatiana V Zinevich, Dmitry S Esipov, Renata A Zvyagilskaya, Vladimir P Skulachev, Boris V Chernyak. Mitochondria-targeted 1,4-naphthoquinone (SkQN) is a powerful prooxidant and cytotoxic agent.
Biochimica et biophysica acta. Bioenergetics.
2020 08; 1861(8):148210. doi:
10.1016/j.bbabio.2020.148210. [PMID: 32305410] - Daiva Majiene, Jolita Kuseliauskyte, Arturas Stimbirys, Aiste Jekabsone. Comparison of the Effect of Native 1,4-Naphthoquinones Plumbagin, Menadione, and Lawsone on Viability, Redox Status, and Mitochondrial Functions of C6 Glioblastoma Cells.
Nutrients.
2019 Jun; 11(6):. doi:
10.3390/nu11061294. [PMID: 31181639] - 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] - Małgorzata Rudnicka, Michał Ludynia, Waldemar Karcz. Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments.
International journal of molecular sciences.
2019 Apr; 20(7):. doi:
10.3390/ijms20071788. [PMID: 30978914] - Palanisamy Ravichandiran, Sivakumar Allur Subramaniyan, Seon-Young Kim, Jong-Soo Kim, Byung-Hyun Park, Kwan Seob Shim, Dong Jin Yoo. Synthesis and Anticancer Evaluation of 1,4-Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety.
ChemMedChem.
2019 03; 14(5):532-544. doi:
10.1002/cmdc.201800749. [PMID: 30600915] - Pierluigi Reveglia, Sandra Savocchia, Regina Billones-Baaijens, Marco Masi, Alessio Cimmino, Antonio Evidente. Diploquinones A and B, Two New Phytotoxic Tetrasubstituted 1,4-Naphthoquinones from Diplodia mutila, a Causal Agent of Grapevine Trunk Disease.
Journal of agricultural and food chemistry.
2018 Nov; 66(45):11968-11973. doi:
10.1021/acs.jafc.8b05004. [PMID: 30360617] - Luciana Romão, Vanessa P do Canto, Paulo A Netz, Vivaldo Moura-Neto, Ângelo C Pinto, Cristian Follmer. Conjugation with polyamines enhances the antitumor activity of naphthoquinones against human glioblastoma cells.
Anti-cancer drugs.
2018 07; 29(6):520-529. doi:
10.1097/cad.0000000000000619. [PMID: 29561308] - Débora Vasconcelos Costa Mendonça, Daniela Pagliara Lage, Stephane Lima Calixto, Flaviano Melo Ottoni, Grasiele de Sousa Vieira Tavares, Fernanda Ludolf, Miguel Angel Chávez-Fumagalli, Mônica Santos Schneider, Mariana Costa Duarte, Carlos Alberto Pereira Tavares, Ricardo José Alves, Elaine Soares Coimbra, Eduardo Antonio Ferraz Coelho. Antileishmanial activity of a naphthoquinone derivate against promastigote and amastigote stages of Leishmania infantum and Leishmania amazonensis and its mechanism of action against L. amazonensis species.
Parasitology research.
2018 Feb; 117(2):391-403. doi:
10.1007/s00436-017-5713-6. [PMID: 29248978] - Chang Su, Dongjian Zhang, Na Bao, Aiyan Ji, Yuanbo Feng, Li Chen, Yicheng Ni, Jian Zhang, Zhiqi Yin. Evaluation of Radioiodinated 1,4-Naphthoquinones as Necrosis Avid Agents for Rapid Myocardium Necrosis Imaging.
Molecular imaging and biology.
2018 02; 20(1):74-84. doi:
10.1007/s11307-017-1089-3. [PMID: 28470585] - Javier Palacios, José Miguel Fonseca, Fernando Ayavire, Felipe Salas, Mirko Ortiz, Juan Marcelo Sandoval, Julio Benites, Chukwuemeka R Nwokocha, Ewaldo Zavala, Adrián Paredes, Iván Barría, José Luis Vega, Fredi Cifuentes. Ascorbate Attenuates Oxidative Stress and Increased Blood Pressure Induced by 2-(4-Hydroxyphenyl) Amino-1,4-naphthoquinone in Rats.
Oxidative medicine and cellular longevity.
2018; 2018(?):8989676. doi:
10.1155/2018/8989676. [PMID: 30147836] - Long Cheng, Yan He, Yun Tian, Biyun Liu, Yongyuan Zhang, Qiaohong Zhou, Zhenbin Wu. Comparative biotoxicity of N-Phenyl-1-naphthylamine and N-Phenyl-2-naphthylamine on cyanobacteria Microcystis aeruginosa.
