Cryptolepine (BioDeep_00000007194)
Secondary id: BioDeep_00001868909
human metabolite blood metabolite
代谢物信息卡片
5-methyl-5H-indolo[3,2-b]quinoline
化学式: C16H12N2 (232.1000432)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 29.03%
分子结构信息
SMILES: CN1C2=C3C=CC=CC3=NC2=CC2=CC=CC=C12
InChI: InChI=1S/C16H12N2/c1-18-15-9-5-2-6-11(15)10-14-16(18)12-7-3-4-8-13(12)17-14/h2-10H,1H3
描述信息
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
同义名列表
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:3930
- KEGG: C09142
- PubChem: 82143
- HMDB: HMDB0250549
- Metlin: METLIN67463
- ChEMBL: CHEMBL119096
- Wikipedia: Cryptolepine
- KNApSAcK: C00001710
- chemspider: 74137
- CAS: 480-26-2
- PMhub: MS000020487
- PubChem: 11334
- PDB-CCD: DR1
- 3DMET: B02714
- NIKKAJI: J13.757J
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)
4 个相关的物种来源信息
- 1882729 - Cryptolepis sanguinolenta:
- 9606 - Homo sapiens: -
- 233711 - Micropholis guyanensis: 10.1021/NP990035G
- 108357 - Sida acuta: 10.1078/0944711041495245
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
- Jiang Shao, Zhi-Jun Zhang, Yu Shi, Wei-Qi Jiang, Faisal Siddique, Liangye Chen, Genyan Liu, Jiakai Zhu, Xiong-Fei Luo, Ying-Qian Liu, Jun-Xia An, Cheng-Jie Yang, Zi-Ning Cui. Application and Mechanism of Cryptolepine and Neocryptolepine Derivatives as T3SS Inhibitors for Control of Bacterial Leaf Blight on Rice.
Journal of agricultural and food chemistry.
2024 Apr; 72(13):6988-6997. doi:
10.1021/acs.jafc.4c00214. [PMID: 38506764] - Hai-Xin Li, Xiong-Fei Luo, Peng Deng, Shao-Yong Zhang, Han Zhou, Yan Yan Ding, Yi-Rong Wang, Ying-Qian Liu, Zhi-Jun Zhang. Structural Simplification of Cryptolepine to Obtain Novel Antifungal Quinoline Derivatives against Phytopathogenic Fungi.
Journal of agricultural and food chemistry.
2023 Feb; 71(5):2301-2312. doi:
10.1021/acs.jafc.2c07575. [PMID: 36706432] - Champa Keeya Tudu, Anustup Bandyopadhyay, Manoj Kumar, Radha, Tuyelee Das, Samapika Nandy, Mimosa Ghorai, Abilash Valsala Gopalakrishnan, Jarosław Proćków, Abhijit Dey. Unravelling the pharmacological properties of cryptolepine and its derivatives: a mini-review insight.
Naunyn-Schmiedeberg's archives of pharmacology.
2023 02; 396(2):229-238. doi:
10.1007/s00210-022-02302-7. [PMID: 36251044] - Shasank S Swain, Sanghamitra Pati, Tahziba Hussain. Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation.
European journal of medicinal chemistry.
2022 Mar; 232(?):114173. doi:
10.1016/j.ejmech.2022.114173. [PMID: 35168150] - Qing-Ru Chu, Ying-Hui He, Chen Tang, Zhi-Jun Zhang, Xiong-Fei Luo, Bao-Qi Zhang, Yong Zhou, Tian-Lin Wu, Sha-Sha Du, Cheng-Jie Yang, Ying-Qian Liu. Design, Synthesis, and Antimicrobial Activity of Quindoline Derivatives Inspired by the Cryptolepine Alkaloid.
Journal of agricultural and food chemistry.
2022 Mar; 70(9):2851-2863. doi:
10.1021/acs.jafc.1c07536. [PMID: 35226498] - Seth A Domfeh, Patrick W Narkwa, Osbourne Quaye, Kwadwo A Kusi, Bright S Addy, Sian Lant, Rebecca P Sumner, Carlos Maluquer de Motes, Gordon A Awandare, Charles Ansah, Mohamed Mutocheluh. The Pharmacologically Active Alkaloid Cryptolepine Activates a Type 1 Interferon Response That Is Independent of MAVS and STING Pathways.
Journal of immunology research.
2022; 2022(?):8873536. doi:
10.1155/2022/8873536. [PMID: 35928633] - Seth A Domfeh, Patrick W Narkwa, Osbourne Quaye, Kwadwo A Kusi, Gordon A Awandare, Charles Ansah, Alimatu Salam, Mohamed Mutocheluh. Cryptolepine inhibits hepatocellular carcinoma growth through inhibiting interleukin-6/STAT3 signalling.
