kojic acid (BioDeep_00000014951)

 

Secondary id: BioDeep_00000001624

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-

化学式: C6H6O4 (142.0266076)
中文名称: 曲酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.26%

分子结构信息

SMILES: C1=C(OC=C(C1=O)O)CO
InChI: InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2

描述信息

A pyranone that is 4H-pyran substituted by a hydroxy group at position 5, a hydroxymethyl group at position 2 and an oxo group at position 4. It has been isolated from the fungus Aspergillus oryzae.
D020011 - Protective Agents > D000975 - Antioxidants
CONFIDENCE Reference Standard (Level 1)
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.107
Kojic acid is a natural substance produced by Aspergillus oryzae, also used as an anti-oxidant and radio-protective agent[1].
Kojic acid is a natural substance produced by Aspergillus oryzae, also used as an anti-oxidant and radio-protective agent[1].

同义名列表

56 个代谢物同义名

kojic acid; 4H-Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-; 5-18-02-00516 (Beilstein Handbook Reference); 2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one; 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one; Pyran-4-one, 5-hydroxy-2-(hydroxymethyl); 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone; 5-hydroxy-2-(hydroxymethyl)-4-pyranone; 2-Hydroxymethyl-5-hydroxy-gamma-pyrone; 5-Hydroxy-2-(hydroxymethyl)pyran-4-one; 5-Hydroxy-2-(hydroxymethyl)-4-pyrone; 5-Hydroxy-2-hydroxymethyl-4-pyrone; 5-hydroxy-2-methylol-pyran-4-one; WLN: T6O DVJ B1Q EQ; nchembio.78-comp13; Spectrum3_001704; Spectrum4_000571; Spectrum2_001828; Spectrum5_001085; EINECS 207-922-4; NCGC00017325-01; NCGC00142361-01; Spectrum_000191; Oprea1_038773; BSPBio_003288; KBioSS_000671; MEGxm0_000388; DivK1c_000923; KBioGR_001002; KBio2_000671; KBio1_000923; NINDS_000923; KBio2_003239; SPBio_001875; ACon1_000622; KBio3_002508; KBio2_005807; ZINC00031978; IDI1_000923; SMP1_000171; BRN 0120895; K3125_SIGMA; AIDS-009875; 123712-78-7; CHEBI:43572; 60890_FLUKA; CCRIS 4131; AIDS009875; AI3-02549; SBB005397; 501-30-4; TNP00261; NSC 1942; NSC1942; C14516; KOJ



数据库引用编号

37 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)

