Magnoflorine (BioDeep_00000000293)

 

Secondary id: BioDeep_00000402833, BioDeep_00000896564, BioDeep_00001892607

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


5,6,6a(S),7-Tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4H-dibenzo[de,g]quinolinium chloride

化学式: C20H24NO4+ (342.17052440000003)
中文名称: (+)-木兰花碱, 木兰花碱, 木蘭花鹼
谱图信息: 最多检出来源 Viridiplantae(plant) 0.02%

分子结构信息

SMILES: COc1ccc2c(c1O)-c1c(O)c(OC)cc3c1[C@H](C2)[N+](C)(C)CC3
InChI: InChI=1S/C20H23NO4/c1-21(2)8-7-12-10-15(25-4)20(23)18-16(12)13(21)9-11-5-6-14(24-3)19(22)17(11)18/h5-6,10,13H,7-9H2,1-4H3,(H-,22,23)/p+1/t13-/m0/s1

描述信息

(S)-magnoflorine is an aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group. It has a role as a plant metabolite. It is an aporphine alkaloid and a quaternary ammonium ion. It is functionally related to a (S)-corytuberine.
Magnoflorine is a natural product found in Zanthoxylum myriacanthum, Fumaria capreolata, and other organisms with data available.
See also: Caulophyllum thalictroides Root (part of).

同义名列表

29 个代谢物同义名

5,6,6a(S),7-Tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4H-dibenzo[de,g]quinolinium chloride; 4H-Dibenzo(de,g)quinolinium, 5,6,6a,7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-,(6aS)-; (6aS)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinolinium; (6aS)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolinium; (6AS)-5,6,6A,7-TETRAHYDRO-1,11-DIHYDROXY-2,10-DIMETHOXY-6,6-DIMETHYL-4H-DIBENZO(DE,G)QUINOLINIUM; (6aS)-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-1,11-diol; 5,6,6aS,7-tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4H-dibenzo[de,g]quinolinium; Magnoflorine (iodide);-Magnoflorine (iodide);Thalictrine (iodide); 6a-alpha-Aporphinium, 1,11-dihydroxy-2,10-dimethoxy-6-methyl-; magnoflorine perchlorate, (S)-isomer; magnoflorine iodide, (S)-isomer; Magnoflorine, >=98\\% (HPLC); Corytuberine methosalt; .ALPHA.-MAGNOFLORINE; alpha-MAGNOFLORINE; MAGNOFLORINE [MI]; (+)-Magnoflorine; (S)-magnoflorine; UNII-NI8K6962K4; Magnoflorine; Thalictrine; NI8K6962K4; Thalictrin; 1ST157266; Escholine; Esholine; Escholin; (+)-Magnoflorine iodide; Magnoflorine



数据库引用编号

17 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

32 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(30)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

