l-Arctigenin (BioDeep_00000180333)

   

human metabolite blood metabolite


代谢物信息卡片


4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

化学式: C21H24O6 (372.1572804)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
InChI: InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3

描述信息

同义名列表

3 个代谢物同义名

4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; l-Arctigenin; Arctigenin



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)

15 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

  • Binfeng Cheng, Yuanyuan Hou, Liqiang Wang, Linyi Dong, Jiamin Peng, Gang Bai. Dual-bioactivity-based liquid chromatography-coupled quadrupole time-of-flight mass spectrometry for NF-κB inhibitors and β2AR agonists identification in Chinese Medicinal Preparation Qingfei Xiaoyan Wan. Analytical and bioanalytical chemistry. 2012 Nov; 404(8):2445-52. doi: 10.1007/s00216-012-6332-9. [PMID: 22965529]
  • Siti Susanti, Hironori Iwasaki, Yukiyoshi Itokazu, Mariko Nago, Naoyuki Taira, Seikoh Saitoh, Hirosuke Oku. Tumor specific cytotoxicity of arctigenin isolated from herbal plant Arctium lappa L. Journal of natural medicines. 2012 Oct; 66(4):614-21. doi: 10.1007/s11418-012-0628-0. [PMID: 22350142]
  • C Miele, F Beguinot. New expectations from the well-known medicinal properties of Arctium lappa. Diabetologia. 2012 May; 55(5):1244-6. doi: 10.1007/s00125-012-2503-7. [PMID: 22358500]
  • S-L Huang, R-T Yu, J Gong, Y Feng, Y-L Dai, F Hu, Y-H Hu, Y-D Tao, Y Leng. Arctigenin, a natural compound, activates AMP-activated protein kinase via inhibition of mitochondria complex I and ameliorates metabolic disorders in ob/ob mice. Diabetologia. 2012 May; 55(5):1469-81. doi: 10.1007/s00125-011-2366-3. [PMID: 22095235]
  • Fan He, He Fan, De-Qiang Dou, Dou De-Qiang, Yu Sun, Sun Yu, Lin Zhu, Zhu Lin, Hong-Bin Xiao, Xiao Hong-Bin, Ting-Guo Kang, Kang Ting-Guo. Plasma pharmacokinetics and tissue distribution of arctiin and its main metabolite in rats by HPLC-UV and LC-MS. Planta medica. 2012 May; 78(8):800-6. doi: 10.1055/s-0031-1298433. [PMID: 22499560]
  • Li-Ying Zhang, Yi-Shun Yang, Tong Zhang, Yue Ding, Zhen-Zhen Cai, Jian-Sheng Tao. [Research on the preparative method of Arctigenin]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Mar; 35(3):467-70. doi: ". [PMID: 22876688]
  • Tao Fan, Wei Long Jiang, Jian Zhu, Yu Feng Zhang. Arctigenin protects focal cerebral ischemia-reperfusion rats through inhibiting neuroinflammation. Biological & pharmaceutical bulletin. 2012; 35(11):2004-9. doi: 10.1248/bpb.b12-00463. [PMID: 22972486]
  • Chen Gui-Rong, Cai Li-Ping, Dou De-Qiang, Kang Ting-Guo, Li Hong-Fu, Li Fu-Rui, Jiang Ning. Synthesis of (-)-arctigenin derivatives and their anticancer activity. Natural product research. 2012; 26(2):177-81. doi: 10.1080/14786419.2010.541874. [PMID: 21867457]
  • Il-Hoon Jung, Jeong Hoon Lee, Yang-Jin Hyun, Dong-Hyun Kim. Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing β-D-glucosidase from Bifidobacterium longum H-1. Biological & pharmaceutical bulletin. 2012; 35(4):573-81. doi: 10.1248/bpb.35.573. [PMID: 22466563]
