Cinchonidine (BioDeep_00000016573)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(R)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(QUINOLIN-4-YL)METHANOL [WHO-IP]

化学式: C19H22N2O (294.1732042)
中文名称: 辛可宁, 辛可尼定
谱图信息: 最多检出来源 Viridiplantae(plant) 7.45%

分子结构信息

SMILES: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2

描述信息

Cinchonidine is 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis. It has a role as a metabolite. It is a cinchona alkaloid and an (8xi)-cinchonan-9-ol. It derives from a hydride of an (8S)-cinchonan.
Cinchonidine is a natural product found in Cinchona calisaya, Cinchona officinalis, and other organisms with data available.
8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
Origin: Plant; SubCategory_DNP: Alkaloids derived from anthranilic acid, Quinoline alkaloids
Annotation level-1
[Raw Data] CBA34_Cinchonidine_pos_50eV_1-2_01_1626.txt
[Raw Data] CBA34_Cinchonidine_pos_40eV_1-2_01_1625.txt
[Raw Data] CBA34_Cinchonidine_pos_20eV_1-2_01_1623.txt
[Raw Data] CBA34_Cinchonidine_pos_30eV_1-2_01_1624.txt
[Raw Data] CBA34_Cinchonidine_pos_10eV_1-2_01_1617.txt
Cinchonidine (α-Quinidine) is a cinchona alkaloid found in Cinchona officinalis and Gongronema latifolium. A building block used in asymmetric synthesis in organic chemistry. Weak inhibitor of serotonin transporter (SERT) with Kis of 330, 4.2, 36, 196, 15 μM for dSERT, hSERT, hSERT I172M, hSERT S438T, hSERT Y95F, respectively. Antimalarial activities[1].
Cinchonidine (α-Quinidine) is a cinchona alkaloid found in Cinchona officinalis and Gongronema latifolium. A building block used in asymmetric synthesis in organic chemistry. Weak inhibitor of serotonin transporter (SERT) with Kis of 330, 4.2, 36, 196, 15 μM for dSERT, hSERT, hSERT I172M, hSERT S438T, hSERT Y95F, respectively. Antimalarial activities[1].
Cinchonine is a natural compound present in Cinchona bark. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells[1].
Cinchonine is a natural compound present in Cinchona bark. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells[1].

同义名列表

72 个代谢物同义名

(R)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(QUINOLIN-4-YL)METHANOL [WHO-IP]; (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol; (R)-[(4S,5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-quinolin-4-ylmethanol; (S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol; (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol; (R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (-)-Cinchonidine, 99\\% (total base), may cont. up to 5\\% quinine; (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (R)-4-quinolyl-[(2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol; cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer; Cinchonidine, purum, >=98.0\\% (dried material, NT); QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]; 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-; QUININE HYDROCHLORIDE IMPURITY B [EP IMPURITY]; QUININE SULFATE IMPURITY B [EP IMPURITY]; (-)-Cinchonidine, analytical standard; QUININE BISULFATE IMPURITY B [WHO-IP]; QUININE SULFATE IMPURITY B [WHO-IP]; Cinchonan-9-ol, (8.alpha.,9R)-; cinchonidine monohydrochloride; Cinchonan-9-ol, (8a alpha,9R)-; Cinchonan-9-ol, (8-alpha,9R)-; Cinchonan-9-ol, (8alpha,9R)-; KMPWYEUPVWOPIM-KODHJQJWSA-N; (8-alpha,9R)-Cinchonan-9-ol; (8alpha,9R)-Cinchonan-9-ol; cinchonidine hydrochloride; cinchonidine sulfate(2:1); (8alpha,9R)Cinchonan-9-ol; Cinchonan-9-ol, (8a,9R)-; (8S,9R)-cinchonan-9-ol; CINCHONIDINE [WHO-IP]; Cinchonan-9-ol, (9S)-; CINCHONIDINE [WHO-DD]; (8S,9R)-Cinchonidine; Cinchonidine, 96\\%; .alpha.-Quinidine; CINCHONIDINE [MI]; Prestwick3_000606; Spectrum4_001173; (-)-Cinchonidine; Spectrum3_001745; Cinchonidine,(S); Spectrum2_000719; (-) cinchonidine; Spectrum5_002073; UNII-1U622LRA8Z; alpha-Quinidine; (-)cinchonidine; L-Cinchonidine; Cinchovatine-; BPBio1_000564; DivK1c_000501; KBio2_006781; Cinchovatine; KBio2_004213; Prestwick_66; |A-Quinidine; KBio1_000501; KBio2_001645; KBio3_002670; Cinchonidine; a-quinidine; IDI1_000501; 1U622LRA8Z; -Quinidine; Cinchonine; AI3-15317; α-Quinidine; (8R,9S)-Cinchonine; LA40221