13 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。



文献列表

  • Aatrayee Das, Sonia Kundu, Mradu Gupta, Arup Mukherjee. Guar gum propionate-kojic acid films for Escherichia coli biofilm disruption and simultaneous inhibition of planktonic growth. International journal of biological macromolecules. 2022 Jun; 211(?):57-73. doi: 10.1016/j.ijbiomac.2022.05.052. [PMID: 35576698]
  • Ying Zhou, Hong-Liang Zeng, Xin-Yue Wen, Ling Jiang, Chu-Han Fu, Yi-Bo Hu, Xin-Xin Lei, Li Zhang, Xing Yu, Si-Yu Yang, Li-Hua Huang, Hong Xiang, Jin-Hua Huang, Jing Chen, Li Lei, Qing-Hai Zeng. Selaginellin Inhibits Melanogenesis via the MAPK Signaling Pathway. Journal of natural products. 2022 04; 85(4):838-845. doi: 10.1021/acs.jnatprod.1c00971. [PMID: 35290062]
  • Joanna I Lachowicz, Anna Mateddu, Pierpaolo Coni, Claudia Caltagirone, Sergio Murgia, Dan Gibson, Gabriele Dalla Torre, Xabier Lopez, Federico Meloni, Giuseppina Pichiri. Study of the DNA binding mechanism and in vitro activity against cancer cells of iron(III) and aluminium(III) kojic acid derivative complexes. Dalton transactions (Cambridge, England : 2003). 2022 Apr; 51(16):6254-6263. doi: 10.1039/d2dt00111j. [PMID: 35373808]
  • Herman Suryadi, Marina Ika Irianti, Tri Hastuti Septiarini. Methods of Random Mutagenesis of Aspergillus Strain for Increasing Kojic Acid Production. Current pharmaceutical biotechnology. 2022; 23(4):486-494. doi: 10.2174/1389201022666210615125004. [PMID: 34132182]
  • Xiang Liu, Jinqiu Rao, Kai Wang, Meijun Wang, Tie Yao, Feng Qiu. Highly Potent Inhibition of Tyrosinase by Mulberrosides and the Inhibitory Mechanism in Vitro. Chemistry & biodiversity. 2022 Jan; 19(1):e202100740. doi: 10.1002/cbdv.202100740. [PMID: 34752017]
  • Dingqiang Fu, Yi Yuan, Fengming Qin, Yan Xu, Xin Cui, Guangxun Li, Shaohua Yao, Yun Deng, Zhuo Tang. Design, synthesis and biological evaluation of tyrosinase-targeting PROTACs. European journal of medicinal chemistry. 2021 Dec; 226(?):113850. doi: 10.1016/j.ejmech.2021.113850. [PMID: 34628235]
  • Khadijeh Khezri, Majid Saeedi, Katayoun Morteza-Semnani, Jafar Akbari, Akbar Hedayatizadeh-Omran. A promising and effective platform for delivering hydrophilic depigmenting agents in the treatment of cutaneous hyperpigmentation: kojic acid nanostructured lipid carrier. Artificial cells, nanomedicine, and biotechnology. 2021 Dec; 49(1):38-47. doi: 10.1080/21691401.2020.1865993. [PMID: 33438443]
  • Avni Nautiyal, Sarika Wairkar. Management of hyperpigmentation: Current treatments and emerging therapies. Pigment cell & melanoma research. 2021 11; 34(6):1000-1014. doi: 10.1111/pcmr.12986. [PMID: 33998768]
  • Amjad Khan, Tae Ju Park, Muhammad Ikram, Sareer Ahmad, Riaz Ahmad, Min Gi Jo, Myeong Ok Kim. Antioxidative and Anti-inflammatory Effects of Kojic Acid in Aβ-Induced Mouse Model of Alzheimer's Disease. Molecular neurobiology. 2021 Oct; 58(10):5127-5140. doi: 10.1007/s12035-021-02460-4. [PMID: 34255249]
  • Farah J Hashim, Sukanda Vichitphan, Jaehong Han, Kanit Vichitphan. Alternative Approach for Specific Tyrosinase Inhibitor Screening: Uncompetitive Inhibition of Tyrosinase by Moringa oleifera. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154576. [PMID: 34361729]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Khadijeh Khezri, Majid Saeedi, Katayoun Morteza-Semnani, Jafar Akbari, Seyyed Sohrab Rostamkalaei. An emerging technology in lipid research for targeting hydrophilic drugs to the skin in the treatment of hyperpigmentation disorders: kojic acid-solid lipid nanoparticles. Artificial cells, nanomedicine, and biotechnology. 2020 Dec; 48(1):841-853. doi: 10.1080/21691401.2020.1770271. [PMID: 32456476]