455 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

  • Lu Liu, Xiaohua Li. Pharmacokinetic study of the interaction between luteolin and magnoflorine in rats. Chemical biology & drug design. 2023 Sep; ?(?):. doi: 10.1111/cbdd.14356. [PMID: 37731180]
  • Bao-Juan Xue, Wen-Wen Zhao, Xiu-Rui Sun, Zhe Zhang, Jian-Hua Chen, Yu-Jie Zhang. [Influence of coexisting components in Coptidis Rhizoma on excretion of magnoflorine in rat bile, urine, and feces]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Jul; 47(14):3908-3914. doi: 10.19540/j.cnki.cjcmm.20220121.201. [PMID: 35850849]
  • Hao Xu, Yuyu Niu, Yan Sun, Menglin Xia, Daozheng Lin, Wei Qiao. Separation and purification of magnoflorine, spinosin, and 6‴-feruloyspinosin from Ziziphi Spinosae Semen by high-speed counter-current chromatography. Journal of separation science. 2021 Jun; 44(12):2391-2398. doi: 10.1002/jssc.202100122. [PMID: 33848379]
  • Estera Okon, Wirginia Kukula-Koch, Marta Halasa, Agata Jarzab, Marzena Baran, Magdalena Dmoszynska-Graniczka, Apostolis Angelis, Eleftherios Kalpoutzakis, Malgorzata Guz, Andrzej Stepulak, Anna Wawruszak. Magnoflorine-Isolation and the Anticancer Potential against NCI-H1299 Lung, MDA-MB-468 Breast, T98G Glioma, and TE671 Rhabdomyosarcoma Cancer Cells. Biomolecules. 2020 11; 10(11):. doi: 10.3390/biom10111532. [PMID: 33182753]
  • Yu-Feng Huang, Fan He, Can-Jian Wang, Ying Xie, Yan-Yu Zhang, Zhen Sang, Ping Qiu, Pei Luo, Sheng-Yuan Xiao, Jing Li, Fei-Ci Wu, Liang Liu, Hua Zhou. Discovery of chemical markers for improving the quality and safety control of Sinomenium acutum stem by the simultaneous determination of multiple alkaloids using UHPLC-QQQ-MS/MS. Scientific reports. 2020 08; 10(1):14182. doi: 10.1038/s41598-020-71133-4. [PMID: 32843671]
  • Xiao-Li Sun, Xin-Wu Zhang, Hong-Jun Zhai, Di Zhang, Shuang-Yu Ma. Magnoflorine inhibits human gastric cancer progression by inducing autophagy, apoptosis and cell cycle arrest by JNK activation regulated by ROS. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 May; 125(?):109118. doi: 10.1016/j.biopha.2019.109118. [PMID: 32106366]
  • Estera Okon, Jarogniew J Luszczki, Wirginia Kukula-Koch, Marta Halasa, Agata Jarzab, Daariimaa Khurelbat, Andrzej Stepulak, Anna Wawruszak. Synergistic or Additive Pharmacological Interactions between Magnoflorine and Cisplatin in Human Cancer Cells of Different Histological Origin. International journal of molecular sciences. 2020 Apr; 21(8):. doi: 10.3390/ijms21082848. [PMID: 32325867]
  • Xiufang Liang, Yunan Xiang, Yanling Li, Ping Feng, Yongping Qin, Xianrong Lai. A rapid method for simultaneous quantification of berberine, berbamine, magnoflorine and berberrubine in mouse serum using UPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Apr; 1142(?):122040. doi: 10.1016/j.jchromb.2020.122040. [PMID: 32145638]
  • Yuyan Guo, Shaowa Lü, Bingyou Yang, Guoyu Li, Wenbao Ma, Qiaoxin Guo, Qiuhong Wang, Haixue Kuang. HPLC-MS/MS method for the determination and pharmacokinetic study of six compounds against rheumatoid arthritis in rat plasma after oral administration of the extract of Caulophyllum robustum Maxim. Journal of pharmaceutical and biomedical analysis. 2020 Mar; 181(?):112923. doi: 10.1016/j.jpba.2019.112923. [PMID: 32029347]
  • Estera Okon, Wirginia Kukula-Koch, Agata Jarzab, Marta Halasa, Andrzej Stepulak, Anna Wawruszak. Advances in Chemistry and Bioactivity of Magnoflorine and Magnoflorine-Containing Extracts. International journal of molecular sciences. 2020 Feb; 21(4):. doi: 10.3390/ijms21041330. [PMID: 32079131]
