Narirutin (BioDeep_00000000193)

 

Secondary id: BioDeep_00000270575, BioDeep_00001103543

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

化学式: C27H32O14 (580.1791972)
中文名称: 柚皮芸香苷, 芸香柚皮苷
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.1%

分子结构信息

SMILES: C1(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]3[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)O2)C=C2O[C@]([H])(C3C=CC(O)=CC=3)CC(=O)C2=C(O)C=1
InChI: InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

描述信息

Narirutin is a disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an anti-inflammatory agent, an antioxidant and a metabolite. It is a disaccharide derivative, a dihydroxyflavanone, a member of 4-hydroxyflavanones, a (2S)-flavan-4-one and a rutinoside. It is functionally related to a (S)-naringenin.
Narirutin is a natural product found in Cyclopia subternata, Citrus latipes, and other organisms with data available.
See also: Tangerine peel (part of).
obtained from Camellia sinensis (tea). Narirutin is found in many foods, some of which are lemon, globe artichoke, grapefruit, and grapefruit/pummelo hybrid.
Narirutin is found in globe artichoke. Narirutin is obtained from Camellia sinensis (tea
Narirutin, one of the active constituents isolated from citrus fruits, has antioxidant and anti-inflammatory activities. Narirutin is a shikimate kinase inhibitor with anti-tubercular potency[1][2].
Narirutin, one of the active constituents isolated from citrus fruits, has antioxidant and anti-inflammatory activities. Narirutin is a shikimate kinase inhibitor with anti-tubercular potency[1][2].

同义名列表

35 个代谢物同义名

(S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one; (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)chroman-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2H-1-benzopyran-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-2,3-dihydro-1-benzopyran-4-one; 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-; 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-; (2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpa-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-; 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoxyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-; (2S)-7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; (S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside; FLAVANONE, 4,5,7-TRIHYDROXY-, 7.BETA.-RUTINOSIDE; Flavanone, 4,5,7-trihydroxy-, 7-beta-rutinoside; FLAVANONE, 4,5,7-TRIHYDROXY-, 7beta-RUTINOSIDE; NARINGENIN 7.BETA.-RUTINOSIDE; Naringenin 7-beta-rutinoside; NARINGENIN 7beta-RUTINOSIDE; Naringenin 7-O-rutinoside; Naringenin-7-O-rutinoside; Narirutin, >=98\\% (HPLC); Naringenin 7-rutinoside; ISONARINGIN (USP-RS); ISONARINGIN [USP-RS]; BrovincamineFumarte; NARIRUTIN [INCI]; UNII-06M5EAT0YC; (2S)-Narirutin; Isonaringenin; Isonaringin; 06M5EAT0YC; Narirutin



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

9 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(8)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

