Polygodial (BioDeep_00000000620)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (1R-(1alpha,4abeta,8aalpha))-

化学式: C15H22O2 (234.1619712)
中文名称: 蓼二醛, 水蓼二醛
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.87%

分子结构信息

SMILES: CC1(C)CCCC2(C)C(C=O)C(C=O)=CCC12
InChI: InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1

描述信息

Polygodial is an aldehyde.
Polygodial is a natural product found in Zygogynum pancheri, Zygogynum acsmithii, and other organisms with data available.
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
Polygodial (Poligodial) is an antifungal potentiator[1]. Polygodial is a sesquiterpene with anti-hyperalgesic properties[2].

同义名列表

28 个代谢物同义名

1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (1R-(1alpha,4abeta,8aalpha))-; 1,2-NAPHTHALENEDICARBOXALDEHYDE, 1,4,4A,5,6,7,8,8A-OCTAHYDRO-5,5,8A-TRIMETHYL-, (1R,4AS,8AS)-REL-; 1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (1R,4aS,8aS)-; 1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (2R,4aS,8aS)-; 1,2-Naphthalenedicarboxaldehyde, 1alpha,4,4aalpha,5,6,7,8,8a-octahydro-5,5,8abata-trimethyl-; 1,2-Naphthalenedicarboxaldehyde,1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-, (1R,4aS,8aS)-; (1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde; (1r,4as,8as)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde; (1R,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde; (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde; 1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde; AZJUJOFIHHNCSV-KCQAQPDRSA-N; Drim-7-ene-11,12-dial; Poligodial;Tadeonal; QUIRAL TADEODAL; UNII-A00RAV0W57; UNII-5FAF7T66M7; (-)-Polygodial; epipolygodial; NCI60_003460; (-)-Tadeonal; Poligodial; A00RAV0W57; Polygodial; 5FAF7T66M7; Tadeodal; Tadeonal; Polygodial



数据库引用编号

20 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)

