Indirubin (BioDeep_00000229852)
Secondary id: BioDeep_00000170060
natural product PANOMIX_OTCML-2023 Antitumor activity
代谢物信息卡片
(Z)-[2,3 inverted exclamation mark -Biindolinylidene]-2 inverted exclamation mark ,3-dione
化学式: C16H10N2O2 (262.074224)
中文名称: 靛玉红
谱图信息:
最多检出来源 Viridiplantae(plant) 51.92%
分子结构信息
SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,18,20H
描述信息
A member of the class of indolones that is 1,3-dihydro-2H-indol-2-one substituted by a 3-oxo-1,3-dihydro-2H-indol-2-ylidene group at position 3. It is the active component of Dang Gui Long Hui Wan, which has been used in traditional Chinese medicine to treat inflammatory diseases and chronic myeloid leukemia.
Indirubin is under investigation in clinical trial NCT01735864 (Dosage Determination Trial for Indigo Naturalis Extract in Oil Ointment).
Indirubin is a natural product found in Isatis tinctoria, Couroupita guianensis, and Calanthe discolor with data available.
D000970 - Antineoplastic Agents
D004396 - Coloring Agents
Indirubin (Couroupitine B) is a bis-indole alkaloid and has emarkable anticancer activity against chronic myelocytic leukemia[1][2].
Indirubin (Couroupitine B) is a bis-indole alkaloid and has emarkable anticancer activity against chronic myelocytic leukemia[1][2].
同义名列表
61 个代谢物同义名
Indirubin; (Z)-[2,3 inverted exclamation mark -Biindolinylidene]-2 inverted exclamation mark ,3-dione; (Z)-[2,3invertedexclamationmark-Biindolinylidene]-2invertedexclamationmark,3-dione; 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3E)-; (3E)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indo l-2-one; 2-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]-2,3-dihydro-1H-indol-3-one; (3E)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one; (3z)-3-(3-oxo-1,3-dihydro-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-one; (3Z)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one; 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-; 2H-Indol-2-one,3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-; 3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-one; 3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-on; 2H-Indol-2-one,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-; 3-(3-oxidanylidene-1H-indol-2-ylidene)-1H-indol-2-one; (3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one; (3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one; 5-24-08-00507 (Beilstein Handbook Reference); 2-(2-oxo-1H-indol-3-ylidene)-1H-indol-3-one; 3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one; [2,3'-Biindolinylidene]-2',3-dione; 3-(3-indolinone-2-ylidene)-indolin-2-one; 3-(3-oxoindolin-2-ylidene)indolin-2-one; 2-(2-hydroxy-1H-indol-3-yl)indol-3-one; (delta(sup 2,3)-BIINDOLINE)-2,3-DIONE; (Z)-[2,3-biindolinylidene]-2,3-dione; (E)-[2,3-biindolinylidene]-2,3-dione; (Z)-[2,3-Biindolinylidene]-2,3-dione; [2,3-Biindolinylidene]-2,3-dione; (delta2,3-Biindoline)-2,3-dione; (2Z)-Indirubin, >=98\\% (HPLC); JNLNPCNGMHKCKO-UHFFFAOYSA-N; Indirubin derivative, 1; Indirubin 3E-form [MI]; INDIRUBIN [WHO-DD]; [.DELTA.2,3-dione; Indirubin- Bio-X; EM-A05-INDIRUBIN; BiomolKI2_000073; UNII-1LXW6D3W2Z; UNII-V86L8P74GI; Indirubin [MI]; Indigopurpurin; Couroupitine B; Isoindirubine; Indirubin,(S); KBio3_000840; KBio2_003018; KBio3_000839; Isoindirubin; KBio2_000450; Isoindogotin; KBio2_005586; Bio2_000395; INDARUBICIN; Bio2_000875; IDI1_002150; V86L8P74GI; 1LXW6D3W2Z; indigo red; BMK1-G9
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:183083
- ChEBI: CHEBI:92322
- PubChem: 5359405
- PubChem: 10177
- DrugBank: DB12379
- ChEMBL: CHEMBL3185783
- ChEMBL: CHEMBL1276127
- ChEMBL: CHEMBL259664
- ChEMBL: CHEMBL35349
- Wikipedia: Indirubin
- MeSH: indirubin
- ChemIDplus: 0000479414
- KNApSAcK: C00026982
- chemspider: 4477010
- CAS: 906748-38-7
- CAS: 397242-72-7
- CAS: 479-41-4
- MoNA: CCMSLIB00005724317
- medchemexpress: HY-N0117
- PMhub: MS000005722
- MetaboLights: MTBLC183083
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)
6 个相关的物种来源信息
- 673185 - Calanthe discolor:
- 66684 - Couroupita guianensis: 10.1016/S0040-4020(01)96609-8
- 161756 - Isatis tinctoria:
- 33090 - Plants: -
- 33090 - 大青叶: -
- 33090 - 青黛: -
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
- HongXia Chen, Hao Zhou, Changwei Zhang, Wenjun Li, Xingying Xue, ChengZhang Wang. Convenient preparation of indigo from the Ieaves of Baphicacanthus cusia(Nees) Bremek by enzymatic method and its MALDI-TOF-MS and UPLC-Q-TOF/MS analysis.
Enzyme and microbial technology.
2024 Aug; 178(?):110440. doi:
10.1016/j.enzmictec.2024.110440. [PMID: 38574422] - Xiaoting Xu, Reham Taha, Chenghan Chu, Li Xiao, Tao Wang, Xinzhi Wang, Xin Huang, Zhenzhou Jiang, Lixin Sun. Indirubin mediates adverse intestinal reactions in guinea pigs by downregulating the expression of AchE through AhR.
