Sinigrin (BioDeep_00000003569)

 

Secondary id: BioDeep_00001870522

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonic acid

化学式: C10H17NO9S2 (359.03447120000004)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.45%

分子结构信息

SMILES: C=CC/C(=N\OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
InChI: InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/t5-,7-,8+,9-,10+/m1/s1

描述信息

Sinigrin is found in brassicas. Sinigrin is isolated from seeds of black mustard (Brassica nigra) and cabbage, as K salt. Sinigrin is present in many crucifers, major glucosinolate in Brussels sprouts (Brassica oleraceae).
Sinigrin is isolated from seeds of black mustard (Brassica nigra) and cabbage, as a K salt. It is found in many crucifers, major glucosinolate in Brussels sprouts (Brassica oleraceae).
Acquisition and generation of the data is financially supported in part by CREST/JST.

同义名列表

15 个代谢物同义名

{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonic acid; {[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid; {[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonate; [(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid; {[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonate; [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] N-sulfooxybut-3-enimidothioate; 1-thio-b-D-Glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ci; sinigrin, monopotassium salt; 2-Phenylethyl glucosinolate; 2-Propenyl glucosinolate; 2-Propenyl (sinigrin); Allyl glucosinolate; Myronic acid; myronate; Sinigrin



数据库引用编号

28 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

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)

