Ergovaline (BioDeep_00000231713)

代谢物信息卡片

Ergovaline

化学式: C29H35N5O5 (533.2638)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)C1C(=O)N2CCCC2C2(O)OC(C)(NC(=O)C3C=C4c5cccc6[nH]cc(c56)CC4N(C)C3)C(=O)N12
InChI: InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21-,22+,24+,28-,29+/m1/s1

描述信息

D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
CONFIDENCE Claviceps purpurea sclerotia

同义名列表

1 个代谢物同义名

Ergovaline

数据库引用编号

10 个数据库交叉引用编号

ChEBI: CHEBI:184047
PubChem: 104843
KNApSAcK: C00011228
CAS: 2873-38-3
MoNA: AC000331
MoNA: AC000330
MoNA: AC000329
MoNA: AC000328
MoNA: AC000327
PMhub: MS000013625

分类词条

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)

7 个相关的物种来源信息

173841 - Cenchrus echinatus: 10.1021/NP50071A021
5111 - Claviceps purpurea: 10.1139/V79-263
73839 - Epichloe festucae var. lolii: 10.1128/AEM.00257-07
5113 - Epichloe typhina: 10.1021/JF00105A055
52153 - Festuca rubra:
4606 - Lolium arundinaceum:
375857 - Scolochloa festucacea:

