alpha-pyrone (BioDeep_00001871977)

   

Volatile Flavor Compounds natural product


代谢物信息卡片


2H-Pyran-2-one

化学式: C5H4O2 (96.0211284)
中文名称: 2氢-吡喃-2酮, 2H-吡喃-2-酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=O)OC=C1
InChI: InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H

描述信息

同义名列表

3 个代谢物同义名

2H-Pyran-2-one; alpha-pyrone; 2H-Pyran-2-one



数据库引用编号

5 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)

34 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

  • Svitlana Manoilenko, Martin Dippe, Tristan Fuchs, Daniela Eisenschmidt-Bönn, Jörg Ziegler, Anne-Katrin Bauer, Ludger A Wessjohann. Enzymatic one-step synthesis of natural 2-pyrones and new-to-nature derivatives from coenzyme A esters. Journal of biotechnology. 2024 Jun; 388(?):72-82. doi: 10.1016/j.jbiotec.2024.04.006. [PMID: 38616039]
  • Zhonghua Yu, Xiuxiang Lu, Jaehyuck Choi, Shulin Deng, Binghong Xiong, Wenge Zhang, Huan Wang, Sasa Wang, Haibo Tan. 2-Pyrones from endophytic fungus Diaporthe foeniculina BZM-15. Natural product research. 2022 Oct; 36(19):4853-4861. doi: 10.1080/14786419.2021.1904400. [PMID: 33771054]
  • Sandra Notonier, Allison Z Werner, Eugene Kuatsjah, Linda Dumalo, Paul E Abraham, E Anne Hatmaker, Caroline B Hoyt, Antonella Amore, Kelsey J Ramirez, Sean P Woodworth, Dawn M Klingeman, Richard J Giannone, Adam M Guss, Robert L Hettich, Lindsay D Eltis, Christopher W Johnson, Gregg T Beckham. Metabolism of syringyl lignin-derived compounds in Pseudomonas putida enables convergent production of 2-pyrone-4,6-dicarboxylic acid. Metabolic engineering. 2021 05; 65(?):111-122. doi: 10.1016/j.ymben.2021.02.005. [PMID: 33741529]
  • Filipe Silveira Duarte, Marcelo Duzzioni, Rafael Luiz Prim, Alcíbia Maia Cardozo, Claudia Regina Dos Santos, Maria Goretti da Silva, Maria Beatriz Cacese Shiozawa, Beatriz Garcia Mendes, Tiago Tizziani, Inês Maria Costa Brighente, Moacir Geraldo Pizzolatti, Thereza Christina Monteiro de Lima. Psychopharmacological effects and safety of styryl-2-pyrones and dihydrostyryl-2-pyrones-rich fraction from Polygala sabulosa: absence of withdrawal syndrome and tolerance to anxiolytic-like and anticonvulsant effects. The Journal of pharmacy and pharmacology. 2018 Sep; 70(9):1272-1286. doi: 10.1111/jphp.12960. [PMID: 29956326]
  • Jie Wang, Feng-Rong Mu, Wei-Hua Jiao, Jian Huang, Li-Li Hong, Fan Yang, Ying Xu, Shu-Ping Wang, Fan Sun, Hou-Wen Lin. Meroterpenoids with Protein Tyrosine Phosphatase 1B Inhibitory Activity from a Hyrtios sp. Marine Sponge. Journal of natural products. 2017 09; 80(9):2509-2514. doi: 10.1021/acs.jnatprod.7b00435. [PMID: 28834433]
  • Juha Kontturi, Raisa Osama, Xianbao Deng, Hany Bashandy, Victor A Albert, Teemu H Teeri. Functional characterization and expression of GASCL1 and GASCL2, two anther-specific chalcone synthase like enzymes from Gerbera hybrida. Phytochemistry. 2017 Feb; 134(?):38-45. doi: 10.1016/j.phytochem.2016.11.002. [PMID: 27884449]
  • Milla Pietiäinen, Juha Kontturi, Tanja Paasela, Xianbao Deng, Miia Ainasoja, Paulina Nyberg, Hannu Hotti, Teemu H Teeri. Two polyketide synthases are necessary for 4-hydroxy-5-methylcoumarin biosynthesis in Gerbera hybrida. The Plant journal : for cell and molecular biology. 2016 09; 87(6):548-58. doi: 10.1111/tpj.13216. [PMID: 27227340]