73 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

  • Azra Đulović, Franko Burčul, Vedrana Čikeš Čulić, Patrick Rollin, Ivica Blažević. Glucosinolates and Cytotoxic Activity of Collard Volatiles Obtained Using Microwave-Assisted Extraction. Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041657. [PMID: 36838645]
  • Laura Plaza-Vinuesa, Oswaldo Hernandez-Hernandez, Ana Sánchez-Arroyo, José M Cumella, Nieves Corzo, Ana M Muñoz-Labrador, F Javier Moreno, Blanca de Las Rivas, Rosario Muñoz. Deciphering the Myrosinase-like Activity of Lactiplantibacillus plantarum WCFS1 among GH1 Family Glycoside Hydrolases. Journal of agricultural and food chemistry. 2022 Dec; 70(49):15531-15538. doi: 10.1021/acs.jafc.2c06240. [PMID: 36454042]
  • Yan Chen, Pei-Chao Wang, Shuai-Shuai Zhang, Jun Yang, Guo-Cheng Li, Ling-Qiao Huang, Chen-Zhu Wang. Functional analysis of a bitter gustatory receptor highly expressed in the larval maxillary galea of Helicoverpa armigera. PLoS genetics. 2022 10; 18(10):e1010455. doi: 10.1371/journal.pgen.1010455. [PMID: 36206313]
  • Shuqin Li, Jiawen Lin, Jiaofei Wei, Lingzhi Zhou, Peishun Wang. Sinigrin Impedes the Breast Cancer Cell Growth through the Inhibition of PI3K/AKT/mTOR Phosphorylation-Mediated Cell Cycle Arrest. Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer. 2022; 41(3):33-43. doi: 10.1615/jenvironpatholtoxicoloncol.2022041136. [PMID: 35993954]
  • Neha Sylvia Walter, Varun Gorki, Monika Chauhan, Neelima Dhingra, Sukhbir Kaur. Sinigrin in combination with artesunate provides protection against lethal murine malaria via falcipain-3 inhibition and immune modulation. International immunopharmacology. 2021 Dec; 101(Pt A):108320. doi: 10.1016/j.intimp.2021.108320. [PMID: 34741871]
  • Cong Cong, Xiaohong Yuan, Ying Hu, Wenjing Chen, Yong Wang, Lei Tao. Sinigrin attenuates angiotensin II‑induced kidney injury by inactivating nuclear factor‑κB and extracellular signal‑regulated kinase signaling in vivo and in vitro. International journal of molecular medicine. 2021 Aug; 48(2):. doi: 10.3892/ijmm.2021.4994. [PMID: 34278443]
  • Jun Yang, Hao Guo, Nan-Ji Jiang, Rui Tang, Guo-Cheng Li, Ling-Qiao Huang, Joop J A van Loon, Chen-Zhu Wang. Identification of a gustatory receptor tuned to sinigrin in the cabbage butterfly Pieris rapae. PLoS genetics. 2021 07; 17(7):e1009527. doi: 10.1371/journal.pgen.1009527. [PMID: 34264948]
  • Hee-Yeon Kwon, Sun-Il Choi, Xionggao Han, Xiao Men, Gill-Woong Jang, Ye-Eun Choi, Ok-Hwan Lee. Antiobesity effect of Brassica juncea cultivated in Jeongseon with optimized sinigrin content using 3T3-L1 adipocytes. Journal of food biochemistry. 2021 04; 45(4):e13650. doi: 10.1111/jfbc.13650. [PMID: 33576517]
  • Jinghua Yang, Zhangping Li, Jinmin Lian, Guoning Qi, Pibiao Shi, Jiawei He, Zhongyuan Hu, Mingfang Zhang. Brassicaceae transcriptomes reveal convergent evolution of super-accumulation of sinigrin. Communications biology. 2020 12; 3(1):779. doi: 10.1038/s42003-020-01523-x. [PMID: 33328568]
  • Jie Hu, Jin-Jian Yang, Bai-Ming Liu, Hong-Ying Cui, You-Jun Zhang, Xiao-Guo Jiao. Feeding behavior explains the different effects of cabbage on MEAM1 and MED cryptic species of Bemisia tabaci. Insect science. 2020 Dec; 27(6):1276-1284. doi: 10.1111/1744-7917.12739. [PMID: 31769205]
  • Jilan Nazeam, Esraa Z Mohammed, Mariam Raafat, Mariam Houssein, Asmaa Elkafoury, Dina Hamdy, Lina Jamil. Based on Principles and Insights of COVID-19 Epidemiology, Genome Sequencing, and Pathogenesis: Retrospective Analysis of Sinigrin and ProlixinRX (Fluphenazine) Provides Off-Label Drug Candidates. SLAS discovery : advancing life sciences R & D. 2020 12; 25(10):1123-1140. doi: 10.1177/2472555220950236. [PMID: 32804597]
  • Anroop B Nair, Dipal Gandhi, Snehal S Patel, Mohamed A Morsy, Bapi Gorain, Mahesh Attimarad, Jigar N Shah. Development of HPLC Method for Quantification of Sinigrin from Raphanus sativus Roots and Evaluation of Its Anticancer Potential. Molecules (Basel, Switzerland). 2020 Oct; 25(21):. doi: 10.3390/molecules25214947. [PMID: 33114598]
