grayanotoxin I (BioDeep_00000407356)

 

Secondary id: BioDeep_00000003850, BioDeep_00000176254

natural product PANOMIX_OTCML-2023


代谢物信息卡片


grayanotoxin I

化学式: C22H36O7 (412.2460906)
中文名称: 杜鹃毒素
谱图信息: 最多检出来源 Homo sapiens(blood) 3%

分子结构信息

SMILES: CC(=O)OC1C2CCC3C1(CC(C4(C(C3(C)O)CC(C4(C)C)O)O)O)CC2(C)O
InChI: InChI=1S/C22H36O7/c1-11(23)29-17-12-6-7-13-20(5,27)14-8-15(24)18(2,3)22(14,28)16(25)9-21(13,17)10-19(12,4)26/h12-17,24-28H,6-10H2,1-5H3/t12-,13+,14+,15+,16-,17-,19-,20-,21+,22+/m1/s1

描述信息

A tetracyclic diterpenoid that is grayanotoxane in which the pro-R hydrogen at position 14 is substituted by an acetoxy group and in which the 3beta-, 5-, 6beta-, 10-, and 16- positions are substituted by hydroxy groups.
D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents

同义名列表

1 个代谢物同义名

grayanotoxin I



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。



文献列表

  • Róisín Fattorini, Paul A Egan, James Rosindell, Iain W Farrell, Philip C Stevenson. Grayanotoxin I variation across tissues and species of Rhododendron suggests pollinator-herbivore defence trade-offs. Phytochemistry. 2023 Aug; 212(?):113707. doi: 10.1016/j.phytochem.2023.113707. [PMID: 37149121]
  • Yi Zhou, Yong-Mei Wu, Rong Fan, Jiang Ouyang, Xiao-Long Zhou, Zi-Bo Li, Muhammad Usman Janjua, Hai-Gang Li, Mei-Hua Bao, Bin-Sheng He. Transcriptome analysis unveils the mechanisms of lipid metabolism response to grayanotoxin I stress in Spodoptera litura. PeerJ. 2023; 11(?):e16238. doi: 10.7717/peerj.16238. [PMID: 38077416]
  • Na Sun, Guijuan Zheng, Meijun He, Yuanyuan Feng, Junjun Liu, Meicheng Wang, Hanqi Zhang, Junfei Zhou, Guangmin Yao. Grayanane Diterpenoids from the Leaves of Rhododendron auriculatum and Their Analgesic Activities. Journal of natural products. 2019 07; 82(7):1849-1860. doi: 10.1021/acs.jnatprod.9b00095. [PMID: 31246460]
  • Na Sun, Yue Qiu, Yan Zhu, Junjun Liu, Hanqi Zhang, Qihua Zhang, Mengke Zhang, Guijuan Zheng, Chun Zhang, Guangmin Yao. Rhodomicranosides A-I, analgesic diterpene glucosides with diverse carbon skeletons from Rhododendron micranthum. Phytochemistry. 2019 Feb; 158(?):1-12. doi: 10.1016/j.phytochem.2018.10.017. [PMID: 30445297]
  • Hannah Pischon, Anne Petrick, Matthias Müller, Nils Köster, Jörg Pietsch, Lars Mundhenk. Grayanotoxin I Intoxication in Pet Pigs. Veterinary pathology. 2018 11; 55(6):896-899. doi: 10.1177/0300985818789482. [PMID: 30071802]
  • Hong Lak Choi, Kyung Hye Park, Jung Soo Park, Hye Young Choi, Hoon Kim, Sun Moon Kim. Relationship between blood toxin level and clinical features in patients with grayanotoxin poisoning - six clinical cases. Clinical toxicology (Philadelphia, Pa.). 2017 Nov; 55(9):991-995. doi: 10.1080/15563650.2017.1331448. [PMID: 28594250]
  • S Silici, Z Doğan, H Sahin, T Atayoğlu, B Yakan. Acute effects of grayanotoxin in rhododendron honey on kidney functions in rats. Environmental science and pollution research international. 2016 Feb; 23(4):3300-9. doi: 10.1007/s11356-015-5534-z. [PMID: 26490905]
  • Anna Dampc, Maria Luczkiewicz. Labrador tea--the aromatic beverage and spice: a review of origin, processing and safety. Journal of the science of food and agriculture. 2015 Jun; 95(8):1577-83. doi: 10.1002/jsfa.6889. [PMID: 25156477]
  • Ali Aygun, Abdulkadir Gunduz, Suleyman Turedi, Suha Turkmen, Yunus Karaca, Faik Ahmet Ayaz, Su Youn Ahn, Suncheun Kim. Examination using LC-MS/MS determination of grayanotoxin levels in blood, urine, and honey consumed by patients presenting to the emergency department with mad honey intoxication and relations with clinical data: a preliminary study. Annals of Saudi medicine. 2015 Mar; 35(2):161-4. doi: 10.5144/0256-4947.2015.161. [PMID: 26336024]