  • Wei Zhou, Yibin Zhuang, Yanfen Bai, Huiping Bi, Tao Liu, Yanhe Ma. Biosynthesis of phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone in Escherichia coli from glucose. Microbial cell factories. 2016 Aug; 15(1):149. doi: 10.1186/s12934-016-0549-9. [PMID: 27577056]
  • Jie-Feng Tian, Ru-Jian Yu, Xiao-Xia Li, Hao Gao, Liang-Dong Guo, Jin-Shan Tang, Xin-Sheng Yao. ¹H and ¹³C NMR spectral assignments of 2-pyrone derivatives from an endophytic fungus of sarcosomataceae. Magnetic resonance in chemistry : MRC. 2015 Oct; 53(10):866-71. doi: 10.1002/mrc.4282. [PMID: 26255790]
  • Mamta Sagar, Neetesh Pandey, Naseha Qamar, Brijendra Singh, Akanksha Shukla. Domain analysis of 3 Keto Acyl-CoA synthase for structural variations in Vitis vinifera and Oryza brachyantha using comparative modelling. Interdisciplinary sciences, computational life sciences. 2015 Mar; 7(1):7-20. doi: 10.1007/s12539-013-0017-8. [PMID: 25239516]
  • Daniele Sanna, Linda Bíró, Péter Buglyó, Giovanni Micera, Eugenio Garribba. Transport of the anti-diabetic VO2+ complexes formed by pyrone derivatives in the blood serum. Journal of inorganic biochemistry. 2012 Oct; 115(?):87-99. doi: 10.1016/j.jinorgbio.2012.04.020. [PMID: 22926028]
  • Kazuhiko Otoguro, Masato Iwatsuki, Aki Ishiyama, Miyuki Namatame, Aki Nishihara-Tsukashima, Hiroaki Kiyohara, Toshihiro Hashimoto, Yoshinori Asakawa, Satoshi Omura, Haruki Yamada. In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). Journal of natural medicines. 2012 Jul; 66(3):558-61. doi: 10.1007/s11418-011-0613-z. [PMID: 22116743]
  • Guo-Qiang Li, Yao-Lan Li, Tao Jiang, Ren-Wang Jiang, Guo-Cai Wang. 3-Benzyl-2H-chromen-2-one. Acta crystallographica. Section E, Structure reports online. 2012 May; 68(Pt 5):o1504. doi: 10.1107/s1600536812014298. [PMID: 22590375]
  • Gang Ding, Yingxiang Qi, Shuchun Liu, Liangdong Guo, Xulin Chen. Photipyrones A and B, new pyrone derivatives from the plant endophytic fungus Pestalotiopsis photiniae. The Journal of antibiotics. 2012 May; 65(5):271-3. doi: 10.1038/ja.2012.14. [PMID: 22415458]
  • Yi Wu, Xin Hu, Guang-Zhong Yang, Zhi-Nan Mei, Yu Chen. Two new flavanols from Glycosmis pentaphylla. Journal of Asian natural products research. 2012; 14(8):738-42. doi: 10.1080/10286020.2012.688745. [PMID: 22694263]
  • Hervé Colinet, David Renault, Blandine Charoy-Guével, Emmanuelle Com. Metabolic and proteomic profiling of diapause in the aphid parasitoid Praon volucre. PloS one. 2012; 7(2):e32606. doi: 10.1371/journal.pone.0032606. [PMID: 22389713]
  • Raja Noor Zaliha Raja Abdul Rahman, Iffah Izzati Zakaria, Abu Bakar Salleh, Mahiran Basri. Enzymatic properties and mutational studies of chalcone synthase from Physcomitrella patens. International journal of molecular sciences. 2012; 13(8):9673-9691. doi: 10.3390/ijms13089673. [PMID: 22949824]
  • Hariyanti Baharum, Hiroyuki Morita, Akifumi Tomitsuka, Fong-Chin Lee, Kim-Yong Ng, Raha Abdul Rahim, Ikuro Abe, Chai-Ling Ho. Molecular cloning, modeling, and site-directed mutagenesis of type III polyketide synthase from Sargassum binderi (Phaeophyta). Marine biotechnology (New York, N.Y.). 2011 Oct; 13(5):845-56. doi: 10.1007/s10126-010-9344-5. [PMID: 21181422]