Xenobiotica; the fate of foreign compounds in biological systems.
2024 Feb; 54(2):83-94. doi:
10.1080/00498254.2023.2297745. [PMID: 38164702] - Jiang-Min Zhu, Chen Chen, Min Kong, Ling Zhu, Ya-Lin Li, Jian-Fei Zhang, Zhan-Peng Yu, Shi-Shu Xu, Ling-Yi Kong, Jian-Guang Luo. Discovery and optimization of indirubin derivatives as novel ferroptosis inducers for the treatment of colon cancer.
European journal of medicinal chemistry.
2023 Dec; 261(?):115829. doi:
10.1016/j.ejmech.2023.115829. [PMID: 37801824] - Jin Xie, Qi Huang, Huijuan Xie, Jun Liu, Shimin Tian, Ruiyi Cao, Ming Yang, Junzhi Lin, Li Han, Dingkun Zhang. Hyaluronic acid/inulin-based nanocrystals with an optimized ratio of indigo and indirubin for combined ulcerative colitis therapy via immune and intestinal flora regulation.
International journal of biological macromolecules.
2023 Dec; 252(?):126502. doi:
10.1016/j.ijbiomac.2023.126502. [PMID: 37625742] - Zhe Liu, Jin-Ru Zhang, Yong-Xiang Huang, Xue-Ying Li, Hai-Peng Zhu, Rui-Yi Yang, Song Chen. Transcriptomic analysis reveals the regulatory mechanism underlying the indirubin-mediated amelioration of dextran sulfate sodium-induced colitis in mice.
Pharmaceutical biology.
2023 Dec; 61(1):1082-1093. doi:
10.1080/13880209.2023.2233565. [PMID: 37439220] - Yifei Hou, Huimin Zhang, Yangzhuangzhuang Zhu, Xufeng He, Wen Li, Lin Su, Mingxi Liu, Xi Chen, Fang Shen, Xiao Chen, Wencheng Jiang, Chunpu Zou, Zihang Xu. Targeting upregulation of the immunosuppressive activity of MDSCs with indirubin as a novel strategy to alleviate psoriasis.
International immunopharmacology.
2023 Jul; 123(?):110710. doi:
10.1016/j.intimp.2023.110710. [PMID: 37531829] - Lin Li, Chang Liu, Jing Fu, Yan Wang, Danyang Yang, Bing Peng, Xin Liu, Xuyang Han, Yujiao Meng, Fang Feng, Xueqing Hu, Cong Qi, Yazhuo Wang, Ying Zheng, Ping Li. CD44 targeted indirubin nanocrystal-loaded hyaluronic acid hydrogel for the treatment of psoriasis.
International journal of biological macromolecules.
2023 Jul; 243(?):125239. doi:
10.1016/j.ijbiomac.2023.125239. [PMID: 37295696] - Chunjie Jiang, Lu Qi, Jiang Xue, Yibiao Wang. Indirubin-3'-oxime promotes the efficacy of GnRHa in obese-induced central precocious puberty and maintains normal bone growth and body weight via the ERK-Sp1-KISS-1/GPR54 axis.
Cellular and molecular biology (Noisy-le-Grand, France).
2023 Apr; 69(4):188-194. doi:
10.14715/cmb/2023.69.4.29. [PMID: 37329527] - Jin Xie, Shimin Tian, Jun Liu, Shengjie Huang, Ming Yang, Xiangbo Yang, Runchun Xu, Junzhi Lin, Li Han, Dingkun Zhang. Combination Therapy with Indigo and Indirubin for Ulcerative Colitis via Reinforcing Intestinal Barrier Function.
Oxidative medicine and cellular longevity.
2023; 2023(?):2894695. doi:
10.1155/2023/2894695. [PMID: 36825081] - Mengwei Xu, Rui Peng, Qing Min, Siwen Hui, Xin Chen, Guang Yang, Shuanglin Qin. Bisindole natural products: A vital source for the development of new anticancer drugs.
European journal of medicinal chemistry.
2022 Dec; 243(?):114748. doi:
10.1016/j.ejmech.2022.114748. [PMID: 36170798] - Lin Yang, Xinyun Li, Wei Huang, Xiangshu Rao, Yu Lai. Pharmacological properties of indirubin and its derivatives.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2022 Jul; 151(?):113112. doi:
10.1016/j.biopha.2022.113112. [PMID: 35598366] - Alica Fischle, Rico Schwarz, Franziska Wendt, Marcel Kordt, Robert Ramer, Lars Boeckmann, Martin Hein, Peter Langer, Steffen Emmert, Brigitte Vollmar, Burkhard Hinz. A Sensitive LC-MS/MS Method for the Simultaneous Determination of Two Thia-Analogous Indirubin N-Glycosides and Indirubin-3'-Monoxime in Plasma and Cell Culture Medium.
Molecules (Basel, Switzerland).
2022 May; 27(9):. doi:
10.3390/molecules27093031. [PMID: 35566381] - Guang-Min Yu, Li-Feng Zhou, Xiao-Ming Liu, Bin Liu, Xue-Ying Lai, Chu-Lan Xu, Ming-Yi Long, Yan-Ming Zhu, Ji-De Wang, Ming-Song Li. Therapeutic effect of indirubin-loaded bovine serum albumin nanoparticules on ulcerative colitis.
Biomaterials science.
