Hesperetin 7-neohesperidoside (BioDeep_00000000079)
Secondary id: BioDeep_00000400526
natural product human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C28H34O15 (610.1897614000001)
中文名称: 新桔皮苷, 新橙皮甙, 新橙皮苷, 柑果苷
谱图信息:
最多检出来源 Viridiplantae(plant) 3.96%
分子结构信息
SMILES: c(O)(c3)c(C(=O)2)c(cc3O[C@H](O5)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)5)O[C@H](O4)[C@H](O)[C@H](O)[C@@H](O)[C@H](C)4)O[C@@H](C2)c(c1)ccc(c1O)OC
InChI: InChI=1/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
描述信息
Neohesperidin is a flavanone glycoside that is hesperitin having an 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group. It has a role as an antineoplastic agent and a plant metabolite. It is a neohesperidoside, a disaccharide derivative, a dihydroxyflavanone, a member of 3-hydroxyflavanones, a monomethoxyflavanone, a flavanone glycoside and a member of 4-methoxyflavanones. It is functionally related to a hesperetin.
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one is a natural product found in Citrus medica, Arabidopsis thaliana, and other organisms with data available.
Constituent of Seville orange peel (Citrus aurantium) and other Citrus subspecies Very bitter flavouring agent. Hesperetin 7-neohesperidoside is found in many foods, some of which are grapefruit/pummelo hybrid, pummelo, citrus, and grapefruit.
Hesperetin 7-neohesperidoside is found in citrus. Hesperetin 7-neohesperidoside is a constituent of Seville orange peel (Citrus aurantium) and other Citrus species Very bitter flavouring agent
Neohesperidin is a flavonoid compound found in high amounts in citrus fruits with anti-oxidant and anti-inflammatory effects.
Neohesperidin is a flavonoid compound found in high amounts in citrus fruits with anti-oxidant and anti-inflammatory effects.
同义名列表
31 个代谢物同义名
(S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one; (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one; 7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; 7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one; 4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (2S)-; 4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-; 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-; 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-; (S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside; FLAVANONE, 3,5,7-TRIHYDROXY-4-METHOXY-, 7-(2-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE); (S)-4-Methoxy-3,5,7-trihydroxyflavanone-7-[2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside]; Neohesperidin, United States Pharmacopeia (USP) Reference Standard; 8-HYDROXYQUINOLINE-2-CARBOXALDEHYDE8-QUINOLYLHYDRAZONE; 5-18-05-00219 (Beilstein Handbook Reference); Neohesperidin, analytical standard; Hesperetin 7-O-neohesperidoside; Hesperetin-7-O-neohesperidoside; Hesperetin-7-neohesperidoside; Hesperetin 7-neohesperidoside; ARGKVCXINMKCAZ-UZRWAPQLSA-N; NEOHESPERIDIN [USP-RS]; Neohesperidin, >=90\\%; NEOHESPERIDIN [INCI]; (2S)-NEOHESPERIDIN; UNII-OA5C88H3L0; Neohesperidin; SMP1_000209; OA5C88H3L0
数据库引用编号
37 个数据库交叉引用编号
- ChEBI: CHEBI:192003
- ChEBI: CHEBI:59016
- KEGG: C09806
- PubChem: 45358138
- PubChem: 232990
- PubChem: 442439
- HMDB: HMDB0030748
- Metlin: METLIN3679
- ChEMBL: CHEMBL4297019
- ChEMBL: CHEMBL506398
- Wikipedia: Neohesperidin
- LipidMAPS: LMPK12140452
- MeSH: neohesperidin
- ChemIDplus: 0013241333
- MetaCyc: CPD-7074
- KNApSAcK: C00000987
- foodb: FDB002679
- chemspider: 390879
- chemspider: 203119
- CAS: 13241-33-3
- MoNA: PS086012
- MoNA: PS086002
- MoNA: PS086011
- MoNA: PR020045
- MoNA: PS086009
- MoNA: PS086010
