Glyceollin I (BioDeep_00000004743)

 

Secondary id: BioDeep_00000640975, BioDeep_00001868820

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol

化学式: C20H18O5 (338.1154178)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 1.11%

分子结构信息

SMILES: CC1(C)C=Cc2c(ccc3c2OCC2(O)c4ccc(O)cc4OC32)O1
InChI: InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3

描述信息

Glyceollin I is found in pulses. Phytoalexin from soybean seedlings.

同义名列表

22 个代谢物同义名

17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol; 2,2-Dimethyl-2H,6H-benzofuro[3,2-c]pyrano[2,3-H][1]benzopyran-6a,9(11ah)-diol, 9ci; 1-Mercapto-3-methylbutane; 3-methyl-1-butanethiol; 3-Methylbutane-1-thiol; 2-Methyl-4-butanethiol; 3-Methyl-1-butylthiol; 3-Methylbutanethiol; Isoamyl thioalcohol; Isoamyl sulfhydrate; Thioisoamyl alcohol; (-) - glyceollin I; Isoamyl mercaptan; (-)-Glyceollin I; rac-Glyceollin I; Isopentanethiol; ISOAMYLTHIOL; Glyceollin I; Glyceollin; FEMA 3858; Glyceollin; (-)-Glyceollin I



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

10 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(8)

  • glyceollin biosynthesis: (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + H+ + NADPH + O2 ⟶ H2O + NADP+ + glyceollin I
  • glyceollin biosynthesis: (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin I
  • glyceollin biosynthesis: (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin I
  • superpathway of pterocarpan biosynthesis (via daidzein): (6αS,11αS)-2-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin II
  • glyceollin biosynthesis: (6αS,11αS)-2-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin II
  • glyceollin biosynthesis: (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin I
  • superpathway of pterocarpan biosynthesis (via daidzein): 2,4',7-trihydroxyisoflavanone ⟶ H2O + daidzein
  • glyceollin biosynthesis: (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + glyceollin I

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 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