2022 May; 10(9):2215-2223. doi:
10.1039/d1bm01896e. [PMID: 35322266] - Fan Ping, Yanxia Wang, Xia Shen, Conge Tan, Lin Zhu, Wenwen Xing, Jun Xu. Virtual Screening and Molecular Docking to Study the Mechanism of Chinese Medicines in the Treatment of Coronavirus Infection.
Medical science monitor : international medical journal of experimental and clinical research.
2022 Jan; 28(?):e934102. doi:
10.12659/msm.934102. [PMID: 35075100] - Hezhen Wang, Zhiyuan Wang, Chunyong Wei, Jing Wang, Yingshu Xu, Guohui Bai, Qizheng Yao, Lei Zhang, Yongzheng Chen. Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.
European journal of medicinal chemistry.
2021 Nov; 223(?):113652. doi:
10.1016/j.ejmech.2021.113652. [PMID: 34161865] - Mary Priyanka Udumula, Sureshbabu Mangali, Jaspreet Kalra, Deepika Dasari, Srashti Goyal, Vandana Krishna, Srivarsha Reddy Bollareddy, Dharamrajan Sriram, Arti Dhar, Audesh Bhat. High fructose and streptozotocin induced diabetic impairments are mitigated by Indirubin-3-hydrazone via downregulation of PKR pathway in Wistar rats.
Scientific reports.
2021 06; 11(1):12924. doi:
10.1038/s41598-021-92345-2. [PMID: 34155273] - Jingxia Zhao, Xiangjiang Xie, Tingting Di, Yu Liu, Cong Qi, Zhaoxia Chen, Ping Li, Yan Wang. Indirubin attenuates IL-17A-induced CCL20 expression and production in keratinocytes through repressing TAK1 signaling pathway.
International immunopharmacology.
2021 May; 94(?):107229. doi:
10.1016/j.intimp.2020.107229. [PMID: 33611057] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Zhang Tao, Xiaoqing Zhou, Yan Zhang, Wenfeng Pu, Yi Yang, Fuxia Wei, Qian Zhou, Lin Zhang, Zhonghan Du, Ji Wu. Xi Lei San Attenuates Dextran Sulfate Sodium-Induced Colitis in Rats and TNF-α-Stimulated Colitis in CACO2 Cells: Involvement of the NLRP3 Inflammasome and Autophagy.
Mediators of inflammation.
2021; 2021(?):1610251. doi:
10.1155/2021/1610251. [PMID: 33967625] - Feng-Qin Shi, Peng Lyu, Hao He, Li-Zhen Han, Chang-Yu Liu, Hong-Chao Yan, Chong Wang, Xin-Yi Chen. [Effect of Indirubin and Sheng-Xue-Xiao-Ban Capsule (SXXBC) on Promoting Peripheral Platelet in ITP Model Mice].
Zhongguo shi yan xue ye xue za zhi.
2020 Dec; 28(6):2039-2045. doi:
10.19746/j.cnki.issn.1009-2137.2020.06.040. [PMID: 33283739] - Wei Xu, Libin Zhang, Anthony B Cunningham, Shan Li, Huifu Zhuang, Yuhua Wang, Aizhong Liu. Blue genome: chromosome-scale genome reveals the evolutionary and molecular basis of indigo biosynthesis in Strobilanthes cusia.
The Plant journal : for cell and molecular biology.
2020 11; 104(4):864-879. doi:
10.1111/tpj.14992. [PMID: 32981147] - Anna Czapka, Stefanie König, Carlo Pergola, Christian Grune, Konstantina Vougogiannopoulou, Alexios-Leandros Skaltsounis, Dagmar Fischer, Oliver Werz. The indirubin derivative 6-bromoindirubin-3'-glycerol-oxime ether (6BIGOE) potently modulates inflammatory cytokine and prostaglandin release from human monocytes through GSK-3 interference.
Biochemical pharmacology.
2020 10; 180(?):114170. doi:
10.1016/j.bcp.2020.114170. [PMID: 32710971] - Precil Diego Miranda de Menezes Neves, Bernadete Maria Coelho Ferreira, Sara Mohrbacher, Pedro Renato Chocair, Américo Lourenço Cuvello-Neto. Purple urine bag syndrome: a colourful complication of urinary tract infection.
The Lancet. Infectious diseases.
2020 10; 20(10):1215. doi:
10.1016/s1473-3099(20)30323-6. [PMID: 32979332] - Taisuke Konno, Kenroh Sasaki, Kyoko Kobayashi, Toshihiro Murata. Indirubin promotes adipocyte differentiation and reduces lipid accumulation in 3T3‑L1 cells via peroxisome proliferator‑activated receptor γ activation.
Molecular medicine reports.
2020 03; 21(3):1552-1560. doi:
10.3892/mmr.2020.10946. [PMID: 32016452] - Yasuhito Nobushi, Hiroaki Saito, Shinichi Miyairi, Taketo Uchiyama, Yukinaga Kishikawa. Inhibitory Effects of Indirubin-3'-oxime Derivatives on Lipid Accumulation in 3T3-L1 Cells.
Biological & pharmaceutical bulletin.
2020; 43(3):503-508. doi:
10.1248/bpb.b19-00910. [PMID: 32115509] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Sanhapan Wattanapisit, Apichai Wattanapisit, Anong Meepuakmak, Pornnipa Rakkapan. Purple urine bag syndrome in palliative care.
BMJ supportive & palliative care.
