Auraptene (BioDeep_00000407838)

Main id: BioDeep_00000318342

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-

化学式: C19H22O3 (298.15688620000003)
中文名称: 橙皮油素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=CCCC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C)C
InChI: InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

描述信息

Origin: Plant, Coumarins
Auraptene is the most abundant naturally occurring geranyloxycoumarin. Auraptene decreases the secretion of matrix metalloproteinase 2 (MMP-2) as well as key inflammatory mediators, including IL-6, IL-8, and chemokine (C-C motif) ligand-5(CCL5)[1].
Auraptene is the most abundant naturally occurring geranyloxycoumarin. Auraptene decreases the secretion of matrix metalloproteinase 2 (MMP-2) as well as key inflammatory mediators, including IL-6, IL-8, and chemokine (C-C motif) ligand-5(CCL5)[1].

同义名列表

24 个代谢物同义名

2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-; 2H-1-Benzopyran-2-one, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-; Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-; 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2-chromenone; 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one; 7-(3,7-dimethylocta-2,6-dienoxy)chromen-2-one; 7-(3,7-dimethylocta-2,6-dienoxy)-2-chromenone; 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]coumarin; 7-(3,7-dimethylocta-2,6-dienoxy)coumarin; 7-geranyloxycoumarin; UPCMLD-DP061:001; NCGC00096070-01; SPECTRUM1505176; NCGC00096070-03; NCGC00096070-04; MEGxp0_000091; STOCK1N-26363; ZINC01658901; MLS001049098; SMR000386931; ACon1_000071; NSC711511; Auraptene; 495-02-3



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)

48 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

  • Yasuyuki Akasaka, Shun Hasei, Yukino Ohata, Machi Kanna, Yusuke Nakatsu, Hideyuki Sakoda, Midori Fujishiro, Akifumi Kushiyama, Hiraku Ono, Akio Matsubara, Nobuyuki Hinata, Tomoichiro Asano, Takeshi Yamamotoya. Auraptene Enhances AMP-Activated Protein Kinase Phosphorylation and Thereby Inhibits the Proliferation, Migration and Expression of Androgen Receptors and Prostate-Specific Antigens in Prostate Cancer Cells. International journal of molecular sciences. 2023 Nov; 24(21):. doi: 10.3390/ijms242116011. [PMID: 37958994]
  • Piseth Nhoek, Sungjin Ahn, Pisey Pel, Young-Mi Kim, Jungmoo Huh, Hyun Woo Kim, Minsoo Noh, Young-Won Chin. Alkaloids and Coumarins with Adiponectin-Secretion-Promoting Activities from the Leaves of Orixa japonica. Journal of natural products. 2023 01; 86(1):138-148. doi: 10.1021/acs.jnatprod.2c00844. [PMID: 36529937]
  • Fen Wen, DeZhi Bian, XuDong Wu, RuoBing Liu, ChaoNan Wang, JianHe Gan. SU5, a new Auraptene analog with improved metabolic stability, ameliorates nonalcoholic fatty liver disease in methionine- and choline-deficient diet-fed db/db mice. Chemical biology & drug design. 2022 03; 99(3):504-511. doi: 10.1111/cbdd.14021. [PMID: 35040254]
  • Hossein Amini-Khoei, Shakiba Nasiri Boroujeni, Forough Maghsoudi, Mohammad Rahimi-Madiseh, Elham Bijad, Mohammadtaghi Moradi, Zahra Lorigooini. Possible involvement of L-arginine-nitric oxide pathway in the antidepressant activity of Auraptene in mice. Behavioral and brain functions : BBF. 2022 Feb; 18(1):4. doi: 10.1186/s12993-022-00189-1. [PMID: 35164803]
