Afzelin (BioDeep_00000269914)

 

Secondary id: BioDeep_00000000545, BioDeep_00000175775, BioDeep_00000229226

natural product PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin


代谢物信息卡片


5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

化学式: C21H20O10 (432.105642)
中文名称: 阿福豆甙, 阿福豆苷, 阿福豆苷, 山柰素-3-O-鼠李糖苷
谱图信息: 最多检出来源 Viridiplantae(plant) 2.57%

分子结构信息

SMILES: C(C(=O)3)(=C(Oc(c4)c3c(cc(O)4)O)c(c2)ccc(O)c2)OC(O1)C(O)C(O)C(O)C(C)1
InChI: InChI=1/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1

描述信息

Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-).
Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available.
A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].
Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4].
Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

同义名列表

53 个代谢物同义名

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one; 4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-; 4H-1-Benzopyran-4-one, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; 5,7-Dihydroxy-2-(4-Hydroxyphenyl)-4-Oxo-4h-Chromen-3-Yl 6-Deoxy-Alpha-L-Mannopyranoside; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl alpha-L-rhamnoside; KAEMPFEROL 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE; KAEMPHEROL 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE; afzelin; kaempherol 3-O-alpha-rhamnoside; KAEMPFEROL 3-(6-DEOXY-L-MANNOPYRANOSIDE); 3-O-.ALPHA.-L-RHAMNOPYRANOSYLKAEMPFEROL; kaempferol 3-O-alpha-L-rhamnopyranoside; KAEMPFEROL 3-.ALPHA.-L-RHAMNOPYRANOSIDE; kaempferol-3-o-alpha-l-rhamnopyranoside; KAEMPFEROL 3-O-.ALPHA.-L-RHAMNOSIDE; kaempferol-3-O-alpha-L-rhamnoside; KAEMPHEROL 3-O-.ALPHA.-RHAMNOSIDE; Kaempferol 3-O-alpha-L-rhamnoside; KAEMPFEROL 3-O-RHAMNOPYRANOSIDE; KAEMPFEROL-3-.ALPHA.-L-RHAMNOSE; kaempherol 3-O-alpha-rhamnoside; kaempferol-3-o-beta-rhamnoside; KAEMPFEROL 3-O-GLUCORHAMNOSIDE; KAEMPFEROL RHAMNOSIDE [INCI]; Afzelin, >=90\\% (LC/MS-UV); KAEMPFEROL 3-L-RHAMNOSIDE; KAEMPFEROL-3-O-RHAMNOSIDE; kaempferol 3-O-rhamnoside; Kaempferol 3-rhamnoside; kaempferol-3-rhamnoside; Kaempferol rhamnoside; UNII-5M86W1YH7O; MEGxp0_000339; ACon1_000149; 5M86W1YH7O; Kaempferin; Afzeloside; Afzelin; AFE; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-tetrahydropyranyl]oxy]-4-chromenone; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromone; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chromen-4-one; 3,4,5,7-Tetrahydroxyflavone-3-L-rhamnoside; AIDS-088684; AIDS088684; 482-39-3; Kaempferol-3-O-rhamnose; 3- [ (6-Deoxy-alpha-L-mannopyranosyl) oxy ] -5,7-dihydroxy-2- (4-hydroxyphenyl) -4H-1-benzopyran-4-one; Kaempferol 3-O-alpha-rhamnoside



数据库引用编号

69 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)