  • In-Ah Lee, Eun-Ha Joh, Dong-Hyun Kim. Arctigenin isolated from the seeds of Arctium lappa ameliorates memory deficits in mice. Planta medica. 2011 Sep; 77(13):1525-7. doi: 10.1055/s-0030-1270746. [PMID: 21308615]
  • Kyungsu Kang, Hee Ju Lee, Ji-Hye Yoo, Eun Hye Jho, Chul Young Kim, Minkyun Kim, Chu Won Nho. Cell and nuclear enlargement of SW480 cells induced by a plant lignan, arctigenin: evaluation of cellular DNA content using fluorescence microscopy and flow cytometry. DNA and cell biology. 2011 Aug; 30(8):623-9. doi: 10.1089/dna.2010.1199. [PMID: 21663531]
  • Cheryl Lans, Nancy Turner. Organic parasite control for poultry and rabbits in British Columbia, Canada. Journal of ethnobiology and ethnomedicine. 2011 Jul; 7(?):21. doi: 10.1186/1746-4269-7-21. [PMID: 21756341]
  • Fabricia S Predes, Ana L T G Ruiz, João E Carvalho, Mary A Foglio, Heidi Dolder. Antioxidative and in vitro antiproliferative activity of Arctium lappa root extracts. BMC complementary and alternative medicine. 2011 Mar; 11(?):25. doi: 10.1186/1472-6882-11-25. [PMID: 21429215]
  • Jin Hee Lee, Ji Yun Lee, Tae Doo Kim, Chang Jong Kim. Antiasthmatic action of dibenzylbutyrolactone lignans from fruits of Forsythia viridissima on asthmatic responses to ovalbumin challenge in conscious guinea-pigs. Phytotherapy research : PTR. 2011 Mar; 25(3):387-95. doi: 10.1002/ptr.3273. [PMID: 20734328]
  • Yuri Kim, Joseph A Hollenbaugh, Dong-Hyun Kim, Baek Kim. Novel PI3K/Akt inhibitors screened by the cytoprotective function of human immunodeficiency virus type 1 Tat. PloS one. 2011; 6(7):e21781. doi: 10.1371/journal.pone.0021781. [PMID: 21765914]
  • Xuan Tang, Jingjing Zhuang, Jing Chen, Liang Yu, Lihong Hu, Hualiang Jiang, Xu Shen. Arctigenin efficiently enhanced sedentary mice treadmill endurance. PloS one. 2011; 6(8):e24224. doi: 10.1371/journal.pone.0024224. [PMID: 21887385]
  • Jin-Hwa Kim, Jun-Tae Bae, Min-Hyeon Song, Geun-Su Lee, Soo-Young Choe, Hyeong-Bae Pyo. Biological activities of Fructus arctii fermented with the basidiomycete Grifola frondosa. Archives of pharmacal research. 2010 Dec; 33(12):1943-51. doi: 10.1007/s12272-010-1209-y. [PMID: 21191759]
  • Bence Csapi, Zsuzsanna Hajdú, István Zupkó, Agnes Berényi, Peter Forgo, Pál Szabó, Judit Hohmann. Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria. Phytotherapy research : PTR. 2010 Nov; 24(11):1664-9. doi: 10.1002/ptr.3187. [PMID: 21031625]
  • Zhenggang Yue, Jiachen Zi, Chenggen Zhu, Sheng Lin, Yongchun Yang, Jiangong Shi. [Constituents of Gymnadenia conopsea]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Nov; 35(21):2852-61. doi: . [PMID: 21322946]
  • I Boldizsár, M Kraszni, F Tóth, B Noszál, I Molnár-Perl. Complementary fragmentation pattern analysis by gas chromatography-mass spectrometry and liquid chromatography tandem mass spectrometry confirmed the precious lignan content of Cirsium weeds. Journal of chromatography. A. 2010 Oct; 1217(40):6281-9. doi: 10.1016/j.chroma.2010.08.018. [PMID: 20813375]
  • Hiromi Tohno, Chikafumi Horii, Takafumi Fuse, Akira Okonogi, Satoshi Yomoda. Evaluation of estrogen receptor Beta binding of pruni cortex and its constituents. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2010 07; 130(7):989-97. doi: 10.1248/yakushi.130.989. [PMID: 20606380]