- MoNA: PS086008
- MoNA: PS086007
- MoNA: PS086005
- MoNA: PS086004
- MoNA: PS086001
- MoNA: PS086003
- medchemexpress: HY-N0101
- PMhub: MS000002795
- PubChem: 11994
- 3DMET: B03303
- NIKKAJI: J15.272B
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)
20 个相关的物种来源信息
- 3702 - Arabidopsis thaliana: 10.1111/TPJ.14594
- 558547 - Citrus deliciosa:
- 558547 - Citrus deliciosa: 10.1080/00021369.1979.10863651
- 37334 - Citrus maxima:
- 171251 - Citrus medica:
- 85571 - Citrus reticulata:
- 85571 - Citrus Reticulata: -
- 85571 - Citrus reticulata: 10.1080/00021369.1979.10863651
- 85571 - Citrus reticulata Blanco: -
- 558546 - Citrus sudachi:
- 37690 - Citrus trifoliata:
- 37690 - Citrus trifoliata: 10.1080/00021369.1979.10863651
- 55188 - Citrus unshiu:
- 55188 - Citrus unshiu: 10.1080/00021369.1979.10863651
- 475932 - Citrus wilsonii:
- 392618 - Cunila: 10.1007/S00299-018-2303-8
- 9606 - Homo sapiens: -
- 33090 - Plants: -
- 714512 - Uncaria hirsuta: 10.1002/JCCS.199400031
- 33090 - 枳壳: -
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
- Adel T Osman, Souty M Z Sharkawi, Mohamed I A Hassan, Amira M Abo-Youssef, Ramadan A M Hemeida. Empagliflozin and neohesperidin protect against methotrexate-induced renal toxicity via suppression of oxidative stress and inflammation in male rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2021 Sep; 155(?):112406. doi:
10.1016/j.fct.2021.112406
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Chemical & pharmaceutical bulletin.
2021 Aug; 69(8):741-746. doi:
10.1248/cpb.c21-00180
. [PMID: 34024880] - Naymul Karim, Mohammad Rezaul Islam Shishir, Ahmed K Rashwan, Huihui Ke, Wei Chen. Suppression of palmitic acid-induced hepatic oxidative injury by neohesperidin-loaded pectin-chitosan decorated nanoliposomes.
International journal of biological macromolecules.
2021 Jul; 183(?):908-917. doi:
10.1016/j.ijbiomac.2021.05.010
. [PMID: 33965489] - Yi-Kun Wang, Zi-Meng Zhou, Man-Yun Dai, Xiao-Fang Ma, Xue-Rong Xiao, Shou-Wen Zhang, Hong-Ning Liu, Fei Li. Discovery and validation of quality markers of Fructus Aurantii against acetylcholinesterase using metabolomics and bioactivity assays.
Journal of separation science.
2021 Jun; 44(11):2189-2205. doi:
10.1002/jssc.202001190
. [PMID: 33784419] - Yue-Wen Chang, Wen-Jun Zhu, Wei Gu, Jun Sun, Zhi-Qiang Li, Xiao-En Wei. Neohesperidin promotes the osteogenic differentiation of bone mesenchymal stem cells by activating the Wnt/β-catenin signaling pathway.
Journal of orthopaedic surgery and research.
2021 May; 16(1):334. doi:
10.1186/s13018-021-02468-5
. [PMID: 34020675] - Feng-Xiang Zhang, Yu-Lin-Lan Yuan, Shuang-Shuang Cui, Min Li, Xuan Tan, Zuo-Cheng Qiu, Rui-Man Li. Dissection of the potential pharmacological function of neohesperidin dihydrochalcone - a food additive - by in vivo substances profiling and network pharmacology.
Food & function.
2021 May; 12(10):4325-4336. doi:
10.1039/d1fo00104c
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Food chemistry.
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Journal of separation science.
2020 Oct; 43(19):3793-3805. doi:
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Nutrients.
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Molecules (Basel, Switzerland).
2019 Nov; 24(23):. doi:
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. [PMID: 31766682] - Chunxia Guo, Hua Zhang, Xin Guan, Zhiqin Zhou. The Anti-Aging Potential of Neohesperidin and Its Synergistic Effects with Other Citrus Flavonoids in Extending Chronological Lifespan of Saccharomyces Cerevisiae BY4742.
Molecules (Basel, Switzerland).
