Furanone A (BioDeep_00000011779)
Secondary id: BioDeep_00001868621
human metabolite
代谢物信息卡片
4-Hydroxy-3-butenoic acid gamma-lactone
化学式: C4H4O2 (84.0211284)
中文名称: 2（3H）-呋喃酮
谱图信息:
最多检出来源 Homo sapiens(not specific) 28.74%
分子结构信息
SMILES: C1C=COC1=O
InChI: InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1,3H,2H2
描述信息
Furanone a, also known as alpha-Crotonolactone or 2-Furanone, is classified as a member of the butenolides. Butenolides are dihydrofurans with a carbonyl group at the C2 carbon atom. Furanone a is considered to be a soluble (in water) and an extremely weak acidic compound. Furanone a can be found in feces.
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
D019440 - Anti-Obesity Agents > D001067 - Appetite Depressants
同义名列表
26 个代谢物同义名
4-Hydroxy-3-butenoic acid gamma-lactone; 4-Hydroxy-3-butenoate gamma-lactone; 4-Hydroxy-3-butenoic acid γ-lactone; 4-Hydroxy-3-butenoic acid g-lactone; 4-Hydroxy-3-butenoate g-lactone; 4-Hydroxy-3-butenoate γ-lactone; beta,gamma-Crotonolactone; 2,3-dihydrofuran-2-one; 2-oxo-2,3-Dihydrofuran; alpha-Crotonolactone; Β,γ-crotonolactone; b,g-Crotonolactone; Α-crotonolactone; a-Crotonolactone; 2-Buten-4-olide; alpha-Furanone; Crotonolactone; 2(3H)-Furanone; Α-furanone; Furanone A; 2-Furanone; a-Furanone; Butenolide; 2-b4O; 2(3H)-Furanone; 2(3H)-Furanone
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:38120
- KEGG: C17602
- PubChem: 140765
- HMDB: HMDB0094691
- Metlin: METLIN71807
- CAS: 20825-71-2
- PMhub: MS000025931
- PubChem: 96023947
- NIKKAJI: J82.327I
- KNApSAcK: 38120
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)
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
- Qinghe Zhang, Juan Tang, Bingli Gao, Cheng Qu, Jinda Wang, Chen Luo, Ran Wang. Overexpression of CYP6CX4 contributing to field-evolved resistance to flupyradifurone, one novel butenolide insecticide, in Bemisia tabaci from China.
International journal of biological macromolecules.
2024 Apr; 265(Pt 2):131056. doi:
10.1016/j.ijbiomac.2024.131056. [PMID: 38522686] - Renxuan Zou, Xiang Li, Xi Jiang, Dongmei Shi, Qing Han, Hongxia Duan, Qing Yang. Novel Butenolide Derivatives as Dual-Chitinase Inhibitors to Arrest the Growth and Development of the Asian Corn Borer.
Journal of agricultural and food chemistry.
2024 Mar; 72(9):5036-5046. doi:
10.1021/acs.jafc.3c06714. [PMID: 38377548] - Yufeng Jiang, Jiule Wang, Hua Zhang, Xuelu Tian, Zhiqiang Liang, Xinli Xu, Jie Bao, Biao Chen. Biological Activity and Sterilization Mechanism of Marine Fungi-derived Aromatic Butenolide Asperbutenolide A Against Staphylococcus aureus.
Chemistry & biodiversity.
2024 Feb; 21(2):e202301826. doi:
10.1002/cbdv.202301826. [PMID: 38155523] - Kim T Melville, Muhammad Kamran, Jiaren Yao, Marianne Costa, Madeleine Holland, Nicolas L Taylor, Georg Fritz, Gavin R Flematti, Mark T Waters. Perception of butenolides by Bacillus subtilis via the α/β hydrolase RsbQ.
Current biology : CB.
2023 Dec; ?(?):. doi:
10.1016/j.cub.2023.12.035. [PMID: 38183985] - Wei Wang, Kang-Wen Xu, Mei Wang, Peng Wu, Zi-Ru Zhang, Xi Gao, Yi-Qiang Li, Guo-Xing Wu, Cheng-Sheng Zhang, Dong-Lin Zhao. Phytotoxic and Antimicrobial Terrein Derivatives and Butenolides Isolated from the Endophytic Fungus Aspergillus terreus HT5.
Journal of agricultural and food chemistry.
2023 Dec; 71(51):20713-20723. doi:
10.1021/acs.jafc.3c05955. [PMID: 38095326] - Muhammad Kamran, Kim T Melville, Mark T Waters. Karrikin signalling: impacts on plant development and abiotic stress tolerance.
Journal of experimental botany.