159 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

  • Seung Tae Im, Heejoo Kang, Jusang Kim, Song-Rae Kim, Kil-Nam Kim, Seung-Hong Lee. Narirutin-Rich Celluclast Extract from Mandarin (Citrus unshiu) Peel Alleviates High-Fat Diet-Induced Obesity and Promotes Energy Metabolism in C57BL/6 Mice. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084475. [PMID: 38674060]
  • Ki-Hoon Park, Haytham Mohamedelfatih Mohamed Makki, Seok-Hyung Kim, Hyung-Joo Chung, Junyang Jung. Narirutin ameliorates alcohol-induced liver injury by targeting MAPK14 in zebrafish larvae. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Aug; 166(?):115350. doi: 10.1016/j.biopha.2023.115350. [PMID: 37633055]
  • Saikat Mitra, Mashia Subha Lami, Tanvir Mahtab Uddin, Rajib Das, Fahadul Islam, Juhaer Anjum, Md Jamal Hossain, Talha Bin Emran. Prospective multifunctional roles and pharmacological potential of dietary flavonoid narirutin. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jun; 150(?):112932. doi: 10.1016/j.biopha.2022.112932. [PMID: 35413599]
  • Paresh Patel, Kalyani Barve, Lokesh Kumar Bhatt. Narirutin-rich fraction from grape fruit peel protects against transient cerebral ischemia reperfusion injury in rats. Nutritional neuroscience. 2022 May; 25(5):920-930. doi: 10.1080/1028415x.2020.1821518. [PMID: 32965176]
  • Hui Zheng, Xiao-Ting Zhen, Yan Chen, Si-Chen Zhu, Li-Hong Ye, Si-Wei Yang, Qiu-Yan Wang, Jun Cao. In situ antioxidation-assisted matrix solid-phase dispersion microextraction and discrimination of chiral flavonoids from citrus fruit via ion mobility quadrupole time-of-flight high-resolution mass spectrometry. Food chemistry. 2021 May; 343(?):128422. doi: 10.1016/j.foodchem.2020.128422. [PMID: 33143965]
  • Sainan Li, Chunming Liu, Yuchi Zhang, Dongfang Shi, Rong Tsao. Application of accelerated solvent extraction coupled with online two-dimensional countercurrent chromatography for continuous extraction and separation of bioactive compounds from Citrus limon peel. Journal of separation science. 2020 Oct; 43(19):3793-3805. doi: 10.1002/jssc.202000588. [PMID: 32745365]
  • Min Hou, Emilie Combet, Christine Ann Edwards. Pulp in Shop-Bought Orange Juice Has Little Effect on Flavonoid Content and Gut Bacterial Flavanone Degradation In Vitro. Plant foods for human nutrition (Dordrecht, Netherlands). 2019 Sep; 74(3):383-390. doi: 10.1007/s11130-019-00739-5. [PMID: 31228035]
  • Balakrishnan Shammugasamy, Peter Valtchev, Qihan Dong, Fariba Dehghani. Effect of citrus peel extracts on the cellular quiescence of prostate cancer cells. Food & function. 2019 Jun; 10(6):3727-3737. doi: 10.1039/c9fo00455f. [PMID: 31169845]
  • 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: 10.1002/pca.2801. [PMID: 30426588]
  • Jungwhoi Lee, Dong-Shik Yang, Song-I Han, Jeong Hun Yun, Il-Woong Kim, Seung Jun Kim, Jae Hoon Kim. Aqueous Extraction of Citrus unshiu Peel Induces Proangiogenic Effects Through the FAK and ERK1/2 Signaling Pathway in Human Umbilical Vein Endothelial Cells. Journal of medicinal food. 2016 Jun; 19(6):569-77. doi: 10.1089/jmf.2015.3584. [PMID: 27266341]
  • Li-Na Liu, Ying Wang, Hong-Yu Jin, Shuang-Cheng Ma, Jia-Peng Liu. Application of immunoaffinity purification technology as the pretreatment technology for traditional Chinese medicine: Its application to analysis of hesperidin and narirutin in traditional Chinese medicine preparations containing Citri reticulatae Pericarpium. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 May; 1021(?):122-128. doi: 10.1016/j.jchromb.2015.10.005. [PMID: 26526495]
