Lupanin (BioDeep_00000396569)

Main id: BioDeep_00000003963

 


代谢物信息卡片


(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol(1,2-a:1,2-e)(1,5)diazocin-11-one

化学式: C15H24N2O (248.1889)
中文名称: 羽扇豆鹼
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CCN2CC3CC(C2C1)CN4C3CCCC4=O
InChI: InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1

描述信息

Lupanine is the delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids. It is a quinolizidine alkaloid, a tertiary amine and a delta-lactam. It is a conjugate base of a lupanine(1+). It derives from a hydride of a sparteine.
Lupanine is a natural product found in Leptolobium panamense, Ormosia fordiana, and other organisms with data available.
See also: Cytisus scoparius flowering top (part of).
The delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids.

同义名列表

36 个代谢物同义名

(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol(1,2-a:1,2-e)(1,5)diazocin-11-one; (7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1,2-e][1,5]diazocin-11-one; 7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1,2-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7R,7AS,14R,14AR)-REL-; 7,14-METHANO-2H,11H-DIPYRIDO(1,2-A:1,2-E)(1,5)DIAZOCIN-11-ONE, DODECAHYDRO-, (7S,7AR,14S,14AS)-; lupanine monohydrochloride, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer; lupanine monohydrochloride, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer; lupanine monohydrobromide, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer; (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadecan-6-one; (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one; lupanine monoperchlorate, (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer; lupanine sulfate (1:1), (7S-(7alpha,7abeta,14alpha,14aalpha))-isomer; lupanine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer; lupanine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer; lupanine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer; JYIJIIVLEOETIQ-XDQVBPFNSA-N; LUPANINE DL-FORM [MI]; LUPANINE D-FORM [MI]; (+/-)-2-OXOSPARTEINE; (RAC)-2-OXOSPARTEINE; (+)-2-Oxosparteine; alpha-Isolupanine; Lupanine, (+/-)-; Lupanine d-form; UNII-9K48888N9P; (+/-)-LUPANINE; 2-Oxosparteine; LUPANINE, (+)-; Spartein-2-one; Lupanine, D-; (+)-Lupanine; DL-LUPANINE; 9K48888N9P; d-Lupanine; lupanine; Lupanin; Lupanine



数据库引用编号

14 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

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)

