Lawsone (BioDeep_00000180408)
human metabolite PANOMIX_OTCML-2023 blood metabolite natural product
代谢物信息卡片
化学式: C10H6O3 (174.0317)
中文名称: 2-羟基-1,4-萘醌
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 50%
分子结构信息
SMILES: C1=CC=C2C(=C1)C(=CC(=O)C2=O)O
InChI: InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,11H
描述信息
D020011 - Protective Agents > D011837 - Radiation-Protective Agents > D013473 - Sunscreening Agents
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D003879 - Dermatologic Agents
D004791 - Enzyme Inhibitors
D004396 - Coloring Agents
D003358 - Cosmetics
Lawsone is a naphthoquinone dye isolated from leaves of Lawsonia inermis that shows antimicrobial and antioxidant activity[1].
Lawsone is a naphthoquinone dye isolated from leaves of Lawsonia inermis that shows antimicrobial and antioxidant activity[1].
同义名列表
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:44401
- PubChem: 6755
- HMDB: HMDB0253997
- DrugBank: DB04744
- ChEMBL: CHEMBL240963
- Wikipedia: Lawsone
- KNApSAcK: C00002837
- chemspider: 6498
- CAS: 27699-93-0
- CAS: 83-72-7
- medchemexpress: HY-N2493
- KEGG: C10368
- PubChem: 12554
- KNApSAcK: 44401
- LOTUS: LTS0266331
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)
33 个相关的物种来源信息
- 25692 - Balsaminaceae: LTS0266331
- 2759 - Eukaryota: LTS0266331
- 9606 - Homo sapiens: -
- 35939 - Impatiens: LTS0266331
- 63779 - Impatiens balsamina:
- 63779 - Impatiens balsamina: 10.1002/(SICI)1099-1573(199605)10:3<202::AID-PTR805>3.0.CO;2-0
- 63779 - Impatiens balsamina: 10.1002/PTR.964
- 63779 - Impatiens balsamina: 10.1016/0031-9422(95)00418-7
- 63779 - Impatiens balsamina: 10.1016/S0031-9422(00)86833-8
- 63779 - Impatiens balsamina: 10.1076/PHBI.39.4.293.5909
- 63779 - Impatiens balsamina: 10.1248/BPB.25.505
- 63779 - Impatiens balsamina: 10.1515/ZNC-1994-11-1226
- 63779 - Impatiens balsamina: LTS0266331
- 63779 - Impatiens balsamina L.: -
- 55378 - Impatiens capensis: 10.1002/PCA.574
- 55378 - Impatiens capensis: LTS0266331
- 253017 - Impatiens glandulifera: 10.1002/PCA.574
- 253017 - Impatiens glandulifera: LTS0266331
- 127129 - Impatiens noli-tangere: 10.1002/PCA.574
- 127129 - Impatiens noli-tangere: LTS0266331
- 191132 - Impatiens parviflora: 10.1002/PCA.574
- 191132 - Impatiens parviflora: LTS0266331
- 41707 - Lawsonia: LTS0266331
- 141191 - Lawsonia inermis:
- 141191 - Lawsonia inermis: 10.1016/S0031-9422(01)00329-6
- 141191 - Lawsonia inermis: 10.1016/S0044-4057(73)80039-5
- 141191 - Lawsonia inermis: LTS0266331
- 3928 - Lythraceae: LTS0266331
- 3398 - Magnoliopsida: LTS0266331
- 33090 - Plants: -
- 35493 - Streptophyta: LTS0266331
- 58023 - Tracheophyta: LTS0266331
- 33090 - Viridiplantae: LTS0266331
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
- Shilin Wen, Jingang Huang, Weishuai Li, Mengke Wu, Felix Steyskal, Jianfang Meng, Xiaobin Xu, Pingzhi Hou, Junhong Tang. Henna plant biomass enhanced azo dye removal: Operating performance, microbial community and machine learning modeling.
Chemosphere.
