Pelargonidin (BioDeep_00000004158)

 

Secondary id: BioDeep_00000640859

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


3,5,7-trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride

化学式: [C15H11O5]+ (271.0606456)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.04%

分子结构信息

SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O)c1ccc(cc1)O)O)O
InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1

描述信息

Pelargonidin, also known as pelargonidin chloride (CAS: 134-04-3) is an anthocyanin. Anthocyanins are water-soluble glycosides and acylglycosides of anthocyanidins, which are polyhydroxy and polymethoxyl derivatives of a 2-phenylbenzopyrylium (flavylium) cation. They are widely distributed in foods of plant origin, especially in fruits and vegetables with dark red and blue colours. Numerous epidemiologic and clinical trials show that fruits and vegetables, many of which are rich in anthocyanins, may be related to the decreased incidence of many chronic and degenerative diseases, including heart disease, cancer, and aging. Antioxidant mechanisms were suggested as potential means of disease prevention. Anthocyanins are strong antioxidants in vitro. In most cases, fruits and vegetables with high anthocyanin content were shown to have higher antioxidant capacity than other fruits and vegetables. Whether anthocyanins are effective antioxidants in vivo remains an open question primarily because of the relatively low apparent absorption of anthocyanins compared with other phenolic compounds (PMID: 15465754). BioTransformer predicts that pelargonidin is a product of 5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-3,7-dihydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by an EC.3.2.1.X enzyme (PMID: 30612223).
Anthocyanin pigment present in many plants, flowers and fruits, e.g. cherries, raspberries, radishes, orchids, brassicas, Petunia subspecies Glycosides also widely distributed. Pelargonidin is found in many foods, some of which are almond, radish (variety), garden tomato, and tarragon.

同义名列表

11 个代谢物同义名

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride; 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chloride; 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2H-chromen-2-ylium; 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium; 3,4,5,7-Tetrahydroxyflavylium chloride; Pelargonidol chloride; Pelargonidin chloride; pelargonidine; Pelarogonidin; pelargonidin; Pelargonidol



数据库引用编号

21 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(1)

代谢反应

10 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(7)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

