5-Methyltetrahydrofolate (BioDeep_00000016512)
Main id: BioDeep_00000001267
natural product PANOMIX_OTCML-2023
代谢物信息卡片
5-methyltetrahydrofolic acid disodium salt
化学式: C20H25N7O6 (459.1866)
中文名称: 甲基叶酸盐
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1C(CNC2=C1C(=O)N=C(N2)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m0/s1
描述信息
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
5-Methyltetrahydrofolic acid (5-Methyl THF) is a biologically active form of folic acid. 5-Methyltetrahydrofolic acid is a methylated derivate of tetrahydrofolate. 5-Methyltetrahydrofolic acid is the predominant natural dietary folate and the principal form of folate in plasma and cerebrospinal fluid[1].
同义名列表
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
9 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(7)
- folate transformations I:
NAD+ + gly + tetrahydrofolate ⟶ 5,10-methylenetetrahydrofolate + CO2 + H+ + NADH + ammonia - methionine biosynthesis I:
H2O + L-cystathionine ⟶ H+ + L-homocysteine + ammonia + pyruvate - superpathway of methionine biosynthesis (by sulfhydrylation):
2-oxoglutarate + asp ⟶ glt + oxaloacetate - homoserine and methionine biosynthesis:
H2O + L-cystathionine ⟶ H+ + L-homocysteine + ammonia + pyruvate - superpathway of methionine biosynthesis (transsulfuration):
H2O + L-cystathionine ⟶ H+ + L-homocysteine + ammonia + pyruvate - methionine biosynthesis III:
5-methyltetrahydropteroyltri-L-glutamate + H+ + L-homocysteine ⟶ met + tetrahydropteroyl tri-L-glutamate - formylTHF biosynthesis I:
NAD+ + gly + tetrahydrofolate ⟶ 5,10-methylenetetrahydrofolate + CO2 + H+ + NADH + ammonia
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(1)
- @COVID-19 Disease
Map["name"]:
2-Methyl-3-acetoacetyl-CoA + Coenzyme A ⟶ Acetyl-CoA + Propanoyl-CoA
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
- 40321 - Capsicum annuum var. annuum: 10.1021/JF062327A
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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Han Yang, Jinning Yang, Cheng Liu, Xueqin Lv, Long Liu, Jianghua Li, Guocheng Du, Jian Chen, Yanfeng Liu. High-Level 5-Methyltetrahydrofolate Bioproduction in Bacillus subtilis by Combining Modular Engineering and Transcriptomics-Guided Global Metabolic Regulation.
Journal of agricultural and food chemistry.
2022 May; 70(19):5849-5859. doi:
10.1021/acs.jafc.2c01252. [PMID: 35521920] - Yu Cheng, Shuai Liu, Duo Chen, Yiman Yang, Qiongyue Liang, Ya Huo, Ziyi Zhou, Nan Zhang, Zhuo Wang, Lishun Liu, Yun Song, Xiangyi Liu, Yong Duan, Xiuwen Liang, Bingjie Hou, Binyan Wang, Genfu Tang, Xianhui Qin, Fangrong Yan. Association between serum 5-methyltetrahydrofolate and homocysteine in Chinese hypertensive participants with different MTHFR C677T polymorphisms: a cross-sectional study.
Nutrition journal.
2022 05; 21(1):29. doi:
10.1186/s12937-022-00786-w. [PMID: 35562805] - Ajana Pathikkal, Bijesh Puthusseri, Peethambaran Divya, Sudha Rudrappa, Vikas Singh Chauhan. Folate derivatives, 5-methyltetrahydrofolate and 10-formyltetrahydrofolate, protect BEAS-2B cells from high glucose-induced oxidative stress and inflammation.
In vitro cellular & developmental biology. Animal.
2022 May; 58(5):419-428. doi:
10.1007/s11626-022-00691-w. [PMID: 35678985] - Hong Wu, Zhengduo Zhang, Yuxin Wang, Tianran Zhang, Shaojun Qi, Yanjin Tang, Xibao Gao. Investigation into the Properties of L-5-Methyltetrahydrofolate and Seal Oil as a Potential Atherosclerosis Intervention in Rats.
Journal of nutritional science and vitaminology.
2022; 68(2):87-96. doi:
10.3177/jnsv.68.87. [PMID: 35491209] - Shaimaa M Sallam, Eman Shawky, Samah M El Sohafy. Determination of the effect of germination on the folate content of the seeds of some legumes using HPTLC-mass spectrometry-multivariate image analysis.
Food chemistry.
2021 Nov; 362(?):130206. doi:
10.1016/j.foodchem.2021.130206. [PMID: 34082289] - Zenglin Lian, Hong Chen, Kang Liu, Qianghua Jia, Feng Qiu, Yongzhi Cheng. Improved Stability of a Stable Crystal Form C of 6S-5-Methyltetrahydrofolate Calcium Salt, Method Development and Validation of an LC-MS/MS Method for Rat Pharmacokinetic Comparison.