数据库引用编号

63 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

29 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

  • Feng Liang, Ying Lv, Xiao Qiao, Shu Zhang, Shanshan Shen, Changcheng Wang, Guifang Xu, Xiaoping Zou, Lei Wang, Bin Zhang. Cinchonine-induced cell death in pancreatic cancer cells by downregulating RRP15. Cell biology international. 2023 Jan; ?(?):. doi: 10.1002/cbin.11987. [PMID: 36682038]
  • Zhi-Ping Che, Jin-Ming Yang, Song Zhang, Di Sun, Yue-E Tian, Sheng-Ming Liu, Xiao-Min Lin, Jia Jiang, Gen-Qiang Chen. Synthesis of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents. Journal of Asian natural products research. 2021 Feb; 23(2):163-175. doi: 10.1080/10286020.2020.1729136. [PMID: 32091234]
  • Nataly Allasi Canales, Tobias Nikolaj Gress Hansen, Claus Cornett, Kim Walker, Felix Driver, Alexandre Antonelli, Carla Maldonado, Mark Nesbitt, Christopher J Barnes, Nina Rønsted. Historical chemical annotations of Cinchona bark collections are comparable to results from current day high-pressure liquid chromatography technologies. Journal of ethnopharmacology. 2020 Mar; 249(?):112375. doi: 10.1016/j.jep.2019.112375. [PMID: 31698039]
  • Wentao Liu, Wenfang Qin, Xiaobei Wang, Fei Xue, Xiao-Yu Liu, Yong Qin. Bioinspired Synthesis of (+)-Cinchonidine Using Cascade Reactions. Angewandte Chemie (International ed. in English). 2018 09; 57(38):12299-12302. doi: 10.1002/anie.201804848. [PMID: 30084528]
  • Adele Murauer, Markus Ganzera. Quantitative determination of major alkaloids in Cinchona bark by Supercritical Fluid Chromatography. Journal of chromatography. A. 2018 Jun; 1554(?):117-122. doi: 10.1016/j.chroma.2018.04.038. [PMID: 29699870]
  • Tian Zhang, Daojin Li. Influences of urea and pH on the interaction of cinchonidine with bovine serum albumin by steady state fluorescence spectroscopy. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Aug; 112(?):15-20. doi: 10.1016/j.saa.2013.04.032. [PMID: 23651774]
  • Ichiro Hisaki, Eri Hiraishi, Toshiyuki Sasaki, Hideo Orita, Seiji Tsuzuki, Norimitsu Tohnai, Mikiji Miyata. Crystal structure of quinine: the effects of vinyl and methoxy groups on molecular assemblies of Cinchona alkaloids cannot be ignored. Chemistry, an Asian journal. 2012 Nov; 7(11):2607-14. doi: 10.1002/asia.201200566. [PMID: 22915374]
  • Nicholas G Spiropulos, Jennifer M Heemstra. Templating effect in DNA proximity ligation enables use of non-bioorthogonal chemistry in biological fluids. Artificial DNA, PNA & XNA. 2012 Jul; 3(3):123-8. doi: 10.4161/adna.23842. [PMID: 23370267]
  • Shoji Maehara, Partomuan Simanjuntak, Chinami Kitamura, Kazuyoshi Ohashi, Hirotaka Shibuya. Bioproduction of Cinchona alkaloids by the endophytic fungus Diaporthe sp. associated with Cinchona ledgeriana. Chemical & pharmaceutical bulletin. 2012; 60(10):1301-4. doi: 10.1248/cpb.c12-00545. [PMID: 22863799]
  • Mohammed Rahmatullah, Shahadat Hossan, Afsana Khatun, Syeda Seraj, Rownak Jahan. Medicinal plants used by various tribes of bangladesh for treatment of malaria. Malaria research and treatment. 2012; 2012(?):371798. doi: 10.1155/2012/371798. [PMID: 22315700]
  • Sung A Jung, Miseon Choi, Sohee Kim, Rina Yu, Taesun Park. Cinchonine Prevents High-Fat-Diet-Induced Obesity through Downregulation of Adipogenesis and Adipose Inflammation. PPAR research. 2012; 2012(?):541204. doi: 10.1155/2012/541204. [PMID: 22675336]
  • S Vargas, K Ndjoko Ioset, A-E Hay, J-R Ioset, S Wittlin, K Hostettmann. Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. Journal of pharmaceutical and biomedical analysis. 2011 Dec; 56(5):880-6. doi: 10.1016/j.jpba.2011.06.026. [PMID: 21872416]
  • Timothy N C Wells. Natural products as starting points for future anti-malarial therapies: going back to our roots?. Malaria journal. 2011 Mar; 10 Suppl 1(?):S3. doi: 10.1186/1475-2875-10-s1-s3. [PMID: 21411014]
  • Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
  • Sarfraz A Nawaz, Muhammad Ayaz, Wolfgang Brandt, Ludger A Wessjohann, Bernhard Westermann. Cation-π and π-π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids. Biochemical and biophysical research communications. 2011 Jan; 404(4):935-40. doi: 10.1016/j.bbrc.2010.12.084. [PMID: 21185266]
  • Anne-Sylvie Fabiano-Tixier, Abdelhakim Elomri, Axelle Blanckaert, Elisabeth Seguin, Emmanuel Petitcolas, Farid Chemat. Rapid and green analytical method for the determination of quinoline alkaloids from Cinchona succirubra based on Microwave-Integrated Extraction and Leaching (MIEL) prior to high performance liquid chromatography. International journal of molecular sciences. 2011; 12(11):7846-60. doi: 10.3390/ijms12117846. [PMID: 22174637]
  • Shoji Maehara, Partomuan Simanjuntak, Chinami Kitamura, Kazuyoshi Ohashi, Hirotaka Shibuya. Cinchona alkaloids are also produced by an endophytic filamentous fungus living in cinchona plant. Chemical & pharmaceutical bulletin. 2011; 59(8):1073-4. doi: 10.1248/cpb.59.1073. [PMID: 21804259]
  • Pratik Chakrabarti. Empire and alternatives: Swietenia febrifuga and the Cinchona substitutes. Medical history. 2010 Jan; 54(1):75-94. doi: 10.1017/s0025727300004324. [PMID: 20046265]
  • Xue-jun Kang, Li-qin Chen, Yi-yun Zhang, Yang-wei Liu, Zhong-ze Gu. Performance of electrospun nanofibers for SPE of drugs from aqueous solutions. Journal of separation science. 2008 Oct; 31(18):3272-8. doi: 10.1002/jssc.200800285. [PMID: 18773420]
  • Eric Pussard, Mourad Merzouk, Hubert Barennes. Increased uptake of quinine into the brain by inhibition of P-glycoprotein. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2007 Oct; 32(2):123-7. doi: 10.1016/j.ejps.2007.06.007. [PMID: 17698330]
  • Kunio Itoh, Mayumi Yamamura, Wataru Takasaki, Takamitsu Sasaki, Akiko Masubuchi, Yorihisa Tanaka. Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase. Biopharmaceutics & drug disposition. 2006 Apr; 27(3):133-9. doi: 10.1002/bdd.494. [PMID: 16400710]
  • Lastenia Ruiz-Mesia, Wilfredo Ruiz-Mesía, Matías Reina, Rafael Martínez-Diaz, Concepción de Inés, Ana Guadaño, Azucena González-Coloma. Bioactive cinchona alkaloids from Remijia peruviana. Journal of agricultural and food chemistry. 2005 Mar; 53(6):1921-6. doi: 10.1021/jf048880e. [PMID: 15769114]
  • Chensong Pan, Songyun Xu, Hanfa Zou, Zhong Guo, Yu Zhang, Baochuan Guo. Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry. Journal of the American Society for Mass Spectrometry. 2005 Feb; 16(2):263-70. doi: 10.1016/j.jasms.2004.11.005. [PMID: 15694776]
  • Jesús G Díaz, José Gavin Sazatornil, Matías López Rodríguez, Lastenia Ruiz Mesía, Gabriel Vargas Arana. Five new alkaloids from the leaves of Remijia peruviana. Journal of natural products. 2004 Oct; 67(10):1667-71. doi: 10.1021/np040053k. [PMID: 15497937]
  • Narasimhan Sreevidya, Shanta Mehrotra. Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials. Journal of AOAC International. 2003 Nov; 86(6):1124-7. doi: . [PMID: 14979692]
  • David C Warhurst, John C Craig, Ipemida S Adagu, David J Meyer, Sylvia Y Lee. The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malaria journal. 2003 Sep; 2(?):26. doi: 10.1186/1475-2875-2-26. [PMID: 14505493]
  • Hirotaka Shibuya, Chinami Kitamura, Shoji Maehara, Marie Nagahata, Hendig Winarno, Partomuan Simanjuntak, Hye-Sook Kim, Yusuke Wataya, Kazuyoshi Ohashi. Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens. Chemical & pharmaceutical bulletin. 2003 Jan; 51(1):71-4. doi: 10.1248/cpb.51.71. [PMID: 12520132]
  • Ariane Knauer, Jeeraphat Sirichaisinthop, Franz F Reinthaler, Gerhard Wiedermann, Gunther Wernsdorfer, Walther H Wernsdorfer. In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand. Wiener klinische Wochenschrift. 2003; 115 Suppl 3(?):39-44. doi: ". [PMID: 15508779]
