Jaceosidin (BioDeep_00000268525)

 

Secondary id: BioDeep_00000022502, BioDeep_00000229975

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-

化学式: C17H14O7 (330.0739494)
中文名称: 棕矢车菊素
谱图信息: 最多检出来源 Viridiplantae(plant) 24.31%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccc(c(c1)OC)O)O)OC)O
InChI: InChI=1S/C17H14O7/c1-22-13-5-8(3-4-9(13)18)12-6-10(19)15-14(24-12)7-11(20)17(23-2)16(15)21/h3-7,18,20-21H,1-2H3

描述信息

Jaceosidin, also known as 4,5,7-trihydroxy-3,6-dimethoxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, jaceosidin is considered to be a flavonoid lipid molecule. Jaceosidin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Jaceosidin can be found in lemon verbena, which makes jaceosidin a potential biomarker for the consumption of this food product.
Jaceosidin is a flavonoid isolated from Artemisia vestita, induces apoptosis in cancer cells, activates Bax and down-regulates Mcl-1 and c-FLIP expression[1]. Jaceosidin exhibits anti-cancer[2], anti-inflammatory activities, decreases leves of inflammatory markers, and suppresses COX-2 expression and NF-κB activation[3].
Jaceosidin is a flavonoid isolated from Artemisia vestita, induces apoptosis in cancer cells, activates Bax and down-regulates Mcl-1 and c-FLIP expression[1]. Jaceosidin exhibits anti-cancer[2], anti-inflammatory activities, decreases leves of inflammatory markers, and suppresses COX-2 expression and NF-κB activation[3].

同义名列表

10 个代谢物同义名

Jaceosidin; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxychromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4-chromenone; 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-chromone; 18085-97-7; 5,7-Dihydroxy-2- (4-hydroxy-3-methoxyphenyl) -6-methoxy-4H-1-benzopyran-4-one; 5,7,4-Trihydroxy-6,3-dimethoxyflavone



数据库引用编号

11 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)

