Fangchinoline (BioDeep_00000171811)

Main id: BioDeep_00000230483

 

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24(32),25,27(31),35-dodecaen-21-ol

化学式: C37H40N2O6 (608.288622)
中文名称: 防己诺林碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3

描述信息

(R)-Fangchinoline (Thalrugosine), a alkaloids from Stephania tetrandra，exhibits antimicrobial and hypotensive activity. The roots and stems of several plants from genus Stephania are all used as traditional Chinese medicine and have been used for treatment of fever, diarrhea, dyspepsia and urinary disease[1].
(R)-Fangchinoline (Thalrugosine), a alkaloids from Stephania tetrandra，exhibits antimicrobial and hypotensive activity. The roots and stems of several plants from genus Stephania are all used as traditional Chinese medicine and have been used for treatment of fever, diarrhea, dyspepsia and urinary disease[1].

同义名列表

10 个代谢物同义名

9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24(32),25,27(31),35-dodecaen-21-ol; (1beta)-isomer of fangchinoline; 7-O-demethyl-tetrandrine; 7-O-demethyltetrandrine; isofangchinoline; Fangchinoline; thalrugosine; thaligine; limacine; (R)-Fangchinoline



数据库引用编号

6 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)

46 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

  • Yanxiong Shao, Chaoran Li, Guojun Miao, Yubo Xu. Fangchinoline, an Extract of the Stephania tetrandra S. Moore Root, Promoted Oxidative Stress-induced DNA Damage and Apoptosis and Inhibited Akt Signaling in Jurkat T Cells. Current molecular pharmacology. 2024; 17(1):e100223213590. doi: 10.2174/1874467216666230210152454. [PMID: 36809961]
  • Wangming Zhang, Xiaojing Yu, Linchun Bao, Tianhui He, Weidong Pan, Pinhao Li, Jinhe Liu, Xiaohua Liu, Liuqi Yang, Jielin Liu. Bisbenzylisoquinoline alkaloid fangchinoline derivative HY-2 inhibits breast cancer cells by suppressing BLM DNA helicase. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Dec; 169(?):115908. doi: 10.1016/j.biopha.2023.115908. [PMID: 37988849]
  • Jia-Shu Chen, Xu Guo, Jin-Yue Sun, Mu-Xuan Wang, Xiu-Zheng Gao, Zhen Wang, Jin-Long Han, Hui Sun, Kai Zhang, Chao Liu. Fangchinoline derivatives inhibits PI3K signaling in vitro and in vivo in non-small cell lung cancer. Bioorganic chemistry. 2023 09; 138(?):106623. doi: 10.1016/j.bioorg.2023.106623. [PMID: 37295240]
  • Jiao Guan, Liming Wang, Yuan Ji, Tianyi Zhang, Ye Sang, Sheng Chang, Bo Feng, Heyun Zhu. UHPLC-MS/MS Method for Quantifying Fangchinoline, Tetrandrine and Calycosin-7-O-β-D-Glucoside of Fangji Huangqi Decoction in Rat Plasma and Its Application to a Pharmacokinetic Study. Journal of chromatographic science. 2022 Jun; 60(5):458-464. doi: 10.1093/chromsci/bmab116. [PMID: 34734235]
  • Xiang-Peng Kong, Hai-Qin Ren, Etta Y L Liu, Ka-Wing Leung, Shu-Chen Guo, Ran Duan, Tina T X Dong, Karl W K Tsim. The Cholinesterase Inhibitory Properties of Stephaniae Tetrandrae Radix. Molecules (Basel, Switzerland). 2020 Dec; 25(24):. doi: 10.3390/molecules25245914. [PMID: 33327436]
  • Qi Wang, Baohe Tang, Minhui Cao. Synthesis, characterization, and fungicidal activity of novel Fangchinoline derivatives. Bioorganic & medicinal chemistry. 2020 12; 28(23):115778. doi: 10.1016/j.bmc.2020.115778. [PMID: 33007609]
  • Yingsong Jiang, Jiguo Liu, Zemei Zhou, Ke Liu, Chun Liu. Fangchinoline Protects Against Renal Injury in Diabetic Nephropathy by Modulating the MAPK Signaling Pathway. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2020 Aug; 128(8):499-505. doi: 10.1055/a-0636-3883. [PMID: 30049003]