2019 Jun; 9(2):155-157. doi:
10.1136/bmjspcare-2018-001601. [PMID: 30045940] - Kai Shao, Tengkai Wang, Tiantian Li, Aijun Zhang, Meijuan Cai, Guanghui Zhao, Qingsong Fu, Qian Wang, Xinguang Liu, Ming Hou. Indirubin regulates MPL and TNF expression in peripheral blood mononuclear cells from patients with primary immune thrombocytopenia.
Experimental hematology.
2019 05; 73(?):18-24. doi:
10.1016/j.exphem.2019.04.002. [PMID: 31014934] - Najat Aourz, Ann-Sophie K Serruys, Joëlle N Chabwine, Pascal Byenda Balegamire, Tatiana Afrikanova, RuAngelie Edrada-Ebel, Alexander I Grey, Appolinary R Kamuhabwa, Laura Walrave, Camila V Esguerra, Fred van Leuven, Peter A M de Witte, Ilse Smolders, Alexander D Crawford. Identification of GSK-3 as a Potential Therapeutic Entry Point for Epilepsy.
ACS chemical neuroscience.
2019 04; 10(4):1992-2003. doi:
10.1021/acschemneuro.8b00281. [PMID: 30351911] - Huayao Li, Lijuan Liu, Jing Zhuang, Cun Liu, Chao Zhou, Jing Yang, Chundi Gao, Gongxi Liu, Changgang Sun. Deciphering the mechanism of Indirubin and its derivatives in the inhibition of Imatinib resistance using a 'drug target prediction-gene microarray analysis-protein network construction' strategy.
BMC complementary and alternative medicine.
2019 Mar; 19(1):75. doi:
10.1186/s12906-019-2471-2. [PMID: 30909944] - Marwa Y Soltan, Uly Sumarni, Chalid Assaf, Peter Langer, Ulrich Reidel, Jürgen Eberle. Key Role of Reactive Oxygen Species (ROS) in Indirubin Derivative-Induced Cell Death in Cutaneous T-Cell Lymphoma Cells.
International journal of molecular sciences.
2019 Mar; 20(5):. doi:
10.3390/ijms20051158. [PMID: 30866411] - M Soledade C Pedras, Abbas Abdoli, Q Huy To, Chintamani Thapa. Ecological Roles of Tryptanthrin, Indirubin and N-Formylanthranilic Acid in Isatis indigotica: Phytoalexins or Phytoanticipins?.
Chemistry & biodiversity.
2019 Mar; 16(3):e1800579. doi:
10.1002/cbdv.201800579. [PMID: 30557446] - Yajing Zhao, Panpan Han, Lei Liu, Xiaojie Wang, Pengcheng Xu, Haoyi Wang, Tianshu Yu, Yunqi Sun, Lizhen Li, Tao Sun, Xinguang Liu, Hai Zhou, Jihua Qiu, Liang Wang, Jun Peng, Shuqian Xu, Ming Hou. Indirubin modulates CD4+ T-cell homeostasis via PD1/PTEN/AKT signalling pathway in immune thrombocytopenia.
Journal of cellular and molecular medicine.
2019 03; 23(3):1885-1898. doi:
10.1111/jcmm.14089. [PMID: 30609280] - Ali Rahiminejad, Rassoul Dinarvand, Behrooz Johari, Saeedeh Jafari Nodooshan, Ali Rashti, Elham Rismani, Parvin Mahdaviani, Zohreh Saltanatpour, Sajad Rahiminejad, Mozhgan Raigani, Masood Khosravani. Preparation and investigation of indirubin-loaded SLN nanoparticles and their anti-cancer effects on human glioblastoma U87MG cells.
Cell biology international.
2019 Jan; 43(1):2-11. doi:
10.1002/cbin.11037. [PMID: 30080277] - Wenjin Lin, Wei Huang, Shuju Ning, Xiaogui Gong, Qi Ye, Daozhi Wei. Comparative transcriptome analyses revealed differential strategies of roots and leaves from methyl jasmonate treatment Baphicacanthus cusia (Nees) Bremek and differentially expressed genes involved in tryptophan biosynthesis.
PloS one.
2019; 14(3):e0212863. doi:
10.1371/journal.pone.0212863. [PMID: 30865659] - Noelani Kamelamela, Michael Zalesne, Joshua Morimoto, Albert Robbat, Benjamin E Wolfe. Indigo- and indirubin-producing strains of Proteus and Psychrobacter are associated with purple rind defect in a surface-ripened cheese.
Food microbiology.
2018 Dec; 76(?):543-552. doi:
10.1016/j.fm.2018.07.011. [PMID: 30166186] - Meng Pan, Wenxuan Pei, Yixin Yao, Ling Dong, Jianbo Chen. Rapid and Integrated Quality Assessment of Organic-Inorganic Composite Herbs by FTIR Spectroscopy-Global Chemical Fingerprints Identification and Multiple Marker Components Quantification of Indigo Naturalis (Qing Dai).
Molecules (Basel, Switzerland).
2018 Oct; 23(11):. doi:
10.3390/molecules23112743. [PMID: 30352981] - Wenyan Gao, Luding Zhang, Xiaoqian Wang, Li Yu, Changhong Wang, Yang Gong. The combination of indirubin and isatin attenuates dextran sodium sulfate induced ulcerative colitis in mice.
Biochemistry and cell biology = Biochimie et biologie cellulaire.
2018 10; 96(5):636-645. doi:
10.1139/bcb-2018-0041. [PMID: 29671340] - G Gaitanis, P Magiatis, A Velegraki, I D Bassukas. A traditional Chinese remedy points to a natural skin habitat: indirubin (indigo naturalis) for psoriasis and the Malassezia metabolome.