  • Dong Liu, Xiao-Ming Li, Li Meng, Chun-Shun Li, Shu-Shan Gao, Zhuo Shang, Peter Proksch, Cai-Guo Huang, Bin-Gui Wang. Nigerapyrones A-H, α-pyrone derivatives from the marine mangrove-derived endophytic fungus Aspergillus niger MA-132. Journal of natural products. 2011 Aug; 74(8):1787-91. doi: 10.1021/np200381u. [PMID: 21774474]
  • Yongbiao Wei, Chengyue Zhang, Pan Zhao, Xiaoda Yang, Kui Wang. A new salicylic acid-derivatized kojic acid vanadyl complex: synthesis, characterization and anti-diabetic therapeutic potential. Journal of inorganic biochemistry. 2011 Aug; 105(8):1081-5. doi: 10.1016/j.jinorgbio.2011.05.008. [PMID: 21726771]
  • Juan Carlos Guevara-Arauza, José de Jesús Ornelas Paz, Sergio Rosales Mendoza, Ruth Elena Soria Guerra, Luz María Teresita Paz Maldonado, Diana Jaqueline Pimentel González. Biofunctional activity of tortillas and bars enhanced with nopal. Preliminary assessment of functional effect after intake on the oxidative status in healthy volunteers. Chemistry Central journal. 2011 Mar; 5(1):10. doi: 10.1186/1752-153x-5-10. [PMID: 21371324]
  • J M Valente Nabais, Jorge Ginja Teixeira, I Almeida. Development of easy made low cost bindless monolithic electrodes from biomass with controlled properties to be used as electrochemical capacitors. Bioresource technology. 2011 Feb; 102(3):2781-7. doi: 10.1016/j.biortech.2010.11.083. [PMID: 21146406]
  • Koichiro Aya, Go Suzuki, Keita Suwabe, Tokunori Hobo, Hirokazu Takahashi, Katsuhiro Shiono, Kentaro Yano, Nobuhiro Tsutsumi, Mikio Nakazono, Yoshiaki Nagamura, Makoto Matsuoka, Masao Watanabe. Comprehensive network analysis of anther-expressed genes in rice by the combination of 33 laser microdissection and 143 spatiotemporal microarrays. PloS one. 2011; 6(10):e26162. doi: 10.1371/journal.pone.0026162. [PMID: 22046259]
  • Simon Wallace, Andrew Fleming, Charles H Wellman, David J Beerling. Evolutionary development of the plant and spore wall. AoB PLANTS. 2011; 2011(?):plr027. doi: 10.1093/aobpla/plr027. [PMID: 22476497]
  • Sung Soo Kim, Etienne Grienenberger, Benjamin Lallemand, Che C Colpitts, Sun Young Kim, Clarice de Azevedo Souza, Pierrette Geoffroy, Dimitri Heintz, Daniel Krahn, Markus Kaiser, Erich Kombrink, Thierry Heitz, Dae-Yeon Suh, Michel Legrand, Carl J Douglas. LAP6/POLYKETIDE SYNTHASE A and LAP5/POLYKETIDE SYNTHASE B encode hydroxyalkyl α-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana. The Plant cell. 2010 Dec; 22(12):4045-66. doi: 10.1105/tpc.110.080028. [PMID: 21193570]
  • Etienne Grienenberger, Sung Soo Kim, Benjamin Lallemand, Pierrette Geoffroy, Dimitri Heintz, Clarice de Azevedo Souza, Thierry Heitz, Carl J Douglas, Michel Legrand. Analysis of TETRAKETIDE α-PYRONE REDUCTASE function in Arabidopsis thaliana reveals a previously unknown, but conserved, biochemical pathway in sporopollenin monomer biosynthesis. The Plant cell. 2010 Dec; 22(12):4067-83. doi: 10.1105/tpc.110.080036. [PMID: 21193572]
  • Linda Bíró, Etelka Farkas, Péter Buglyó. Complex formation between Ru(η(6)-p-cym)(H2O)3]2+ and (O,O) donor ligands with biological relevance in aqueous solution. Dalton transactions (Cambridge, England : 2003). 2010 Nov; 39(42):10272-8. doi: 10.1039/c0dt00469c. [PMID: 20922244]