  • Wencheng Xu, Shuhe Chen, Xiaoqin Wang, Hongguang Wu, Haruki Yamada, Toshihiko Hirano. Bisbenzylisoquinoline alkaloids and P-glycoprotein function: A structure activity relationship study. Bioorganic & medicinal chemistry. 2020 06; 28(12):115553. doi: 10.1016/j.bmc.2020.115553. [PMID: 32503690]
  • Xiang-Peng Kong, Etta Y L Liu, Zhi-Cong Chen, Miranda Li Xu, Anna X D Yu, Qi-Yun Wu, Ying-Jie Xia, Ran Duan, Tina T X Dong, Karl W K Tsim. Synergistic Inhibition of Acetylcholinesterase by Alkaloids Derived from Stephaniae Tetrandrae Radix, Coptidis Rhizoma and Phellodendri Chinensis Cortex. Molecules (Basel, Switzerland). 2019 Dec; 24(24):. doi: 10.3390/molecules24244567. [PMID: 31847089]
  • Dong Eon Kim, Jung Sun Min, Min Seong Jang, Jun Young Lee, Young Sup Shin, Jong Hwan Song, Hyoung Rae Kim, Seungtaek Kim, Young-Hee Jin, Sunoh Kwon. Natural Bis-Benzylisoquinoline Alkaloids-Tetrandrine, Fangchinoline, and Cepharanthine, Inhibit Human Coronavirus OC43 Infection of MRC-5 Human Lung Cells. Biomolecules. 2019 11; 9(11):. doi: 10.3390/biom9110696. [PMID: 31690059]
  • Lu Shan, Liu Tong, Li Hang, Hongwu Fan. Fangchinoline supplementation attenuates inflammatory markers in experimental rheumatoid arthritis-induced rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Mar; 111(?):142-150. doi: 10.1016/j.biopha.2018.12.043. [PMID: 30579253]
  • Qi Wu, Haojie Liu, Ming Zhou. Fangchinoline Ameliorates Diabetic Retinopathy by Inhibiting Receptor for Advanced Glycation End-Products (RAGE)-Nuclear Factor Kappa-Light-Chain-Enhancer of Activated B Cells (NF-κB) Pathway in Streptozotocin (STZ)-Induced Diabetic Rats. Medical science monitor : international medical journal of experimental and clinical research. 2019 Feb; 25(?):1113-1121. doi: 10.12659/msm.912927. [PMID: 30739905]
  • Weiwei Tang, Bingjie Jia, Jie Zhou, Jing Liu, Jiancheng Wang, Dingyuan Ma, Ping Li, Jun Chen. A method using angiotensin converting enzyme immobilized on magnetic beads for inhibitor screening. Journal of pharmaceutical and biomedical analysis. 2019 Feb; 164(?):223-230. doi: 10.1016/j.jpba.2018.09.054. [PMID: 30391811]
  • Wenjun Zhu, Wenge Ding, Xiaojun Shang, Ding Zhu, Xiaoyu Dai. Fangchinoline Promotes Autophagy and Inhibits Apoptosis in Osteoporotic Rats. Medical science monitor : international medical journal of experimental and clinical research. 2019 Jan; 25(?):324-332. doi: 10.12659/msm.912624. [PMID: 30632520]
  • Jie Shi, Bingyu Guo, Qiang Hui, Peng Chang, Kai Tao. Fangchinoline suppresses growth and metastasis of melanoma cells by inhibiting the phosphorylation of FAK. Oncology reports. 2017 Jul; 38(1):63-70. doi: 10.3892/or.2017.5678. [PMID: 28560386]
  • XinGang Lu, RuoXi Zhang, Feng Fu, Jie Shen, Hua Nian, Tao Wu. Simultaneous Determination of Fangchinoline and Tetrandrine in Qi-Fang-Xi-Bi-Granules by RP-HPLC. Journal of chromatographic science. 2015 Sep; 53(8):1328-32. doi: 10.1093/chromsci/bmv016. [PMID: 25754692]
  • Xiaoli Wang, Xiao Liu, Hao Cai, Ke Pei, Gang Cao, Xiaoyan Xu, Fa Shi, Baochang Cai. Ultra high performance liquid chromatography with tandem mass spectrometry method for the determination of tetrandrine and fangchinoline in rat plasma after oral administration of Fangji Huangqi Tang and Stephania tetrandra S. Moore extracts. Journal of separation science. 2015 May; 38(8):1286-93. doi: 10.1002/jssc.201401384. [PMID: 25645647]
  • Xiaoli Wang, Xiao Liu, Xiaoyan Xu, Tingting Zhu, Fa Shi, Kunming Qin, Baochang Cai. Screening and identification of multiple constituents and their metabolites of Fangji Huangqi Tang in rats by ultra-high performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry basing on coupling data processing techniques. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Mar; 985(?):14-28. doi: 10.1016/j.jchromb.2015.01.021. [PMID: 25656758]