  • A Koulman, R Bos, M Medarde, N Pras, W J Quax. A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species. Planta medica. 2001 Dec; 67(9):858-62. doi: 10.1055/s-2001-18849. [PMID: 11745025]
  • M N Ravishankara, N Shrivastava, H Padh, M Rajani. HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations. Planta medica. 2001 Apr; 67(3):294-6. doi: 10.1055/s-2001-11995. [PMID: 11345710]
  • E Solary, L Mannone, D Moreau, D Caillot, R O Casasnovas, H Guy, M Grandjean, J E Wolf, F André, P Fenaux, P Canal, B Chauffert, A Wotawa, M Bayssas, P Genne. Phase I study of cinchonine, a multidrug resistance reversing agent, combined with the CHVP regimen in relapsed and refractory lymphoproliferative syndromes. Leukemia. 2000 Dec; 14(12):2085-94. doi: 10.1038/sj.leu.2401945. [PMID: 11187897]
  • S Khalil. Atomic emission spectrometric determination of ephedrine, cinchonine, chlorpheniramine, atropine and diphenhydramine based on formation of ion associates with ammonium reineckate. Journal of pharmaceutical and biomedical analysis. 1999 Dec; 21(4):697-702. doi: 10.1016/s0731-7085(99)00130-2. [PMID: 10701933]
  • P M Loiseau, D X Nguyen. Plasmodium berghei mouse model: antimalarial activity of new alkaloid salts and of thiosemicarbazone and acridine derivatives. Tropical medicine & international health : TM & IH. 1996 Jun; 1(3):379-84. doi: 10.1046/j.1365-3156.1996.d01-50.x. [PMID: 8673843]
  • D F Stroncek, G P Herr. The chemical and immunoglobulin structural features necessary for reactions of quinine-dependent antibodies to neutrophils. Transfusion. 1995 Mar; 35(3):247-53. doi: 10.1046/j.1537-2995.1995.35395184282.x. [PMID: 7878718]
  • P Genne, O Duchamp, E Solary, J Magnette, J P Belon, B Chauffert. Cinchonine per os: efficient circumvention of P-glycoprotein-mediated multidrug resistance. Anti-cancer drug design. 1995 Mar; 10(2):103-18. doi: . [PMID: 7710633]
  • P Genne, O Duchamp, E Solary, D Pinard, J P Belon, M T Dimanche-Boitrel, B Chauffert. Comparative effects of quinine and cinchonine in reversing multidrug resistance on human leukemic cell line K562/ADM. Leukemia. 1994 Jan; 8(1):160-4. doi: . [PMID: 8289482]
  • J Karbwang, D Bunnag, T Harinasuta, S Chittamas, J Berth, P Druilhe. Pharmacokinetics of quinine, quinidine and Cinchonine when given as combination. The Southeast Asian journal of tropical medicine and public health. 1992 Dec; 23(4):773-6. doi: . [PMID: 1298088]
  • P Genne, M T Dimanche-Boitrel, R Y Mauvernay, G Gutierrez, O Duchamp, J M Petit, F Martin, B Chauffert. Cinchonine, a potent efflux inhibitor to circumvent anthracycline resistance in vivo. Cancer research. 1992 May; 52(10):2797-801. doi: . [PMID: 1581892]
  • A Sabchareon, T Chongsuphajaisiddhi, P Attanath, V Singhasivanon, M M Acmor-Apolinar, C Pojjaroen-Anant. Red cell and plasma concentrations of combined quinine-quinidine and quinine in falciparum malaria. Annals of tropical paediatrics. 1991; 11(4):315-24. doi: 10.1080/02724936.1991.11747522. [PMID: 1721787]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • J el Benna, M T Labro. Effect of quinine and cinchonine on human neutrophils functions in vitro. The Journal of antimicrobial chemotherapy. 1990 Jun; 25(6):949-57. doi: 10.1093/jac/25.6.949. [PMID: 2164514]
  • I Abraham, C T Ueda. Comparative disposition kinetics of two diastereomeric pairs of cinchona alkaloids in the dog. Journal of pharmaceutical sciences. 1984 Apr; 73(4):452-6. doi: 10.1002/jps.2600730407. [PMID: 6726627]
  • R M Kater, N Carulli, F L Iber. Differences in the rate of ethanol metabolism in recently drinking alcoholic and nondrinking subjects. The American journal of clinical nutrition. 1969 Dec; 22(12):1608-17. doi: 10.1093/ajcn/22.12.1608. [PMID: 5362487]