ARTEPILLIN C (BioDeep_00000763358)

   

natural product


代谢物信息卡片


2-Propenoic acid, 3-(4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)-, (E)-

化学式: C19H24O3 (300.1725354)
中文名称: 蒿素C
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C=CC(=O)O)C
InChI: InChI=1S/C19H24O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-7,10-12,22H,8-9H2,1-4H3,(H,20,21)/b10-7+

描述信息

同义名列表

10 个代谢物同义名

2-Propenoic acid, 3-(4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)-, (E)-; (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid; 3-(4-Hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)-2-propenoic acid; 3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid; (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]acrylic acid; 3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]acrylic acid; NCI60_040915; ARTEPILLIN C; 72944-19-5; NSC718732



数据库引用编号

4 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)

23 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

  • Lei Wang, Lingqin Zhou, Shuai Liu, Yaxin Liu, Jia Zhao, Yaqiong Chen, Yi Liu. Artepillin C Time-Dependently Alleviates Metabolic Syndrome in Obese Mice by Regulating CREB/CRTC2-BMAL1 Signaling. Nutrients. 2023 Mar; 15(7):. doi: 10.3390/nu15071644. [PMID: 37049484]
  • Takanori Tsuda. Anthocyanins and Curcumin: Possible Abilities of Prevention of Diabetes and Obesity via Stimulation of Glucagon-Like Peptide-1 Secretion and Induction of Beige Adipocyte Formation. Journal of nutritional science and vitaminology. 2022; 68(Supplement):S110-S112. doi: 10.3177/jnsv.68.s110. [PMID: 36436987]
  • Ashish Kaul, Raviprasad Kuthethur, Yoshiyuki Ishida, Keiji Terao, Renu Wadhwa, Sunil C Kaul. Molecular Insights into the Antistress Potentials of Brazilian Green Propolis Extract and Its Constituent Artepillin C. Molecules (Basel, Switzerland). 2021 Dec; 27(1):. doi: 10.3390/molecules27010080. [PMID: 35011307]
  • Jiangli Ding, Tomoh Matsumiya, Ryo Hayakari, Yuko Shiba, Shogo Kawaguchi, Kazuhiko Seya, Kayo Ueno, Tadaatsu Imaizumi. Daily Brazilian green propolis intake elevates blood artepillin C levels in humans. Journal of the science of food and agriculture. 2021 Aug; 101(11):4855-4861. doi: 10.1002/jsfa.11132. [PMID: 33543484]
  • Md Shahinozzaman, Bristy Basak, Rashiduzzaman Emran, Patricia Rozario, Diana N Obanda. Artepillin C: A comprehensive review of its chemistry, bioavailability, and pharmacological properties. Fitoterapia. 2020 Nov; 147(?):104775. doi: 10.1016/j.fitote.2020.104775. [PMID: 33152464]
  • Fan Wu, Xin-Mi Song, Yi-Lei Qiu, Huo-Qing Zheng, Fu-Liang Hu, Hong-Liang Li. Unique dynamic mode between Artepillin C and human serum albumin implies the characteristics of Brazilian green propolis representative bioactive component. Scientific reports. 2020 10; 10(1):17277. doi: 10.1038/s41598-020-74197-4. [PMID: 33057209]
  • Philipe Costa, Lincon Bordignon Somensi, Rita de Cássia Melo Vilhena de Andrade Fonseca da Silva, Luísa Nathalia Bolda Mariano, Thaise Boeing, Bruna Longo, Ellen Perfoll, Priscila de Souza, Lucas Fernando Sérgio Gushiken, Cláudia Helena Pellizzon, Débora Munhoz Rodrigues, Jairo Kenupp Bastos, Sérgio Faloni de Andrade, Luísa Mota da Silva. Role of the antioxidant properties in the gastroprotective and gastric healing activity promoted by Brazilian green propolis and the healing efficacy of Artepillin C. Inflammopharmacology. 2020 Aug; 28(4):1009-1025. doi: 10.1007/s10787-019-00649-7. [PMID: 31745698]
