Tropolone (BioDeep_00000396908)

Main id: BioDeep_00000010734

 

PANOMIX_OTCML-2023 Toxin


代谢物信息卡片


InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9

化学式: C7H6O2 (122.0367776)
中文名称: 环庚三烯酚酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C(C(=O)C=C1)O
InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

描述信息

Tropolone is a cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii. It has a role as a bacterial metabolite, a toxin and a fungicide. It is a cyclic ketone, an enol and an alpha-hydroxy ketone. It derives from a hydride of a cyclohepta-1,3,5-triene.
A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).
A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.
Tropolone, a ?tropone derivative with a?hydroxyl group?in the 2-position, is a precursor?of manyazulene derivatives such as?methyl 2-methylazulene-1-carboxylate[1]. Tropolone is a potent inhibitor of mushroom tyrosinase with a IC50 of 0.4 μM, and the inhibition can be reversed by dialysis or by excess CU2+[2].

同义名列表

27 个代谢物同义名

InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9; (2E,4Z,6Z)-2-hydroxycyclohepta-2,4,6-trienone; 4-08-00-00159 (Beilstein Handbook Reference); 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-; 2-Hydroxy-2,4,6-cycloheptatriene-1-one; 2-hydroxy-2,4,6-cycloheptatrien -1-one; 2-Hydroxy-2,4,6-cycloheptatrien-1-one; 2-hydroxycyclohepta-2,4,6-trien-1-one; 2,6-Cycloheptatrien-1-one, 2-hydroxy-; 2-Hydroxy-cyclohepta-2,4,6-trienone; 2-Hydroxy-2,4,6-cycloheptatrienone; 2-Hydroxycyclohepta-2,4,6-trienone; Tropolone, purum, >=98.0\\% (GC); TROPOLONE [WHO-DD]; .ALPHA.-TROPOLONE; 2-Hydroxytropone; TROPOLONE [INCI]; UNII-7L6DL16P1T; Purpurocatechol; Tropolone, 98\\%; TROPOLONE [MI]; Tox21_202924; NCI60_041986; Tropomyosins; 7L6DL16P1T; Tropolone; 0TR



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(6)

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)