2023 Nov; ?(?):. doi:
10.1093/jxb/erad476. [PMID: 38001035] - Seham S El-Hawary, Abeer S Moawad, Hebatallah S Bahr, Eman Z Attia, Mo Men H El-Katatny, Muhamad Mustafa, Ahmed A Al-Karmalawy, Mostafa E Rateb, Jian-Ye Zhang, Usama Ramadan Abdelmohsen, Rabab Mohammed. Promising Cytotoxic butenolides from the Soybean endophytic fungus Aspergillus terreus: a combined molecular docking and in-vitro studies.
Journal of applied microbiology.
2023 Jul; ?(?):. doi:
10.1093/jambio/lxad129. [PMID: 37401132] - Yihao Li, Tingting Zhang, Haoyun Ma, Leichuan Xu, Qian Zhang, Lei He, Jiazhen Jiang, Zhenhua Zhang, Zhangwu Zhao, Mingan Wang. Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide.
Journal of agricultural and food chemistry.
2023 Apr; 71(16):6249-6267. doi:
10.1021/acs.jafc.2c09144. [PMID: 37058604] - Jiming Chen, Diwakar Shukla. Effect of Histidine Covalent Modification on Strigolactone Receptor Activation and Selectivity.
Biophysical journal.
2023 Feb; ?(?):. doi:
10.1016/j.bpj.2023.02.012. [PMID: 36798027] - Yun-Fei Ai, Shu-Hui Dong, Bin Lin, Xiao-Xiao Huang, Shao-Jiang Song. Acylated sucroses and butenolide analog from the leaves of Tripterygium wilfordii Hook. f. and their potential anti-tyrosinase effects.
Fitoterapia.
2022 Sep; 161(?):105250. doi:
10.1016/j.fitote.2022.105250. [PMID: 35798062] - Joe Bracegirdle, Sarah J Kennedy, Chuan Shan, Lukasz Wojtas, Lindsey N Shaw, Charles D Amsler, James B McClintock, Bill J Baker. Tongalides, Halogenated Butenolides from an Antarctic Delisea sp. Rhodophyte.
Journal of natural products.
2022 07; 85(7):1886-1891. doi:
10.1021/acs.jnatprod.2c00344. [PMID: 35771948] - Le-Yao Dai, Qi-Meng Yin, Jia-Kai Qiu, Zhen-Yang Zhang, Gang Li, Meng-Ni Huang, Liang Liu. Goodyschle A, a new butenolide with significant BchE inhibitory activity from Goodyera schlechtendaliana.
Natural product research.
2021 Dec; 35(23):4916-4921. doi:
10.1080/14786419.2020.1744142. [PMID: 32208851] - Honglan Mou, Jing Shi, Jixiang Chen, Deyu Hu. Synthesis, antibacterial activity and mechanism of new butenolides derivatives containing an amide moiety.
Pesticide biochemistry and physiology.
2021 Oct; 178(?):104913. doi:
10.1016/j.pestbp.2021.104913. [PMID: 34446189] - Ibrahim Seyda Uras, Sherif S Ebada, Michal Korinek, Amgad Albohy, Basma S Abdulrazik, Yi-Hsuan Wang, Bing-Hung Chen, Jim-Tong Horng, Wenhan Lin, Tsong-Long Hwang, Belma Konuklugil. Anti-Inflammatory, Antiallergic, and COVID-19 Main Protease (Mpro) Inhibitory Activities of Butenolides from a Marine-Derived Fungus Aspergillus terreus.
Molecules (Basel, Switzerland).
2021 Jun; 26(11):. doi:
10.3390/molecules26113354. [PMID: 34199488] - Jie Zhou, Si-Yu Du, Zhong-Ying Fang, Zhi Zeng. New butenolides with anti-inflammatory activity from Balanophora fungosa.
Natural product research.
2021 Jun; 35(11):1825-1829. doi:
10.1080/14786419.2019.1645663. [PMID: 31359786] - Jiaren Yao, Adrian Scaffidi, Yongjie Meng, Kim T Melville, Aino Komatsu, Aashima Khosla, David C Nelson, Junko Kyozuka, Gavin R Flematti, Mark T Waters. Desmethyl butenolides are optimal ligands for karrikin receptor proteins.
The New phytologist.
2021 05; 230(3):1003-1016. doi:
10.1111/nph.17224. [PMID: 33474738] - Jie Bao, Xiu-Xiu Li, Kongkai Zhu, Fei He, Yin-Yin Wang, Jin-Hai Yu, Xiaoyong Zhang, Hua Zhang. Bioactive aromatic butenolides from a mangrove sediment originated fungal species, Aspergillus terreus SCAU011.
Fitoterapia.