  • Takao Ohashi, Yuka Hasegawa, Ryo Misaki, Kazuhito Fujiyama. Substrate preference of citrus naringenin rhamnosyltransferases and their application to flavonoid glycoside production in fission yeast. Applied microbiology and biotechnology. 2016 Jan; 100(2):687-96. doi: 10.1007/s00253-015-6982-6. [PMID: 26433966]
  • 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. [PMID: 24188428]
  • Kazuya Murata, Seiya Takano, Megumi Masuda, Munekazu Iinuma, Hideaki Matsuda. Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits. Journal of natural medicines. 2013 Jul; 67(3):643-6. doi: 10.1007/s11418-012-0699-y. [PMID: 22903244]
  • Ho-Young Park, Sang Keun Ha, Hyojin Eom, Inwook Choi. Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 May; 55(?):637-44. doi: 10.1016/j.fct.2013.01.060. [PMID: 23416143]
  • Yujing Sun, Liping Qiao, Yan Shen, Ping Jiang, Jianchu Chen, Xingqian Ye. Phytochemical profile and antioxidant activity of physiological drop of citrus fruits. Journal of food science. 2013 Jan; 78(1):C37-42. doi: 10.1111/j.1750-3841.2012.03002.x. [PMID: 23301602]
  • Priyanka Chaudhary, G K Jayaprakasha, Ron Porat, Bhimanagouda S Patil. Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds. Food chemistry. 2012 Dec; 135(3):1667-75. doi: 10.1016/j.foodchem.2012.05.095. [PMID: 22953908]
  • Jun Tae Bae, Hyun Ju Ko, Gyoung Bum Kim, Hyeong Bae Pyo, Geun Soo Lee. Protective effects of fermented Citrus unshiu peel extract against ultraviolet-A-induced photoageing in human dermal fibrobolasts. Phytotherapy research : PTR. 2012 Dec; 26(12):1851-6. doi: 10.1002/ptr.4670. [PMID: 22422675]
  • Mingliang Zhong, Guibo Sun, Xiaopo Zhang, Guangli Sun, Xudong Xu, Shichun Yu. A new prenylated naphthoquinoid from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. Molecules (Basel, Switzerland). 2012 Nov; 17(12):13910-6. doi: 10.3390/molecules171213910. [PMID: 23178306]
  • Sang Keun Ha, Ho-Young Park, Hyojin Eom, Yoonsook Kim, Inwook Choi. Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Oct; 50(10):3498-504. doi: 10.1016/j.fct.2012.07.007. [PMID: 22813871]
  • Ram M Uckoo, Guddadarangavvanahally K Jayaprakasha, V M Balasubramaniam, Bhimanagouda S Patil. Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques. Journal of food science. 2012 Sep; 77(9):C921-6. doi: 10.1111/j.1750-3841.2012.02865.x. [PMID: 22957912]
  • Wei Huang, Zhi-Hua Xiong, Xi Huang, Xiao Chen, Wei-Ping Liu, Yang Wang, Ping Ren. Simultaneous UPLC analysis of three major flavonoids in granule decoctions of Fructus aurantii-type formulae. Die Pharmazie. 2012 Jul; 67(7):586-9. doi: ". [PMID: 22888512]
  • Rong Fan, Xi Huang, Yang Wang, Xiao Chen, Ping Ren, Hui Ji, Ying Xie, Yingjin Zhang, Wei Huang, Xinjian Qiu, Zhaoqian Liu, Honghao Zhou, Lan Fan, Lichen Gao. Ethnopharmacokinetic- and activity-guided isolation of a new antidepressive compound from fructus aurantii found in the traditional chinese medicine chaihu-shugan-san: a new approach and its application. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):607584. doi: 10.1155/2012/607584. [PMID: 22454671]
  • W A J P Wijesinghe, Mahinda Senevirathne, Myung-Cheol Oh, You-Jin Jeon. Protective effect of methanol extract from citrus press cakes prepared by far-infrared radiation drying on H(2)O(2)-mediated oxidative damage in Vero cells. Nutrition research and practice. 2011 Oct; 5(5):389-95. doi: 10.4162/nrp.2011.5.5.389. [PMID: 22125675]
