(1S,19S,22S,31S,33S,36R)-22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-enyl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.02,17.04,16.07,15.09,13.022,36.023,25.023,33.026,31]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one (BioDeep_00000903167)

代谢物信息卡片

(1S,19S,22S,31S,33S,36R)-22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-enyl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.02,17.04,16.07,15.09,13.022,36.023,25.023,33.026,31]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one

化学式: C42H55NO7 (685.3978319999999)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 98.77%

分子结构信息

SMILES: CC(=CC1OC2C(C(O1)(C)C)OC3CCC4(C5(C(CCC4(C36C2O6)O)CC7=C5NC8=C7C9=C(C=C8)C(=O)C1C(C9)C(OC1(C)C)(C)C)C)C)C
InChI: InChI=1S/C42H55NO7/c1-20(2)17-28-47-32-34(38(7,8)48-28)46-27-14-15-39(9)40(10)21(13-16-41(39,45)42(27)35(32)49-42)18-24-29-23-19-25-30(37(5,6)50-36(25,3)4)31(44)22(23)11-12-26(29)43-33(24)40/h11-12,17,21,25,27-28,30,32,34-35,43,45H,13-16,18-19H2,1-10H3/t21-,25?,27-,28?,30?,32?,34-,35?,39+,40+,41-,42?/m0/s1

描述信息

同义名列表

1 个代谢物同义名

数据库引用编号

1 个数据库交叉引用编号

PubChem: 91820047

分类词条

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

lolitrem B biosynthesis: O₂ + a reduced [NADPH-hemoprotein reductase] + paspaline ⟶ H₂O + an oxidized [NADPH-hemoprotein reductase] + terpendole E

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。

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]
Priyanka Reddy, Aaron Elkins, Joanne Hemsworth, Kathryn Guthridge, Simone Vassiliadis, Elizabeth Read, German Spangenberg, Simone Rochfort. Identification and Distribution of Novel Metabolites of Lolitrem B in Mice by High-Resolution Mass Spectrometry. Molecules (Basel, Switzerland). 2020 Jan; 25(2):. doi: 10.3390/molecules25020372. [PMID: 31963254]
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]
M D Combs, S H Edwards, J M Scherpenhuizen, E J Narayan, A E Kessell, J Ramsay, J Piltz, S R Raidal, J C Quinn. Treatment with potassium bromide mitigates ataxia and reduces tremor in lambs with perennial ryegrass toxicosis. New Zealand veterinary journal. 2019 Nov; 67(6):287-294. doi: 10.1080/00480169.2019.1637300. [PMID: 31248334]
Priyanka Reddy, Simone Rochfort, Elizabeth Read, Myrna Deseo, Emily Jaehne, Maarten Van Den Buuse, Kathryn Guthridge, Martin Combs, German Spangenberg, Jane Quinn. Tremorgenic effects and functional metabolomics analysis of lolitrem B and its biosynthetic intermediates. Scientific reports. 2019 06; 9(1):9364. doi: 10.1038/s41598-019-45170-7. [PMID: 31249318]
M D Combs, S H Edwards, J M Scherpenhuizen, E J Narayan, A E Kessell, J Piltz, S R Raidal, J Ramsay, J C Quinn. Development of a model for investigation of perennial ryegrass toxicosis in sheep. New Zealand veterinary journal. 2018 Nov; 66(6):281-289. doi: 10.1080/00480169.2018.1492986. [PMID: 29949720]
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]
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]
Carla J Eaton, Pierre-Yves Dupont, Peter Solomon, William Clayton, Barry Scott, Murray P Cox. A Core Gene Set Describes the Molecular Basis of Mutualism and Antagonism in Epichloë spp. Molecular plant-microbe interactions : MPMI. 2015 Mar; 28(3):218-31. doi: 10.1094/mpmi-09-14-0293-fi. [PMID: 25496592]
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]
J E Dalziel, K E Dunstan, S C Finch. Combined effects of fungal alkaloids on intestinal motility in an in vitro rat model. Journal of animal science. 2013 Nov; 91(11):5177-82. doi: 10.2527/jas.2013-6449. [PMID: 23989880]
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]
Kimberley J May, Michelle K Bryant, Xiuwen Zhang, Barbara Ambrose, Barry Scott. Patterns of expression of a lolitrem biosynthetic gene in the Epichloë festucae-perennial ryegrass symbiosis. Molecular plant-microbe interactions : MPMI. 2008 Feb; 21(2):188-97. doi: 10.1094/mpmi-21-2-0188. [PMID: 18184063]
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]
Shigeru Miyazaki, Ikumi Ishizaki, Masumi Ishizaka, Tadashi Kanbara, Yuriko Ishiguro-Takeda. Lolitrem B residue in fat tissues of cattle consuming endophyte-infected perennial ryegrass straw. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2004 Jul; 16(4):340-2. doi: 10.1177/104063870401600416. [PMID: 15305749]
M Holzhauer, A C Westerhout. [Young perennial ryegrass staggers in a dairy herd]. Tijdschrift voor diergeneeskunde. 2004 May; 129(9):298-300. doi: ". [PMID: 15156654]
S Miyazaki, M Fukumura, M Yoshioka, N Yamanaka. Detection of endophyte toxins in the imported perennial ryegrass straw. The Journal of veterinary medical science. 2001 Sep; 63(9):1013-5. doi: 10.1292/jvms.63.1013. [PMID: 11642270]
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]
M M Sloet van Oldruitenborgh-Oosterbaan, F C Schipper, L S Goehring, J F Gremmels. [Rhinopneumonia or mycotoxin intoxication? Neurologic phenomena in horses from a riding school]. Tijdschrift voor diergeneeskunde. 1999 Nov; 124(22):679-81. doi: NULL. [PMID: 10596400]
J A Humble. The biologic production unit for food animal veterinarians. Journal of the American Veterinary Medical Association. 1996 Nov; 209(10):1698-9. doi: ". [PMID: 8921021]
E G Pearson, C B Andreasen, L L Blythe, A M Craig. Atypical pneumonia associated with ryegrass staggers in calves. Journal of the American Veterinary Medical Association. 1996 Sep; 209(6):1137-42. doi: ". [PMID: 8800265]
G J van Essen, M Blom, J Fink Gremmels-Gehrmann. [Ryegrass cramps in horses]. Tijdschrift voor diergeneeskunde. 1995 Dec; 120(24):710-1. doi: ". [PMID: 8553345]
B L Munday, I M Monkhouse, R T Gallagher. Intoxication of horses by lolitrem B in ryegrass seed cleanings. Australian veterinary journal. 1985 Jun; 62(6):207. doi: 10.1111/j.1751-0813.1985.tb07306.x. [PMID: 4062734]
R T Gallagher, A D Hawkes. High-performance liquid chromatography with stop-flow ultraviolet spectral characterization of lolitrem neurotoxins from perennial ryegrass. Journal of chromatography. 1985 Mar; 322(1):159-67. doi: 10.1016/s0021-9673(01)97668-x. [PMID: 3988848]
R T Gallagher, A D Hawkes, J M Stewart. Rapid determination of the neurotoxin lolitrem B in perennial ryegrass by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. 1985 Mar; 321(1):217-26. doi: 10.1016/s0021-9673(01)90438-8. [PMID: 3988840]
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