Glucoraphanin (BioDeep_00000230230)
Secondary id: BioDeep_00000002610
natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds
代谢物信息卡片
化学式: C12H23NO10S3 (437.0484058)
中文名称: 葡甘氨酸钾盐, 萝卜硫苷
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 30%
分子结构信息
SMILES: CS(=O)CCCCC(=NOS(=O)(=O)O)SC1C(C(C(C(O1)CO)O)O)O
InChI: InChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/b13-8+/t7-,9-,10+,11-,12+,25?/m1/s1
描述信息
A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.
Acquisition and generation of the data is financially supported by the Max-Planck-Society
Glucoraphanin is under investigation in clinical trial NCT01879878 (Pilot Study Evaluating Broccoli Sprouts in Advanced Pancreatic Cancer [POUDER Trial]).
Glucoraphanin is a natural product found in Arabidopsis thaliana, Brassica, and Raphanus sativus with data available.
Glucoraphanin, a natural glucosinolate found in cruciferous vegetable, is a stable precursor of the Nrf2 inducer sulforaphane, which possesses antioxidant, anti-inflammatory, and anti-carcinogenic effects.
Glucoraphanin, a natural glucosinolate found in cruciferous vegetable, is a stable precursor of the Nrf2 inducer sulforaphane, which possesses antioxidant, anti-inflammatory, and anti-carcinogenic effects.
同义名列表
15 个代谢物同义名
Glucoraphanin; 4-Methylsulfinyl-n-butyl glucosinolate; 4-Methylsuphinylbutyl glucosinolate; 4-Methylsulfinylbutyl glucosinolate; 4-(Methylsulfinyl)butylglucosinolate; (((5-(Methylsulfinyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)pentylidene)amino)oxy)sulfonic acid; [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-5-methylsulfinyl-N-sulfooxypentanimidothioate; glucopyranose, 1-thio-, 1-(5-(methylsulfinyl)valerohydroximate) nO-(hydrogen sulfate), beta-D-; beta-D-glucopyranose, 1-thio-, 1-(5-(methylsulfinyl)-N-(sulfooxy)pentanimidate); 4-(methylsulfinyl)butyl glucosinolate; Glucoraphani potassium salt; Sulforaphane glucosinolate; Glucorafanin; RAA; Glucoraphanin
数据库引用编号
46 个数据库交叉引用编号
- ChEBI: CHEBI:79311
- PubChem: 6602383
- PubChem: 9548634
- PubChem: 4479912
- DrugBank: DB15436
- Wikipedia: Glucoraphanin
- MeSH: glucoraphanin
- ChemIDplus: 0021414415
- CAS: 21414-41-5
- CAS: 1432982-77-8
- MoNA: FiehnHILIC002726
- MoNA: FiehnHILIC002725
- MoNA: FiehnHILIC001961
- MoNA: FiehnHILIC001212
- MoNA: PM018121
- MoNA: PM018008
- MoNA: PM015105
- MoNA: PM013801
- MoNA: PM010011
- MoNA: PM010002
- MoNA: PM005802
- MoNA: PT205090
- MoNA: PT110750
- MoNA: CE000366
- MoNA: CE000365
- MoNA: CE000364
- MoNA: CE000363
- MoNA: CE000362
- MoNA: CE000361
- MoNA: CE000360
- MoNA: CE000359
- MoNA: CE000358
- MoNA: CE000357
- MoNA: CE000356
- MoNA: CE000355
- MoNA: CE000354
- MoNA: CE000353
- MoNA: CE000352
- MoNA: CE000351
- MoNA: CE000350
- MoNA: CE000349
- medchemexpress: HY-N4068
- MetaboLights: MTBLC79311
- KEGG: C08419
- PubChem: 10615
- KNApSAcK: 79311
分类词条
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)
13 个相关的物种来源信息
- 3702 - Arabidopsis thaliana: 10.1104/PP.109.148031
- 3702 - Arabidopsis thaliana: 10.3390/IJMS17091565
- 1282088 - Arabis allionii: 10.1002/JLAC.19123920102
- 3705 - Brassica: 10.1016/S0031-9422(00)81740-9
- 3712 - Brassica oleracea:
- 3715 - Brassica oleracea var. botrytis:
- 3716 - Brassica oleracea var. capitata:
- 178616 - Brassica oleracea var. gemmifera:
- 36774 - Brassica oleracea var. italica:
- 3711 - Brassica rapa: 10.1016/J.PHYTOCHEM.2007.08.014
- 374105 - Erysimum perofskianum: 10.1002/JLAC.19123920102
- 33090 - Plants: -
- 33090 - 西兰花: -
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
- Hao Zheng, Wenli Huang, Xiangxiang Li, Huanhuan Huang, Qiao Yuan, Ruobin Liu, Hongmei Di, Sha Liang, Mengyu Wang, Mengyao Li, Zhi Huang, Yi Tang, Yangxia Zheng, Huiying Miao, Jie Ma, Huanxiu Li, Qiaomei Wang, Bo Sun, Fen Zhang. CRISPR/Cas9-mediated BoaAOP2s editing alters aliphatic glucosinolate side-chain metabolic flux and increases the glucoraphanin content in Chinese kale.
