alpha-Methylene-gamma-butyrolactone (BioDeep_00000000994)

 

Secondary id: BioDeep_00000870891, BioDeep_00001867578

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs


代谢物信息卡片


4-(3-FORMYL-2,5-DIMETHYL-1H-PYRROL-1-YL)BENZENECARBOXYLICACID

化学式: C5H6O2 (98.0367776)
中文名称: α-亚甲基-γ-丁内酯, 郁金香素A, 2-甲烯基丁内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

分子结构信息

SMILES: C=C1CCOC1=O
InChI: InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

描述信息

Alpha-methylene gamma-butyrolactone is a butan-4-olide having a methylene group at the 3-position. It has a role as a gastrointestinal drug and an anti-ulcer drug.
alpha-Methylene-gamma-butyrolactone is a natural product found in Tulipa agenensis, Tulipa humilis, and other organisms with data available.
D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents
Tulipalin A (α-Methylene butyrolactone) is a glycoside. Tulipalin A is a causative allergen that induces Allergic contact dermatitides[1]. Tulipalin A (α-Methylene butyrolactone) at low dose affects the functionality of immune cells, such as Jurkat T cells[2].
Tulipalin A (α-Methylene butyrolactone) is a glycoside. Tulipalin A is a causative allergen that induces Allergic contact dermatitides[1]. Tulipalin A (α-Methylene butyrolactone) at low dose affects the functionality of immune cells, such as Jurkat T cells[2].

同义名列表

45 个代谢物同义名

4-(3-FORMYL-2,5-DIMETHYL-1H-PYRROL-1-YL)BENZENECARBOXYLICACID; 3-METHYLENEDIHYDROFURAN-2(3H)-ONE (STABILIZED WITH 1\\% BHT); alpha-Methylene-gamma-butyrolactone, 97\\%; .alpha.-Methylene-.gamma.-butyrolactone; alpha -Methylene- gamma -butyrolactone; 2(3H)-Furanone, dihydro-3-methylene- (; alpha-methylidene-gamma-butyrolactone; InChI=1/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H; 2(3H)-Furanone, dihydro-3-methylene-; .ALPHA.-METHYLENE BUTYROLACTONE [MI]; alpha-methylene gamma-butyrolactone; alpha-Methylene-gamma-butyrolactone; 3-Methylenedihydro-2(3H)-furanone #; Dihydro-3-methylene-2(3H)-furanone; 3-methylenedihydrofuran-2 (3H)-one; 3-Methylenedihydro-2(3H)-furanone; 3-methylenedihydrofuran-2(3H)-one; dihydro-3-methylene-(3h)-furanone; 3-Methylenedihydro-2(3H)-fuanone; 3-methylenetetrahydrofuran-2-one; METHYLENE BUTYROLACTONE, ALPHA-; .alpha.-Methylene butyrolactone; Α-methylidene-γ-butyrolactone; a-Methylidene-g-butyrolactone; alpha-Methylene butyrolactone; a-Methylene g-butyrolactone; a-Methylene-g-butyrolactone; Α-methylene γ-butyrolactone; a-methylene-y-butyrolactone; Α-methylene-γ-butyrolactone; 3-methylideneoxolan-2-one; Α-methylene butyrolactone; a-Methylene butyrolactone; -Methylene butyrolactone; 2-Methylenebutanolactone; a-methyl-y-butyrolactone; 2-methylenebutyrolactone; TULIPALIN A [INCI]; TULIPALIN 98; TULIPALINE A; Tulipalin A; Securolide; AI3-63021; Tulipane; LMSV-6



数据库引用编号

14 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)