  • Anna A Dobritsa, Zhentian Lei, Shuh-Ichi Nishikawa, Ewa Urbanczyk-Wochniak, David V Huhman, Daphne Preuss, Lloyd W Sumner. LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis. Plant physiology. 2010 Jul; 153(3):937-55. doi: 10.1104/pp.110.157446. [PMID: 20442277]
  • Ming-Jen Cheng, Jih-Jung Chen, Ming-Der Wu, Ping-Shin Yang, Gwo-Fang Yuan. Isolation and structure determination of one new metabolite isolated from the red fermented rice of Monascus purpureus. Natural product research. 2010 Jun; 24(10):979-88. doi: 10.1080/14786410903368290. [PMID: 20496238]
  • Yuxiang Zheng, Alan R Brash. Formation of a cyclopropyl epoxide via a leukotriene A synthase-related pathway in an anaerobic reaction of soybean lipoxygenase-1 with 15S-hydroperoxyeicosatetraenoic acid: evidence that oxygen access is a determinant of secondary reactions with fatty acid hydroperoxides. The Journal of biological chemistry. 2010 Apr; 285(18):13427-36. doi: 10.1074/jbc.m109.084632. [PMID: 20194505]
  • Shin-ichiro Kurimoto, Mamoru Okasaka, Yoshiki Kashiwada, Olimjon K Kodzhimatov, Yoshihisa Takaishi. A C14-polyacetylenic glucoside with an alpha-pyrone moiety and four C10-polyacetylenic glucosides from Mediasia macrophylla. Phytochemistry. 2010 Apr; 71(5-6):688-92. doi: 10.1016/j.phytochem.2009.12.007. [PMID: 20074759]
  • Phuong Thien Thuong, Tran Manh Hung, Tran Minh Ngoc, Do Thi Ha, Byung Sun Min, Seung Jun Kwack, Tae Suk Kang, Jae Sue Choi, KiHwan Bae. Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. Phytotherapy research : PTR. 2010 Jan; 24(1):101-6. doi: 10.1002/ptr.2890. [PMID: 19468986]
  • Jiao Zheng, Li Tang, Xun-De Xian, Si-Xiang Zhou, Hai-Ming Shi, Yong Jiang, Yue-Qing Gu, George Liu, Peng-Fei Tu. Inhibitory effect of triterpenoid saponins from the leaves of Ilex kudingcha on aggregated LDL-induced lipid deposition in macrophages. Planta medica. 2009 Oct; 75(13):1410-4. doi: 10.1055/s-0029-1185722. [PMID: 19468972]
  • R E Nuñez-Anita, O Arroyo-Helguera, M Cajero-Juárez, L López-Bojorquez, C Aceves. A complex between 6-iodolactone and the peroxisome proliferator-activated receptor type gamma may mediate the antineoplastic effect of iodine in mammary cancer. Prostaglandins & other lipid mediators. 2009 Jun; 89(1-2):34-42. doi: 10.1016/j.prostaglandins.2009.04.001. [PMID: 19443248]
  • Hiroyuki Yamazaki, Satoshi Omura, Hiroshi Tomoda. Pentacecilides, new inhibitors of lipid droplet formation in mouse macrophages produced by Penicillium cecidicola FKI-3765-1: II. Structure elucidation. The Journal of antibiotics. 2009 Apr; 62(4):207-11. doi: 10.1038/ja.2009.19. [PMID: 19300471]
  • Samy K El-Desouky, Mona E S Kassem, Zarag I A Al-Fifi, Amira M Gamal El-Deen. A new pyranone derivative from the leaves of Livistona australis. Natural product communications. 2009 Apr; 4(4):499-500. doi: ". [PMID: 19475992]
  • Tamara L Meragelman, Dominic A Scudiero, R Eric Davis, Louis M Staudt, Thomas G McCloud, John H Cardellina, Robert H Shoemaker. Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa. Journal of natural products. 2009 Mar; 72(3):336-9. doi: 10.1021/np800350x. [PMID: 19093800]