BMC complementary medicine and therapies.
2021 Jun; 21(1):161. doi:
10.1186/s12906-021-03326-x. [PMID: 34078370] - Priscilla Kolibea Mante, Nana Ofori Adomako, Paulina Antwi, Nana Kofi Kusi-Boadum, Newman Osafo. Solid-lipid nanoparticle formulation improves antiseizure action of cryptolepine.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2021 May; 137(?):111354. doi:
10.1016/j.biopha.2021.111354. [PMID: 33561642] - Yong-Jia Chen, Hua Liu, Shao-Yong Zhang, Hu Li, Kun-Yuan Ma, Ying-Qian Liu, Xiao-Dan Yin, Rui Zhou, Yin-Fang Yan, Ren-Xuan Wang, Ying-Hui He, Qing-Ru Chu, Chen Tang. Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi.
Journal of agricultural and food chemistry.
2021 Feb; 69(4):1259-1271. doi:
10.1021/acs.jafc.0c06480. [PMID: 33496176] - Gaber El-Saber Batiha, Amany Magdy Beshbishy, Luay M Alkazmi, Eman H Nadwa, Eman K Rashwan, Naoaki Yokoyama, Ikuo Igarashi. In vitro and in vivo growth inhibitory activities of cryptolepine hydrate against several Babesia species and Theileria equi.
PLoS neglected tropical diseases.
2020 08; 14(8):e0008489. doi:
10.1371/journal.pntd.0008489. [PMID: 32853247] - Vijay K Nuthakki, Ramesh Mudududdla, Ankita Sharma, Ajay Kumar, Sandip B Bharate. Synthesis and biological evaluation of indoloquinoline alkaloid cryptolepine and its bromo-derivative as dual cholinesterase inhibitors.
Bioorganic chemistry.
2019 09; 90(?):103062. doi:
10.1016/j.bioorg.2019.103062. [PMID: 31220673] - Elvis O Ameyaw, Kodwo B Asmah, Robert P Biney, Isaac T Henneh, Phyllis Owusu-Agyei, James Prah, Arnold D Forkuo. Isobolographic analysis of co-administration of two plant-derived antiplasmodial drug candidates, cryptolepine and xylopic acid, in Plasmodium berghei.
Malaria journal.
2018 Apr; 17(1):153. doi:
10.1186/s12936-018-2283-8. [PMID: 29618354] - Arnold Donkor Forkuo, Charles Ansah, Kwesi Boadu Mensah, Kofi Annan, Ben Gyan, Anjo Theron, Dalu Mancama, Colin W Wright. In vitro anti-malarial interaction and gametocytocidal activity of cryptolepine.
Malaria journal.
2017 12; 16(1):496. doi:
10.1186/s12936-017-2142-z. [PMID: 29282057] - Arnold Donkor Forkuo, Charles Ansah, David Pearson, Werner Gertsch, Amanda Cirello, Adam Amaral, Jaimie Spear, Colin W Wright, Caroline Rynn. Identification of cryptolepine metabolites in rat and human hepatocytes and metabolism and pharmacokinetics of cryptolepine in Sprague Dawley rats.
BMC pharmacology & toxicology.
2017 12; 18(1):84. doi:
10.1186/s40360-017-0188-8. [PMID: 29273084] - Navriti Chadha, Om Silakari. Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
European journal of medicinal chemistry.
2017 Jul; 134(?):159-184. doi:
10.1016/j.ejmech.2017.04.003. [PMID: 28412530] - Harish C Pal, Santosh K Katiyar. Cryptolepine, a Plant Alkaloid, Inhibits the Growth of Non-Melanoma Skin Cancer Cells through Inhibition of Topoisomerase and Induction of DNA Damage.
Molecules (Basel, Switzerland).
2016 Dec; 21(12):. doi:
10.3390/molecules21121758. [PMID: 28009843] - Arnold D Forkuo, Charles Ansah, Kwesi M Boadu, Johnson N Boampong, Elvis O Ameyaw, Ben A Gyan, Andrea T Arku, Michael F Ofori. Synergistic anti-malarial action of cryptolepine and artemisinins.
Malaria journal.
2016 Feb; 15(?):89. doi:
10.1186/s12936-016-1137-5. [PMID: 26879905] - Arnab Chatterjee, Satyanshu Kumar, Sunil K Chattopadhyay. A validated HPLC-PDA method for identification and quantification of two bioactive alkaloids, ephedrine and cryptolepine, in different Sida species.
Biomedical chromatography : BMC.