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

Florencia M Realini, Víctor M Escobedo, Andrea C Ueno, Daniel A Bastías, Christopher L Schardl, Fernando Biganzoli, Pedro E Gundel. Anti-herbivory defences delivered by Epichloë fungal endophytes: a quantitative review of alkaloid concentration variation among hosts and plant parts. Annals of botany. 2024 Apr; 133(4):509-520. doi: 10.1093/aob/mcae014. [PMID: 38320313]
Krista La Moen Lea, S Ray Smith. Using On-Farm Monitoring of Ergovaline and Tall Fescue Composition for Horse Pasture Management. Toxins. 2021 09; 13(10):. doi: 10.3390/toxins13100683. [PMID: 34678976]
Debbie Hudson, Wade Mace, Alison Popay, Joanne Jensen, Catherine McKenzie, Catherine Cameron, Richard Johnson. Genetic Manipulation of the Ergot Alkaloid Pathway in Epichloë festucae var. lolii and Its Effect on Black Beetle Feeding Deterrence. Toxins. 2021 01; 13(2):. doi: 10.3390/toxins13020076. [PMID: 33498584]
Priyanka Reddy, Joanne Hemsworth, Kathryn M Guthridge, Antony Vinh, Simone Vassiliadis, Vilnis Ezernieks, German C Spangenberg, Simone J Rochfort. Ergot alkaloid mycotoxins: physiological effects, metabolism and distribution of the residual toxin in mice. Scientific reports. 2020 06; 10(1):9714. doi: 10.1038/s41598-020-66358-2. [PMID: 32546814]
Gyuchul Ahn, Kara Ricconi, Suelen Avila, James L Klotz, David L Harmon. Ruminal motility, reticuloruminal fill, and eating patterns in steers exposed to ergovaline. Journal of animal science. 2020 Jan; 98(1):. doi: 10.1093/jas/skz374. [PMID: 31850497]
Simone Vassiliadis, Aaron C Elkins, Priyanka Reddy, Kathryn M Guthridge, German C Spangenberg, Simone J Rochfort. A Simple LC-MS Method for the Quantitation of Alkaloids in Endophyte-Infected Perennial Ryegrass. Toxins. 2019 11; 11(11):. doi: 10.3390/toxins11110649. [PMID: 31703425]
Rebecca K Poole, Alecia R Brown, Matthew H Poore, Carrie L Pickworth, Daniel H Poole. Effects of endophyte-infected tall fescue seed and protein supplementation on stocker steers: II. Adaptive and innate immune function. Journal of animal science. 2019 Oct; 97(10):4160-4170. doi: 10.1093/jas/skz250. [PMID: 31353402]
Wiebke Rudolph, Daniela Remane, Dirk K Wissenbach, Frank T Peters. Comparative study on the metabolism of the ergot alkaloids ergocristine, ergocryptine, ergotamine, and ergovaline in equine and human S9 fractions and equine liver preparations. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Oct; 49(10):1149-1157. doi: 10.1080/00498254.2018.1542187. [PMID: 30623698]
Maslyn A Greene, Jessica L Britt, Rhonda R Powell, F Alex Feltus, William C Bridges, Terri Bruce, James L Klotz, Markus F Miller, Susan K Duckett. Ergot alkaloid exposure during gestation alters: 3. Fetal growth, muscle fiber development, and miRNA transcriptome1. Journal of animal science. 2019 Jul; 97(7):3153-3168. doi: 10.1093/jas/skz153. [PMID: 31051033]
Paula Andrea Giraldo, Carly Elliott, Pieter Badenhorst, Gavin Kearney, German C Spangenberg, Noel O I Cogan, Kevin F Smith. Evaluation of endophyte toxin production and its interaction with transgenic perennial ryegrass (Lolium perenne L.) with altered expression of fructosyltransferases. Transgenic research. 2018 10; 27(5):397-407. doi: 10.1007/s11248-018-0087-9. [PMID: 30030680]
Lia D Murty, Jennifer M Duringer, A Morrie Craig. Co-exposure of the Mycotoxins Lolitrem B and Ergovaline in Steers Fed Perennial Ryegrass ( Lolium perenne) Straw: Metabolic Characterization of Excreta. Journal of agricultural and food chemistry. 2018 Jun; 66(25):6394-6401. doi: 10.1021/acs.jafc.8b00963. [PMID: 29847929]
Emily A Melchior, Jason K Smith, Liesel G Schneider, J Travis Mulliniks, Gary E Bates, Zachary D McFarlane, Michael D Flythe, James L Klotz, Jack P Goodman, Huihua Ji, Phillip R Myer. Effects of red clover isoflavones on tall fescue seed fermentation and microbial populations in vitro. PloS one. 2018; 13(10):e0201866. doi: 10.1371/journal.pone.0201866. [PMID: 30335760]
B E Harlow, J P Goodman, B C Lynn, M D Flythe, H Ji, G E Aiken. Ruminal tryptophan-utilizing bacteria degrade ergovaline from tall fescue seed extract. Journal of animal science. 2017 Feb; 95(2):980-988. doi: 10.2527/jas.2016.1128. [PMID: 28380578]
Simona Florea, Timothy D Phillips, Daniel G Panaccione, Mark L Farman, Christopher L Schardl. Chromosome-End Knockoff Strategy to Reshape Alkaloid Profiles of a Fungal Endophyte. G3 (Bethesda, Md.). 2016 08; 6(8):2601-10. doi: 10.1534/g3.116.029686. [PMID: 27334939]
J J Villalba, C Spackman, B M Goff, J L Klotz, T Griggs, J W MacAdam. Interaction between a tannin-containing legume and endophyte-infected tall fescue seed on lambs' feeding behavior and physiology. Journal of animal science. 2016 Feb; 94(2):845-57. doi: 10.2527/jas.2015-9790. [PMID: 27065155]
N Zbib, C Repussard, D Tardieu, N Priymenko, C Domange, P Guerre. Toxicity of endophyte-infected ryegrass hay containing high ergovaline level in lactating ewes. Journal of animal science. 2015 Aug; 93(8):4098-109. doi: 10.2527/jas.2014-8848. [PMID: 26440189]