Chemosphere.
2017 Jun; 176(?):183-191. doi:
10.1016/j.chemosphere.2017.02.110. [PMID: 28260658] - Jia Wang, Guangzhi Zeng, Xiaobing Huang, Zhe Wang, Ninghua Tan. 1,4-Naphthoquinone Triggers Nematode Lethality by Inducing Oxidative Stress and Activating Insulin/IGF Signaling Pathway in Caenorhabditis elegans.
Molecules (Basel, Switzerland).
2017 May; 22(5):. doi:
10.3390/molecules22050798. [PMID: 28505088] - Jie Kang, Peng Zhang, Zengping Gao, Jian Zhang, Zheng Yan, Hongqing Wang, Ruoyun Chen. Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53.
Phytochemistry.
2016 Oct; 130(?):144-51. doi:
10.1016/j.phytochem.2016.04.001. [PMID: 27298278] - Navneet Kishore, Brigitte Binneman, Anita Mahapatra, Maryna van de Venter, Debbie du Plessis-Stoman, Gerhardt Boukes, Peter Houghton, J J Marion Meyer, Namrita Lall. Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines.
Bioorganic & medicinal chemistry.
2014 Sep; 22(17):5013-9. doi:
10.1016/j.bmc.2014.06.013. [PMID: 25059501] - Che Lin, Dar-Ren Chen, Shu-Li Wang, Wei-Chung Hsieh, Wen-Fa Yu, Tzu-Wen Wang, Chen-His Tsai, Hz-Han Wei, Ben-Jei Tsuang, Po-Hsiung Lin. Cumulative body burdens of polycyclic aromatic hydrocarbons associated with estrogen bioactivation in pregnant women: protein adducts as biomarkers of exposure.
Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.
2014; 49(6):634-40. doi:
10.1080/10934529.2014.865416. [PMID: 24521408] - Nadia Hussein, Carla C Lopes, Paulo Castanho A Pernambuco Filho, Bruna R Carneiro, Luciano Caseli. Surface chemistry and spectroscopy studies on 1,4-naphthoquinone in cell membrane models using Langmuir monolayers.
Journal of colloid and interface science.
2013 Jul; 402(?):300-6. doi:
10.1016/j.jcis.2013.04.005. [PMID: 23664393] - Seetharaman Rajasekar, Da Jung Park, Cheol Park, Sejin Park, Young Hoon Park, Sun Tae Kim, Yung Hyun Choi, Young Whan Choi. In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma.
Journal of ethnopharmacology.
2012 Nov; 144(2):335-45. doi:
10.1016/j.jep.2012.09.017. [PMID: 22995444] - Mohamed Saleh Elgawish, Chikako Shimomai, Naoya Kishikawa, Kaname Ohyama, Kenichiro Nakashima, Naotaka Kuroda. Microplate analytical method for quinones by pulse photo-irradiation and chemiluminescence detection.
The Analyst.
2012 Oct; 137(20):4802-8. doi:
10.1039/c2an35353a. [PMID: 22910835] - Ho-Chen Wu, Ming-Jen Cheng, Chien-Fang Peng, Shyh-Chyun Yang, Hsun-Shuo Chang, Chu-Hung Lin, Chyi-Jia Wang, Ih-Sheng Chen. Secondary metabolites from the stems of Engelhardia roxburghiana and their antitubercular activities.
Phytochemistry.
2012 Oct; 82(?):118-27. doi:
10.1016/j.phytochem.2012.06.014. [PMID: 22818359] - So Young Gwon, Ji Yun Ahn, Chang Hwa Chung, BoKyung Moon, Tae Youl Ha. Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation.
Journal of agricultural and food chemistry.
2012 Sep; 60(36):9089-96. doi:
10.1021/jf3017404. [PMID: 22900585] - Joshua R Widhalm, Anne-Lise Ducluzeau, Nicole E Buller, Christian G Elowsky, Laura J Olsen, Gilles J C Basset. Phylloquinone (vitamin K(1) ) biosynthesis in plants: two peroxisomal thioesterases of Lactobacillales origin hydrolyze 1,4-dihydroxy-2-naphthoyl-CoA.
The Plant journal : for cell and molecular biology.
2012 Jul; 71(2):205-15. doi:
10.1111/j.1365-313x.2012.04972.x. [PMID: 22372525] - Paul A Egan, Frank van der Kooy. Coproduction and ecological significance of naphthoquinones in carnivorous sundews (Drosera).
Chemistry & biodiversity.