  • I Boldizsár, Zs Füzfai, F Tóth, E Sedlák, L Borsodi, I Molnár-Perl. Mass fragmentation study of the trimethylsilyl derivatives of arctiin, matairesinoside, arctigenin, phylligenin, matairesinol, pinoresinol and methylarctigenin: their gas and liquid chromatographic analysis in plant extracts. Journal of chromatography. A. 2010 Mar; 1217(10):1674-82. doi: 10.1016/j.chroma.2010.01.019. [PMID: 20137791]
  • Ji Yun Lee, Bong Jae Cho, Tae Wook Park, Byoung Eun Park, Soo Jung Kim, Sang Soo Sim, Chang Jong Kim. Dibenzylbutyrolactone lignans from Forsythia koreana fruits attenuate lipopolysaccharide-induced inducible nitric oxide synthetase and cyclooxygenase-2 expressions through activation of nuclear factor-κb and mitogen-activated protein kinase in RAW264.7 cells. Biological & pharmaceutical bulletin. 2010; 33(11):1847-53. doi: 10.1248/bpb.33.1847. [PMID: 21048310]
  • Bikash Sahay, Rebeca L Patsey, Christian H Eggers, Juan C Salazar, Justin D Radolf, Timothy J Sellati. CD14 signaling restrains chronic inflammation through induction of p38-MAPK/SOCS-dependent tolerance. PLoS pathogens. 2009 Dec; 5(12):e1000687. doi: 10.1371/journal.ppat.1000687. [PMID: 20011115]
  • Eun-Jin Yang, Eun-Young Yim, Gwanpil Song, Gi-Ok Kim, Chang-Gu Hyun. Inhibition of nitric oxide production in lipopolysaccharide-activated RAW 264.7 macrophages by Jeju plant extracts. Interdisciplinary toxicology. 2009 Dec; 2(4):245-9. doi: 10.2478/v10102-009-0022-2. [PMID: 21217861]
  • Gao-xue Wang, Jing Han, Ting-ting Feng, Fu-yuan Li, Bin Zhu. Bioassay-guided isolation and identification of active compounds from Fructus Arctii against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus). Parasitology research. 2009 Dec; 106(1):247-55. doi: 10.1007/s00436-009-1659-7. [PMID: 19859737]
  • Feng Zhao, Lu Wang, Ke Liu. In vitro anti-inflammatory effects of arctigenin, a lignan from Arctium lappa L., through inhibition on iNOS pathway. Journal of ethnopharmacology. 2009 Apr; 122(3):457-62. doi: 10.1016/j.jep.2009.01.038. [PMID: 19429312]
  • Rong-Jyh Lin, Chung-Yi Chen, Wen-Li Lo. Cytotoxic activity of Ipomoea cairica. Natural product research. 2008 Jun; 22(9):747-53. doi: 10.1080/14786410701628739. [PMID: 18569716]
  • Vivek Swarup, Joydeep Ghosh, Manoj Kumar Mishra, Anirban Basu. Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan. The Journal of antimicrobial chemotherapy. 2008 Mar; 61(3):679-88. doi: 10.1093/jac/dkm503. [PMID: 18230688]
  • 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]
  • Wei-nan Zhang, Yu Xiang, Yuan-yuan Jiang, Zhuo-ming Li, Zhi-hua Zhang, Hua Zhang, Li Li. [A comparative research on quality of Vitmin C Yinqiao tablets from different manufacturers]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Nov; 32(22):2364-7. doi: . [PMID: 18257259]
  • Takeshi Toyoda, Tetsuya Tsukamoto, Tsutomu Mizoshita, Sansei Nishibe, Takeshi Deyama, Yoshiharu Takenaka, Naoki Hirano, Harunari Tanaka, Shinji Takasu, Hisayo Ban, Toshiko Kumagai, Ken-Ichi Inada, Hirotoshi Utsunomiya, Masae Tatematsu. Inhibitory effect of nordihydroguaiaretic acid, a plant lignan, on Helicobacter pylori-associated gastric carcinogenesis in Mongolian gerbils. Cancer science. 2007 Nov; 98(11):1689-95. doi: 10.1111/j.1349-7006.2007.00599.x. [PMID: 17894552]