  • Mirella B Kobal, Wallance M Pazin, Maria J Bistaffa, Carlos J L Constantino, Karina A Toledo, Pedro H B Aoki. Correlating Artepillin C cytotoxic activity on HEp-2 cells with bioinspired systems of plasma membranes. Materials science & engineering. C, Materials for biological applications. 2020 Jul; 112(?):110943. doi: 10.1016/j.msec.2020.110943. [PMID: 32409089]
  • Isamara Julia Camuri, Adriano Batista da Costa, Amando Siuiti Ito, Wallance Moreira Pazin. pH and Charge Effects Behind the Interaction of Artepillin C, the Major Component of Green Propolis, With Amphiphilic Aggregates: Optical Absorption and Fluorescence Spectroscopy Studies. Photochemistry and photobiology. 2019 11; 95(6):1345-1351. doi: 10.1111/php.13128. [PMID: 31111498]
  • Wallance M Pazin, Suikinai N Dos Santos, Sonia C N Queiroz, Luis A Bagatolli, Ademilson E E Soares, Itamar S DE Melo, Amando S Ito. Bioactivity and action mechanism of green propolis against Pythium aphanidermatum. Anais da Academia Brasileira de Ciencias. 2019 Jul; 91(2):e20180598. doi: 10.1590/0001-3765201920180598. [PMID: 31271566]
  • W M Pazin, N Vilanova, I K Voets, A E E Soares, A S Ito. Effects of artepillin C on model membranes displaying liquid immiscibility. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2019 Mar; 52(3):e8281. doi: 10.1590/1414-431x20198281. [PMID: 30916221]
  • Wallance Moreira Pazin, Gilia Cristine Marques Ruiz, Osvaldo Novais de Oliveira, Carlos José Leopoldo Constantino. Interaction of Artepillin C with model membranes: Effects of pH and ionic strength. Biochimica et biophysica acta. Biomembranes. 2019 02; 1861(2):410-417. doi: 10.1016/j.bbamem.2018.11.008. [PMID: 30468729]
  • Ryosuke Munakata, Tomoya Takemura, Kanade Tatsumi, Eiko Moriyoshi, Koki Yanagihara, Akifumi Sugiyama, Hideyuki Suzuki, Hikaru Seki, Toshiya Muranaka, Noriaki Kawano, Kayo Yoshimatsu, Nobuo Kawahara, Takao Yamaura, Jérémy Grosjean, Frédéric Bourgaud, Alain Hehn, Kazufumi Yazaki. Isolation of Artemisia capillaris membrane-bound di-prenyltransferase for phenylpropanoids and redesign of artepillin C in yeast. Communications biology. 2019; 2(?):384. doi: 10.1038/s42003-019-0630-0. [PMID: 31646187]
  • Priyanshu Bhargava, Abhinav Grover, Nupur Nigam, Ashish Kaul, Motomichi Doi, Yoshiyuki Ishida, Hanzo Kakuta, Sunil C Kaul, Keiji Terao, Renu Wadhwa. Anticancer activity of the supercritical extract of Brazilian green propolis and its active component, artepillin C: Bioinformatics and experimental analyses of its mechanisms of action. International journal of oncology. 2018 Mar; 52(3):925-932. doi: 10.3892/ijo.2018.4249. [PMID: 29393408]
  • Wallance Moreira Pazin, Danilo da Silva Olivier, Neus Vilanova, Ana Paula Ramos, Ilja Karina Voets, Ademilson Espencer Egea Soares, Amando Siuiti Ito. Interaction of Artepillin C with model membranes. European biophysics journal : EBJ. 2017 May; 46(4):383-393. doi: 10.1007/s00249-016-1183-5. [PMID: 27785542]