  • Ensiyeh Charmforoshan, Ehsan Karimi, Ehsan Oskoueian, Mehrdad Iranshahi. Antibacterial, Antioxidant and Melanogenesis Inhibitory Activity of Auraptene, a Coumarin from Ferula szowitsiana Root. Nutrition and cancer. 2022; 74(5):1829-1836. doi: 10.1080/01635581.2021.1962922. [PMID: 34378465]
  • Mohammad Reza Shiran, Elham Mahmoudian, Abolghasem Ajami, Seyed Mostafa Hosseini, Ayjamal Khojasteh, Mohsen Rashidi, Nazila Fathi Maroufi. Effect of Auraptene on angiogenesis in Xenograft model of breast cancer. Hormone molecular biology and clinical investigation. 2021 Dec; 43(1):7-14. doi: 10.1515/hmbci-2021-0056. [PMID: 34851565]
  • Haifa Almukadi, Basma G Eid, Rasheed A Shaik, Ashraf B Abdel-Naim, Ahmed Esmat. Auraptene nanoparticles ameliorate testosterone-induced benign prostatic hyperplasia in rats: Emphasis on antioxidant, anti-inflammatory, proapoptotic and PPARs activation effects. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Nov; 143(?):112199. doi: 10.1016/j.biopha.2021.112199. [PMID: 34649341]
  • Serena Fiorito, Francesco Epifano, Lucia Palumbo, Salvatore Genovese. A Novel Auraptene-Enriched Citrus Peels-Based Blend with Enhanced Antioxidant Activity. Plant foods for human nutrition (Dordrecht, Netherlands). 2021 Sep; 76(3):397-398. doi: 10.1007/s11130-021-00911-w. [PMID: 34255225]
  • Kobra Shirani, Mehrdad Iranshahi, Vahid Reza Askari, Zahra Gholizadeh, Armin Attaran Zadeh, Majid Zeinali, Faezeh Vahdati Hassani, Zhila Taherzadeh. Comparative evaluation of the protective effects of oral administration of auraptene and umbelliprenin against CFA-induced chronic inflammation with polyarthritis in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Jul; 139(?):111635. doi: 10.1016/j.biopha.2021.111635. [PMID: 34243601]
  • Farid Nasiri, Gholamreza Dehghan, Masoomeh Shaghaghi, Siavash Datmalchi, Mehrdad Iranshahi. Probing the interaction between 7-geranyloxycoumarin and bovine serum albumin: Spectroscopic analyzing and molecular docking study. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2021 Jun; 254(?):119664. doi: 10.1016/j.saa.2021.119664. [PMID: 33743310]
  • Yan-Gang Li, Xiao-Yun Wang, Hai-Fang Chen, Jin-Bin Yuan, Yan Meng, Wu-Liang Yang. Comparison of the chemical constituents of raw Fructus Aurantii and Fructus Aurantii stir-baked with bran, and the biological effects of auraptene. Journal of ethnopharmacology. 2021 Apr; 269(?):113721. doi: 10.1016/j.jep.2020.113721. [PMID: 33359001]
  • Mehran Arabi, Shohreh Hosseini Nasab, Zahra Lorigooini, Shakiba Nasiri Boroujeni, Seyyed Mohsen Mortazavi, Maryam Anjomshoa, Hossein Amini-Khoei. Auraptene exerts protective effects on maternal separation stress-induced changes in behavior, hippocampus, heart and serum of mice. International immunopharmacology. 2021 Apr; 93(?):107436. doi: 10.1016/j.intimp.2021.107436. [PMID: 33556667]
  • Mohammad Reza Shiran, Davar Amani, Abolghasem Ajami, Mahshad Jalalpourroodsari, Maghsoud Khalizadeh, Mohsen Rashidi. Antitumor effects of Auraptene in 4T1 tumor-bearing Balb/c mice. Hormone molecular biology and clinical investigation. 2021 Mar; 42(3):245-252. doi: 10.1515/hmbci-2020-0090. [PMID: 33675195]
