ecdysone (BioDeep_00000004433)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


17-(3,6-dihydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

化学式: C27H44O6 (464.3137724)
中文名称: 蜕皮激素
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.02%

分子结构信息

SMILES: C12=CC([C@]3([H])C[C@@H](O)[C@@H](O)C[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2(O)CC[C@@]1([C@H](C)[C@H](O)CCC(O)(C)C)[H])=O
InChI: InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1

描述信息

A 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
Ecdysone, also known as molting hormone, belongs to pentahydroxy bile acids, alcohols and derivatives class of compounds. Those are bile acids, alcohols or derivatives bearing five hydroxyl groups. Thus, ecdysone is considered to be a sterol lipid molecule. Ecdysone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ecdysone can be synthesized from 5beta-cholestane. Ecdysone is also a parent compound for other transformation products, including but not limited to, (25R)-11alpha,20,26-trihydroxyecdysone, (24R)-11alpha,20,24-trihydroxyecdysone, and ecdysone 25-O-D-glucopyranoside. Ecdysone can be found in spinach, which makes ecdysone a potential biomarker for the consumption of this food product. Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in Chris Q. Doe lab have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells. Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have been reputed to have medicinal value and are part of herbal adaptogenic remedies like Cordyceps, yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids .
Ecdysone (α-Ecdysone), a major steroid hormone in insects and herbs, triggers mineralocorticoid receptor (MR) activation and induces cellular apoptosis. Ecdysone plays essential roles in coordinating developmental transitions and homeostatic sleep regulation through its active metabolite 20-hydroxyecdysone (Crustecdysone; 20E; HY-N6979)[1][2].

同义名列表

7 个代谢物同义名

ecdysone; (22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one; 2beta,3beta,14alpha,22R,25-pentahydroxy-5beta-cholest-7-en-6-one; ST 27:2;O6; 17-(3,6-dihydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one; α-Ecdysone; Ecdysone