Food research international (Ottawa, Ont.).
2023 08; 170(?):112995. doi:
10.1016/j.foodres.2023.112995
. [PMID: 37316021] - Jiaying Wu, Weiling Guo, Shumao Cui, Xin Tang, Qiuxiang Zhang, Wenwei Lu, Yan Jin, Jianxin Zhao, Bingyong Mao, Wei Chen. Broccoli seed extract rich in polysaccharides and glucoraphanin ameliorates DSS-induced colitis via intestinal barrier protection and gut microbiota modulation in mice.
Journal of the science of food and agriculture.
2023 Mar; 103(4):1749-1760. doi:
10.1002/jsfa.12382
. [PMID: 36495024] - Qingxi Yang, Manli Luo, Qian Zhou, Yingbo Zhao, Jianye Chen, Shujuan Ji. Insights into the loss of glucoraphanin in post-harvested broccoli--Possible involvement of the declined supply capacity of sulfur donor.
Plant science : an international journal of experimental plant biology.
2023 Mar; 328(?):111580. doi:
10.1016/j.plantsci.2022.111580
. [PMID: 36587585] - Jinyu Bao, Xu Lu, Lei Ma, Xiumin Zhang, Peng Tian, Xiaoling Zhang, Sheng Li, Shaoying Ma, Jie Yang, Yaqi Lu, Yunchun Wei, Congcong Zhang, Xiaotong Shi. Transcriptome analysis of genes related to glucoraphanin and sulforaphane synthesis in methyl jasmonate treated broccoli (Brassica oleracea var. italica) hairy roots.
Journal of plant research.
2022 Nov; 135(6):757-770. doi:
10.1007/s10265-022-01407-7
. [PMID: 35999478] - Shaoying Ma, Jinyu Bao, Yaqi Lu, Xu Lu, Peng Tian, Xiaoling Zhang, Jie Yang, Xiaotong Shi, Zhihui Pu, Sheng Li. Glucoraphanin and sulforaphane biosynthesis by melatonin mediating nitric oxide in hairy roots of broccoli (Brassica oleracea L. var. italica Planch): insights from transcriptome data.
BMC plant biology.
2022 Aug; 22(1):403. doi:
10.1186/s12870-022-03747-x
. [PMID: 35974315] - Collin R Barnum, Benjamin J Endelman, Izaiah J Ornelas, Roxanna M Pignolet, Patrick M Shih. Optimization of Heterologous Glucoraphanin Production In Planta.
ACS synthetic biology.
2022 05; 11(5):1865-1873. doi:
10.1021/acssynbio.2c00030
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The Journal of nutritional biochemistry.
2022 02; 100(?):108885. doi:
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International journal of molecular sciences.
2021 Jul; 22(14):. doi:
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Molecules (Basel, Switzerland).
2021 Jul; 26(13):. doi:
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Food chemistry.
2021 May; 345(?):128771. doi:
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European journal of nutrition.
2021 Apr; 60(3):1263-1276. doi:
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European archives of psychiatry and clinical neuroscience.
2021 Mar; 271(2):387-389. doi:
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. [PMID: 32488522] - Li Zhuang, Kexin Xu, Yinglian Zhu, Fengwu Wang, Junxia Xiao, Liping Guo. Calcium affects glucoraphanin metabolism in broccoli sprouts under ZnSO4 stress.
Food chemistry.
2021 Jan; 334(?):127520. doi:
10.1016/j.foodchem.2020.127520
. [PMID: 32693332] - Mohammed S Almuhayawi, Hamada AbdElgawad, Soad K Al Jaouni, Samy Selim, Abdelrahim H A Hassan, Galal Khamis. Elevated CO2 improves glucosinolate metabolism and stimulates anticancer and anti-inflammatory properties of broccoli sprouts.
Food chemistry.
2020 Oct; 328(?):127102. doi:
10.1016/j.foodchem.2020.127102
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Microbiological research.
2020 Sep; 238(?):126484. doi:
10.1016/j.micres.2020.126484
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Food chemistry.
2020 Jul; 319(?):126498. doi:
10.1016/j.foodchem.2020.126498
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Food research international (Ottawa, Ont.).
2020 06; 132(?):109055. doi:
10.1016/j.foodres.2020.109055
. [PMID: 32331656] - Jianghao Sun, Craig S Charron, Janet A Novotny, Bing Peng, Liangli Yu, Pei Chen. Profiling glucosinolate metabolites in human urine and plasma after broccoli consumption using non-targeted and targeted metabolomic analyses.
