Lysergic acid (BioDeep_00000006527)

 

Secondary id: BioDeep_00001870116

Volatile Flavor Compounds natural product


代谢物信息卡片


6-Methyl-9,10-didehydroergoline-8-carboxylic acid

化学式: C16H16N2O2 (268.12117159999997)
中文名称: 麦角酸
谱图信息: 最多检出来源 Macaca mulatta(otcml) 1.11%

分子结构信息

SMILES: c1c2c3c(cc1)C1=C[C@H](CN([C@@H]1Cc3c[nH]2)C)C(=O)O
InChI: InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)

描述信息

An ergoline alkaloid comprising 6-methylergoline having additional unsaturation at the 9,10-position and a carboxy group at the 8-position.

同义名列表

5 个代谢物同义名

(+)-Lysergic acid; Lysergic acid; 6-Methyl-9,10-didehydroergoline-8-carboxylic acid; D-Lysergic acid; Lysergic acid



数据库引用编号

20 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)

20 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

  • Abigail M Jones, Chey R Steen, Daniel G Panaccione. Independent Evolution of a Lysergic Acid Amide in Aspergillus Species. Applied and environmental microbiology. 2021 11; 87(24):e0180121. doi: 10.1128/aem.01801-21. [PMID: 34586904]
  • Chey R Steen, Jessi K Sampson, Daniel G Panaccione. A Baeyer-Villiger Monooxygenase Gene Involved in the Synthesis of Lysergic Acid Amides Affects the Interaction of the Fungus Metarhizium brunneum with Insects. Applied and environmental microbiology. 2021 08; 87(17):e0074821. doi: 10.1128/aem.00748-21. [PMID: 34160271]
  • R Bharadwaj, H Jagadeesan, S R Kumar, S Ramalingam. Molecular mechanisms in grass-Epichloë interactions: towards endophyte driven farming to improve plant fitness and immunity. World journal of microbiology & biotechnology. 2020 Jun; 36(7):92. doi: 10.1007/s11274-020-02868-5. [PMID: 32562008]
  • Paige E Bragg, Matthew D Maust, Daniel G Panaccione. Ergot Alkaloid Biosynthesis in the Maize (Zea mays) Ergot Fungus Claviceps gigantea. Journal of agricultural and food chemistry. 2017 Dec; 65(49):10703-10710. doi: 10.1021/acs.jafc.7b04272. [PMID: 29172518]
  • Stephanie L Arnold, Daniel G Panaccione. Biosynthesis of the Pharmaceutically Important Fungal Ergot Alkaloid Dihydrolysergic Acid Requires a Specialized Allele of cloA. Applied and environmental microbiology. 2017 07; 83(14):. doi: 10.1128/aem.00805-17. [PMID: 28476772]
  • Haritha Durairaj, Michael D Steury, Narayanan Parameswaran. Paroxetine differentially modulates LPS-induced TNFα and IL-6 production in mouse macrophages. International immunopharmacology. 2015 Apr; 25(2):485-92. doi: 10.1016/j.intimp.2015.02.029. [PMID: 25744603]
  • Sarah L Robinson, Daniel G Panaccione. Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus. Applied and environmental microbiology. 2014 Oct; 80(20):6465-72. doi: 10.1128/aem.02137-14. [PMID: 25107976]
  • A P Foote, D L Harmon, K R Brown, J R Strickland, K R McLeod, L P Bush, J L Klotz. Constriction of bovine vasculature caused by endophyte-infected tall fescue seed extract is similar to pure ergovaline. Journal of animal science. 2012 May; 90(5):1603-9. doi: 10.2527/jas.2011-4513. [PMID: 22147482]
  • Robert A Ettlin, Junji Kuroda, Stephanie Plassmann, Makoto Hayashi, David E Prentice. Successful drug development despite adverse preclinical findings part 2: examples. Journal of toxicologic pathology. 2010 Dec; 23(4):213-34. doi: 10.1293/tox.23.213. [PMID: 22272032]