数据库引用编号

18 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

187 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

  • Sharath Chandra Gaddelapati, Smitha George, Anilkumar Moola, Karthi Sengodan, Subba Reddy Palli. N(alpha)-acetyltransferase 40-mediated histone acetylation plays an important role in ecdysone regulation of metamorphosis in the red flour beetle, Tribolium castaneum. Communications biology. 2024 May; 7(1):521. doi: 10.1038/s42003-024-06212-7. [PMID: 38702540]
  • Xiao-Qing Zhang, Lin Jin, Wen-Chao Guo, Kai-Yun Fu, Guo-Qing Li. RNA Interference-Mediated Suppression of Ecdysone Signaling Inhibits Choriogenesis in Two Coleoptera Species. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084555. [PMID: 38674140]
  • Xiaoyang Li, Jiedan Xiao, Xiaoqin Cheng, Hongyu Zhang, Weiwei Zheng. Nanomaterial-encapsulated dsRNA of ecdysone-induced early gene E75, a potential RNAi-based SIT strategy for pest control against Bactrocera dorsalis. International journal of biological macromolecules. 2024 Apr; 263(Pt 1):130607. doi: 10.1016/j.ijbiomac.2024.130607. [PMID: 38447848]
  • Zhishan Cao, Olha Bakumenko, Volodymyr Vlasenko, Weihai Li, Jinjun Cao. Molecular characterization and functional analysis of the ecdysone receptor isoform (EcR) from the oriental fruit moth Grapholita molesta (Lepidoptera: Tortricidae). Archives of insect biochemistry and physiology. 2024 Apr; 115(4):e22110. doi: 10.1002/arch.22110. [PMID: 38605666]
  • Tong Hao, Zhentao Song, Mingzhi Zhang, Lingrui Zhang, Jiarui Yang, Jingjing Li, Jinsheng Sun. Reconstruction of Metabolic-Protein Interaction Integrated Network of Eriocheir sinensis and Analysis of Ecdysone Synthesis. Genes. 2024 Mar; 15(4):. doi: 10.3390/genes15040410. [PMID: 38674345]
  • Dan-Qian Geng, Xue-Li Wang, Xiang-Yang Lyu, Alexander S Raikhel, Zhen Zou. Ecdysone-controlled nuclear receptor ERR regulates metabolic homeostasis in the disease vector mosquito Aedes aegypti. PLoS genetics. 2024 Mar; 20(3):e1011196. doi: 10.1371/journal.pgen.1011196. [PMID: 38466721]
  • Zhiming Yang, Mengqing Deng, Wenxiu Wang, Tianxiang Xiao, Haoxue Peng, Zifan Huang, Kai Lu. Characterization and functional analysis of UDP-glycosyltransferases reveal their contribution to phytochemical flavone tolerance in Spodoptera litura. International journal of biological macromolecules. 2024 Jan; 261(Pt 1):129745. doi: 10.1016/j.ijbiomac.2024.129745. [PMID: 38286378]
  • Du-Yeol Choi, Hyoung-Ho Mo, Youngjin Park. Different development and fecundity between Spodoptera frugiperda USA and China populations, influenced by ecdysone-related genes. Archives of insect biochemistry and physiology. 2024 Jan; 115(1):e22074. doi: 10.1002/arch.22074. [PMID: 38288488]
  • Benshui Shu, Yanzheng Lin, Yuting Huang, Luyang Liu, Xueming Cai, Jintian Lin, Jingjing Zhang. Characterization and transcriptomic analyses of the toxicity induced by toosendanin in Spodoptera frugipreda. Gene. 2023 Oct; 893(?):147928. doi: 10.1016/j.gene.2023.147928. [PMID: 37898452]
  • Yongjun Li, Paula Haynes, Shirley L Zhang, Zhifeng Yue, Amita Sehgal. Ecdysone acts through cortex glia to regulate sleep in Drosophila. eLife. 2023 01; 12(?):. doi: 10.7554/elife.81723. [PMID: 36719183]
  • Sakhawat Shah, Su-Su Zhang, Karam Khamis Elgizawy, Wen-Han Yan, Ning Tang, Gang Wu, Feng-Lian Yang. Diallyl trisulfide reduced the reproductive capacity of male Sitotroga cerealella via the regulation of juvenile and ecdysone hormones. Ecotoxicology and environmental safety. 2022 Dec; 248(?):114304. doi: 10.1016/j.ecoenv.2022.114304. [PMID: 36403303]
  • Gary N Landis, Sebastian Ko, Oscar Peng, Brett Bognar, Michael Khmelkov, Hans S Bell, John Tower. A screen of small molecule and genetic modulators of life span in female Drosophila identifies etomoxir, RH5849 and unanticipated temperature effects. Fly. 2022 12; 16(1):397-413. doi: 10.1080/19336934.2022.2149209. [PMID: 36412257]
  • Kaizun Xu, Huangli Lan, Chunhui He, Yuting Wei, Qingyu Lu, Kunpei Cai, Dongliang Yu, Xingcan Yin, Yizhe Li, Jiachen Lv. Toxicological effects of trace amounts of pyriproxyfen on the midgut of non-target insect silkworm. Pesticide biochemistry and physiology. 2022 Nov; 188(?):105266. doi: 10.1016/j.pestbp.2022.105266. [PMID: 36464371]
  • Gui-Yun Li, Xiao-Jing Liu, Gang-Qi Fang, Jie Yang, Shuai Zhan, Mu-Wang Li. Functional characterization of a low-density lipoprotein receptor in the lepidopteran model, Bombyx mori. Insect science. 2022 Oct; 29(5):1262-1274. doi: 10.1111/1744-7917.13018. [PMID: 35411705]