  • Maria Fernanda Lopez-Rodriguez, Nadia Cymbaluk, Tasha Epp, Bernard Laarveld, Elena Carolina Serrano Recalde, Elemir Simko, Claire Card. Effects of the Glucosinolate Sinigrin in Combination With a Noniodine Supplemented Diet on Serum Iodine and Thyroid Hormone Concentrations in Nonpregnant Mares. Journal of equine veterinary science. 2020 08; 91(?):103110. doi: 10.1016/j.jevs.2020.103110. [PMID: 32684255]
  • Leanne E Mocniak, Kyle Elkin, J Martin Bollinger. Lifetimes of the Aglycone Substrates of Specifier Proteins, the Autonomous Iron Enzymes That Dictate the Products of the Glucosinolate-Myrosinase Defense System in Brassica Plants. Biochemistry. 2020 07; 59(26):2432-2441. doi: 10.1021/acs.biochem.0c00358. [PMID: 32516526]
  • Nur Alim Bahmid, Laurens Pepping, Matthijs Dekker, Vincenzo Fogliano, Jenneke Heising. Using particle size and fat content to control the release of Allyl isothiocyanate from ground mustard seeds for its application in antimicrobial packaging. Food chemistry. 2020 Mar; 308(?):125573. doi: 10.1016/j.foodchem.2019.125573. [PMID: 31639598]
  • 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]
  • Ji H Lee, Jeongyeo Lee, HyeRan Kim, Won B Chae, Sun-Ju Kim, Yong P Lim, Man-Ho Oh. Brassinosteroids regulate glucosinolate biosynthesis in Arabidopsis thaliana. Physiologia plantarum. 2018 Aug; 163(4):450-458. doi: 10.1111/ppl.12691. [PMID: 29315590]
  • Hee-Weon Lee, Dong-Kwon Rhee, Byung-Oh Kim, Suhkneung Pyo. Inhibitory effect of sinigrin on adipocyte differentiation in 3T3-L1 cells: Involvement of AMPK and MAPK pathways. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jun; 102(?):670-680. doi: 10.1016/j.biopha.2018.03.124. [PMID: 29604586]
  • Fangfang Huang, Richard Lankau, Shaolin Peng. Coexistence via coevolution driven by reduced allelochemical effects and increased tolerance to competition between invasive and native plants. The New phytologist. 2018 04; 218(1):357-369. doi: 10.1111/nph.14937. [PMID: 29205373]
  • Aniruddha R Agnihotri, Chaitanya V Hulagabali, Anmol S Adhav, Rakesh S Joshi. Mechanistic insight in potential dual role of sinigrin against Helicoverpa armigera. Phytochemistry. 2018 Jan; 145(?):121-127. doi: 10.1016/j.phytochem.2017.10.014. [PMID: 29126020]
  • Yeon Jeong Jang, Bongkyun Park, Hee-Weon Lee, Hye Jin Park, Hyun Jung Koo, Byung Oh Kim, Eun-Hwa Sohn, Sung Hee Um, Suhkneung Pyo. Sinigrin attenuates the progression of atherosclerosis in ApoE-/- mice fed a high-cholesterol diet potentially by inhibiting VCAM-1 expression. Chemico-biological interactions. 2017 Jun; 272(?):28-36. doi: 10.1016/j.cbi.2017.05.006. [PMID: 28483571]
  • Felix Hirschmann, Florian Krause, Petra Baruch, Igor Chizhov, Jonathan Wolf Mueller, Dietmar J Manstein, Jutta Papenbrock, Roman Fedorov. Structural and biochemical studies of sulphotransferase 18 from Arabidopsis thaliana explain its substrate specificity and reaction mechanism. Scientific reports. 2017 06; 7(1):4160. doi: 10.1038/s41598-017-04539-2. [PMID: 28646214]
  • Alessandra Ferramosca, Mariangela Di Giacomo, Vincenzo Zara. Antioxidant dietary approach in treatment of fatty liver: New insights and updates. World journal of gastroenterology. 2017 Jun; 23(23):4146-4157. doi: 10.3748/wjg.v23.i23.4146. [PMID: 28694655]
  • Sabine Montaut, Benjamin S Guido, Claude Grison, Patrick Rollin. Identification of Glucosinolates in Seeds of Three Brassicaceae Species Known to Hyperaccumulate Heavy Metals. Chemistry & biodiversity. 2017 Mar; 14(3):. doi: 10.1002/cbdv.201600311. [PMID: 27981800]
  • Saurabh Awasthi, N T Saraswathi. Elucidating the molecular interaction of sinigrin, a potent anticancer glucosinolate from cruciferous vegetables with bovine serum albumin: effect of methylglyoxal modification. Journal of biomolecular structure & dynamics. 2016 Oct; 34(10):2224-32. doi: 10.1080/07391102.2015.1110835. [PMID: 26488200]
  • Tarandeep Kaur, Rohini Bhat, Manu Khajuria, Ruchika Vyas, Anika Kumari, Gireesh Nadda, Ram Vishwakarma, Dhiraj Vyas. Dynamics of glucosinolate-myrosinase system during Plutella xylostella interaction to a novel host Lepidium latifolium L. Plant science : an international journal of experimental plant biology. 2016 Sep; 250(?):1-9. doi: 10.1016/j.plantsci.2016.05.012. [PMID: 27457978]