Karen Walker, Jennifer Duringer, A Morrie Craig. Determination of the Ergot Alkaloid Ergovaline in Tall Fescue Seed and Straw Using a QuEChERS Extraction Method with High-Performance Liquid Chromatography-Fluorescence Detection. Journal of agricultural and food chemistry. 2015 Apr; 63(16):4236-42. doi: 10.1021/acs.jafc.5b01149. [PMID: 25811236]
Céline Repussard, Nasrallah Zbib, Didier Tardieu, Philippe Guerre. Ergovaline and lolitrem B concentrations in perennial ryegrass in field culture in southern France: distribution in the plant and impact of climatic factors. Journal of agricultural and food chemistry. 2014 Dec; 62(52):12707-12. doi: 10.1021/jf504581y. [PMID: 25526521]
N Zbib, C Repussard, D Tardieu, N Priymenko, C Domange, P Guerre. Ergovaline in tall fescue and its effect on health, milk quality, biochemical parameters, oxidative status, and drug metabolizing enzymes of lactating ewes. Journal of animal science. 2014 Nov; 92(11):5112-23. doi: 10.2527/jas.2014-8106. [PMID: 25253811]
Céline Repussard, Nasrallah Zbib, Didier Tardieu, Philippe Guerre. Endophyte infection of tall fescue and the impact of climatic factors on ergovaline concentrations in field crops cultivated in southern France. Journal of agricultural and food chemistry. 2014 Oct; 62(39):9609-14. doi: 10.1021/jf503015m. [PMID: 25192465]
Andrew J Tanentzap, Mark Vicari, Dawn R Bazely. Ungulate saliva inhibits a grass-endophyte mutualism. Biology letters. 2014 Jul; 10(7):. doi: 10.1098/rsbl.2014.0460. [PMID: 25055816]
D L Cross, C R Reinemeyer, J C Prado, R L Donnell, K G Bond, H Farr, S L Longhofer. Efficacy of domperidone gel in an induced model of fescue toxicosis in periparturient mares. Theriogenology. 2012 Oct; 78(6):1361-70. doi: 10.1016/j.theriogenology.2012.06.002. [PMID: 22898028]
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]
L K Johnstone, I G Mayhew, L R Fletcher. Clinical expression of lolitrem B (perennial ryegrass) intoxication in horses. Equine veterinary journal. 2012 May; 44(3):304-9. doi: 10.1111/j.2042-3306.2011.00439.x. [PMID: 21793878]
A F Koontz, L P Bush, J L Klotz, K R McLeod, F N Schrick, D L Harmon. Evaluation of a ruminally dosed tall fescue seed extract as a model for fescue toxicosis in steers. Journal of animal science. 2012 Mar; 90(3):914-21. doi: 10.2527/jas.2011-4292. [PMID: 22064740]
Edwena D Miles, Yan Xue, James R Strickland, James A Boling, James C Matthews. Ergopeptines bromocriptine and ergovaline and the dopamine type-2 receptor inhibitor domperidone inhibit bovine equilibrative nucleoside transporter 1-like activity. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9691-9. doi: 10.1021/jf201713m. [PMID: 21790119]
S R Gooneratne, M Scannell, M Wellby, L Fletcher. Changes in concentrations of lysergol in urine and prolactin in plasma, rectal temperature and respiration rate in sheep selected for resistance or susceptibility to ryegrass staggers and fed ergovaline. New Zealand veterinary journal. 2011 Sep; 59(5):233-8. doi: 10.1080/00480169.2011.601538. [PMID: 21851300]
G E Aiken, J R Strickland, M L Looper, L P Bush, F N Schrick. Hemodynamics are altered in the caudal artery of beef heifers fed different ergot alkaloid concentrations. Journal of animal science. 2009 Jun; 87(6):2142-50. doi: 10.2527/jas.2008-1562. [PMID: 19251925]
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]
A K Matthews, M H Poore, G B Huntington, J T Green. Intake, digestion, and N metabolism in steers fed endophyte-free, ergot alkaloid-producing endophyte-infected, or nonergot alkaloid-producing endophyte-infected fescue hay. Journal of animal science. 2005 May; 83(5):1179-85. doi: 10.2527/2005.8351179x. [PMID: 15827262]
Martin J Spiering, Geoffrey A Lane, Michael J Christensen, Jan Schmid. Distribution of the fungal endophyte Neotyphodium lolii is not a major determinant of the distribution of fungal alkaloids in Lolium perenne plants. Phytochemistry. 2005 Jan; 66(2):195-202. doi: 10.1016/j.phytochem.2004.11.021. [PMID: 15652576]
Jinghong Wang, Caroline Machado, Daniel G Panaccione, Huei-Fung Tsai, Christopher L Schardl. The determinant step in ergot alkaloid biosynthesis by an endophyte of perennial ryegrass. Fungal genetics and biology : FG & B. 2004 Feb; 41(2):189-98. doi: 10.1016/j.fgb.2003.10.002. [PMID: 14732265]
Ali S Moubarak, Zelpha B Johnson, Charles F Rosenkrans. Antagonistic effects of simultaneous exposure of ergot alkaloids on kidney adenosine triphosphatase system. In vitro cellular & developmental biology. Animal. 2003 Sep; 39(8-9):395-8. doi: 10.1290/1543-706x(2003)039<0395:aeoseo>2.0.co;2. [PMID: 15038775]
M S Gadberry, T M Denard, D E Spiers, E L Piper. Effects of feeding ergovaline on lamb performance in a heat stress environment. Journal of animal science. 2003 Jun; 81(6):1538-45. doi: 10.2527/2003.8161538x. [PMID: 12817502]