  • Javad Mottaghipisheh, Norbert Kúsz, Judit Hohmann, Yu-Chi Tsai, Dezső Csupor. Isolation of secondary metabolites from the Iranian medicinal plant Eremurus persicus. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2021 Jan; 76(1-2):43-47. doi: 10.1515/znc-2020-0059. [PMID: 32681789]
  • Yoshiko Furukawa, Satoshi Okuyama, Yoshiaki Amakura, Atsushi Sawamoto, Mitsunari Nakajima, Morio Yoshimura, Michiya Igase, Naohiro Fukuda, Takahisa Tamai, Takashi Yoshida. Isolation and Characterization of Neuroprotective Components from Citrus Peel and Their Application as Functional Food. Chemical & pharmaceutical bulletin. 2021; 69(1):2-10. doi: 10.1248/cpb.c20-00265. [PMID: 33390517]
  • Tomohiro Nabekura, Tatsuya Kawasaki, Yu Kato, Kazuyoshi Kawai, Serena Fiorito, Francesco Epifano, Salvatore Genovese, Yuichi Uwai. Citrus auraptene induces drug efflux transporter P-glycoprotein expression in human intestinal cells. Food & function. 2020 Jun; 11(6):5017-5023. doi: 10.1039/d0fo00315h. [PMID: 32530447]
  • Salvatore Genovese, Francesco Epifano, Francesca Preziuso, Azzurra Stefanucci, Luca Scotti, Tonino Bucciarelli, Pietro di Profio, Valentino Canale, Serena Fiorito. A novel and efficient subcritical butane extraction method and UHPLC analysis of oxyprenylated phenylpropanoids from grapefruits peels. Journal of pharmaceutical and biomedical analysis. 2020 May; 184(?):113185. doi: 10.1016/j.jpba.2020.113185. [PMID: 32113120]
  • Serena Fiorito, Salvatore Genovese, Lucia Palumbo, Luca Scotti, Michele Ciulla, Pietro di Profio, Francesco Epifano. Umbelliprenin as a novel component of the phytochemical pool from Artemisia spp. Journal of pharmaceutical and biomedical analysis. 2020 May; 184(?):113205. doi: 10.1016/j.jpba.2020.113205. [PMID: 32113116]
  • Junqiao Wang, Ting Fu, Renchao Dong, Changyuan Wang, Kexin Liu, Huijun Sun, Xiaokui Huo, Xiaodong Ma, Xiaobo Yang, Qiang Meng. Hepatoprotection of auraptene from the peels of citrus fruits against 17α-ethinylestradiol-induced cholestasis in mice by activating farnesoid X receptor. Food & function. 2019 Jul; 10(7):3839-3850. doi: 10.1039/c9fo00318e. [PMID: 31210195]
  • Serena Fiorito, Federica Ianni, Francesca Preziuso, Francesco Epifano, Luca Scotti, Tonino Bucciarelli, Salvatore Genovese. UHPLC-UV/Vis Quantitative Analysis of Hydroxylated and O-prenylated Coumarins in Pomegranate Seed Extracts. Molecules (Basel, Switzerland). 2019 May; 24(10):. doi: 10.3390/molecules24101963. [PMID: 31121819]
  • Basem M Abdallah, Enas M Ali, Hany Elsawy, Gehan M Badr, Ashraf M Abdel-Moneim, Abdullah M Alzahrani. The Coumarin Derivative 5'-Hydroxy Auraptene Suppresses Osteoclast Differentiation via Inhibiting MAPK and c-Fos/NFATc1 Pathways. BioMed research international. 2019; 2019(?):9395146. doi: 10.1155/2019/9395146. [PMID: 31976330]
  • Satoshi Okuyama, Mako Katoh, Tomoko Kanzaki, Yoshimi Kotani, Yoshiaki Amakura, Morio Yoshimura, Naohiro Fukuda, Takahisa Tamai, Atsushi Sawamoto, Mitsunari Nakajima, Yoshiko Furukawa. Auraptene/Naringin-Rich Fruit Juice of Citrus kawachiensis (Kawachi Bankan) Prevents Ischemia-Induced Neuronal Cell Death in Mouse Brain through Anti-Inflammatory Responses. Journal of nutritional science and vitaminology. 2019; 65(1):66-71. doi: 10.3177/jnsv.65.66. [PMID: 30814414]