1 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

  • Yue Jin, Zongxin Guo, Huilin Zhu, Zixuan Zhang, Xiaowen Jiang, Yiren Yang, Pengyu Liu, Yu Yang, Miao Wang, Huiyuan Gao. Discovery of potential components characteristic by conjugated enone from the branches and leaves of Croton lauioides with anti-neuroinflammatory activity via regulating the NF-κB pathway. Bioorganic chemistry. 2024 May; 146(?):107301. doi: 10.1016/j.bioorg.2024.107301. [PMID: 38522392]
  • Sylwia Jafra, Magdalena Jabłońska, Tomasz Maciąg, Marta Matuszewska, Marcin Borowicz, Michał Prusiński, Wioletta Żmudzińska, Marcel Thiel, Paulina Czaplewska, Dorota M Krzyżanowska, Robert Czajkowski. An iron fist in a velvet glove: The cooperation of a novel pyoverdine from Pseudomonas donghuensis P482 with 7-hydroxytropolone is pivotal for its antibacterial activity. Environmental microbiology. 2024 Jan; 26(1):e16559. doi: 10.1111/1462-2920.16559. [PMID: 38151794]
  • Hongxing Tang, Kejun He, Kun Zhao, Chen Zheng, Weichi Wu, Weilin Jin, Lixuan Yang, Baoshu Xie. Protective effects of Hinokitiol on neuronal ferroptosis by activating the KEAP1/NRF-2/HO-1 pathway in traumatic brain injury. Journal of neurotrauma. 2023 Nov; ?(?):. doi: 10.1089/neu.2023.0150. [PMID: 37962273]
  • Zhiping Che, Yibo Liu, Luyao Chen, Puhou Xing, Xiangdong Li, Xiaobo Huang, Shengming Liu, Genqiang Chen, Xiaomin Lin, Yuee Tian. Synthesis of Hinokitiol Sulfonate Derivatives and Their Anti-Oomycete and Nematicidal Activities. Chemistry & biodiversity. 2022 Sep; 19(9):e202200580. doi: 10.1002/cbdv.202200580. [PMID: 35975883]
  • Yamini Chelpuri, Shivakumar Pabbathi, Gopala Reddy Alla, Ravi Kumar Yadala, Mounika Kamishetti, Anil Kumar Banothu, Ramya Boinepally, Kala Kumar Bharani, Amit Khurana. Tropolone derivative hinokitiol ameliorates cerulein-induced acute pancreatitis in mice. International immunopharmacology. 2022 Aug; 109(?):108915. doi: 10.1016/j.intimp.2022.108915. [PMID: 35679663]
  • Biao Wang, Bo He, Tianyu Chen, Hao Li, Liyifan Chen, Yiliang Chen, Kailin Tian, Kun Yang, Danyu Shen, Wei Yan, Yonghao Ye. Discovery of Tropolone Stipitaldehyde as a Potential Agent for Controlling Phytophthora Blight and Its Action Mechanism Research. Journal of agricultural and food chemistry. 2022 Jul; 70(28):8693-8703. doi: 10.1021/acs.jafc.2c03163. [PMID: 35793537]
  • Xuan Tao, Lu Zhang, Liubing Du, Kai Lu, Zhennan Zhao, Yanxuan Xie, Xiaobo Li, Shuxiang Huang, Pei-Hui Wang, Ji-An Pan, Wei Xia, Jun Dai, Zong-Wan Mao. Inhibition of SARS-CoV-2 replication by zinc gluconate in combination with hinokitiol. Journal of inorganic biochemistry. 2022 06; 231(?):111777. doi: 10.1016/j.jinorgbio.2022.111777. [PMID: 35255411]
  • Christopher DeLaney, Yan Sheng, D Chase Pectol, Erol Vantansever, Hanyuan Zhang, Nattamai Bhuvanesh, Isaiah Salas, Wenshe R Liu, Carol F Fierke, Marcetta Y Darensbourg. Zinc thiotropolone combinations as inhibitors of the SARS-CoV-2 main protease. Dalton transactions (Cambridge, England : 2003). 2021 Sep; 50(35):12226-12233. doi: 10.1039/d1dt02499j. [PMID: 34396374]