  • Yan Tang, Ailing Sun, Renmin Liu, Yongqing Zhang. Simultaneous determination of fangchinoline and tetrandrine in Stephania tetrandra S. Moore by using 1-alkyl-3-methylimidazolium-based ionic liquids as the RP-HPLC mobile phase additives. Analytica chimica acta. 2013 Mar; 767(?):148-54. doi: 10.1016/j.aca.2013.01.001. [PMID: 23452799]
  • Lihong Liu, Shenglan Li, Zilin Chen. Simultaneous determination of tetrandrine and fangchinoline in herbal medicine Stephania tetrandra S. Moore by liquid chromatography with electrochemical detection. Journal of pharmaceutical and biomedical analysis. 2012 Mar; 61(?):252-5. doi: 10.1016/j.jpba.2011.11.027. [PMID: 22196802]
  • Zhitao Wan, Yimei Lu, Qingjiao Liao, Yang Wu, Xulin Chen. Fangchinoline inhibits human immunodeficiency virus type 1 replication by interfering with gp160 proteolytic processing. PloS one. 2012; 7(6):e39225. doi: 10.1371/journal.pone.0039225. [PMID: 22720080]
  • Aun Chea, Sok-Siya Bun, Nadine Azas, Monique Gasquet, Sothavireak Bory, Evelyne Ollivier, Riad Elias. Antiplasmodial activity of three bisbenzylisoquinoline alkaloids from the tuber of Stephania rotunda. Natural product research. 2010 Nov; 24(18):1766-70. doi: 10.1080/14786410903395624. [PMID: 20981617]
  • Li He, Junyi Yang, Li'na Hu. [Transmembrane transport activity of paclitaxel regulated by fangchinoline in MDR1-mDCK II cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jun; 35(11):1478-81. doi: ". [PMID: 20822025]
  • Ilhami Gülçin, Riad Elias, Akçahan Gepdiremen, Aun Chea, Fevzi Topal. Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline. Journal of enzyme inhibition and medicinal chemistry. 2010 Feb; 25(1):44-53. doi: 10.3109/14756360902932792. [PMID: 20030508]
  • Lihong Liu, Xinxian Deng, Xingguo Chen. Micelle to trapping solution stacking in micellar electrokinetic chromatography. Journal of chromatography. A. 2010 Jan; 1217(1):175-8. doi: 10.1016/j.chroma.2009.11.038. [PMID: 19945115]
  • Zhonghong Li, Xialei Fan, Meiming Cai, Zhihong Yang, Jian Ying, Guifen Qiang, Guanhua Du. [Pharmacokinetics of fangchinoline and tetrandrine in rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Dec; 34(23):3110-3. doi: NULL. [PMID: 20222434]
  • Qiu-hua Wu, Chun Wang, Zhi Wang, Jing-jun Ma, Xiao-huan Zang, Na-xin Qin. [Study on the interaction between fangchinoline and bovine serum albumin]. Guang pu xue yu guang pu fen xi = Guang pu. 2007 Dec; 27(12):2498-501. doi: NULL. [PMID: 18330294]
  • Wenjie Ma, Masaaki Nomura, Tatsuo Takahashi-Nishioka, Shinjiro Kobayashi. Combined effects of fangchinoline from Stephania tetrandra Radix and formononetin and calycosin from Astragalus membranaceus Radix on hyperglycemia and hypoinsulinemia in streptozotocin-diabetic mice. Biological & pharmaceutical bulletin. 2007 Nov; 30(11):2079-83. doi: 10.1248/bpb.30.2079. [PMID: 17978479]
  • Yu-Qin Li, Xing-Guo Chen, Yong-Xiu Qi, Ke Li, Bao-Xiu Jia, Cai-Hong Liu, Ming-Liang Cao. [Determination of tetrandrine and fangchinoline in Radix Stephaniae tetrandrae and its preparation by nonaqueous capillary chromatography]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Oct; 32(19):1992-5. doi: ". [PMID: 18161288]
  • Cailing Yang, Linyuan Guo, Xiaoyan Liu, Haixia Zhang, Mancang Liu. Determination of tetrandrine and fangchinoline in plasma samples using hollow fiber liquid-phase microextraction combined with high-performance liquid chromatography. Journal of chromatography. A. 2007 Sep; 1164(1-2):56-64. doi: 10.1016/j.chroma.2007.07.019. [PMID: 17675049]
