3,4-Dihydroxybenzaldehyde (BioDeep_00000229764)

 

Secondary id: BioDeep_00000002890, BioDeep_00000400507, BioDeep_00000860572

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


3,4-Dihydroxybenzaldehyde, Vetec(TM) reagent grade, 97\\%

化学式: C7H6O3 (138.03169259999999)
中文名称: 3,4-二羟基苯甲醛, 原儿茶醛
谱图信息: 最多检出来源 Homo sapiens(blood) 0.62%

分子结构信息

SMILES: C1=CC(=C(C=C1C=O)O)O
InChI: InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H

描述信息

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus .
3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.
Also known as protocatechuic aldehyde, protocatechualdehyde is a naturally-occuring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza. Protocatechualdehyde possesses antiproliferative and pro-apoptotic properties against human breast cancer cells and colorectal cancer cells by reducing the expression of pro-oncogenes β-catenin and cyclin D1.
3,4-Dihydroxybenzaldehyde is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available.
See also: Black Cohosh (part of).
3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia).
D006401 - Hematologic Agents > D000925 - Anticoagulants
Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].
Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

同义名列表

35 个代谢物同义名

3,4-Dihydroxybenzaldehyde, Vetec(TM) reagent grade, 97\\%; 3,4-Dihydroxybenzaldehyde, purum, >=97.0\\% (HPLC); InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10; 3,4-Dihydroxybenzaldehyde, analytical standard; protocatechualdehyde, formyl-14C-labeled; protocatechualdehyde, 3H-labeled; 3,4-Dihydroxybenzaldehyde, 97\\%; PROTOCATECHUICALDEHYDE [INCI]; 4-Formyl-1,2-dihydroxybenzene; 1,2-Dihydroxy-4-formylbenzene; 3,4-Dihydroxybenzyl aldehyde; 3,4-Dihydroxybenzenecarbonal; Benzaldehyde, 3,4-dihydroxy-; O HUI WHITE EXTREME CELLIGHT; DIHYDROXYBENZALDEHYDE, 3,4-; 3,4-dihydroxy benzaldehyde; 3,4-dihydroxy-benzaldehyde; 3, 4-Dihydroxybenzaldehyde; 4,5-Dihydroxybenzaldehyde; 3,4 dihydroxybenzaldehyde; 3,4-dihydroxybenzaldehyde; PROTOCATECHUALDEHYDE [MI]; 4-Formyl-1,2-benzenediol; protocatechuic aldehyde; protocatechuicaldehyde; Protocatechualdehyde; rancinamycin IV; UNII-4PVP2HCH4T; catechaldehyde; MEGxm0_000158; ACon1_001620; 3,4-DHBAOP; 4PVP2HCH4T; GM-W03; H6N



数据库引用编号

19 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(1)

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)