121 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

  • Min-Woo Lee, Dong-Ho Lee, Il Nam, Jae-Woo Lee, Min-Jung Huh, Il-Kwon Park. Acaricidal and Insecticidal Activities of Essential Oils and Constituents of Tasmannia lanceolata (Poir.) A.C.Sm. (Canellales: Winteraceae) Against Tetranychus urticae Koch (Trombidiformes: Tetranychidae) and Myzus persicae Sulzer (Hemiptera: Aphididae). Journal of economic entomology. 2023 04; 116(2):447-455. doi: 10.1093/jee/toad011. [PMID: 36708054]
  • Sahla Belhadj, Henda Keskes, Cécile Apel, Fanny Roussi, Marc Litaudon, Olfa Hentati, Noureddine Allouche. Anti-diabetic and lipid-lowering effects of drimane sesquiterpenoids isolated from Zygogynum pancheri. Chemico-biological interactions. 2020 Oct; 330(?):109167. doi: 10.1016/j.cbi.2020.109167. [PMID: 32603660]
  • Kurt Debruille, Jason A Smith, Joselito P Quirino. Pressurized Hot Water Extraction and Capillary Electrophoresis for Green and Fast Analysis of Useful Metabolites in Plants. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132349. [PMID: 31247895]
  • Alessandra Russo, Venera Cardile, Adriana C E Graziano, Rosanna Avola, Ivan Montenegro, Mauricio Cuellar, Joan Villena, Alejandro Madrid. Antigrowth activity and induction of apoptosis in human melanoma cells by Drymis winteri forst extract and its active components. Chemico-biological interactions. 2019 May; 305(?):79-85. doi: 10.1016/j.cbi.2019.03.029. [PMID: 30935903]
  • Giulia Elisa Guimarães Gonçalves, Thiago Rahal Morais, Kaio de Souza Gomes, Thais Alves Costa-Silva, Andre Gustavo Tempone, João Henrique Ghilardi Lago, Luciano Caseli. Antitrypanosomal activity of epi-polygodial from Drimys brasiliensis and its effects in cellular membrane models at the air-water interface. Bioorganic chemistry. 2019 03; 84(?):186-191. doi: 10.1016/j.bioorg.2018.11.048. [PMID: 30502630]
  • Maoxuan Liu, Purity Kipanga, Anh Hung Mai, Ineke Dhondt, Bart P Braeckman, Wim De Borggraeve, Walter Luyten. Bioassay-guided isolation of three anthelmintic compounds from Warburgia ugandensis Sprague subspecies ugandensis, and the mechanism of action of polygodial. International journal for parasitology. 2018 09; 48(11):833-844. doi: 10.1016/j.ijpara.2017.11.009. [PMID: 30031002]
  • Diogo Gomes Garcia, Cassiano Felippe Gonçalves-de-Albuquerque, Camila Ignácio da Silva, Robert Kiss, Ramesh Dasari, Sunena Chandra, Alexander Kornienko, Patricia Burth. Effect of polygodial and its direct derivatives on the mammalian Na+/K+-ATPase activity. European journal of pharmacology. 2018 Jul; 831(?):1-8. doi: 10.1016/j.ejphar.2018.04.031. [PMID: 29715454]
  • 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]
  • Dahai He, Carla Slebodnick, L Harinantenaina Rakotondraibe. Bioactive drimane sesquiterpenoids and aromatic glycosides from Cinnamosma fragrans. Bioorganic & medicinal chemistry letters. 2017 04; 27(8):1754-1759. doi: 10.1016/j.bmcl.2017.02.067. [PMID: 28274626]
  • D Pereira-Torres, A T Gonçalves, V Ulloa, R Martínez, H Carrasco, A F Olea, L Espinoza, C Gallardo-Escárate, A Astuya. In vitro modulation of Drimys winteri bark extract and the active compound polygodial on Salmo salar immune genes after exposure to Saprolegnia parasitica. Fish & shellfish immunology. 2016 Dec; 59(?):103-108. doi: 10.1016/j.fsi.2016.10.035. [PMID: 27777106]
  • Kaidu H Barrosa, Murilo C Mecchi, Daniela G Rando, Ari José S Ferreira, Patricia Sartorelli, Maíra M R Valle, Silvana Bordin, Luciana C Caperuto, João Henrique G Lago, Camilo Lellis-Santos. Polygodial, a sesquiterpene isolated from Drimys brasiliensis (Winteraceae), triggers glucocorticoid-like effects on pancreatic β-cells. Chemico-biological interactions. 2016 Oct; 258(?):245-56. doi: 10.1016/j.cbi.2016.09.013. [PMID: 27645309]
  • Neli Prota, Harro J Bouwmeester, Maarten A Jongsma. Comparative antifeedant activities of polygodial and pyrethrins against whiteflies (Bemisia tabaci) and aphids (Myzus persicae). Pest management science. 2014 Apr; 70(4):682-8. doi: 10.1002/ps.3610. [PMID: 23868321]