  • Tong Xu, Tingting Kuang, Huan Du, Qi Li, Tu Feng, Yi Zhang, Gang Fan. Magnoflorine: A review of its pharmacology, pharmacokinetics and toxicity. Pharmacological research. 2020 02; 152(?):104632. doi: 10.1016/j.phrs.2020.104632. [PMID: 31911246]
  • Xi-Yang Tang, Zi-Qin Dai, Qing-Chang Wu, Jia-Xing Zeng, Meng-Xue Gao, Hui-Hui Xiao, Zhi-Hong Yao, Yi Dai, Xin-Sheng Yao. Simultaneous determination of multiple components in rat plasma and pharmacokinetic studies at a pharmacodynamic dose of Xian-Ling-Gu-Bao capsule by UPLC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2020 Jan; 177(?):112836. doi: 10.1016/j.jpba.2019.112836. [PMID: 31473481]
  • Tian Wei, Xie Xiaojun, Cao Peilong. Magnoflorine improves sensitivity to doxorubicin (DOX) of breast cancer cells via inducing apoptosis and autophagy through AKT/mTOR and p38 signaling pathways. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Jan; 121(?):109139. doi: 10.1016/j.biopha.2019.109139. [PMID: 31707337]
  • Anahí Canedo-Téxon, Feliza Ramón-Farias, Juan Luis Monribot-Villanueva, Emanuel Villafán, Alexandro Alonso-Sánchez, Claudia Anahí Pérez-Torres, Guillermo Ángeles, José Antonio Guerrero-Analco, Enrique Ibarra-Laclette. Novel findings to the biosynthetic pathway of magnoflorine and taspine through transcriptomic and metabolomic analysis of Croton draco (Euphorbiaceae). BMC plant biology. 2019 Dec; 19(1):560. doi: 10.1186/s12870-019-2195-y. [PMID: 31852435]
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  • Jaegoo Kim, Thinh Ha Quang Bao, Yu-Kyong Shin, Ki-Young Kim. Antifungal activity of magnoflorine against Candida strains. World journal of microbiology & biotechnology. 2018 Oct; 34(11):167. doi: 10.1007/s11274-018-2549-x. [PMID: 30382403]
  • Xiao Tian, Sen Guo, Kan He, Marc Roller, Meiqi Yang, Qingchao Liu, Li Zhang, Chi-Tang Ho, Naisheng Bai. Qualitative and quantitative analysis of chemical constituents of Ptychopetalum olacoides Benth. Natural product research. 2018 Feb; 32(3):354-357. doi: 10.1080/14786419.2017.1354187. [PMID: 28750557]
  • Wirginia Kukula-Koch, Marta Kruk-Słomka, Katarzyna Stępnik, Radosław Szalak, Grażyna Biała. The Evaluation of Pro-Cognitive and Antiamnestic Properties of Berberine and Magnoflorine Isolated from Barberry Species by Centrifugal Partition Chromatography (CPC), in Relation to QSAR Modelling. International journal of molecular sciences. 2017 11; 18(12):. doi: 10.3390/ijms18122511. [PMID: 29186770]
  • Chao-Zhan Lin, Zhu-Jie Liu, Zeren-Dawa Bairi, Chen-Chen Zhu. A new diterpenoid alkaloid isolated from Delphinium caeruleum. Chinese journal of natural medicines. 2017 Jan; 15(1):45-48. doi: 10.1016/s1875-5364(17)30007-9. [PMID: 28259252]
  • Jeremy S Morris, Peter J Facchini. Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy. The Journal of biological chemistry. 2016 Nov; 291(45):23416-23427. doi: 10.1074/jbc.m116.750893. [PMID: 27634038]
  • Wirginia Kukula-Koch, Wojciech Koch, Apostolis Angelis, Maria Halabalaki, Nektarios Aligiannis. Application of pH-zone refining hydrostatic countercurrent chromatography (hCCC) for the recovery of antioxidant phenolics and the isolation of alkaloids from Siberian barberry herb. Food chemistry. 2016 Jul; 203(?):394-401. doi: 10.1016/j.foodchem.2016.02.096. [PMID: 26948630]