  • R S Veiga, S De Mendonça, P B Mendes, N Paulino, M J Mimica, A A Lagareiro Netto, I S Lira, B G-C López, V Negrão, M C Marcucci. Artepillin C and phenolic compounds responsible for antimicrobial and antioxidant activity of green propolis and Baccharis dracunculifolia DC. Journal of applied microbiology. 2017 Apr; 122(4):911-920. doi: 10.1111/jam.13400. [PMID: 28066967]
  • Kei Shimoda, Naoji Kubota, Daisuke Uesugi, Hiroki Hamadab. Glycosylation of artepillin C with cultured plant cells of Phytolacca americana. Natural product communications. 2014 May; 9(5):683-5. doi: ". [PMID: 25026721]
  • Pollyanna Francielli de Oliveira, Ildercílio Mota de Souza Lima, Carla Carolina Munari, Jairo Kenupp Bastos, Ademar Alves da Silva Filho, Denise Crispim Tavares. Comparative evaluation of antiproliferative effects of Brazilian green propolis, its main source Baccharis dracunculifolia, and their major constituents artepillin C and baccharin. Planta medica. 2014 Apr; 80(6):490-2. doi: 10.1055/s-0034-1368298. [PMID: 24687736]
  • Hideki Ishikawa, Miho Goto, Nariaki Matsuura, Yoshitaka Murakami, Chiho Goto, Toshiyuki Sakai, Kazuki Kanazawa. A pilot, randomized, placebo-controlled, double-blind phase 0/biomarker study on effect of artepillin C-rich extract of Brazilian propolis in frequent colorectal adenoma polyp patients. Journal of the American College of Nutrition. 2012 Oct; 31(5):327-37. doi: 10.1080/07315724.2012.10720434. [PMID: 23529990]
  • Flávia Aparecida Resende, Carla Carolina Munari, Moacir de Azevedo Bentes Monteiro Neto, Denise Crispim Tavares, Jairo Kenupp Bastos, Ademar Alves da Silva Filho, Eliana Aparecida Varanda. Comparative Studies of the (Anti) Mutagenicity of Baccharis dracunculifolia and Artepillin C by the Bacterial Reverse Mutation Test. Molecules (Basel, Switzerland). 2012 Feb; 17(3):2335-50. doi: 10.3390/molecules17032335. [PMID: 22367028]
  • Taketoshi Hata, Shigemi Tazawa, Shozo Ohta, Mee-Ra Rhyu, Takumi Misaka, Kenji Ichihara. Artepillin C, a major ingredient of Brazilian propolis, induces a pungent taste by activating TRPA1 channels. PloS one. 2012; 7(11):e48072. doi: 10.1371/journal.pone.0048072. [PMID: 23133611]
  • Ka-Wai Cheung, Daniel Man-Yuen Sze, Wing Keung Chan, Rui-Xia Deng, Wenwei Tu, Godfrey Chi-Fung Chan. Brazilian green propolis and its constituent, Artepillin C inhibits allogeneic activated human CD4 T cells expansion and activation. Journal of ethnopharmacology. 2011 Nov; 138(2):463-71. doi: 10.1016/j.jep.2011.09.031. [PMID: 21964192]
  • Moacir de Azevedo Bentes Monteiro Neto, Ildercílio Mota de Souza Lima, Ricardo Andrade Furtado, Jairo Kenupp Bastos, Ademar Alves da Silva Filho, Denise Crispim Tavares. Antigenotoxicity of artepillin C in vivo evaluated by the micronucleus and comet assays. Journal of applied toxicology : JAT. 2011 Nov; 31(8):714-9. doi: 10.1002/jat.1614. [PMID: 21259290]
  • Sun-Sil Choi, Byung-Yoon Cha, Kagami Iida, Young-Sil Lee, Takayuki Yonezawa, Toshiaki Teruya, Kazuo Nagai, Je-Tae Woo. Artepillin C, as a PPARγ ligand, enhances adipocyte differentiation and glucose uptake in 3T3-L1 cells. Biochemical pharmacology. 2011 Apr; 81(7):925-33. doi: 10.1016/j.bcp.2011.01.002. [PMID: 21219874]