2021 Apr; 150(?):104856. doi:
10.1016/j.fitote.2021.104856. [PMID: 33582267] - Zhenya Wang, Jieyu Fang, Jiao Luo, Duoduo Hou, Yayun Tan, Zichen Gu, Yongzhuang Ge, Lu Mao, Luyang Liu, Hongmin Liu, Zhanyong Wei, Haiwei Xu. Antiviral Activity of 3D, a Butene Lactone Derivative Against Influenza A Virus In Vitro and In Vivo.
Viruses.
2021 02; 13(2):. doi:
10.3390/v13020278. [PMID: 33670217] - Martin Klapper, Kevin Schlabach, André Paschold, Shuaibing Zhang, Somak Chowdhury, Klaus-Dieter Menzel, Miriam A Rosenbaum, Pierre Stallforth. Biosynthesis of Pseudomonas-Derived Butenolides.
Angewandte Chemie (International ed. in English).
2020 03; 59(14):5607-5610. doi:
10.1002/anie.201914154. [PMID: 31880848] - Tao Yang, Yuke Lian, Chongying Wang. Comparing and Contrasting the Multiple Roles of Butenolide Plant Growth Regulators: Strigolactones and Karrikins in Plant Development and Adaptation to Abiotic Stresses.
International journal of molecular sciences.
2019 Dec; 20(24):. doi:
10.3390/ijms20246270. [PMID: 31842355] - Ping-Chen Tu, Han-Chun Tseng, Yu-Chia Liang, Guan-Jhong Huang, Te-Ling Lu, Tzong-Fu Kuo, Yueh-Hsiung Kuo. Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives.
Molecules (Basel, Switzerland).
2019 Sep; 24(18):. doi:
10.3390/molecules24183336. [PMID: 31540241] - Ji-Wen Sheng, Dong-Mei Liu, Liang Jing, Gui-Xue Xia, Wei-Fen Zhang, Jing-Ru Jiang, Jin-Bao Tang. Striatisporolide A, a butenolide metabolite from Athyrium multidentatum (Doll.) Ching, as a potential antibacterial agent.
Molecular medicine reports.
2019 Jul; 20(1):198-204. doi:
10.3892/mmr.2019.10244. [PMID: 31115578] - Devashan Naidoo, Martin Pošta, Ayan Roy, Manoj Kulkarni, Johannes Van Staden. Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one.
Phytochemistry.
2019 Jul; 163(?):187-194. doi:
10.1016/j.phytochem.2019.03.014. [PMID: 31014820] - Stéphanie M Swarbreck, Yannick Guerringue, Elsa Matthus, Fiona J C Jamieson, Julia M Davies. Impairment in karrikin but not strigolactone sensing enhances root skewing in Arabidopsis thaliana.
The Plant journal : for cell and molecular biology.
2019 05; 98(4):607-621. doi:
10.1111/tpj.14233. [PMID: 30659713] - Ping-Zhuo Liang, Kang-Sheng Ma, Xue-Wei Chen, Chun-Yan Tang, Jin Xia, Hsin Chi, Xi-Wu Gao. Toxicity and Sublethal Effects of Flupyradifurone, a Novel Butenolide Insecticide, on the Development and Fecundity of Aphis gossypii (Hemiptera: Aphididae).
Journal of economic entomology.
2019 03; 112(2):852-858. doi:
10.1093/jee/toy381. [PMID: 30590572] - Geanne A Alves Conserva, Thais A da Costa-Silva, Maiara Amaral, Guilherme M Antar, Bruno J Neves, Carolina H Andrade, Andre G Tempone, João Henrique G Lago. Butenolides from Nectandra oppositifolia (Lauraceae) displayed anti-Trypanosoma cruzi activity via deregulation of mitochondria.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Feb; 54(?):302-307. doi:
10.1016/j.phymed.2018.09.236. [PMID: 30668381] - Guangfeng Liao, Ping Wu, Jinghua Xue, Lan Liu, Hanxiang Li, Xiaoyi Wei. Asperimides A-D, anti-inflammatory aromatic butenolides from a tropical endophytic fungus Aspergillus terreus.
Fitoterapia.
2018 Nov; 131(?):50-54. doi:
10.1016/j.fitote.2018.10.011. [PMID: 30308231] - Changxing Qi, Weixi Gao, Jianping Wang, Mengting Liu, Jinwen Zhang, Chunmei Chen, Zhengxi Hu, Yongbo Xue, Dongyan Li, Qing Zhang, Yongji Lai, Qun Zhou, Hucheng Zhu, Yonghui Zhang. Terrusnolides A-D, new butenolides with anti-inflammatory activities from an endophytic Aspergillus from Tripterygium wilfordii.
Fitoterapia.