226 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

  • Tanja Hell, Adriano Rutz, Lara Dürr, Maciej Dobrzyński, Jakob K Reinhardt, Timo Lehner, Morris Keller, Anika John, Mahabir Gupta, Olivier Pertz, Matthias Hamburger, Jean-Luc Wolfender, Eliane Garo. Combining Activity Profiling with Advanced Annotation to Accelerate the Discovery of Natural Products Targeting Oncogenic Signaling in Melanoma. Journal of natural products. 2022 06; 85(6):1540-1554. doi: 10.1021/acs.jnatprod.2c00146. [PMID: 35640148]
  • Eunkyo Park, Kwangseok Hong, Byoung-Mog Kwon, Yuri Kim, Jung-Hyun Kim. Jaceosidin Ameliorates Insulin Resistance and Kidney Dysfunction by Enhancing Insulin Receptor Signaling and the Antioxidant Defense System in Type 2 Diabetic Mice. Journal of medicinal food. 2020 Oct; 23(10):1083-1092. doi: 10.1089/jmf.2020.4739. [PMID: 32780673]
  • Hyemi Lee, Dain Jang, Jimin Jeon, Chanmi Cho, Sangil Choi, Seong Jae Han, Eunjeong Oh, Jiho Nam, Chan Hum Park, Yu Su Shin, Seung Pil Yun, Siyoung Yang, Li-Jung Kang. Seomae mugwort and jaceosidin attenuate osteoarthritic cartilage damage by blocking IκB degradation in mice. Journal of cellular and molecular medicine. 2020 07; 24(14):8126-8137. doi: 10.1111/jcmm.15471. [PMID: 32529755]
  • Wen-Rong Fu, Ji-Lei Chen, Xue-Yi Li, Jia-Xin Dong, Yi Liu. Bidirectional Regulatory Mechanisms of Jaceosidin on Mitochondria Function: Protective Effects of the Permeability Transition and Damage of Membrane Functions. The Journal of membrane biology. 2020 02; 253(1):25-35. doi: 10.1007/s00232-019-00102-4. [PMID: 31712855]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Jia-Xuan Xia, Bin-Bin Zhao, Jun-Feng Zan, Ping Wang, Lin-Lin Chen. Simultaneous determination of phenolic acids and flavonoids in Artemisiae Argyi Folium by HPLC-MS/MS and discovery of antioxidant ingredients based on relevance analysis. Journal of pharmaceutical and biomedical analysis. 2019 Oct; 175(?):112734. doi: 10.1016/j.jpba.2019.06.031. [PMID: 31330286]
  • Xiao-Lei Huang, Xiao-Chen Wei, Leng-Qiu Guo, Lei Zhao, Xi-Hua Chen, Ya-Dong Cui, Jie Yuan, Dao-Feng Chen, Jian Zhang. The therapeutic effects of Jaceosidin on lipopolysaccharide-induced acute lung injury in mice. Journal of pharmacological sciences. 2019 Jul; 140(3):228-235. doi: 10.1016/j.jphs.2019.07.004. [PMID: 31358372]
  • Jakob K Reinhardt, Amy M Klemd, Ombeline Danton, Maria De Mieri, Martin Smieško, Roman Huber, Thomas Bürgi, Carsten Gründemann, Matthias Hamburger. Sesquiterpene Lactones from Artemisia argyi: Absolute Configuration and Immunosuppressant Activity. Journal of natural products. 2019 06; 82(6):1424-1433. doi: 10.1021/acs.jnatprod.8b00791. [PMID: 31181920]
  • Xian-Zhang Huang, Li-Ping Kang, Li Gao, Yuan Zhang, Lan-Ping Guo, Lu-Qi Huang. [Quantative analysis of eupatilin and jaceosidin in folium of Artemisia argyi from different areas in China by RP-HPLC based on ancient medicine books]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Sep; 42(18):3504-3508. doi: 10.19540/j.cnki.cjcmm.20170814.009. [PMID: 29218934]
  • Zijun Ouyang, Wanshuai Li, Qianqian Meng, Qi Zhang, Xingqi Wang, Ahmed Elgehama, Xudong Wu, Yan Shen, Yang Sun, Xuefeng Wu, Qiang Xu. A natural compound jaceosidin ameliorates endoplasmic reticulum stress and insulin resistance via upregulation of SERCA2b. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 May; 89(?):1286-1296. doi: 10.1016/j.biopha.2017.03.023. [PMID: 28320096]
  • Brittany J Allison, Mark C Allenby, Shane S Bryant, Jae Eun Min, Mark Hieromnimon, P Matthew Joyner. Antibacterial activity of fractions from three Chumash medicinal plant extracts and in vitro inhibition of the enzyme enoyl reductase by the flavonoid jaceosidin. Natural product research. 2017 Mar; 31(6):707-712. doi: 10.1080/14786419.2016.1217201. [PMID: 27482826]
  • Seon Min Woo, Taeg Kyu Kwon. Jaceosidin induces apoptosis through Bax activation and down-regulation of Mcl-1 and c-FLIP expression in human renal carcinoma Caki cells. Chemico-biological interactions. 2016 Dec; 260(?):168-175. doi: 10.1016/j.cbi.2016.10.011. [PMID: 27729209]
  • Rohitesh Kumar, Yuting Lu, Alysha G Elliott, Angela M Kavanagh, Matthew A Cooper, Rohan A Davis. Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives. Magnetic resonance in chemistry : MRC. 2016 Nov; 54(11):880-886. doi: 10.1002/mrc.4482. [PMID: 27379746]
