Protoanemonin (BioDeep_00000006412)

 

Secondary id: BioDeep_00000864142, BioDeep_00001868924

human metabolite PANOMIX_OTCML-2023 Toxin natural product


代谢物信息卡片


5-methylidene-2,5-dihydrofuran-2-one

化学式: C5H4O2 (96.0211)
中文名称: 5-亚甲基-2(5H)-呋喃酮, 原白头翁素
谱图信息: 最多检出来源 Viridiplantae(plant) 12.98%

分子结构信息

SMILES: C=C1C=CC(=O)O1
InChI: InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2

描述信息

Protoanemonin (sometimes called anemonol or ranunculol) is a toxin found in all plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is produced by an enzymatic process from the glucoside ranunculin. It is the lactone of 4-hydroxy-2,4-pentadienoic acid. A wounded plant releases the substance, causing itch, rashes or blistering on contact with the skin or mucosa. (Wikipedia)

同义名列表

7 个代谢物同义名

5-methylidene-2,5-dihydrofuran-2-one; cis-4-Methylenebut-2-en-4-olide; 4-Methylenebut-2-en-4-olide; 5-Methylene-2(5H)-furanone; 5-Methylene-2-furanone; Protoanemonin; Protoanemonin



数据库引用编号

15 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

148 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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ANXA5, CAT, LAMP1, MT3
Peripheral membrane protein 1 ANXA5
Endosome membrane 1 LAMP1
Nucleus 1 MT3
cytosol 4 ANXA5, CAT, LAMP1, MT3
Cell membrane 1 LAMP1
Golgi apparatus 1 ATRN
lysosomal membrane 1 LAMP1
sarcolemma 2 ANXA5, LAMP1
synaptic vesicle 2 LAMP1, MT3
Lysosome 1 LAMP1
plasma membrane 2 ATRN, LAMP1
Membrane 3 ANXA5, CAT, LAMP1
axon 1 MT3
extracellular exosome 4 ANXA5, ATRN, CAT, LAMP1
Lysosome membrane 1 LAMP1
extracellular space 2 ATRN, MT3
perinuclear region of cytoplasm 2 LAMP1, MT3
mitochondrion 1 CAT
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 1 CAT
Single-pass type I membrane protein 2 ATRN, LAMP1
extracellular region 2 ANXA5, CAT
mitochondrial outer membrane 1 MT3
astrocyte end-foot 1 MT3
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 1 CAT
external side of plasma membrane 2 ANXA5, LAMP1
multivesicular body 1 LAMP1
dendritic spine 1 MT3
focal adhesion 2 ANXA5, CAT
microtubule 1 MT3
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ANXA5
Late endosome 1 LAMP1
Zymogen granule membrane 1 ANXA5
Late endosome membrane 1 LAMP1
autophagosome membrane 1 LAMP1
[Isoform 3]: Secreted 1 ATRN
Melanosome 1 LAMP1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
azurophil granule membrane 1 LAMP1
vesicle membrane 1 ANXA5
ficolin-1-rich granule membrane 1 LAMP1
[Isoform 1]: Cell membrane 1 ATRN
ribosome 1 MT3
Autolysosome 1 LAMP1
catalase complex 1 CAT
inclusion body 1 MT3
endothelial microparticle 1 ANXA5
Cytolytic granule membrane 1 LAMP1
phagolysosome membrane 1 LAMP1