  • M David Marks, Li Tian, Jonathan P Wenger, Stephanie N Omburo, Wilfredo Soto-Fuentes, Ji He, David R Gang, George D Weiblen, Richard A Dixon. Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa. Journal of experimental botany. 2009; 60(13):3715-26. doi: 10.1093/jxb/erp210. [PMID: 19581347]
  • Su-Yen Chang, Ming-Jen Cheng, Chien-Fang Peng, Hsun-Shuo Chang, Ih-Sheng Chen. Antimycobacterial butanolides from the root of Lindera akoensis. Chemistry & biodiversity. 2008 Dec; 5(12):2690-8. doi: 10.1002/cbdv.200890223. [PMID: 19089827]
  • Sengottayan Senthil-Nathan, Man-Young Choi, Chae-Hoon Paik, Kandaswamy Kalaivani. The toxicity and physiological effect of goniothalamin, a styryl-pyrone, on the generalist herbivore, Spodoptera exigua Hübner. Chemosphere. 2008 Jul; 72(9):1393-400. doi: 10.1016/j.chemosphere.2008.03.037. [PMID: 18499224]
  • Amal H Aly, Ruangelie Edrada-Ebel, Victor Wray, Werner E G Müller, Svitlana Kozytska, Ute Hentschel, Peter Proksch, Rainer Ebel. Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides. Phytochemistry. 2008 May; 69(8):1716-25. doi: 10.1016/j.phytochem.2008.02.013. [PMID: 18400237]
  • Xiu-Sheng Miao, Pengfei Song, Ronald E Savage, Caiyun Zhong, Rui-Yang Yang, Darin Kizer, Hui Wu, Erika Volckova, Mark A Ashwell, Jeffrey G Supko, Xiaoying He, Thomas C K Chan. Identification of the in vitro metabolites of 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione (ARQ 501; beta-lapachone) in whole blood. Drug metabolism and disposition: the biological fate of chemicals. 2008 Apr; 36(4):641-8. doi: 10.1124/dmd.107.018572. [PMID: 18180274]
  • María del Carmen Hernández-Romero, Sandro Argüelles, Ruth F Villarán, Rocío M de Pablos, María José Delgado-Cortés, Marti Santiago, Antonio J Herrera, Josefina Cano, Alberto Machado. Simvastatin prevents the inflammatory process and the dopaminergic degeneration induced by the intranigral injection of lipopolysaccharide. Journal of neurochemistry. 2008 Apr; 105(2):445-59. doi: 10.1111/j.1471-4159.2007.05148.x. [PMID: 18047562]
  • Roosa A E Laitinen, Miia Ainasoja, Suvi K Broholm, Teemu H Teeri, Paula Elomaa. Identification of target genes for a MYB-type anthocyanin regulator in Gerbera hybrida. Journal of experimental botany. 2008; 59(13):3691-703. doi: 10.1093/jxb/ern216. [PMID: 18725377]
  • Sheng-Xiong Huang, Jing Yang, Hao Huang, Li-Mei Li, Wei-Lie Xiao, Rong-Tao Li, Han-Dong Sun. Structural characterization of schintrilactone, a new class of nortriterpenoids from Schisandra chinensis. Organic letters. 2007 Oct; 9(21):4175-8. doi: 10.1021/ol701679n. [PMID: 17880096]
  • Giovanni Appendino, Michela Ottino, Nieves Marquez, Federica Bianchi, Anna Giana, Mauro Ballero, Olov Sterner, Bernd L Fiebich, Eduardo Munoz. Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum. Journal of natural products. 2007 Apr; 70(4):608-12. doi: 10.1021/np060581r. [PMID: 17315926]
  • Antonella Rosa, Monica Deiana, Angela Atzeri, Giulia Corona, Alessandra Incani, M Paola Melis, Giovanni Appendino, M Assunta Dessì. Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp.microphyllum. Chemico-biological interactions. 2007 Jan; 165(2):117-26. doi: 10.1016/j.cbi.2006.11.006. [PMID: 17194458]