  • Patrick Louis Cahill, David Burritt, Kevin Heasman, Andrew Jeffs, Jeanne Kuhajek. Screening for antioxidant and detoxification responses in Perna canaliculus Gmelin exposed to an antifouling bioactive intended for use in aquaculture. Chemosphere. 2013 Oct; 93(6):931-8. doi: 10.1016/j.chemosphere.2013.05.058. [PMID: 23830117]
  • Ivan Montenegro, Luis Pino, Enrique Werner, Alejandro Madrid, Luis Espinoza, Luis Moreno, Joan Villena, Mauricio Cuellar. Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against Drosophila melanogaster til-til. Molecules (Basel, Switzerland). 2013 Apr; 18(4):4192-208. doi: 10.3390/molecules18044192. [PMID: 23612472]
  • Luke J Cooney, John W van Klink, Nicole M Hughes, Nigel B Perry, H Martin Schaefer, Ignatius J Menzies, Kevin S Gould. Red leaf margins indicate increased polygodial content and function as visual signals to reduce herbivory in Pseudowintera colorata. The New phytologist. 2012 Apr; 194(2):488-497. doi: 10.1111/j.1469-8137.2012.04063.x. [PMID: 22309352]
  • Daniela S Corrêa, André G Tempone, Juliana Q Reimão, Noemi N Taniwaki, Paulete Romoff, Oriana A Fávero, Patricia Sartorelli, Murilo C Mecchi, João Henrique G Lago. Anti-leishmanial and anti-trypanosomal potential of polygodial isolated from stem barks of Drimys brasiliensis Miers (Winteraceae). Parasitology research. 2011 Jul; 109(1):231-6. doi: 10.1007/s00436-010-2229-8. [PMID: 21243506]
  • Lucia Helena Martini, Fernanda Jung, Felix Antunes Soares, Liane Nanci Rotta, Deusa Aparecida Vendite, Marcos Emilio dos Santos Frizzo, Rosendo A Yunes, João Batista Calixto, Susana Wofchuk, Diogo O Souza. Naturally occurring compounds affect glutamatergic neurotransmission in rat brain. Neurochemical research. 2007 Nov; 32(11):1950-6. doi: 10.1007/s11064-007-9393-y. [PMID: 17577666]
  • Juntaro Nakajima, Pete Papaah, Masako Yoshizawa, Francesco Marotta, Teriyuki Nakajima, Shin Mihara, Emilio Minelli. Effect of a novel phyto-compound on mucosal candidiasis: further evidence from an ex vivo study. Journal of digestive diseases. 2007 Feb; 8(1):48-51. doi: 10.1111/j.1443-9573.2007.00283.x. [PMID: 17261135]
  • Keiko Kuroiwa, Makoto Shibutani, Kaoru Inoue, Kyoung-Youl Lee, Gye-Hyeong Woo, Masao Hirose. Subchronic toxicity study of water pepper extract in F344 rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Aug; 44(8):1236-44. doi: 10.1016/j.fct.2006.01.020. [PMID: 16542768]
  • Eunice André, Barbara Campi, Marcello Trevisani, Juliano Ferreira, Angela Malheiros, Rosendo A Yunes, João B Calixto, Pierangelo Geppetti. Pharmacological characterisation of the plant sesquiterpenes polygodial and drimanial as vanilloid receptor agonists. Biochemical pharmacology. 2006 Apr; 71(8):1248-54. doi: 10.1016/j.bcp.2005.12.030. [PMID: 16457780]
  • Lucia Helena Martini, Lucas Cereser, Isaac Zanonato Junior, Fluvia Melina Alves Jardim, Deusa Aparecida Vendite, Marcos Emilio dos Santos Frizzo, Rosendo A Yunes, João Batista Calixto, Susana Wofchuk, Diogo O Souza. The sesquiterpenes polygodial and drimanial in vitro affect glutamatergic transport in rat brain. Neurochemical research. 2006 Mar; 31(3):431-8. doi: 10.1007/s11064-005-9033-3. [PMID: 16733820]
  • F Marotta, R Barreto, S Kawakita, E Minelli, K Pavasuthipaisit, A Lorenzetti, M Nishiwaki, F Gelosa, E Fesce, R Okura. Preventive strategy for Candida gut translocation during ischemia-reperfusion injury supervening on protein-calorie malnutrition. Chinese journal of digestive diseases. 2006; 7(1):33-8. doi: 10.1111/j.1443-9573.2006.00241.x. [PMID: 16412035]
  • Ken-ichi Fujita, Isao Kubo. Multifunctional action of antifungal polygodial against Saccharomyces cerevisiae: involvement of pyrrole formation on cell surface in antifungal action. Bioorganic & medicinal chemistry. 2005 Dec; 13(24):6742-7. doi: 10.1016/j.bmc.2005.07.023. [PMID: 16122929]
  • Ken-Ichi Fujita, Isao Kubo. Naturally occurring antifungal agents against Zygosaccharomyces bailii and their synergism. Journal of agricultural and food chemistry. 2005 Jun; 53(13):5187-91. doi: 10.1021/jf0500987. [PMID: 15969495]