  • Sarah Mohamed El-Korany, Omneya Mohamed Helmy, Ali Mahmoud El-Halawany, Yasser El-Mohammadi Ragab, Hamdallah Hafez Zedan. Kojic acid repurposing as a pancreatic lipase inhibitor and the optimization of its production from a local Aspergillus oryzae soil isolate. BMC biotechnology. 2020 10; 20(1):52. doi: 10.1186/s12896-020-00644-9. [PMID: 33008398]
  • Sameh S M Soliman, Rania Hamdy, Samia A Elseginy, Teclegiorgis Gebremariam, Alshaimaa M Hamoda, Mohamed Madkour, Thenmozhi Venkatachalam, Mai N Ershaid, Mohammad G Mohammad, Georgios Chamilos, Ashraf S Ibrahim. Selective inhibition of Rhizopus eumelanin biosynthesis by novel natural product scaffold-based designs caused significant inhibition of fungal pathogenesis. The Biochemical journal. 2020 07; 477(13):2489-2507. doi: 10.1042/bcj20200310. [PMID: 32538426]
  • Chie Miyabe, Yupeng Dong, Kazumasa Wakamatsu, Shosuke Ito, Tamihiro Kawakami. Kojic acid alters pheomelanin content in human induced pluripotent stem cell-derived melanocytes. The Journal of dermatology. 2020 Apr; 47(4):435-436. doi: 10.1111/1346-8138.15260. [PMID: 32067265]
  • Weike Shaoyong, Qian Li, Zhiqiang Ren, Junying Xiao, Zhaoxi Diao, Gongshe Yang, Weijun Pang. Effects of kojic acid on boar sperm quality and anti-bacterial activity during liquid preservation at 17 C. Theriogenology. 2019 Dec; 140(?):124-135. doi: 10.1016/j.theriogenology.2019.08.020. [PMID: 31473495]
  • Antonius R B Ola, Gema Metboki, Caterina S Lay, Yoseph Sugi, Philipi De Rozari, Dodi Darmakusuma, Euis Holisotan Hakim. Single Production of Kojic Acid by Aspergillus flavus and the Revision of Flufuran. Molecules (Basel, Switzerland). 2019 Nov; 24(22):. doi: 10.3390/molecules24224200. [PMID: 31752404]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • María D Santi, Mariana A Peralta, Marcelo Puiatti, José Luis Cabrera, María G Ortega. Melanogenic inhibitory effects of Triangularin in B16F0 melanoma cells, in vitro and molecular docking studies. Bioorganic & medicinal chemistry. 2019 08; 27(16):3722-3728. doi: 10.1016/j.bmc.2019.06.041. [PMID: 31272835]
  • Ji Yeong Kim, Jeong Yoon Kim, Janar Jenis, Zuo Peng Li, Yeong Jun Ban, Aizhamal Baiseitova, Ki Hun Park. Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle). Bioorganic & medicinal chemistry. 2019 06; 27(12):2499-2507. doi: 10.1016/j.bmc.2019.03.013. [PMID: 30871862]
  • Mahbobeh Montazeri, Saeed Emami, Hossein Asgarian-Omran, Soheil Azizi, Mehdi Sharif, Shahabeddin Sarvi, Fatemeh Rezaei, Mitra Sadeghi, Shaban Gohardehi, Ahmad Daryani. In vitro and in vivo evaluation of kojic acid against Toxoplasma gondii in experimental models of acute toxoplasmosis. Experimental parasitology. 2019 May; 200(?):7-12. doi: 10.1016/j.exppara.2019.03.009. [PMID: 30904693]
  • Weimeng Feng, Jinrui Liang, Bingbing Wang, Jianhua Chen. Improvement of kojic acid production in Aspergillus oryzae AR-47 mutant strain by combined mutagenesis. Bioprocess and biosystems engineering. 2019 May; 42(5):753-761. doi: 10.1007/s00449-019-02079-9. [PMID: 30805716]
  • Seemal Desai, Eloisa Ayres, Hana Bak, Megan Manco, Stephen Lynch, Susana Raab, Ana Du, DesTenee Green, Cezary Skobowiat, Janet Wangari-Talbot, Qian Zheng. Effect of a Tranexamic Acid, Kojic Acid, and Niacinamide Containing Serum on Facial Dyschromia: A Clinical Evaluation. Journal of drugs in dermatology : JDD. 2019 May; 18(5):454-459. doi: NULL. [PMID: 31141852]
