Dihydro-resveratrol (BioDeep_00000017318)

 

Secondary id: BioDeep_00000004007, BioDeep_00000867863

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


5-[2-(4-Hydroxy-phenyl)-ethyl]-benzene-1,3-diol

化学式: C14H14O3 (230.0943)
中文名称: 二氢白藜芦醇, 二氢藜芦醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 45.79%

分子结构信息

SMILES: C1=C(O)C=C(CCC2=CC=C(O)C=C2)C=C1O
InChI: InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2

描述信息

Dihydroresveratrol is a stilbenol that is 1,1-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4. It has a role as a xenobiotic metabolite and a plant metabolite.
Dihydroresveratrol is a natural product found in Blasia pusilla, Dioscorea dumetorum, and other organisms with data available.
A stilbenol that is 1,1-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4.
Dihydroresveratrol, a potent phytoestrogen, is a hormone receptor modulator. Dihydroresveratrol exhibits proliferative effects in androgen-independent prostate and breast cancer cells at picomolar and nanomolar concentrations[1].
Dihydroresveratrol, a potent phytoestrogen, is a hormone receptor modulator. Dihydroresveratrol exhibits proliferative effects in androgen-independent prostate and breast cancer cells at picomolar and nanomolar concentrations[1].

同义名列表

19 个代谢物同义名

5-[2-(4-Hydroxy-phenyl)-ethyl]-benzene-1,3-diol; ButanaMide, 4-aMino-N-ethyl-, Monohydrochloride; 1,3-Benzenediol, 5-(2-(4-hydroxyphenyl)ethyl)-; 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol; alpha,beta-dihydro-3,40,5-trihydroxystilbene; 5-(2-(4-HYDROXYPHENYL)ETHYL)BENZENE-1,3-DIOL; 5-(4-hydroxyphenethyl)benzene-1,3-diol; alpha,beta-Dihydroresveratrol; 3,4,5-trihydroxybibenzyl; 3,5,4-trihydroxybibenzyl; 3,4,5-Trihydroxybibenzyl; a, b-Dihydroresveratrol; dihydro-resveratrol; Dihydroresveratrol; UNII-CBY43AY0TT; CBY43AY0TT; 3ftu; RE2; Dihydroresveratrol



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(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)