2018 Oct; 130(?):134-139. doi:
10.1016/j.fitote.2018.08.021. [PMID: 30165179] - Agnieszka Płażek, Franciszek Dubert, Przemysław Kopeć, Michał Dziurka, Agnieszka Kalandyk, Jakub Pastuszak, Piotr Waligórski, Bogdan Wolko. Long-Term Effects of Cold on Growth, Development and Yield of Narrow-Leaf Lupine May Be Alleviated by Seed Hydropriming or Butenolide.
International journal of molecular sciences.
2018 Aug; 19(8):. doi:
10.3390/ijms19082416. [PMID: 30115849] - Misa Yamauchi, Kotomi Ueno, Toshio Furumoto, Takatoshi Wakabayashi, Masaharu Mizutani, Hirosato Takikawa, Yukihiro Sugimoto. Stereospecific reduction of the butenolide in strigolactones in plants.
Bioorganic & medicinal chemistry.
2018 08; 26(14):4225-4233. doi:
10.1016/j.bmc.2018.07.016. [PMID: 30007566] - Genzoh Tanabe, Yoshiaki Manse, Teppei Ogawa, Naoki Sonoda, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Saowanee Chaipech, Yutana Pongpiriyadacha, Osamu Muraoka, Toshio Morikawa. Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum.
The Journal of organic chemistry.
2018 08; 83(15):8250-8264. doi:
10.1021/acs.joc.8b00986. [PMID: 29972303] - Fangfang Li, Daiwei Chen, Shengsheng Lu, Guang Yang, Xiaoling Zhang, Zhao Chen, Sheng Fan, Shaohua Wu, Jian He. Anti-Influenza A Viral Butenolide from Streptomyces sp. Smu03 Inhabiting the Intestine of Elephas maximus.
Viruses.
2018 07; 10(7):. doi:
10.3390/v10070356. [PMID: 29976861] - Xu Pang, Jian-Yuan Zhao, Xiao-Mei Fang, Tao Zhang, De-Wu Zhang, Hong-Yu Liu, Jing Su, Shan Cen, Li-Yan Yu. Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities.
Journal of natural products.
2017 10; 80(10):2595-2601. doi:
10.1021/acs.jnatprod.6b00878. [PMID: 29016131] - S J Castle, J P Palumbo, P Merten. Field evaluation of Cucurbit yellow stunting disorder virus transmission by Bemisia tabaci.
Virus research.
2017 09; 241(?):220-227. doi:
10.1016/j.virusres.2017.03.017. [PMID: 28342998] - Ewa Krawczyk, Marek Koprowski, Danuta Cembrowska-Lech, Agata Wójcik, Jan Kępczyński. Synthesis of tricyclic butenolides and comparison their effects with known smoke-butenolide, KAR1.
Journal of plant physiology.
2017 Aug; 215(?):91-99. doi:
10.1016/j.jplph.2017.04.021. [PMID: 28618259] - Patima Phainuphong, Vatcharin Rukachaisirikul, Kwanruthai Tadpetch, Yaowapa Sukpondma, Saowanit Saithong, Souwalak Phongpaichit, Sita Preedanon, Jariya Sakayaroj. γ-Butenolide and furanone derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178.
Phytochemistry.
2017 May; 137(?):165-173. doi:
10.1016/j.phytochem.2017.02.008. [PMID: 28228227] - Alexandre de Saint Germain, Guillaume Clavé, Marie-Ange Badet-Denisot, Jean-Paul Pillot, David Cornu, Jean-Pierre Le Caer, Marco Burger, Frank Pelissier, Pascal Retailleau, Colin Turnbull, Sandrine Bonhomme, Joanne Chory, Catherine Rameau, François-Didier Boyer. An histidine covalent receptor and butenolide complex mediates strigolactone perception.
Nature chemical biology.
2016 10; 12(10):787-794. doi:
10.1038/nchembio.2147. [PMID: 27479744] - Feng Guo, Zhanlin Li, Xiangwei Xu, Kaibo Wang, Meili Shao, Feng Zhao, Haifeng Wang, Huiming Hua, Yuehu Pei, Jiao Bai. Butenolide derivatives from the plant endophytic fungus Aspergillus terreus.
Fitoterapia.
2016 Sep; 113(?):44-50. doi:
10.1016/j.fitote.2016.06.014. [PMID: 27370101] - Yakub Ali, Mohammad Sarwar Alam, Hinna Hamid, Asif Husain, Syed Shafi, Abhijeet Dhulap, Firasat Hussain, Sameena Bano, Chetna Kharbanda, Syed Nazreen, Saqlain Haider. Design and Synthesis of Butenolide-based Novel Benzyl Pyrrolones: Their TNF-α based Molecular Docking with In vivo and In vitro Anti-inflammatory Activity.
Chemical biology & drug design.