  • Jong-Sik Jin, Yu-Feng Zhao, Norio Nakamura, Teruaki Akao, Nobuko Kakiuchi, Masao Hattori. Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone. Biological & pharmaceutical bulletin. 2007 May; 30(5):904-11. doi: 10.1248/bpb.30.904. [PMID: 17473433]
  • Johanna W Lampe, Charlotte Atkinson, Meredith A J Hullar. Assessing exposure to lignans and their metabolites in humans. Journal of AOAC International. 2006 Jul; 89(4):1174-81. doi: . [PMID: 16915861]
  • Chul Young Kim, Mi-Jeong Ahn, Jinwoong Kim. A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography. Journal of separation science. 2006 Mar; 29(5):656-9. doi: 10.1002/jssc.200500316. [PMID: 16605084]
  • Suresh Awale, Jie Lu, Surya K Kalauni, Yukiko Kurashima, Yasuhiro Tezuka, Shigetoshi Kadota, Hiroyasu Esumi. Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Cancer research. 2006 Feb; 66(3):1751-7. doi: 10.1158/0008-5472.can-05-3143. [PMID: 16452235]
  • Zifeng Yang, Ni Liu, Bisong Huang, Yanfang Wang, Yingjie Hu, Yutong Zhu. [Effect of anti-influenza virus of Arctigenin in vivo]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2005 Nov; 28(11):1012-4. doi: ". [PMID: 16514891]
  • Yi-min Zheng, Shao-xi Cai, Xiu-ying Xu, Shan-quan Fu. [Dyuamical studies on metabolic chemistry of lignans from seeds of Arctium lappa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Aug; 30(16):1287-9. doi: NULL. [PMID: 16245912]
  • Shiming Liu, Kaoshan Chen, Willibald Schliemann, Dieter Strack. Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS. Phytochemical analysis : PCA. 2005 Mar; 16(2):86-9. doi: 10.1002/pca.816. [PMID: 15881114]
  • B Hausott, H Greger, B Marian. Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells. Journal of cancer research and clinical oncology. 2003 Oct; 129(10):569-76. doi: 10.1007/s00432-003-0461-7. [PMID: 12898234]
  • Albert Koulman, Marlies E Kubbinga, Sieb Batterman, Herman J Woerdenbag, Niesko Pras, Jack G Woolley, Wim J Quax. A phytochemical study of lignans in whole plants and cell suspension cultures of Anthriscus sylvestris. Planta medica. 2003 Aug; 69(8):733-8. doi: 10.1055/s-2003-42776. [PMID: 14531024]
  • Seung Hyun Kim, Young Pyo Jang, Sang Hyun Sung, Chang Jong Kim, Jin Woong Kim, Young Choong Kim. Hepatoprotective dibenzylbutyrolactone lignans of Torreya nucifera against CCl4-induced toxicity in primary cultured rat hepatocytes. Biological & pharmaceutical bulletin. 2003 Aug; 26(8):1202-5. doi: 10.1248/bpb.26.1202. [PMID: 12913279]
  • S Heinonen, T Nurmi, K Liukkonen, K Poutanen, K Wähälä, T Deyama, S Nishibe, H Adlercreutz. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. Journal of agricultural and food chemistry. 2001 Jul; 49(7):3178-86. doi: 10.1021/jf010038a. [PMID: 11453749]
  • S D Sarker, Z Latif, R J Nash. Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites. Phytochemical analysis : PCA. 2001 Jan; 12(1):23-7. doi: 10.1002/1099-1565(200101/02)12:1<23::aid-pca551>3.0.co;2-e. [PMID: 11704958]