13 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 AHR, CYP3A4, MAPK14, MARK2, PCK1, PIK3C3, PRKAA2, SIRT1
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 2 CYP1B1, CYP3A4
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 5 AHR, MAPK14, MPO, PRKAA2, SIRT1
autophagosome 1 PIK3C3
cytosol 8 AHR, LEP, MAPK14, PCK1, PIK3C3, PRKAA2, SIRT1, TPH1
dendrite 2 MARK2, PRKAA2
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
nucleoplasm 6 AHR, MAPK14, MARK2, MPO, PRKAA2, SIRT1
Cell membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Multi-pass membrane protein 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
cell surface 1 ADIPOQ
glutamatergic synapse 2 MAPK14, PIK3C3
Golgi apparatus 1 PRKAA2
Golgi membrane 1 INS
neuronal cell body 1 PRKAA2
Cytoplasm, cytosol 1 PCK1
Lysosome 1 MPO
endosome 1 PIK3C3
plasma membrane 5 MARK2, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Membrane 9 CYP1B1, CYP3A4, MARK2, PIK3C3, PRKAA2, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
apical plasma membrane 2 SLCO1A2, SLCO2B1
axon 1 PRKAA2
basolateral plasma membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
extracellular exosome 2 MPO, PCK1
endoplasmic reticulum 2 ADIPOQ, PCK1
extracellular space 6 ADIPOQ, IL17A, IL6, INS, LEP, MPO
mitochondrion 4 CYP1B1, MAPK14, MARK2, SIRT1
protein-containing complex 1 AHR
intracellular membrane-bounded organelle 3 CYP1B1, CYP3A4, MPO
Microsome membrane 2 CYP1B1, CYP3A4
chromatin silencing complex 1 SIRT1
Secreted 5 ADIPOQ, IL17A, IL6, INS, LEP
extracellular region 7 ADIPOQ, IL17A, IL6, INS, LEP, MAPK14, MPO
transcription regulator complex 1 AHR
external side of plasma membrane 1 IL17A
nucleolus 1 SIRT1
midbody 1 PIK3C3
Apical cell membrane 1 SLCO2B1
heterochromatin 1 SIRT1
GABA-ergic synapse 1 PIK3C3
Peroxisome 1 PIK3C3
collagen trimer 1 ADIPOQ
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
collagen-containing extracellular matrix 1 ADIPOQ
secretory granule 1 MPO
lateral plasma membrane 1 MARK2
axoneme 1 PIK3C3
nuclear speck 2 MAPK14, PRKAA2
nuclear inner membrane 1 SIRT1
Late endosome 1 PIK3C3
neuron projection 1 TPH1
chromatin 2 AHR, SIRT1
phagocytic vesicle membrane 1 PIK3C3
spindle pole 1 MAPK14
actin filament 1 MARK2
Basolateral cell membrane 3 SLCO1B1, SLCO1B3, SLCO2B1
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
endosome lumen 1 INS
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
aryl hydrocarbon receptor complex 1 AHR
Cell projection, dendrite 1 MARK2
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
basal plasma membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
presynaptic endosome 1 PIK3C3
phagocytic vesicle lumen 1 MPO
Basal cell membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
nucleotide-activated protein kinase complex 1 PRKAA2
postsynaptic endosome 1 PIK3C3
Autolysosome 1 PIK3C3
interleukin-6 receptor complex 1 IL6
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
microtubule bundle 1 MARK2
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Chu-Shing Lam, Yi-Xuan Xia, Bai-Sen Chen, Yin-Xiao Du, Kang-Lun Liu, Hong-Jie Zhang. Dihydro-Resveratrol Attenuates Oxidative Stress, Adipogenesis and Insulin Resistance in In Vitro Models and High-Fat Diet-Induced Mouse Model via AMPK Activation. Nutrients. 2023 Jun; 15(13):. doi: 10.3390/nu15133006. [PMID: 37447331]
  • Antonio González-Sarrías, Juan Carlos Espín-Aguilar, Salvador Romero-Reyes, Julio Puigcerver, Mateo Alajarín, José Berná, María Victoria Selma, Juan Carlos Espín. Main Determinants Affecting the Antiproliferative Activity of Stilbenes and Their Gut Microbiota Metabolites in Colon Cancer Cells: A Structure-Activity Relationship Study. International journal of molecular sciences. 2022 Dec; 23(23):. doi: 10.3390/ijms232315102. [PMID: 36499424]
  • Miklós Poór, Hana Kaci, Slávka Bodnárová, Violetta Mohos, Eszter Fliszár-Nyúl, Sándor Kunsági-Máté, Csilla Özvegy-Laczka, Beáta Lemli. Interactions of resveratrol and its metabolites (resveratrol-3-sulfate, resveratrol-3-glucuronide, and dihydroresveratrol) with serum albumin, cytochrome P450 enzymes, and OATP transporters. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jul; 151(?):113136. doi: 10.1016/j.biopha.2022.113136. [PMID: 35594715]