Food chemistry.
2020 Mar; 309(?):125660. doi:
10.1016/j.foodchem.2019.125660
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Journal of the science of food and agriculture.
2020 Mar; 100(5):2099-2109. doi:
10.1002/jsfa.10233
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Food chemistry.
2020 Mar; 307(?):125562. doi:
10.1016/j.foodchem.2019.125562
. [PMID: 31648174] - Adji Baskoro Dwi Nugroho, Narae Han, Aditya Nurmalita Pervitasari, Dong-Hwan Kim, Jongkee Kim. Differential expression of major genes involved in the biosynthesis of aliphatic glucosinolates in intergeneric Baemoochae (Brassicaceae) and its parents during development.
Plant molecular biology.
2020 Jan; 102(1-2):171-184. doi:
10.1007/s11103-019-00939-2
. [PMID: 31792713] - Liang Xu, Naoto Nagata, Tsuguhito Ota. Impact of Glucoraphanin-Mediated Activation of Nrf2 on Non-Alcoholic Fatty Liver Disease with a Focus on Mitochondrial Dysfunction.
International journal of molecular sciences.
2019 Nov; 20(23):. doi:
10.3390/ijms20235920
. [PMID: 31775341] - Jack Coode-Bate, Tharsini Sivapalan, Antonietta Melchini, Shikha Saha, Paul W Needs, Jack R Dainty, Jean-Bapiste Maicha, Gemma Beasy, Maria H Traka, Robert D Mills, Richard Y Ball, Richard F Mithen. Accumulation of Dietary S-Methyl Cysteine Sulfoxide in Human Prostate Tissue.
Molecular nutrition & food research.
2019 10; 63(20):e1900461. doi:
10.1002/mnfr.201900461
. [PMID: 31410992] - Supatta Chawalitpong, Saki Ichikawa, Yuki Uchibori, Soichiro Nakamura, Shigeru Katayama. Long-Term Intake of Glucoraphanin-Enriched Kale Suppresses Skin Aging via Activating Nrf2 and the TβRII/Smad Pathway in SAMP1 Mice.
Journal of agricultural and food chemistry.
2019 Sep; 67(35):9782-9788. doi:
10.1021/acs.jafc.9b02725
. [PMID: 31390859] - Yaoyu Pu, Youge Qu, Lijia Chang, Si-Ming Wang, Kai Zhang, Yusuke Ushida, Hiroyuki Suganuma, Kenji Hashimoto. Dietary intake of glucoraphanin prevents the reduction of dopamine transporter in the mouse striatum after repeated administration of MPTP.
Neuropsychopharmacology reports.
2019 09; 39(3):247-251. doi:
10.1002/npr2.12060
. [PMID: 31132231] - Diana L Zuluaga, Neil S Graham, Annett Klinder, A E Elaine van Ommen Kloeke, Angelo R Marcotrigiano, Carol Wagstaff, Ruud Verkerk, Gabriella Sonnante, Mark G M Aarts. Overexpression of the MYB29 transcription factor affects aliphatic glucosinolate synthesis in Brassica oleracea.
Plant molecular biology.
2019 Sep; 101(1-2):65-79. doi:
10.1007/s11103-019-00890-2
. [PMID: 31190320] - Jed W Fahey, Kristina L Wade, Katherine K Stephenson, Anita A Panjwani, Hua Liu, Grace Cornblatt, Brian S Cornblatt, Stacy L Ownby, Edward Fuchs, Walter David Holtzclaw, Lawrence J Cheskin. Bioavailability of Sulforaphane Following Ingestion of Glucoraphanin-Rich Broccoli Sprout and Seed Extracts with Active Myrosinase: A Pilot Study of the Effects of Proton Pump Inhibitor Administration.
Nutrients.
2019 Jun; 11(7):. doi:
10.3390/nu11071489
. [PMID: 31261930] - Alena Vanduchova, Pavel Anzenbacher, Eva Anzenbacherova. Isothiocyanate from Broccoli, Sulforaphane, and Its Properties.
Journal of medicinal food.
2019 Feb; 22(2):121-126. doi:
10.1089/jmf.2018.0024
. [PMID: 30372361] - Ginés B Martínez-Hernández, Tâmmila Venzke-Klug, María Del Mar Carrión-Monteagudo, Francisco Artés Calero, José M López-Nicolás, Francisco Artés-Hernández. Effects of α-, β- and maltosyl-β-cyclodextrins use on the glucoraphanin-sulforaphane system of broccoli juice.
Journal of the science of food and agriculture.
2019 Jan; 99(2):941-946. doi:
10.1002/jsfa.9269
. [PMID: 30009400] - Zhansheng Li, Yumei Liu, Lingyun Li, Zhiyuan Fang, Limei Yang, Mu Zhuang, Yangyong Zhang, Honghao Lv. Transcriptome reveals the gene expression patterns of sulforaphane metabolism in broccoli florets.