  • Jae Sung Park, Keebeom Ko, Seong-Hwan Kim, Jae Kyun Lee, Jin-Soo Park, Keunwan Park, Mi Ri Kim, Kyungsu Kang, Dong-Chan Oh, Sun Yeou Kim, Silvia Yumnam, Hak Cheol Kwon, Jongheon Shin. Tropolone-Bearing Sesquiterpenes from Juniperus chinensis: Structures, Photochemistry and Bioactivity. Journal of natural products. 2021 07; 84(7):2020-2027. doi: 10.1021/acs.jnatprod.1c00321. [PMID: 34236881]
  • Ge Zou, Qi Tan, Yan Chen, Wencong Yang, Zhenming Zang, Hongming Jiang, Shenyu Chen, Bo Wang, Zhigang She. Furobenzotropolones A, B and 3-Hydroxyepicoccone B with Antioxidative Activity from Mangrove Endophytic Fungus Epicoccum nigrum MLY-3. Marine drugs. 2021 Jul; 19(7):. doi: 10.3390/md19070395. [PMID: 34356820]
  • Marketa Houdkova, Aishwarya Chaure, Ivo Doskocil, Jaroslav Havlik, Ladislav Kokoska. New Broth Macrodilution Volatilization Method for Antibacterial Susceptibility Testing of Volatile Agents and Evaluation of Their Toxicity Using Modified MTT Assay In Vitro. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144179. [PMID: 34299454]
  • Yancho Zarev, Pavlinka Popova, Kenn Foubert, Iliana Ionkova, Luc Pieters. Comparative LC-MS analysis of tropolone alkaloids from in vitro cultures and native sources of Gloriosa superba by Kendrick mass defect plots. Phytochemical analysis : PCA. 2021 Jul; 32(4):446-456. doi: 10.1002/pca.2992. [PMID: 32888246]
  • Marta Matuszewska, Tomasz Maciąg, Magdalena Rajewska, Aldona Wierzbicka, Sylwia Jafra. The carbon source-dependent pattern of antimicrobial activity and gene expression in Pseudomonas donghuensis P482. Scientific reports. 2021 05; 11(1):10994. doi: 10.1038/s41598-021-90488-w. [PMID: 34040089]
  • Saideng Lu, Yu Song, Rongjin Luo, Shuai Li, Gaocai Li, Kun Wang, Zhiwei Liao, Bingjin Wang, Wencan Ke, Qian Xiang, Chao Chen, Xinghuo Wu, Yukun Zhang, Li Ling, Cao Yang. Ferroportin-Dependent Iron Homeostasis Protects against Oxidative Stress-Induced Nucleus Pulposus Cell Ferroptosis and Ameliorates Intervertebral Disc Degeneration In Vivo. Oxidative medicine and cellular longevity. 2021; 2021(?):6670497. doi: 10.1155/2021/6670497. [PMID: 33628376]
  • Ba X Hoang, Bo Han. A possible application of hinokitiol as a natural zinc ionophore and anti-infective agent for the prevention and treatment of COVID-19 and viral infections. Medical hypotheses. 2020 Dec; 145(?):110333. doi: 10.1016/j.mehy.2020.110333. [PMID: 33045596]
  • Qin-Ge Ma, Rong-Rui Wei, Xiao-Dong Zhang, Zhi-Pei Sang, Jiang-Hong Dong, Qi-Xin Lu, Hao-Feng Huang, Dong-Mei Guo, Lin Jiang. Tropolone derivatives with hepatoprotective and antiproliferative activities from the aerial parts of Chenopodium album Linn. Fitoterapia. 2020 Oct; 146(?):104733. doi: 10.1016/j.fitote.2020.104733. [PMID: 32979464]
  • Mohammad Azadbakht, Ali Davoodi, Seyed Jalal Hosseinimehr, Masoud Keighobadi, Mahdi Fakhar, Reza Valadan, Roghiyeh Faridnia, Saeed Emami, Masoud Azadbakht, Adel Bakhtiyari. Tropolone alkaloids from Colchicum kurdicum (Bornm.) Stef. (Colchicaceae) as the potent novel antileishmanial compounds; purification, structure elucidation, antileishmanial activities and molecular docking studies. Experimental parasitology. 2020 Jun; 213(?):107902. doi: 10.1016/j.exppara.2020.107902. [PMID: 32353376]