84 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

  • Yahyea Baktiar Laskar, Kasturi Bhattacharjee, Moumita Nath, Yashmin Choudhury, Pranab Behari Mazumder, Anupam Das Talukdar. Protective Effects of Pelargonidin against DMBA-Induced Mammary Tumorigenesis in BALB/c Mice through Reduced Oxidative Stress and Lipid Anomalies. Nutrition and cancer. 2023 May; ?(?):1-21. doi: 10.1080/01635581.2023.2219027. [PMID: 37255368]
  • Qianyu Wang, Jin Zhu, Bing Li, Shanshan Li, Yong Yang, Qingyun Wang, Wenzhong Xu, Liangsheng Wang. Functional identification of anthocyanin glucosyltransferase genes: a Ps3GT catalyzes pelargonidin to pelargonidin 3-O-glucoside painting the vivid red flower color of Paeonia. Planta. 2023 Feb; 257(4):65. doi: 10.1007/s00425-023-04095-2. [PMID: 36826722]
  • Nicholas G Lamson, Katherine C Fein, John P Gleeson, Alexandra N Newby, Sijie Xian, Kyle Cochran, Namit Chaudhary, Jilian R Melamed, Rebecca L Ball, Kanika Suri, Vishal Ahuja, Anna Zhang, Adrian Berger, Dmytro Kolodieznyi, Brigitte F Schmidt, Gloria L Silva, Kathryn A Whitehead. The strawberry-derived permeation enhancer pelargonidin enables oral protein delivery. Proceedings of the National Academy of Sciences of the United States of America. 2022 08; 119(33):e2207829119. doi: 10.1073/pnas.2207829119. [PMID: 35943988]
  • Zhuo Tian, Chenkun Sun, Jun Liu. Pelargonidin inhibits vascularization and metastasis of brain gliomas by blocking the PI3K/AKT/mTOR pathway. Journal of biosciences. 2022; 47(?):. doi: . [PMID: 36226369]
  • Tsukasa Iwashina, Sri Rahayu, Kohtaro Sugahara, Takayuki Mizuno, Chie Tsutsumi, Didik Widyatmoko. Acylated pelargonidin and cyanidin 3-sambubiosides from the flowers of Aeschynanthus species and cultivars. Phytochemistry. 2021 Dec; 192(?):112956. doi: 10.1016/j.phytochem.2021.112956. [PMID: 34592514]
  • Yang Xu, Yuting Li, Jiahong Xie, Lianghua Xie, Jianling Mo, Wei Chen. Bioavailability, Absorption, and Metabolism of Pelargonidin-Based Anthocyanins Using Sprague-Dawley Rats and Caco-2 Cell Monolayers. Journal of agricultural and food chemistry. 2021 Jul; 69(28):7841-7850. doi: 10.1021/acs.jafc.1c00257. [PMID: 34139848]
  • Michele Biagioli, Silvia Marchianò, Rosalinda Roselli, Cristina Di Giorgio, Rachele Bellini, Martina Bordoni, Anna Gidari, Samuele Sabbatini, Daniela Francisci, Bianca Fiorillo, Bruno Catalanotti, Eleonora Distrutti, Adriana Carino, Angela Zampella, Gabriele Costantino, Stefano Fiorucci. Discovery of a AHR pelargonidin agonist that counter-regulates Ace2 expression and attenuates ACE2-SARS-CoV-2 interaction. Biochemical pharmacology. 2021 06; 188(?):114564. doi: 10.1016/j.bcp.2021.114564. [PMID: 33872570]
  • X Z Tian, Q Lu, P Paengkoum, S Paengkoum. Short communication: Effect of purple corn pigment on change of anthocyanin composition and unsaturated fatty acids during milk storage. Journal of dairy science. 2020 Sep; 103(9):7808-7812. doi: 10.3168/jds.2020-18409. [PMID: 32684465]
  • Maria Bellumori, Nancy A Chasquibol Silva, Laida Vilca, Luisa Andrenelli, Lorenzo Cecchi, Marzia Innocenti, Diletta Balli, Nadia Mulinacci. A Study on the Biodiversity of Pigmented Andean Potatoes: Nutritional Profile and Phenolic Composition. Molecules (Basel, Switzerland). 2020 Jul; 25(14):. doi: 10.3390/molecules25143169. [PMID: 32664446]
  • Yu-Sheng Shi, Xiao-Xing Li, Hao-Tian Li, Yan Zhang. Pelargonidin ameliorates CCl4-induced liver fibrosis by suppressing the ROS-NLRP3-IL-1β axis via activating the Nrf2 pathway. Food & function. 2020 Jun; 11(6):5156-5165. doi: 10.1039/d0fo00660b. [PMID: 32432601]
