Cynaropicrin (BioDeep_00000000048)

 

Secondary id: BioDeep_00000310462, BioDeep_00001869600

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-

化学式: C19H22O6 (346.1416312)
中文名称: 菜蓟苦素
谱图信息: 最多检出来源 Viridiplantae(otcml) 12.12%

分子结构信息

SMILES: C=C(CO)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12
InChI: InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2

描述信息

Constituent of Cynara scolymus (artichoke). Cynaropicrin is found in cardoon, globe artichoke, and root vegetables.
Cynaropicrin is found in cardoon. Cynaropicrin is a constituent of Cynara scolymus (artichoke).
Cynaropicrin is a sesquiterpene lactone.
Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available.
See also: Cynara scolymus leaf (part of).
D009676 - Noxae > D003603 - Cytotoxins
Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.
Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

同义名列表

13 个代谢物同义名

8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate; Cynaropicrin; Saupirin; 2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-; 2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-; [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate; 2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester; 2-Propenoic acid,2-(hydroxymethyl)-,(3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-ylester; 8-Hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate; Cynaropicrin - Cynara cardunculus (artichoke); MEGxp0_001095; Cynaropikrin; ACon1_000045



数据库引用编号

28 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)

115 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

  • Joelle C Boulos, Ejlal A Omer, Daniela Rigano, Carmen Formisano, Manik Chatterjee, Ellen Leich, Sabine M Klauck, Le-Tian Shan, Thomas Efferth. Cynaropicrin disrupts tubulin and c-Myc-related signaling and induces parthanatos-type cell death in multiple myeloma. Acta pharmacologica Sinica. 2023 Jun; ?(?):. doi: 10.1038/s41401-023-01117-3. [PMID: 37344563]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Mariachiara Spennato, Ottavia Maria Roggero, Simona Varriale, Fioretta Asaro, Angelo Cortesi, Jan Kašpar, Enrico Tongiorgi, Cinzia Pezzella, Lucia Gardossi. Neuroprotective Properties of Cardoon Leaves Extracts against Neurodevelopmental Deficits in an In Vitro Model of Rett Syndrome Depend on the Extraction Method and Harvest Time. Molecules (Basel, Switzerland). 2022 Dec; 27(24):. doi: 10.3390/molecules27248772. [PMID: 36557905]
  • Halima Hajji, Marwa Alaqarbeh, Tahar Lakhlifi, Mohammed Aziz Ajana, Nada Alsakhen, Mohammed Bouachrine. Computational approach investigation bioactive molecules from Saussurea Costus plant as SARS-CoV-2 main protease inhibitors using reverse docking, molecular dynamics simulation, and pharmacokinetic ADMET parameters. Computers in biology and medicine. 2022 Oct; 150(?):106209. doi: 10.1016/j.compbiomed.2022.106209. [PMID: 36257276]
  • Tomoko Matsumoto, Souichi Nakashima, Seikou Nakamura, Yasunao Hattori, Tomoshige Ando, Hisashi Matsuda. Inhibitory effects of cynaropicrin and related sesquiterpene lactones from leaves of artichoke (Cynara scolymus L.) on induction of iNOS in RAW264.7 cells and its high-affinity proteins. Journal of natural medicines. 2021 Mar; 75(2):381-392. doi: 10.1007/s11418-020-01479-6. [PMID: 33484417]