  • Kátia Wolff Cordeiro, Josyelen Lousada Felipe, Kauê Franco Malange, Pâmela Rafaela do Prado, Patrícia de Oliveira Figueiredo, Fernanda Rodrigues Garcez, Karine de Cássia Freitas, Walmir Silva Garcez, Mônica Cristina Toffoli-Kadri. Anti-inflammatory and antinociceptive activities of Croton urucurana Baillon bark. Journal of ethnopharmacology. 2016 May; 183(?):128-135. doi: 10.1016/j.jep.2016.02.051. [PMID: 26944237]
  • Saleem Mushtaq, Mushtaq A Aga, Parvaiz H Qazi, Md Niamat Ali, Aabid Manzoor Shah, Sajad Ahmad Lone, Aiyatullah Shah, Aehtesham Hussain, Faheem Rasool, Hafizullah Dar, Zeeshan Hamid Shah, Shabir H Lone. Isolation, characterization and HPLC quantification of compounds from Aquilegia fragrans Benth: Their in vitro antibacterial activities against bovine mastitis pathogens. Journal of ethnopharmacology. 2016 Feb; 178(?):9-12. doi: 10.1016/j.jep.2015.11.039. [PMID: 26631757]
  • Raphael N Alolga, Yong Fan, Gang Zhang, Jin Li, Yi-Jing Zhao, Jimmy Lelu Kakila, Yan Chen, Ping Li, Lian-Wen Qi. Pharmacokinetics of a multicomponent herbal preparation in healthy Chinese and African volunteers. Scientific reports. 2015 Aug; 5(?):12961. doi: 10.1038/srep12961. [PMID: 26268432]
  • Baojuan Xue, Yuanyuan Zhao, Qing Miao, Peipei Miao, Xiaoyan Yang, Guixia Sun, Jin Su, Jing Ye, Baohong Wei, Yuanyuan Zhang, Yujie Zhang. In vitro and in vivo identification of metabolites of magnoflorine by LC LTQ-Orbitrap MS and its potential pharmacokinetic interaction in Coptidis Rhizoma decoction in rat. Biomedical chromatography : BMC. 2015 Aug; 29(8):1235-48. doi: 10.1002/bmc.3413. [PMID: 25611590]
  • Da-Cheng Hao, Pei-Gen Xiao, Hong-Ying Ma, Yong Peng, Chun-Nian He. Mining chemodiversity from biodiversity: pharmacophylogeny of medicinal plants of Ranunculaceae. Chinese journal of natural medicines. 2015 Jul; 13(7):507-20. doi: 10.1016/s1875-5364(15)30045-5. [PMID: 26233841]
  • Hitoshi Sakumoto, Yumiko Yokota, Gakushi Ishibashi, Shouta Maeda, Chihiro Hoshi, Haruyo Takano, Miki Kobayashi, Tadahiro Yahagi, Soichiro Ijiri, Iwao Sakakibara, Akiyoshi Hara. Sinomenine and magnoflorine, major constituents of Sinomeni caulis et rhizoma, show potent protective effects against membrane damage induced by lysophosphatidylcholine in rat erythrocytes. Journal of natural medicines. 2015 Jul; 69(3):441-8. doi: 10.1007/s11418-015-0907-7. [PMID: 25840917]
  • Awantika Singh, Vikas Bajpai, Sunil Kumar, Kamal Ram Arya, Kulwant Rai Sharma, Brijesh Kumar. Quantitative determination of isoquinoline alkaloids and chlorogenic acid in Berberis species using ultra high performance liquid chromatography with hybrid triple quadrupole linear ion trap mass spectrometry. Journal of separation science. 2015 Jun; 38(12):2007-13. doi: 10.1002/jssc.201500063. [PMID: 25847792]
  • Syed Naseer, Shabir H Lone, Javeed A Lone, Mohd A Khuroo, Khursheed A Bhat. LC-MS guided isolation, quantification and antioxidant evaluation of bioactive principles from Epimedium elatum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 989(?):62-70. doi: 10.1016/j.jchromb.2015.02.046. [PMID: 25804994]
  • Renyi Yan, Shengxian Yu, Hongliang Liu, Zhenzhen Xue, Bin Yang. An HPLC-DAD method for simultaneous quantitative determination of four active hydrophilic compounds in Magnoliae officinalis cortex. Journal of chromatographic science. 2015 Apr; 53(4):598-602. doi: 10.1093/chromsci/bmu091. [PMID: 25085894]