  • Guangzhi Li, Junchi Wang, Xiaojin Li, Jianguo Xu, Zhao Zhang, Jianyong Si. A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803. Archives of pharmacal research. 2018 Jun; 41(6):646-654. doi: 10.1007/s12272-018-1028-0. [PMID: 29619675]
  • Luca Scotti, Salvatore Genovese, Tonino Bucciarelli, Filippo Martini, Francesco Epifano, Serena Fiorito, Francesca Preziuso, Vito Alessandro Taddeo. Analysis of biologically active oxyprenylated phenylpropanoids in Tea tree oil using selective solid-phase extraction with UHPLC-PDA detection. Journal of pharmaceutical and biomedical analysis. 2018 May; 154(?):174-179. doi: 10.1016/j.jpba.2018.03.004. [PMID: 29549856]
  • Vincenzo Ferrone, Salvatore Genovese, Maura Carlucci, Matteo Tiecco, Raimondo Germani, Francesca Preziuso, Francesco Epifano, Giuseppe Carlucci, Vito Alessandro Taddeo. A green deep eutectic solvent dispersive liquid-liquid micro-extraction (DES-DLLME) for the UHPLC-PDA determination of oxyprenylated phenylpropanoids in olive, soy, peanuts, corn, and sunflower oil. Food chemistry. 2018 Apr; 245(?):578-585. doi: 10.1016/j.foodchem.2017.10.135. [PMID: 29287412]
  • Sara Daneshmand, Mahmoud Reza Jaafari, Jebrail Movaffagh, Bizhan Malaekeh-Nikouei, Mehrdad Iranshahi, Atieh Seyedian Moghaddam, Zahra Tayarani Najaran, Shiva Golmohammadzadeh. Preparation, characterization, and optimization of auraptene-loaded solid lipid nanoparticles as a natural anti-inflammatory agent: In vivo and in vitro evaluations. Colloids and surfaces. B, Biointerfaces. 2018 Apr; 164(?):332-339. doi: 10.1016/j.colsurfb.2018.01.054. [PMID: 29413613]
  • Salvatore Genovese, Vito Alessandro Taddeo, Francesco Epifano, Serena Fiorito, Cécile Bize, Arnaud Rives, Philippe de Medina. Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species. Journal of natural products. 2017 09; 80(9):2424-2431. doi: 10.1021/acs.jnatprod.7b00175. [PMID: 28853883]
  • Salvatore Genovese, Hitoshi Ashida, Yoko Yamashita, Tomoya Nakgano, Masaki Ikeda, Shirasaya Daishi, Francesco Epifano, Vito Alessandro Taddeo, Serena Fiorito. The interaction of auraptene and other oxyprenylated phenylpropanoids with glucose transporter type 4. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Aug; 32(?):74-79. doi: 10.1016/j.phymed.2017.06.005. [PMID: 28732810]
  • Tatyana M Khomenko, Vladimir V Zarubaev, Iana R Orshanskaya, Renata A Kadyrova, Victoria A Sannikova, Dina V Korchagina, Konstantin P Volcho, Nariman F Salakhutdinov. Anti-influenza activity of monoterpene-containing substituted coumarins. Bioorganic & medicinal chemistry letters. 2017 07; 27(13):2920-2925. doi: 10.1016/j.bmcl.2017.04.091. [PMID: 28501512]
  • Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorganic & medicinal chemistry letters. 2016 10; 26(19):4714-4719. doi: 10.1016/j.bmcl.2016.08.044. [PMID: 27575476]
  • X D Ye, H Ouyang, L Y Zhong, T E Li, X Y Rao, Y L Feng, W L Yang. Rapid and sensitive LC-MS/MS method for the determination of auraptene in rat plasma and its application in a pharmacokinetic and bioavailability study in rats. Genetics and molecular research : GMR. 2016 Jun; 15(2):. doi: 10.4238/gmr.15028786. [PMID: 27420975]