  • Qiang-Guo Ji, Ming-Hua Ma, Xue-Mei Hu, Yi-Jun Zhang, Xiao-Hong Xu, Hua Nian. Detection and structural characterization of the metabolites of dihydroresveratrol in rats by liquid chromatography coupled to high-resolution tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2021 Feb; 35(4):e8991. doi: 10.1002/rcm.8991. [PMID: 33125777]
  • Ilka Günther, Gerald Rimbach, Carina I Mack, Christoph H Weinert, Nicolas Danylec, Kai Lüersen, Marc Birringer, Franz Bracher, Sebastian T Soukup, Sabine E Kulling, Kathrin Pallauf. The Putative Caloric Restriction Mimetic Resveratrol has Moderate Impact on Insulin Sensitivity, Body Composition, and the Metabolome in Mice. Molecular nutrition & food research. 2020 03; 64(6):e1901116. doi: 10.1002/mnfr.201901116. [PMID: 31962371]
  • Veronika Jarosova, Ondrej Vesely, Ivo Doskocil, Katerina Tomisova, Petr Marsik, Jose D Jaimes, Karel Smejkal, Pavel Kloucek, Jaroslav Havlik. Metabolism of cis- and trans-Resveratrol and Dihydroresveratrol in an Intestinal Epithelial Model. Nutrients. 2020 Feb; 12(3):. doi: 10.3390/nu12030595. [PMID: 32106482]
  • Juan Antonio Giménez-Bastida, María Ángeles Ávila-Gálvez, Juan Carlos Espín, Antonio González-Sarrías. Conjugated Physiological Resveratrol Metabolites Induce Senescence in Breast Cancer Cells: Role of p53/p21 and p16/Rb Pathways, and ABC Transporters. Molecular nutrition & food research. 2019 11; 63(22):e1900629. doi: 10.1002/mnfr.201900629. [PMID: 31441212]
  • María Ángeles Ávila-Gálvez, Juan Carlos Espín, Antonio González-Sarrías. Physiological Relevance of the Antiproliferative and Estrogenic Effects of Dietary Polyphenol Aglycones versus Their Phase-II Metabolites on Breast Cancer Cells: A Call of Caution. Journal of agricultural and food chemistry. 2018 Aug; 66(32):8547-8555. doi: 10.1021/acs.jafc.8b03100. [PMID: 30025453]
  • Sara Vitalini, Serhat S Cicek, Sebastian Granica, Christian Zidorn. Dihydroresveratrol Type Dihydrostilbenoids: Chemical Diversity, Chemosystematics, and Bioactivity. Current medicinal chemistry. 2018; 25(10):1194-1240. doi: 10.2174/0929867324666170830112343. [PMID: 28875843]
  • Marie-Claude Menet, Stephanie Baron, Meryam Taghi, Remi Diestra, Delphine Dargère, Olivier Laprévote, Valérie Nivet-Antoine, Jean-Louis Beaudeux, Tatiana Bédarida, Charles-Henry Cottart. Distribution of trans-resveratrol and its metabolites after acute or sustained administration in mouse heart, brain, and liver. Molecular nutrition & food research. 2017 08; 61(8):. doi: 10.1002/mnfr.201600686. [PMID: 28160405]
  • Syuhei Nakao, Miyuki Mabuchi, Shenglan Wang, Yoko Kogure, Tadashi Shimizu, Koichi Noguchi, Akito Tanaka, Yi Dai. Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor. Bioorganic & medicinal chemistry letters. 2017 07; 27(14):3167-3172. doi: 10.1016/j.bmcl.2017.05.025. [PMID: 28576617]
  • Silvie Timmers, Marlies de Ligt, Esther Phielix, Tineke van de Weijer, Jan Hansen, Esther Moonen-Kornips, Gert Schaart, Iris Kunz, Matthijs K C Hesselink, Vera B Schrauwen-Hinderling, Patrick Schrauwen. Resveratrol as Add-on Therapy in Subjects With Well-Controlled Type 2 Diabetes: A Randomized Controlled Trial. Diabetes care. 2016 Dec; 39(12):2211-2217. doi: 10.2337/dc16-0499. [PMID: 27852684]
  • Xuan Hong Thy Nguyen, Ole Johan Juvik, Dag Olav Øvstedal, Torgils Fossen. 6-carboxydihydroresveratrol 3-O-β-glucopyranoside--a novel natural product from the Cretaceous relict Metasequoia glyptostroboides. Fitoterapia. 2014 Jun; 95(?):109-14. doi: 10.1016/j.fitote.2014.03.001. [PMID: 24631762]
  • Diana C Rueda, Angela Schöffmann, Maria De Mieri, Melanie Raith, Evelyn A Jähne, Steffen Hering, Matthias Hamburger. Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators. Bioorganic & medicinal chemistry. 2014 Feb; 22(4):1276-84. doi: 10.1016/j.bmc.2014.01.008. [PMID: 24462176]