Molecules (Basel, Switzerland).
2021 Oct; 26(19):. doi:
10.3390/molecules26196011. [PMID: 34641555] - Seok-Won Hyung, Sunyoung Lee, Jeesoo Han, Joonhee Lee, Song-Yee Beak, Byungjoo Kim, Kiwhan Choi, Seonghee Ahn. Highly sensitive analytical method for the accurate determination of 5-methyltetrahydrofolic acid monoglutamate in various volumes of human plasma using isotope dilution ultra-high performance liquid chromatography-mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2021 Aug; 1179(?):122725. doi:
10.1016/j.jchromb.2021.122725. [PMID: 34311437] - Xuanye Cao, Annika Wolf, Sung-Eun Kim, Robert M Cabrera, Bogdan J Wlodarczyk, Huiping Zhu, Margaret Parker, Ying Lin, John W Steele, Xiao Han, Vincent Th Ramaekers, Robert Steinfeld, Richard H Finnell, Yunping Lei. CIC de novo loss of function variants contribute to cerebral folate deficiency by downregulating FOLR1 expression.
Journal of medical genetics.
2021 07; 58(7):484-494. doi:
10.1136/jmedgenet-2020-106987. [PMID: 32820034] - Mengyi Liu, Zhuxian Zhang, Chun Zhou, Qinqin Li, Panpan He, Yuanyuan Zhang, Huan Li, Chengzhang Liu, Min Liang, Xiaobin Wang, Xiping Xu, Fan Fan Hou, Xianhui Qin. Relationship of several serum folate forms with the risk of mortality: A prospective cohort study.
Clinical nutrition (Edinburgh, Scotland).
2021 06; 40(6):4255-4262. doi:
10.1016/j.clnu.2021.01.025. [PMID: 33551219] - Emanuela Pannia, Rola Hammoud, Ruslan Kubant, Jong Yup Sa, Rebecca Simonian, Brandi Wasek, Paula Ashcraft, Teodoro Bottiglieri, Zdenka Pausova, G Harvey Anderson. High Intakes of [6S]-5-Methyltetrahydrofolic Acid Compared with Folic Acid during Pregnancy Programs Central and Peripheral Mechanisms Favouring Increased Food Intake and Body Weight of Mature Female Offspring.
Nutrients.
2021 Apr; 13(5):. doi:
10.3390/nu13051477. [PMID: 33925570] - Patrycja Guzik, Martina Benešová, Magdalena Ratz, Josep M Monné Rodríguez, Luisa M Deberle, Roger Schibli, Cristina Müller. Preclinical evaluation of 5-methyltetrahydrofolate-based radioconjugates-new perspectives for folate receptor-targeted radionuclide therapy.
European journal of nuclear medicine and molecular imaging.
2021 04; 48(4):972-983. doi:
10.1007/s00259-020-04980-y. [PMID: 33063250] - Pooja Dhiman, Raji Ramachandran Pillai, Anand Babu Wilson, Nancy Premkumar, Balaji Bharadwaj, Veena P Ranjan, Soundravally Rajendiran. Cross-sectional association between vitamin B12 status and probable postpartum depression in Indian women.
BMC pregnancy and childbirth.
2021 Feb; 21(1):146. doi:
10.1186/s12884-021-03622-x. [PMID: 33596868] - Dandan Sun, Yue Jin, Qingyu Zhao, Chaohua Tang, Yi Li, Hao Wang, Yuchang Qin, Junmin Zhang. Modified EMR-lipid method combined with HPLC-MS/MS to determine folates in egg yolks from laying hens supplemented with different amounts of folic acid.
Food chemistry.
2021 Feb; 337(?):127767. doi:
10.1016/j.foodchem.2020.127767. [PMID: 32799162] - Emanuela Pannia, Rola Hammoud, Rebecca Simonian, Erland Arning, Paula Ashcraft, Brandi Wasek, Teodoro Bottiglieri, Zdenka Pausova, Ruslan Kubant, G Harvey Anderson. [6S]-5-Methyltetrahydrofolic Acid and Folic Acid Pregnancy Diets Differentially Program Metabolic Phenotype and Hypothalamic Gene Expression of Wistar Rat Dams Post-Birth.
Nutrients.
2020 Dec; 13(1):. doi:
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Nutrients.
2020 Nov; 12(12):. doi:
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The American journal of clinical nutrition.
2020 11; 112(5):1304-1317. doi:
10.1093/ajcn/nqaa208. [PMID: 32844208] - Karen L Koenig, Stephanie Scarmo, Yelena Afanasyeva, Tess V Clendenen, Per Magne Ueland, Anne Zeleniuch-Jacquotte. Circulating unmetabolized folic acid and 5-methyltetrahydrofolate and risk of breast cancer: a nested case-control study.