523 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

  • Lei Xia, Xiaoqing Xu, Meijun Li, Xinyue Zhang, Fang Cao. Afzelin induces immunogenic cell death against lung cancer by targeting NQO2. BMC complementary medicine and therapies. 2023 Oct; 23(1):381. doi: 10.1186/s12906-023-04221-3. [PMID: 37891619]
  • Masuma Akter, Mst Shahnaj Parvin, Md Mahadi Hasan, Md Aziz Abdur Rahman, Md Ekramul Islam. Anti-tumor and antioxidant activity of kaempferol-3-O-alpha-L-rhamnoside (Afzelin) isolated from Pithecellobium dulce leaves. BMC complementary medicine and therapies. 2022 Jun; 22(1):169. doi: 10.1186/s12906-022-03633-x. [PMID: 35733130]
  • Dahae Lee, Ji-Young Kim, Yutong Qi, Sangsu Park, Hye Lim Lee, Noriko Yamabe, Hocheol Kim, Dae Sik Jang, Ki Sung Kang. Phytochemicals from the flowers of Prunus persica (L.) Batsch: Anti-adipogenic effect of mandelamide on 3T3-L1 preadipocytes. Bioorganic & medicinal chemistry letters. 2021 10; 49(?):128326. doi: 10.1016/j.bmcl.2021.128326. [PMID: 34403725]
  • Saulo Duarte Ozelin, Juliana Marques Senedese, Jacqueline Morais Alves, Carla Carolina Munari, Juliana De Carvalho Da Costa, Flávia Aparecida Resende, Débora Leite Campos, Ildercílio Mota De Souza Lima, Augusto Faria Andrade, Eliana Aparecida Varanda, Jairo Kenupp Bastos, Denise Crispim Tavares. Preventive activity of Copaifera langsdorffii Desf. leaves extract and its major compounds, afzelin and quercitrin, on DNA damage in in vitro and in vivo models. Journal of toxicology and environmental health. Part A. 2021 07; 84(14):569-581. doi: 10.1080/15287394.2021.1898505. [PMID: 33730993]
  • So-Young Oh, Min Jun Jang, Yun-Hyeok Choi, Hongik Hwang, Hyewhon Rhim, Bonggi Lee, Chun Whan Choi, Min Soo Kim. Central administration of afzelin extracted from Ribes fasciculatum improves cognitive and memory function in a mouse model of dementia. Scientific reports. 2021 04; 11(1):9182. doi: 10.1038/s41598-021-88463-6. [PMID: 33911138]
  • Dong Gu Lee, Ju Sung Lee, Norman G Quilantang, Sonia D Jacinto, Sanghyun Lee. Determination of Afzelin and Astragalin from Lespedeza cuneata on Aldose Reductase Inhibition. Journal of chromatographic science. 2021 Mar; 59(4):381-387. doi: 10.1093/chromsci/bmaa127. [PMID: 33420504]
  • Jennyfer Andrea Aldana, Rone Aparecido De Grandis, Heloiza Nicolella, Ana Paula Prado Guissoni, Iara Squarisi, Caroline Arruda, Victor Pena Ribeiro, Denise Crispim Tavares, Gustavo Rafael Mazzaron Barcelos, Lusânia Maria Greggi Antunes, Jairo Kenupp Bastos. Evaluation of cytoprotective effects of compounds isolated from Copaifera langsdorffii Desf. against induced cytotoxicity by exposure to methylmercury and lead. Natural product research. 2020 Sep; 34(17):2528-2532. doi: 10.1080/14786419.2018.1543673. [PMID: 30623721]
  • Lin Zheng, Yueting Li, Zuying Zhou, Wenying Xiang, Zipeng Gong, Siying Chen, Yonglin Wang, Aimin Wang, Yanyu Lan, Yongjun Li, Yong Huang. Comparative pharmacokinetics of quercitrin, astragalin, afzelin and taxifolin in plasma after oral administration of Polygonum orientale inflorescence in sham-operated and myocardial ischemia-reperfusion injury rats. Xenobiotica; the fate of foreign compounds in biological systems. 2020 Jul; 50(7):822-830. doi: 10.1080/00498254.2019.1700319. [PMID: 31791186]