  • Yuichiro Otsuka, Masaya Nakamura, Kiyotaka Shigehara, Kosuke Sugimura, Eiji Masai, Seiji Ohara, Yoshihiro Katayama. Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function. Applied microbiology and biotechnology. 2006 Aug; 71(5):608-14. doi: 10.1007/s00253-005-0203-7. [PMID: 16322989]
  • Zhimou Wen, May R Berenbaum, Mary A Schuler. Inhibition of CYP6B1-mediated detoxification of xanthotoxin by plant allelochemicals in the black swallowtail (Papilio polyxenes). Journal of chemical ecology. 2006 Mar; 32(3):507-22. doi: 10.1007/s10886-005-9014-7. [PMID: 16570215]
  • B P Nutley, N F Smith, A Hayes, L R Kelland, L Brunton, B T Golding, G C M Smith, N M B Martin, P Workman, F I Raynaud. Preclinical pharmacokinetics and metabolism of a novel prototype DNA-PK inhibitor NU7026. British journal of cancer. 2005 Oct; 93(9):1011-8. doi: 10.1038/sj.bjc.6602823. [PMID: 16249792]
  • Yuhua Lu, Niloufer G Irani, Erich Grotewold. Covalent attachment of the plant natural product naringenin to small glass and ceramic beads. BMC chemical biology. 2005 Oct; 5(?):3. doi: 10.1186/1472-6769-5-3. [PMID: 16216122]
  • Xiao Yi Li, Leif A Eriksson. Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. Photochemistry and photobiology. 2005 Sep; 81(5):1153-60. doi: 10.1562/2005-03-21-ra-467. [PMID: 15882092]
  • Raphaël Grougnet, Prokopios Magiatis, Nikolas Fokialakis, Sofia Mitaku, Alexios-Leandros Skaltsounis, François Tillequin, Thierry Sévenet, Marc Litaudon. Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis. Journal of natural products. 2005 Jul; 68(7):1083-6. doi: 10.1021/np050013w. [PMID: 16038554]
  • Jeroen S Dickschat, Irene Wagner-Döbler, Stefan Schulz. The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria. Journal of chemical ecology. 2005 Apr; 31(4):925-47. doi: 10.1007/s10886-005-3553-9. [PMID: 16124260]
  • L Santana, E Uriarte, F Roleira, N Milhazes, F Borges. Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity. Current medicinal chemistry. 2004 Dec; 11(24):3239-61. doi: 10.2174/0929867043363721. [PMID: 15579011]
  • Smriti Khera, Michael D Carducci, Jian-Qiao Gu, Barbara N Timmermann. (4R,4aR,6S,7S,7aS)-6-Hydroxy-7-hydroxymethyl-4-methylperhydrocyclopenta[c]pyran-1-one chloroform solvate from Valeriana laxiflora. Acta crystallographica. Section C, Crystal structure communications. 2004 Nov; 60(Pt 11):o773-5. doi: 10.1107/s0108270104021511. [PMID: 15528817]
  • Claudio Altomare, Raffaele Pengue, Mara Favilla, Antonio Evidente, Angelo Visconti. Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum. Journal of agricultural and food chemistry. 2004 May; 52(10):2997-3001. doi: 10.1021/jf035233z. [PMID: 15137845]
  • Vincent Dumontet, Nguyen Van Hung, Marie-Thérèse Adeline, Claude Riche, Angèle Chiaroni, Thierry Sévenet, Françoise Guéritte. Cytotoxic flavonoids and alpha-pyrones from Cryptocarya obovata. Journal of natural products. 2004 May; 67(5):858-62. doi: 10.1021/np030510h. [PMID: 15165150]
  • John E Heidrich, Linda M Contos, Lucy A Hunsaker, Lorraine M Deck, David L Vander Jagt. Inhibition of pancreatic cholesterol esterase reduces cholesterol absorption in the hamster. BMC pharmacology. 2004 Apr; 4(?):5. doi: 10.1186/1471-2210-4-5. [PMID: 15096274]