64 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 Zhang, Yuan Li, Wenqing Yang, Lin Lin, Jie Li, Dekun Liu, Chao Li, Jibiao Wu, Yunlun Li. Protocatechuic aldehyde increases pericyte coverage and mitigates pericyte damage to enhance the atherosclerotic plaque stability. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Dec; 168(?):115742. doi: 10.1016/j.biopha.2023.115742. [PMID: 37871558]
  • Yangjing Bai, Shiying Lang, Yangrui Du, Qinsheng Hu, Xinyun Li, Gongyan Liu. Metallic-Polyphenolic Nanoparticles Reinforced Cationic Guar Gum Hydrogel for Effectively Treating Burn Wound. Macromolecular bioscience. 2023 Oct; ?(?):e2300396. doi: 10.1002/mabi.202300396. [PMID: 37831011]
  • Shao-Ru Wu, Wei-Hong Feng, Kai-Ming Chen, Liang-Jun Guan, Liang-Mian Chen, Zhi-Min Wang, Hui-Min Gao, Zong-Hua Song. [Chemical composition and antioxidant activity of different parts of Prunella vulgaris by UPLC-Q-TOF-MS/MS and UPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Sep; 48(17):4569-4588. doi: 10.19540/j.cnki.cjcmm.20221227.202. [PMID: 37802797]
  • Chunliu Wang, Jie Zhou, Shixiang Wang, Yang Liu, Kaihua Long, Tingting Sun, Wenbing Zhi, Yang Yang, Hong Zhang, Ye Zhao, Xiaopu Zheng, Xiaohui Zheng, Ye Li, Pu Jia. Guanxining injection alleviates fibrosis in heart failure mice and regulates SLC7A11/GPX4 axis. Journal of ethnopharmacology. 2023 Jun; 310(?):116367. doi: 10.1016/j.jep.2023.116367. [PMID: 36914037]
  • Junxia Pei, Zhou Su, Xin Zeng, Ya Zhong, Yamei Zhang, Yixi Yang, Qiuxia Lu, Jian Li, Yu Deng. Protocatechuic aldehyde acts synergistically with dacarbazine to augment DNA double-strand breaks and promote apoptosis in cutaneous melanoma cells. BMC complementary medicine and therapies. 2023 Apr; 23(1):111. doi: 10.1186/s12906-023-03933-w. [PMID: 37024907]
  • Pengjun Wang, Qingxiang Zhang. Protocatechuic aldehyde alleviates D-galactose-induced cardiomyocyte senescence by regulating the TCF3 / ATG5 axis. Journal of cardiovascular pharmacology. 2022 Dec; ?(?):. doi: 10.1097/fjc.0000000000001394. [PMID: 36651950]
  • Xin-Yu Lin, Jing Zhou, Cai-Feng Hao, He Zhu, Shan-Shan Zhou, Jin-Di Xu, Qian Mao, Song-Lin Li, Ming Kong. Quality consistency evaluation of commercial Prunellae Spica by integrating determination of secondary metabolites and saccharides. Phytochemical analysis : PCA. 2022 Dec; ?(?):. doi: 10.1002/pca.3197. [PMID: 36494085]
  • Yu-Teng Chang, Mu-Chi Chung, Chi-Hao Chang, Kuan-Hsun Chiu, Jeng-Jer Shieh, Ming-Ju Wu. Anti-EMT and anti-fibrosis effects of protocatechuic aldehyde in renal proximal tubular cells and the unilateral ureteral obstruction animal model. Pharmaceutical biology. 2022 Dec; 60(1):1198-1206. doi: 10.1080/13880209.2022.2088809. [PMID: 35758295]
  • Nikhil Maheshwari, Riaz Mahmood. 3,4-Dihydroxybenzaldehyde attenuates pentachlorophenol-induced cytotoxicity, DNA damage and collapse of mitochondrial membrane potential in isolated human blood cells. Drug and chemical toxicology. 2022 May; 45(3):1225-1242. doi: 10.1080/01480545.2020.1811722. [PMID: 32854525]
  • Eun-A Kim, Eui-Jeong Han, Junseong Kim, Ilekuttige Priyan Shanura Fernando, Jae-Young Oh, Kil-Nam Kim, Ginnae Ahn, Soo-Jin Heo. Anti-Allergic Effect of 3,4-Dihydroxybenzaldehyde Isolated from Polysiphonia morrowii in IgE/BSA-Stimulated Mast Cells and a Passive Cutaneous Anaphylaxis Mouse Model. Marine drugs. 2022 Feb; 20(2):. doi: 10.3390/md20020133. [PMID: 35200662]