  • Danlei Cai, Hongdan Duan, Yangshan Fu, Zhongfeng Cheng. Renal Tissue Damage Induced by Acute Kidney Injury in Sepsis Rat Model Is Inhibited by Cynaropicrin via IL-1β and TNF-α Down-Regulation. Doklady. Biochemistry and biophysics. 2021 Mar; 497(1):151-157. doi: 10.1134/s1607672921020022. [PMID: 33895932]
  • Teresa Brás, Daniela Rosa, Ana C Gonçalves, Andreia C Gomes, Vítor D Alves, João G Crespo, Maria F Duarte, Luísa A Neves. Development of bioactive films based on chitosan and Cynara cardunculus leaves extracts for wound dressings. International journal of biological macromolecules. 2020 Nov; 163(?):1707-1718. doi: 10.1016/j.ijbiomac.2020.09.109. [PMID: 32961186]
  • Saverio M Lepore, Valentina Maggisano, Giovanni E Lombardo, Jessica Maiuolo, Vincenzo Mollace, Stefania Bulotta, Diego Russo, Marilena Celano. Antiproliferative Effects of Cynaropicrin on Anaplastic Thyroid Cancer Cells. Endocrine, metabolic & immune disorders drug targets. 2019; 19(1):59-66. doi: 10.2174/1871530318666180928153241. [PMID: 30264682]
  • Abolfazl Shakeri, Elaheh Amini, Javad Asili, Milena Masullo, Sonia Piacente, Mehrdad Iranshahi. Screening of several biological activities induced by different sesquiterpene lactones isolated from Centaurea behen L. and Rhaponticum repens (L.) Hidalgo. Natural product research. 2018 Jun; 32(12):1436-1440. doi: 10.1080/14786419.2017.1344661. [PMID: 28641489]
  • Antonio Colantuono, Rosalia Ferracane, Paola Vitaglione. Potential bioaccessibility and functionality of polyphenols and cynaropicrin from breads enriched with artichoke stem. Food chemistry. 2018 Apr; 245(?):838-844. doi: 10.1016/j.foodchem.2017.11.099. [PMID: 29287449]
  • Ana Margarida Ferro, Patrícia Ramos, Ângela Guerra, Paula Parreira, Teresa Brás, Olinda Guerreiro, Eliana Jerónimo, Carmen Capel, Juan Capel, Fernando J Yuste-Lisbona, Maria F Duarte, Rafael Lozano, M Margarida Oliveira, Sónia Gonçalves. Haplotype analysis of the germacrene A synthase gene and association with cynaropicrin content and biological activities in Cynara cardunculus. Molecular genetics and genomics : MGG. 2018 Apr; 293(2):417-433. doi: 10.1007/s00438-017-1388-z. [PMID: 29143866]
  • Emanuelle L P de Faria, Rafael S do Carmo, Ana Filipa M Cláudio, Carmen S R Freire, Mara G Freire, Armando J D Silvestre. Deep Eutectic Solvents as Efficient Media for the Extraction and Recovery of Cynaropicrin from Cynara cardunculus L. Leaves. International journal of molecular sciences. 2017 Oct; 18(11):. doi: 10.3390/ijms18112276. [PMID: 29084184]
  • Mila Radan, Ivana Carev, Vele Tešević, Olivera Politeo, Vedrana Čikeš Čulić. Qualitative HPLC-DAD/ESI-TOF-MS Analysis, Cytotoxic, and Apoptotic Effects of Croatian Endemic Centaurea ragusina L. Aqueous Extracts. Chemistry & biodiversity. 2017 Sep; 14(9):. doi: 10.1002/cbdv.201700099. [PMID: 28591430]
  • Carmen Formisano, Carmina Sirignano, Daniela Rigano, Giuseppina Chianese, Gokhan Zengin, Ean-Jeong Seo, Thomas Efferth, Orazio Taglialatela-Scafati. Antiproliferative activity against leukemia cells of sesquiterpene lactones from the Turkish endemic plant Centaurea drabifolia subsp. detonsa. Fitoterapia. 2017 Jul; 120(?):98-102. doi: 10.1016/j.fitote.2017.05.016. [PMID: 28579551]
