(-)-Epiafzelechin (BioDeep_00000395882)

Secondary id: BioDeep_00000014693, BioDeep_00000600390, BioDeep_00000865197

human metabolite PANOMIX_OTCML-2023 Endogenous

代谢物信息卡片

2H-1-benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-

化学式: C15H14O5 (274.0841194)
中文名称: 表阿夫儿茶精, (-)-表阿夫儿茶精
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.07%

分子结构信息

SMILES: C1(O)C=C2O[C@H](C3C=CC(O)=CC=3)[C@H](O)CC2=C(O)C=1
InChI: InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

描述信息

(-)-epiafzelechin is a catechin derivative having (2R,3R)-configuration. It has a role as a plant metabolite.
(-)-Epiafzelechin is a natural product found in Bauhinia racemosa, Larix gmelinii, and other organisms with data available.
(-)-Epiafzelechin is found in fruits. (-)-Epiafzelechin is a constituent of Actinidia chinensis (kiwi fruit) and Juniperus communis (juniper)
Constituent of Actinidia chinensis (kiwi fruit) and Juniperus communis (juniper). (-)-Epiafzelechin is found in kiwi, tea, and fruits.
A catechin derivative having (2R,3R)-configuration.

同义名列表

18 个代谢物同义名

2H-1-benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-; (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol; (-)-epi-Afzelechin;Epiafzelechin, (-)-; epi-Afzelechin; (2R,3R)-2-(4-Hydroxy-phenyl)-chroman-3,5,7-triol; (2R,3R)-2-(4-hydroxyphenyl)chromane-3,5,7-triol; (2R,3R)-2-(4-Hydroxyphenyl)-3,5,7-chromantriol; 2-(4-hydroxyphenyl)chromane-3,5,7-triol; EPIAFZELECHIN (2R,3R)(-); (2R,3R)-epiafzelechin; 2,3-cis-epiafzelechin; (-)-Epiafzelechin; Spectrum3_001685; Spectrum2_001755; epi-Afzelechin; epiafzelechin; KBio3_002430; afzelechin

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:31028
KEGG: C12128
PubChem: 443639
HMDB: HMDB0030822
ChEMBL: CHEMBL159303
LipidMAPS: LMPK12020036
MeSH: afzelechin
MetaCyc: CPD-10413
KNApSAcK: C00008805
foodb: FDB002778
chemspider: 391781
CAS: 24808-04-6
medchemexpress: HY-N0943
MetaboLights: MTBLC31028
PubChem: 14275
3DMET: B04427
NIKKAJI: J18.806I

分类词条

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)

51 个相关的物种来源信息

93694 Tsuga chinensis: 10.1002/JCCS.198500075
2058695 Pinalia floribunda:
3922 Wisteria floribunda:
948717 Cassia roxburghii: 10.1515/ZNB-1984-1020
99658 Xanthoceras sorbifolium: 10.1021/NP9902441
1987958 Aiouea hammeliana: 10.1007/978-1-4899-1783-6_3
4442 Camellia sinensis:
382341 Artocarpus lacucha: 10.1021/NP010451C
709041 Artocarpus dadah: 10.1021/NP010451C
653097 Phanera vahlii: 10.1016/J.EJMECH.2012.01.057
1227988 Bauhinia racemosa: 10.1016/J.EJMECH.2012.01.057
3625 Actinidia chinensis: 10.1055/S-2005-871225
309266 Ficus cordata: 10.1016/J.JEP.2008.07.026
85181 Celastrus orbiculatus:
994668 Celastrus paniculatus: 10.1021/NP000251L
379307 Typha capensis:
202634 Crateva religiosa: 10.1016/S0031-9422(00)80571-3
2745869 Madhuca pasquieri: 10.1515/ZNC-1997-5-603
53852 Cassia fistula:
296036 Phyllanthus emblica: 10.1021/NP010370G
508996 Cassia javanica: 10.1248/CPB.38.888
397678 Dicranopteris pedata: 10.1248/CPB.38.856
326968 Ziziphus jujuba: 10.1007/BF02291535
123599 Larix gmelinii: 10.1016/S0031-9422(00)84524-0
1977551 Cassia sieberiana: 10.1021/NP100090E
93694 Tsuga chinensis: 10.1002/JCCS.198500075
2058695 Pinalia floribunda:
3922 Wisteria floribunda:
948717 Cassia roxburghii: 10.1515/ZNB-1984-1020
99658 Xanthoceras sorbifolium: 10.1021/NP9902441
1987958 Aiouea hammeliana: 10.1007/978-1-4899-1783-6_3
4442 Camellia sinensis:
382341 Artocarpus lacucha: 10.1021/NP010451C
709041 Artocarpus dadah: 10.1021/NP010451C
653097 Phanera vahlii: 10.1016/J.EJMECH.2012.01.057
1227988 Bauhinia racemosa: 10.1016/J.EJMECH.2012.01.057
3625 Actinidia chinensis: 10.1055/S-2005-871225
309266 Ficus cordata: 10.1016/J.JEP.2008.07.026
85181 Celastrus orbiculatus:
994668 Celastrus paniculatus: 10.1021/NP000251L
379307 Typha capensis:
202634 Crateva religiosa: 10.1016/S0031-9422(00)80571-3
2745869 Madhuca pasquieri: 10.1515/ZNC-1997-5-603
53852 Cassia fistula:
296036 Phyllanthus emblica: 10.1021/NP010370G
508996 Cassia javanica: 10.1248/CPB.38.888
397678 Dicranopteris pedata: 10.1248/CPB.38.856
326968 Ziziphus jujuba: 10.1007/BF02291535
123599 Larix gmelinii: 10.1016/S0031-9422(00)84524-0
1977551 Cassia sieberiana: 10.1021/NP100090E
9606 Homo sapiens: -