  • Yan Guo, Jie-Hong Yang, Yu He, Hui-Fen Zhou, Yu Wang, Zhi-Shan Ding, Bo Jin, Hai-Tong Wan. Protocatechuic aldehyde prevents ischemic injury by attenuating brain microvascular endothelial cell pyroptosis via lncRNA Xist. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jan; 94(?):153849. doi: 10.1016/j.phymed.2021.153849. [PMID: 34775360]
  • Ruhi Anjum, Nikhil Maheshwari, Riaz Mahmood. 3,4-Dihydroxybenzaldehyde mitigates fluoride-induced cytotoxicity and oxidative damage in human RBC. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2022 Jan; 69(?):126888. doi: 10.1016/j.jtemb.2021.126888. [PMID: 34773916]
  • Yu-Teng Chang, Mu-Chi Chung, Chang-Chi Hsieh, Jeng-Jer Shieh, Ming-Ju Wu. Evaluation of the Therapeutic Effects of Protocatechuic Aldehyde in Diabetic Nephropathy. Toxins. 2021 08; 13(8):. doi: 10.3390/toxins13080560. [PMID: 34437430]
  • Tao Tian, Guo-Ying Chen, Hao Zhang, Feng-Qing Yang. Personal Glucose Meter for α-Glucosidase Inhibitor Screening Based on the Hydrolysis of Maltose. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154638. [PMID: 34361791]
  • Brahmam Kapalavavi, Ninad Doctor, Baohong Zhang, Yu Yang. Subcritical Water Extraction of Salvia miltiorrhiza. Molecules (Basel, Switzerland). 2021 Mar; 26(6):. doi: 10.3390/molecules26061634. [PMID: 33804141]
  • Jieke Yang, Jianchun Li, Ruizhi Tan, Xingcan He, Xiao Lin, Xia Zhong, Junming Fan, Li Wang. Protocatechualdehyde attenuates obstructive nephropathy through inhibiting lncRNA9884 induced inflammation. Phytotherapy research : PTR. 2021 Mar; 35(3):1521-1533. doi: 10.1002/ptr.6919. [PMID: 33118280]
  • Yan-Jun Wan, Yan-Hang Wang, Qiang Guo, Yong Jiang, Peng-Fei Tu, Ke-Wu Zeng. Protocatechualdehyde protects oxygen-glucose deprivation/reoxygenation-induced myocardial injury via inhibiting PERK/ATF6α/IRE1α pathway. European journal of pharmacology. 2021 Jan; 891(?):173723. doi: 10.1016/j.ejphar.2020.173723. [PMID: 33159933]
  • Yunyun Qu, Xin Liu, Shuai Zong, Huanxin Sun, Shuang Liu, Yueran Zhao. Protocatechualdehyde Inhibits the Osteoclast Differentiation of RAW264.7 and BMM Cells by Regulating NF-κB and MAPK Activity. BioMed research international. 2021; 2021(?):6108999. doi: 10.1155/2021/6108999. [PMID: 34327232]
  • Shuang Wu, Qingyu Wang, Jinquan Wang, Baoyu Duan, Qihe Tang, Zhuojian Sun, Jinlong Han, Chenggang Shan, Zhifen Wang, Zhihui Hao. Protocatechuic aldehyde from Salvia miltiorrhiza exhibits an anti-inflammatory effect through inhibiting MAPK signalling pathway. BMC complementary medicine and therapies. 2020 Nov; 20(1):347. doi: 10.1186/s12906-020-03090-4. [PMID: 33203388]
  • Danqing Wang, Shuangshuang Zhang, Han Tang, Cuiping Jiang, Bingwei Wang, Jianping Liu. Development of sustained-release pellets to modulate the in vivo processes of the main active components of Danshen: A pharmacokinetic and pharmacodynamic evaluation. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 May; 58(?):152793. doi: 10.1016/j.phymed.2018.12.016. [PMID: 31005724]
