Atranorin (BioDeep_00000366205)

 

Secondary id: BioDeep_00000238880

natural product PANOMIX_OTCML-2023


代谢物信息卡片


methyl 1-(3-formyl-2,4-dihydroxy-6-methylphenylcarbonyloxy)-3-hydroxy-2,5-dimethyl-4-benzenecarboxylate

化学式: C19H18O8 (374.1001628)
中文名称: 黑茶渍素, 荔枝素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 55.13%

分子结构信息

SMILES: CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O
InChI: InChI=1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3

描述信息

Atranorin is a carbonyl compound.
Atranorin is a natural product found in Candelaria concolor, Loxospora elatina, and other organisms with data available.
Atranorin is a lichen secondary metabolite. Atranorin inhibits lung cancer cell motility and tumorigenesis by affecting AP-1, Wnt, and STAT signaling and suppressing RhoGTPase activity[1][2].
Atranorin is a lichen secondary metabolite. Atranorin inhibits lung cancer cell motility and tumorigenesis by affecting AP-1, Wnt, and STAT signaling and suppressing RhoGTPase activity[1][2].
Atranorin is a lichen secondary metabolite. Atranorin inhibits lung cancer cell motility and tumorigenesis by affecting AP-1, Wnt, and STAT signaling and suppressing RhoGTPase activity[1][2].

同义名列表

34 个代谢物同义名

methyl 1-(3-formyl-2,4-dihydroxy-6-methylphenylcarbonyloxy)-3-hydroxy-2,5-dimethyl-4-benzenecarboxylate; Benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate; Benzoic acid,3-formyl-2,4-dihydroxy-6-methyl-,3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-beta-resorcylate; Isophthalaldehydic acid,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate; 3-formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate #; (3-hydroxy-4-methoxycarbonyl-2,5-dimethyl-phenyl) 3-formyl-2,4-dihydroxy-6-methyl-benzoate; Benzoic acid,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate; 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate; Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy- 3,6-dimethyl-benzoate; YLOYKYXNDHOHHT-UHFFFAOYSA-N; atranorin monopotassium; Spectrum5_000380; Spectrum3_001716; Spectrum4_001700; Spectrum2_001749; Antranoric acid; Atranoric acid; ATRANORIN [MI]; Parmelin acid; DivK1c_006335; Usnarin acid; KBio2_005759; KBio3_002552; KBio2_003191; KBio2_000623; KBio1_001279; Atranorine; Atranorin; Parmelin; Usnarin



数据库引用编号

12 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)