2012 Jun; 9(6):1033-44. doi:
10.1002/cbdv.201100274. [PMID: 22700223] - Duncan G G McMillan, Sophie J Marritt, Julea N Butt, Lars J C Jeuken. Menaquinone-7 is specific cofactor in tetraheme quinol dehydrogenase CymA.
The Journal of biological chemistry.
2012 Apr; 287(17):14215-25. doi:
10.1074/jbc.m112.348813. [PMID: 22393052] - Xueyan Fu, Judith Moreines, Sarah L Booth. Vitamin K supplementation does not prevent bone loss in ovariectomized Norway rats.
Nutrition & metabolism.
2012 Feb; 9(1):12. doi:
10.1186/1743-7075-9-12. [PMID: 22348311] - Jing Li, Lin Shen, Fu-rong Lu, You Qin, Rui Chen, Jia Li, Yan Li, Han-zi Zhan, Yuan-qiao He. Plumbagin inhibits cell growth and potentiates apoptosis in human gastric cancer cells in vitro through the NF-κB signaling pathway.
Acta pharmacologica Sinica.
2012 Feb; 33(2):242-9. doi:
10.1038/aps.2011.152. [PMID: 22231395] - James M Brimson, Sirikalaya J Brimson, Christopher A Brimson, Varaporn Rakkhitawatthana, Tewin Tencomnao. Rhinacanthus nasutus extracts prevent glutamate and amyloid-β neurotoxicity in HT-22 mouse hippocampal cells: possible active compounds include lupeol, stigmasterol and β-sitosterol.
International journal of molecular sciences.
2012; 13(4):5074-5097. doi:
10.3390/ijms13045074. [PMID: 22606031] - Hiromi Sato, Ryota Yamada, Midori Yanagihara, Hiroko Okuzawa, Hiroki Iwata, Ayako Kurosawa, Saki Ichinomiya, Rina Suzuki, Hiroyuki Okabe, Tomohiro Yano, Takuya Kumamoto, Noriyuki Suzuki, Tsutomu Ishikawa, Koichi Ueno. New 2-aryl-1,4-naphthoquinone-1-oxime methyl ether compound induces microtubule depolymerization and subsequent apoptosis.
Journal of pharmacological sciences.
2012; 118(4):467-78. doi:
10.1254/jphs.11229fp. [PMID: 22447301] - Tony Hadibarata, Abdull Rahim Mohd Yusoff, Azmi Aris, Risky Ayu Kristanti. Identification of naphthalene metabolism by white rot fungus Armillaria sp. F022.
Journal of environmental sciences (China).
2012; 24(4):728-32. doi:
10.1016/s1001-0742(11)60843-7. [PMID: 22894109] - Shin-ichiro Ozawa, Makiko Kosugi, Yasuhiro Kashino, Takashi Sugimura, Yuichiro Takahashi. 5'-monohydroxyphylloquinone is the dominant naphthoquinone of PSI in the green alga Chlamydomonas reinhardtii.
Plant & cell physiology.
2012 Jan; 53(1):237-43. doi:
10.1093/pcp/pcr168. [PMID: 22138100] - Benjamin Wiench, Tolga Eichhorn, Malte Paulsen, Thomas Efferth. Shikonin directly targets mitochondria and causes mitochondrial dysfunction in cancer cells.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):726025. doi:
10.1155/2012/726025. [PMID: 23118796] - Ali A Alshatwi, Tarique N Hasan, Gowhar Shafi, Naveed Ahmed Syed, Abdullah H Al-Assaf, Mohammed S Alamri, Abdrohman S Al-Khalifa. Validation of the Antiproliferative Effects of Organic Extracts from the Green Husk of Juglans regia L. on PC-3 Human Prostate Cancer Cells by Assessment of Apoptosis-Related Genes.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):103026. doi:
10.1155/2012/103026. [PMID: 22454652] - W F Costa, A B Oliveira, J C Nepomuceno. Lapachol as an epithelial tumor inhibitor agent in Drosophila melanogaster heterozygote for tumor suppressor gene wts.
Genetics and molecular research : GMR.
2011 Dec; 10(4):3236-45. doi:
10.4238/2011.december.22.1. [PMID: 22194187] - Ke Gong, Wenhua Li. Shikonin, a Chinese plant-derived naphthoquinone, induces apoptosis in hepatocellular carcinoma cells through reactive oxygen species: A potential new treatment for hepatocellular carcinoma.
Free radical biology & medicine.