2015 Oct; 86(4):619-25. doi:
10.1111/cbdd.12522. [PMID: 25626351] - Christopher C Presley, L Harinantenaina Rakotondraibe, Peggy J Brodie, Martin W Callmander, Richard Randrianaivo, Vincent E Rasamison, Etienne Rakotobe, David G I Kingston. A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest.
Natural product communications.
2015 Sep; 10(9):1505-7. doi:
". [PMID: 26435765] - A Kumari, H B Papenfus, M G Kulkarni, M Pošta, J Van Staden. Effect of smoke derivatives on in vitro pollen germination and pollen tube elongation of species from different plant families.
Plant biology (Stuttgart, Germany).
2015 Jul; 17(4):825-30. doi:
10.1111/plb.12300. [PMID: 25545791] - Madhukar S Said, Ashish A Chinchansure, Laxman Nawale, Ankita Durge, Ashish Wadhwani, Smita S Kulkarni, Dhiman Sarkar, Swati P Joshi. A new butenolide cinnamate and other biological active chemical constituents from Polygonum glabrum.
Natural product research.
2015; 29(22):2080-6. doi:
10.1080/14786419.2015.1004674. [PMID: 25643642] - Bin Yang, Xiaoyi Wei, Jingxia Huang, Xiuping Lin, Juan Liu, Shengrong Liao, Junfeng Wang, Xuefeng Zhou, Lishu Wang, Yonghong Liu. Sinulolides A-H, new cyclopentenone and butenolide derivatives from soft coral Sinularia sp.
Marine drugs.
2014 Oct; 12(10):5316-27. doi:
10.3390/md12105316. [PMID: 25342460] - Juan Liu, Cheng Peng, Cheng-Jun He, Jian-Lin Liu, Ya-Cong He, Li Guo, Qin-Mei Zhou, Huai Yang, Liang Xiong. New amino butenolides from the bulbs of Fritillaria unibracteata.
Fitoterapia.
2014 Oct; 98(?):53-8. doi:
10.1016/j.fitote.2014.07.009. [PMID: 25064215] - Lianguo Chen, Rui Ye, Ying Xu, Zhaoming Gao, Doris W T Au, Pei-Yuan Qian. Comparative safety of the antifouling compound butenolide and 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) to the marine medaka (Oryzias melastigma).
Aquatic toxicology (Amsterdam, Netherlands).
2014 Apr; 149(?):116-25. doi:
10.1016/j.aquatox.2014.01.023. [PMID: 24583292] - Li-Hua Zhao, X Edward Zhou, Zhong-Shan Wu, Wei Yi, Yong Xu, Suling Li, Ting-Hai Xu, Yue Liu, Run-Ze Chen, Amanda Kovach, Yangyong Kang, Li Hou, Yuanzheng He, Cen Xie, Wanling Song, Dafang Zhong, Yechun Xu, Yonghong Wang, Jiayang Li, Chenghai Zhang, Karsten Melcher, H Eric Xu. Crystal structures of two phytohormone signal-transducing α/β hydrolases: karrikin-signaling KAI2 and strigolactone-signaling DWARF14.
Cell research.
2013 Mar; 23(3):436-9. doi:
10.1038/cr.2013.19. [PMID: 23381136] - Nisha Agrawal, Deepika Pareek, Sonal Dobhal, Mahesh C Sharma, Yogesh C Joshi, Mahabeer P Dobhal. Butanolides from methanolic extract of Litsea glutinosa.
Chemistry & biodiversity.
2013 Mar; 10(3):394-400. doi:
10.1002/cbdv.201100300. [PMID: 23495156] - Vilmos Soós, Endre Sebestyén, Martin Posta, Ladislav Kohout, Marnie E Light, Johannes Van Staden, Ervin Balázs. Molecular aspects of the antagonistic interaction of smoke-derived butenolides on the germination process of Grand Rapids lettuce (Lactuca sativa) achenes.
The New phytologist.
2012 Dec; 196(4):1060-1073. doi:
10.1111/j.1469-8137.2012.04358.x. [PMID: 23046112] - Mark T Waters, Adrian Scaffidi, Gavin R Flematti, Steven M Smith. Karrikins force a rethink of strigolactone mode of action.
Plant signaling & behavior.
2012 Aug; 7(8):969-72. doi:
10.4161/psb.20977. [PMID: 22827937] - Mark T Waters, David C Nelson, Adrian Scaffidi, Gavin R Flematti, Yueming K Sun, Kingsley W Dixon, Steven M Smith. Specialisation within the DWARF14 protein family confers distinct responses to karrikins and strigolactones in Arabidopsis.
Development (Cambridge, England).