236 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

  • Zhentian Ni, Xiaoli Nie, Hairong Zhang, Lingquan Wang, Zixiang Geng, Xiling Du, Haiyang Qian, Wentao Liu, Te Liu. Atranorin driven by nano materials SPION lead to ferroptosis of gastric cancer stem cells by weakening the mRNA 5-hydroxymethylcytidine modification of the Xc-/GPX4 axis and its expression. International journal of medical sciences. 2022; 19(11):1680-1694. doi: 10.7150/ijms.73701. [PMID: 36237989]
  • Robert Q Thompson, Daniel Katz, Brendan Sheehan. Chemical comparison of Prunus africana bark and pygeum products marketed for prostate health. Journal of pharmaceutical and biomedical analysis. 2019 Jan; 163(?):162-169. doi: 10.1016/j.jpba.2018.10.004. [PMID: 30316061]
  • Haroon Khan, Kannan R R Rengasamy, Aini Pervaiz, Seyed Mohammad Nabavi, Atanas G Atanasov, Mohammad A Kamal. Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation. European journal of medicinal chemistry. 2018 Jun; 153(?):2-28. doi: 10.1016/j.ejmech.2017.12.059. [PMID: 29329790]
  • Yoshinori Asakawa, Agnieszka Ludwiczuk. Chemical Constituents of Bryophytes: Structures and Biological Activity. Journal of natural products. 2018 03; 81(3):641-660. doi: 10.1021/acs.jnatprod.6b01046. [PMID: 29019405]
  • Michal Goga, Sebastian J Antreich, Martin Bačkor, Wolfram Weckwerth, Ingeborg Lang. Lichen secondary metabolites affect growth of Physcomitrella patens by allelopathy. Protoplasma. 2017 May; 254(3):1307-1315. doi: 10.1007/s00709-016-1022-7. [PMID: 27645140]
  • Vertika Shukla, D K Patel, Rajesh Bajpai, Manoj Semwal, D K Upreti. Ecological implication of variation in the secondary metabolites in Parmelioid lichens with respect to altitude. Environmental science and pollution research international. 2016 Jan; 23(2):1391-7. doi: 10.1007/s11356-015-5311-z. [PMID: 26370809]
  • Arianna Pompilio, Stefano Pomponio, Valentina Di Vincenzo, Valentina Crocetta, Marcello Nicoletti, Marisa Piovano, Juan A Garbarino, Giovanni Di Bonaventura. Antimicrobial and antibiofilm activity of secondary metabolites of lichens against methicillin-resistant Staphylococcus aureus strains from cystic fibrosis patients. Future microbiology. 2013 Feb; 8(2):281-92. doi: 10.2217/fmb.12.142. [PMID: 23374132]
  • Denis Zofou, Mathieu Tene, Pierre Tane, Vincent P K Titanji. Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain. Parasitology research. 2012 Feb; 110(2):539-44. doi: 10.1007/s00436-011-2519-9. [PMID: 21814840]
  • Antonino De Natale, Antonino Pollio. A forgotten collection: the Libyan ethnobotanical exhibits (1912-14) by A. Trotter at the Museum O. Comes at the University Federico II in Naples, Italy. Journal of ethnobiology and ethnomedicine. 2012 Jan; 8(?):4. doi: 10.1186/1746-4269-8-4. [PMID: 22264313]
  • Nedeljko T Manojlovic, Perica J Vasiljevic, Pavle Z Maskovic, Marina Juskovic, Gordana Bogdanovic-Dusanovic. Chemical Composition, Antioxidant, and Antimicrobial Activities of Lichen Umbilicaria cylindrica (L.) Delise (Umbilicariaceae). Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):452431. doi: 10.1155/2012/452431. [PMID: 21915186]
  • Ju-Hyun Sung, Jeong-Woo Chon, Mi-Ae Lee, Jin-Kyung Park, Jeong-Taek Woo, Yoo Kyoung Park. The anti-obesity effect of Lethariella cladonioides in 3T3-L1 cells and obese mice. Nutrition research and practice. 2011 Dec; 5(6):503-10. doi: 10.4162/nrp.2011.5.6.503. [PMID: 22259674]
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  • Denis Zofou, Archile Bernabe Ouambo Kengne, Mathieu Tene, Moses N Ngemenya, Pierre Tane, Vincent P K Titanji. In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae). Parasitology research. 2011 Jun; 108(6):1383-90. doi: 10.1007/s00436-011-2363-y. [PMID: 21487780]
  • Christopher J Johnson, James P Bennett, Steven M Biro, Juan Camilo Duque-Velasquez, Cynthia M Rodriguez, Richard A Bessen, Tonie E Rocke. Degradation of the disease-associated prion protein by a serine protease from lichens. PloS one. 2011 May; 6(5):e19836. doi: 10.1371/journal.pone.0019836. [PMID: 21589935]
  • Mayurika Goel, Prem Dureja, Archna Rani, Prem L Uniyal, Hartmut Laatsch. Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl. Journal of agricultural and food chemistry. 2011 Mar; 59(6):2299-307. doi: 10.1021/jf1049613. [PMID: 21351753]
  • Jozef Kováčik, Bořivoj Klejdus, Martin Bačkor, František Stork, Josef Hedbavny. Physiological responses of root-less epiphytic plants to acid rain. Ecotoxicology (London, England). 2011 Mar; 20(2):348-57. doi: 10.1007/s10646-010-0585-x. [PMID: 21161375]
  • Lidianne Mayra Lopes Campêlo, Antonia Amanda C de Almeida, Rizângela L Mendes de Freitas, Gilberto Santos Cerqueira, Geane Felix de Sousa, Gláucio Barros Saldanha, Chistiane Mendes Feitosa, Rivelilson Mendes de Freitas. Antioxidant and antinociceptive effects of Citrus limon essential oil in mice. Journal of biomedicine & biotechnology. 2011; 2011(?):678673. doi: 10.1155/2011/678673. [PMID: 21660140]