  • Mustafa Ghanbarabadi, Mehrdad Iranshahi, Sakineh Amoueian, Soghra Mehri, Vahideh Sadat Motamedshariaty, Seyed Ahmad Mohajeri. Neuroprotective and memory enhancing effects of auraptene in a rat model of vascular dementia: Experimental study and histopathological evaluation. Neuroscience letters. 2016 06; 623(?):13-21. doi: 10.1016/j.neulet.2016.04.047. [PMID: 27130820]
  • Phi-Hung Nguyen, Bing Tian Zhao, Okhwa Kim, Jeong Hyung Lee, Jae Sue Choi, Byung Sun Min, Mi Hee Woo. Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium with α-glucosidase inhibitory activity. Journal of natural medicines. 2016 Apr; 70(2):276-81. doi: 10.1007/s11418-015-0957-x. [PMID: 26753624]
  • Damian H Adams, Qingyao Shou, Hans Wohlmuth, Allison J Cowin. Native Australian plant extracts differentially induce Collagen I and Collagen III in vitro and could be important targets for the development of new wound healing therapies. Fitoterapia. 2016 Mar; 109(?):45-51. doi: 10.1016/j.fitote.2015.12.010. [PMID: 26705840]
  • Giuseppe Derosa, Pamela Maffioli, Amirhossein Sahebkar. Auraptene and Its Role in Chronic Diseases. Advances in experimental medicine and biology. 2016; 929(?):399-407. doi: 10.1007/978-3-319-41342-6_19. [PMID: 27771936]
  • Yunseon Jang, Jeongsu Han, Soo Jeong Kim, Jungim Kim, Min Joung Lee, Soyeon Jeong, Min Jeong Ryu, Kang-Sik Seo, Song-Yi Choi, Minho Shong, Kyu Lim, Jun Young Heo, Gi Ryang Kweon. Suppression of mitochondrial respiration with auraptene inhibits the progression of renal cell carcinoma: involvement of HIF-1α degradation. Oncotarget. 2015 Nov; 6(35):38127-38. doi: 10.18632/oncotarget.5511. [PMID: 26474388]
  • Salvatore Genovese, Serena Fiorito, Francesco Epifano, Vito Alessandro Taddeo. A Novel Class of Emerging Anticancer Compounds: Oxyprenylated Secondary Metabolites from Plants and Fungi. Current medicinal chemistry. 2015; 22(30):3426-33. doi: 10.2174/0929867322666150716114758. [PMID: 26180000]
  • Abolfazl Shakeri, Milad Iranshahy, Mehrdad Iranshahi. Biological properties and molecular targets of umbelliprenin--a mini-review. Journal of Asian natural products research. 2014; 16(8):884-9. doi: 10.1080/10286020.2014.917630. [PMID: 24852499]
  • Huiqing Yan, Zhaocheng Ma, Shu'ang Peng, Xiuxin Deng. Anti-inflammatory effect of auraptene extracted from trifoliate orange (Poncirus trifoliate) on LPS-stimulated RAW 264.7 cells. Inflammation. 2013 Dec; 36(6):1525-32. doi: 10.1007/s10753-013-9695-y. [PMID: 23872723]
  • Vu Dang La, Lei Zhao, Francesco Epifano, Salvatore Genovese, Daniel Grenier. Anti-inflammatory and wound healing potential of citrus auraptene. Journal of medicinal food. 2013 Oct; 16(10):961-4. doi: 10.1089/jmf.2013.0029. [PMID: 24070132]
  • Hamid-Reza Adhami, Uta Scherer, Hanspeter Kaehlig, Timm Hettich, Götz Schlotterbeck, Eike Reich, Liselotte Krenn. Combination of bioautography with HPTLC-MS/NMR: a fast identification of acetylcholinesterase inhibitors from galbanum(†). Phytochemical analysis : PCA. 2013 Jul; 24(4):395-400. doi: 10.1002/pca.2422. [PMID: 23427054]