2012 Apr; 139(7):1285-95. doi:
10.1242/dev.074567. [PMID: 22357928] - Xue-Lian Chen, Hai-Li Liu, Jia Li, Guo-Rong Xin, Yue-Wei Guo. Paracaseolide A, first α-alkylbutenolide dimer with an unusual tetraquinane oxa-cage bislactone skeleton from Chinese mangrove Sonneratia paracaseolaris.
Organic letters.
2011 Oct; 13(19):5032-5. doi:
10.1021/ol201809q. [PMID: 21875121] - Miao-Miao Jiang, Yi-Fan Feng, Hao Gao, Xue Zhang, Jin-Shan Tang, Xin-Sheng Yao. Three new bis-styryllactones from Goniothalamus cheliensis.
Fitoterapia.
2011 Jun; 82(4):524-7. doi:
10.1016/j.fitote.2010.11.014. [PMID: 21075179] - Alberto de Oliveira, Claudinei A Silva, Adalberto M Silva, Marina F M Tavares, Massuo J Kato. Development and validation of a micellar electrokinetic chromatography method for quantitative determination of butenolides in Piper malacophyllum (C. Presl) C. DC.
Phytochemical analysis : PCA.
2010 Sep; 21(5):428-33. doi:
10.1002/pca.1213. [PMID: 20310075] - Paulwatt Nuclear, Damrong Sommit, Nattawut Boonyuen, Khanitha Pudhom. Butenolide and furandione from an endophytic Aspergillus terreus.
Chemical & pharmaceutical bulletin.
2010 Sep; 58(9):1221-3. doi:
10.1248/cpb.58.1221. [PMID: 20823603] - Joanna L Michel, Yegao Chen, Hongjie Zhang, Yue Huang, Aleksej Krunic, Jimmy Orjala, Mario Veliz, Kapil K Soni, Djaja Doel Soejarto, Armando Caceres, Alice Perez, Gail B Mahady. Estrogenic and serotonergic butenolides from the leaves of Piper hispidum Swingle (Piperaceae).
Journal of ethnopharmacology.
2010 May; 129(2):220-6. doi:
10.1016/j.jep.2010.03.008. [PMID: 20304039] - Mehdi Jalali-Heravi, Hadi Parastar, Heshmatollah Ebrahimi-Najafabadi. Self-modeling curve resolution techniques applied to comparative analysis of volatile components of Iranian saffron from different regions.
Analytica chimica acta.
2010 Mar; 662(2):143-54. doi:
10.1016/j.aca.2010.01.013. [PMID: 20171313] - Marnie E Light, Ben V Burger, Dan Staerk, Ladislav Kohout, Johannes Van Staden. Butenolides from plant-derived smoke: natural plant-growth regulators with antagonistic actions on seed germination.
Journal of natural products.
2010 Feb; 73(2):267-9. doi:
10.1021/np900630w. [PMID: 20078110] - Kajsa Kajander, Eveliina Myllyluoma, Sinikka Kyrönpalo, Martin Rasmussen, Pentti Sipponen, Ismo Mattila, Tuulikki Seppänen-Laakso, Heikki Vapaatalo, Matej Oresic, Riitta Korpela. Elevated pro-inflammatory and lipotoxic mucosal lipids characterise irritable bowel syndrome.
World journal of gastroenterology.
2009 Dec; 15(48):6068-74. doi:
10.3748/wjg.15.6068. [PMID: 20027679] - Gavin R Flematti, Emilio L Ghisalberti, Kingsley W Dixon, Robert D Trengove. Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke.
Journal of agricultural and food chemistry.
2009 Oct; 57(20):9475-80. doi:
10.1021/jf9028128. [PMID: 19785418] - Yi-Mei Wang, Hui-Jiao Wang, Shuang-Qing Peng. In ovo exposure of a Fusarium mycotoxin butenolide induces hepatic and renal oxidative damage in chick embryos, and antioxidants provide protections.
Toxicology in vitro : an international journal published in association with BIBRA.
2009 Oct; 23(7):1354-9. doi:
10.1016/j.tiv.2009.06.028. [PMID: 19573587] - Shoei-Sheng Lee, Yi-Shan Lin, Chien-Kuang Chen. Three adducts of butenolide and apigenin glycoside from the leaves of Machilus japonica.
Journal of natural products.
2009 Jul; 72(7):1249-52. doi:
10.1021/np9000653. [PMID: 19719245] - Hui-Jiao Wang, Yi-Mei Wang, Shuang-Qing Peng. Repeated administration of a Fusarium mycotoxin butenolide to rats induces hepatic lipid peroxidation and antioxidant defense impairment.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2009 Mar; 47(3):633-7. doi:
10.1016/j.fct.2008.12.025. [PMID: 19150382] - Hai-Ying Yang, Yi-Mei Wang, Shuang-Qing Peng. Basal expression of metallothionein suppresses butenolide-induced oxidative stress in liver homogenates in vitro.