2019 Nov; 24(22):. doi:
10.3390/molecules24224093
. [PMID: 31766122] - Yanling Gong, Rong Dong, Xiaomeng Gao, Jin Li, Li Jiang, Jiale Zheng, Sunliang Cui, Meidan Ying, Bo Yang, Ji Cao, Qiaojun He. Neohesperidin prevents colorectal tumorigenesis by altering the gut microbiota.
Pharmacological research.
2019 10; 148(?):104460. doi:
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. [PMID: 31560944] - Yongjing Liu, Hua Zhang, Hongmin Yu, Suhua Guo, Dawei Chen. Deep eutectic solvent as a green solvent for enhanced extraction of narirutin, naringin, hesperidin and neohesperidin from Aurantii Fructus.
Phytochemical analysis : PCA.
2019 Mar; 30(2):156-163. doi:
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Molecules (Basel, Switzerland).
2018 Mar; 23(4):. doi:
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Food research international (Ottawa, Ont.).
2017 07; 97(?):1-6. doi:
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Chinese journal of integrative medicine.
2017 May; 23(5):370-375. doi:
10.1007/s11655-016-2593-z
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Pharmacology.
2017; 100(3-4):115-126. doi:
10.1159/000452492
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Food chemistry.
2016 Aug; 204(?):167-175. doi:
10.1016/j.foodchem.2016.02.012
. [PMID: 26988490] - Sheng Jia, Ying Hu, Wenna Zhang, Xiaoyong Zhao, Yanhong Chen, Chongde Sun, Xian Li, Kunsong Chen. Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L. in diabetic KK-A(y) mice.
Food & function.
2015 Mar; 6(3):878-86. doi:
10.1039/c4fo00993b
. [PMID: 25620042] - See-Lok Ho, Chung-Yan Poon, Chengyuan Lin, Ting Yan, Daniel Wai-Jing Kwong, Ken Kin-Lam Yung, Man S Wong, Zhaoxiang Bian, Hung-Wing Li. Inhibition of β-amyloid Aggregation By Albiflorin, Aloeemodin And Neohesperidin And Their Neuroprotective Effect On Primary Hippocampal Cells Against β-amyloid Induced Toxicity.
Current Alzheimer research.
2015; 12(5):424-33. doi:
10.2174/1567205012666150504144919
. [PMID: 25938872] - Dalia I Hamdan, Mona F Mahmoud, Michael Wink, Assem M El-Shazly. Effect of hesperidin and neohesperidin from bittersweet orange (Citrus aurantium var. bigaradia) peel on indomethacin-induced peptic ulcers in rats.
Environmental toxicology and pharmacology.
2014 May; 37(3):907-15. doi:
10.1016/j.etap.2014.03.006
. [PMID: 24691249] - Kyung-Chul Shin, Hyun-Koo Nam, Deok-Kun Oh. Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts.
Journal of agricultural and food chemistry.
2013 Nov; 61(47):11532-40. doi:
10.1021/jf403332e
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Journal of food science.
2013 Jan; 78(1):C37-42. doi:
10.1111/j.1750-3841.2012.03002.x
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Food chemistry.
2012 Dec; 135(3):1667-75. doi:
10.1016/j.foodchem.2012.05.095
. [PMID: 22953908] - Jiukai Zhang, Chongde Sun, Youyou Yan, Qingjun Chen, Fenglei Luo, Xiaoyan Zhu, Xian Li, Kunsong Chen. Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells.
Food chemistry.
2012 Dec; 135(3):1471-8. doi:
10.1016/j.foodchem.2012.06.004
. [PMID: 22953882] - Jingze Zhang, Wenyuan Gao, Xiao Hu, Zhen Liu, Changxiao Liu. The influence of compatibility of traditional Chinese medicine on the pharmacokinetic of main components in Fructus aurantii.
Journal of ethnopharmacology.
2012 Nov; 144(2):277-83. doi:
10.1016/j.jep.2012.09.009
. [PMID: 23000113] - Fei Xu, Jia Zang, Daozhen Chen, Ting Zhang, Huiying Zhan, Mudan Lu, Hongxiang Zhuge. Neohesperidin induces cellular apoptosis in human breast adenocarcinoma MDA-MB-231 cells via activating the Bcl-2/Bax-mediated signaling pathway.
Natural product communications.