  • A Sobhani Najafabadi, M R Mofid, R Mohammadi, S Moghim. Quantification of ergovaline using HPLC and mass spectrometry in Iranian Neotyphodium infected tall fescue. Research in pharmaceutical sciences. 2010 Jul; 5(2):135-43. doi: ". [PMID: 22049272]
  • Miao Liu, Daniel G Panaccione, Christopher L Schardl. Phylogenetic analyses reveal monophyletic origin of the ergot alkaloid gene dmaW in fungi. Evolutionary bioinformatics online. 2009 Jun; 5(?):15-30. doi: 10.4137/ebo.s2633. [PMID: 19812724]
  • M J M De Lorme, S L Lodge-Ivey, A M Craig. Physiological and digestive effects of Neotyphodium coenophialum-infected tall fescue fed to lambs. Journal of animal science. 2007 May; 85(5):1199-206. doi: 10.2527/jas.2005-430. [PMID: 17296774]
  • C L Schultz, S L Lodge-Ivey, L P Bush, A M Craig, J R Strickland. Effects of initial and extended exposure to an endophyte-infected tall fescue seed diet on faecal and urinary excretion of ergovaline and lysergic acid in mature geldings. New Zealand veterinary journal. 2006 Aug; 54(4):178-84. doi: 10.1080/00480169.2006.36692. [PMID: 16915339]
  • S L Lodge-Ivey, K Walker, T Fleischmann, J E True, A M Craig. Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2006 Jul; 18(4):369-74. doi: 10.1177/104063870601800408. [PMID: 16921876]
  • Christopher L Schardl, Daniel G Panaccione, Paul Tudzynski. Ergot alkaloids--biology and molecular biology. The Alkaloids. Chemistry and biology. 2006; 63(?):45-86. doi: 10.1016/s1099-4831(06)63002-2. [PMID: 17133714]
  • Andreas F Lehner, Morrie Craig, Neil Fannin, Lowell Bush, Tom Tobin. Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds. Journal of mass spectrometry : JMS. 2005 Nov; 40(11):1484-502. doi: 10.1002/jms.933. [PMID: 16278935]
  • Prapassorn Damrongkool, Andrea B Sedlock, Carolyn A Young, Richard D Johnson, Kerry E Goetz, Barry Scott, Christopher L Schardl, Daniel G Panaccione. Structural analysis of a peptide synthetase gene required for ergopeptine production in the endophytic fungus Neotyphodium lolii. DNA sequence : the journal of DNA sequencing and mapping. 2005 Oct; 16(5):379-85. doi: 10.1080/10425170500273005. [PMID: 16243728]
  • Birgit M Dietz, Gail B Mahady, Guido F Pauli, Norman R Farnsworth. Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. Brain research. Molecular brain research. 2005 Aug; 138(2):191-7. doi: 10.1016/j.molbrainres.2005.04.009. [PMID: 15921820]
  • Daniel G Panaccione, Brian A Tapper, Geoffrey A Lane, Elizabeth Davies, Karl Fraser. Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6429-37. doi: 10.1021/jf0346859. [PMID: 14558758]
  • Jeffrey H Gertsch, Christopher Wood. Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis. Hawaii medical journal. 2003 Jun; 62(6):127, 129. doi: . [PMID: 12886727]
  • J M Schnitzius, N S Hill, C S Thompson, A M Craig. Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2001 May; 13(3):230-7. doi: 10.1177/104063870101300307. [PMID: 11482600]
  • T Watanabe, R Pakala, T Katagiri, C R Benedict. Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation. Atherosclerosis. 2001 Mar; 155(1):37-44. doi: 10.1016/s0021-9150(00)00526-8. [PMID: 11223424]
  • R Pakala, J T Willerson, C R Benedict. Effect of serotonin, thromboxane A2, and specific receptor antagonists on vascular smooth muscle cell proliferation. Circulation. 1997 Oct; 96(7):2280-6. doi: 10.1161/01.cir.96.7.2280. [PMID: 9337201]