  • Yueh-Jung Wu, Wei-Jie Hsu, Li-Hsien Wu, Huei-Pu Liou, Christian Ronquillo Pangilinan, Yu-Chang Tyan, Che-Hsin Lee. Hinokitiol reduces tumor metastasis by inhibiting heparanase via extracellular signal-regulated kinase and protein kinase B pathway. International journal of medical sciences. 2020; 17(3):403-413. doi: 10.7150/ijms.41177. [PMID: 32132875]
  • Toshihito Isono, Hisanori Domon, Kosuke Nagai, Tomoki Maekawa, Hikaru Tamura, Takumi Hiyoshi, Katsunori Yanagihara, Eiji Kunitomo, Shoji Takenaka, Yuichiro Noiri, Yutaka Terao. Treatment of severe pneumonia by hinokitiol in a murine antimicrobial-resistant pneumococcal pneumonia model. PloS one. 2020; 15(10):e0240329. doi: 10.1371/journal.pone.0240329. [PMID: 33057343]
  • Jungwook Park, Hyun-Hee Lee, Hyejung Jung, Young-Su Seo. Transcriptome analysis to understand the effects of the toxoflavin and tropolone produced by phytopathogenic Burkholderia on Escherichia coli. Journal of microbiology (Seoul, Korea). 2019 Sep; 57(9):781-794. doi: 10.1007/s12275-019-9330-1. [PMID: 31452043]
  • Huong T M Nguyen, Nga T Vo, Suong T M Huynh, Lien T M Do, Thammarat Aree, Santi Tip-Pyang, Cam-Tu D Phan, Nguyen T Trung, Phung K P Nguyen. A sesquiterpenoid tropolone and 1,2,3,4-tetrahydronaphthalene derivatives from Olax imbricata roots. Fitoterapia. 2019 Jan; 132(?):1-6. doi: 10.1016/j.fitote.2018.11.007. [PMID: 30439445]
  • Xiaoyu Liu, Xiaoyan Fan, Haruna Matsumoto, Yanxia Nie, Zhimin Sha, Kunpeng Yi, Jiuyue Pan, Yuan Qian, Mengchao Cao, Yihu Wang, Guonian Zhu, Mengcen Wang. Biotoxin Tropolone Contamination Associated with Nationwide Occurrence of Pathogen Burkholderia plantarii in Agricultural Environments in China. Environmental science & technology. 2018 05; 52(9):5105-5114. doi: 10.1021/acs.est.7b05915. [PMID: 29589436]
  • Joseph J Karchesy, Rick G Kelsey, M P González-Hernández. Yellow-Cedar, Callitropsis (Chamaecyparis) nootkatensis, Secondary Metabolites, Biological Activities, and Chemical Ecology. Journal of chemical ecology. 2018 May; 44(5):510-524. doi: 10.1007/s10886-018-0956-y. [PMID: 29654493]
  • Nobuya Magori, Tsugumi Fujita, Eiichi Kumamoto. Hinokitiol inhibits compound action potentials in the frog sciatic nerve. European journal of pharmacology. 2018 Jan; 819(?):254-260. doi: 10.1016/j.ejphar.2017.12.014. [PMID: 29225186]
  • Lihong Zhang, Yang Peng, Ivan P Uray, Jianfeng Shen, Lulu Wang, Xiangdong Peng, Powel H Brown, Wei Tu, Guang Peng. Natural product β-thujaplicin inhibits homologous recombination repair and sensitizes cancer cells to radiation therapy. DNA repair. 2017 12; 60(?):89-101. doi: 10.1016/j.dnarep.2017.10.009. [PMID: 29112893]
  • Eva Christina Sonnenschein, Christopher Broughton William Phippen, Kristian Fog Nielsen, Ramona Valentina Mateiu, Jette Melchiorsen, Lone Gram, Jörg Overmann, Heike M Freese. Phaeobacter piscinae sp. nov., a species of the Roseobacter group and potential aquaculture probiont. International journal of systematic and evolutionary microbiology. 2017 Nov; 67(11):4559-4564. doi: 10.1099/ijsem.0.002331. [PMID: 28984543]