The British journal of dermatology.
2018 09; 179(3):800. doi:
10.1111/bjd.16807. [PMID: 29791716] - Xiang-Jiang Xie, Ting-Ting Di, Yan Wang, Ming-Xing Wang, Yu-Jiao Meng, Yan Lin, Xiao-Long Xu, Ping Li, Jing-Xia Zhao. Indirubin ameliorates imiquimod-induced psoriasis-like skin lesions in mice by inhibiting inflammatory responses mediated by IL-17A-producing γδ T cells.
Molecular immunology.
2018 09; 101(?):386-395. doi:
10.1016/j.molimm.2018.07.011. [PMID: 30064075] - Y K Lin, B H Lee. Does Lindioil (indirubin) treatment affect the composition of Malassezia species on psoriatic skin?.
The British journal of dermatology.
2018 09; 179(3):801. doi:
10.1111/bjd.16810. [PMID: 29791722] - Lakshmi Mohan, Darpan Raghav, Shabeeba M Ashraf, Jomon Sebastian, Krishnan Rathinasamy. Indirubin, a bis-indole alkaloid binds to tubulin and exhibits antimitotic activity against HeLa cells in synergism with vinblastine.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2018 Sep; 105(?):506-517. doi:
10.1016/j.biopha.2018.05.127. [PMID: 29883946] - Y-K Lin, L-C See, Y-H Huang, C-C Chi, R C-Y Hui. Comparison of indirubin concentrations in indigo naturalis ointment for psoriasis treatment: a randomized, double-blind, dosage-controlled trial.
The British journal of dermatology.
2018 01; 178(1):124-131. doi:
10.1111/bjd.15894. [PMID: 28815560] - Lihong Chen, Jinhua Wang, Jianbo Wu, Qiaomei Zheng, Jifen Hu. Indirubin suppresses ovarian cancer cell viabilities through the STAT3 signaling pathway.
Drug design, development and therapy.
2018; 12(?):3335-3342. doi:
10.2147/dddt.s174613. [PMID: 30323565] - Manoela Viar Fogaça, Priscila de Matos Cândido-Bacani, Lucas Milanez Benicio, Lara Martinelli Zapata, Priscilla de Freitas Cardoso, Marcelo Tempesta de Oliveira, Tamara Regina Calvo, Eliana Aparecida Varanda, Wagner Vilegas, Ilce Mara de Syllos Cólus. Effects of indirubin and isatin on cell viability, mutagenicity, genotoxicity and BAX/ERCC1 gene expression.
Pharmaceutical biology.
2017 Dec; 55(1):2005-2014. doi:
10.1080/13880209.2017.1354387. [PMID: 28738722] - Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.
Journal of natural products.
2017 10; 80(10):2602-2608. doi:
10.1021/acs.jnatprod.6b01052. [PMID: 29043803] - J X Chu, Y L Chu. [Indirubin-the fruit of combination of Chinese traditional and Western medicine].
Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi.
2017 Jun; 38(6):559-560. doi:
10.3760/cma.j.issn.0253-2727.2017.06.022. [PMID: 28655108] - Tianjie Qi, Haitao Li, Shuai Li. Indirubin improves antioxidant and anti-inflammatory functions in lipopolysaccharide-challenged mice.
Oncotarget.
2017 May; 8(22):36658-36663. doi:
10.18632/oncotarget.17560. [PMID: 28525368] - Jie Yu, Jiacheng Zheng, Jiajia Lin, Linlu Jin, Rui Yu, Shinghung Mak, Shengquan Hu, Hongya Sun, Xiang Wu, Zaijun Zhang, Mingyuen Lee, Wahkeung Tsim, Wei Su, Wenhua Zhou, Wei Cui, Yifan Han, Qinwen Wang. Indirubin-3-Oxime Prevents H2O2-Induced Neuronal Apoptosis via Concurrently Inhibiting GSK3β and the ERK Pathway.
Cellular and molecular neurobiology.
2017 May; 37(4):655-664. doi:
10.1007/s10571-016-0402-z. [PMID: 27412761] - Wan Aliaa Wan Sulaiman, Fan Kee Hoo, Liyana Najwa Inche Mat. An Intriguing Case of Purple Urine Bag Syndrome.
The American journal of the medical sciences.
2017 May; 353(5):e9. doi:
10.1016/j.amjms.2016.11.022. [PMID: 28502345] - Nicolas Gaboriaud-Kolar, Vasillios Myrianthopoulos, Konstantina Vougogiannopoulou, Panagiotis Gerolymatos, David A Horne, Richard Jove, Emmanuel Mikros, Sangkil Nam, Alexios-Leandros Skaltsounis. Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines.
Journal of natural products.
2016 10; 79(10):2464-2471. doi:
10.1021/acs.jnatprod.6b00285. [PMID: 27726390] - Michael D Burg, Eva P Baerends, Christoffel Hendrik Bell. Unusual Urine Color During Catheterization.
American family physician.
2016 Oct; 94(7):572-574. doi:
NULL. [PMID: 27929213] - Evelyn A Jähne, Chethan Sampath, Veronika Butterweck, Matthias Hamburger, Mouhssin Oufir. Development and full validation of an UPLC-MS/MS method for the quantification of the plant-derived alkaloid indirubin in rat plasma.
Journal of pharmaceutical and biomedical analysis.
2016 Sep; 128(?):247-252. doi:
10.1016/j.jpba.2016.05.018. [PMID: 27281580] - Na Eun Kim, Vivek Gupta, Allison Wagreich. Purple Urine Bag Syndrome. A Case Report.