  • Shan Lin, Shizuka Hirai, Tsuyoshi Goto, Tomoya Sakamoto, Nobuyuki Takahashi, Masamichi Yano, Takao Sasaki, Rina Yu, Teruo Kawada. Auraptene suppresses inflammatory responses in activated RAW264 macrophages by inhibiting p38 mitogen-activated protein kinase activation. Molecular nutrition & food research. 2013 Jul; 57(7):1135-44. doi: 10.1002/mnfr.201200611. [PMID: 23495198]
  • Pravin O Patil, Sanjay B Bari, Sandip D Firke, Prashant K Deshmukh, Shailesh T Donda, Dilip A Patil. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease. Bioorganic & medicinal chemistry. 2013 May; 21(9):2434-50. doi: 10.1016/j.bmc.2013.02.017. [PMID: 23517722]
  • Jun Li, Fakhri Mahdi, Lin Du, Mika B Jekabsons, Yu-Dong Zhou, Dale G Nagle. Semisynthetic studies identify mitochondria poisons from botanical dietary supplements--geranyloxycoumarins from Aegle marmelos. Bioorganic & medicinal chemistry. 2013 Apr; 21(7):1795-803. doi: 10.1016/j.bmc.2013.01.048. [PMID: 23434131]
  • Laura Mercolini, Roberto Mandrioli, Anna Ferranti, Vittorio Sorella, Michele Protti, Francesco Epifano, Massimo Curini, Maria Augusta Raggi. Quantitative evaluation of auraptene and umbelliferone, chemopreventive coumarins in citrus fruits, by HPLC-UV-FL-MS. Journal of agricultural and food chemistry. 2013 Feb; 61(8):1694-701. doi: 10.1021/jf303060b. [PMID: 23083450]
  • Hirotaka Sekiguchi, Fumiyo Takabayashi, Kazuhiro Irie, Akira Murakami. Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice. Journal of medicinal food. 2012 Jul; 15(7):658-63. doi: 10.1089/jmf.2011.1844. [PMID: 22471969]
  • Annie Marquis, Salvatore Genovese, Francesco Epifano, Daniel Grenier. The plant coumarins auraptene and lacinartin as potential multifunctional therapeutic agents for treating periodontal disease. BMC complementary and alternative medicine. 2012 Jun; 12(?):80. doi: 10.1186/1472-6882-12-80. [PMID: 22742512]
  • Francesco Epifano, Salvatore Genovese, E James Squires, Matthew A Gray. Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist. Bioorganic & medicinal chemistry letters. 2012 May; 22(9):3130-5. doi: 10.1016/j.bmcl.2012.03.057. [PMID: 22472691]
  • Nobuyuki Takahashi, Mari Senda, Shan Lin, Tsuyoshi Goto, Masamichi Yano, Takao Sasaki, Shigeru Murakami, Teruo Kawada. Auraptene regulates gene expression involved in lipid metabolism through PPARα activation in diabetic obese mice. Molecular nutrition & food research. 2011 Dec; 55(12):1791-7. doi: 10.1002/mnfr.201100401. [PMID: 22038981]
  • Yan-Gang Li, Hai-Fang Chen, Ming-Zhu Tu, Pu-Zhao Zhang, Xiao-Yun Wang, Jin-Bin Yuan, Wu-Liang Yang. Identification, synthesis and quantification of process-related impurities in auraptene. Journal of pharmaceutical and biomedical analysis. 2011 Sep; 56(2):191-9. doi: 10.1016/j.jpba.2011.05.011. [PMID: 21705169]
  • Kunishige Onuma, Yuka Suenaga, Ryuta Sakaki, Satoshi Yoshitome, Yu Sato, Satomi Ogawara, Saori Suzuki, Yasuhiro Kuramitsu, Hidekatsu Yokoyama, Akira Murakami, Junichi Hamada, Garth L Nicolson, Masanobu Kobayashi, Junichi Fujii, Futoshi Okada. Development of a quantitative bioassay to assess preventive compounds against inflammation-based carcinogenesis. Nitric oxide : biology and chemistry. 2011 Aug; 25(2):183-94. doi: 10.1016/j.niox.2011.02.003. [PMID: 21345376]