  • Ammar Kurdi, Matthias Cleenewerck, Christel Vangestel, Sophie Lyssens, Wim Declercq, Jean-Pierre Timmermans, Sigrid Stroobants, Koen Augustyns, Guido R Y De Meyer, Pieter Van Der Veken, Wim Martinet. ATG4B inhibitors with a benzotropolone core structure block autophagy and augment efficiency of chemotherapy in mice. Biochemical pharmacology. 2017 08; 138(?):150-162. doi: 10.1016/j.bcp.2017.06.119. [PMID: 28642033]
  • Huijuan Guo, René Benndorf, Daniel Leichnitz, Jonathan L Klassen, John Vollmers, Helmar Görls, Matthias Steinacker, Christiane Weigel, Hans-Martin Dahse, Anne-Kristin Kaster, Z Wilhelm de Beer, Michael Poulsen, Christine Beemelmanns. Isolation, Biosynthesis and Chemical Modifications of Rubterolones A-F: Rare Tropolone Alkaloids from Actinomadura sp. 5-2. Chemistry (Weinheim an der Bergstrasse, Germany). 2017 Jul; 23(39):9338-9345. doi: 10.1002/chem.201701005. [PMID: 28463423]
  • Beulaja Manikandan, Manikandan Ramar, Thiagarajan Raman, Mullainadhan Periasamy, Arumugam Munusamy. Purification and characterisation of a pronase-inducible lectin isolated from human serum. International journal of biological macromolecules. 2017 Jun; 99(?):443-453. doi: 10.1016/j.ijbiomac.2017.02.022. [PMID: 28212932]
  • Jung Seon Seo, Young Ha Choi, Ji Wook Moon, Hyeon Soo Kim, Sun-Hwa Park. Hinokitiol induces DNA demethylation via DNMT1 and UHRF1 inhibition in colon cancer cells. BMC cell biology. 2017 02; 18(1):14. doi: 10.1186/s12860-017-0130-3. [PMID: 28241740]
  • Yuki Naito, Yutaka Yoshikawa, Michiko Shintani, Shingo Kamoshida, Naemi Kajiwara, Hiroyuki Yasui. Anti-hyperglycemic Effect of Long-Term Bis(hinokitiolato)zinc Complex ([Zn(hkt)2]) Ingestion on Insulin Resistance and Pancreatic Islet Cells Protection in Type 2 Diabetic KK-Ay Mice. Biological & pharmaceutical bulletin. 2017; 40(3):318-326. doi: 10.1248/bpb.b16-00797. [PMID: 28250273]
  • Koki Fujita, Ryo Kambe, Ransika De Alwis, Tatsuya Yagi, Yuji Tsutsumi. Airborne Monoterpenes Emitted from a Cupressus lusitanica Cell Culture Induce a Signaling Cascade that Produces β-Thujaplicin. Journal of chemical ecology. 2016 Aug; 42(8):814-820. doi: 10.1007/s10886-016-0739-2. [PMID: 27596215]
  • Shunpei Miwa, Eri Kihira, Akinori Yoshioka, Kaoru Nakasone, Sho Okamoto, Masaki Hatano, Masayuki Igarashi, Yoko Eguchi, Akinori Kato, Natsuko Ichikawa, Mitsuo Sekine, Nobuyuki Fujita, Yu Kanesaki, Hirofumi Yoshikawa, Ryutaro Utsumi. Identification of the Three Genes Involved in Controlling Production of a Phytotoxin Tropolone in Burkholderia plantarii. Journal of bacteriology. 2016 06; 198(11):1604-1609. doi: 10.1128/jb.01028-15. [PMID: 27002128]
  • Yijun Yan, Ya-Tuan Ma, Jing Yang, Geoff P Horsman, Dan Luo, Xu Ji, Sheng-Xiong Huang. Tropolone Ring Construction in the Biosynthesis of Rubrolone B, a Cationic Tropolone Alkaloid from Endophytic Streptomyces. Organic letters. 2016 Mar; 18(6):1254-7. doi: 10.1021/acs.orglett.6b00074. [PMID: 26926531]
  • Yun Chen, Ling Zeng, Wen Xiong, Meiyun Song, Hongxu Du, Yixuan Wang, Ke Ming, Yi Wu, Deyun Wang, Yuanliang Hu, Jiaguo Liu. Anti-duck virus hepatitis mechanisms of Bush Sophora Root polysaccharide and its sulfate verified by intervention experiments. Virus research. 2015 Jun; 204(?):58-67. doi: 10.1016/j.virusres.2015.04.013. [PMID: 25901935]
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