2013 Dec; 27(12):1720-5. doi:
10.1002/bmc.2985. [PMID: 23881514] - C Ansah, K B Mensah. A review of the anticancer potential of the antimalarial herbal cryptolepis sanguinolenta and its major alkaloid cryptolepine.
Ghana medical journal.
2013 Sep; 47(3):137-47. doi:
. [PMID: 24391229] - N Kuntworbe, M Ofori, P Addo, M Tingle, R Al-Kassas. Pharmacokinetics and in vivo chemosuppressive activity studies on cryptolepine hydrochloride and cryptolepine hydrochloride-loaded gelatine nanoformulation designed for parenteral administration for the treatment of malaria.
Acta tropica.
2013 Sep; 127(3):165-73. doi:
10.1016/j.actatropica.2013.04.010. [PMID: 23643517] - Olumayokun A Olajide, Harsharan S Bhatia, Antonio C P de Oliveira, Colin W Wright, Bernd L Fiebich. Anti-neuroinflammatory properties of synthetic cryptolepine in human neuroblastoma cells: possible involvement of NF-κB and p38 MAPK inhibition.
European journal of medicinal chemistry.
2013 May; 63(?):333-9. doi:
10.1016/j.ejmech.2013.02.004. [PMID: 23507189] - L F Rocha e Silva, A Montoia, R C N Amorim, M R Melo, M C Henrique, S M Nunomura, M R F Costa, V F Andrade Neto, D S Costa, G Dantas, J Lavrado, R Moreira, A Paulo, A C Pinto, W P Tadei, R S Zacardi, M N Eberlin, A M Pohlit. Comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Dec; 20(1):71-6. doi:
10.1016/j.phymed.2012.09.008. [PMID: 23092722] - Sudipta Hazra, Subhalakshmi Ghosh, Sukalyani Debnath, Scott Seville, Vijay Kumar Prajapati, Colin W Wright, Shyam Sundar, Banasri Hazra. Antileishmanial activity of cryptolepine analogues and apoptotic effects of 2,7-dibromocryptolepine against Leishmania donovani promastigotes.
Parasitology research.
2012 Jul; 111(1):195-203. doi:
10.1007/s00436-012-2818-9. [PMID: 22297912] - J Godfrey P Stell, Richard T Wheelhouse, Colin W Wright. Metabolism of cryptolepine and 2-fluorocryptolepine by aldehyde oxidase.
The Journal of pharmacy and pharmacology.
2012 Feb; 64(2):237-43. doi:
10.1111/j.2042-7158.2011.01408.x. [PMID: 22221099] - Rajendran C Gopalan, Esra Emerce, Colin W Wright, Bensu Karahalil, Ali E Karakaya, Diana Anderson. Effects of the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm in the Comet assay.
Toxicology letters.
2011 Dec; 207(3):322-5. doi:
10.1016/j.toxlet.2011.09.010. [PMID: 21946165] - Olumayokun A Olajide, Abayomi M Ajayi, Colin W Wright. Anti-inflammatory properties of cryptolepine.
Phytotherapy research : PTR.
2009 Oct; 23(10):1421-5. doi:
10.1002/ptr.2794. [PMID: 19288476] - Daniel Laryea, Anders Isaksson, Colin W Wright, Rolf Larsson, Peter Nygren. Characterization of the cytotoxic activity of the indoloquinoline alkaloid cryptolepine in human tumour cell lines and primary cultures of tumour cells from patients.
Investigational new drugs.
2009 Oct; 27(5):402-11. doi:
10.1007/s10637-008-9185-5. [PMID: 18853102] - Kirandeep Kaur, Meenakshi Jain, Tarandeep Kaur, Rahul Jain. Antimalarials from nature.
Bioorganic & medicinal chemistry.
2009 May; 17(9):3229-56. doi:
10.1016/j.bmc.2009.02.050. [PMID: 19299148] - Taka-aki Matsui, Yoshihiro Sowa, Hiroaki Murata, Koichi Takagi, Ryoko Nakanishi, Shunji Aoki, Masayuki Yoshikawa, Motomasa Kobayashi, Tomoya Sakabe, Toshikazu Kubo, Toshiyuki Sakai. The plant alkaloid cryptolepine induces p21WAF1/CIP1 and cell cycle arrest in a human osteosarcoma cell line.
International journal of oncology.
2007 Oct; 31(4):915-22. doi:
. [PMID: 17786325] - Colin W Wright. Recent developments in naturally derived antimalarials: cryptolepine analogues.
The Journal of pharmacy and pharmacology.