  • H-H Zhang, M-J Luo, Q-W Zhang, P-M Cai, A Idrees, Q-E Ji, J-Q Yang, J-H Chen. Molecular characterization of prophenoloxidase-1 (PPO1) and the inhibitory effect of kojic acid on phenoloxidase (PO) activity and on the development of Zeugodacus tau (Walker) (Diptera: Tephritidae). Bulletin of entomological research. 2019 Apr; 109(2):236-247. doi: 10.1017/s0007485318000470. [PMID: 29929571]
  • Katarzyna Hałdys, Rafał Latajka. Thiosemicarbazones with tyrosinase inhibitory activity. MedChemComm. 2019 Mar; 10(3):378-389. doi: 10.1039/c9md00005d. [PMID: 31015905]
  • Sae On Kim, Yujia Han, Sungjin Ahn, Seungchan An, Jeayoung C Shin, Hyunjung Choi, Hyoung-June Kim, Nok Hyun Park, Yong-Jin Kim, Sun Hee Jin, Ho Sik Rho, Minsoo Noh. Kojyl cinnamate esters are peroxisome proliferator-activated receptor α/γ dual agonists. Bioorganic & medicinal chemistry. 2018 11; 26(21):5654-5663. doi: 10.1016/j.bmc.2018.10.010. [PMID: 30352713]
  • Zhaojun Sheng, Siyuan Ge, Ximing Xu, Yan Zhang, Panpan Wu, Kun Zhang, Xuetao Xu, Chen Li, Denggao Zhao, Xiaowen Tang. Design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors. MedChemComm. 2018 May; 9(5):853-861. doi: 10.1039/c8md00099a. [PMID: 30108974]
  • Navneet Kishore, Danielle Twilley, Analike Blom van Staden, Praveen Verma, Bikram Singh, Giorgia Cardinali, Daniela Kovacs, Mauro Picardo, Vivek Kumar, Namrita Lall. Isolation of Flavonoids and Flavonoid Glycosides from Myrsine africana and Their Inhibitory Activities against Mushroom Tyrosinase. Journal of natural products. 2018 01; 81(1):49-56. doi: 10.1021/acs.jnatprod.7b00564. [PMID: 29300477]
  • Mai T T Nguyen, Tho H Le, Hai X Nguyen, Phu H Dang, Truong N V Do, Manabu Abe, Ryukichi Takagi, Nhan T Nguyen. Artocarmins G-M, Prenylated 4-Chromenones from the Stems of Artocarpus rigida and Their Tyrosinase Inhibitory Activities. Journal of natural products. 2017 12; 80(12):3172-3178. doi: 10.1021/acs.jnatprod.7b00453. [PMID: 29227656]
  • Ruimin Yang, Jing Yang, Li Wang, Jian-Ping Huang, Zijun Xiong, Jianying Luo, Mingming Yu, Yijun Yan, Sheng-Xiong Huang. Lorneic Acid Analogues from an Endophytic Actinomycete. Journal of natural products. 2017 10; 80(10):2615-2619. doi: 10.1021/acs.jnatprod.7b00056. [PMID: 28990780]
  • Dong-Mei Liu, Jun-Li Yang, Wei Ha, Juan Chen, Yan-Ping Shi. Kinetics and inhibition study of tyrosinase by pressure mediated microanalysis. Analytical biochemistry. 2017 05; 525(?):54-59. doi: 10.1016/j.ab.2017.02.020. [PMID: 28257907]
  • María D Santi, Mariana A Peralta, Caterine S Mendoza, José Luis Cabrera, María G Ortega. Chemical and bioactivity of flavanones obtained from roots of Dalea pazensis Rusby. Bioorganic & medicinal chemistry letters. 2017 04; 27(8):1789-1794. doi: 10.1016/j.bmcl.2017.02.058. [PMID: 28268138]
  • Batsukh Odonbayar, Toshihiro Murata, Javzan Batkhuu, Kosho Yasunaga, Rina Goto, Kenroh Sasaki. Antioxidant Flavonols and Phenolic Compounds from Atraphaxis frutescens and Their Inhibitory Activities against Insect Phenoloxidase and Mushroom Tyrosinase. Journal of natural products. 2016 Dec; 79(12):3065-3071. doi: 10.1021/acs.jnatprod.6b00720. [PMID: 28006914]
  • Namrita Lall, Elizabeth Mogapi, Marco Nuno de Canha, Bridget Crampton, Mabatho Nqephe, Ahmed A Hussein, Vivek Kumar. Insights into tyrosinase inhibition by compounds isolated from Greyia radlkoferi Szyszyl using biological activity, molecular docking and gene expression analysis. Bioorganic & medicinal chemistry. 2016 11; 24(22):5953-5959. doi: 10.1016/j.bmc.2016.09.054. [PMID: 27720556]