  • Su Yang Jeong, Do Youn Jun, Young Ho Kim, Byung-Sun Min, Bo Kyung Min, Mi Hee Woo. Monoterpenoids from the aerial parts of Aruncus dioicus var. kamtschaticus and their antioxidant and cytotoxic activities. Bioorganic & medicinal chemistry letters. 2011 Jun; 21(11):3252-6. doi: 10.1016/j.bmcl.2011.04.043. [PMID: 21546250]
  • Eric M Sciullo, Christoph F Vogel, Dalei Wu, Akira Murakami, Hajime Ohigashi, Fumio Matsumura. Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages. Archives of toxicology. 2010 Dec; 84(12):957-66. doi: 10.1007/s00204-010-0592-y. [PMID: 20865247]
  • Koji Nagao, Naomi Yamano, Bungo Shirouchi, Nao Inoue, Shigeru Murakami, Takao Sasaki, Teruyoshi Yanagita. Effects of citrus auraptene (7-geranyloxycoumarin) on hepatic lipid metabolism in vitro and in vivo. Journal of agricultural and food chemistry. 2010 Aug; 58(16):9028-32. doi: 10.1021/jf1020329. [PMID: 20681532]
  • Heather E Kleiner-Hancock, Runhua Shi, Angela Remeika, Delira Robbins, Misty Prince, Jennifer N Gill, Zanobia Syed, Patrick Adegboyega, J Michael Mathis, John L Clifford. Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts. BMC cancer. 2010 Jul; 10(?):394. doi: 10.1186/1471-2407-10-394. [PMID: 20659317]
  • Tao Feng, Rui-Rui Wang, Xiang-Hai Cai, Yong-Tang Zheng, Xiao-Dong Luo. Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata. Chemical & pharmaceutical bulletin. 2010 Jul; 58(7):971-5. doi: 10.1248/cpb.58.971. [PMID: 20606349]
  • Hirotaka Sekiguchi, Kazuhiro Irie, Akira Murakami. Suppression of CD74 expression and Helicobacter pylori adhesion by auraptene targeting serum starvation-activated ERK1/2 in NCI-N87 gastric carcinoma cells. Bioscience, biotechnology, and biochemistry. 2010; 74(5):1018-24. doi: 10.1271/bbb.90910. [PMID: 20460732]
  • Thaïs B César, John A Manthey, Kyung Myung. Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4. Journal of natural products. 2009 Sep; 72(9):1702-4. doi: 10.1021/np900266m. [PMID: 19689106]
  • Toshifumi Hirata, Misato Fujii, Kazuhiro Akita, Noriyuki Yanaka, Kaori Ogawa, Masanori Kuroyanagi, Daiki Hongo. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & medicinal chemistry. 2009 Jan; 17(1):25-8. doi: 10.1016/j.bmc.2008.11.039. [PMID: 19054677]
  • Kayo Kuroyanagi, Min-Sook Kang, Tsuyoshi Goto, Shizuka Hirai, Kana Ohyama, Tatsuya Kusudo, Rina Yu, Masamichi Yano, Takao Sasaki, Nobuyuki Takahashi, Teruo Kawada. Citrus auraptene acts as an agonist for PPARs and enhances adiponectin production and MCP-1 reduction in 3T3-L1 adipocytes. Biochemical and biophysical research communications. 2008 Feb; 366(1):219-25. doi: 10.1016/j.bbrc.2007.11.119. [PMID: 18060855]
  • Nobuyuki Takahashi, Min-Sook Kang, Kayo Kuroyanagi, Tsuyoshi Goto, Shizuka Hirai, Kana Ohyama, Joo-Young Lee, Rina Yu, Masamichi Yano, Takao Sasaki, Shigeru Murakami, Teruo Kawada. Auraptene, a citrus fruit compound, regulates gene expression as a PPARalpha agonist in HepG2 hepatocytes. BioFactors (Oxford, England). 2008; 33(1):25-32. doi: 10.1002/biof.5520330103. [PMID: 19276534]
  • Takuji Tanaka, Yumiko Yasui, Rikako Ishigamori-Suzuki, Takeru Oyama. Citrus compounds inhibit inflammation- and obesity-related colon carcinogenesis in mice. Nutrition and cancer. 2008; 60 Suppl 1(?):70-80. doi: 10.1080/01635580802381253. [PMID: 19003583]