2011 Dec; 51(12):2259-71. doi:
10.1016/j.freeradbiomed.2011.09.018. [PMID: 22011623] - Leonid R Ptitsyn, Kenzo Nomura, Ilya V Sklyar, Anna B Ravcheeva. The 1,4-naphthoquinone derivative from Pyrola rotundifolia activates AMPK phosphorylation in C2C12 myotubes.
Fitoterapia.
2011 Dec; 82(8):1285-9. doi:
10.1016/j.fitote.2011.09.005. [PMID: 21958969] - Anna Andolfi, Laura Mugnai, Jordi Luque, Giuseppe Surico, Alessio Cimmino, Antonio Evidente. Phytotoxins produced by fungi associated with grapevine trunk diseases.
Toxins.
2011 12; 3(12):1569-605. doi:
10.3390/toxins3121569. [PMID: 22295177] - Dianne Lim, Akihiro Ikeda, Kennedy K-T Vu, Kent T Yamaguchi, Tim R Tyner, Alam S Hasson. Method development for the measurement of quinone levels in urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Nov; 879(30):3592-8. doi:
10.1016/j.jchromb.2011.09.051. [PMID: 22024390] - Anna Kawiak, Aleksandra Królicka, Ewa Łojkowska. In vitro cultures of Drosera aliciae as a source of a cytotoxic naphthoquinone: ramentaceone.
Biotechnology letters.
2011 Nov; 33(11):2309-16. doi:
10.1007/s10529-011-0700-y. [PMID: 21761256] - Gopan Raj, Rajani Kurup, Abdul Azeez Hussain, Sabulal Baby. Distribution of naphthoquinones, plumbagin, droserone, and 5-O-methyl droserone in chitin-induced and uninduced Nepenthes khasiana: molecular events in prey capture.
Journal of experimental botany.
2011 Nov; 62(15):5429-36. doi:
10.1093/jxb/err219. [PMID: 21862483] - Priscila Batista Tessele, Franco Delle Monache, Nara Lins Meira Quintão, Gislaine Francieli da Silva, Lilian Wunsch Rocha, Greice M R S Lucena, Vania M M Ferreira, Rui D S Prediger, Valdir Cechinel Filho. A new naphthoquinone isolated from the bulbs of Cipura paludosa and pharmacological activity of two main constituents.
Planta medica.
2011 Jul; 77(10):1035-43. doi:
10.1055/s-0030-1250745. [PMID: 21283955] - Edézio Ferreira da Cunha-Júnior, Wallace Pacienza-Lima, Grazielle Alves Ribeiro, Chaquip Daher Netto, Marilene Marcuzzo do Canto-Cavalheiro, Alcides José Monteiro da Silva, Paulo Roberto Ribeiro Costa, Bartira Rossi-Bergmann, Eduardo Caio Torres-Santos. Effectiveness of the local or oral delivery of the novel naphthopterocarpanquinone LQB-118 against cutaneous leishmaniasis.
The Journal of antimicrobial chemotherapy.
2011 Jul; 66(7):1555-9. doi:
10.1093/jac/dkr158. [PMID: 21531758] - Kofi Annan, Nora Jackson, Rita A Dickson, George H Sam, Gustav Komlaga. Acaricidal effect of an isolate from Hoslundia opposita vahl against Amblyomma variegatum (Acari: Ixodidae).
Pharmacognosy research.
2011 Jul; 3(3):185-8. doi:
10.4103/0974-8490.85004. [PMID: 22022167] - Radava R Korać, Kapil M Khambholja. Potential of herbs in skin protection from ultraviolet radiation.
Pharmacognosy reviews.
2011 Jul; 5(10):164-73. doi:
10.4103/0973-7847.91114. [PMID: 22279374] - Pooi Yin Chung, Parasakthi Navaratnam, Lip Yong Chung. Synergistic antimicrobial activity between pentacyclic triterpenoids and antibiotics against Staphylococcus aureus strains.
Annals of clinical microbiology and antimicrobials.
2011 Jun; 10(?):25. doi:
10.1186/1476-0711-10-25. [PMID: 21658242] - Sabrina X Zhao, Wendy Weiwei Wang, Gregory S Walker, Liming Zhang, R Scott Obach. Metabolism of a dopamine receptor partial agonist in rats, including an unusual N-dearylation reaction.
Drug metabolism and pharmacokinetics.
2011 Jun; 26(3):266-79. doi:
10.2133/dmpk.dmpk-10-rg-109. [PMID: 21383524] - Toshio Furumoto, Arata Hoshikuma. Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture.
Phytochemistry.