  • Ana Zuleta-Correa, Mari Sum Chinn, Marcela Alfaro-Córdoba, Van-Den Truong, George Craig Yencho, José Manuel Bruno-Bárcena. Use of unconventional mixed Acetone-Butanol-Ethanol solvents for anthocyanin extraction from Purple-Fleshed sweetpotatoes. Food chemistry. 2020 Jun; 314(?):125959. doi: 10.1016/j.foodchem.2019.125959. [PMID: 31991283]
  • Héctor A Peniche-Pavía, Axel Tiessen. Anthocyanin Profiling of Maize Grains Using DIESI-MSQD Reveals That Cyanidin-Based Derivatives Predominate in Purple Corn, whereas Pelargonidin-Based Molecules Occur in Red-Pink Varieties from Mexico. Journal of agricultural and food chemistry. 2020 May; 68(21):5980-5994. doi: 10.1021/acs.jafc.9b06336. [PMID: 32379971]
  • Laura A Chatham, Jay E Howard, John A Juvik. A natural colorant system from corn: Flavone-anthocyanin copigmentation for altered hues and improved shelf life. Food chemistry. 2020 Apr; 310(?):125734. doi: 10.1016/j.foodchem.2019.125734. [PMID: 31791725]
  • Minseok Seo, Hyunjin Kim, Jin Hyup Lee, Jeen-Woo Park. Pelargonidin ameliorates acetaminophen-induced hepatotoxicity in mice by inhibiting the ROS-induced inflammatory apoptotic response. Biochimie. 2020 Jan; 168(?):10-16. doi: 10.1016/j.biochi.2019.10.009. [PMID: 31669604]
  • Asmita Samadder, Debojyoti Tarafdar, Ruchira Das, Anisur Rahman Khuda-Bukhsh, Suresh K Abraham. Efficacy of nanoencapsulated pelargonidin in ameliorating pesticide toxicity in fish and L6 cells: Modulation of oxidative stress and signalling cascade. The Science of the total environment. 2019 Jun; 671(?):466-473. doi: 10.1016/j.scitotenv.2019.03.381. [PMID: 31331442]
  • Yanfang Liu, Jianhua Zhang, Xiaohong Yang, Jiangmin Wang, Yangang Li, Peng Zhang, Jin Mao, Qingmei Huang, Hao Tang. Diversity in flower colorations of Ranunculus asiaticus L. revealed by anthocyanin biosynthesis pathway in view of gene composition, gene expression patterns, and color phenotype. Environmental science and pollution research international. 2019 May; 26(14):13785-13794. doi: 10.1007/s11356-018-2779-3. [PMID: 30145754]
  • Gianfranco Diretto, Xin Jin, Teresa Capell, Changfu Zhu, Lourdes Gomez-Gomez. Differential accumulation of pelargonidin glycosides in petals at three different developmental stages of the orange-flowered gentian (Gentiana lutea L. var. aurantiaca). PloS one. 2019; 14(2):e0212062. doi: 10.1371/journal.pone.0212062. [PMID: 30742659]
  • In-Chul Lee, Jong-Sup Bae. Pelargonidin Protects Against Renal Injury in a Mouse Model of Sepsis. Journal of medicinal food. 2019 Jan; 22(1):57-61. doi: 10.1089/jmf.2018.4230. [PMID: 30160593]
  • Eliza Łata, Agnieszka Fulczyk, Teresa Kowalska, Mieczysław Sajewicz. Vulnerability of anthocyanins to the components of a thin-layer chromatographic system and comprehensive screening of anthocyanes in alimentary products. Journal of chromatography. A. 2018 Oct; 1572(?):137-144. doi: 10.1016/j.chroma.2018.08.040. [PMID: 30150119]
  • Mark Levisson, Constantinos Patinios, Sascha Hein, Philip A de Groot, Jean-Marc Daran, Robert D Hall, Stefan Martens, Jules Beekwilder. Engineering de novo anthocyanin production in Saccharomyces cerevisiae. Microbial cell factories. 2018 Jul; 17(1):103. doi: 10.1186/s12934-018-0951-6. [PMID: 29970082]
  • Rocio González-Barrio, María Jesús Periago, Cristina Luna-Recio, Francisco Javier Garcia-Alonso, Inmaculada Navarro-González. Chemical composition of the edible flowers, pansy (Viola wittrockiana) and snapdragon (Antirrhinum majus) as new sources of bioactive compounds. Food chemistry. 2018 Jun; 252(?):373-380. doi: 10.1016/j.foodchem.2018.01.102. [PMID: 29478556]