Toxicon : official journal of the International Society on Toxinology.
2009 Feb; 53(2):246-53. doi:
10.1016/j.toxicon.2008.11.008. [PMID: 19084032] - Zhongli Shi, Junling Cao, Jinghong Chen, Siyuan Li, Zengtie Zhang, Bo Yang, Shuangqing Peng. Butenolide induced cytotoxicity by disturbing the prooxidant-antioxidant balance, and antioxidants partly quench in human chondrocytes.
Toxicology in vitro : an international journal published in association with BIBRA.
2009 Feb; 23(1):99-104. doi:
10.1016/j.tiv.2008.11.002. [PMID: 19056480] - Yi-Mei Wang, Jing-Bo Liu, Shuang-Qing Peng. Effects of Fusarium mycotoxin butenolide on myocardial mitochondria in vitro.
Toxicology mechanisms and methods.
2009 Feb; 19(2):79-85. doi:
10.1080/15376510802322802. [PMID: 19778250] - Yi-Mei Wang, Hui-Jiao Wang, Shuang-Qing Peng. Lipid peroxidation and antioxidant defense impairment in the hearts of chick embryos induced by in ovo exposure to Fusarium mycotoxin butenolide.
Toxicon : official journal of the International Society on Toxinology.
2008 Dec; 52(7):781-6. doi:
10.1016/j.toxicon.2008.08.006. [PMID: 18775738] - John Boukouvalas, Richard P Loach. General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid.
The Journal of organic chemistry.
2008 Oct; 73(20):8109-12. doi:
10.1021/jo8015924. [PMID: 18798671] - Neeru Jain, Glendon D Ascough, Johannes Van Staden. A smoke-derived butenolide alleviates HgCl2 and ZnCl2 inhibition of water uptake during germination and subsequent growth of tomato--possible involvement of aquaporins.
Journal of plant physiology.
2008 Sep; 165(13):1422-7. doi:
10.1016/j.jplph.2008.04.017. [PMID: 18565621] - Rukmal Ratnayake, B M Ratnayake Bandara, Siril Wijesundara, John K Macleod, Peta Simmonds, Veranja Karunaratne. Bioactivity and chemistry of the genus Hortonia.
Natural product research.
2008; 22(16):1393-402. doi:
10.1080/14786410701722433. [PMID: 19023800] - Brian T Murphy, Shugeng Cao, Peggy J Brodie, James S Miller, Fidy Ratovoson, Chris Birkinshaw, Etienne Rakotobe, Vincent E Rasamison, Karen Tendyke, Edward M Suh, David G I Kingston. Antiproliferative compounds of Artabotrys madagascariensis from the Madagascar rainforest.
Natural product research.
2008; 22(13):1169-75. doi:
10.1080/14786410701726525. [PMID: 18855218] - James McNulty, Joanna Poloczek, Vladimir Larichev, Nick H Werstiuk, Carly Griffin, Siyaram Pandey. Discovery of the apoptosis-inducing activity and high accumulation of the butenolides, menisdaurilide and aquilegiolide in Dicentra spectabilis.
Planta medica.
2007 Dec; 73(15):1543-47. doi:
10.1055/s-2007-990264. [PMID: 17999351] - Jing-Bo Liu, Yi-Mei Wang, Shuang-Qing Peng, Gang Han, Yan-Sheng Dong, Hai-Ying Yang, Chang-Hui Yan, Guo-Qiang Wang. Toxic effects of Fusarium mycotoxin butenolide on rat myocardium and primary culture of cardiac myocytes.
Toxicon : official journal of the International Society on Toxinology.
2007 Sep; 50(3):357-64. doi:
10.1016/j.toxicon.2007.04.014. [PMID: 17603091] - Yi-Mei Wang, Shuang-Qing Peng, Qi Zhou, Min-Wei Wang, Chang-Hui Yan, Guo-Qiang Wang, Hai-Ying Yang. The oxidative damage of butenolide to isolated erythrocyte membranes.
Toxicology in vitro : an international journal published in association with BIBRA.
2007 Aug; 21(5):863-9. doi:
10.1016/j.tiv.2007.02.009. [PMID: 17416482] - M Kawasaki, T Onaka, J Saito, H Hashimoto, H Suzuki, H Otsubo, H Fujihara, N Okimoto, H Ohnishi, T Nakamura, Y Ueta. Effects of the short chain sugar acid 2-buten-4-olide on the hypothalamo-pituitary-adrenal axis in normal and adjuvant-induced arthritic rats.
Journal of neuroendocrinology.