35 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

  • Hong-Wei He, Dan Xu, Ke-Huan Wu, Zheng-Yi Lu, Xili Liu, Gong Xu. Discovery of novel salicylaldehyde derivatives incorporating an α-methylene-γ-butyrolactone moiety as fungicidal agents. Pest management science. 2023 Dec; 79(12):5015-5028. doi: 10.1002/ps.7703. [PMID: 37544900]
  • Luwei Li, Deyou Yang, Heng Li, Guangyou Chen, Peng Lei, Yanqing Gao, Juntao Feng. Heterocycle-Substituted α-Methylene-γ-Butyrolactones Derivatives Synthesis, Antifungal Activity, and 3D-QSAR. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c02117. [PMID: 37432089]
  • Hong-Wei He, Fei-Yu Wang, Danyang Zhang, Cai-Yun Chen, Dan Xu, Huan Zhou, Xili Liu, Gong Xu. Discovery of Novel α-Methylene-γ-Butyrolactone Derivatives Containing Vanillin Moieties as Antiviral and Antifungal Agents. Journal of agricultural and food chemistry. 2022 Aug; 70(33):10316-10325. doi: 10.1021/acs.jafc.2c03632. [PMID: 35960686]
  • Xue Li, Lingmei Kong, Qihong Yang, Aizhu Duan, Xiaoman Ju, Bicheng Cai, Lin Chen, Tao An, Yan Li. Parthenolide inhibits ubiquitin-specific peptidase 7 (USP7), Wnt signaling, and colorectal cancer cell growth. The Journal of biological chemistry. 2020 03; 295(11):3576-3589. doi: 10.1074/jbc.ra119.011396. [PMID: 32029476]
  • Taiji Nomura, Shinjiro Ogita, Yasuo Kato. One-Step Enzymatic Synthesis of 1-Tuliposide A Using Tuliposide-Converting Enzyme. Applied biochemistry and biotechnology. 2019 May; 188(1):12-28. doi: 10.1007/s12010-018-2903-3. [PMID: 30284210]
  • Iffat Hassan, Farhan Rasool, Saniya Akhtar, Afifa Kamili, Parvaiz Rather, Raihana Kanth, Yasmeen Bhat, Shagufta Rather, Syed Mubashir, Atiya Yaseen, Safia Bashir. Contact dermatitis caused by tulips: identification of contact sensitizers in tulip workers of Kashmir Valley in North India. Contact dermatitis. 2018 Jan; 78(1):64-69. doi: 10.1111/cod.12870. [PMID: 28940507]
  • Yongling Wu, Delong Wang, Yanqing Gao, Juntao Feng, Xing Zhang. New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities. Molecules (Basel, Switzerland). 2016 Jan; 21(2):130. doi: 10.3390/molecules21020130. [PMID: 26805804]
  • Camille Debeuckelaere, Valérie Berl, Karim Elbayed, François-Marie Moussallieh, Izzie-Jacques Namer, J-P Lepoittevin. Matrix Effect of Human Reconstructed Epidermis on the Chemoselectivity of a Skin Sensitizing α-Methylene-γ-Butyrolactone: Consequences for the Development of in Chemico Alternative Methods. Chemical research in toxicology. 2015 Nov; 28(11):2192-8. doi: 10.1021/acs.chemrestox.5b00363. [PMID: 26496248]
  • Pierluigi Caboni, Laura Tronci, Barbara Liori, Graziella Tocco, Nicola Sasanelli, Andrea Diana. Tulipaline A: structure-activity aspects as a nematicide and V-ATPase inhibitor. Pesticide biochemistry and physiology. 2014 Jun; 112(?):33-9. doi: 10.1016/j.pestbp.2014.05.002. [PMID: 24974115]
  • Feng Jun-Tao, Wang De-Long, Wu Yong-Ling, Yan He, Zhang Xing. New antifungal scaffold derived from a natural pharmacophore: synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium. Bioorganic & medicinal chemistry letters. 2013 Aug; 23(15):4393-7. doi: 10.1016/j.bmcl.2013.05.073. [PMID: 23777779]