  • Caitlin J Oliver, Samantha Softley, Sally M Williamson, Philip C Stevenson, Geraldine A Wright. Pyrethroids and Nectar Toxins Have Subtle Effects on the Motor Function, Grooming and Wing Fanning Behaviour of Honeybees (Apis mellifera). PloS one. 2015; 10(8):e0133733. doi: 10.1371/journal.pone.0133733. [PMID: 26280999]
  • Anja These, Dorina Bodi, Samuel Uecker, Katharina Reimers, Stefan Ronczka, Angelika Preiss-Weigert, Monika Lahrssen-Wiederholt. A case of human poisoning by grayanotoxins following honey ingestion: elucidation of the toxin profile by mass spectrometry. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(10):1674-84. doi: 10.1080/19440049.2015.1042410. [PMID: 25906176]
  • Karyn Bischoff, Mary C Smith, Samuel Stump. Treatment of pieris ingestion in goats with intravenous lipid emulsion. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2014 Dec; 10(4):411-4. doi: 10.1007/s13181-014-0426-z. [PMID: 25193885]
  • Matthias Lechtenberg, Frauke Dierks, Jandirk Sendker, Andrea Louis, Hartwig Schepker, Andreas Hensel. Extracts from Rhododendron ferrugineum do not exhibit grayanotoxin I: an analytical survey on grayanotoxin I within the genus Rhododendron. Planta medica. 2014 Oct; 80(15):1321-8. doi: 10.1055/s-0034-1383039. [PMID: 25215540]
  • S Yaylaci, I Kocayigit, E Aydin, A Osken, A B Genc, M A Cakar, A Tamer. Clinical and laboratory findings in mad honey poisoning: a single center experience. Nigerian journal of clinical practice. 2014 Sep; 17(5):589-93. doi: 10.4103/1119-3077.141424. [PMID: 25244269]
  • Suze A Jansen, Iris Kleerekooper, Zonne L M Hofman, Isabelle F P M Kappen, Anna Stary-Weinzinger, Marcel A G van der Heyden. Grayanotoxin poisoning: 'mad honey disease' and beyond. Cardiovascular toxicology. 2012 Sep; 12(3):208-15. doi: 10.1007/s12012-012-9162-2. [PMID: 22528814]
  • Rupert L Hough, Colin Crews, Duncan White, Malcolm Driffield, Colin D Campbell, Charlotte Maltin. Degradation of yew, ragwort and rhododendron toxins during composting. The Science of the total environment. 2010 Sep; 408(19):4128-37. doi: 10.1016/j.scitotenv.2010.05.024. [PMID: 20579691]
  • Wei Dong Zhang, Hui Zi Jin, Gang Chen, Xue Feng Li, Shi Kai Yan, Lu Zhang, Yun Heng Shen, Ming Yang. A new grayanane diterpenoid from Rhododendron decorum. Fitoterapia. 2008 Dec; 79(7-8):602-4. doi: 10.1016/j.fitote.2008.04.009. [PMID: 18634858]
  • W T Poon, C H Ho, K L Yip, C K Lai, K L Cheung, Rita Y T Sung, Albert Y W Chan, Tony W L Mak. Grayanotoxin poisoning from Rhododendron simsii in an infant. Hong Kong medical journal = Xianggang yi xue za zhi. 2008 Oct; 14(5):405-7. doi: NULL. [PMID: 18840915]
  • Abdulkadir Gunduz, Suleyman Turedi, Robert M Russell, Faik Ahmet Ayaz. Clinical review of grayanotoxin/mad honey poisoning past and present. Clinical toxicology (Philadelphia, Pa.). 2008 Jun; 46(5):437-42. doi: 10.1080/15563650701666306. [PMID: 18568799]
  • Abdulkadir Gunduz, Suleyman Turedi, Hukum Uzun, Murat Topbas. Mad honey poisoning. The American journal of emergency medicine. 2006 Sep; 24(5):595-8. doi: 10.1016/j.ajem.2006.01.022. [PMID: 16938599]
  • T Kimura, K Yamaoka, E Kinoshita, H Maejima, T Yuki, M Yakehiro, I Seyama. Novel site on sodium channel alpha-subunit responsible for the differential sensitivity of grayanotoxin in skeletal and cardiac muscle. Molecular pharmacology. 2001 Oct; 60(4):865-72. doi: . [PMID: 11562450]