0 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。

亚细胞结构定位 关联基因列表


文献列表

  • Stella Parmaki, Argyro Tsipa, Marlen I Vasquez, João M J Gonçalves, Ioanna Hadjiadamou, Frederico C Ferreira, Carlos A M Afonso, Chrysoulla Drouza, Michalis Koutinas. Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization. Microbial cell factories. 2020 Mar; 19(1):67. doi: 10.1186/s12934-020-01324-1. [PMID: 32169079]
  • Stella Parmaki, Ioannis Vyrides, Marlen I Vasquez, Viki Hartman, Irene Zacharia, Ioanna Hadjiadamou, Catarina B M Barbeitos, Frederico C Ferreira, Carlos A M Afonso, Chrysoulla Drouza, Michalis Koutinas. Bioconversion of alkaloids to high-value chemicals: Comparative analysis of newly isolated lupanine degrading strains. Chemosphere. 2018 Feb; 193(?):50-59. doi: 10.1016/j.chemosphere.2017.10.165. [PMID: 29126065]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Daniel Cook. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Research in veterinary science. 2017 Dec; 115(?):195-200. doi: 10.1016/j.rvsc.2017.04.019. [PMID: 28494312]
  • Sumira Jan, Azra N Kamili, Javid A Parray, Yashbir S Bedi, Parvaiz Ahmad. Microclimatic variation in UV perception and related disparity in tropane and quinolizidine alkaloid composition of Atropa acuminata, Lupinus polyphyllus and Hyoscyamus niger. Journal of photochemistry and photobiology. B, Biology. 2016 Aug; 161(?):230-5. doi: 10.1016/j.jphotobiol.2016.04.028. [PMID: 27285814]
  • Sarah E J Arnold, M Eduardo Peralta Idrovo, Luis J Lomas Arias, Steven R Belmain, Philip C Stevenson. Herbivore defence compounds occur in pollen and reduce bumblebee colony fitness. Journal of chemical ecology. 2014 Aug; 40(8):878-81. doi: 10.1007/s10886-014-0467-4. [PMID: 24952086]
  • N Merghoub, L Benbacer, H El Btaouri, H Ait Benhassou, C Terryn, M Attaleb, C Madoulet, A Benjouad, M El Mzibri, H Morjani, S Amzazi. In vitro antiproliferative effect and induction of apoptosis by Retama monosperma L. extract in human cervical cancer cells. Cellular and molecular biology (Noisy-le-Grand, France). 2011 Oct; 57 Suppl(?):OL1581-91. doi: 10.5772/30025. [PMID: 22000488]
  • Markus Ganzera, Anja Krüger, Michael Wink. Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection. Journal of pharmaceutical and biomedical analysis. 2010 Dec; 53(5):1231-5. doi: 10.1016/j.jpba.2010.05.030. [PMID: 20580181]
  • Pavlos Stampolidis, Naheed N Kaderbhai, Mustak A Kaderbhai. Periplasmically-exported lupanine hydroxylase undergoes transition from soluble to functional inclusion bodies in Escherichia coli. Archives of biochemistry and biophysics. 2009 Apr; 484(1):8-15. doi: 10.1016/j.abb.2009.01.017. [PMID: 19467626]
  • Dolores Pérez-Laínez, Rosario García-Mateos, Ruben San Miguel-Chávez, Marcos Soto-Hernández, Enrique Rodríguez-Pérez, Geofrey Kite. Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Sep; 63(9-10):653-7. doi: 10.1515/znc-2008-9-1007. [PMID: 19040102]
  • Donatella Resta, Giovanna Boschin, Alessandra D'Agostina, Anna Arnoldi. Evaluation of total quinolizidine alkaloids content in lupin flours, lupin-based ingredients, and foods. Molecular nutrition & food research. 2008 Apr; 52(4):490-5. doi: 10.1002/mnfr.200700206. [PMID: 18324702]
  • Łukasz Marczak, Przemysław Wojtaszek, Maciej Stobiecki. Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast. Journal of plant physiology. 2008; 165(3):239-50. doi: 10.1016/j.jplph.2007.06.018. [PMID: 17928101]
  • Teresa Bobkiewicz-Kozłowska, Marzena Dworacka, Sebastian Kuczyński, Małgorzata Abramczyk, Renata Kolanoś, Waleria Wysocka, Pedro M Garcia Lopez, Hanna Winiarska. Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats. European journal of pharmacology. 2007 Jun; 565(1-3):240-4. doi: 10.1016/j.ejphar.2007.02.032. [PMID: 17379208]
  • Stephen T Lee, Michael H Ralphs, Kip E Panter, Daniel Cook, Dale R Gardner. Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season. Journal of chemical ecology. 2007 Jan; 33(1):75-84. doi: 10.1007/s10886-006-9211-z. [PMID: 17146716]
  • Raja Sundararajan, Nazeer Ahamed Haja, Kumar Venkatesan, Kakali Mukherjee, Bishnu Pada Saha, Arun Bandyopadhyay, Pulok Kumar Mukherjee. Cytisus scoparius link--a natural antioxidant. BMC complementary and alternative medicine. 2006 Mar; 6(?):8. doi: 10.1186/1472-6882-6-8. [PMID: 16542432]