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

Sara Zahid, Arif Malik, Suleyman Waqar, Fatima Zahid, Nusrat Tariq, Ali Imran Khawaja, Waqas Safir, Faisal Gulzar, Javeid Iqbal, Qurban Ali. Countenance and implication of Β-sitosterol, Β-amyrin and epiafzelechin in nickel exposed Rat: in-silico and in-vivo approach. Scientific reports. 2023 12; 13(1):21351. doi: 10.1038/s41598-023-48772-4. [PMID: 38049552]
Yue Zheng, Xian-Wen Yang, Dominique Schols, Mattia Mori, Bruno Botta, Andy Chevigné, Martin Mulinge, André Steinmetz, Jean-Claude Schmit, Carole Seguin-Devaux. Active Components from Cassia abbreviata Prevent HIV-1 Entry by Distinct Mechanisms of Action. International journal of molecular sciences. 2021 May; 22(9):. doi: 10.3390/ijms22095052. [PMID: 34068829]
Michał Gleńsk, Marta K Dudek, Maciej Ciach, Maciej Włodarczyk. Isolation and structural determination of flavan-3-ol derivatives from the Polypodium vulgare L. rhizomes water extract. Natural product research. 2021 May; 35(9):1474-1483. doi: 10.1080/14786419.2019.1655302. [PMID: 31538499]
Xia Wu, Ying Liu, Jieqing Guo, Juanxia Wang, Meizhen Li, Youzhen Tan, Qifan Zheng, Yifan Feng. Differentiating Pu-erh raw tea from different geographical origins by 1 H-NMR and U-HPLC/Q-TOF-MS combined with chemometrics. Journal of food science. 2021 Mar; 86(3):779-791. doi: 10.1111/1750-3841.15624. [PMID: 33598925]
Yang Zeng, Yu-Xia Sun, Xiu-Hua Meng, Tao Yu, Hong-Tao Zhu, Ying-Jun Zhang. A new methylene bisflavan-3-ol from the branches and leaves of Potentilla fruticosa. Natural product research. 2020 May; 34(9):1238-1245. doi: 10.1080/14786419.2018.1557169. [PMID: 30663382]
Xuemei Guo, Piaopiao Long, Qilu Meng, Chi-Tang Ho, Liang Zhang. An emerging strategy for evaluating the grades of Keemun black tea by combinatory liquid chromatography-Orbitrap mass spectrometry-based untargeted metabolomics and inhibition effects on α-glucosidase and α-amylase. Food chemistry. 2018 Apr; 246(?):74-81. doi: 10.1016/j.foodchem.2017.10.148. [PMID: 29291881]
Kengo Hori, Mikiyo Wada, Shoji Yahara, Takashi Watanabe, Hari Prasad Devkota. Antioxidant phenolic compounds from the rhizomes of Astilbe rivularis. Natural product research. 2018 Feb; 32(4):453-456. doi: 10.1080/14786419.2017.1309536. [PMID: 28361551]
Ka-Chun Wong, Sisi Cao, Xiaoli Dong, Man-Chun Law, Tak-Hang Chan, Man-Sau Wong. (-)-Epiafzelechin Protects against Ovariectomy-induced Bone Loss in Adult Mice and Modulate Osteoblastic and Osteoclastic Functions In Vitro. Nutrients. 2017 May; 9(5):. doi: 10.3390/nu9050530. [PMID: 28531166]
Rui Fang, Sally P Redfern, Don Kirkup, Elaine A Porter, Geoffrey C Kite, Leon A Terry, Mark J Berry, Monique S J Simmonds. Variation of theanine, phenolic, and methylxanthine compounds in 21 cultivars of Camellia sinensis harvested in different seasons. Food chemistry. 2017 Apr; 220(?):517-526. doi: 10.1016/j.foodchem.2016.09.047. [PMID: 27855934]
J Andrew Jones, Shannon M Collins, Victoria R Vernacchio, Daniel M Lachance, Mattheos A G Koffas. Optimization of naringenin and p-coumaric acid hydroxylation using the native E. coli hydroxylase complex, HpaBC. Biotechnology progress. 2016 Jan; 32(1):21-5. doi: 10.1002/btpr.2185. [PMID: 26488898]