  • Yoshimi Nakajima, Kazuhiro Tsuruma, Masamitsu Shimazawa, Satoshi Mishima, Hideaki Hara. Comparison of bee products based on assays of antioxidant capacities. BMC complementary and alternative medicine. 2009 Feb; 9(?):4. doi: 10.1186/1472-6882-9-4. [PMID: 19243635]
  • Niraldo Paulino, Sheila Rago Lemos Abreu, Yoshihiro Uto, Daisuke Koyama, Hideko Nagasawa, Hitoshi Hori, Verena M Dirsch, Angelika M Vollmar, Amarilis Scremin, Walter A Bretz. Anti-inflammatory effects of a bioavailable compound, Artepillin C, in Brazilian propolis. European journal of pharmacology. 2008 Jun; 587(1-3):296-301. doi: 10.1016/j.ejphar.2008.02.067. [PMID: 18474366]
  • Mok-Ryeon Ahn, Kazuhiro Kunimasa, Toshiro Ohta, Shigenori Kumazawa, Miya Kamihira, Kazuhiko Kaji, Yoshihiro Uto, Hitoshi Hori, Hideko Nagasawa, Tsutomu Nakayama. Suppression of tumor-induced angiogenesis by Brazilian propolis: major component artepillin C inhibits in vitro tube formation and endothelial cell proliferation. Cancer letters. 2007 Jul; 252(2):235-43. doi: 10.1016/j.canlet.2006.12.039. [PMID: 17343983]
  • Yoshihiro Uto, Shutaro Ae, Daisuke Koyama, Mitsutoshi Sakakibara, Naoki Otomo, Mamoru Otsuki, Hideko Nagasawa, Kenneth L Kirk, Hitoshi Hori. Artepillin C isoprenomics: design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity. Bioorganic & medicinal chemistry. 2006 Aug; 14(16):5721-8. doi: 10.1016/j.bmc.2006.04.015. [PMID: 16697207]
  • Yoshihiro Uto, Shutaro Ae, Azusa Hotta, Junji Terao, Hideko Nagasawa, Hitoshi Hori. Artepillin C isoprenomics: design and synthesis of artepillin C analogues as antiatherogenic antioxidants. Advances in experimental medicine and biology. 2006; 578(?):113-8. doi: 10.1007/0-387-29540-2_18. [PMID: 16927679]
  • Yutaka Konishi, Yoshitaka Hitomi, Michiko Yoshida, Eiji Yoshioka. Absorption and bioavailability of artepillin C in rats after oral administration. Journal of agricultural and food chemistry. 2005 Dec; 53(26):9928-33. doi: 10.1021/jf051962y. [PMID: 16366676]
  • Kazuma Yoshizumi, Nobuo Nishioka, Tomoko Tsuji. [Xanthine oxidase inhibitory activity and hypouricemia effect of propolis in rats]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2005 Mar; 125(3):315-21. doi: 10.1248/yakushi.125.315. [PMID: 15738631]
  • Kazuo Shimizu, Hitoshi Ashida, Yukinaga Matsuura, Kazuki Kanazawa. Antioxidative bioavailability of artepillin C in Brazilian propolis. Archives of biochemistry and biophysics. 2004 Apr; 424(2):181-8. doi: 10.1016/j.abb.2004.02.021. [PMID: 15047190]
  • T Kimoto, S Koya-Miyata, K Hino, M J Micallef, T Hanaya, S Arai, M Ikeda, M Kurimoto. Pulmonary carcinogenesis induced by ferric nitrilotriacetate in mice and protection from it by Brazilian propolis and artepillin C. Virchows Archiv : an international journal of pathology. 2001 Mar; 438(3):259-70. doi: 10.1007/s004280000350. [PMID: 11315623]
  • T Kimoto, S Koya, K Hino, Y Yamamoto, Y Nomura, M J Micallef, T Hanaya, S Arai, M Ikeda, M Kurimoto. Renal carcinogenesis induced by ferric nitrilotriacetate in mice, and protection from it by Brazilian propolis and artepillin C. Pathology international. 2000 Sep; 50(9):679-89. doi: 10.1046/j.1440-1827.2000.01097.x. [PMID: 11012980]