  • Guang-Mao Shen, Shi-Yuan Ou, Chuan-Zhen Li, Kai-Yang Feng, Jin-Zhi Niu, Michael J Adang, Lin He. Transcription factors CncC and Maf connect the molecular network between pesticide resistance and resurgence of pest mites. Insect science. 2022 Jun; 29(3):801-816. doi: 10.1111/1744-7917.12970. [PMID: 34586709]
  • Xinwei Xiong, Yanfei Cao, Zhixin Li, Ronglian Huang, Xiaodong Du, Zhe Zheng. Ecdysone signal pathway participates in shell formation in pearl oysters Pinctada fucata martensii. The Journal of steroid biochemistry and molecular biology. 2022 03; 217(?):106045. doi: 10.1016/j.jsbmb.2021.106045. [PMID: 34915168]
  • Lang You, Zhiqian Li, Zhongjie Zhang, Bo Hu, Ye Yu, Fangying Yang, Anjiang Tan. Two dehydroecdysone reductases act as fat body-specific 20E catalyzers in Bombyx mori. Insect science. 2022 Feb; 29(1):100-110. doi: 10.1111/1744-7917.12928. [PMID: 34018323]
  • Zhong-Jie Zhang, Xiao-Jing Liu, Ye Yu, Fang-Ying Yang, Kai Li. The receptor tyrosine kinase torso regulates ecdysone homeostasis to control developmental timing in Bombyx mori. Insect science. 2021 Dec; 28(6):1582-1590. doi: 10.1111/1744-7917.12879. [PMID: 33205532]
  • Miwako Toyofuku, Daiki Fujinaga, Kazue Inaba, Tomoki Funahashi, Yuuta Fujikawa, Hideshi Inoue, Hiroshi Kataoka, Ryusuke Niwa, Hajime Ono. The plant-derived triterpenoid, cucurbitacin B, but not cucurbitacin E, inhibits the developmental transition associated with ecdysone biosynthesis in Drosophila melanogaster. Journal of insect physiology. 2021 10; 134(?):104294. doi: 10.1016/j.jinsphys.2021.104294. [PMID: 34389412]
  • Bat-Erdene Jugder, Layla Kamareddine, Paula I Watnick. Microbiota-derived acetate activates intestinal innate immunity via the Tip60 histone acetyltransferase complex. Immunity. 2021 08; 54(8):1683-1697.e3. doi: 10.1016/j.immuni.2021.05.017. [PMID: 34107298]
  • Mathilde Latil, Serge Camelo, Stanislas Veillet, René Lafont, Pierre J Dilda. Developing new drugs that activate the protective arm of the renin-angiotensin system as a potential treatment for respiratory failure in COVID-19 patients. Drug discovery today. 2021 05; 26(5):1311-1318. doi: 10.1016/j.drudis.2021.02.010. [PMID: 33609783]
  • Z-M Yang, N Yu, S-J Wang, S K Korai, Z-W Liu. Characterization of ecdysteroid biosynthesis in the pond wolf spider, Pardosa pseudoannulata. Insect molecular biology. 2021 02; 30(1):71-80. doi: 10.1111/imb.12678. [PMID: 33131130]
  • Shuang Guo, Zhong Tian, Qing-Wen Wu, Kirst King-Jones, Wen Liu, Fen Zhu, Xiao-Ping Wang. Steroid hormone ecdysone deficiency stimulates preparation for photoperiodic reproductive diapause. PLoS genetics. 2021 02; 17(2):e1009352. doi: 10.1371/journal.pgen.1009352. [PMID: 33529191]
  • Tsai-Chi Shang Kuan, Roger K Prichard. Developmental regulation of Dirofilaria immitis microfilariae and evaluation of ecdysone signaling pathway transcript level using droplet digital PCR. Parasites & vectors. 2020 Dec; 13(1):614. doi: 10.1186/s13071-020-04480-w. [PMID: 33298156]
  • Wei Luo, Li-Xia Huang, Shuang-Kang Qin, Xian Zhang, Qi-Li Feng, Jun Gu, Li-Hua Huang. Multiple microRNAs control ecdysone signaling in the midgut of Spodoptera litura. Insect science. 2020 Dec; 27(6):1208-1223. doi: 10.1111/1744-7917.12745. [PMID: 31840397]
  • Shu Huang, Qilin Yi, Xingye Lian, Siqi Xu, Chuanyan Yang, Jiejie Sun, Lingling Wang, Linsheng Song. The involvement of ecdysone and ecdysone receptor in regulating the expression of antimicrobial peptides in Chinese mitten crab, Eriocheir sinensis. Developmental and comparative immunology. 2020 10; 111(?):103757. doi: 10.1016/j.dci.2020.103757. [PMID: 32485180]
  • Zulian Liu, Jun Xu, Lin Ling, Xingyu Luo, Dehong Yang, Xu Yang, Xiaoqian Zhang, Yongping Huang. miR-34 regulates larval growth and wing morphogenesis by directly modulating ecdysone signalling and cuticle protein in Bombyx mori. RNA biology. 2020 09; 17(9):1342-1351. doi: 10.1080/15476286.2020.1767953. [PMID: 32401141]
  • S Ramos, F Chelemen, V Pagone, N Elshaer, P Irles, M D Piulachs. Eyes absent in the cockroach panoistic ovaries regulates proliferation and differentiation through ecdysone signalling. Insect biochemistry and molecular biology. 2020 08; 123(?):103407. doi: 10.1016/j.ibmb.2020.103407. [PMID: 32417417]