2011 Jun; 72(9):871-4. doi:
10.1016/j.phytochem.2011.03.012. [PMID: 21511314] - Nilay Nandi, Tanmoy Bera, Sudeep Kumar, Bidyut Purkait, Ashish Kumar, Pradeep Das. Involvement of thermoplasmaquinone-7 in transplasma membrane electron transport of Entamoeba histolytica trophozoites: a key molecule for future rational chemotherapeutic drug designing.
Journal of bioenergetics and biomembranes.
2011 Apr; 43(2):203-15. doi:
10.1007/s10863-011-9347-6. [PMID: 21523408] - 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] - Timothy N C Wells. Natural products as starting points for future anti-malarial therapies: going back to our roots?.
Malaria journal.
2011 Mar; 10 Suppl 1(?):S3. doi:
10.1186/1475-2875-10-s1-s3. [PMID: 21411014] - Yoshiyuki Mizushina, Jun Maeda, Yasuhiro Irino, Masayuki Nishida, Shin Nishiumi, Yasuyuki Kondo, Kazuyuki Nishio, Kouji Kuramochi, Kazunori Tsubaki, Isoko Kuriyama, Takeshi Azuma, Hiromi Yoshida, Masaru Yoshida. Effects of intermediates between vitamins K(2) and K(3) on mammalian DNA polymerase inhibition and anti-inflammatory activity.
International journal of molecular sciences.
2011 Feb; 12(2):1115-32. doi:
10.3390/ijms12021115. [PMID: 21541047] - 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] - 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] - Anette I Öberg, Kamal Yassin, Robert I Csikasz, Nodi Dehvari, Irina G Shabalina, Dana S Hutchinson, Mona Wilcke, Claes-Göran Östenson, Tore Bengtsson. Shikonin increases glucose uptake in skeletal muscle cells and improves plasma glucose levels in diabetic Goto-Kakizaki rats.
PloS one.
2011; 6(7):e22510. doi:
10.1371/journal.pone.0022510. [PMID: 21818330] - Yan Jia, Ji Jing, Yang Bai, Zhen Li, Lande Liu, Jian Luo, Mingyao Liu, Huaqing Chen. Amelioration of experimental autoimmune encephalomyelitis by plumbagin through down-regulation of JAK-STAT and NF-κB signaling pathways.
PloS one.
2011; 6(10):e27006. doi:
10.1371/journal.pone.0027006. [PMID: 22066025] - Mingxiong Tan, Yancheng Liu, Xujian Luo, Zhenfeng Chen, Hong Liang. Antioxidant Activities of Plumbagin and Its Cu (II) Complex.
Bioinorganic chemistry and applications.
2011; 2011(?):898726. doi:
10.1155/2011/898726. [PMID: 22046145] - K Haghbeen, S Pourmolaei, M J Mareftjo, A Mousavi, K Akbari Noghabi, F Hosseini Shirazi, A Meshkat. Detailed investigations on the solid cell culture and antimicrobial activities of the Iranian Arnebia euchroma.
Journal of biomedicine & biotechnology.
2011; 2011(?):165852. doi:
10.1155/2011/165852. [PMID: 21772789] - Yusai Ito, Kenichi Onobori, Takeshi Yamazaki, Yoko Kawamura. Tigloylshikonin, a new minor Shikonin derivative, from the roots and the commercial root extract of lithospermum erythrorhizon.
Chemical & pharmaceutical bulletin.
2011; 59(1):117-9. doi:
10.1248/cpb.59.117. [PMID: 21212559] - Jin-e Yi, Bozena Obminska-Mrukowicz, Li-yun Yuan, Hui Yuan. Immunomodulatory effects of betulinic acid from the bark of white birch on mice.
Journal of veterinary science.
2010 Dec; 11(4):305-13. doi:
10.4142/jvs.2010.11.4.305. [PMID: 21113099] - Ravi S Singh, Rishi K Gara, Pardeep K Bhardwaj, Anish Kaachra, Sonia Malik, Ravi Kumar, Madhu Sharma, Paramvir S Ahuja, Sanjay Kumar. Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston].
BMC molecular biology.
2010 Nov; 11(?):88. doi:
10.1186/1471-2199-11-88. [PMID: 21092138] - 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] - M Matsubara, E Yamachika, H Tsujigiwa, N Mizukawa, T Ueno, J Murakami, N Ishida, Y Kaneda, N Shirasu, S Takagi. Suppressive effects of 1,4-dihydroxy-2-naphthoic acid administration on bone resorption.
Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA.
2010 Aug; 21(8):1437-47. doi:
10.1007/s00198-009-1075-y. [PMID: 19813044] - B Piro, Q D Zhang, S Reisberg, V Noel, L A Dang, H T Duc, M C Pham. Direct and rapid electrochemical immunosensing system based on a conducting polymer.