  • J Bañuelos Pineda, G Nolasco Rodríguez, J A Monteon, P M García López, M A Ruiz Lopez, J García Estrada. Histological evaluation of brain damage caused by crude quinolizidine alkaloid extracts from lupines. Histology and histopathology. 2005 10; 20(4):1147-53. doi: 10.14670/hh-20.1147. [PMID: 16136497]
  • Alice Martins, Michael Wink, Andreas Tei, Michèle Brum-Bousquet, François Tillequin, Amélia-Pilar Rauter. A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochemical analysis : PCA. 2005 Jul; 16(4):264-6. doi: 10.1002/pca.832. [PMID: 16042152]
  • Ramón Aguiar, Michael Wink. Do naïve ruminants degrade alkaloids in the rumen?. Journal of chemical ecology. 2005 Apr; 31(4):761-87. doi: 10.1007/s10886-005-3543-y. [PMID: 16124250]
  • Pedro M García López, P Garzón de la Mora, W Wysocka, Bárbara Maiztegui, María E Alzugaray, Héctor Del Zotto, María I Borelli. Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion. European journal of pharmacology. 2004 Nov; 504(1-2):139-42. doi: 10.1016/j.ejphar.2004.09.008. [PMID: 15507230]
  • Clive C Gay, Kip E Panter, Katrina L Mealey, John M Gay, Steven W Hjartarson, Ahmed Tibary, Ernie S Motteram, Terrie Wierenga, Lynn F James. Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves. American journal of veterinary research. 2004 Nov; 65(11):1580-3. doi: 10.2460/ajvr.2004.65.1580. [PMID: 15566098]
  • S Lopez-Ortiz, K E Panter, J A Pfister, K L Launchbaugh. The effect of body condition on disposition of alkaloids from silvery lupine (Lupinus argenteus pursh) in sheep. Journal of animal science. 2004 Sep; 82(9):2798-805. doi: 10.2527/2004.8292798x. [PMID: 15446497]
  • Alice Martins, Michael Wink, Andreas Tei, Amélia P Rauter. Quinolizidine alkaloid profiles of two taxa of Teline maderensis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Nov; 58(11-12):776-8. doi: 10.1515/znc-2003-11-1203. [PMID: 14713148]
  • Filomena M C Santana, Teresa Pinto, Arsénio M Fialho, Isabel Sá-Correia, José M A Empis. Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract. Journal of agricultural and food chemistry. 2002 Apr; 50(8):2318-23. doi: 10.1021/jf011371h. [PMID: 11929291]
  • Kalina Bermúdez Torres, Norma Robledo Quintos, Laura L Barrera Necha, Michael Wink. Alkaloid profile of leaves and seeds of Lupinus hintonii C. P. Smith. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Mar; 57(3-4):243-7. doi: 10.1515/znc-2002-3-408. [PMID: 12064721]
  • S Aufreiter, W C Mahaney, M W Milner, M A Huffman, R G Hancock, M Wink, M Reich. Mineralogical and chemical interactions of soils eaten by chimpanzees of the Mahale Mountains and Gombe Stream National Parks, Tanzania. Journal of chemical ecology. 2001 Feb; 27(2):285-311. doi: 10.1023/a:1005628405321. [PMID: 14768816]
  • J M Pozuelo, M M Lucas, C de Lorenzo, M Fernández-Pascual, S Maldonado, M R de Felipe. Immunolocalization of alkaloids and X-ray microanalysis of elements in lupin seeds. Protoplasma. 2001; 218(1-2):104-11. doi: 10.1007/bf01288366. [PMID: 11732315]
  • H A Oboh, M Muzquiz, C Burbano, C Cuadrado, M M Pedrosa, G Ayet, A U Osagie. Anti-nutritional constituents of six underutilized legumes grown in Nigeria. Journal of chromatography. A. 1998 Oct; 823(1-2):307-12. doi: 10.1016/s0021-9673(98)00542-1. [PMID: 9818409]
  • J Pothier, S L Cheav, N Galand, C Dormeau, C Viel. A comparative study of the effects of sparteine, lupanine and lupin extract on the central nervous system of the mouse. The Journal of pharmacy and pharmacology. 1998 Aug; 50(8):949-54. doi: 10.1111/j.2042-7158.1998.tb04013.x. [PMID: 9751462]
  • M C Robbins, D S Petterson, P G Brantom. A 90-day feeding study of the alkaloids of Lupinus angustifolius in the rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1996 Aug; 34(8):679-86. doi: 10.1016/0278-6915(96)00040-3. [PMID: 8883468]
  • A Chaudhuri, W J Keller. New mammalian metabolites of sparteine. Life sciences. 1990; 47(4):319-25. doi: 10.1016/0024-3205(90)90590-n. [PMID: 2388532]
  • R A Smith. Potential edible lupine poisonings in humans. Veterinary and human toxicology. 1987 Dec; 29(6):444-5. doi: ". [PMID: 3424650]
  • F JAMINET. [Biochemical study of the common broom (Sarothamnus scoparius L.). III. Action of the oxidizing system consisting of ascorbic acid, ferric ions and oxygen, on the sparteine and lupanine in the plant]. Journal de pharmacie de Belgique. 1958 Nov; 13(11-12):577-84. doi: ". [PMID: 13642253]