  • Jianli Duan, Yunpo Zhao, Haichao Li, Lukas Habernig, Michael D Gordon, Xuexia Miao, Ylva Engström, Sabrina Büttner. Bab2 Functions as an Ecdysone-Responsive Transcriptional Repressor during Drosophila Development. Cell reports. 2020 07; 32(4):107972. doi: 10.1016/j.celrep.2020.107972. [PMID: 32726635]
  • Wenjing Zheng, Karen Ocorr, Marc Tatar. Extracellular matrix induced by steroids and aging through a G-protein-coupled receptor in a Drosophila model of renal fibrosis. Disease models & mechanisms. 2020 06; 13(6):. doi: 10.1242/dmm.041301. [PMID: 32461236]
  • Liu Yang, Hai Jiang, Meiling Yan, Xudong Xing, Xinyue Guo, Wenjing Man, Ajiao Hou, Bingyou Yang, Qiuhong Wang, Haixue Kuang. Comparison of pharmacokinetics of phytoecdysones and triterpenoid saponins of monomer, crude and processed Radix Achyranthis Bidentatae by UHPLC-MS/MS. Xenobiotica; the fate of foreign compounds in biological systems. 2020 Jun; 50(6):677-684. doi: 10.1080/00498254.2019.1579946. [PMID: 30729838]
  • Naoki Okamoto, Naoki Yamanaka. Steroid Hormone Entry into the Brain Requires a Membrane Transporter in Drosophila. Current biology : CB. 2020 01; 30(2):359-366.e3. doi: 10.1016/j.cub.2019.11.085. [PMID: 31928869]
  • Xiangkun Meng, Nan Zhang, Xuemei Yang, Lijun Miao, Heng Jiang, Caihong Ji, Beibei Xu, Kun Qian, Jianjun Wang. Sublethal effects of chlorantraniliprole on molting hormone levels and mRNA expressions of three Halloween genes in the rice stem borer, Chilo suppressalis. Chemosphere. 2020 Jan; 238(?):124676. doi: 10.1016/j.chemosphere.2019.124676. [PMID: 31473531]
  • Dona R Wisidagama, Stefan M Thomas, Geanette Lam, Carl S Thummel. Functional analysis of Aarf domain-containing kinase 1 in Drosophila melanogaster. Developmental dynamics : an official publication of the American Association of Anatomists. 2019 09; 248(9):762-770. doi: 10.1002/dvdy.66. [PMID: 31175694]
  • Kang He, Huamei Xiao, Yang Sun, Gongming Situ, Yu Xi, Fei Li. microRNA-14 as an efficient suppressor to switch off ecdysone production after ecdysis in insects. RNA biology. 2019 09; 16(9):1313-1325. doi: 10.1080/15476286.2019.1629768. [PMID: 31184522]
  • Monika Bhardwaj, Nilufar Z Mamadalieva, Anil Kumar Chauhan, Sun Chul Kang. α-Ecdysone suppresses inflammatory responses via the Nrf2 pathway in lipopolysaccharide-stimulated RAW 264.7 cells. International immunopharmacology. 2019 Aug; 73(?):405-413. doi: 10.1016/j.intimp.2019.05.038. [PMID: 31152978]
  • Juan Wang, Zhiyue Lv, Ziyan Lei, Zhaoyang Chen, Bo Lv, Huilin Yang, Zhi Wang, Qisheng Song. Expression and functional analysis of cytochrome P450 genes in the wolf spider Pardosa pseudoannulata under cadmium stress. Ecotoxicology and environmental safety. 2019 May; 172(?):19-25. doi: 10.1016/j.ecoenv.2019.01.034. [PMID: 30669070]
  • Xiao-Jing Wang, Qi Zhang, Yu-Ru Peng, Li Li, Jing Qu, Yun-Bao Liu, Song Xu, Shuang-Gang Ma, Yong Li, Zhong-Mei Zou, Ru-Bing Wang, Shi-Shan Yu. Two azafluoranthene alkaloids and a phytoecdysone from the stems of Cyclea barbata. Journal of Asian natural products research. 2019 Mar; 21(3):217-226. doi: 10.1080/10286020.2018.1564137. [PMID: 30739491]
  • Luc Swevers. An update on ecdysone signaling during insect oogenesis. Current opinion in insect science. 2019 02; 31(?):8-13. doi: 10.1016/j.cois.2018.07.003. [PMID: 31109678]
  • Minglei Lu, Pei Wang, Yan Ge, Lance Dworkin, Andrew Brem, Zhangsuo Liu, Rujun Gong. Activation of mineralocorticoid receptor by ecdysone, an adaptogenic and anabolic ecdysteroid, promotes glomerular injury and proteinuria involving overactive GSK3β pathway signaling. Scientific reports. 2018 08; 8(1):12225. doi: 10.1038/s41598-018-29483-7. [PMID: 30111886]
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  • Minglei Lu, Pei Wang, Sijie Zhou, Bryce Flickinger, Deepak Malhotra, Yan Ge, Marc Tatar, Lance Dworkin, Zhangsuo Liu, Rujun Gong. Ecdysone Elicits Chronic Renal Impairment via Mineralocorticoid-Like Pathogenic Activities. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 49(4):1633-1645. doi: 10.1159/000493499. [PMID: 30227391]
  • Sora Enya, Chikana Yamamoto, Hajime Mizuno, Tsuyoshi Esaki, Hsin-Kuang Lin, Masatoshi Iga, Kana Morohashi, Yota Hirano, Hiroshi Kataoka, Tsutomu Masujima, Yuko Shimada-Niwa, Ryusuke Niwa. Dual Roles of Glutathione in Ecdysone Biosynthesis and Antioxidant Function During Larval Development in Drosophila. Genetics. 2017 12; 207(4):1519-1532. doi: 10.1534/genetics.117.300391. [PMID: 29021278]
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