Martin J Spiering, Elizabeth Davies, Brian A Tapper, Jan Schmid, Geoffrey A Lane. Simplified extraction of ergovaline and peramine for analysis of tissue distribution in endophyte-infected grass tillers. Journal of agricultural and food chemistry. 2002 Oct; 50(21):5856-62. doi: 10.1021/jf025602b. [PMID: 12358450]
D J Smith, N W Shappell. Technical note: epimerization of ergopeptine alkaloids in organic and aqueous solvents. Journal of animal science. 2002 Jun; 80(6):1616-22. doi: 10.2527/2002.8061616x. [PMID: 12078743]
D G Panaccione, R D Johnson, J Wang, C A Young, P Damrongkool, B Scott, C L Schardl. Elimination of ergovaline from a grass-Neotyphodium endophyte symbiosis by genetic modification of the endophyte. Proceedings of the National Academy of Sciences of the United States of America. 2001 Oct; 98(22):12820-5. doi: 10.1073/pnas.221198698. [PMID: 11592979]
S Bony, A Durix, A Leblond, P Jaussaud. Toxicokinetics of ergovaline in the horse after an intravenous administration. Veterinary research. 2001 Sep; 32(5):509-13. doi: 10.1051/vetres:2001142. [PMID: 11592620]
A E Salvat, H M Godoy. A simple thin-layer chromatographic method for the detection of ergovaline in leaf sheaths of tall fescue (Festuca arundinacea) infected with Neotyphodium coenophialum. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2001 Sep; 13(5):446-9. doi: 10.1177/104063870101300518. [PMID: 11580073]
J T Hovermale, A M Craig. Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne). Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2001 Jul; 13(4):323-7. doi: 10.1177/104063870101300407. [PMID: 11478604]
J Tor-Agbidye, L L Blythe, A M Craig. Correlation of endophyte toxins (ergovaline and lolitrem B) with clinical disease: fescue foot and perennial ryegrass staggers. Veterinary and human toxicology. 2001 Jun; 43(3):140-6. doi: ". [PMID: 11383653]
I J Lean. Association between feeding perennial ryegrass (Lolium perenne cultivar Grasslands impact) containing high concentrations of ergovaline, and health and productivity in a herd of lactating dairy cows. Australian veterinary journal. 2001 Apr; 79(4):262-4. doi: 10.1111/j.1751-0813.2001.tb11978.x. [PMID: 11349413]
A Durix, P Jaussaud, P Garcia, Y Bonnaire, S Bony. Analysis of ergovaline in milk using high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. B, Biomedical sciences and applications. 1999 Jun; 729(1-2):255-63. doi: 10.1016/s0378-4347(99)00166-8. [PMID: 10410950]
R L Rice, G G Schurig, D J Blodgett. Evaluation of physiologic indices in mice vaccinated with protein-ergotamine conjugates and fed an endophyte-infected fescue diet. American journal of veterinary research. 1998 Oct; 59(10):1258-62. doi: . [PMID: 9781458]
P Jaussaud, A Durix, B Videmann, A Vigié, S Bony. Rapid analysis of ergovaline in ovine plasma using high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. A. 1998 Jul; 815(1):147-53. doi: 10.1016/s0021-9673(98)00002-8. [PMID: 9718715]
D L Rankins. Metoclopramide and (or) cimetidine administration to sheep fed tall fescue. Veterinary and human toxicology. 1996 Jun; 38(3):173-6. doi: NULL. [PMID: 8727213]
J K Porter. Analysis of endophyte toxins: fescue and other grasses toxic to livestock. Journal of animal science. 1995 Mar; 73(3):871-80. doi: 10.2527/1995.733871x. [PMID: 7608022]
B T Larson, D M Sullivan, M D Samford, M S Kerley, J A Paterson, J T Turner. D2 dopamine receptor response to endophyte-infected tall fescue and an antagonist in the rat. Journal of animal science. 1994 Nov; 72(11):2905-10. doi: 10.2527/1994.72112905x. [PMID: 7730184]
A M Cràig, D Bilich, J T Hovermale, R E Welty. Improved extraction and HPLC methods for ergovaline from plant material and rumen fluid. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 1994 Jul; 6(3):348-52. doi: 10.1177/104063879400600311. [PMID: 7948205]
M M Stamm, T DelCurto, M R Horney, S D Brandyberry, R K Barton. Influence of alkaloid concentration of tall fescue straw on the nutrition, physiology, and subsequent performance of beef steers. Journal of animal science. 1994 Apr; 72(4):1068-75. doi: 10.2527/1994.7241068x. [PMID: 8014142]
K M Mizinga, F N Thompson, J A Stuedemann, G L Edwards. Neural dopamine D2 receptors in rats fed endophyte-infected fescue seed. Drug and chemical toxicology. 1993; 16(3):307-19. doi: 10.3109/01480549309081822. [PMID: 8404549]
C G Aldrich, M T Rhodes, J L Miner, M S Kerley, J A Paterson. The effects of endophyte-infected tall fescue consumption and use of a dopamine antagonist on intake, digestibility, body temperature, and blood constituents in sheep. Journal of animal science. 1993 Jan; 71(1):158-63. doi: 10.2527/1993.711158x. [PMID: 8454539]
C G Aldrich, J A Paterson, J L Tate, M S Kerley. The effects of endophyte-infected tall fescue consumption on diet utilization and thermal regulation in cattle. Journal of animal science. 1993 Jan; 71(1):164-70. doi: 10.2527/1993.711164x. [PMID: 8454540]