European journal of clinical nutrition.
2020 09; 74(9):1306-1315. doi:
10.1038/s41430-020-0615-6. [PMID: 32317749] - Yubin Ji, Hongjun Luo, Hui Li, Zhexuan Lin, Wenhong Luo. Determination of plasma homocysteine with a UHPLC-MS/MS method: Application to analyze the correlation between plasma homocysteine and whole blood 5-methyltetrahydrofolate in healthy volunteers.
Biomedical chromatography : BMC.
2020 Aug; 34(8):e4845. doi:
10.1002/bmc.4845. [PMID: 32267542] - Han Yang, Yanfeng Liu, Jianghua Li, Long Liu, Guocheng Du, Jian Chen. Systems metabolic engineering of Bacillus subtilis for efficient biosynthesis of 5-methyltetrahydrofolate.
Biotechnology and bioengineering.
2020 07; 117(7):2116-2130. doi:
10.1002/bit.27332. [PMID: 32170863] - Alessandra Vezzoli, Cinzia Dellanoce, Teresa Maria Caimi, Daniele Vietti, Michela Montorsi, Simona Mrakic-Sposta, Roberto Accinni. Influence of Dietary Supplementation for Hyperhomocysteinemia Treatments.
Nutrients.
2020 Jun; 12(7):. doi:
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Nutrients.
2020 Jun; 12(6):. doi:
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The British journal of nutrition.
2020 05; 123(10):1187-1200. doi:
10.1017/s0007114520000422. [PMID: 32019627] - Kelsey M Cochrane, Chantal Mayer, Angela M Devlin, Rajavel Elango, Jennifer A Hutcheon, Crystal D Karakochuk. Is natural (6S)-5-methyltetrahydrofolic acid as effective as synthetic folic acid in increasing serum and red blood cell folate concentrations during pregnancy? A proof-of-concept pilot study.
Trials.
2020 May; 21(1):380. doi:
10.1186/s13063-020-04320-3. [PMID: 32370802] - Zia Fazili, Maya R Sternberg, Nancy Potischman, Chia-Yih Wang, Renee J Storandt, Lorraine Yeung, Sedigheh Yamini, Jaime J Gahche, WenYen Juan, Yan Ping Qi, Neelima Paladugula, Gwendolyn Gabey, Christine M Pfeiffer. Demographic, Physiologic, and Lifestyle Characteristics Observed with Serum Total Folate Differ Among Folate Forms: Cross-Sectional Data from Fasting Samples in the NHANES 2011-2016.
The Journal of nutrition.
2020 04; 150(4):851-860. doi:
10.1093/jn/nxz278. [PMID: 31875475] - Doreen Schmidl, Kinga Howorka, Stephan Szegedi, Kristina Stjepanek, Stefan Puchner, Ahmed Bata, Ulrike Scheschy, Gerold Aschinger, René M Werkmeister, Leopold Schmetterer, Gerhard Garhofer. A pilot study to assess the effect of a three-month vitamin supplementation containing L-methylfolate on systemic homocysteine plasma concentrations and retinal blood flow in patients with diabetes.
Molecular vision.
2020; 26(?):326-333. doi:
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Neurobiology of disease.
2019 12; 132(?):104613. doi:
10.1016/j.nbd.2019.104613. [PMID: 31525435] - Fanyue Meng, Guoqing Zhang, Caifen Wang, Rui Zhu, Haiyan Li, Jian Xu, Shailendra Shakya, Weidong Chen, Li Wu, Jiwen Zhang. Folic acid and its metabolite codetermination for pharmacokinetics with circadian rhythms and evaluation of oral bioavailability.
The Journal of pharmacy and pharmacology.
2019 Nov; 71(11):1645-1654. doi:
10.1111/jphp.13155. [PMID: 31435940] - Wansu Qiu, Aarthi R Gobinath, Yanhua Wen, Jehannine Austin, Liisa A M Galea. Folic acid, but not folate, regulates different stages of neurogenesis in the ventral hippocampus of adult female rats.
Journal of neuroendocrinology.
2019 10; 31(10):e12787. doi:
10.1111/jne.12787. [PMID: 31478270] - Chenfeng Xu, Wenkai Hui, Lili Sun, Qianqian Gao, Qiaogen Zou. [Simultaneous determination of leucovorin and 5-methyl-tetrahydrofolate diastereoisomers in human plasma by high-performance liquid chromatography-tandem mass spectrometry coupled with ultrafiltration centrifugation-based pretreatment and its application to a pharmacokinetic study].
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2019 Jun; 37(6):581-588. doi:
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Journal of chromatography. A.