2024 Mar; 352(?):141471. doi:
10.1016/j.chemosphere.2024.141471
. [PMID: 38373445] - Jin-Hyung Lee, Yong-Guy Kim, Jintae Lee. Antibiofilm activity of lawsone against polymicrobial enterohemorrhagic Escherichia coli O157:H7 and Candida albicans by suppression of curli production and hyphal growth.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2024 Feb; 124(?):155306. doi:
10.1016/j.phymed.2023.155306
. [PMID: 38176270] - Bolesław Szadkowski, Anna Marzec, Małgorzata Kuśmierek, Małgorzata Piotrowska, Dariusz Moszyński. Functionalization of bamboo fibers with lawsone dye (Lawsonia inermis) to produce bioinspired hybrid color composite with antibacterial activity.
International journal of biological macromolecules.
2024 Jan; 259(Pt 1):129178. doi:
10.1016/j.ijbiomac.2023.129178
. [PMID: 38184044] - K E Zannat, S M Tanzim, A Afrin, N Akter, M S Mostaqim, J B Joynal, M Ferdausee, B C Saha, N H Nira. Antibacterial Effects of Methanol Henna (Lawsone inermis) Leaf Extracts against Two Food Borne Infection Causing Pathogens: Gram-Positive Staphylococcus aureus and Gram Negative Klebsiella pneumoniae.
Mymensingh medical journal : MMJ.
2023 Oct; 32(4):1009-1014. doi:
. [PMID: 37777894]
- Mohsen Rezaeian, Maryam Mohamadi, Hassan Ahmadinia, Hamidreza Mohammadi, Ali Ghaffarian-Bahraman. Lead and arsenic contamination in henna samples marketed in Iran.
Environmental monitoring and assessment.
2023 Jul; 195(8):913. doi:
10.1007/s10661-023-11532-y
. [PMID: 37395865] - 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] - Hany Tobia Michael, Dhanya Mohan, Hind Aljaghber, Fakhriya Alalawi, Mohammed Railey, Amna Alhadari. Topical Henna Application Causing Acute Kidney Injury and Acute Hemolytic Anemia.
Saudi journal of kidney diseases and transplantation : an official publication of the Saudi Center for Organ Transplantation, Saudi Arabia.
2023 Mar; 34(2):178-186. doi:
10.4103/1319-2442.391897
. [PMID: 38146728] - Mehdi Pasalar, Bahareh Ahadi, Hamid Reza Mirzaei, Judith Buentzel, Mojgan Mehri Ardestani, Shaghayegh Kamian, Ghazaleh Heydarirad. Comparing Dermolina-Henna Cream with Mometasone Cream in Improving Radiodermatitis Among Patients with Breast Cancer: A Randomized Active-Control Double-Blind Clinical Trial.
Journal of integrative and complementary medicine.
2022 Nov; 28(11):895-903. doi:
10.1089/jicm.2022.0551
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Medicinal chemistry (Shariqah (United Arab Emirates)).
2022; 18(2):170-180. doi:
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Transfusion and apheresis science : official journal of the World Apheresis Association : official journal of the European Society for Haemapheresis.
2021 Dec; 60(6):103204. doi:
10.1016/j.transci.2021.103204
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Chemistry and physics of lipids.
2021 09; 239(?):105123. doi:
10.1016/j.chemphyslip.2021.105123
. [PMID: 34403685] - Juliana Figueiredo Peixoto, Adriane da Silva Oliveira, Patrícia Queiroz Monteiro, Luiz Filipe Gonçalves-Oliveira, Valter Viana Andrade-Neto, Vitor Francisco Ferreira, Franklin Souza-Silva, Carlos Roberto Alves. In Silico Insights into the Mechanism of Action of Epoxy-α-Lapachone and Epoxymethyl-Lawsone in Leishmania spp.
Molecules (Basel, Switzerland).
2021 Jun; 26(12):. doi:
10.3390/molecules26123537
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Cell reports.
2021 04; 35(4):109040. doi:
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. [PMID: 33910017] - Porkodi Jeyaraman, Michael Samuel, Antonysamy Johnson, Natarajan Raman. Synthesis, characterization, ADMET, in vitro and in vivo studies of mixed ligand metal complexes from a curcumin Schiff base and lawsone.
Nucleosides, nucleotides & nucleic acids.
2021; 40(3):242-263. doi:
10.1080/15257770.2020.1867865
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Natural product research.
2020 Dec; 34(23):3399-3403. doi:
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Scientific reports.