  • Xiao-mei Li, Mao Lin, Ying-hong Wang, Xin Liu. Four new stilbenoids from the lianas of Gnetum montanum f. megalocarpum. Planta medica. 2004 Feb; 70(2):160-5. doi: 10.1055/s-2004-815494. [PMID: 14994195]
  • Marian L Neuhouser. Dietary flavonoids and cancer risk: evidence from human population studies. Nutrition and cancer. 2004; 50(1):1-7. doi: 10.1207/s15327914nc5001_1. [PMID: 15572291]
  • Antonio Evidente, Annalisa Cabras, Lucia Maddau, Salvatorica Serra, Anna Andolfi, Andrea Motta. Viridepyronone, a new antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride. Journal of agricultural and food chemistry. 2003 Nov; 51(24):6957-60. doi: 10.1021/jf034708j. [PMID: 14611154]
  • Ying-kun Qiu, De-qiang Dou, Yu-ping Pei, Masayuki Yoshikawa, Hisashi Matsuda, Ying-jie Chen. [The isolation and identification of a new alpha-pyrone from Opuntia dillenii]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jul; 38(7):523-5. doi: ". [PMID: 14515798]
  • Yan Hua, Li He, Han-qing Wang. [Studies on flavonoids of Anaphalis sinica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Jun; 28(6):530-3. doi: ". [PMID: 15015333]
  • Johannes Schulze, Walter Raasch, Claus-Peter Siegers. Toxicity of kava pyrones, drug safety and precautions--a case study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2003; 10 Suppl 4(?):68-73. doi: 10.1078/1433-187x-00300. [PMID: 12807347]
  • Supachai Samappito, Jonathan Page, Jürgen Schmidt, Wanchai De-Eknamkul, Toni M Kutchan. Molecular characterization of root-specific chalcone synthases from Cassia alata. Planta. 2002 Nov; 216(1):64-71. doi: 10.1007/s00425-002-0872-8. [PMID: 12430015]
  • Yoshiaki Kamano, Toshihiko Nogawa, Ayano Yamashita, Masahiko Hayashi, Masuo Inoue, Pavel Drasar, George R Pettit. Isolation and structure of a 20,21-epoxybufenolide series from 'Ch'an Su'. Journal of natural products. 2002 Jul; 65(7):1001-5. doi: 10.1021/np0200360. [PMID: 12141860]
  • Thomayant Prueksaritanont, Raju Subramanian, Xiaojun Fang, Bennett Ma, Yue Qiu, Jiunn H Lin, Paul G Pearson, Thomas A Baillie. Glucuronidation of statins in animals and humans: a novel mechanism of statin lactonization. Drug metabolism and disposition: the biological fate of chemicals. 2002 May; 30(5):505-12. doi: 10.1124/dmd.30.5.505. [PMID: 11950779]
  • Susan W Hovorka, Michael J Hageman, Christian Schöneich. Oxidative degradation of a sulfonamide-containing 5,6-dihydro-4-hydroxy-2-pyrone in aqueous/organic cosolvent mixtures. Pharmaceutical research. 2002 Apr; 19(4):538-45. doi: 10.1023/a:1015116317269. [PMID: 12033392]
  • V Weber, P Coudert, E Duroux, F Leal, J Couquelet, M Madesclaire. Synthesis and in vitro studies of pyrone derivatives as scavengers of active oxygen species. Arzneimittel-Forschung. 2001 Nov; 51(11):877-84. doi: 10.1055/s-0031-1300131. [PMID: 11765588]
  • M Rey, J Delgado-Jarana, T Benítez. Improved antifungal activity of a mutant of Trichoderma harzianum CECT 2413 which produces more extracellular proteins. Applied microbiology and biotechnology. 2001 May; 55(5):604-8. doi: 10.1007/s002530000551. [PMID: 11414328]
  • . . . . doi: . [PMID: 12620343]
  • . . . . doi: . [PMID: 22923580]