  • 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]
  • Sándor Gonda, Attila Kiss-Szikszai, Zsolt Szűcs, Nhat Minh Nguyen, Gábor Vasas. Myrosinase Compatible Simultaneous Determination of Glucosinolates and Allyl Isothiocyanate by Capillary Electrophoresis Micellar Electrokinetic Chromatography (CE-MEKC). Phytochemical analysis : PCA. 2016 May; 27(3-4):191-8. doi: 10.1002/pca.2615. [PMID: 27313156]
  • X G Wang, X W Gao, P Liang, X Y Shi, D L Song. Induction of Cytochrome P450 Activity by the Interaction of Chlorantraniliprole and Sinigrin in the Spodoptera exigua (Lepidoptera: Noctuidae). Environmental entomology. 2016 Apr; 45(2):500-7. doi: 10.1093/ee/nvw007. [PMID: 26916517]
  • Saurabh Awasthi, N T Saraswathi. Sinigrin, a major glucosinolate from cruciferous vegetables restrains non-enzymatic glycation of albumin. International journal of biological macromolecules. 2016 Feb; 83(?):410-5. doi: 10.1016/j.ijbiomac.2015.11.019. [PMID: 26571343]
  • Manisha Sharma, Arundhati Mukhopadhyay, Vibha Gupta, Deepak Pental, Akshay K Pradhan. BjuB.CYP79F1 Regulates Synthesis of Propyl Fraction of Aliphatic Glucosinolates in Oilseed Mustard Brassica juncea: Functional Validation through Genetic and Transgenic Approaches. PloS one. 2016; 11(2):e0150060. doi: 10.1371/journal.pone.0150060. [PMID: 26919200]
  • Nicole A Goodey, Hannah V Florance, Nicholas Smirnoff, Dave J Hodgson. Aphids Pick Their Poison: Selective Sequestration of Plant Chemicals Affects Host Plant Use in a Specialist Herbivore. Journal of chemical ecology. 2015 Oct; 41(10):956-64. doi: 10.1007/s10886-015-0634-2. [PMID: 26411571]
  • Samantha L Davis, Tina Frisch, Nanna Bjarnholt, Don Cipollini. How Does Garlic Mustard Lure and Kill the West Virginia White Butterfly?. Journal of chemical ecology. 2015 Oct; 41(10):948-55. doi: 10.1007/s10886-015-0633-3. [PMID: 26399433]
  • Krista M Lessner, M Denise Dearing, Ido Izhaki, Michal Samuni-Blank, Zeev Arad, William H Karasov. Small intestinal hydrolysis of plant glucosides: higher glucohydrolase activities in rodents than passerine birds. The Journal of experimental biology. 2015 Sep; 218(Pt 17):2666-9. doi: 10.1242/jeb.121970. [PMID: 26113142]
  • María-Dolores Lozano-Baena, Inmaculada Tasset, Sara Obregón-Cano, Antonio de Haro-Bailon, Andrés Muñoz-Serrano, Ángeles Alonso-Moraga. Antigenotoxicity and Tumor Growing Inhibition by Leafy Brassica carinata and Sinigrin. Molecules (Basel, Switzerland). 2015 Aug; 20(9):15748-65. doi: 10.3390/molecules200915748. [PMID: 26343628]
  • Roniele P Cordeiro, Juan H Doria, George G Zhanel, Richard Sparling, Richard A Holley. Role of glycoside hydrolase genes in sinigrin degradation by E. coli O157:H7. International journal of food microbiology. 2015 Jul; 205(?):105-11. doi: 10.1016/j.ijfoodmicro.2015.04.008. [PMID: 25897994]
  • Anika E Wagner, Christine Sturm, Stefanie Piegholdt, Insa M A Wolf, Tuba Esatbeyoglu, Gina Rosalinda De Nicola, Renato Iori, Gerald Rimbach. Myrosinase-treated glucoerucin is a potent inducer of the Nrf2 target gene heme oxygenase 1--studies in cultured HT-29 cells and mice. The Journal of nutritional biochemistry. 2015 Jun; 26(6):661-6. doi: 10.1016/j.jnutbio.2015.01.004. [PMID: 25776458]
  • Bruno M Ngala, Patrick P J Haydock, Simon Woods, Matthew A Back. Biofumigation with Brassica juncea, Raphanus sativus and Eruca sativa for the management of field populations of the potato cyst nematode Globodera pallida. Pest management science. 2015 May; 71(5):759-69. doi: 10.1002/ps.3849. [PMID: 24965697]
  • Amin N Olaimat, Babak Sobhi, Richard A Holley. Influence of temperature, glucose, and iron on sinigrin degradation by Salmonella and Listeria monocytogenes. Journal of food protection. 2014 Dec; 77(12):2133-8. doi: 10.4315/0362-028x.jfp-14-210. [PMID: 25474062]