  • Wenji Xu, Gangjun Luo, Fengyang Yu, Qingxiang Jia, Yang Zheng, Xiaoying Bi, Jiajun Lei. Characterization of anthocyanins in the hybrid progenies derived from Iris dichotoma and I. domestica by HPLC-DAD-ESI/MS analysis. Phytochemistry. 2018 Jun; 150(?):60-74. doi: 10.1016/j.phytochem.2018.03.003. [PMID: 29550699]
  • Ana-Maria Oancea, Cristina Onofrei, Mihaela Turturică, Gabriela Bahrim, Gabriela Râpeanu, Nicoleta Stănciuc. The kinetics of thermal degradation of polyphenolic compounds from elderberry ( Sambucus nigra L.) extract. Food science and technology international = Ciencia y tecnologia de los alimentos internacional. 2018 Jun; 24(4):361-369. doi: 10.1177/1082013218756139. [PMID: 29409346]
  • Sha Xie, Ting Zhao, Zhenwen Zhang, Jiangfei Meng. Reduction of Dihydrokaempferol by Vitis vinfera Dihydroflavonol 4-Reductase to Produce Orange Pelargonidin-Type Anthocyanins. Journal of agricultural and food chemistry. 2018 Apr; 66(13):3524-3532. doi: 10.1021/acs.jafc.7b05766. [PMID: 29554804]
  • Yunting Zhang, Leiyu Jiang, Yali Li, Qing Chen, Yuntian Ye, Yong Zhang, Ya Luo, Bo Sun, Xiaorong Wang, Haoru Tang. Effect of Red and Blue Light on Anthocyanin Accumulation and Differential Gene Expression in Strawberry (Fragaria × ananassa). Molecules (Basel, Switzerland). 2018 Apr; 23(4):. doi: 10.3390/molecules23040820. [PMID: 29614032]
  • Swathi Putta, Nagendra Sastry Yarla, Eswar Kumar K, Dhananjaya Bhadrapura Lakkappa, Mohammad A Kamal, Luciana Scotti, Marcus T Scotti, Ghulam Md Ashraf, B Sasi Bhusana Rao, Sarala Kumari D, Gorla V Reddy, Vadim V Tarasov, Sarat Babu Imandi, Gjumrakch Aliev. Preventive and Therapeutic Potentials of Anthocyanins in Diabetes and Associated Complications. Current medicinal chemistry. 2018; 25(39):5347-5371. doi: 10.2174/0929867325666171206101945. [PMID: 29210634]
  • Natesan Karthi, Arumugasamy Karthiga, Thangaraj Kalaiyarasu, Antony Stalin, Vaiyapuri Manju, Sanjeev Kumar Singh, Ravi Cyril, Sang-Myeong Lee. Exploration of cell cycle regulation and modulation of the DNA methylation mechanism of pelargonidin: Insights from the molecular modeling approach. Computational biology and chemistry. 2017 Oct; 70(?):175-185. doi: 10.1016/j.compbiolchem.2017.08.002. [PMID: 28950208]
  • Hany Bashandy, Teemu H Teeri. Genetically engineered orange petunias on the market. Planta. 2017 Aug; 246(2):277-280. doi: 10.1007/s00425-017-2722-8. [PMID: 28647812]
  • Judith Müller-Maatsch, Lena Bechtold, Ralf M Schweiggert, Reinhold Carle. Co-pigmentation of pelargonidin derivatives in strawberry and red radish model solutions by the addition of phenolic fractions from mango peels. Food chemistry. 2016 Dec; 213(?):625-634. doi: 10.1016/j.foodchem.2016.06.097. [PMID: 27451227]
  • Amol N Nankar, Barry Dungan, Neil Paz, Nilusha Sudasinghe, Tanner Schaub, F Omar Holguin, Richard C Pratt. Quantitative and qualitative evaluation of kernel anthocyanins from southwestern United States blue corn. Journal of the science of food and agriculture. 2016 Oct; 96(13):4542-52. doi: 10.1002/jsfa.7671. [PMID: 26879128]
  • Eunyoung Park, Indika Edirisinghe, Hequn Wei, Lakshmi Prabha Vijayakumar, Katarzyna Banaszewski, Jack C Cappozzo, Britt Burton-Freeman. A dose-response evaluation of freeze-dried strawberries independent of fiber content on metabolic indices in abdominally obese individuals with insulin resistance in a randomized, single-blinded, diet-controlled crossover trial. Molecular nutrition & food research. 2016 05; 60(5):1099-109. doi: 10.1002/mnfr.201500845. [PMID: 26842771]