  • Jeong Soo Kim, Kwang Ho Cha, Seung Yeob Kang, Donghan Won, Sun Woo Jang, Miwon Son, Moon Ho Son, Ho Jung Choi, Young Won Lee, Myung Joo Kang. In vivo gastric residence and gastroprotective effect of floating gastroretentive tablet of DA-9601, an extract of Artemisia asiatica, in beagle dogs. Drug design, development and therapy. 2016; 10(?):1917-25. doi: 10.2147/dddt.s102918. [PMID: 27354765]
  • Ammar Bader, Tiziano Tuccinardi, Carlotta Granchi, Adriano Martinelli, Marco Macchia, Filippo Minutolo, Nunziatina De Tommasi, Alessandra Braca. Phenylpropanoids and flavonoids from Phlomis kurdica as inhibitors of human lactate dehydrogenase. Phytochemistry. 2015 Aug; 116(?):262-268. doi: 10.1016/j.phytochem.2015.03.007. [PMID: 25890391]
  • Sabrina Sait, Sabrina Hamri-Zeghichi, Lila Boulekbache-Makhlouf, Khodir Madani, Peggy Rigou, Virginia Brighenti, Francesco Pio Prencipe, Stefania Benvenuti, Federica Pellati. HPLC-UV/DAD and ESI-MS(n) analysis of flavonoids and antioxidant activity of an Algerian medicinal plant: Paronychia argentea Lam. Journal of pharmaceutical and biomedical analysis. 2015; 111(?):231-40. doi: 10.1016/j.jpba.2015.03.027. [PMID: 25910047]
  • Zsuzsanna Hajdú, Judit Hohmann, Peter Forgo, Imre Máthé, Judit Molnár, István Zupkó. Antiproliferative activity of Artemisia asiatica extract and its constituents on human tumor cell lines. Planta medica. 2014 Dec; 80(18):1692-7. doi: 10.1055/s-0034-1383146. [PMID: 25295671]
  • Heejung Yang, Dong Young Lee, Minji Jeon, Youngbae Suh, Sang Hyun Sung. Determination of five active compounds in Artemisia princeps and A. capillaris based on UPLC-DAD and discrimination of two species with multivariate analysis. Archives of pharmacal research. 2014 May; 37(5):617-25. doi: 10.1007/s12272-013-0204-5. [PMID: 23835834]
  • Kaan Polatoğlu, Omer Cem Karakoç, Fatih Demirci, Ayhan Gökçe, Nezhun Gören. Chemistry and biological activities of Tanacetum chiliophyllum var. oligocephalum extracts. Journal of AOAC International. 2013 Nov; 96(6):1222-7. doi: 10.5740/jaoacint.sgepolatoglu. [PMID: 24645497]
  • Geun Cheol Song, Shi Yong Ryu, Young Sup Kim, Ji Young Lee, Jung Sup Choi, Choong-Min Ryu. Elicitation of induced resistance against Pectobacterium carotovorum and Pseudomonas syringae by specific individual compounds derived from native Korean plant species. Molecules (Basel, Switzerland). 2013 Oct; 18(10):12877-95. doi: 10.3390/molecules181012877. [PMID: 24135942]
  • Youngpyo Nam, Mijung Choi, Heehong Hwang, Maan-Gee Lee, Byoung-Mog Kwon, Won-Ha Lee, Kyoungho Suk. Natural flavone jaceosidin is a neuroinflammation inhibitor. Phytotherapy research : PTR. 2013 Mar; 27(3):404-11. doi: 10.1002/ptr.4737. [PMID: 22619052]
  • Ayumi Uehara, Tsukasa Iwashina. Flavonoids from the Japanese monotypic genus, Nipponanthemum. Natural product communications. 2012 Aug; 7(8):1005-6. doi: . [PMID: 22978216]
  • Mi Ja Chung, Jeong-Mi Kim, Sangchul Lee, Taewoo Kim, Daejung Kim, Jongmi Baek, Taehyuk Kim, Jaesung Lee, Kyoungkon Kim, Jin A Yoon, Myeon Choe. Suppressive effects of Schizandra chinensis Baillon water extract on allergy-related cytokine generation and degranulation in IgE-antigen complex-stimulated RBL-2H3 cells. Nutrition research and practice. 2012 Apr; 6(2):97-105. doi: 10.4162/nrp.2012.6.2.97. [PMID: 22586497]
  • Shuangqing Wu, Qun Sun, Chunjun Chu, Jian Zhang. [Chemical constituents of Eupatorium lindleyanum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Apr; 37(7):937-40. doi: . [PMID: 22792793]
  • Muhammad Khan, Bo Yu, Azhar Rasul, Ali Al Shawi, Fei Yi, Hong Yang, Tonghui Ma. Jaceosidin Induces Apoptosis in U87 Glioblastoma Cells through G2/M Phase Arrest. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):703034. doi: 10.1155/2012/703034. [PMID: 22216058]
  • Joshua N Fletcher, A Douglas Kinghorn, Jay P Slack, T Scott McCluskey, Amy Odley, Zhonghua Jia. In vitro evaluation of flavonoids from Eriodictyon californicum for antagonist activity against the bitterness receptor hTAS2R31. Journal of agricultural and food chemistry. 2011 Dec; 59(24):13117-21. doi: 10.1021/jf204359q. [PMID: 22059530]