  • Ye Zhang, Chizumi Abe, Koji Ochiai, Toshiro Matsui. Tissue Distribution of Orally Administered Prenylated Isoflavones, Glyceollins, in Sprague-Dawley Rats. Journal of agricultural and food chemistry. 2021 Dec; 69(50):15165-15174. doi: 10.1021/acs.jafc.1c05208. [PMID: 34875172]
  • Arun Kumaran Anguraj Vadivel, Tim McDowell, Justin B Renaud, Sangeeta Dhaubhadel. A combinatorial action of GmMYB176 and GmbZIP5 controls isoflavonoid biosynthesis in soybean (Glycine max). Communications biology. 2021 03; 4(1):356. doi: 10.1038/s42003-021-01889-6. [PMID: 33742087]
  • Ye Zhang, Kazuhiro Takao, Chizumi Abe, Kuni Sasaki, Koji Ochiai, Toshiro Matsui. Intestinal Absorption of Prenylated Isoflavones, Glyceollins, in Sprague-Dawley Rats. Journal of agricultural and food chemistry. 2020 Aug; 68(31):8205-8211. doi: 10.1021/acs.jafc.0c02475. [PMID: 32648443]
  • Sylvia Kalli, Carla Araya-Cloutier, Yiran Lin, Wouter J C de Bruijn, John Chapman, Jean-Paul Vincken. Enhanced biosynthesis of the natural antimicrobial glyceollins in soybean seedlings by priming and elicitation. Food chemistry. 2020 Jul; 317(?):126389. doi: 10.1016/j.foodchem.2020.126389. [PMID: 32097822]
  • Md Asraful Jahan, Brianna Harris, Matthew Lowery, Aniello M Infante, Ryan J Percifield, Nik Kovinich. Glyceollin Transcription Factor GmMYB29A2 Regulates Soybean Resistance to Phytophthora sojae. Plant physiology. 2020 06; 183(2):530-546. doi: 10.1104/pp.19.01293. [PMID: 32209590]
  • Hyeong-U Son, Eun-Kyeong Yoon, Chi-Yeol Yoo, Chul-Hong Park, Myung-Ae Bae, Tae-Ho Kim, Chang Hyung Lee, Ki Won Lee, Hogyun Seo, Kyung-Jin Kim, Sang-Han Lee. Effects of Synergistic Inhibition on α-glucosidase by Phytoalexins in Soybeans. Biomolecules. 2019 12; 9(12):. doi: 10.3390/biom9120828. [PMID: 31817312]
  • Md Asraful Jahan, Brianna Harris, Matthew Lowery, Katie Coburn, Aniello M Infante, Ryan J Percifield, Amanda G Ammer, Nik Kovinich. The NAC family transcription factor GmNAC42-1 regulates biosynthesis of the anticancer and neuroprotective glyceollins in soybean. BMC genomics. 2019 Feb; 20(1):149. doi: 10.1186/s12864-019-5524-5. [PMID: 30786857]
  • Thu Ha Pham, Sylvain Lecomte, Theo Efstathiou, Francois Ferriere, Farzad Pakdel. An Update on the Effects of Glyceollins on Human Health: Possible Anticancer Effects and Underlying Mechanisms. Nutrients. 2019 Jan; 11(1):. doi: 10.3390/nu11010079. [PMID: 30609801]
  • Livia Deice Raasch-Fernandes, Solange Maria Bonaldo, Domingos de Jesus Rodrigues, Gerardo Magela Vieira-Junior, Kátia Regina Freitas Schwan-Estrada, Camila Rocco da Silva, Ana Gabriela Araújo Verçosa, Daiane Lopes de Oliveira, Bryan Wender Debiasi. Induction of phytoalexins and proteins related to pathogenesis in plants treated with extracts of cutaneous secretions of southern Amazonian Bufonidae amphibians. PloS one. 2019; 14(1):e0211020. doi: 10.1371/journal.pone.0211020. [PMID: 30653617]
  • Md Asraful Jahan, Nik Kovinich. Acidity stress for the systemic elicitation of glyceollin phytoalexins in soybean plants. Plant signaling & behavior. 2019; 14(7):1604018. doi: 10.1080/15592324.2019.1604018. [PMID: 30985226]
  • Arjun Sukumaran, Tim McDowell, Ling Chen, Justin Renaud, Sangeeta Dhaubhadel. Isoflavonoid-specific prenyltransferase gene family in soybean: GmPT01, a pterocarpan 2-dimethylallyltransferase involved in glyceollin biosynthesis. The Plant journal : for cell and molecular biology. 2018 12; 96(5):966-981. doi: 10.1111/tpj.14083. [PMID: 30195273]
  • Hyelin Seo, Jisun Oh, Dongyup Hahn, Chong-Suk Kwon, Jeong Soon Lee, Jong-Sang Kim. Protective Effect of Glyceollins in a Mouse Model of Dextran Sulfate Sodium-Induced Colitis. Journal of medicinal food. 2017 Nov; 20(11):1055-1062. doi: 10.1089/jmf.2017.3960. [PMID: 28956670]
  • Kelli Farrell, Md Asraful Jahan, Nik Kovinich. Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I. Molecules (Basel, Switzerland). 2017 Jul; 22(8):. doi: 10.3390/molecules22081261. [PMID: 28749423]