  • Imke F Wulsten, Thais A Costa-Silva, Juliana T Mesquita, Marta L Lima, Mariana K Galuppo, Noemi N Taniwaki, Samanta E T Borborema, Fernando B Da Costa, Thomas J Schmidt, Andre G Tempone. Investigation of the Anti-Leishmania (Leishmania) infantum Activity of Some Natural Sesquiterpene Lactones. Molecules (Basel, Switzerland). 2017 Apr; 22(5):. doi: 10.3390/molecules22050685. [PMID: 28441357]
  • Antonio Russo, Mariarita Perri, Erika Cione, Maria Luisa Di Gioia, Monica Nardi, Maria Cristina Caroleo. Biochemical and chemical characterization of Cynara cardunculus L. extract and its potential use as co-adjuvant therapy of chronic myeloid leukemia. Journal of ethnopharmacology. 2017 Apr; 202(?):184-191. doi: 10.1016/j.jep.2017.03.026. [PMID: 28323047]
  • Patrícia A B Ramos, Ângela R Guerra, Olinda Guerreiro, Sónia A O Santos, Helena Oliveira, Carmen S R Freire, Armando J D Silvestre, Maria F Duarte. Antiproliferative Effects of Cynara cardunculus L. var. altilis (DC) Lipophilic Extracts. International journal of molecular sciences. 2016 Dec; 18(1):. doi: 10.3390/ijms18010063. [PMID: 28036090]
  • Carlos Rial, Benito F García, Rosa M Varela, Ascensión Torres, José M G Molinillo, Francisco A Macías. The Joint Action of Sesquiterpene Lactones from Leaves as an Explanation for the Activity of Cynara cardunculus. Journal of agricultural and food chemistry. 2016 Aug; 64(33):6416-24. doi: 10.1021/acs.jafc.6b02678. [PMID: 27487046]
  • Mahmoud Fahmi Elsebai, George Koutsoudakis, Verónica Saludes, Gemma Pérez-Vilaró, Ari Turpeinen, Sampo Mattila, Anna Maria Pirttilä, Fabien Fontaine-Vive, Mohamed Mehiri, Andreas Meyerhans, Juana Diez. Pan-genotypic Hepatitis C Virus Inhibition by Natural Products Derived from the Wild Egyptian Artichoke. Journal of virology. 2016 02; 90(4):1918-30. doi: 10.1128/jvi.02030-15. [PMID: 26656684]
  • Mohamed-Elamir F Hegazy, Abeer Y Ibrahim, Tarik A Mohamed, Abdelaaty A Shahat, Ali M El Halawany, Nahla S Abdel-Azim, Mansour S Alsaid, Paul W Paré. Sesquiterpene Lactones from Cynara cornigera: Acetyl Cholinesterase Inhibition and In Silico Ligand Docking. Planta medica. 2016 Jan; 82(1-2):138-46. doi: 10.1055/s-0035-1558088. [PMID: 26441064]
  • K Eljounaidi, C Comino, A Moglia, K Cankar, A Genre, A Hehn, F Bourgaud, J Beekwilder, S Lanteri. Accumulation of cynaropicrin in globe artichoke and localization of enzymes involved in its biosynthesis. Plant science : an international journal of experimental plant biology. 2015 Oct; 239(?):128-36. doi: 10.1016/j.plantsci.2015.07.020. [PMID: 26398797]
  • Ken-ichi Yamada, Yuji Ishii, Tomoki Takeda, Hiroaki Kuroki, Chikage Mitoma, Hiroshi Uchi, Masutaka Furue, Hideyuki Yamada. [Effect of Cynaropicrin on 2,3,4,7,8-Pentachlorodibenzofuran-induced Wasting Syndrome and Oxidative Stress]. Fukuoka igaku zasshi = Hukuoka acta medica. 2015 May; 106(5):169-75. doi: . [PMID: 26226680]
  • Cristiane França da Silva, Denise da Gama Jaen Batista, Julianna Siciliano De Araújo, Marcos Meuser Batista, Jessica Lionel, Elen Mello de Souza, Erica Ripoll Hammer, Patricia Bernardino da Silva, Maria De Mieri, Michael Adams, Stefanie Zimmermann, Matthias Hamburger, Reto Brun, Wolfgang Schühly, Maria de Nazaré Correia Soeiro. Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivo. Antimicrobial agents and chemotherapy. 2013 Nov; 57(11):5307-14. doi: 10.1128/aac.00595-13. [PMID: 23939901]