  • Jihoon Shin, Youngmin Lee, William B Tolman, Marc A Hillmyer. Thermoplastic elastomers derived from menthide and tulipalin A. Biomacromolecules. 2012 Nov; 13(11):3833-40. doi: 10.1021/bm3012852. [PMID: 23062206]
  • Quan Zhang, Yaxin Lu, Yahui Ding, Jiadai Zhai, Qing Ji, Weiwei Ma, Ming Yang, Hongxia Fan, Jing Long, Zhongsheng Tong, Yehui Shi, Yongsheng Jia, Bin Han, Wenpeng Zhang, Chuanjiang Qiu, Xiaoyan Ma, Qiuying Li, Qianqian Shi, Haoliang Zhang, Dongmei Li, Jing Zhang, Jianping Lin, Lu-Yuan Li, Yingdai Gao, Yue Chen. Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells. Journal of medicinal chemistry. 2012 Oct; 55(20):8757-69. doi: 10.1021/jm301064b. [PMID: 22985027]
  • E Rozas-Muñoz, J P Lepoittevin, R M Pujol, A Giménez-Arnau. Allergic contact dermatitis to plants: understanding the chemistry will help our diagnostic approach. Actas dermo-sifiliograficas. 2012 Jul; 103(6):456-77. doi: 10.1016/j.ad.2011.07.017. [PMID: 22217935]
  • Taiji Nomura, Shinjiro Ogita, Yasuo Kato. A novel lactone-forming carboxylesterase: molecular identification of a tuliposide A-converting enzyme in tulip. Plant physiology. 2012 Jun; 159(2):565-78. doi: 10.1104/pp.112.195388. [PMID: 22474185]
  • Anil Pareek, Manish Suthar, Garvendra S Rathore, Vijay Bansal. Feverfew (Tanacetum parthenium L.): A systematic review. Pharmacognosy reviews. 2011 Jan; 5(9):103-10. doi: 10.4103/0973-7847.79105. [PMID: 22096324]
  • Yasuo Kato, Kazuaki Shoji, Makoto Ubukata, Kengo Shigetomi, Yukio Sato, Noriyuki Nakajima, Shinjiro Ogita. Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana. Bioscience, biotechnology, and biochemistry. 2009 Aug; 73(8):1895-7. doi: 10.1271/bbb.90226. [PMID: 19661715]
  • Jean-Pierre Lepoittevin, Valérie Berl, Elena Giménez-Arnau. Alpha-methylene-gamma-butyrolactones: versatile skin bioactive natural products. Chemical record (New York, N.Y.). 2009; 9(5):258-70. doi: 10.1002/tcr.200900013. [PMID: 19937861]
  • H-O Pae, G-S Jeong, H-S Kim, W H Woo, H Y Rhew, H S Kim, D H Sohn, Y-C Kim, H-T Chung. Costunolide inhibits production of tumor necrosis factor-alpha and interleukin-6 by inducing heme oxygenase-1 in RAW264.7 macrophages. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2007 Dec; 56(12):520-6. doi: 10.1007/s00011-007-7015-4. [PMID: 18210237]
  • Gil-Saeng Jeong, Hyun-Ock Pae, Sun-Oh Jeong, Youn-Chul Kim, Tae-Oh Kwon, Ho Sub Lee, Nam-Song Kim, Seok Don Park, Hun-Taeg Chung. The alpha-methylene-gamma-butyrolactone moiety in dehydrocostus lactone is responsible for cytoprotective heme oxygenase-1 expression through activation of the nuclear factor E2-related factor 2 in HepG2 cells. European journal of pharmacology. 2007 Jun; 565(1-3):37-44. doi: 10.1016/j.ejphar.2007.02.053. [PMID: 17391667]
  • Caspar Elo Christensen, Birthe B Kragelund, Penny von Wettstein-Knowles, Anette Henriksen. Structure of the human beta-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase. Protein science : a publication of the Protein Society. 2007 Feb; 16(2):261-72. doi: 10.1110/ps.062473707. [PMID: 17242430]
  • Beatriz Tavares, Graça Loureiro, Celso Pereira, Celso Chieira. Home gardening may be a risk factor for contact dermatitis to Alstroemeria. Allergologia et immunopathologia. 2006 Mar; 34(2):73-5. doi: 10.1157/13086751. [PMID: 16606550]