Biljana Kiprovski, Maja Mikulic-Petkovsek, Ana Slatnar, Robert Veberic, Franci Stampar, Djordje Malencic, Dragana Latkovic. Comparison of phenolic profiles and antioxidant properties of European Fagopyrum esculentum cultivars. Food chemistry. 2015 Oct; 185(?):41-7. doi: 10.1016/j.foodchem.2015.03.137. [PMID: 25952839]
Ka Chun Wong, Man Chun Law, Man Sau Wong, Tak Hang Chan. Development of a UPLC-MS/MS bioanalytical method for the pharmacokinetic study of (-)-epiafzelechin, a flavan-3-ol with osteoprotective activity, in C57BL/6J mice. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Sep; 967(?):162-7. doi: 10.1016/j.jchromb.2014.07.028. [PMID: 25108364]
María Luisa Mateos-Martín, Elisabet Fuguet, Allan Jiménez-Ardón, Libia Herrero-Uribe, Giselle Tamayo-Castillo, Josep Lluís Torres. Identification of polyphenols from antiviral Chamaecrista nictitans extract using high-resolution LC-ESI-MS/MS. Analytical and bioanalytical chemistry. 2014 Sep; 406(22):5501-6. doi: 10.1007/s00216-014-7982-6. [PMID: 24969467]
Xiaobin Zeng, Jun Tian, Kangyong Cai, Xin Wu, Yang Wang, Yayuan Zheng, Yanjie Su, Liao Cui. Promoting osteoblast differentiation by the flavanes from Huangshan Maofeng tea is linked to a reduction of oxidative stress. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Feb; 21(3):217-24. doi: 10.1016/j.phymed.2013.08.026. [PMID: 24075209]
Mohamed A Farag, Mohamed S Abdelfattah, Sherif E A Badr, Ludger A Wessjohann. Profiling the chemical content of Ficus lyrata extracts via UPLC-PDA-qTOF-MS and chemometrics. Natural product research. 2014; 28(19):1549-56. doi: 10.1080/14786419.2014.926353. [PMID: 24934244]
Ik-Soo Lee, Song Yi Yu, Seung-Hyun Jung, Yu-Ri Lee, Yun Mi Lee, Joo-Hwan Kim, Hang Sun, Jin Sook Kim. Proanthocyanidins from Spenceria ramalana and their effects on AGE formation in vitro and hyaloid-retinal vessel dilation in larval zebrafish in vivo. Journal of natural products. 2013 Oct; 76(10):1881-8. doi: 10.1021/np400442b. [PMID: 24131240]
Hong-Bo Zhu, Bao-Min Li, Chao Liu, Ruo-Yun Chen. [Chemical constituents of Camellia sinensis var. assamica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 May; 38(9):1386-9. doi: . [PMID: 23944074]
K Koga, M Hisamura, T Kanetaka, K Yoshino, Y Matsuo, T Tanaka. Proanthocyanidin oligomers isolated from Salacia reticulata leaves potently inhibit pancreatic lipase activity. Journal of food science. 2013 Jan; 78(1):H105-11. doi: 10.1111/1750-3841.12001. [PMID: 23278351]
Mingzhe Gao, Hongbin Xiao. Activity-guided isolation of antioxidant compounds from Rhizophora apiculata. Molecules (Basel, Switzerland). 2012 Sep; 17(9):10675-82. doi: 10.3390/molecules170910675. [PMID: 22955456]
Koneni V Sashidhara, Suriya P Singh, Sweta Misra, Jyoti Gupta, Shailja Misra-Bhattacharya. Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi. European journal of medicinal chemistry. 2012 Apr; 50(?):230-5. doi: 10.1016/j.ejmech.2012.01.057. [PMID: 22348826]
Urmila C Kumavat, Shraddha N Shimpi, Sandesh P Jagdale. Hypoglycemic activity of Cassia javanica Linn. in normal and streptozotocin-induced diabetic rats. Journal of advanced pharmaceutical technology & research. 2012 Jan; 3(1):47-51. doi: 10.4103/2231-4040.93562. [PMID: 22470893]