  • Itsuo Murakami, Romanas Chaleckis, Tomáš Pluskal, Ken Ito, Kousuke Hori, Masahiro Ebe, Mitsuhiro Yanagida, Hiroshi Kondoh. Metabolism of skin-absorbed resveratrol into its glucuronized form in mouse skin. PloS one. 2014; 9(12):e115359. doi: 10.1371/journal.pone.0115359. [PMID: 25506824]
  • Yulia Radko, Kathrine B Christensen, Lars P Christensen. Semi-preparative isolation of dihydroresveratrol-3-O-β-d-glucuronide and four resveratrol conjugates from human urine after oral intake of a resveratrol-containing dietary supplement. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jul; 930(?):54-61. doi: 10.1016/j.jchromb.2013.05.002. [PMID: 23727867]
  • Lisa M Bode, Diana Bunzel, Melanie Huch, Gyu-Sung Cho, Denise Ruhland, Mirko Bunzel, Achim Bub, Charles M A P Franz, Sabine E Kulling. In vivo and in vitro metabolism of trans-resveratrol by human gut microbiota. The American journal of clinical nutrition. 2013 Feb; 97(2):295-309. doi: 10.3945/ajcn.112.049379. [PMID: 23283496]
  • María Azorín-Ortuño, María J Yáñez-Gascón, Antonio González-Sarrías, Mar Larrosa, Fernando Vallejo, Francisco J Pallarés, Ricardo Lucas, Juan C Morales, Francisco A Tomás-Barberán, María-Teresa García-Conesa, Juan C Espín. Effects of long-term consumption of low doses of resveratrol on diet-induced mild hypercholesterolemia in pigs: a transcriptomic approach to disease prevention. The Journal of nutritional biochemistry. 2012 Jul; 23(7):829-37. doi: 10.1016/j.jnutbio.2011.04.007. [PMID: 21852083]
  • María Azorín-Ortuño, María J Yáñez-Gascón, Fernando Vallejo, Francisco J Pallarés, Mar Larrosa, Ricardo Lucas, Juan C Morales, Francisco A Tomás-Barberán, María T García-Conesa, Juan C Espín. Metabolites and tissue distribution of resveratrol in the pig. Molecular nutrition & food research. 2011 Aug; 55(8):1154-68. doi: 10.1002/mnfr.201100140. [PMID: 21710561]
  • Donggeng Wang, Zhiwen Zhang, Jianfeng Ju, Xinyang Wang, Wenjing Qiu. Investigation of piceid metabolites in rat by liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jan; 879(1):69-74. doi: 10.1016/j.jchromb.2010.11.012. [PMID: 21130054]
  • Thomas Walle. Bioavailability of resveratrol. Annals of the New York Academy of Sciences. 2011 Jan; 1215(?):9-15. doi: 10.1111/j.1749-6632.2010.05842.x. [PMID: 21261636]
  • M Emília Juan, Irene Alfaras, Joana M Planas. Determination of dihydroresveratrol in rat plasma by HPLC. Journal of agricultural and food chemistry. 2010 Jun; 58(12):7472-5. doi: 10.1021/jf100836j. [PMID: 20509689]
  • Min Wang, Chao-feng Zhang, Zheng-tao Wang, Mian Zhang. [Studies on constituents of Dendrobium gratiosissimum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(8):701-3. doi: . [PMID: 17608224]
  • Donggeng Wang, Taijun Hang, Chunyong Wu, Wenying Liu. Identification of the major metabolites of resveratrol in rat urine by HPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Dec; 829(1-2):97-106. doi: 10.1016/j.jchromb.2005.09.040. [PMID: 16243591]
  • Yanet Hernández-Romero, Laura Acevedo, María de los Angeles Sánchez, W Thomas Shier, Hamed K Abbas, Rachel Mata. Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum. Journal of agricultural and food chemistry. 2005 Aug; 53(16):6276-80. doi: 10.1021/jf0508044. [PMID: 16076106]
  • Yanet Hernández-Romero, Juana-Isela Rojas, Rafael Castillo, Alejandra Rojas, Rachel Mata. Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii. Journal of natural products. 2004 Feb; 67(2):160-7. doi: 10.1021/np030303h. [PMID: 14987052]
  • L A Stivala, M Savio, F Carafoli, P Perucca, L Bianchi, G Maga, L Forti, U M Pagnoni, A Albini, E Prosperi, V Vannini. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. The Journal of biological chemistry. 2001 Jun; 276(25):22586-94. doi: 10.1074/jbc.m101846200. [PMID: 11316812]
  • H Matsuda, T Kageura, T Morikawa, I Toguchida, S Harima, M Yoshikawa. Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorganic & medicinal chemistry letters. 2000 Feb; 10(4):323-7. doi: 10.1016/s0960-894x(99)00702-7. [PMID: 10714491]
  • A W Mondorf. [Evidence of urinary tubular proteins in inflammatory and toxic kidney damage]. Wiener medizinische Wochenschrift. Supplement. 1975; 27(?):20-3. doi: NULL. [PMID: 5816]