2020 09; 10(1):16123. doi:
10.1038/s41598-020-72997-2
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Cancer investigation.
2020 Sep; 38(8-9):476-485. doi:
10.1080/07357907.2020.1811300
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Veterinary medicine and science.
2020 08; 6(3):441-446. doi:
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Journal of investigational allergology & clinical immunology.
2020 Apr; 30(2):133-134. doi:
10.18176/jiaci.0453
. [PMID: 31530513] - Mariana Rodrigues Xavier, Manuella Maria Silva Santos, Maise Gomes Queiroz, Mariza S de Lima Silva, Alexandre José S Goes, Marcos Antonio De Morais. Lawsone, a 2-hydroxy-1,4-naphthoquinone from Lawsonia inermis (henna), produces mitochondrial dysfunctions and triggers mitophagy in Saccharomyces cerevisiae.
Molecular biology reports.
2020 Feb; 47(2):1173-1185. doi:
10.1007/s11033-019-05218-3
. [PMID: 31811499] - Laura Lozza, Pedro Moura-Alves, Teresa Domaszewska, Carolina Lage Crespo, Ioana Streata, Annika Kreuchwig, Andreas Puyskens, Marina Bechtle, Marion Klemm, Ulrike Zedler, Bogdan Silviu Ungureanu, Ute Guhlich-Bornhof, Anne-Britta Koehler, Manuela Stäber, Hans-Joachim Mollenkopf, Robert Hurwitz, Jens Furkert, Gerd Krause, January Weiner, António Jacinto, Ioana Mihai, Maria Leite-de-Moraes, Frank Siebenhaar, Marcus Maurer, Stefan H E Kaufmann. The Henna pigment Lawsone activates the Aryl Hydrocarbon Receptor and impacts skin homeostasis.
Scientific reports.
2019 07; 9(1):10878. doi:
10.1038/s41598-019-47350-x
. [PMID: 31350436] - 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] - 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] - Yoshimi Oda, Souichi Nakashima, Erina Kondo, Seikou Nakamura, Mamiko Yano, Chisa Kubota, Yusuke Masumoto, Minami Hirao, Yuki Ogawa, Hisashi Matsuda. Comparison of lawsone contents among Lawsonia inermis plant parts and neurite outgrowth accelerators from branches.
Journal of natural medicines.
2018 Sep; 72(4):890-896. doi:
10.1007/s11418-018-1221-y
. [PMID: 29777444] - Mahmood Barani, Mohammad Mirzaei, Masoud Torkzadeh-Mahani, Mohammad Hadi Nematollahi. Lawsone-loaded Niosome and its antitumor activity in MCF-7 breast Cancer cell line: a Nano-herbal treatment for Cancer.
Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences.
2018 Sep; 26(1):11-17. doi:
10.1007/s40199-018-0207-3
. [PMID: 30159762] - S Sylvester Darvin, S Esakkimuthu, Erenius Toppo, K Balakrishna, M Gabriel Paulraj, P Pandikumar, S Ignacimuthu, N A Al-Dhabi. Hepatoprotective effect of lawsone on rifampicin-isoniazid induced hepatotoxicity in in vitro and in vivo models.
Environmental toxicology and pharmacology.
2018 Jul; 61(?):87-94. doi:
10.1016/j.etap.2018.05.006
. [PMID: 29859372] - 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] - Sameh S M Soliman, Abrar I Alsaadi, Eman G Youssef, Gregory Khitrov, Ayman M Noreddin, Mohamed I Husseiny, Ashraf S Ibrahim. Calli Essential Oils Synergize with Lawsone against Multidrug Resistant Pathogens.
Molecules (Basel, Switzerland).
2017 Dec; 22(12):. doi:
10.3390/molecules22122223
. [PMID: 29261103] - S H S Dananjaya, R M C Udayangani, Sang Yeop Shin, M Edussuriya, Chamilani Nikapitiya, Jehee Lee, Mahanama De Zoysa. In vitro and in vivo antifungal efficacy of plant based lawsone against Fusarium oxysporum species complex.
Microbiological research.
2017 Aug; 201(?):21-29. doi:
10.1016/j.micres.2017.04.011
. [PMID: 28602398] - Lamis Beshir, Babiker Kaballo, Donald Young. Attempted suicide by ingestion of hair dye containing p-phenylenediamine: a case report.