Li-Yin Chen, Ih-Sheng Chen, Chien-Fang Peng. Structural elucidation and bioactivity of biflavonoids from the stems of Wikstroemia taiwanensis. International journal of molecular sciences. 2012; 13(1):1029-1038. doi: 10.3390/ijms13011029. [PMID: 22312302]
Xin Qiao, Ting Zhao, Meng Wang, Chun Lei, Aijun Hou. [Flavonoids from Artocarpus hypargyreus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Nov; 36(21):2975-9. doi: 10.4268/cjcmm20112117. [PMID: 22308687]
Kafui Kpegba, Amegnona Agbonon, Ana G Petrovic, Etchri Amouzou, Messanvi Gbeassor, Gloria Proni, Nasri Nesnas. Epiafzelechin from the root bark of Cassia sieberiana: detection by DART mass spectrometry, spectroscopic characterization, and antioxidant properties. Journal of natural products. 2011 Mar; 74(3):455-9. doi: 10.1021/np100090e. [PMID: 21070009]
Xingcui Li, Hongqing Wang, Chao Liu, Ruoyun Chen. [Chemical constituents of Acacia catechu]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jun; 35(11):1425-7. doi: . [PMID: 20822013]
Huaming Tao, Lishu Wang, Zhanchen Cui, Daqing Zhao, Yonghong Liu. Dimeric proanthocyanidins from the roots of Ephedra sinica. Planta medica. 2008 Dec; 74(15):1823-5. doi: 10.1055/s-0028-1088321. [PMID: 18975262]
V Kuete, B Ngameni, C C Fotso Simo, R Kengap Tankeu, B Tchaleu Ngadjui, J J M Meyer, N Lall, J R Kuiate. Antimicrobial activity of the crude extracts and compounds from Ficus chlamydocarpa and Ficus cordata (Moraceae). Journal of ethnopharmacology. 2008 Oct; 120(1):17-24. doi: 10.1016/j.jep.2008.07.026. [PMID: 18718518]
Lauro M de Souza, Thales R Cipriani, Marcello Iacomini, Philip A J Gorin, Guilherme L Sassaki. HPLC/ESI-MS and NMR analysis of flavonoids and tannins in bioactive extract from leaves of Maytenus ilicifolia. Journal of pharmaceutical and biomedical analysis. 2008 May; 47(1):59-67. doi: 10.1016/j.jpba.2007.12.008. [PMID: 18215490]
Ren-Bo An, Eun-Jeon Park, Gil-Saeng Jeong, Dong-Hwan Sohn, Youn-Chul Kim. Cytoprotective constituent of Hoveniae Lignum on both Hep G2 cells and rat primary hepatocytes. Archives of pharmacal research. 2007 Jun; 30(6):674-7. doi: 10.1007/bf02977626. [PMID: 17679542]
Gao Li, Byung-Sun Min, Changji Zheng, Joongku Lee, Sei-Ryang Oh, Kyung-Seop Ahn, Hyeong-Kyu Lee. Neuroprotective and free radical scavenging activities of phenolic compounds from Hovenia dulcis. Archives of pharmacal research. 2005 Jul; 28(7):804-9. doi: 10.1007/bf02977346. [PMID: 16114495]
Eun Ju Chang, Won Jung Lee, Sung Hee Cho, Sang Won Choi. Proliferative effects of flavan-3-ols and propelargonidins from rhizomes of Drynaria fortunei on MCF-7 and osteoblastic cells. Archives of pharmacal research. 2003 Aug; 26(8):620-30. doi: 10.1007/bf02976711. [PMID: 12967197]
Bao-Ning Su, Muriel Cuendet, Michael E Hawthorne, Leonardus B S Kardono, Soedarsono Riswan, Harry H S Fong, Rajendra G Mehta, John M Pezzuto, A Douglas Kinghorn. Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity. Journal of natural products. 2002 Feb; 65(2):163-9. doi: 10.1021/np010451c. [PMID: 11858749]
K R Min, B Y Hwang, H S Lim, B S Kang, G J Oh, J Lee, S H Kang, K S Lee, J S Ro, Y Kim. (-)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus. Planta medica. 1999 Jun; 65(5):460-2. doi: 10.1055/s-2006-960813. [PMID: 10418338]