The Journal of reproductive medicine.
2016 Sep; 61(9-10):513-515. doi:
NULL. [PMID: 30383954] - Wenyan Gao, Yufang Guo, Changhong Wang, Yifan Lin, Li Yu, Tianjiao Sheng, Zhuolin Wu, Yang Gong. Indirubin ameliorates dextran sulfate sodium-induced ulcerative colitis in mice through the inhibition of inflammation and the induction of Foxp3-expressing regulatory T cells.
Acta histochemica.
2016 Jul; 118(6):606-614. doi:
10.1016/j.acthis.2016.06.004. [PMID: 27396532] - Laura McDermott, Raman Madan, Reena Rupani, Daniel Siegel. A Review of Indigo Naturalis as an Alternative Treatment for Nail Psoriasis.
Journal of drugs in dermatology : JDD.
2016 Mar; 15(3):319-23. doi:
". [PMID: 26954317] - Xinlai Cheng, Karl-Heinz Merz. The Role of Indirubins in Inflammation and Associated Tumorigenesis.
Advances in experimental medicine and biology.
2016; 929(?):269-290. doi:
10.1007/978-3-319-41342-6_12. [PMID: 27771929] - Adil Karim, Firas Abed, Ghassan Bachuwa. A unilateral purple urine bag syndrome in a patient with bilateral nephrostomy tubes.
BMJ case reports.
2015 Dec; 2015(?):. doi:
10.1136/bcr-2015-212913. [PMID: 26701992] - Abhinav Sood, Ashhar Ali, Adarsh Bhimraj. The color purple.
Cleveland Clinic journal of medicine.
2015 Nov; 82(11):721-2. doi:
10.3949/ccjm.82a.14119. [PMID: 26540322] - Masaru Ishida, Shuji Mikami, Toshiaki Shinojima, Takeo Kosaka, Ryuichi Mizuno, Eiji Kikuchi, Akira Miyajima, Yasunori Okada, Mototsugu Oya. Activation of aryl hydrocarbon receptor promotes invasion of clear cell renal cell carcinoma and is associated with poor prognosis and cigarette smoke.
International journal of cancer.
2015 Jul; 137(2):299-310. doi:
10.1002/ijc.29398. [PMID: 25523818] - Nicolas Gaboriaud-Kolar, Konstantina Vougogiannopoulou, Alexios-Leandros Skaltsounis. Indirubin derivatives: a patent review (2010 - present).
Expert opinion on therapeutic patents.
2015 May; 25(5):583-93. doi:
10.1517/13543776.2015.1019865. [PMID: 25887337] - Feriyde Çalişkan Tür, Nur Zafer, Nil Hocaoglu. Purple urine bag syndrome.
Emergency medicine journal : EMJ.
2015 May; 32(5):347. doi:
10.1136/emermed-2014-203818. [PMID: 24876154] - Aijun Zhang, Bin Ning, Nianzheng Sun, Jianlu Wei, Xiuli Ju. Indirubin Increases CD4+CD25+Foxp3+ Regulatory T Cells to Prevent Immune Thrombocytopenia in Mice.
PloS one.
2015; 10(11):e0142634. doi:
10.1371/journal.pone.0142634. [PMID: 26571298] - Nasim Heshmati, Xinlai Cheng, Else Dapat, Philip Sassene, Gerhard Eisenbrand, Gert Fricker, Anette Müllertz. In vitro and in vivo evaluations of the performance of an indirubin derivative, formulated in four different self-emulsifying drug delivery systems.
The Journal of pharmacy and pharmacology.
2014 Nov; 66(11):1567-75. doi:
10.1111/jphp.12286. [PMID: 24961657] - Ondřej Hloch, Daša Gladišová, Miroslava Horáčková. [Purple urine bag syndrome - rare but substantial symptom of urinary infection].
Vnitrni lekarstvi.
2014 May; 60(5-6):512-3. doi:
NULL. [PMID: 24974756] - Kai Shing Koh, Vui Heng Chong. Purple urine bag syndrome (PUBS): an unusual and rare manifestation of a common condition.
Annals of the Academy of Medicine, Singapore.
2013 Dec; 42(12):700-1. doi:
NULL. [PMID: 24463836] - Nasim Heshmati, Bjoern Wagner, Xinlai Cheng, Therese Scholz, Manfred Kansy, Gerhard Eisenbrand, Gert Fricker. Physicochemical characterization and in vitro permeation of an indirubin derivative.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2013 Nov; 50(3-4):467-75. doi:
10.1016/j.ejps.2013.08.021. [PMID: 23994641] - Kevin McClay, Baojie Wan, Yuehong Wang, Sanghyun Cho, Jerry Yu, Bernard Santarsiero, Shahila Mehboob, Michael Johnson, Scott Franzblau, Robert Steffan. A novel combinatorial biocatalytic approach for producing antibacterial compounds effective against Mycobacterium tuberculosis (TB).
Applied microbiology and biotechnology.
2013 Aug; 97(16):7151-63. doi:
10.1007/s00253-013-5012-9. [PMID: 23749163] - Ding-Kun Zhang, Jun-Zhi Lin, Jian-Yun Liu, Chun-Feng Qin, Zhi-Ping Guo, Li Han, Ming Yang. [Powder modification technology used for the preparation of the hydrophilic decoction pieces of indigo naturalis and the modification principle].
Yao xue xue bao = Acta pharmaceutica Sinica.