  • S A Brooks, D R Lachno, B D Obermeyer. Automated high-performance liquid chromatographic method for the analysis of two novel ergoline compounds in human plasma. Journal of chromatography. B, Biomedical sciences and applications. 1997 Apr; 691(2):383-8. doi: 10.1016/s0378-4347(96)00438-0. [PMID: 9174275]
  • P Chen, Z Tian, G A Digenis, H H Tai. Enzyme immunoassay of two nicergoline metabolites, 10 alpha-methoxy-9, 10-dihydrolysergol (MDL) and 1-methyl-10 alpha-methoxy-9, 10-dihydrolysergol (MMDL). Research communications in molecular pathology and pharmacology. 1996 Jun; 92(3):315-28. doi: NULL. [PMID: 8827829]
  • A Sioufi, N Sandrenan, J Godbillon. Determination of 10 alpha-methoxy-9,10-dihydrolysergol, a nicergoline metabolite, in human urine by high performance liquid chromatography. Biomedical chromatography : BMC. 1992 Jan; 6(1):9-11. doi: 10.1002/bmc.1130060104. [PMID: 1600376]
  • M L Cohen, C J Parli, R W Fuller. 5-Hydroxytryptamine2 receptor antagonist activity of the acid metabolite (1-isopropyl dihydrolysergic acid) of the ergoline ester, sergolexole (LY281067). The Journal of pharmacology and experimental therapeutics. 1989 Dec; 251(3):1006-11. doi: NULL. [PMID: 2600800]
  • S R VandenBerg, S L Gonias. Covalent complexes of albumin with serotonin, ketanserin and lysergic acid antagonize the activity of serotonin in human platelets. Life sciences. 1989; 44(23):1777-85. doi: 10.1016/0024-3205(89)90565-1. [PMID: 2733551]
  • M L Cohen, R W Fuller, K D Kurz, C J Parli, N R Mason, D B Meyers, J K Smallwood, R E Toomey. Preclinical pharmacology of a new serotonergic receptor antagonist, LY281067. The Journal of pharmacology and experimental therapeutics. 1988 Jan; 244(1):106-12. doi: NULL. [PMID: 3335993]
  • F Erni. Liquid chromatography-mass spectrometry in the pharmaceutical industry: objectives and needs. Journal of chromatography. 1982 Apr; 251(2):141-51. doi: 10.1016/s0021-9673(00)98513-3. [PMID: 7096521]
  • T Oyama, T Shiosaka, S Fujita, I Matsumoto, Y Kobayashi, M Murase. [Isolation of Edwardsiella tarda from duodenal juice and feces of a patient with chronic cholangitis (author's transl)]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases. 1978 Apr; 52(4):105-10. doi: 10.11150/kansenshogakuzasshi1970.52.105. [PMID: 101616]
  • J M Jones, D F Amsbaugh, P W Stashak, B Prescott, P J Baker, D W Alling. Kinetics of the antibody response to type III pneumococcal polysaccharide. I. Evidence that suppressor cells function by inhibiting the recruitment and proliferation of antibody-producing cells. Journal of immunology (Baltimore, Md. : 1950). 1976 Mar; 116(3):647-56. doi: NULL. [PMID: 3604]
  • C A Wilson, C E Horth, A McNeilly, P G McDonald. Effect of serotonin and progesterone on induced ovulation in immature rats. The Journal of endocrinology. 1975 Feb; 64(2):337-47. doi: 10.1677/joe.0.0640337. [PMID: 1117243]
  • F SICUTERI. PROPHYLACTIC TREATMENT OF MIGRAINE BY MEANS OF LYSERGIC ACID DERIVATIVES. Triangle; the Sandoz journal of medical science. 1963 Oct; 6(?):116-25. doi: . [PMID: 14087164]
  • C PIOVELLA, A DESILVESTRI. [INTRAVASCULAR ERYTHROCYTE AGGREGATION AND D-1 METHYL-LYSERGIC ACID BUTANOLAMIDE (DESERRIL OR UML 491)]. Cuore e circolazione. 1963 Aug; 47(?):179-85. doi: . [PMID: 14084723]