  • H L Koh, H Wang, S Zhou, E Chan, S O Woo. Detection of aristolochic acid I, tetrandrine and fangchinoline in medicinal plants by high performance liquid chromatography and liquid chromatography/mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2006 Feb; 40(3):653-61. doi: 10.1016/j.jpba.2005.08.001. [PMID: 16168604]
  • Nobuyasu Sekiya, Hiroaki Hikiami, Koichi Yokoyama, Kazufumi Kouta, Iwao Sakakibara, Yutaka Shimada, Katsutoshi Terasawa. Inhibitory effects of Stephania tetrandra S. Moore on free radical-induced lysis of rat red blood cells. Biological & pharmaceutical bulletin. 2005 Apr; 28(4):667-70. doi: 10.1248/bpb.28.667. [PMID: 15802807]
  • L H Fang, Y H Zhang, B S Ku. Fangchinoline inhibited the antinociceptive effect of morphine in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2005 Mar; 12(3):183-8. doi: 10.1016/j.phymed.2003.06.007. [PMID: 15830839]
  • Ren-min Liu, Feng-yun He, Ai-ling Sun. [Separation and identification of alkaloids in Stephania tetrandra by capillary electrophoresis electrospray-MS/MS]. Yao xue xue bao = Acta pharmaceutica Sinica. 2004 May; 39(5):363-6. doi: ". [PMID: 15338880]
  • Yong-He Zhang, Lian-Hua Fang, Bao-Shan Ku. Fangchinoline inhibits rat aortic vascular smooth muscle cell proliferation and cell cycle progression through inhibition of ERK1/2 activation and c-fos expression. Biochemical pharmacology. 2003 Nov; 66(9):1853-60. doi: 10.1016/s0006-2952(03)00550-1. [PMID: 14563495]
  • Sang Bum Koh, Ju Yeon Ban, Bo Young Lee, Yeon Hee Seong. Protective effects of fangchinoline and tetrandrine on hydrogen peroxide-induced oxidative neuronal cell damage in cultured rat cerebellar granule cells. Planta medica. 2003 Jun; 69(6):506-12. doi: 10.1055/s-2003-40647. [PMID: 12865967]
  • Taiki Tsutsumi, Shinjiro Kobayashi, Yuan Ying Liu, Hitoshi Kontani. Anti-hyperglycemic effect of fangchinoline isolated from Stephania tetrandra Radix in streptozotocin-diabetic mice. Biological & pharmaceutical bulletin. 2003 Mar; 26(3):313-7. doi: 10.1248/bpb.26.313. [PMID: 12612439]
  • M Hristova, M Yordanov, N Ivanovska. Effect of fangchinoline in murine models of multiple organ dysfunction syndrome and septic shock. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2003 Jan; 52(1):1-7. doi: 10.1007/s000110300007. [PMID: 12608643]
  • Y C Shen, C J Chou, W F Chiou, C F Chen. Anti-inflammatory effects of the partially purified extract of radix Stephaniae tetrandrae: comparative studies of its active principles tetrandrine and fangchinoline on human polymorphonuclear leukocyte functions. Molecular pharmacology. 2001 Nov; 60(5):1083-90. doi: . [PMID: 11641437]
  • T M Wong, S Wu, X C Yu, H Y Li. Cardiovascular actions of Radix Stephaniae Tetrandrae: a comparison with its main component, tetrandrine. Acta pharmacologica Sinica. 2000 Dec; 21(12):1083-8. doi: . [PMID: 11603280]
  • M Hristova, R Istatkova. Complement-mediated antiinflammatory effect of bisbenzylisoquinoline alkaloid fangchinoline. Phytomedicine : international journal of phytotherapy and phytopharmacology. 1999 Nov; 6(5):357-62. doi: 10.1016/s0944-7113(99)80059-2. [PMID: 11962544]
  • N Ivanovska, M Hristova, S Philipov. Complement modulatory activity of bisbenzylisoquinoline alkaloids isolated from Isopyrum thalictroides--II. Influence on C3-9 reactions in vitro and antiinflammatory effect in vivo. International journal of immunopharmacology. 1999 May; 21(5):337-47. doi: 10.1016/s0192-0561(99)00015-6. [PMID: 10408630]
  • H S Kim, Y H Zhang, Y P Yun. Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation. Planta medica. 1999 Mar; 65(2):135-8. doi: 10.1055/s-1999-13974. [PMID: 10193204]
  • J Huang, J Guo, G Duan. [Determination of 7 bio-active alkaloids in Stephania plants by RP-HPLC]. Yao xue xue bao = Acta pharmaceutica Sinica. 1998 Jul; 33(7):528-33. doi: . [PMID: 12016887]