  • Manju Bala, Praveen Kumar Verma, Shiv Awasthi, Neeraj Kumar, Brij Lal, Bikram Singh. Chemical prospection of important ayurvedic plant Tinospora cordifolia by UPLC-DAD-ESI-QTOF-MS/MS and NMR. Natural product communications. 2015 Jan; 10(1):43-8. doi: . [PMID: 25920217]
  • Huawei Zhang, Peng Fu, Beilei Ke, Shuping Wang, Min Li, Lin Han, Chengcheng Peng, Weidong Zhang, Runhui Liu. Metabolomic analysis of biochemical changes in the plasma and urine of collagen-induced arthritis in rats after treatment with Huang-Lian-Jie-Du-Tang. Journal of ethnopharmacology. 2014 May; 154(1):55-64. doi: 10.1016/j.jep.2014.03.007. [PMID: 24709313]
  • Jing Liao, Yu Lei, Jian-Zhong Wang. [Chemical constituents of Cocculus orbiculatus var. mollis root]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Feb; 37(2):254-7. doi: ". [PMID: 25095346]
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  • Xiaoting Tian, Zhixiong Li, Yunfei Lin, Mingcang Chen, Guoyu Pan, Chenggang Huang. Study on the PK profiles of magnoflorine and its potential interaction in Cortex phellodendri decoction by LC-MS/MS. Analytical and bioanalytical chemistry. 2014 Jan; 406(3):841-9. doi: 10.1007/s00216-013-7530-9. [PMID: 24337185]
  • Won Il Kim, Bing Tian Zhao, Hai Yan Zhang, Je Hyun Lee, Jong Keun Son, Mi Hee Woo. Quantitative and pattern recognition analyses of magnoflorine, spinosin, 6'''-feruloyl spinosin and jujuboside A by HPLC in Zizyphi Semen. Archives of pharmacal research. 2014; 37(9):1139-47. doi: 10.1007/s12272-013-0295-z. [PMID: 24310099]
  • June Bryan I de la Peña, Hye Lim Lee, Seo Young Yoon, Gun Hee Kim, Yong Soo Lee, Jae Hoon Cheong. The involvement of magnoflorine in the sedative and anxiolytic effects of Sinomeni Caulis et Rhizoma in mice. Journal of natural medicines. 2013 Oct; 67(4):814-21. doi: 10.1007/s11418-013-0754-3. [PMID: 23456265]
  • Mayurkumar B Patel, Shrihari Mishra. Isoquinoline alkaloids from Tinospora cordifolia inhibit rat lens aldose reductase. Phytotherapy research : PTR. 2012 Sep; 26(9):1342-7. doi: 10.1002/ptr.3721. [PMID: 22294283]
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  • Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Zulfiqar Ali, Troy J Smillie, Ikhlas A Khan. Analytical methods for determination of magnoflorine and saponins from roots of Caulophyllum thalictroides (L.) Michx. using UPLC, HPLC and HPTLC. Journal of pharmaceutical and biomedical analysis. 2011 Dec; 56(5):895-903. doi: 10.1016/j.jpba.2011.07.028. [PMID: 21872415]
  • Min Gao, Changzhen Fu, Jingjing Liu, Baolin Guo, Xiangbo Yang, Debin Chen, Li Li. [Distribution and influencing factors of magnoflorine in Epimedium]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Sep; 36(18):2475-8. doi: 10.4268/cjcmm20111805. [PMID: 22256748]
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  • Min Gao, Jingjing Liu, Xinguang Sun, Wenhua Huang, Baolin Guo, Peigen Xiao. [The HPLC determination of the content of magnoflorine in main species of Epimedii Herba]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jan; 36(1):16-8. doi: ". [PMID: 21473145]
  • Tomoko Sano, Ikue Matsumura, Rie Nakamura, Hiroki Yamaji, Kazunori Hashimoto, Osami Takeda, Fumiyuki Kiuchi, Tadahiro Takeda. Genetic and chemical comparison of Boi (Sinomeni Caulis et Rhizoma) and Seifuto (Caulis Sinomenii). Journal of natural medicines. 2010 Jul; 64(3):257-65. doi: 10.1007/s11418-010-0397-6. [PMID: 20217263]
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