Talanta.
2010 Jul; 82(2):608-12. doi:
10.1016/j.talanta.2010.05.015. [PMID: 20602943] - S B Varma, D L Jaybhaye. Antihyperglycemic activity of Tectona grandis Linn. bark extract on alloxan induced diabetes in rats.
International journal of Ayurveda research.
2010 Jul; 1(3):163-6. doi:
10.4103/0974-7788.72488. [PMID: 21170208] - Edson Luis Maistro, Diego Mota Fernandes, Fernanda Maria Pereira, Sergio Faloni Andrade. Lapachol induces clastogenic effects in rats.
Planta medica.
2010 Jun; 76(9):858-62. doi:
10.1055/s-0029-1240816. [PMID: 20112181] - 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] - Hong Liu, Yong-Sheng Jin, Yan Song, Xiang-Nan Yang, Xiao-Wei Yang, Dong-Sheng Geng, Hai-Sheng Chen. Three new compounds from Arnebia euchroma.
Journal of Asian natural products research.
2010 Apr; 12(4):286-92. doi:
10.1080/10286021003743861. [PMID: 20419539] - Haviva Eilenberg, Smadar Pnini-Cohen, Yocheved Rahamim, Edward Sionov, Esther Segal, Shmuel Carmeli, Aviah Zilberstein. Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana.
Journal of experimental botany.
2010 Mar; 61(3):911-22. doi:
10.1093/jxb/erp359. [PMID: 20018905] - N V Vinod, R Shijina, K V Dileep, C Sadasivan. Inhibition of beta-lactamase by 1,4-naphthalenedione from the plant Holoptelea integrifolia.
Applied biochemistry and biotechnology.
2010 Mar; 160(6):1752-9. doi:
10.1007/s12010-009-8656-2. [PMID: 19424669] - Wilawan Mahabusarakam, Chulida Hemtasin, Suda Chakthong, Supayang Piyawan Voravuthikunchai, Ifesan Beatrice Olawumi. Naphthoquinones, anthraquinones and naphthalene derivatives from the bulbs of Eleutherine americana.
Planta medica.
2010 Mar; 76(4):345-9. doi:
10.1055/s-0029-1186143. [PMID: 19777423] - José Delano B Marinho-Filho, Daniel P Bezerra, Ana J Araújo, Raquel C Montenegro, Claudia Pessoa, Jaécio C Diniz, Francisco A Viana, Otília D L Pessoa, Edilberto R Silveira, Manoel O de Moraes, Letícia V Costa-Lotufo. Oxidative stress induction by (+)-cordiaquinone J triggers both mitochondria-dependent apoptosis and necrosis in leukemia cells.
Chemico-biological interactions.
2010 Feb; 183(3):369-79. doi:
10.1016/j.cbi.2009.11.030. [PMID: 19962971] - An S Tan, Michael V Berridge. Evidence for NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone-dependent redox cycling via plasma membrane electron transport: A sensitive cellular assay for NQO1.
Free radical biology & medicine.
2010 Feb; 48(3):421-9. doi:
10.1016/j.freeradbiomed.2009.11.016. [PMID: 19932748] - N V Vinod, M Haridas, C Sadasivan. Isolation of 1,4-naphthalenedione, an antibacterial principle from the leaves of Holoptelea integrifolia and its activity against beta-lactam resistant Staphylococcus aureus.
Indian journal of biochemistry & biophysics.
2010 Feb; 47(1):53-5. doi:
". [PMID: 21086756] - Lijuan Chen, Guogang Zhang, Jie He, Jin Guan, Chunyuan Pan, Wenzhen Mi, Qing Wang. New naphthoquinone from the root of Lygodium japonicum (Thunb.) Sw.
Journal of natural medicines.
2010 Jan; 64(1):114-6. doi:
10.1007/s11418-009-0376-y. [PMID: 20091244] - Nirmal K Bairwa, Neeraj K Sethiya, S H Mishra. Protective effect of stem bark of Ceiba pentandra linn. against paracetamol-induced hepatotoxicity in rats.
Pharmacognosy research.
2010 Jan; 2(1):26-30. doi:
10.4103/0974-8490.60584. [PMID: 21808535] - Victor Kuete, Thomas Efferth. Cameroonian medicinal plants: pharmacology and derived natural products.
Frontiers in pharmacology.
