Cephaeline (BioDeep_00000000045)

   

PANOMIX_OTCML-2023 Chemicals and Drugs natural product


代谢物信息卡片


(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

化学式: C28H38N2O4 (466.2831428)
中文名称: 吐根酚碱, 吐根碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.08%

Reviewed

Last reviewed on 2024-07-12.

Cite this Page

Cephaeline. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cephaeline (retrieved 2024-11-05) (BioDeep RN: BioDeep_00000000045). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)O)OC)OC)OC
InChI: InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3

描述信息

Cephaeline is a pyridoisoquinoline comprising emetam having a hydroxy group at the 6-position and methoxy substituents at the 7-, 10- and 11-positions. It derives from a hydride of an emetan.
Cephaeline is a natural product found in Dorstenia psilurus, Pogonopus tubulosus, and other organisms with data available.

Cephaeline is an alkaloid compound that belongs to the isoquinoline alkaloid family. It is naturally found in certain plant species, particularly those of the Cephalotaxus genus, which includes trees and shrubs native to East Asia and the Himalayas. Cephaeline is known for its pharmacological properties and has been the subject of various studies for its potential therapeutic applications.
Chemically, cephaeline has a complex structure characterized by an isoquinoline core with additional functional groups attached. It is classified as a monoterpenoid indole alkaloid, reflecting its biosynthetic origin from the amino acid tryptophan. The presence of these functional groups contributes to its biological activity and pharmacological effects.
In terms of its physical properties, cephaeline is typically a crystalline solid with a defined melting point. It is slightly soluble in water but more soluble in organic solvents, which is common for alkaloids of its class. The exact color and solubility characteristics can vary depending on the presence of impurities or derivatives.
Cephaeline has been of interest in the field of pharmacognosy and drug discovery due to its potential therapeutic effects, including anti-cancer, anti-inflammatory, and neuroprotective properties. However, further research is needed to fully understand its mechanisms of action and potential uses in medicine.


Annotation level-1

(-)-Cephaeline. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=483-17-0 (retrieved 2024-07-12) (CAS RN: 483-17-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

26 个代谢物同义名

6-ISOQUINOLINOL, 1-(((2S,3R,11BS)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-YL)METHYL)-1,2,3,4-TETRAHYDRO-7-METHOXY-, (1R)-; (1R)-1-(((2S,3R,11BS)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-YL)METHYL)-1,2,3,4-TETRAHYDRO-7-METHOXY-6-ISOQUINOLINOL; (1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol; Emetan-6-ol, 7,10,11-trimethoxy-; 7,10,11-Trimethoxyemetan-6-ol; Thiazole, 2-iodo-5-methyl-; Dihydropsychotrine; Prestwick3_000428; desmethyl-emetine; Prestwick2_000428; Prestwick0_000428; Prestwick1_000428; desmethylemetine; CEPHAELINE [MI]; (-)-Cephaeline; BPBio1_000458; MEGxp0_001992; ACon1_001325; NCI60_002878; Cephaelinel; Cephaeline; Alangine B; Cepheline; cephaline; cephaelin; Ipecac (Cephaeline)



数据库引用编号

33 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(1)

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)