  • Tsholofelo A Mokoka, Peter K Xolani, Stefanie Zimmermann, Yoshie Hata, Michael Adams, Marcel Kaiser, Nivan Moodley, Vinesh Maharaj, Neil A Koorbanally, Matthias Hamburger, Reto Brun, Gerda Fouche. Antiprotozoal screening of 60 South African plants, and the identification of the antitrypanosomal germacranolides schkuhrin I and II. Planta medica. 2013 Sep; 79(14):1380-4. doi: 10.1055/s-0033-1350691. [PMID: 23929246]
  • Yuka Tsuda Tanaka, Kiyotaka Tanaka, Hiroyuki Kojima, Tomoji Hamada, Teruaki Masutani, Makoto Tsuboi, Yukihiro Akao. Cynaropicrin from Cynara scolymus L. suppresses photoaging of skin by inhibiting the transcription activity of nuclear factor-kappa B. Bioorganic & medicinal chemistry letters. 2013 Jan; 23(2):518-23. doi: 10.1016/j.bmcl.2012.11.034. [PMID: 23232059]
  • Barbara Menin, Cinzia Comino, Ezio Portis, Andrea Moglia, Katarina Cankar, Harro J Bouwmeester, Sergio Lanteri, Jules Beekwilder. Genetic mapping and characterization of the globe artichoke (+)-germacrene A synthase gene, encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone cynaropicrin. Plant science : an international journal of experimental plant biology. 2012 Jul; 190(?):1-8. doi: 10.1016/j.plantsci.2012.03.006. [PMID: 22608514]
  • Stefanie Zimmermann, Marcel Kaiser, Reto Brun, Matthias Hamburger, Michael Adams. Cynaropicrin: the first plant natural product with in vivo activity against Trypanosoma brucei. Planta medica. 2012 Apr; 78(6):553-6. doi: 10.1055/s-0031-1298241. [PMID: 22331812]
  • Valerio Pieri, Hermann Stuppner. Quantification of cynaropicrin in artichoke leaf extracts by ¹H NMR spectroscopy. Planta medica. 2011 Oct; 77(15):1756-8. doi: 10.1055/s-0030-1271083. [PMID: 21567361]
  • Helena Sovová, Lubomír Opletal, Marie Sajfrtová, Milena Bártlová. Supercritical fluid extraction of cynaropicrin and 20-hydroxyecdysone from Leuzea carthamoides DC. Journal of separation science. 2008 May; 31(8):1387-92. doi: 10.1002/jssc.200700496. [PMID: 18383243]
  • Kyungsu Kang, Hee Ju Lee, Chul Young Kim, Saet Byoul Lee, Jigjidsuren Tunsag, Dulamjav Batsuren, Chu Won Nho. The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme. Biological & pharmaceutical bulletin. 2007 Dec; 30(12):2352-9. doi: 10.1248/bpb.30.2352. [PMID: 18057725]
  • Fernanda Emendörfer, Fabiane Emendörfer, Fernanda Bellato, Vânia Floriani Noldin, Valdir Cechinel-Filho, Rosendo Augusto Yunes, Franco Delle Monache, Alcíbia Maia Cardozo. Antispasmodic activity of fractions and cynaropicrin from Cynara scolymus on guinea-pig ileum. Biological & pharmaceutical bulletin. 2005 May; 28(5):902-4. doi: 10.1248/bpb.28.902. [PMID: 15863902]
  • J Y Cho, J Park, E S Yoo, K U Baik, J H Jung, J Lee, M H Park. Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-alpha production in murine macrophage-like cells. Planta medica. 1998 Oct; 64(7):594-7. doi: 10.1055/s-2006-957528. [PMID: 9810262]
  • A J Hay, M Hamburger, K Hostettmann, J R Hoult. Toxic inhibition of smooth muscle contractility by plant-derived sesquiterpenes caused by their chemically reactive alpha-methylenebutyrolactone functions. British journal of pharmacology. 1994 May; 112(1):9-12. doi: 10.1111/j.1476-5381.1994.tb13020.x. [PMID: 8032668]
  • C H Cheng, B Costall, M Hamburger, K Hostettmann, R J Naylor, Y Wang, P Jenner. Toxic effects of solstitialin A 13-acetate and cynaropicrin from Centaurea solstitialis L. (Asteraceae) in cell cultures of foetal rat brain. Neuropharmacology. 1992 Mar; 31(3):271-7. doi: 10.1016/0028-3908(92)90177-q. [PMID: 1630595]