  • Chantal Barthomeuf, Suzanne Lim, Mehrdad Iranshahi, Philippe Chollet. Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Jan; 15(1-2):103-11. doi: 10.1016/j.phymed.2007.04.001. [PMID: 17689942]
  • Wataru Kuki, Keisuke Hosotani, Hajime Ohigashi, Akira Murakami. Metabolism and absorption of auraptene (7-geranyloxylcoumarin) in male SD rats: comparison with 7-ethoxycoumarin. Nutrition and cancer. 2008; 60(3):368-72. doi: 10.1080/01635580701745327. [PMID: 18444171]
  • Do Y Jun, Jun S Kim, Hae S Park, Cho R Han, Zhe Fang, Mi H Woo, In K Rhee, Young H Kim. Apoptogenic activity of auraptene of Zanthoxylum schinifolium toward human acute leukemia Jurkat T cells is associated with ER stress-mediated caspase-8 activation that stimulates mitochondria-dependent or -independent caspase cascade. Carcinogenesis. 2007 Jun; 28(6):1303-13. doi: 10.1093/carcin/bgm028. [PMID: 17301064]
  • MingXi Tang, Kumiko Ogawa, Makoto Asamoto, Naomi Hokaiwado, Azman Seeni, Shugo Suzuki, Satoru Takahashi, Takuji Tanaka, Kazuhito Ichikawa, Tomoyuki Shirai. Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells. Cancer science. 2007 Apr; 98(4):471-7. doi: 10.1111/j.1349-7006.2007.00417.x. [PMID: 17284254]
  • H B Napolitano, M Silva, J Ellena, B D G Rodrigues, A L C Almeida, P C Vieira, G Oliva, O H Thiemann. Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2004 Dec; 37(12):1847-52. doi: 10.1590/s0100-879x2004001200010. [PMID: 15558191]
  • H Wangensteen, E Molden, H Christensen, K E Malterud. Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel. European journal of clinical pharmacology. 2003 Feb; 58(10):663-8. doi: 10.1007/s00228-002-0537-3. [PMID: 12610742]
  • Yasuo Takahashi, Nobuya Inaba, Shigeru Kuwahara, Wataru Kuki, Keiko Yamane, Akira Murakami. Rapid and convenient method for preparing aurapten-enriched product from hassaku peel oil: implications for cancer-preventive food additives. Journal of agricultural and food chemistry. 2002 May; 50(11):3193-6. doi: 10.1021/jf011628b. [PMID: 12009985]
  • M Miyazawa, H Tougo, M Ishihara. Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi. Natural product letters. 2001; 15(3):205-10. doi: 10.1080/10575630108041281. [PMID: 11858553]
  • M Kitano, H Wanibuchi, H Kikuzaki, N Nakatani, S Imaoka, Y Funae, S Hayashi, S Fukushima. Chemopreventive effects of coumaperine from pepper on the initiation stage of chemical hepatocarcinogenesis in the rat. Japanese journal of cancer research : Gann. 2000 Jul; 91(7):674-80. doi: 10.1111/j.1349-7006.2000.tb00998.x. [PMID: 10920273]
  • T Tanaka, K Kawabata, M Kakumoto, A Hara, A Murakami, W Kuki, Y Takahashi, H Yonei, M Maeda, T Ota, S Odashima, T Yamane, K Koshimizu, H Ohigashi. Citrus auraptene exerts dose-dependent chemopreventive activity in rat large bowel tumorigenesis: the inhibition correlates with suppression of cell proliferation and lipid peroxidation and with induction of phase II drug-metabolizing enzymes. Cancer research. 1998 Jun; 58(12):2550-6. doi: ". [PMID: 9635577]
  • T KARIYONE, T MATSUNO. Studies on the constituents of orange oil. I. On the structure of auraptene. Pharmaceutical bulletin. 1953 Jun; 1(2):119-22. doi: 10.1248/cpb1953.1.119. [PMID: 13155117]