  • Inna E Popova, Matthew J Morra. Simultaneous quantification of sinigrin, sinalbin, and anionic glucosinolate hydrolysis products in Brassica juncea and Sinapis alba seed extracts using ion chromatography. Journal of agricultural and food chemistry. 2014 Nov; 62(44):10687-93. doi: 10.1021/jf503755m. [PMID: 25314611]
  • Tina Frisch, Niels Agerbirk, Samantha Davis, Don Cipollini, Carl Erik Olsen, Mohammed Saddik Motawia, Nanna Bjarnholt, Birger Lindberg Møller. Glucosinolate-related glucosides in Alliaria petiolata: sources of variation in the plant and different metabolism in an adapted specialist herbivore, Pieris rapae. Journal of chemical ecology. 2014 Oct; 40(10):1063-79. doi: 10.1007/s10886-014-0509-y. [PMID: 25308480]
  • Rosa Agneta, Filomena Lelario, Susanna De Maria, Christian Möllers, Sabino Aurelio Bufo, Anna Rita Rivelli. Glucosinolate profile and distribution among plant tissues and phenological stages of field-grown horseradish. Phytochemistry. 2014 Oct; 106(?):178-187. doi: 10.1016/j.phytochem.2014.06.019. [PMID: 25060759]
  • Amin N Olaimat, Richard A Holley. Inhibition of Listeria monocytogenes and Salmonella by combinations of oriental mustard, malic acid, and EDTA. Journal of food science. 2014 Apr; 79(4):M614-21. doi: 10.1111/1750-3841.12411. [PMID: 24649979]
  • Serena Santolamazza-Carbone, Pablo Velasco, Pilar Soengas, María Elena Cartea. Bottom-up and top-down herbivore regulation mediated by glucosinolates in Brassica oleracea var. acephala. Oecologia. 2014 Mar; 174(3):893-907. doi: 10.1007/s00442-013-2817-2. [PMID: 24352843]
  • Maria del Carmen Martínez-Ballesta, Beatriz Muries, Diego Ángel Moreno, Raúl Dominguez-Perles, Cristina García-Viguera, Micaela Carvajal. Involvement of a glucosinolate (sinigrin) in the regulation of water transport in Brassica oleracea grown under salt stress. Physiologia plantarum. 2014 Feb; 150(2):145-60. doi: 10.1111/ppl.12082. [PMID: 23837634]
  • Simona I Vicas, Alin C Teusdea, Mihai Carbunar, Sonia A Socaci, Carmen Socaciu. Glucosinolates profile and antioxidant capacity of Romanian Brassica vegetables obtained by organic and conventional agricultural practices. Plant foods for human nutrition (Dordrecht, Netherlands). 2013 Sep; 68(3):313-21. doi: 10.1007/s11130-013-0367-8. [PMID: 23817957]
  • Gaetan Glauser, Fabian Schweizer, Ted C J Turlings, Philippe Reymond. Rapid profiling of intact glucosinolates in Arabidopsis leaves by UHPLC-QTOFMS using a charged surface hybrid column. Phytochemical analysis : PCA. 2012 Sep; 23(5):520-8. doi: 10.1002/pca.2350. [PMID: 22323091]
  • Rosa Agneta, Anna Rita Rivelli, Emanuela Ventrella, Filomena Lelario, Giulio Sarli, Sabino Aurelio Bufo. Investigation of glucosinolate profile and qualitative aspects in sprouts and roots of horseradish (Armoracia rusticana) using LC-ESI-hybrid linear ion trap with Fourier transform ion cyclotron resonance mass spectrometry and infrared multiphoton dissociation. Journal of agricultural and food chemistry. 2012 Aug; 60(30):7474-82. doi: 10.1021/jf301294h. [PMID: 22779710]
  • Katherine Cools, Leon A Terry. Comparative study between extraction techniques and column separation for the quantification of sinigrin and total isothiocyanates in mustard seed. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jul; 901(?):115-8. doi: 10.1016/j.jchromb.2012.05.027. [PMID: 22743340]
  • Richard A Lankau. Coevolution between invasive and native plants driven by chemical competition and soil biota. Proceedings of the National Academy of Sciences of the United States of America. 2012 Jul; 109(28):11240-5. doi: 10.1073/pnas.1201343109. [PMID: 22733785]
  • Marta Lara-Lledó, Amin Olaimat, Richard A Holley. Inhibition of Listeria monocytogenes on bologna sausages by an antimicrobial film containing mustard extract or sinigrin. International journal of food microbiology. 2012 May; 156(1):25-31. doi: 10.1016/j.ijfoodmicro.2012.02.018. [PMID: 22424932]
  • S Herzallah, M Lara Lledó, R Holley. Influence of NaCl and NaNO3 on sinigrin hydrolysis by foodborne bacteria. Journal of food protection. 2011 Dec; 74(12):2162-8. doi: 10.4315/0362-028x.jfp-11-284. [PMID: 22186059]