2013 Jul; 48(7):1148-55. doi:
". [PMID: 24133984] - Shao-Ying Ke, Yan-Zhi Ma. [Effects of PEG and NaCl stress on the contents of indigotin and indirubin in Isatis indigotica tetraploids].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2013 Apr; 36(4):525-7. doi:
". [PMID: 24133992] - Mi Hye Kim, You Yeon Choi, Gabsik Yang, Ik-Hyun Cho, Dongwoo Nam, Woong Mo Yang. Indirubin, a purple 3,2- bisindole, inhibited allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model.
Journal of ethnopharmacology.
2013 Jan; 145(1):214-9. doi:
10.1016/j.jep.2012.10.055. [PMID: 23149289] - Hai-tao Lü, Jing Liu, Rui Deng, Ji-ying Song. Preparative isolation and purification of indigo and indirubin from Folium isatidis by high-speed counter-current chromatography.
Phytochemical analysis : PCA.
2012 Nov; 23(6):637-41. doi:
10.1002/pca.2366. [PMID: 22553192] - Qi Zhang, Bo Hong, Lihong Zheng, Xiuhua Wang, Defu Cai. Matrix solid-phase dispersion extraction followed by HPLC-diode array detection method for the determination of major constituents in a traditional Chinese medicine Folium isatidis (Da-qing-ye).
Journal of separation science.
2012 Sep; 35(18):2453-9. doi:
10.1002/jssc.201200422. [PMID: 22997033] - Konstantina Vougogiannopoulou, Alexios-Leandros Skaltsounis. From Tyrian purple to kinase modulators: naturally halogenated indirubins and synthetic analogues.
Planta medica.
2012 Sep; 78(14):1515-28. doi:
10.1055/s-0032-1315261. [PMID: 22972384] - Wan-Ling Hsieh, Yin-Ku Lin, Chi-Neu Tsai, Ta-Min Wang, Tzu-Ya Chen, Jong-Hwei S Pang. Indirubin, an acting component of indigo naturalis, inhibits EGFR activation and EGF-induced CDC25B gene expression in epidermal keratinocytes.
Journal of dermatological science.
2012 Aug; 67(2):140-6. doi:
10.1016/j.jdermsci.2012.05.008. [PMID: 22721997] - Minghua Chen, Lishe Gan, Sheng Lin, Xiaoliang Wang, Li Li, Yuhuan Li, Chenggen Zhu, Yanan Wang, Bingya Jiang, Jiandong Jiang, Yongchun Yang, Jiangong Shi. Alkaloids from the root of Isatis indigotica.
Journal of natural products.
2012 Jun; 75(6):1167-76. doi:
10.1021/np3002833. [PMID: 22694318] - Sangkil Nam, Anna Scuto, Fan Yang, Wenyong Chen, Sungman Park, Hwa-Seung Yoo, Heiko Konig, Ravi Bhatia, Xinlai Cheng, Karl-Heinz Merz, Gerhard Eisenbrand, Richard Jove. Indirubin derivatives induce apoptosis of chronic myelogenous leukemia cells involving inhibition of Stat5 signaling.
Molecular oncology.
2012 Jun; 6(3):276-83. doi:
10.1016/j.molonc.2012.02.002. [PMID: 22387217] - Zhi-Qiang Chen, Ying Liu, Ji-Hui Zhao, Lan Wang, Nian-Ping Feng. Improved oral bioavailability of poorly water-soluble indirubin by a supersaturatable self-microemulsifying drug delivery system.
International journal of nanomedicine.
2012; 7(?):1115-25. doi:
10.2147/ijn.s28761. [PMID: 22403491] - Xiaoli Zhang, Yajuan Song, Yuanyuan Wu, Yanmin Dong, Li Lai, Jing Zhang, Binbin Lu, Fujun Dai, Lijun He, Mingyao Liu, Zhengfang Yi. Indirubin inhibits tumor growth by antitumor angiogenesis via blocking VEGFR2-mediated JAK/STAT3 signaling in endothelial cell.
International journal of cancer.
2011 Nov; 129(10):2502-11. doi:
10.1002/ijc.25909. [PMID: 21207415] - Wenwen Tang, Xinyang Zhang, You He, Xiaojun Jin. [Effect of harvest times on yield and quality of Isatidis Folium in Longzhong semi-arid region].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2011 Apr; 36(8):955-8. doi:
10.4268/cjcmm20110801. [PMID: 21809561] - Anja Berger, Sandra-Annika Quast, Michael Plötz, Martin Hein, Manfred Kunz, Peter Langer, Jürgen Eberle. Sensitization of melanoma cells for death ligand-induced apoptosis by an indirubin derivative--Enhancement of both extrinsic and intrinsic apoptosis pathways.
Biochemical pharmacology.
2011 Jan; 81(1):71-81. doi:
10.1016/j.bcp.2010.09.010. [PMID: 20858462] - L Fernández de Orueta, J Esteban Fernández, G Pérez Caballero, J A Melero Bermejo, R Regajo Gallego, J Martínez Carrilero. Purple urine.
Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia.
2011; 31(4):489-90. doi:
10.3265/nefrologia.pre2011.may.10868. [PMID: 21738253] - Ajit Singh, Nar Singh Chauhan, H V Thulasiram, Vibha Taneja, Rakesh Sharma. Identification of two flavin monooxygenases from an effluent treatment plant sludge metagenomic library.
Bioresource technology.
2010 Nov; 101(21):8481-4. doi:
10.1016/j.biortech.2010.06.025. [PMID: 20591656] - Kannan Ponnusamy, Chelladurai Petchiammal, Ramasamy Mohankumar, Waheeta Hopper. In vitro antifungal activity of indirubin isolated from a South Indian ethnomedicinal plant Wrightia tinctoria R. Br.