  • Aparna Singh, Marie-Ange Massicotte, Ariane Garand, Laurence Tousignant, Vincent Ouellette, Gervais Bérubé, Isabel Desgagné-Penix. Cloning and characterization of norbelladine synthase catalyzing the first committed reaction in Amaryllidaceae alkaloid biosynthesis. BMC plant biology. 2018 Dec; 18(1):338. doi: 10.1186/s12870-018-1570-4. [PMID: 30526483]
  • Nazim Husain, Riaz Mahmood. 3,4-Dihydroxybenzaldehyde quenches ROS and RNS and protects human blood cells from Cr(VI)-induced cytotoxicity and genotoxicity. Toxicology in vitro : an international journal published in association with BIBRA. 2018 Aug; 50(?):293-304. doi: 10.1016/j.tiv.2018.04.004. [PMID: 29665407]
  • Bin Sun, Peng Wang, Ren Wang, Yikui Li, Sheng Xu. Molecular Cloning and Characterization of a meta/para-O-Methyltransferase from Lycoris aurea. International journal of molecular sciences. 2018 06; 19(7):. doi: 10.3390/ijms19071911. [PMID: 29966257]
  • Nikhil Maheshwari, Fahim Halim Khan, Riaz Mahmood. 3,4-Dihydroxybenzaldehyde lowers ROS generation and protects human red blood cells from arsenic(III) induced oxidative damage. Environmental toxicology. 2018 May; ?(?):. doi: 10.1002/tox.22572. [PMID: 29732668]
  • Ajing Zhao, Li Zhang, Rong Li, Jiao Shang, Huihui Yi, Yuan Wang, Dian Zhang, Shixiang Wang, Minfeng Fang. Development and validation of an LC-MS/MS method for the simultaneous quantification of seven constituents in rat plasma and application in a pharmacokinetic study of the Zaoren Anshen prescription. Biomedical chromatography : BMC. 2018 Feb; 32(2):. doi: 10.1002/bmc.4055. [PMID: 28744886]
  • Lin Zhang, Huiying Xu, Libin Zhan. Pharmacokinetic Assessments of Liquiritin, Protocatechuic Aldehyde and Rosmarinic Acid in Rat Plasma by UPLC-MS-MS After Administration of ZibuPiyin Recipe. Journal of chromatographic science. 2018 Feb; 56(2):139-146. doi: 10.1093/chromsci/bmx093. [PMID: 29186346]
  • Tsung-Ting Shih, Hui-Ling Lee, Show-Chuen Chen, Chih-Yuan Kang, Ren-Shang Shen, Yi-An Su. Rapid analysis of traditional Chinese medicine Pinellia ternata by microchip electrophoresis with electrochemical detection. Journal of separation science. 2018 Feb; 41(3):740-746. doi: 10.1002/jssc.201700901. [PMID: 29152857]
  • Jing Zhou, Min Li, Weifeng Jin, Xiaohong Li, Hongjin Fan, Yuyan Zhang. Pharmacokinetic Study on Protocatechuic Aldehyde and Hydroxysafflor Yellow A of Danhong Injection in Rats with Hyperlipidemia. Pharmacology. 2018; 102(3-4):154-160. doi: 10.1159/000491020. [PMID: 30045035]
  • Wei Li, Hongjie Zhou, Yang Chu, Xiangyang Wang, Ruizhi Luo, Liu Yang, Navaneethakrishnan Polachi, Xiao Li, Min Chen, Luqi Huang, Xueying Yan, Zhixin Guo, He Sun. Simultaneous determination and pharmacokinetics of danshensu, protocatechuic aldehyde, 4-hydroxy-3-methyloxyphenyl lactic acid and protocatechuic acid in human plasma by LC-MS/MS after oral administration of Compound Danshen Dripping Pills. Journal of pharmaceutical and biomedical analysis. 2017 Oct; 145(?):860-864. doi: 10.1016/j.jpba.2017.06.014. [PMID: 28830061]
  • Yan Song, Lan Pan, Wenjie Li, Yingying Si, Di Zhou, Chengjian Zheng, Xiaofang Hao, Xinyue Jia, Yuemei Jia, Minghui Shi, Xiaoguang Jia, Ning Li, Yue Hou. Natural neuro-inflammatory inhibitors from Caragana turfanensis. Bioorganic & medicinal chemistry letters. 2017 10; 27(20):4765-4769. doi: 10.1016/j.bmcl.2017.08.047. [PMID: 28911817]