  • Kumaresan P Thirupathy, Asish Tulshkar, C Vijaya. Neuropharmacological activity of Lippia nodiflora Linn. Pharmacognosy research. 2011 Jul; 3(3):194-200. doi: 10.4103/0974-8490.85007. [PMID: 22022169]
  • Won Young Song, Hye Young Ji, Nam-In Baek, Tae-Sook Jeong, Hye Suk Lee. In vitro metabolism of jaceosidin and characterization of cytochrome P450 and UDP-glucuronosyltransferase enzymes in human liver microsomes. Archives of pharmacal research. 2010 Dec; 33(12):1985-96. doi: 10.1007/s12272-010-1214-1. [PMID: 21191764]
  • Dong Hee Na. Metabolism study of botanical drugs. Archives of pharmacal research. 2010 Dec; 33(12):1877-9. doi: 10.1007/s12272-010-1200-7. [PMID: 21191750]
  • Won Young Song, Nam Jin Kim, Sung Yeon Kim, Hye Suk Lee. Liquid chromatography-tandem mass spectrometry for the determination of jaceosidin in rat plasma. Journal of pharmaceutical and biomedical analysis. 2009 Feb; 49(2):381-6. doi: 10.1016/j.jpba.2008.10.021. [PMID: 19070985]
  • Ye Yin, Fang-Yuan Gong, Xing-Xin Wu, Yang Sun, Yi-Hua Li, Ting Chen, Qiang Xu. Anti-inflammatory and immunosuppressive effect of flavones isolated from Artemisia vestita. Journal of ethnopharmacology. 2008 Oct; 120(1):1-6. doi: 10.1016/j.jep.2008.07.029. [PMID: 18721870]
  • Min-Jung Kim, Jong-Min Han, Yue-Yan Jin, Nam-In Baek, Myun-Ho Bang, Hae-Gon Chung, Myung-Sook Choi, Kyung-Tae Lee, Dai-Eun Sok, Tae-Sook Jeong. In vitro antioxidant and anti-inflammatory activities of Jaceosidin from Artemisia princeps Pampanini cv. Sajabal. Archives of pharmacal research. 2008 Apr; 31(4):429-37. doi: 10.1007/s12272-001-1175-8. [PMID: 18449499]
  • M Clavin, S Gorzalczany, A Macho, E Muñoz, G Ferraro, C Acevedo, V Martino. Anti-inflammatory activity of flavonoids from Eupatorium arnottianum. Journal of ethnopharmacology. 2007 Jul; 112(3):585-9. doi: 10.1016/j.jep.2007.04.007. [PMID: 17570627]
  • Canan Karamenderes, Erdal Bedir, Rahul Pawar, Sura Baykan, Ikhlas A Khan. Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana. Phytochemistry. 2007 Mar; 68(5):609-15. doi: 10.1016/j.phytochem.2006.10.013. [PMID: 17126864]
  • Valeria Moscatelli, Oksana Hnatyszyn, Cristina Acevedo, Javier Megías, María José Alcaraz, Graciela Ferraro. Flavonoids from Artemisia copa with anti-inflammatory activity. Planta medica. 2006 Jan; 72(1):72-4. doi: 10.1055/s-2005-873177. [PMID: 16450301]
  • Hee-Gu Lee, Kyung-Ae Yu, Won-Keun Oh, Tae-Woong Baeg, Hyun-Cheol Oh, Jong-Seog Ahn, Won-Cheoul Jang, Jong-Wan Kim, Jong-Seok Lim, Yong-Kyung Choe, Do-Young Yoon. Inhibitory effect of jaceosidin isolated from Artemisiaargyi on the function of E6 and E7 oncoproteins of HPV 16. Journal of ethnopharmacology. 2005 Apr; 98(3):339-43. doi: 10.1016/j.jep.2005.01.054. [PMID: 15814270]
  • Alejandro Tapia, Jaime Rodriguez, Cristina Theoduloz, Susana Lopez, Gabriela Egly Feresin, Guillermo Schmeda-Hirschmann. Free radical scavengers and antioxidants from Baccharis grisebachii. Journal of ethnopharmacology. 2004 Dec; 95(2-3):155-61. doi: 10.1016/j.jep.2004.06.035. [PMID: 15507329]
  • Dexiu Zhao, Chunxiang Fu, Yaqiong Chen, Fengshan Ma. Transformation of Saussurea medusa for hairy roots and jaceosidin production. Plant cell reports. 2004 Dec; 23(7):468-74. doi: 10.1007/s00299-004-0840-9. [PMID: 15290084]
  • Shi-hui Qian, Nian-yun Yang, Jin-ao Duan, Li-hong Yuan, Li-juan Tian. [Study on the flavonoids of Eupatorium lindleyanum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Jan; 29(1):50-2. doi: ". [PMID: 15709382]
  • Ae Ra Kim, Ya Ni Zou, Tae Hyun Park, Kyung Hee Shim, Min Sun Kim, Nam Deuk Kim, Jong Deog Kim, Song Ja Bae, Jae Sue Choi, Hae Young Chung. Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. Phytotherapy research : PTR. 2004 Jan; 18(1):1-7. doi: 10.1002/ptr.1358. [PMID: 14750192]
  • D Zhao, Y Huang, Z Jin, W Qu, D Lu. Effect of aggregate size in cell cultures of Saussurea medusa on cell growth and jaceosidin production. Plant cell reports. 2003 Jul; 21(11):1129-33. doi: 10.1007/s00299-003-0631-8. [PMID: 12836008]
  • Tsuneatsu Nagao, Fumiko Abe, Junei Kinjo, Hikaru Okabe. Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biological & pharmaceutical bulletin. 2002 Jul; 25(7):875-9. doi: 10.1248/bpb.25.875. [PMID: 12132661]