Annals of clinical biochemistry.
2017 Jul; 54(4):507-510. doi:
10.1177/0004563216685117
. [PMID: 27923888] - Hatnagar Sarang, Pijakala Rajani, Madhugiri Mallaiah Vasanthakumari, Patel Mohana Kumara, Ramamoorthy Siva, Gudasalamani Ravikanth, R Uma Shaanker. An endophytic fungus, Gibberella moniliformis from Lawsonia inermis L. produces lawsone, an orange-red pigment.
Antonie van Leeuwenhoek.
2017 Jul; 110(7):853-862. doi:
10.1007/s10482-017-0858-y
. [PMID: 28315019] - Shi-Bin Wang, Zhenzhou Tao, Ping Li. Lawsone suppresses azoxymethane mediated colon cancer in rats and reduces proliferation of DLD-1 cells via NF-κB pathway.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2017 May; 89(?):152-161. doi:
10.1016/j.biopha.2017.01.169
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Memorias do Instituto Oswaldo Cruz.
2017 Apr; 112(4):299-308. doi:
10.1590/0074-02760160417
. [PMID: 28327793] - Aysha Aslam, Faisal Samee, Muhammad Zaman, Attique Ur Rahman Mufti, Atiq Ur Rehman. FORMULATION AND ASSESSMENT OF SEMI-SOLID CARRIER INCORPORATED WITH HERBAL EXTRACT OF LAWSONIA INERMIS.
Acta poloniae pharmaceutica.
2017 Mar; 74(2):497-504. doi:
"
. [PMID: 29624255] - Ayca Aktas Sukuroglu, Dilek Battal, Sema Burgaz. Monitoring of Lawsone, p-phenylenediamine and heavy metals in commercial temporary black henna tattoos sold in Turkey.
Contact dermatitis.
2017 Feb; 76(2):89-95. doi:
10.1111/cod.12702
. [PMID: 27757963] - Ruchi Badoni Semwal, Deepak Kumar Semwal, Sandra Combrinck, Catherine Cartwright-Jones, Alvaro Viljoen. Lawsonia inermis L. (henna): ethnobotanical, phytochemical and pharmacological aspects.
Journal of ethnopharmacology.
2014 Aug; 155(1):80-103. doi:
10.1016/j.jep.2014.05.042
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Iranian journal of kidney diseases.
2014 Jun; 8(4):349-51. doi:
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Bioorganic & medicinal chemistry letters.
2014 Jan; 24(2):454-7. doi:
10.1016/j.bmcl.2013.12.049
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BioMed research international.
2014; 2014(?):461393. doi:
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. [PMID: 25045679] - Govind J Kapadia, G Subba Rao, Rajagopalan Sridhar, Eiichiro Ichiishi, Midori Takasaki, Nobutaka Suzuki, Takao Konoshima, Akira Iida, Harukuni Tokuda. Chemoprevention of skin cancer: effect of Lawsonia inermis L. (Henna) leaf powder and its pigment artifact, lawsone in the Epstein- Barr virus early antigen activation assay and in two-stage mouse skin carcinogenesis models.
Anti-cancer agents in medicinal chemistry.
2013 Dec; 13(10):1500-7. doi:
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. [PMID: 23848207] - Sandeep Biradar, B Veeresh. Protective effect of lawsone on L-Arginine induced acute pancreatitis in rats.
Indian journal of experimental biology.
2013 Mar; 51(3):256-61. doi:
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Pharmaceutical biology.
2013 Jan; 51(1):131-5. doi:
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Journal of agricultural and food chemistry.
2012 Dec; 60(49):12074-81. doi:
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Current drug targets.
2012 Dec; 13(14):1777-98. doi:
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Journal of ethnopharmacology.
2012 Aug; 143(1):314-8. doi:
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International journal of dermatology.
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Contact dermatitis.
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Journal of bioscience and bioengineering.
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Journal of enzyme inhibition and medicinal chemistry.
2009 Feb; 24(1):257-61. doi:
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The Journal of dermatology.
2009 Jan; 36(1):63-5. doi:
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Investigational new drugs.
2008 Apr; 26(2):189-92. doi:
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