Journal of ethnopharmacology.
2010 Oct; 132(1):349-54. doi:
10.1016/j.jep.2010.07.050. [PMID: 20691774] - Zeyu Liu, Zhetong Su, Ming Yang, Wenquan Zou. [United Plackett-Burman and Box-Behnken design to control formation of indirubin in process of preparing indigo naturalis].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2010 Oct; 35(19):2551-5. doi:
10.4268/cjcmm20101911. [PMID: 21174763] - Deepa Alex, In Kei Lam, ZhiXiu Lin, Simon Ming Yuen Lee. Indirubin shows anti-angiogenic activity in an in vivo zebrafish model and an in vitro HUVEC model.
Journal of ethnopharmacology.
2010 Sep; 131(2):242-7. doi:
10.1016/j.jep.2010.05.016. [PMID: 20488232] - Kannan Ponnusamy, Mohankumar Ramasamy, Ignacimuthu Savarimuthu, M Gabriel Paulraj. Indirubin potentiates ciprofloxacin activity in the NorA efflux pump of Staphylococcus aureus.
Scandinavian journal of infectious diseases.
2010 Jul; 42(6-7):500-5. doi:
10.3109/00365541003713630. [PMID: 20380543] - Zhishuang Yin, Weicong Wang, Yuan You, Xueying Song, Binbin Xia, Qiao Wang. [Determination of indirubin in serum by HPLC and its application to pharmacokinetics in rats].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2010 May; 35(9):1148-51. doi:
10.4268/cjcmm20100914. [PMID: 20707071] - Ming Yang, Zeyu Liu, Zhetong Su, Wenquan Zou. [Study on mechanism of precursors transforming into indigo and indirubin in blue-genera plants].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2010 Apr; 35(7):928-31. doi:
10.4268/cjcmm20100728. [PMID: 20575402] - Weir Chiang You, Wen Chuan Lin, Jia Tsz Huang, Chang Chi Hsieh. Indigowood root extract protects hematopoietic cells, reduces tissue damage and modulates inflammatory cytokines after total-body irradiation: does Indirubin play a role in radioprotection?.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Dec; 16(12):1105-11. doi:
10.1016/j.phymed.2009.05.011. [PMID: 19589667] - Soo-Hyun Kim, Soo Jeong Choi, Yong-Chul Kim, Hyo-Jeong Kuh. Anti-tumor activity of noble indirubin derivatives in human solid tumor models in vitro.
Archives of pharmacal research.
2009 Jun; 32(6):915-22. doi:
10.1007/s12272-009-1614-2. [PMID: 19557370] - Yin-Ku Lin, Yann-Lii Leu, Sien-Hung Yang, Hsiao-Wen Chen, Chin-Ting Wang, Jong-Hwei Su Pang. Anti-psoriatic effects of indigo naturalis on the proliferation and differentiation of keratinocytes with indirubin as the active component.
Journal of dermatological science.
2009 Jun; 54(3):168-74. doi:
10.1016/j.jdermsci.2009.02.007. [PMID: 19303259] - B P Pillai, V H Chong, A M Yong. Purple urine bag syndrome.
Singapore medical journal.
2009 May; 50(5):e193-4. doi:
NULL. [PMID: 19495508] - Jianying Hu, Hong Chang, Lezheng Wang, Shimin Wu, Bin Shao, Jun Zhou, Ying Zhao. Detection, occurrence and fate of indirubin in municipal sewage treatment plants.
Environmental science & technology.
2008 Nov; 42(22):8339-44. doi:
10.1021/es801038y. [PMID: 19068815] - Chih-Chung Shiao, Ching-Yi Weng, Jui-Chu Chuang, Mao-Sheng Huang, Zen-Yong Chen. Purple urine bag syndrome: a community-based study and literature review.
Nephrology (Carlton, Vic.).
2008 Oct; 13(7):554-9. doi:
10.1111/j.1440-1797.2008.00978.x. [PMID: 18771468] - Che-Kim Tan, Ya-Ping Wu, Hsing-Ying Wu, Chih-Cheng Lai. Purple urine bag syndrome.
CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne.
2008 Aug; 179(5):491. doi:
10.1503/cmaj.071604. [PMID: 18725621] - X Y Deng, S N Zheng, G H Gao, G Fan, F Li. Determination and pharmacokinetic study of indirubin in rat plasma by high-performance liquid chromatography.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2008 Apr; 15(4):277-83. doi:
10.1016/j.phymed.2008.01.004. [PMID: 18337073] - Lan Wang, Guang-Biao Zhou, Ping Liu, Jun-Hong Song, Yang Liang, Xiao-Jing Yan, Fang Xu, Bing-Shun Wang, Jian-Hua Mao, Zhi-Xiang Shen, Sai-Juan Chen, Zhu Chen. Dissection of mechanisms of Chinese medicinal formula Realgar-Indigo naturalis as an effective treatment for promyelocytic leukemia.
Proceedings of the National Academy of Sciences of the United States of America.
2008 Mar; 105(12):4826-31. doi:
10.1073/pnas.0712365105. [PMID: 18344322] - Chi-Hung Lin, Hsien-Te Huang, Chia-Chang Chien, Dong-Sheng Tzeng, For-Wey Lung. Purple urine bag syndrome in nursing homes: ten elderly case reports and a literature review.
Clinical interventions in aging.
2008; 3(4):729-34. doi:
10.2147/cia.s3534. [PMID: 19281065]