  • Yun-Song Lai, Sha Li, Qian Tang, Huan-Xiu Li, Shen-Xiang Chen, Pin-Wu Li, Jin-Yi Xu, Yan Xu, Xiang Guo. The Dark-Purple Tea Cultivar 'Ziyan' Accumulates a Large Amount of Delphinidin-Related Anthocyanins. Journal of agricultural and food chemistry. 2016 Apr; 64(13):2719-26. doi: 10.1021/acs.jafc.5b04036. [PMID: 26996195]
  • Susana Espin, Susana Gonzalez-Manzano, Verónica Taco, Cristina Poveda, Begoña Ayuda-Durán, Ana M Gonzalez-Paramas, Celestino Santos-Buelga. Phenolic composition and antioxidant capacity of yellow and purple-red Ecuadorian cultivars of tree tomato (Solanum betaceum Cav.). Food chemistry. 2016 Mar; 194(?):1073-80. doi: 10.1016/j.foodchem.2015.07.131. [PMID: 26471655]
  • Anne-Christin Warskulat, Evangelos C Tatsis, Bettina Dudek, Marco Kai, Sybille Lorenz, Bernd Schneider. Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids. Chembiochem : a European journal of chemical biology. 2016 Feb; 17(4):318-27. doi: 10.1002/cbic.201500572. [PMID: 26670055]
  • Chang Ha Park, Thanislas Bastin Baskar, Soo-Yun Park, Sun-Ju Kim, Mariadhas Valan Arasu, Naif Abdullah Al-Dhabi, Jae Kwang Kim, Sang Un Park. Metabolic Profiling and Antioxidant Assay of Metabolites from Three Radish Cultivars (Raphanus sativus). Molecules (Basel, Switzerland). 2016 Jan; 21(2):157. doi: 10.3390/molecules21020157. [PMID: 26828471]
  • Maria Paula Junqueira-Gonçalves, Lina Yáñez, Carolina Morales, Muriel Navarro, Rodrigo A Contreras, Gustavo E Zúñiga. Isolation and characterization of phenolic compounds and anthocyanins from Murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity. Molecules (Basel, Switzerland). 2015 Mar; 20(4):5698-713. doi: 10.3390/molecules20045698. [PMID: 25838172]
  • Yue Zhu, Qing-Zhong Peng, Ke-Gang Li, De-Yu Xie. Molecular cloning and functional characterization of the anthocyanidin reductase gene from Vitis bellula. Planta. 2014 Aug; 240(2):381-98. doi: 10.1007/s00425-014-2094-2. [PMID: 24880552]
  • Silvija Miosic, Jana Thill, Malvina Milosevic, Christian Gosch, Sabrina Pober, Christian Molitor, Shaghef Ejaz, Annette Rompel, Karl Stich, Heidi Halbwirth. Dihydroflavonol 4-reductase genes encode enzymes with contrasting substrate specificity and show divergent gene expression profiles in Fragaria species. PloS one. 2014; 9(11):e112707. doi: 10.1371/journal.pone.0112707. [PMID: 25393679]
  • Alzbeta Kamenickova, Eva Anzenbacherova, Petr Pavek, Anatoly A Soshilov, Michael S Denison, Michaela Zapletalova, Pavel Anzenbacher, Zdenek Dvorak. Effects of anthocyanins on the AhR-CYP1A1 signaling pathway in human hepatocytes and human cancer cell lines. Toxicology letters. 2013 Jul; 221(1):1-8. doi: 10.1016/j.toxlet.2013.05.007. [PMID: 23735880]
  • Branka Mozetič Vodopivec, Jing Wang, Anne L Møller, Jacob Krake, Torben Lund, Poul Erik Hansen, Søren Laurentius Nielsen. Differences in the structure of anthocyanins from the two amphibious plants, Lobelia cardinalis and Nesaea crassicaulis. Natural product research. 2013 Apr; 27(7):654-64. doi: 10.1080/14786419.2012.688046. [PMID: 22694738]
  • Mi Jin Lee, Jeong Seob Park, Dong Seong Choi, Mun Yhung Jung. Characterization and quantitation of anthocyanins in purple-fleshed sweet potatoes cultivated in Korea by HPLC-DAD and HPLC-ESI-QTOF-MS/MS. Journal of agricultural and food chemistry. 2013 Mar; 61(12):3148-58. doi: 10.1021/jf3055455. [PMID: 23464823]
  • Takashi Ichiyanagi, Yoshiki Kashiwada, Yasuo Shida, Michiko Sekiya, Yoshihiko Hatano, Yoshihisa Takaishi, Yasumasa Ikeshiro. Structural elucidation and biological fate of two glucuronyl metabolites of pelargonidin 3-O-β-D-glucopyranoside in rats. Journal of agricultural and food chemistry. 2013 Jan; 61(3):569-78. doi: 10.1021/jf3032793. [PMID: 23256460]
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