文献列表

  • Margit B Müller, Julia Bertrams, Florian C Stintzing. Stability of protoanemonin in plant extracts from Helleborus niger L. and Pulsatilla vulgaris Mill. Journal of pharmaceutical and biomedical analysis. 2020 Sep; 188(?):113370. doi: 10.1016/j.jpba.2020.113370. [PMID: 32497949]
  • L W D van Raamsdonk, W A Ozinga, L A P Hoogenboom, P P J Mulder, J G J Mol, M J Groot, H J van der Fels-Klerx, M de Nijs. Exposure assessment of cattle via roughages to plants producing compounds of concern. Food chemistry. 2015 Dec; 189(?):27-37. doi: 10.1016/j.foodchem.2015.02.050. [PMID: 26190597]
  • Michael Schink, Manuel Garcia-Käufer, Julia Bertrams, Sarina M Duckstein, Margit B Müller, Roman Huber, Florian C Stintzing, Carsten Gründemann. Differential cytotoxic properties of Helleborus niger L. on tumour and immunocompetent cells. Journal of ethnopharmacology. 2015 Jan; 159(?):129-36. doi: 10.1016/j.jep.2014.11.003. [PMID: 25446603]
  • D Schrenk, K-H Merz, K Jochims. Feasibility study of nonclinical safety assessments on homeopathic preparations using the example of protoanemonin in Pulsatilla pratensis L. Regulatory toxicology and pharmacology : RTP. 2013 Jun; 66(1):104-8. doi: 10.1016/j.yrtph.2013.03.004. [PMID: 23535118]
  • Fangming Jin, Christian Narkowicz, Glenn A Jacobson. Protoanemonin content variation between Clematis spp.: leaf, stem and root. Natural product communications. 2013 Feb; 8(2):211-2. doi: ". [PMID: 23513731]
  • Simon Wan Chan, Peter C Dedon. The biological and metabolic fates of endogenous DNA damage products. Journal of nucleic acids. 2010 Dec; 2010(?):929047. doi: 10.4061/2010/929047. [PMID: 21209721]
  • Hamid Sobhanian, Roya Razavizadeh, Yohei Nanjo, Ali Akbar Ehsanpour, Ferdous Rastgar Jazii, Nasrin Motamed, Setsuko Komatsu. Proteome analysis of soybean leaves, hypocotyls and roots under salt stress. Proteome science. 2010 Mar; 8(?):19. doi: 10.1186/1477-5956-8-19. [PMID: 20350314]
  • Sarah E Edwards, Kathrin E Martz, Anja Rogge, Michael Heinrich. Edaphic and Phytochemical Factors as Predictors of Equine Grass Sickness Cases in the UK. Frontiers in pharmacology. 2010; 1(?):122. doi: 10.3389/fphar.2010.00122. [PMID: 21833167]
  • Sabreen F Fostok, Rima A Ezzeddine, Fadia R Homaidan, Jamal A Al-Saghir, Ralph G Salloum, Najat A Saliba, Rabih S Talhouk. Interleukin-6 and Cyclooxygenase-2 downregulation by fatty-acid fractions of Ranunculus constantinopolitanus. BMC complementary and alternative medicine. 2009 Nov; 9(?):44. doi: 10.1186/1472-6882-9-44. [PMID: 19917107]
  • Gunjan M Modi, Christy B Doherty, Rajani Katta, Ida F Orengo. Irritant contact dermatitis from plants. Dermatitis : contact, atopic, occupational, drug. 2009 Mar; 20(2):63-78. doi: . [PMID: 19426612]
  • Katja Witzel, Annette Weidner, Giridara-Kumar Surabhi, Andreas Börner, Hans-Peter Mock. Salt stress-induced alterations in the root proteome of barley genotypes with contrasting response towards salinity. Journal of experimental botany. 2009; 60(12):3545-57. doi: 10.1093/jxb/erp198. [PMID: 19671579]
  • Paolo Maria Guarrera, Giovanni Salerno, Giulia Caneva. Food, flavouring and feed plant traditions in the Tyrrhenian sector of Basilicata, Italy. Journal of ethnobiology and ethnomedicine. 2006 Sep; 2(?):37. doi: 10.1186/1746-4269-2-37. [PMID: 16959031]
  • Ian A Southwell. 25 years of natural product R&D with New South Wales agriculture. Molecules (Basel, Switzerland). 2005 Oct; 10(10):1232-41. doi: 10.3390/10101232. [PMID: 18007515]
  • Semsettin Karaca, Mustafa Kulac, Hudaverdi Kucuker. Phytodermatitis caused by Ceratocephalus falcatus (Ranunculacea). European journal of dermatology : EJD. 2005 Sep; 15(5):404-5. doi: ". [PMID: 16172054]
  • Andreas Jürgens, Stefan Dötterl. Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species. American journal of botany. 2004 Dec; 91(12):1969-80. doi: 10.3732/ajb.91.12.1969. [PMID: 21652345]
  • H Haupt. [Poisonous and less poisonous plants. 52]. Kinderkrankenschwester : Organ der Sektion Kinderkrankenpflege. 2001 Aug; 20(8):335. doi: ". [PMID: 14584174]
  • R Blasco, R M Wittich, M Mallavarapu, K N Timmis, D H Pieper. From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway. The Journal of biological chemistry. 1995 Dec; 270(49):29229-35. doi: 10.1074/jbc.270.49.29229. [PMID: 7493952]
  • G Pratviel, M Pitié, J Bernadou, B Meunier. Mechanism of DNA cleavage by cationic manganese porphyrins: hydroxylations at the 1'-carbon and 5'-carbon atoms of deoxyriboses as initial damages. Nucleic acids research. 1991 Nov; 19(22):6283-8. doi: 10.1093/nar/19.22.6283. [PMID: 1720241]
  • M L Martin, A V Ortíz de Urbina, M J Montero, R Carrón, L San Román. Pharmacologic effects of lactones isolated from Pulsatilla alpina subsp. apiifolia. Journal of ethnopharmacology. 1988 Dec; 24(2-3):185-91. doi: 10.1016/0378-8741(88)90150-x. [PMID: 3267028]
  • D Mares. Antimicrobial activity of protoanemonin, a lactone from ranunculaceous plants. Mycopathologia. 1987 Jun; 98(3):133-40. doi: 10.1007/bf00437648. [PMID: 3587338]
  • K V Thimann, W D Bonner. Inhibition of Plant Growth by Protoanemonin and Coumarin, and Its Prevention by Bal. Proceedings of the National Academy of Sciences of the United States of America. 1949 Jun; 35(6):272-6. doi: 10.1073/pnas.35.6.272. [PMID: 16588891]
  • K V THIMANN, W D BONNER. Inhibition of plant growth by protoanemonin and coumarin and its prevention by BAL. Science (New York, N.Y.). 1949 Apr; 109(2835):444. doi: ". [PMID: 18224966]