  • Amanda J Lloyd, Manfred Beckmann, Gaëlle Favé, John C Mathers, John Draper. Proline betaine and its biotransformation products in fasting urine samples are potential biomarkers of habitual citrus fruit consumption. The British journal of nutrition. 2011 Sep; 106(6):812-24. doi: 10.1017/s0007114511001164. [PMID: 21736852]
  • Antonio Cano, Almudena Bermejo. Influence of rootstock and cultivar on bioactive compounds in citrus peels. Journal of the science of food and agriculture. 2011 Jul; 91(9):1702-11. doi: 10.1002/jsfa.4375. [PMID: 21656771]
  • Nanako Sato, Chika Seiwa, Michihiro Uruse, Masahiro Yamamoto, Kayoko Tanaka, Takuya Kawakita, Yasuhiro Komatsu, Akio Yasukawa, Masakatsu Takao, Chiaki Kudo, Atsuhiko Hasegawa, Atushi Ishige, Kenji Watanabe, Hiroaki Asou. Administration of chinpi, a component of the herbal medicine ninjin-youei-to, reverses age-induced demyelination. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):617438. doi: 10.1093/ecam/neq001. [PMID: 21799684]
  • Deena Ramful, Theeshan Bahorun, Emmanuel Bourdon, Evelyne Tarnus, Okezie I Aruoma. Bioactive phenolics and antioxidant propensity of flavedo extracts of Mauritian citrus fruits: potential prophylactic ingredients for functional foods application. Toxicology. 2010 Nov; 278(1):75-87. doi: 10.1016/j.tox.2010.01.012. [PMID: 20100535]
  • R Estrada-Reyes, M Martínez-Vázquez, A Gallegos-Solís, G Heinze, J Moreno. Depressant effects of Clinopodium mexicanum Benth. Govaerts (Lamiaceae) on the central nervous system. Journal of ethnopharmacology. 2010 Jul; 130(1):1-8. doi: 10.1016/j.jep.2010.03.012. [PMID: 20362043]
  • M Viuda-Martos, Y Ruiz-Navajas, J Fernández-López, J A Pérez-Alvarez. Effect of added citrus fibre and spice essential oils on quality characteristics and shelf-life of mortadella. Meat science. 2010 Jul; 85(3):568-76. doi: 10.1016/j.meatsci.2010.03.007. [PMID: 20416839]
  • Lea Bredsdorff, Inge Lise F Nielsen, Salka E Rasmussen, Claus Cornett, Denis Barron, Florilene Bouisset, Elizabeth Offord, Gary Williamson. Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from alpha-rhamnosidase-treated orange juice in human subjects. The British journal of nutrition. 2010 Jun; 103(11):1602-9. doi: 10.1017/s0007114509993679. [PMID: 20100371]
  • Chen Wang, Yaju Pan, Guorong Fan, Yifeng Chai, Yutian Wu. Application of an efficient strategy based on MAE, HPLC-DAD-MS/MS and HSCCC for the rapid extraction, identification, separation and purification of flavonoids from Fructus Aurantii Immaturus. Biomedical chromatography : BMC. 2010 Mar; 24(3):235-44. doi: 10.1002/bmc.1278. [PMID: 19591241]
  • Elizabeth Joubert, Wentzel C A Gelderblom, Dalene De Beer. Phenolic contribution of South African herbal teas to a healthy diet. Natural product communications. 2009 May; 4(5):701-18. doi: . [PMID: 19445319]
  • Samiuela Lee, Cheang S Khoo, Jarryd L Pearson, James R Hennell, Alan Bensoussan. Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract. Journal of AOAC International. 2009 May; 92(3):789-96. doi: . [PMID: 19610369]
  • Gary M Brett, Wendy Hollands, Paul W Needs, Birgit Teucher, Jack R Dainty, Barry D Davis, Jennifer S Brodbelt, Paul A Kroon. Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion. The British journal of nutrition. 2009 Mar; 101(5):664-75. doi: 10.1017/s000711450803081x. [PMID: 18710603]