  • T Yuki, K Yamaoka, M Yakehiro, I Seyama. State-dependent action of grayanotoxin I on Na(+) channels in frog ventricular myocytes. The Journal of physiology. 2001 Aug; 534(Pt 3):777-90. doi: 10.1111/j.1469-7793.2001.00777.x. [PMID: 11483708]
  • D M Holstege, B Puschner, T Le. Determination of grayanotoxins in biological samples by LC-MS/MS. Journal of agricultural and food chemistry. 2001 Mar; 49(3):1648-51. doi: 10.1021/jf000750s. [PMID: 11312909]
  • B Puschner, D M Holstege, N Lamberski. Grayanotoxin poisoning in three goats. Journal of the American Veterinary Medical Association. 2001 Feb; 218(4):573-5, 527. doi: 10.2460/javma.2001.218.573. [PMID: 11229512]
  • T Furue, M Yakehiro, I Seyama. Differential effects of lipid-soluble toxins on sodium channels and L-type calcium channels in frog ventricular cells. Hiroshima journal of medical sciences. 1997 Mar; 46(1):43-50. doi: ". [PMID: 9114566]
  • D S Duch, A Hernandez, S R Levinson, B W Urban. Grayanotoxin-I-modified eel electroplax sodium channels. Correlation with batrachotoxin and veratridine modifications. The Journal of general physiology. 1992 Oct; 100(4):623-45. doi: 10.1085/jgp.100.4.623. [PMID: 1334121]
  • K H Plumlee, W G VanAlstine, J M Sullivan. Japanese pieris toxicosis of goats. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 1992 Jul; 4(3):363-4. doi: 10.1177/104063879200400330. [PMID: 1515506]
  • S B Power, P G O'Donnell, E G Quirk. Pieris poisoning in sheep. The Veterinary record. 1991 Jun; 128(25):599-600. doi: 10.1136/vr.128.25.599. [PMID: 1897095]
  • R D Hollands, M C Hughes. Pieris formosanum poisoning in the goat. The Veterinary record. 1986 Apr; 118(14):407-8. doi: 10.1136/vr.118.14.407. [PMID: 3716102]
  • D J Humphreys, J B Stodulski. Detection of andromedotoxins for the diagnosis of Rhododendron poisoning in animals. Journal of applied toxicology : JAT. 1986 Apr; 6(2):121-2. doi: 10.1002/jat.2550060210. [PMID: 3700960]
  • L J Liu. [Seasonal variations of several important constituents in the leaves of Rhododendron przewalskii]. Zhong yao tong bao (Beijing, China : 1981). 1986 Jan; 11(1):41-3. doi: ". [PMID: 2943460]
  • D J Humphreys, J B Stodulski, J G Stocker. Rhododendron poisoning in goats. The Veterinary record. 1983 Nov; 113(21):503-4. doi: 10.1136/vr.113.21.503. [PMID: 6649397]
  • L A van Leengoed, J J van Amerongen. [Rhododendron poisoning: clinical aspects, treatment and course in a herd of sheep]. Tijdschrift voor diergeneeskunde. 1983 Jan; 108(1):41-2. doi: ". [PMID: 6868052]
  • M Lazdunski, J F Renaud. The action of cardiotoxins on cardiac plasma membranes. Annual review of physiology. 1982; 44(?):463-73. doi: 10.1146/annurev.ph.44.030182.002335. [PMID: 6280589]
  • H Y Mao, Y S Tu, F D Nei, G F Liang, Y B Feng. Rapid antihypertensive effect of rhomotoxin in 105 hypertension cases. Chinese medical journal. 1981 Nov; 94(11):733-6. doi: ". [PMID: 6800715]
  • T Narahashi, I Seyama. Mechanism of nerve membrane depolarization caused by grayanotoxin I. The Journal of physiology. 1974 Oct; 242(2):471-87. doi: 10.1113/jphysiol.1974.sp010718. [PMID: 4455829]
  • K HASHIMOTO, S KUMAKURA, N TAIRA. VASCULAR REFLEX RESPONSES INDUCED BY AN INTRAARTERIAL INJECTION OF AZAAZEPINOPHENOTHIAZINE, ANDROMEDOTOXIN, VERATRIDINE, BRADYKININ AND KALLIKREIN AND BLOCKING ACTION OF SODIUM SALICYLATE. The Japanese journal of physiology. 1964 Jun; 14(?):299-308. doi: 10.2170/jjphysiol.14.299. [PMID: 14187438]
  • M KOHANAWA. Pharmacological studies on rhodotoxin isolated from Rhododendron hymenanthes and andromedotoxin isolated from Andromeda japonica, Thunberg. Japanese journal of pharmacology. 1956 Sep; 6(1):46-56. doi: 10.1254/jjp.6.46. [PMID: 13415780]