  • Cy V Credille, Yao Chen, Seth M Cohen. Fragment-Based Identification of Influenza Endonuclease Inhibitors. Journal of medicinal chemistry. 2016 07; 59(13):6444-54. doi: 10.1021/acs.jmedchem.6b00628. [PMID: 27291165]
  • A Maack, A Pegard. Populus nigra (Salicaceae) absolute rich in phenolic acids, phenylpropanoïds and flavonoids as a new potent tyrosinase inhibitor. Fitoterapia. 2016 Jun; 111(?):95-101. doi: 10.1016/j.fitote.2016.04.001. [PMID: 27091790]
  • M H Maneli, L Wiesner, C Tinguely, L M Davids, Z Spengane, P Smith, J C van Wyk, A Jardine, N P Khumalo. Combinations of potent topical steroids, mercury and hydroquinone are common in internationally manufactured skin-lightening products: a spectroscopic study. Clinical and experimental dermatology. 2016 Mar; 41(2):196-201. doi: 10.1111/ced.12720. [PMID: 26211494]
  • Le Duc Dat, Nguyen Phuong Thao, Bui Thi Thuy Luyen, Bui Huu Tai, Min Hee Jeong, Mi Hee Woo, Young Ho Kim. Identification of six new lupane-type triterpenoids from Acanthopanax koreanum leaves and their tyrosinase inhibitory activities. Bioorganic & medicinal chemistry letters. 2016 Feb; 26(3):1061-1067. doi: 10.1016/j.bmcl.2015.12.020. [PMID: 26786496]
  • Mahboobeh Sharifi, Mohammad Ghadamyari, Reza H Sajedi, Nosrat O Mahmoodi. Effects of 4-hexylresorcinol on the phenoloxidase from Hyphantria cunea (Lepidoptera: Arctiidae): In vivo and in vitro studies. Insect science. 2015 Oct; 22(5):639-50. doi: 10.1111/1744-7917.12154. [PMID: 24995395]
  • Shijuan Yan, Yating Liang, Jindan Zhang, Zhuang Chen, Chun-Ming Liu. Autoxidated linolenic acid inhibits aflatoxin biosynthesis in Aspergillus flavus via oxylipin species. Fungal genetics and biology : FG & B. 2015 Aug; 81(?):229-37. doi: 10.1016/j.fgb.2014.11.005. [PMID: 25498164]
  • Souichi Nakashima, Yoshimi Oda, Seikou Nakamura, Jiang Liu, Koko Onishi, Miki Kawabata, Hisako Miki, Yugo Himuro, Masayuki Yoshikawa, Hisashi Matsuda. Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna). Bioorganic & medicinal chemistry letters. 2015 Jul; 25(13):2702-6. doi: 10.1016/j.bmcl.2015.04.052. [PMID: 25987378]
  • Paula García, Ricardo L E Furlan. Multiresponse Optimisation Applied to the Development of a TLC Autography for the Detection of Tyrosinase Inhibitors. Phytochemical analysis : PCA. 2015 Jul; 26(4):287-92. doi: 10.1002/pca.2562. [PMID: 25808984]
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  • Jin-Dan Zhang, Lida Han, Shijuan Yan, Chun-Ming Liu. The non-metabolizable glucose analog D-glucal inhibits aflatoxin biosynthesis and promotes kojic acid production in Aspergillus flavus. BMC microbiology. 2014 Apr; 14(?):95. doi: 10.1186/1471-2180-14-95. [PMID: 24742119]
  • Montra Srisayam, Natthida Weerapreeyakul, Sahapat Barusrux, Waraporn Tanthanuch, Kanjana Thumanu. Application of FTIR microspectroscopy for characterization of biomolecular changes in human melanoma cells treated by sesamol and kojic acid. Journal of dermatological science. 2014 Mar; 73(3):241-50. doi: 10.1016/j.jdermsci.2013.11.002. [PMID: 24296160]
  • Noureddin El-Boulifi, Siti Efliza Ashari, Marta Serrano, Jose Aracil, Mercedes Martínez. Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid. Enzyme and microbial technology. 2014 Feb; 55(?):128-32. doi: 10.1016/j.enzmictec.2013.10.009. [PMID: 24411455]
  • Yan Wang, Marcus J Curtis-Long, Byong Won Lee, Heung Joo Yuk, Dae Wook Kim, Xue Fei Tan, Ki Hun Park. Inhibition of tyrosinase activity by polyphenol compounds from Flemingia philippinensis roots. Bioorganic & medicinal chemistry. 2014 Feb; 22(3):1115-20. doi: 10.1016/j.bmc.2013.12.047. [PMID: 24412339]
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