PloS one.
2019; 14(3):e0213902. doi:
10.1371/journal.pone.0213902
. [PMID: 30908527] - Craig S Charron, Bryan T Vinyard, Sharon A Ross, Harold E Seifried, Elizabeth H Jeffery, Janet A Novotny. Absorption and metabolism of isothiocyanates formed from broccoli glucosinolates: effects of BMI and daily consumption in a randomised clinical trial.
The British journal of nutrition.
2018 12; 120(12):1370-1379. doi:
10.1017/s0007114518002921
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Molecular nutrition & food research.
2018 09; 62(18):e1700837. doi:
10.1002/mnfr.201700837
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Molecular nutrition & food research.
2018 09; 62(18):e1700980. doi:
10.1002/mnfr.201700980
. [PMID: 29806738] - Tharsini Sivapalan, Antonietta Melchini, Shikha Saha, Paul W Needs, Maria H Traka, Henri Tapp, Jack R Dainty, Richard F Mithen. Bioavailability of Glucoraphanin and Sulforaphane from High-Glucoraphanin Broccoli.
Molecular nutrition & food research.
2018 09; 62(18):e1700911. doi:
10.1002/mnfr.201700911
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Natural product research.
2018 Jul; 32(14):1617-1626. doi:
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Journal of the science of food and agriculture.
2018 Mar; 98(5):1863-1872. doi:
10.1002/jsfa.8665
. [PMID: 28885683] - Han Yang, Feixia Liu, Yin Li, Bo Yu. Reconstructing Biosynthetic Pathway of the Plant-Derived Cancer Chemopreventive-Precursor Glucoraphanin in Escherichia coli.
ACS synthetic biology.
2018 01; 7(1):121-131. doi:
10.1021/acssynbio.7b00256
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World journal of gastroenterology.
2017 Jun; 23(23):4146-4157. doi:
10.3748/wjg.v23.i23.4146
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Molecules (Basel, Switzerland).
2017 May; 22(5):. doi:
10.3390/molecules22050851
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Diabetes.
2017 05; 66(5):1222-1236. doi:
10.2337/db16-0662
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Molecular nutrition & food research.
2017 04; 61(4):. doi:
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The Journal of nutritional biochemistry.
2017 01; 39(?):134-144. doi:
10.1016/j.jnutbio.2016.10.004
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Scientific reports.
2016 07; 6(?):30659. doi:
10.1038/srep30659
. [PMID: 27470577] - Maria Del Carmen Martínez-Ballesta, Horacio Pérez-Sánchez, Diego A Moreno, Micaela Carvajal. Plant plasma membrane aquaporins in natural vesicles as potential stabilizers and carriers of glucosinolates.
Colloids and surfaces. B, Biointerfaces.
2016 Jul; 143(?):318-326. doi:
10.1016/j.colsurfb.2016.03.056
. [PMID: 27022872] - Arif Hasan Khan Robin, Go-Eun Yi, Rawnak Laila, Kiwoung Yang, Jong-In Park, Hye Ran Kim, Ill-Sup Nou. Expression Profiling of Glucosinolate Biosynthetic Genes in Brassica oleracea L. var. capitata Inbred Lines Reveals Their Association with Glucosinolate Content.
Molecules (Basel, Switzerland).
2016 Jun; 21(6):. doi:
10.3390/molecules21060787
. [PMID: 27322230] - Nadia Mirza, Christoph Crocoll, Carl Erik Olsen, Barbara Ann Halkier. Engineering of methionine chain elongation part of glucoraphanin pathway in E. coli.
Metabolic engineering.
2016 May; 35(?):31-37. doi:
10.1016/j.ymben.2015.09.012
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Nutrition reviews.
2016 Apr; 74(4):248-58. doi:
10.1093/nutrit/nuv110
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Scientific reports.
2015 Dec; 5(?):18005. doi:
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. [PMID: 26657321] - Ling Yin, Changming Chen, Guoju Chen, Bihao Cao, Jianjun Lei. Molecular Cloning, Expression Pattern and Genotypic Effects on Glucoraphanin Biosynthetic Related Genes in Chinese Kale (Brassica oleracea var. alboglabra Bailey).
Molecules (Basel, Switzerland).
2015 Nov; 20(11):20254-67. doi:
10.3390/molecules201119688
. [PMID: 26569208] - Ingrid Aguiló-Aguayo, Manuel Suarez, Lucia Plaza, Mohammad B Hossain, Nigel Brunton, James G Lyng, Dilip K Rai. Optimization of pulsed electric field pre-treatments to enhance health-promoting glucosinolates in broccoli flowers and stalk.
Journal of the science of food and agriculture.
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