2010; 1(?):123. doi:
10.3389/fphar.2010.00123. [PMID: 21833168] - Carlos R Arias-Barreiro, Keisuke Okazaki, Apostolos Koutsaftis, Salmaan H Inayat-Hussain, Akio Tani, Maki Katsuhara, Kazuhide Kimbara, Izumi C Mori. A bacterial biosensor for oxidative stress using the constitutively expressed redox-sensitive protein roGFP2.
Sensors (Basel, Switzerland).
2010; 10(7):6290-6306. doi:
10.3390/s100706290. [PMID: 22163550] - Supriya Baikar, Nutan Malpathak. Secondary metabolites as DNA topoisomerase inhibitors: A new era towards designing of anticancer drugs.
Pharmacognosy reviews.
2010 Jan; 4(7):12-26. doi:
10.4103/0973-7847.65320. [PMID: 22228937] - Chi-I Chang, Chiy-Rong Chen, Hsi-Lin Chiu, Chao-Lin Kuo, Yueh-Hsiung Kuo. Chemical constituents from the stems of Diospyros maritima.
Molecules (Basel, Switzerland).
2009 Dec; 14(12):5281-8. doi:
10.3390/molecules14125281. [PMID: 20032891] - Markus Ganzera, Ivo Nischang, Christian Siegl, Birgit Senzenberger, Frantisek Svec, Hermann Stuppner. Application of MEKC and monolithic CEC for the analysis of bioactive naphthoquinones in Eleutherine americana.
Electrophoresis.
2009 Nov; 30(21):3757-63. doi:
10.1002/elps.200900247. [PMID: 19862752] - Supinya Tewtrakul, Pimpimon Tansakul, Pharkphoom Panichayupakaranant. Anti-allergic principles of Rhinacanthus nasutus leaves.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Oct; 16(10):929-34. doi:
10.1016/j.phymed.2009.03.010. [PMID: 19403288] - Po-Hsiung Lin, Dar-Ren Chen, Tzu-Wen Wang, Chia-Hua Lin, Ming-Chieh Chuang. Investigation of the cumulative tissue doses of naphthoquinones in human serum using protein adducts as biomarker of exposure.
Chemico-biological interactions.
2009 Sep; 181(1):107-14. doi:
10.1016/j.cbi.2009.05.016. [PMID: 19505452] - S Nazeem, Asfar S Azmi, Sarmad Hanif, Aamir Ahmad, Ramzi M Mohammad, S M Hadi, K Sateesh Kumar. Plumbagin induces cell death through a copper-redox cycle mechanism in human cancer cells.
Mutagenesis.
2009 Sep; 24(5):413-8. doi:
10.1093/mutage/gep023. [PMID: 19505895] - 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] - Pongpun Siripong, Chariya Hahnvajanawong, Jantana Yahuafai, Suratsawadee Piyaviriyakul, Kwanjai Kanokmedhakul, Ngampong Kongkathip, Somsak Ruchirawat, Naoto Oku. Induction of apoptosis by rhinacanthone isolated from Rhinacanthus nasutus roots in human cervical carcinoma cells.
Biological & pharmaceutical bulletin.
2009 Jul; 32(7):1251-60. doi:
10.1248/bpb.32.1251. [PMID: 19571394] - Kazuaki Ohara, Ayumu Muroya, Nobuhiro Fukushima, Kazufumi Yazaki. Functional characterization of LePGT1, a membrane-bound prenyltransferase involved in the geranylation of p-hydroxybenzoic acid.
The Biochemical journal.
2009 Jun; 421(2):231-41. doi:
10.1042/bj20081968. [PMID: 19392660] - Supinya Tewtrakul, Pimpimon Tansakul, Pharkphoom Panichayupakaranant. Effects of rhinacanthins from Rhinacanthus nasutus on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha releases using RAW264.7 macrophage cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Jun; 16(6-7):581-5. doi:
10.1016/j.phymed.2008.12.022. [PMID: 19303271] - Huanjie Yang, Ping Zhou, Hongbiao Huang, Di Chen, Ningfang Ma, Qiuzhi Cindy Cui, Shouxing Shen, Weihua Dong, Xiaoyan Zhang, Wen Lian, Xuejun Wang, Q Ping Dou, Jinbao Liu. Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo.
International journal of cancer.
2009 May; 124(10):2450-9. doi:
10.1002/ijc.24195. [PMID: 19165859] - Daiva Tauraite, Valdemaras Razumas, Eugenijus Butkus. Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein.
Chemistry and physics of lipids.