2012 Nov; 7(11):1475-8. doi:
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Journal of food science.
2012 Sep; 77(9):C921-6. doi:
10.1111/j.1750-3841.2012.02865.x
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Journal of agricultural and food chemistry.
2012 Aug; 60(32):7973-80. doi:
10.1021/jf301848s
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Immunopharmacology and immunotoxicology.
2012 Aug; 34(4):661-6. doi:
10.3109/08923973.2011.649289
. [PMID: 22239430] - Adriana C E Graziano, Venera Cardile, Lucia Crascì, Sivia Caggia, Paola Dugo, Francesco Bonina, Annamaria Panico. Protective effects of an extract from Citrus bergamia against inflammatory injury in interferon-γ and histamine exposed human keratinocytes.
Life sciences.
2012 Jun; 90(25-26):968-74. doi:
10.1016/j.lfs.2012.04.043
. [PMID: 22634580] - Lei Zhang, Lin Zhu, Yuefei Wang, Zhenzuo Jiang, Xin Chai, Yan Zhu, Xiumei Gao, Aidi Qi. Characterization and quantification of major constituents of Xue Fu Zhu Yu by UPLC-DAD-MS/MS.
Journal of pharmaceutical and biomedical analysis.
2012 Mar; 62(?):203-9. doi:
10.1016/j.jpba.2011.12.026
. [PMID: 22264846] - Ling Tong, Dandan Zhou, Jun Gao, Yonghong Zhu, He Sun, Kaishun Bi. Simultaneous determination of naringin, hesperidin, neohesperidin, naringenin and hesperetin of Fractus aurantii extract in rat plasma by liquid chromatography tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2012 Jan; 58(?):58-64. doi:
10.1016/j.jpba.2011.05.001
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Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):607584. doi:
10.1155/2012/607584
. [PMID: 22454671] - Chung-Hung Shih, Ling-Hung Lin, Hsin-Te Hsu, Kuo-Hsien Wang, Chi-Yin Lai, Chien-Ming Chen, Wun-Chang Ko. Hesperetin, a Selective Phosphodiesterase 4 Inhibitor, Effectively Suppresses Ovalbumin-Induced Airway Hyperresponsiveness without Influencing Xylazine/Ketamine-Induced Anesthesia.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):472897. doi:
10.1155/2012/472897
. [PMID: 22454667] - Trupti Joshi, Kapil Patil, Michael R Fitzpatrick, Levi D Franklin, Qiuming Yao, Jeffrey R Cook, Zheng Wang, Marc Libault, Laurent Brechenmacher, Babu Valliyodan, Xiaolei Wu, Jianlin Cheng, Gary Stacey, Henry T Nguyen, Dong Xu. Soybean Knowledge Base (SoyKB): a web resource for soybean translational genomics.
BMC genomics.
2012; 13 Suppl 1(?):S15. doi:
10.1186/1471-2164-13-s1-s15
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Journal of separation science.
2012 Jan; 35(1):128-36. doi:
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2011 Dec; 50(8):681-8. doi:
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Journal of biomedical science.
2011 Nov; 18(?):84. doi:
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2011 Nov; 46(11):1374-9. doi:
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Zeitschrift fur Naturforschung. C, Journal of biosciences.
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Analytical and bioanalytical chemistry.
2011 Mar; 399(9):3211-9. doi:
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ISRN pharmacology.
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2010 Jul; 35(14):1850-4. doi:
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Biomedical chromatography : BMC.
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Journal of agricultural and food chemistry.
2009 Nov; 57(22):10933-42. doi:
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Journal of natural medicines.
2009 Oct; 63(4):443-50. doi:
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Biological & pharmaceutical bulletin.
2009 Mar; 32(3):410-5. doi:
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Analytica chimica acta.
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Biological & pharmaceutical bulletin.
2008 May; 31(5):925-30. doi:
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2008 Apr; 46(5):864-9. doi:
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Journal of agricultural and food chemistry.
2007 Dec; 55(26):10671-7. doi:
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2007 Dec; 103(6):2056-64. doi:
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Journal of pharmaceutical and biomedical analysis.
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Plant foods for human nutrition (Dordrecht, Netherlands).
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BMC pharmacology.
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