  • Ayub M O Oduor, Richard A Lankau, Sharon Y Strauss, José M Gómez. Introduced Brassica nigra populations exhibit greater growth and herbivore resistance but less tolerance than native populations in the native range. The New phytologist. 2011 Jul; 191(2):536-544. doi: 10.1111/j.1469-8137.2011.03685.x. [PMID: 21410474]
  • Tianxin Wang, Hao Liang, Qipeng Yuan. Optimization of ultrasonic-stimulated solvent extraction of sinigrin from Indian mustard seed (Brassica Juncea L.) using response surface methodology. Phytochemical analysis : PCA. 2011 May; 22(3):205-13. doi: 10.1002/pca.1266. [PMID: 21046685]
  • Rajender Kumar, Sandeep Kumar, Seema Sangwan, Inderjit Singh Yadav, Rakesh Yadav. Protein modeling and active site binding mode interactions of myrosinase-sinigrin in Brassica juncea--an in silico approach. Journal of molecular graphics & modelling. 2011 Feb; 29(5):740-6. doi: 10.1016/j.jmgm.2010.12.004. [PMID: 21236711]
  • Arup Bhattacharya, Yun Li, Kristina L Wade, Joseph D Paonessa, Jed W Fahey, Yuesheng Zhang. Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion. Carcinogenesis. 2010 Dec; 31(12):2105-10. doi: 10.1093/carcin/bgq202. [PMID: 20889681]
  • Monika Okulicz. Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats. Plant foods for human nutrition (Dordrecht, Netherlands). 2010 Sep; 65(3):217-24. doi: 10.1007/s11130-010-0183-3. [PMID: 20809411]
  • Kody A Belliveau, Laura B Romero-Zerón. Monitoring the enzymatic degradation of sinigrin from B. juncea meal using (1)H NMR spectroscopy. Natural product research. 2010; 24(1):24-33. doi: 10.1080/14786410802278285. [PMID: 20013469]
  • Lei-Lei Wang, Cong Chen, Min Zhou, Jian-Zhong Wang, Xia Luo, Guo Huang, Li-Ming Ye. [Determination of sinigrin in semen Thlaspi from Sichuan and Tibet using near infrared diffuse reflectance spectroscopy]. Guang pu xue yu guang pu fen xi = Guang pu. 2009 Oct; 29(10):2673-6. doi: ". [PMID: 20038035]
  • Derek Andersson, Romit Chakrabarty, Sarosh Bejai, Jiaming Zhang, Lars Rask, Johan Meijer. Myrosinases from root and leaves of Arabidopsis thaliana have different catalytic properties. Phytochemistry. 2009 Jul; 70(11-12):1345-54. doi: 10.1016/j.phytochem.2009.07.036. [PMID: 19703694]
  • Sabine Montaut, Julie Grandbois, Laura Righetti, Jessica Barillari, Renato Iori, Patrick Rollin. Updated glucosinolate profile of Dithyrea wislizenii. Journal of natural products. 2009 May; 72(5):889-93. doi: 10.1021/np800738w. [PMID: 19334740]
  • Jóska Gerendás, Jana Podestát, Thorsten Stahl, Kerstin Kübler, Hans Brückner, Volker Mersch-Sundermann, Karl H Mühling. Interactive effects of sulfur and nitrogen supply on the concentration of sinigrin and allyl isothiocyanate in Indian mustard (Brassica juncea L.). Journal of agricultural and food chemistry. 2009 May; 57(9):3837-44. doi: 10.1021/jf803636h. [PMID: 19309148]
  • Simone J Rochfort, V Craige Trenerry, Michael Imsic, Joe Panozzo, Rod Jones. Class targeted metabolomics: ESI ion trap screening methods for glucosinolates based on MSn fragmentation. Phytochemistry. 2008 May; 69(8):1671-9. doi: 10.1016/j.phytochem.2008.02.010. [PMID: 18396302]
  • Richard Lankau. A chemical trait creates a genetic trade-off between intra- and interspecific competitive ability. Ecology. 2008 May; 89(5):1181-7. doi: 10.1890/07-1541.1. [PMID: 18543611]
  • Vanessa Rungapamestry, Sylvie Rabot, Zoë Fuller, Brian Ratcliffe, Alan J Duncan. Influence of cooking duration of cabbage and presence of colonic microbiota on the excretion of N-acetylcysteine conjugates of allyl isothiocyanate and bioactivity of phase 2 enzymes in F344 rats. The British journal of nutrition. 2008 Apr; 99(4):773-81. doi: 10.1017/s0007114507841134. [PMID: 17967216]
  • Corin Pratt, Tom W Pope, Glen Powell, John T Rossiter. Accumulation of glucosinolates by the cabbage aphid Brevicoryne brassicae as a defense against two coccinellid species. Journal of chemical ecology. 2008 Mar; 34(3):323-9. doi: 10.1007/s10886-007-9421-z. [PMID: 18270780]
  • Richard A Lankau, Sharon Y Strauss. Community complexity drives patterns of natural selection on a chemical defense of Brassica nigra. The American naturalist. 2008 Feb; 171(2):150-61. doi: 10.1086/524959. [PMID: 18197768]