2007 Jan; 19(1):54-65. doi:
10.1111/j.1365-2826.2006.01503.x. [PMID: 17184486] - Makoto Kawasaki, Chiyo Yamaga, Tatsushi Onaka, Jun Saito, Takashi Mera, Hirofumi Hashimoto, Hiroaki Fujihara, Nobukazu Okimoto, Hideo Ohnishi, Toshitaka Nakamura, Yoichi Ueta. The short chain sugar acid, 2-buten-4-olide, activates oxytocin-secreting neurons but not arginine vasopressin-secreting neurons in the hypothalamus of rats.
Brain research.
2006 May; 1086(1):133-41. doi:
10.1016/j.brainres.2006.02.099. [PMID: 16616049] - Victor S Sobolev, Stephen T Deyrup, James B Gloer. New peanut (Arachis hypogaea) phytoalexin with prenylated benzenoid and but-2-enolide moieties.
Journal of agricultural and food chemistry.
2006 Mar; 54(6):2111-5. doi:
10.1021/jf052948o. [PMID: 16536583] - Hong-Jie Zhang, Van Hung Nguyen, Manh Cuong Nguyen, D Doel Soejarto, John M Pezzuto, Harry H Fong, Ghee Teng Tan. Sesquiterpenes and butenolides, natural anti-HIV constituents from Litsea verticillata.
Planta medica.
2005 May; 71(5):452-7. doi:
10.1055/s-2005-864142. [PMID: 15931585] - Yutaka Oomura, Shuji Aou, Ikuo Matsumoto, Toshiie Sakata. Physiological significance of 2-buten-4-olide (2-B4O), an endogenous satiety substance increased in the fasted state.
Experimental biology and medicine (Maywood, N.J.).
2003 Nov; 228(10):1146-55. doi:
10.1177/153537020322801008. [PMID: 14610253] - Dang Ngoc Quang, Toshihiro Hashimoto, Makiko Nukada, Isao Yamamoto, Masami Tanaka, Shigeru Takaoka, Yoshinori Asakawa. Two novel ravenelones from the edible mushroom Pulveroboletus ravenelii.
Chemical & pharmaceutical bulletin.
2003 Mar; 51(3):330-2. doi:
10.1248/cpb.51.330. [PMID: 12612423] - T Kinoshita. Chemical studies on the Philippine crude drug calumbibit (seeds of Caesalpinia bonduc): the isolation of new cassane diterpenes fused with alpha,beta-butenolide.
Chemical & pharmaceutical bulletin.
2000 Sep; 48(9):1375-7. doi:
10.1248/cpb.48.1375. [PMID: 10993244] - H Kaji, S Saito, K Shitsukawa, M Irahara, T Aono. The endogenous feeding suppressant, 2-buten-4-olide, impairs the pulsatile secretion of luteinizing hormone through endogenous opioid peptides.
European journal of endocrinology.
1998 Feb; 138(2):198-205. doi:
10.1530/eje.0.1380198. [PMID: 9506867] - I Matsumoto, Y Oomura, H Nishino, S Nemoto, S Aou, T Aikawa. Effects of 2-buten-4-olide, an endogenous satiety substance, on plasma glucose, corticosterone, and catecholamines.
The American journal of physiology.
1994 Feb; 266(2 Pt 2):R413-8. doi:
10.1152/ajpregu.1994.266.2.r413. [PMID: 8141398] - R F Vesonder, H Gasdorf, R E Peterson. Comparison of the cytotoxicities of Fusarium metabolites and Alternaria metabolite AAL-toxin to cultured mammalian cell lines.
Archives of environmental contamination and toxicology.
1993 May; 24(4):473-7. doi:
10.1007/bf01146164. [PMID: 8507101] - K Shitsukawa, M Irahara, T Kanematsu, K Azuma, T Aono. Effect of 2-buten-4-olide, an endogenous suppressant of feeding, on reproductive function in rats.
Acta endocrinologica.
1990 Nov; 123(5):571-6. doi:
10.1530/acta.0.1230571. [PMID: 2256437] - A Fukuda, Y Oomura, C R Plata-Salamán, T Minami, C Ito. A novel endogenous sugar acid depolarizes ventromedial hypothalamic neurons in vitro.
The American journal of physiology.
1988 Jul; 255(1 Pt 2):R134-40. doi:
10.1152/ajpregu.1988.255.1.r134. [PMID: 3394836] - E LEETE, H GREGORY, E G GROS. BIOSYNTHESIS OF PLANT STEROIDS. I. THE ORIGIN OF THE BUTENOLIDE RING OF DIGITOXIGENIN.
Journal of the American Chemical Society.
1965 Aug; 87(?):3475-9. doi:
10.1021/ja01093a034. [PMID: 14322539]