  • Camile Cecconi Cechinel-Zanchett, Luísa Nathália Bolda Mariano, Thaise Boeing, Juliana de Carvalho da Costa, Luísa Mota Da Silva, Jairo K Bastos, Valdir Cechinel-Filho, Priscila de Souza. Diuretic and Renal Protective Effect of Kaempferol 3-O-Alpha-l-rhamnoside (Afzelin) in Normotensive and Hypertensive Rats. Journal of natural products. 2020 06; 83(6):1980-1989. doi: 10.1021/acs.jnatprod.0c00274. [PMID: 32453565]
  • Yang Liu, Pei Chen, Mingming Zhou, Tongli Wang, Shengzuo Fang, Xulan Shang, Xiangxiang Fu. Geographic Variation in the Chemical Composition and Antioxidant Properties of Phenolic Compounds from Cyclocarya paliurus (Batal) Iljinskaja Leaves. Molecules (Basel, Switzerland). 2018 Sep; 23(10):. doi: 10.3390/molecules23102440. [PMID: 30249997]
  • Zhaochen Wu, Wei Wang, Fengyuan He, Dengwu Li, Dongmei Wang. Simultaneous Enrichment and Separation of Four Flavonoids from Zanthoxylum bungeanum Leaves by Ultrasound-Assisted Extraction and Macroporous Resins with Evaluation of Antioxidant Activities. Journal of food science. 2018 Aug; 83(8):2109-2118. doi: 10.1111/1750-3841.14282. [PMID: 30080245]
  • Robert Lotha, Niranjana Sri Sundaramoorthy, Bhanuvalli R Shamprasad, Saisubramanian Nagarajan, Aravind Sivasubramanian. Plant nutraceuticals (Quercetrin and Afzelin) capped silver nanoparticles exert potent antibiofilm effect against food borne pathogen Salmonella enterica serovar Typhi and curtail planktonic growth in zebrafish infection model. Microbial pathogenesis. 2018 Jul; 120(?):109-118. doi: 10.1016/j.micpath.2018.04.044. [PMID: 29715535]
  • Eunsun Jung, Jin Hee Kim, Mi Ok Kim, Sang Yeol Lee, Jongsung Lee. Melanocyte-protective effect of afzelin is mediated by the Nrf2-ARE signalling pathway via GSK-3β inactivation. Experimental dermatology. 2017 09; 26(9):764-770. doi: 10.1111/exd.13277. [PMID: 27992083]
  • Pham Thi Nhat Trinh, Ngoc Quoc Luan, Mai Dinh Tri, Vu Duy Khanh, Nguyen Huu An, Phan Nhat Minh, Pham Ngoc An, Nguyen Thi Le Thuy, Nguyen Kim Phi Phung, Le Tien Dung. New naphthalene derivative from the leaves of Cassia grandis L. Natural product research. 2017 Aug; 31(15):1733-1738. doi: 10.1080/14786419.2017.1290615. [PMID: 28278658]
  • Antonietta Cerulli, Gianluigi Lauro, Milena Masullo, Vincenza Cantone, Beata Olas, Bogdan Kontek, Filomena Nazzaro, Giuseppe Bifulco, Sonia Piacente. Cyclic Diarylheptanoids from Corylus avellana Green Leafy Covers: Determination of Their Absolute Configurations and Evaluation of Their Antioxidant and Antimicrobial Activities. Journal of natural products. 2017 06; 80(6):1703-1713. doi: 10.1021/acs.jnatprod.6b00703. [PMID: 28520428]
  • Myrto Maria Fouseki, Harilaos Damianakos, George Albert Karikas, Christos Roussakis, Mahabir P Gupta, Ioanna Chinou. Chemical constituents from Cordia alliodora and C. colloccoca (Boraginaceae) and their biological activities. Fitoterapia. 2016 Dec; 115(?):9-14. doi: 10.1016/j.fitote.2016.09.004. [PMID: 27659390]
  • Fengyuan He, Dengwu Li, Dongmei Wang, Ming Deng. Extraction and Purification of Quercitrin, Hyperoside, Rutin, and Afzelin from Zanthoxylum Bungeanum Maxim Leaves Using an Aqueous Two-Phase System. Journal of food science. 2016 Jul; 81(7):C1593-602. doi: 10.1111/1750-3841.13331. [PMID: 27240023]