  • Eleanna Kazana, Tom W Pope, Laurienne Tibbles, Matthew Bridges, John A Pickett, Atle M Bones, Glen Powell, John T Rossiter. The cabbage aphid: a walking mustard oil bomb. Proceedings. Biological sciences. 2007 Sep; 274(1623):2271-7. doi: 10.1098/rspb.2007.0237. [PMID: 17623639]
  • Richard A Lankau, Sharon Y Strauss. Mutual feedbacks maintain both genetic and species diversity in a plant community. Science (New York, N.Y.). 2007 Sep; 317(5844):1561-3. doi: 10.1126/science.1147455. [PMID: 17872447]
  • Kristina L Wade, Ian J Garrard, Jed W Fahey. Improved hydrophilic interaction chromatography method for the identification and quantification of glucosinolates. Journal of chromatography. A. 2007 Jun; 1154(1-2):469-72. doi: 10.1016/j.chroma.2007.04.034. [PMID: 17482632]
  • Richard A Lankau. Specialist and generalist herbivores exert opposing selection on a chemical defense. The New phytologist. 2007; 175(1):176-184. doi: 10.1111/j.1469-8137.2007.02090.x. [PMID: 17547677]
  • Vanessa Rungapamestry, Alan J Duncan, Zoë Fuller, Brian Ratcliffe. Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations. Journal of agricultural and food chemistry. 2006 Oct; 54(20):7628-34. doi: 10.1021/jf0607314. [PMID: 17002432]
  • Kristin C Lewis, F A Bazzaz, Qing Liao, Colin M Orians. Geographic patterns of herbivory and resource allocation to defense, growth, and reproduction in an invasive biennial, Alliaria petiolata. Oecologia. 2006 Jun; 148(3):384-95. doi: 10.1007/s00442-006-0380-9. [PMID: 16502001]
  • Giedrius Miliauskas, Teris A van Beek, Pieter de Waard, Rimantas P Venskutonis, Ernst J R Sudhölter. Comparison of analytical and semi-preparative columns for high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance. Journal of chromatography. A. 2006 Apr; 1112(1-2):276-84. doi: 10.1016/j.chroma.2005.11.059. [PMID: 16364345]
  • Eun-Sun Hwang, Hyong Joo Lee. Induction of quinone reductase by allylisothiocyanate (AITC) and the N-acetylcysteine conjugate of AITC in Hepa1c1c7 mouse hepatoma cells. BioFactors (Oxford, England). 2006; 26(1):7-15. doi: 10.1002/biof.5520260102. [PMID: 16614479]
  • Cheng-Wen Lin, Fuu-Jen Tsai, Chang-Hai Tsai, Chien-Chen Lai, Lei Wan, Tin-Yun Ho, Chang-Chi Hsieh, Pei-Dawn Lee Chao. Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds. Antiviral research. 2005 Oct; 68(1):36-42. doi: 10.1016/j.antiviral.2005.07.002. [PMID: 16115693]
  • Jessica Barillari, Renato Iori, Patrick Rollin, Françoise Hennion. Glucosinolates in the subantarctic crucifer Kerguelen cabbage (Pringlea antiscorbutica). Journal of natural products. 2005 Feb; 68(2):234-6. doi: 10.1021/np049822q. [PMID: 15730250]
  • Rafael Font, Mercedes Del Río, José M Fernández-Martínez, Antonio De Haro-Bailón. Use of near-infrared spectroscopy for screening the individual and total glucosinolate contents in Indian mustard seed (Brassica juncea L. Czern. & Coss.). Journal of agricultural and food chemistry. 2004 Jun; 52(11):3563-9. doi: 10.1021/jf0307649. [PMID: 15161231]
  • D-L Cheng, K Hashimoto, Y Uda. In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2004 Mar; 42(3):351-7. doi: 10.1016/j.fct.2003.09.008. [PMID: 14871576]
  • Marvin J Weil, Yanjun Zhang, Muraleedharan G Nair. Colon cancer proliferating desulfosinigrin in wasabi (Wasabia japonica). Nutrition and cancer. 2004; 48(2):207-13. doi: 10.1207/s15327914nc4802_11. [PMID: 15231456]
  • Gabrielle Rouzaud, Sheila A Young, Alan J Duncan. Hydrolysis of glucosinolates to isothiocyanates after ingestion of raw or microwaved cabbage by human volunteers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2004 Jan; 13(1):125-31. doi: 10.1158/1055-9965.epi-085-3. [PMID: 14744743]
  • E-S Hwang, E H Jeffery. Evaluation of urinary N-acetyl cysteinyl allyl isothiocyanate as a biomarker for intake and bioactivity of Brussels sprouts. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Dec; 41(12):1817-25. doi: 10.1016/s0278-6915(03)00235-7. [PMID: 14563407]