  • Yoshiko Fukuchi, Masanori Hiramitsu, Miki Okada, Sanae Hayashi, Yuka Nabeno, Toshihiko Osawa, Michitaka Naito. Lemon Polyphenols Suppress Diet-induced Obesity by Up-Regulation of mRNA Levels of the Enzymes Involved in beta-Oxidation in Mouse White Adipose Tissue. Journal of clinical biochemistry and nutrition. 2008 Nov; 43(3):201-9. doi: 10.3164/jcbn.2008066. [PMID: 19015756]
  • Tadashi Fujita, Atsushi Kawase, Toshiro Niwa, Norimichi Tomohiro, Megumi Masuda, Hideaki Matsuda, Masahiro Iwaki. Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities. Biological & pharmaceutical bulletin. 2008 May; 31(5):925-30. doi: 10.1248/bpb.31.925. [PMID: 18451520]
  • G H Xu, J C Chen, D H Liu, Y H Zhang, P Jiang, X Q Ye. Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water. Journal of food science. 2008 Jan; 73(1):C11-8. doi: 10.1111/j.1750-3841.2007.00546.x. [PMID: 18211343]
  • Claudio Gardana, Serena Guarnieri, Patrizia Riso, Paolo Simonetti, Marisa Porrini. Flavanone plasma pharmacokinetics from blood orange juice in human subjects. The British journal of nutrition. 2007 Jul; 98(1):165-72. doi: 10.1017/s0007114507699358. [PMID: 17367568]
  • Da-Yong Zhou, Qing Xu, Xin-Ya Xue, Fei-Fang Zhang, Xin-Miao Liang. Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2006 Oct; 42(4):441-8. doi: 10.1016/j.jpba.2006.05.015. [PMID: 16837161]
  • Hai-Jiang Zhang, Yi-Yu Cheng. An HPLC/MS method for identifying major constituents in the hypocholesterolemic extracts of Chinese medicine formula 'Xue-Fu-Zhu-Yu decoction'. Biomedical chromatography : BMC. 2006 Aug; 20(8):821-6. doi: 10.1002/bmc.607. [PMID: 16345012]
  • Zbigniew Sroka, Izabela Fecka, Wojciech Cisowski. Antiradical and anti-H2O2 properties of polyphenolic compounds from an aqueous peppermint extract. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 Nov; 60(11-12):826-32. doi: 10.1515/znc-2005-11-1203. [PMID: 16402541]
  • Minchinori Kubo, Hideaki Matsuda, Norimichi Tomohiro, Shouichi Harima. [Historical and pharmalogical study of Citrus hassaku.]. Yakushigaku zasshi. 2005; 40(1):47-51. doi: . [PMID: 16217907]
  • Junmei Zhang, Jennifer S Brodbelt. Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. The Analyst. 2004 Dec; 129(12):1227-33. doi: 10.1039/b412577k. [PMID: 15565223]
  • B Irene Kamara, D Jacobus Brand, E Vincent Brandt, Elizabeth Joubert. Phenolic metabolites from honeybush tea (Cyclopia subternata). Journal of agricultural and food chemistry. 2004 Aug; 52(17):5391-5. doi: 10.1021/jf040097z. [PMID: 15315375]
  • Federica Pellati, Stefania Benvenuti, Michele Melegari. High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara. Phytochemical analysis : PCA. 2004 Jul; 15(4):220-5. doi: 10.1002/pca.771. [PMID: 15311840]
  • Michinori Kubo, Hideaki Matsuda, Norimichi Tomohiro, Shouichi Harima. [History and therapeutic evaluation of Citrus hassaku HORT. Tanaka]. Yakushigaku zasshi. 2004; 39(2):363-4. doi: . [PMID: 16025659]
  • C Manach, C Morand, A Gil-Izquierdo, C Bouteloup-Demange, C Rémésy. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. European journal of clinical nutrition. 2003 Feb; 57(2):235-42. doi: 10.1038/sj.ejcn.1601547. [PMID: 12571654]
  • Mingfu Wang, James E Simon, Irma Fabiola Aviles, Kan He, Qun-Yi Zheng, Yaakov Tadmor. Analysis of antioxidative phenolic compounds in artichoke (Cynara scolymus L.). Journal of agricultural and food chemistry. 2003 Jan; 51(3):601-8. doi: 10.1021/jf020792b. [PMID: 12537429]
  • H K Kim, W K Jeon, B S Ko. Flavanone glycosides from Citrus junos and their anti-influenza virus activity. Planta medica. 2001 Aug; 67(6):548-9. doi: 10.1055/s-2001-16484. [PMID: 11509977]
  • . . . . doi: . [PMID: 15053528]