2007 Jun; 59(6):899-904. doi:
10.1211/jpp.59.6.0017. [PMID: 17637183] - Ji-feng Liu, Xue-mei Zhang, Duo-qing Xue, Zhi-yong Jiang, Qiong Gu, Ji-jun Chen. [Studies on chemical constituents from leaves of Isatis indigotica].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2006 Dec; 31(23):1961-5. doi:
. [PMID: 17348190] - Sabine Van Miert, Steven Hostyn, Bert U W Maes, Kanyanga Cimanga, Reto Brun, Marcel Kaiser, Péter Mátyus, Roger Dommisse, Guy Lemière, Arnold Vlietinck, Luc Pieters. Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound.
Journal of natural products.
2005 May; 68(5):674-7. doi:
10.1021/np0496284. [PMID: 15921407] - Charles Ansah, Ayesha Khan, Nigel J Gooderham. In vitro genotoxicity of the West African anti-malarial herbal Cryptolepis sanguinolenta and its major alkaloid cryptolepine.
Toxicology.
2005 Mar; 208(1):141-7. doi:
10.1016/j.tox.2004.11.026. [PMID: 15664441] - Simon Gibbons, Fatemeh Fallah, Colin W Wright. Cryptolepine hydrochloride: a potent antimycobacterial alkaloid derived from Cryptolepis sanguinolenta.
Phytotherapy research : PTR.
2003 Apr; 17(4):434-6. doi:
10.1002/ptr.1284. [PMID: 12722159] - L Dassonneville, A Lansiaux, A Wattelet, N Wattez, C Mahieu, S Van Miert, L Pieters, C Bailly. Cytotoxicity and cell cycle effects of the plant alkaloids cryptolepine and neocryptolepine: relation to drug-induced apoptosis.
European journal of pharmacology.
2000 Dec; 409(1):9-18. doi:
10.1016/s0014-2999(00)00805-0. [PMID: 11099695] - C Bailly, W Laine, B Baldeyrou, M C De Pauw-Gillet, P Colson, C Houssier, K Cimanga, S Van Miert, A J Vlietinck, L Pieters. DNA intercalation, topoisomerase II inhibition and cytotoxic activity of the plant alkaloid neocryptolepine.
Anti-cancer drug design.
2000 Jun; 15(3):191-201. doi:
. [PMID: 11049087] - L Dassonneville, K Bonjean, M C De Pauw-Gillet, P Colson, C Houssier, J Quetin-Leclercq, L Angenot, C Bailly. Stimulation of topoisomerase II-mediated DNA cleavage by three DNA-intercalating plant alkaloids: cryptolepine, matadine, and serpentine.
Biochemistry.
1999 Jun; 38(24):7719-26. doi:
10.1021/bi990094t. [PMID: 10387011] - J Luo, D M Fort, T J Carlson, B K Noamesi, D nii-Amon-Kotei, S R King, J Tsai, J Quan, C Hobensack, P Lapresca, N Waldeck, C D Mendez, S D Jolad, D E Bierer, G M Reaven. Cryptolepis sanguinolenta: an ethnobotanical approach to drug discovery and the isolation of a potentially useful new antihyperglycaemic agent.
Diabetic medicine : a journal of the British Diabetic Association.
1998 May; 15(5):367-74. doi:
10.1002/(sici)1096-9136(199805)15:5<367::aid-dia576>3.0.co;2-g. [PMID: 9609357] - D E Bierer, D M Fort, C D Mendez, J Luo, P A Imbach, L G Dubenko, S D Jolad, R E Gerber, J Litvak, Q Lu, P Zhang, M J Reed, N Waldeck, R C Bruening, B K Noamesi, R F Hector, T J Carlson, S R King. Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine: its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities.
Journal of medicinal chemistry.
1998 Mar; 41(6):894-901. doi:
10.1021/jm9704816. [PMID: 9526563] - A O Oyekan. Cryptolepine-induced vasodilation in the isolated perfused kidney of the rat: role of G-proteins, K+ and Ca2+ channels.
European journal of pharmacology.
1995 Oct; 285(1):1-9. doi:
10.1016/0014-2999(95)00289-w. [PMID: 8846804] - A O Oyekan. Role of the endothelium and cyclic GMP in renal vasodilator responses to cryptolepine in rats.
Journal of cardiovascular pharmacology.
1994 Apr; 23(4):602-11. doi:
10.1097/00005344-199404000-00012. [PMID: 7516010] - Q Salako, S Y Ablordeppey, D Dwuma-Badu, J R Thornback. Radioiodination and preliminary in vivo investigation of the alkaloid cryptolepine.
The International journal of applied radiation and isotopes.
1985 Dec; 36(12):1003-4. doi:
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