  • Eunice Andre, Juliano Ferreira, Angela Malheiros, Rosendo A Yunes, João B Calixto. Evidence for the involvement of vanilloid receptor in the antinociception produced by the dialdeydes unsaturated sesquiterpenes polygodial and drimanial in rats. Neuropharmacology. 2004 Mar; 46(4):590-7. doi: 10.1016/j.neuropharm.2003.10.008. [PMID: 14975683]
  • Ken-Ichi Fujita, Isao Kubo. Synergism of polygodial and trans-cinnamic acid on inhibition of root elongation in lettuce seedling growth bioassays. Journal of chemical ecology. 2003 Oct; 29(10):2253-62. doi: 10.1023/a:1026270329989. [PMID: 14682510]
  • Yutana Pongpiriyadacha, Hisashi Matsuda, Toshio Morikawa, Yasunobu Asao, Masayuki Yoshikawa. Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action. Biological & pharmaceutical bulletin. 2003 May; 26(5):651-7. doi: 10.1248/bpb.26.651. [PMID: 12736506]
  • Eunice André, Angela Malheiros, Valdir Cechinel-Filho, Rosendo A Yunes, João B Calixto. Role of nitric oxide and K+ channels in relaxation induced by polygodial in rabbit corpus cavernosum in vitro. Journal of cardiovascular pharmacology. 2003 Feb; 41(2):300-6. doi: 10.1097/00005344-200302000-00020. [PMID: 12548092]
  • Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Yousuke Kashima, Kyoko Nakano, Masayuki Yoshikawa. Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rats: structural requirements and mode of action. Bioorganic & medicinal chemistry letters. 2002 Feb; 12(3):477-82. doi: 10.1016/s0960-894x(01)00781-8. [PMID: 11814823]
  • F M da Cunha, T S Fröde, G L Mendes, A Malheiros, V Cechinel Filho, R A Yunes, J B Calixto. Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. Life sciences. 2001 Nov; 70(2):159-69. doi: 10.1016/s0024-3205(01)01387-x. [PMID: 11787941]
  • T M de Almeida Alves, F L Ribeiro, H Kloos, C L Zani. Polygodial, the fungitoxic component from the Brazilian medicinal plant Polygonum punctatum. Memorias do Instituto Oswaldo Cruz. 2001 Aug; 96(6):831-3. doi: 10.1590/s0074-02762001000600016. [PMID: 11562711]
  • I Kubo, K Fujita, S H Lee. Antifungal mechanism of polygodial. Journal of agricultural and food chemistry. 2001 Mar; 49(3):1607-11. doi: 10.1021/jf000136g. [PMID: 11312903]
  • T Ban, I P Singh, H Etoh. Polygodial, a potent attachment-inhibiting substance for the blue mussel, Mytilus edulis galloprovincialis from Tasmannia lanceolata. Bioscience, biotechnology, and biochemistry. 2000 Dec; 64(12):2699-701. doi: 10.1271/bbb.64.2699. [PMID: 11210140]
  • C S Lunde, I Kubo. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrobial agents and chemotherapy. 2000 Jul; 44(7):1943-53. doi: 10.1128/aac.44.7.1943-1953.2000. [PMID: 10858359]
  • M El Sayah, V Cechinel Filho, R A Yunes, T R Pinheiro, J B Calixto. Action of polygodial, a sesquiterpene isolated from Drymis winteri, in the guinea-pig ileum and trachea 'in vitro'. European journal of pharmacology. 1998 Mar; 344(2-3):215-21. doi: 10.1016/s0014-2999(97)01570-7. [PMID: 9600657]
  • G L Mendes, A R Santos, M M Campos, K S Tratsk, R A Yunes, V Cechinel Filho, J B Calixto. Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae). Life sciences. 1998; 63(5):369-81. doi: 10.1016/s0024-3205(98)00285-9. [PMID: 9714424]
  • M Taniguchi, I Kubo. Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II. Journal of natural products. 1993 Sep; 56(9):1539-46. doi: 10.1021/np50099a012. [PMID: 8254349]
  • M Himejima, I Kubo. Antimicrobial agents from Licaria puchuri-major and their synergistic effect with polygodial. Journal of natural products. 1992 May; 55(5):620-5. doi: 10.1021/np50083a010. [PMID: 1517735]
  • I Kubo, M Taniguchi. Polygodial, an antifungal potentiator. Journal of natural products. 1988 Jan; 51(1):22-9. doi: 10.1021/np50055a002. [PMID: 3286823]
  • J L Stampf, C Benezra, Y Asakawa. Stereospecificity of allergic contact dermatitis (ACD) to enantiomers. Part III. experimentally induced ACD to a natural sesquiterpene dialdehyde, polygodial in guinea pigs. Archives of dermatological research. 1982; 274(3-4):277-81. doi: 10.1007/bf00403730. [PMID: 6891888]