  • M Cassim Mohamed Iqbal, Christian Möllers. Uptake and distribution of sinigrin in microspore derived embryos of Brassica napus L. Journal of plant physiology. 2003 Aug; 160(8):961-6. doi: 10.1078/0176-1617-00527. [PMID: 12964872]
  • M Brian Traw. Is induction response negatively correlated with constitutive resistance in black mustard?. Evolution; international journal of organic evolution. 2002 Nov; 56(11):2196-205. doi: 10.1111/j.0014-3820.2002.tb00144.x. [PMID: 12487350]
  • Rong Tsao, Qing Yu, John Potter, Mikio Chiba. Direct and simultaneous analysis of sinigrin and allyl isothiocyanate in mustard samples by high-performance liquid chromatography. Journal of agricultural and food chemistry. 2002 Aug; 50(17):4749-53. doi: 10.1021/jf0200523. [PMID: 12166955]
  • Cyrille Krul, Christèle Humblot, Catherine Philippe, Martijn Vermeulen, Marleen van Nuenen, Robert Havenaar, Sylvie Rabot. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis. 2002 Jun; 23(6):1009-16. doi: 10.1093/carcin/23.6.1009. [PMID: 12082023]
  • Matthew Bridges, Alexandra M E Jones, Atle M Bones, Chris Hodgson, Rosemary Cole, Elspeth Bartlet, Roger Wallsgrove, Vassiliki K Karapapa, Nigel Watts, John T Rossiter. Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant. Proceedings. Biological sciences. 2002 Jan; 269(1487):187-91. doi: 10.1098/rspb.2001.1861. [PMID: 11798435]
  • C Y Zhu, S Loft. Effects of Brussels sprouts extracts on hydrogen peroxide-induced DNA strand breaks in human lymphocytes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Dec; 39(12):1191-7. doi: 10.1016/s0278-6915(01)00061-8. [PMID: 11696392]
  • B Combourieu, L Elfoul, A M Delort, S Rabot. Identification of new derivatives of sinigrin and glucotropaeolin produced by the human digestive microflora using 1H NMR spectroscopy analysis of in vitro incubations. Drug metabolism and disposition: the biological fate of chemicals. 2001 Nov; 29(11):1440-5. doi: . [PMID: 11602519]
  • J F Jen, T H Lin, J W Huang, W C Chung. Direct determination of sinigrin in mustard seed without desulfatation by reversed-phase ion-pair liquid chromatography. Journal of chromatography. A. 2001 Apr; 912(2):363-8. doi: 10.1016/s0021-9673(01)00591-x. [PMID: 11330806]
  • A M Szmigielska, J J Schoenau. Use of anion-exchange membrane extraction for the high-performance liquid chromatographic analysis of mustard seed glucosinolates. Journal of agricultural and food chemistry. 2000 Nov; 48(11):5190-4. doi: 10.1021/jf0003000. [PMID: 11087457]
  • P J Kelly, A Bones, J T Rossiter. Sub-cellular immunolocalization of the glucosinolate sinigrin in seedlings of Brassica juncea. Planta. 1998 Oct; 206(3):370-7. doi: 10.1007/s004250050412. [PMID: 9763706]
  • S Cottaz, B Henrissat, H Driguez. Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase. Biochemistry. 1996 Dec; 35(48):15256-9. doi: 10.1021/bi9622480. [PMID: 8952475]
  • M G Botti, M G Taylor, N P Botting. Studies on the mechanism of myrosinase. Investigation of the effect of glycosyl acceptors on enzyme activity. The Journal of biological chemistry. 1995 Sep; 270(35):20530-5. doi: 10.1074/jbc.270.35.20530. [PMID: 7657629]
  • M Llanos Palop, J P Smiths, B T Brink. Degradation of sinigrin by Lactobacillus agilis strain R16. International journal of food microbiology. 1995 Jul; 26(2):219-29. doi: 10.1016/0168-1605(95)00123-2. [PMID: 7577359]
  • H B Shen. [Comparison between the sinigrin content of the Sinapis (Brassica juncea) before and after processing]. Zhong yao tong bao (Beijing, China : 1981). 1987 Apr; 12(4):18-20. doi: ". [PMID: 2964284]
  • A P Wilkinson, M J Rhodes, G R Fenwick. Determination of myrosinase (thioglucoside glucohydrolase) activity by a spectrophotometric coupled enzyme assay. Analytical biochemistry. 1984 Jun; 139(2):284-91. doi: 10.1016/0003-2697(84)90004-6. [PMID: 6476365]
  • V K Srivastava, D C Hill. Thiocyanate ion formation in rapeseed meals. Canadian journal of biochemistry. 1975 May; 53(5):630-3. doi: 10.1139/o75-085. [PMID: 1139401]
  • M MATSUO, M YAMAZAKI. Biosynthesis of sinigrin. Chemical & pharmaceutical bulletin. 1963 Apr; 11(?):545-7. doi: 10.1248/cpb.11.545. [PMID: 13933791]