2019 Jun; 1594(?):34-44. doi:
10.1016/j.chroma.2019.02.037. [PMID: 30799066] - Baiyi Li, Shaoyan Chang, Chi Liu, Min Zhang, Lianfeng Zhang, Liang Liang, Rui Li, Xiuwei Wang, Chuan Qin, Ting Zhang, Bo Niu, Li Wang. Low Maternal Dietary Folate Alters Retrotranspose by Methylation Regulation in Intrauterine Growth Retardation (IUGR) Fetuses in a Mouse Model.
Medical science monitor : international medical journal of experimental and clinical research.
2019 May; 25(?):3354-3365. doi:
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PloS one.
2019; 14(8):e0216790. doi:
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PloS one.
2019; 14(2):e0212255. doi:
10.1371/journal.pone.0212255. [PMID: 30789924] - Helena Taflin, Elisabeth Odin, Kristoffer Derwinger, Göran Carlsson, Bengt Gustavsson, Yvonne Wettergren. Relationship between folate concentration and expression of folate-associated genes in tissue and plasma after intraoperative administration of leucovorin in patients with colorectal cancer.
Cancer chemotherapy and pharmacology.
2018 12; 82(6):987-997. doi:
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Journal of clinical pathology.
2018 Nov; 71(11):949-956. doi:
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The Journal of nutritional biochemistry.
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Journal of cellular physiology.
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The Journal of nutrition.
2018 06; 148(6):885-890. doi:
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2018 Jun; 34(6):495-501. doi:
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The Journal of nutrition.
2018 05; 148(5):807-817. doi:
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Cardiovascular drugs and therapy.
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International journal of food sciences and nutrition.
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Molecular psychiatry.
2018 02; 23(2):316-322. doi:
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Journal of cardiovascular pharmacology.
2017 Oct; 70(4):271-275. doi:
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The Journal of nutrition.
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Molecular nutrition & food research.
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Methods in molecular biology (Clifton, N.J.).
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European journal of clinical nutrition.
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Experimental gerontology.
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Minerva ginecologica.
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The British journal of nutrition.
2015 Jun; 113(12):1965-77. doi:
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Nutrition research (New York, N.Y.).
2015 Jun; 35(6):489-95. doi:
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The Journal of nutrition.
2015 Mar; 145(3):520-31. doi:
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Food & function.
2015 Jan; 6(1):242-8. doi:
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Journal of nutritional science and vitaminology.
2015; 61(6):455-9. doi:
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Asian Pacific journal of cancer prevention : APJCP.
2015; 16(10):4383-6. doi:
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Arthritis & rheumatology (Hoboken, N.J.).
2014 Dec; 66(12):3476-85. doi:
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The Journal of nutrition.
2014 Nov; 144(11):1873-9. doi:
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Developmental neurobiology.
2014 Sep; 74(9):877-93. doi:
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The Journal of clinical psychiatry.
2014 Aug; 75(8):855-63. doi:
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The American journal of clinical nutrition.
2014 Aug; 100(2):593-9. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2014 Jul; 962(?):9-13. doi:
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European journal of nutrition.
2013 Oct; 52(7):1801-10. doi:
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The Cochrane database of systematic reviews.
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Ginekologia polska.
2013 Jul; 84(7):641-6. doi:
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The American journal of clinical nutrition.
2013 Jul; 98(1):42-8. doi:
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The Journal of nutrition.
2013 Jun; 143(6):867-71. doi:
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Food chemistry.
2013 Jun; 138(2-3):1982-91. doi:
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Analytical and bioanalytical chemistry.
2013 May; 405(13):4549-60. doi:
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Journal of agricultural and food chemistry.
2013 Apr; 61(16):3949-56. doi:
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Molecular psychiatry.
2013 Mar; 18(3):369-81. doi:
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Journal of agricultural and food chemistry.
2013 Jan; 61(1):247-54. doi:
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PloS one.
2013; 8(10):e77923. doi:
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Nature communications.
2013; 4(?):2123. doi:
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Journal of Alzheimer's disease : JAD.
2013; 33(4):1097-104. doi:
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Plant foods for human nutrition (Dordrecht, Netherlands).
2012 Dec; 67(4):401-6. doi:
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High blood pressure & cardiovascular prevention : the official journal of the Italian Society of Hypertension.
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The American journal of clinical nutrition.
2012 Oct; 96(4):789-800. doi:
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The Journal of clinical psychiatry.
2012 Jun; 73(6):843-8. doi:
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Pharmacogenetics and genomics.
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2012 Mar; 27(3):304-9. doi:
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The British journal of nutrition.
2012 Mar; 107(6):800-8. doi:
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Journal of nutrigenetics and nutrigenomics.
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Analytical and bioanalytical chemistry.
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The American journal of clinical nutrition.
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American journal of obstetrics and gynecology.
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The Journal of nutrition.
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Archives of neurology.
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