  • Wei-Jun Kong, Shan-Shan Zhang, Yan-Ling Zhao, Ming-Quan Wu, Ping Chen, Xiao-Ru Wu, Xin-Ping Ma, Wei-Ying Guo, Mei-Hua Yang. Combination of chemical fingerprint and bioactivity evaluation to explore the antibacterial components of Salvia miltiorrhizae. Scientific reports. 2017 08; 7(1):8112. doi: 10.1038/s41598-017-08377-0. [PMID: 28808259]
  • Yaping Shao, Wen Zhang, Ling Tong, Jingyi Huang, Dongxiang Li, Wei Nie, Yan Zhu, Yunfei Li, Tao Lu. Simultaneous determination of eight bioactive components of Qishen Yiqi dripping pills in rat plasma using UFLC-MS/MS and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2017 Aug; 31(8):. doi: 10.1002/bmc.3941. [PMID: 28146302]
  • Hong-Jing Fan, Li Yu, Wei-Feng Jin, Min Li, Jing Zhou, Xiao-Hong Li, Yu-Yan Zhang. [Pharmacokinetics-pharmacodynamics correlation of protocatechuic aldehyde and hydroxysafflor yellow A alone or their combination use in rats with hyperlipidemia]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Jul; 42(13):2564-2570. doi: 10.19540/j.cnki.cjcmm.20170523.008. [PMID: 28840700]
  • Tingyang Li, Yang Chu, Kaijing Yan, Shuming Li, Xiangyang Wang, Ying Wang, Wei Li, Xiaohui Ma, Jin Yang, Changxiao Liu. Simultaneous determination of tanshinol, protocatechuic aldehyde, protocatechuic acid, notoginsenoside R1, ginsenoside Rg1 and Rb1 in rat plasma by LC-MS/MS and its application. Biomedical chromatography : BMC. 2017 Jun; 31(6):. doi: 10.1002/bmc.3889. [PMID: 28164352]
  • Di Zhou, Hongyan Wei, Zhe Jiang, Xuezheng Li, Kun Jiao, Xiaoguang Jia, Yue Hou, Ning Li. Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):973-978. doi: 10.1016/j.bmcl.2016.12.075. [PMID: 28073678]
  • Shuangshuang Zhang, Hongxiang Yan, Panpan Yu, Yulong Xia, Wenli Zhang, Jianping Liu. Development of protocatechualdehyde proliposomes-based sustained-release pellets with improved bioavailability and desired pharmacokinetic behavior for angina chronotherapy. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2016 Oct; 93(?):341-50. doi: 10.1016/j.ejps.2016.08.040. [PMID: 27568854]
  • Zhanli Liu, Xunyang Zheng, Yanlei Guo, Weihan Qin, Lei Hua, Yong Yang. Quantitatively metabolic profiles of salvianolic acids in rats after gastric-administration of Salvia miltiorrhiza extract. Fitoterapia. 2016 Sep; 113(?):27-34. doi: 10.1016/j.fitote.2016.06.017. [PMID: 27370098]
  • Jung Woo Byun, Sena Hwang, Chan Woo Kang, Jin Hee Kim, Min Kyung Chae, Jin Sook Yoon, Eun Jig Lee. Therapeutic Effect of Protocatechuic Aldehyde in an In Vitro Model of Graves' Orbitopathy. Investigative ophthalmology & visual science. 2016 08; 57(10):4055-62. doi: 10.1167/iovs.15-19037. [PMID: 27494347]
  • Kai Liang, Shuiting Zhai, Zhidong Zhang, Guoquan Wang, Xiaoyang Fu, Tianxiao Li. Study on the small intestine absorptive kinetics characters of tanshinol and protocatechualdehyde of Salvia miltiorrhiza extracts in rats in vivo. Pakistan journal of pharmaceutical sciences. 2016 Jul; 29(4 Suppl):1415-20. doi: . [PMID: 27592492]
  • Hao Ren, Dawei Qian, Shulan Su, Hanliang Guan, Wei Zhang, Erxin Shang, Jinao Duan. Simultaneous determination of tanshinones and polyphenolics in rat plasma by UPLC-MS/MS and its application to the pharmacokinetic interaction between them. Drug testing and analysis. 2016 Jul; 8(7):744-54. doi: 10.1002/dta.1840. [PMID: 26382027]
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