  • Javier A Menendez, Ruth Lupu, Ramon Colomer. Targeting fatty acid synthase: potential for therapeutic intervention in her-2/neu-overexpressing breast cancer. Drug news & perspectives. 2005 Jul; 18(6):375-85. doi: 10.1358/dnp.2005.18.6.927929. [PMID: 16247515]
  • Nengyu Yang, Joanne S Kays, Tiffanie R Skillman, Lorri Burris, Thomas W Seng, Craig Hammond. C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA. The Journal of pharmacology and experimental therapeutics. 2005 Jan; 312(1):127-33. doi: 10.1124/jpet.104.074104. [PMID: 15356215]
  • Guochun He, Hideyuki Matsuura, Teruhiko Yoshihara. Isolation of an alpha-methylene-gamma-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae. Phytochemistry. 2004 Oct; 65(20):2803-7. doi: 10.1016/j.phytochem.2004.08.011. [PMID: 15474567]
  • Hiroshi Shimoda, Kiyofumi Ninomiya, Norihisa Nishida, Tomoe Yoshino, Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa. Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action. Bioorganic & medicinal chemistry letters. 2003 Jan; 13(2):223-8. doi: 10.1016/s0960-894x(02)00889-2. [PMID: 12482428]
  • H Fuchino, T Koide, M Takahashi, S Sekita, M Satake. New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities. Planta medica. 2001 Oct; 67(7):647-53. doi: 10.1055/s-2001-17349. [PMID: 11582544]
  • B B Patel, T G Waddell, R M Pagni. Explaining photodermatosis: cyclopentenone vs. alpha-methylene-gamma-lactone natural products. Fitoterapia. 2001 Jun; 72(5):511-5. doi: 10.1016/s0367-326x(01)00257-x. [PMID: 11429245]
  • J D Guin, H Franks. Fingertip dermatitis in a retail florist. Cutis. 2001 Apr; 67(4):328-30. doi: . [PMID: 11324397]
  • M Yoshikawa, H Shimoda, T Uemura, T Morikawa, Y Kawahara, H Matsuda. Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity. Bioorganic & medicinal chemistry. 2000 Aug; 8(8):2071-7. doi: 10.1016/s0968-0896(00)00127-9. [PMID: 11003152]
  • L P Christensen. Direct release of the allergen tulipalin A from Alstroemeria cut flowers: a possible source of airborne contact dermatitis?. Contact dermatitis. 1999 Dec; 41(6):320-4. doi: 10.1111/j.1600-0536.1999.tb06180.x. [PMID: 10617212]
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  • W A Groenewegen, D W Knight, S Heptinstall. Compounds extracted from feverfew that have anti-secretory activity contain an alpha-methylene butyrolactone unit. The Journal of pharmacy and pharmacology. 1986 Sep; 38(9):709-12. doi: 10.1111/j.2042-7158.1986.tb03118.x. [PMID: 2877077]
  • K B Diamond, G R Warren, J H Cardellina. Native American food and medicinal plants. 3. alpha-Methylene butyrolactone from Erythronium grandiflorum Pursh. Journal of ethnopharmacology. 1985 Sep; 14(1):99-101. doi: 10.1016/0378-8741(85)90034-0. [PMID: 4087925]
  • A Cheminat, J L Stampf, C Benezra. Allergic contact dermatitis to laurel (Laurus nobilis L.): isolation and identification of haptens. Archives of dermatological research. 1984; 276(3):178-81. doi: 10.1007/bf00414016. [PMID: 6476889]
  • B M Hausen, E Prater, H Schubert. The sensitizing capacity of Alstroemeria cultivars in man and guinea pig. Remarks on the occurrence, quantity and irritant and sensitizing potency of their constituents tuliposide A and tulipalin A (alpha-methylene-gamma-butyrolactone). Contact dermatitis. 1983 Jan; 9(1):46-54. doi: 10.1111/j.1600-0536.1983.tb04625.x. [PMID: 6839738]