2009 May; 159(1):45-50. doi:
10.1016/j.chemphyslip.2009.02.002. [PMID: 19428362] - Mei-Feng Hsu, Ling-Chu Chang, Li-Jiau Huang, Sheng-Chu Kuo, Hsiao-Yun Lee, Min-Chi Lu, Jih-Pyang Wang. The influence of acetylshikonin, a natural naphthoquinone, on the production of leukotriene B4 and thromboxane A2 in rat neutrophils.
European journal of pharmacology.
2009 Apr; 607(1-3):234-43. doi:
10.1016/j.ejphar.2009.02.005. [PMID: 19232341] - Neila C de Sousa, Alexandre A A de Rezende, Regildo M G da Silva, Zaira R Guterres, Ulrich Graf, Warwick E Kerr, Mário A Spanó. Modulatory effects of Tabebuia impetiginosa (Lamiales, Bignoniaceae) on doxorubicin-induced somatic mutation and recombination in Drosophila melanogaster.
Genetics and molecular biology.
2009 Apr; 32(2):382-8. doi:
10.1590/s1415-47572009005000042. [PMID: 21637695] - Gunjan M Modi, Christy B Doherty, Rajani Katta, Ida F Orengo. Irritant contact dermatitis from plants.
Dermatitis : contact, atopic, occupational, drug.
2009 Mar; 20(2):63-78. doi:
. [PMID: 19426612] - Rubem F S Menna-Barreto, Kelly Salomão, Andréia P Dantas, Ricardo M Santa-Rita, Maurilio J Soares, Helene S Barbosa, Solange L de Castro. Different cell death pathways induced by drugs in Trypanosoma cruzi: an ultrastructural study.
Micron (Oxford, England : 1993).
2009 Feb; 40(2):157-68. doi:
10.1016/j.micron.2008.08.003. [PMID: 18849169] - Hyo-Jung Lee, Hyo-Jeong Lee, Venkataraman Magesh, Dongwoo Nam, Eun-Ok Lee, Kwang Seok Ahn, Min-Hyung Jung, Kyoo-Seok Ahn, Dae-Keun Kim, Ji-Young Kim, Sung-Hoon Kim. Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2008 Nov; 128(11):1681-8. doi:
10.1248/yakushi.128.1681. [PMID: 18981704] - Makiko Yoshida, Paul F Jacques, James B Meigs, Edward Saltzman, M Kyla Shea, Caren Gundberg, Bess Dawson-Hughes, Gerard Dallal, Sarah L Booth. Effect of vitamin K supplementation on insulin resistance in older men and women.
Diabetes care.
2008 Nov; 31(11):2092-6. doi:
10.2337/dc08-1204. [PMID: 18697901] - Aya Matsuu, Masahiro Yamasaki, Xuenan Xuan, Hiromi Ikadai, Yoshiaki Hikasa. In vitro evaluation of the growth inhibitory activities of 15 drugs against Babesia gibsoni (Aomori strain).
Veterinary parasitology.
2008 Oct; 157(1-2):1-8. doi:
10.1016/j.vetpar.2008.07.023. [PMID: 18771856] - Kenneth O Eyong, Ponminor S Kumar, Victor Kuete, Gabriel N Folefoc, Ephriam A Nkengfack, Sundarababu Baskaran. Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.
Bioorganic & medicinal chemistry letters.
2008 Oct; 18(20):5387-90. doi:
10.1016/j.bmcl.2008.09.053. [PMID: 18829316] - Sompol Paramapojn, Markus Ganzera, Wandee Gritsanapan, Hermann Stuppner. Analysis of naphthoquinone derivatives in the Asian medicinal plant Eleutherine americana by RP-HPLC and LC-MS.
Journal of pharmaceutical and biomedical analysis.
2008 Aug; 47(4-5):990-3. doi:
10.1016/j.jpba.2008.04.005. [PMID: 18486396] - Lyndy Joy McGaw, Namrita Lall, Tiny Motlatso Hlokwe, Anita Luise Michel, Jacobus Johannes Marion Meyer, Jacobus Nicolaas Eloff. Purified compounds and extracts from Euclea species with antimycobacterial activity against Mycobacterium bovis and fast-growing mycobacteria.
Biological & pharmaceutical bulletin.
2008 Jul; 31(7):1429-33. doi:
10.1248/bpb.31.1429. [PMID: 18591787] - Gianni Sagratini, Gloria Cristalli, Dario Giardinà, Giorgio Gioventù, Filippo Maggi, Massimo Ricciutelli, Sauro Vittori. Alkannin/shikonin mixture from roots of Onosma echioides (L.) L.: extraction method study and quantification.
Journal of separation science.
2008 Apr; 31(6-7):945-52. doi:
10.1002/jssc.200700408. [PMID: 18327849]