  • Mariel de Barros, Luisa Mota da Silva, Thaise Boeing, Lincon Bordignon Somensi, Benhur Judah Cury, Ligia de Moura Burci, José Roberto Santin, Sérgio Faloni de Andrade, Franco Delle Monache, Valdir Cechinel-Filho. Pharmacological reports about gastroprotective effects of methanolic extract from leaves of Solidago chilensis (Brazilian arnica) and its components quercitrin and afzelin in rodents. Naunyn-Schmiedeberg's archives of pharmacology. 2016 Apr; 389(4):403-17. doi: 10.1007/s00210-015-1208-0. [PMID: 26758066]
  • Jun Yi, Jian-Guo Wu, Jin-Yu Wu, Yan-Bin Wu. Quality evaluation of the leaves of Magnolia officinalis var. biloba using high-performance liquid chromatography fingerprint analysis of phenolic compounds. Journal of separation science. 2016 Feb; 39(4):784-92. doi: 10.1002/jssc.201500972. [PMID: 26681396]
  • Ju Hee Lee, Jongmin Ahn, Jin Woong Kim, Sang Gook Lee, Hyun Pyo Kim. Flavonoids from the aerial parts of Houttuynia cordata attenuate lung inflammation in mice. Archives of pharmacal research. 2015 Jul; 38(7):1304-11. doi: 10.1007/s12272-015-0585-8. [PMID: 25743630]
  • Le Duc Dat, Nguyen Phuong Thao, Bui Huu Tai, Bui Thi Thuy Luyen, Sohyun Kim, Jung Eun Koo, Young Sang Koh, Nguyen The Cuong, Nguyen Van Thanh, Nguyen Xuan Cuong, Nguyen Hoai Nam, Phan Van Kiem, Chau Van Minh, Young Ho Kim. Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs). Bioorganic & medicinal chemistry letters. 2015 Apr; 25(7):1412-6. doi: 10.1016/j.bmcl.2015.02.048. [PMID: 25769817]
  • Ricardo Andrade Furtado, Cristiane Teixeira Vilhena Bernardes, Mauro Nogueira da Silva, Karina Furlani Zoccal, Lúcia Helena Faccioli, Jairo Kenupp Bastos. Antiedematogenic Evaluation of Copaifera langsdorffii Leaves Hydroethanolic Extract and Its Major Compounds. BioMed research international. 2015; 2015(?):913152. doi: 10.1155/2015/913152. [PMID: 26078969]
  • Akinori Kakumu, Masayuki Ninomiya, Mai Efdi, Morina Adfa, Masahiro Hayashi, Kaori Tanaka, Mamoru Koketsu. Phytochemical analysis and antileukemic activity of polyphenolic constituents of Toona sinensis. Bioorganic & medicinal chemistry letters. 2014 Sep; 24(17):4286-90. doi: 10.1016/j.bmcl.2014.07.022. [PMID: 25074815]
  • Sang Yeol Lee, Young-Jin So, Moon Sam Shin, Jae Youl Cho, Jongsung Lee. Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. Molecules (Basel, Switzerland). 2014 Mar; 19(3):3173-80. doi: 10.3390/molecules19033173. [PMID: 24642906]
  • Jacqueline Morais Alves, Carla Carolina Munari, Moacir de Azevedo Bentes Monteiro Neto, Ricardo Andrade Furtado, Juliana Marques Senedese, Jairo Kenupp Bastos, Denise Crispim Tavares. In vivo protective effect of Copaifera langsdorffii hydroalcoholic extract on micronuclei induction by doxorubicin. Journal of applied toxicology : JAT. 2013 Aug; 33(8):854-60. doi: 10.1002/jat.2777. [PMID: 22611044]
  • Chung-Oui Hong, Hyun Ah Lee, Chae Hong Rhee, Se-Young Choung, Kwang-Won Lee. Separation of the antioxidant compound quercitrin from Lindera obtusiloba Blume and its antimelanogenic effect on B16F10 melanoma cells. Bioscience, biotechnology, and biochemistry. 2013; 77(1):58-64. doi: 10.1271/bbb.120562. [PMID: 23291772]
  • Seoung Woo Shin, Eunsun Jung, Seungbeom Kim, Jang-Hyun Kim, Eui-Gyun Kim, Jongsung Lee, Deokhoon Park. Antagonizing effects and mechanisms of afzelin against UVB-induced cell damage. PloS one. 2013; 8(4):e61971. doi: 10.1371/journal.pone.0061971. [PMID: 23626759]
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