74 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

  • You-Sheng Cai, Cong Wang, Congkui Tian, Wen-Ting Sun, Ling Chen, Di Xiao, Si-Yuan Zhou, Guofu Qiu, Jianqing Yu, Kongkai Zhu, Sheng-Ping Yang. Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity. Journal of natural products. 2019 09; 82(9):2645-2652. doi: 10.1021/acs.jnatprod.9b00670. [PMID: 31513408]
  • Mumu Chakraborty, Sibabrata Mukhopadhyay. Angustinine--a new benzopyridoquinolizine alkaloid from Alangium lamarckii. Natural product communications. 2012 Sep; 7(9):1169-70. doi: ". [PMID: 23074898]
  • Lei Sun, Xiaoru Hu, Lina Liu, Hongyu Jin, Ruichao Lin. [Rapid detection of alkaloids in Ipecac by direct analysis in real time tandem mass spectrometry (DART-MS/MS)]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(10):1426-30. doi: 10.4268/cjcmm20121017. [PMID: 22860455]
  • Bo Eng Cheong, Tomoya Takemura, Kayo Yoshimatsu, Fumihiko Sato. Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha. Bioscience, biotechnology, and biochemistry. 2011; 75(1):107-13. doi: 10.1271/bbb.100605. [PMID: 21228475]
  • Taiji Nomura, Toni M Kutchan. Is a metabolic enzyme complex involved in the efficient and accurate control of Ipecac alkaloid biosynthesis in Psychotria ipecacuanha?. Plant signaling & behavior. 2010 Jul; 5(7):875-7. doi: 10.4161/psb.5.7.11901. [PMID: 20495341]
  • Luiz Orlando de Oliveira, Ana Aparecida Bandini Rossi, Ernane Ronie Martins, Flávia Reis de Carvalho Batista, Roberta Santos Silva. Molecular phylogeography of Carapichea ipecacuanha, an amphitropical shrub that occurs in the understory of both semideciduous and evergreen forests. Molecular ecology. 2010 Apr; 19(7):1410-22. doi: 10.1111/j.1365-294x.2010.04591.x. [PMID: 20298468]
  • Jillian M Hagel, Peter J Facchini. Biochemistry and occurrence of o-demethylation in plant metabolism. Frontiers in physiology. 2010; 1(?):14. doi: 10.3389/fphys.2010.00014. [PMID: 21423357]
  • Luiz Orlando de Oliveira, Bruna Afonso Venturini, Ana Aparecida Bandini Rossi, Saulo Santos Hastenreiter. Clonal diversity and conservation genetics of the medicinal plant Carapichea ipecacuanha (Rubiaceae). Genetics and molecular biology. 2010 Jan; 33(1):86-93. doi: 10.1590/s1415-47572009005000096. [PMID: 21637610]
  • Taiji Nomura, Alfonso Lara Quesada, Toni M Kutchan. The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha. The Journal of biological chemistry. 2008 Dec; 283(50):34650-9. doi: 10.1074/jbc.m806953200. [PMID: 18927081]
  • M R Lee. Ipecacuanha: the South American vomiting root. The journal of the Royal College of Physicians of Edinburgh. 2008 Dec; 38(4):355-60. doi: . [PMID: 19227966]
  • Kayo Yoshimatsu, Koichiro Shimomura, Mami Yamazaki, Kazuki Saito, Fumiyuki Kiuchi. Transformation of ipecac (Cephaelis ipecacuanha) with Agrobacterium rhizogenes. Planta medica. 2003 Nov; 69(11):1018-23. doi: 10.1055/s-2003-45149. [PMID: 14735440]
  • Masatomo Yamashita, Mamoru Yamashita, Junichi Azuma. Urinary excretion of ipecac alkaloids in human volunteers. Veterinary and human toxicology. 2002 Oct; 44(5):257-9. doi: . [PMID: 12361104]
  • Takayuki Asano, Kazuhisa Ishihara, Yoko Wakui, Toshihiko Yanagisawa, Masayuki Kimura, Hideo Kamei, Takemi Yoshida, Yukio Kuroiwa, Yuichi Fujii, Mamoru Yamashita, Takanori Kuramochi, Hiroki Tomisawa, Mitsuru Tateishi. Absorption, distribution and excretion of 3H-labeled cephaeline- and emetine-spiked ipecac syrup in rats. European journal of drug metabolism and pharmacokinetics. 2002 Jan; 27(1):17-27. doi: 10.1007/bf03190401. [PMID: 11996323]
  • Takayuki Asano, Junko Watanabe, Chiharu Sadakane, Kazuhisa Ishihara, Kazuhiro Hirakura, Yoko Wakui, Toshihiko Yanagisawa, Masayuki Kimura, Hideo Kamei, Takemi Yoshida, Yuichi Fujii, Mamoru Yamashita. Biotransformation of the ipecac alkaloids cephaeline and emetine from ipecac syrup in rats. European journal of drug metabolism and pharmacokinetics. 2002 Jan; 27(1):29-35. doi: 10.1007/bf03190402. [PMID: 11996324]
  • T Asano, C Sadakane, K Ishihara, T Yanagisawa, M Kimura, H Kamei. High-performance liquid chromatographic assay with fluorescence detection for the determination of cephaeline and emetine in human plasma and urine. Journal of chromatography. B, Biomedical sciences and applications. 2001 Jun; 757(2):197-206. doi: 10.1016/s0378-4347(01)00170-0. [PMID: 11417863]
  • T Asano, H Kushida, C Sadakane, K Ishihara, Y Wakui, T Yanagisawa, M Kimura, H Kamei, T Yoshida. Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biological & pharmaceutical bulletin. 2001 Jun; 24(6):678-82. doi: 10.1248/bpb.24.678. [PMID: 11411558]
  • E J Scharman, J M Hutzler, J G Rosencrance, T S Tracy. Single dose pharmacokinetics of syrup of ipecac. Therapeutic drug monitoring. 2000 Oct; 22(5):566-73. doi: 10.1097/00007691-200010000-00011. [PMID: 11034262]
  • 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]
  • M F Lachman, R Romeo, R B McComb. Emetine identified in urine by HPLC, with fluorescence and ultraviolet/diode array detection, in a patient with cardiomyopathy. Clinical chemistry. 1989 Mar; 35(3):499-502. doi: . [PMID: 2920426]
  • H Szmigielska. The effect of prolonged vasopressin administration on the level and metabolism of catecholamines in the rat brain and kidneys. Acta physiologica Polonica. 1976 May; 27(3):259-64. doi: NULL. [PMID: 7918]
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  • W WISNIEWSKI, A PIETURA. [Colorimetric method for the determination of emetine and cephaeline in Cephaelis roots and in galenicals obtained from them]. Acta poloniae pharmaceutica. 1963; 20(?):43-51. doi: ". [PMID: 14001348]
  • F D'ABRAMO, E TOMASOS. [Biosynthesis of cephaline in the kidney]. Bollettino della Societa italiana di biologia sperimentale. 1955 Sep; 31(9-10):1395-7. doi: NULL. [PMID: 13329139]
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