  • Keisuke Yoneyama, Tomoyoshi Akashi, Toshio Aoki. Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids. Plant & cell physiology. 2016 Dec; 57(12):2497-2509. doi: 10.1093/pcp/pcw178. [PMID: 27986914]
  • Melyssa R Bratton, Elizabeth C Martin, Steven Elliott, Lyndsay V Rhodes, Bridgette M Collins-Burow, John A McLachlan, Thomas E Wiese, Stephen M Boue, Matthew E Burow. Glyceollin, a novel regulator of mTOR/p70S6 in estrogen receptor positive breast cancer. The Journal of steroid biochemistry and molecular biology. 2015 Jun; 150(?):17-23. doi: 10.1016/j.jsbmb.2014.12.014. [PMID: 25771071]
  • Luca Sella, Katia Gazzetti, Carla Castiglioni, Wilhelm Schäfer, Francesco Favaron. Fusarium graminearum Possesses Virulence Factors Common to Fusarium Head Blight of Wheat and Seedling Rot of Soybean but Differing in Their Impact on Disease Severity. Phytopathology. 2014 Nov; 104(11):1201-7. doi: 10.1094/phyto-12-13-0355-r. [PMID: 24779355]
  • Hyo Jung Kim, Chae Lim Jung, Yeon Shin Jeong, Jong-Sang Kim. Soybean-derived glyceollins induce apoptosis through ROS generation. Food & function. 2014 Apr; 5(4):688-95. doi: 10.1039/c3fo60379b. [PMID: 24513878]
  • Chukwuemezie Chimezie, Adina C Ewing, Syeda S Quadri, Richard B Cole, Stephen M Boué, Christopher F Omari, Melyssa Bratton, Elena Glotser, Elena Skripnikova, Ian Townley, Robert E Stratford. Glyceollin transport, metabolism, and effects on p-glycoprotein function in Caco-2 cells. Journal of medicinal food. 2014 Apr; 17(4):462-71. doi: 10.1089/jmf.2013.0115. [PMID: 24476214]
  • Syeda S Quadri, Robert E Stratford, Stephen M Boué, Richard B Cole. Identification of glyceollin metabolites derived from conjugation with glutathione and glucuronic acid in male ZDSD rats by online liquid chromatography-electrospray ionization tandem mass spectrometry. Journal of agricultural and food chemistry. 2014 Mar; 62(12):2692-700. doi: 10.1021/jf403498f. [PMID: 24617284]
  • Jin-Hwa Choi, Minh Phuong Nguyen, Seok-Yun Jung, Sang-Mo Kwon, Jun-Goo Jee, Jong-Sup Bae, Sangkyu Lee, Min Young Lee, You-Mie Lee. Inhibitory effect of glyceollins on vasculogenesis through suppression of endothelial progenitor cell function. Molecular nutrition & food research. 2013 Oct; 57(10):1762-71. doi: 10.1002/mnfr.201200826. [PMID: 23784812]
  • Haiqiu Huang, Zhuohong Xie, Stephen M Boue, Deepak Bhatnagar, Wallace Yokoyama, Liangli Lucy Yu, Thomas T Y Wang. Cholesterol-lowering activity of soy-derived glyceollins in the golden Syrian hamster model. Journal of agricultural and food chemistry. 2013 Jun; 61(24):5772-82. doi: 10.1021/jf400557p. [PMID: 23697397]
  • Eun-Kyung Yoon, Yong-Tae Jeong, Xian Li, Song-Cui, Dong-Chan Park, Yong-Hoon Kim, Yong Deuk Kim, Hyeun Wook Chang, Sang-Han Lee, Seung-Lark Hwang. Glyceollin improves endoplasmic reticulum stress-induced insulin resistance through CaMKK-AMPK pathway in L6 myotubes. The Journal of nutritional biochemistry. 2013 Jun; 24(6):1053-61. doi: 10.1016/j.jnutbio.2012.08.003. [PMID: 23313043]
  • Syeda S Quadri, Robert E Stratford, Stephen M Boué, Richard B Cole. Screening and identification of glyceollins and their metabolites by electrospray ionization tandem mass spectrometry with precursor ion scanning. Analytical chemistry. 2013 Feb; 85(3):1727-33. doi: 10.1021/ac3030398. [PMID: 23294002]
  • Sun H Lee, Jongkook Lee, Myung H Jung, You M Lee. Glyceollins, a novel class of soy phytoalexins, inhibit angiogenesis by blocking the VEGF and bFGF signaling pathways. Molecular nutrition & food research. 2013 Feb; 57(2):225-34. doi: 10.1002/mnfr.201200489. [PMID: 23229497]
  • Stephen M Boué, Iryna A Isakova, Matthew E Burow, Heping Cao, Deepak Bhatnagar, Jeff G Sarver, Kamlesh V Shinde, Paul W Erhardt, Mark L Heiman. Glyceollins, soy isoflavone phytoalexins, improve oral glucose disposal by stimulating glucose uptake. Journal of agricultural and food chemistry. 2012 Jun; 60(25):6376-82. doi: 10.1021/jf301057d. [PMID: 22655912]
  • John E Casida. The greening of pesticide-environment interactions: some personal observations. Environmental health perspectives. 2012 Apr; 120(4):487-93. doi: 10.1289/ehp.1104405. [PMID: 22472325]