  • Tatjana Mitrović, Slaviša Stamenković, Vladimir Cvetković, Svetlana Tošić, Milan Stanković, Ivana Radojević, Olgica Stefanović, Ljiljana Comić, Dragana Dačić, Milena Curčić, Snežana Marković. Antioxidant, antimicrobial and antiproliferative activities of five lichen species. International journal of molecular sciences. 2011; 12(8):5428-48. doi: 10.3390/ijms12085428. [PMID: 21954369]
  • Rosana S Siqueira, Leonardo R Bonjardim, Adriano A S Araújo, Bruno E S Araújo, Marcélia G D Melo, Marília G B Oliveira, Daniel P Gelain, Francilene A Silva, Josimari M DeSantana, Ricardo L C Albuquerque-Júnior, Ricardo F Rocha, José C F Moreira, Angelo R Antoniolli, Lucindo J Quintans-Júnior. Antinociceptive activity of atranorin in mice orofacial nociception tests. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2010 Sep; 65(9-10):551-61. doi: 10.1515/znc-2010-9-1004. [PMID: 21138055]
  • Knut Asbjørn Solhaug, Per Larsson, Yngvar Gauslaa. Light screening in lichen cortices can be quantified by chlorophyll fluorescence techniques for both reflecting and absorbing pigments. Planta. 2010 Apr; 231(5):1003-11. doi: 10.1007/s00425-010-1103-3. [PMID: 20135325]
  • N K Honda, F R Pavan, R G Coelho, S R de Andrade Leite, A C Micheletti, T I B Lopes, M Y Misutsu, A Beatriz, R L Brum, C Q F Leite. Antimycobacterial activity of lichen substances. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Apr; 17(5):328-32. doi: 10.1016/j.phymed.2009.07.018. [PMID: 19683421]
  • Iracilda Z Carlos, Marcela B Quilles, Camila B A Carli, Danielle C G Maia, Fernanda P Benzatti, Thiago I B Lopes, Aline S Gianini, Rosenei L Brum, Wagner Vilegas, Lourdes C dos Santos, Neli K Honda. Lichen metabolites modulate hydrogen peroxide and nitric oxide in mouse macrophages. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 Sep; 64(9-10):664-72. doi: 10.1515/znc-2009-9-1010. [PMID: 19957434]
  • Tim S Bugni, Cynthia D Andjelic, Ann R Pole, Prem Rai, Chris M Ireland, Louis R Barrows. Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation. Fitoterapia. 2009 Jul; 80(5):270-3. doi: 10.1016/j.fitote.2009.03.003. [PMID: 19289158]
  • Changon Seo, Jae Hak Sohn, Jong Seog Ahn, Joung Han Yim, Hong Kum Lee, Hyuncheol Oh. Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum. Bioorganic & medicinal chemistry letters. 2009 May; 19(10):2801-3. doi: 10.1016/j.bmcl.2009.03.108. [PMID: 19362837]
  • Andrea Nardelli, Elena Giménez-Arnau, Guillaume Bernard, Jean-Pierre Lepoittevin, An Goossens. Is a low content in atranol/chloroatranol safe in oak moss-sensitized individuals?. Contact dermatitis. 2009 Feb; 60(2):91-5. doi: 10.1111/j.1600-0536.2008.01478.x. [PMID: 19207379]
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  • Charles Mutai, Dennis Abatis, Constantinos Vagias, Dimitri Moreau, Christos Roussakis, Vassilios Roussis. Lupane triterpenoids from Acacia mellifera with cytotoxic activity. Molecules (Basel, Switzerland). 2007 May; 12(5):1035-44. doi: 10.3390/12051035. [PMID: 17873838]
  • Markus Hauck, Siegfried Huneck. Lichen substances affect metal adsorption in Hypogymnia physodes. Journal of chemical ecology. 2007 Jan; 33(1):219-23. doi: 10.1007/s10886-006-9225-6. [PMID: 17136464]
  • Satoko Arakawa-Kobayashi, Takashi Kobayashi, Mitsuyasu Hasebe, Toku Kanaseki. Identification of crystalline material found in the thallus of the lichen, Myelochroa leucotyliza. Journal of structural biology. 2004 Jun; 146(3):393-400. doi: 10.1016/j.jsb.2004.01.015. [PMID: 15099580]
  • Satoko Arakawa-Kobayashi, Toku Kanaseki. A study of lipid secretion from the lichen symbionts, ascomycetous fungus Myelochroa leucotyliza and green alga Trebouxia sp. Journal of structural biology. 2004 Jun; 146(3):401-15. doi: 10.1016/j.jsb.2004.01.016. [PMID: 15099581]
  • Meral Yilmaz, Ayşen Ozdemir Türk, Turgay Tay, Merih Kivanç. The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Mar; 59(3-4):249-54. doi: 10.1515/znc-2004-3-423. [PMID: 15241936]
  • Guillaume Bernard, Elena Giménez-Arnau, Suresh Chandra Rastogi, Siri Heydorn, Jeanne Duus Johansen, Torkil Menné, An Goossens, Klaus Andersen, Jean-Pierre Lepoittevin. Contact allergy to oak moss: search for sensitizing molecules using combined bioassay-guided chemical fractionation, GC-MS, and structure-activity relationship analysis. Archives of dermatological research. 2003 Nov; 295(6):229-35. doi: 10.1007/s00403-003-0426-3. [PMID: 13680271]
  • F J Toledo Marante, A García Castellano, F Estévez Rosas, J Quintana Aguiar, J Bermejo Barrera. Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity. Journal of chemical ecology. 2003 Sep; 29(9):2049-71. doi: 10.1023/a:1025682318001. [PMID: 14584675]
  • C Vicente, B Fontaniella, A M Millanes, B Sebastián, M E Legaz. Enzymatic production of atranorin: a component of the oak moss absolute by immobilized lichen cells. International journal of cosmetic science. 2003 Apr; 25(1-2):25-9. doi: 10.1046/j.1467-2494.2003.00169.x. [PMID: 18494879]
  • M Blanch, Y Blanco, B Fontaniella, M E Legaz, C Vicente. Production of phenolics by immobilized cells of the lichen Pseudevernia furfuracea: the role of epiphytic bacteria. International microbiology : the official journal of the Spanish Society for Microbiology. 2001 Jun; 4(2):89-92. doi: 10.1007/s101230100019. [PMID: 11770830]
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