  • Eun-Kyung Yoon, Hyun-Kyoung Kim, Song Cui, Yong-Hoon Kim, Sang-Han Lee. Soybean glyceollins mitigate inducible nitric oxide synthase and cyclooxygenase-2 expression levels via suppression of the NF-κB signaling pathway in RAW 264.7 cells. International journal of molecular medicine. 2012 Apr; 29(4):711-7. doi: 10.3892/ijmm.2012.887. [PMID: 22246209]
  • Hee Young Jeon, Dae Bang Seo, Hyun-Jung Shin, Sang-Jun Lee. Effect of Aspergillus oryzae-challenged germination on soybean isoflavone content and antioxidant activity. Journal of agricultural and food chemistry. 2012 Mar; 60(11):2807-14. doi: 10.1021/jf204708n. [PMID: 22409158]
  • Hyo Jung Kim, Ji-Sun Lim, Woo-Keun Kim, Jong-Sang Kim. Soyabean glyceollins: biological effects and relevance to human health. The Proceedings of the Nutrition Society. 2012 Feb; 71(1):166-74. doi: 10.1017/s0029665111003272. [PMID: 22054259]
  • Charles E Wood, Stephen M Boue, Bridgette M Collins-Burow, Lyndsay V Rhodes, Thomas C Register, J Mark Cline, Fitriya N Dewi, Matthew E Burow. Glyceollin-elicited soy protein consumption induces distinct transcriptional effects as compared to standard soy protein. Journal of agricultural and food chemistry. 2012 Jan; 60(1):81-6. doi: 10.1021/jf2034863. [PMID: 22126086]
  • Heung Joo Yuk, Marcus J Curtis-Long, Hyung Won Ryu, Ki Chang Jang, Woo Duck Seo, Jun Young Kim, Kyu Young Kang, Ki Hun Park. Pterocarpan profiles for soybean leaves at different growth stages and investigation of their glycosidase inhibitions. Journal of agricultural and food chemistry. 2011 Dec; 59(23):12683-90. doi: 10.1021/jf203326c. [PMID: 21988571]
  • Sujon Sarowar, Youfu Zhao, Ruth Elena Soria-Guerra, Shahjahan Ali, Danman Zheng, Dongping Wang, Schuyler S Korban. Expression profiles of differentially regulated genes during the early stages of apple flower infection with Erwinia amylovora. Journal of experimental botany. 2011 Oct; 62(14):4851-61. doi: 10.1093/jxb/err147. [PMID: 21725032]
  • Rudy Simons, Jean-Paul Vincken, Nikolaos Roidos, Toine F H Bovee, Martijn van Iersel, Marian A Verbruggen, Harry Gruppen. Increasing soy isoflavonoid content and diversity by simultaneous malting and challenging by a fungus to modulate estrogenicity. Journal of agricultural and food chemistry. 2011 Jun; 59(12):6748-58. doi: 10.1021/jf2010707. [PMID: 21561073]
  • Clifford Louime, Jiang Lu, Oghenekome Onokpise, Hemanth K N Vasanthaiah, Devaiah Kambiranda, Sheikh M Basha, Hae Keun Yun. Resistance to Elsinoë ampelina and expression of related resistant genes in Vitis rotundifolia Michx. grapes. International journal of molecular sciences. 2011; 12(6):3473-88. doi: 10.3390/ijms12063473. [PMID: 21747689]
  • Hyo Jung Kim, Hwa-Jin Suh, Jeong Hwan Kim, Sunmin Park, Young Chul Joo, Jong-Sang Kim. Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae. Journal of agricultural and food chemistry. 2010 Nov; 58(22):11633-8. doi: 10.1021/jf102829z. [PMID: 21033668]
  • Katrien Curvers, Hamed Seifi, Grégory Mouille, Riet de Rycke, Bob Asselbergh, Annelies Van Hecke, Dieter Vanderschaeghe, Herman Höfte, Nico Callewaert, Frank Van Breusegem, Monica Höfte. Abscisic acid deficiency causes changes in cuticle permeability and pectin composition that influence tomato resistance to Botrytis cinerea. Plant physiology. 2010 Oct; 154(2):847-60. doi: 10.1104/pp.110.158972. [PMID: 20709830]
  • Hyo Jung Kim, Hwa-Jin Suh, Choong Hwan Lee, Jeong Hwan Kim, Sun Chul Kang, Sunmin Park, Jong-Sang Kim. Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae. Journal of agricultural and food chemistry. 2010 Sep; 58(17):9483-7. doi: 10.1021/jf101694t. [PMID: 20666365]
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  • Mee Ryung Lee, Joo Yeon Kim, Jiyeon Chun, Sunmin Park, Hyo Jung Kim, Jong-Sang Kim, Jong-Il Jeong, Jeong Hwan Kim. Induction of glyceollins by fungal infection in varieties of Korean soybean. Journal of microbiology and biotechnology. 2010 Aug; 20(8):1226-9. doi: 10.4014/jmb.1005.03047. [PMID: 20798587]
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