Pinoresinol (BioDeep_00000017492)

Main id: BioDeep_00000000431

 

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


Phenol,4-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2-methoxy-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-

化学式: C20H22O6 (358.1416)
中文名称: (±)-松脂素, 松脂醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
InChI: InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3

描述信息

4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol is a natural product found in Zanthoxylum riedelianum, Forsythia suspensa, and other organisms with data available.
Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].
Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

同义名列表

13 个代谢物同义名

Phenol,4-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2-methoxy-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-; 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol; 4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol; (+)-Pinoresinol, 4,4-((1S,3aR,4S,6aR)-Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol); 4,4-[(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol); 4,4-[Hexahydrofuro[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol); 4,4-(Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol); (+/-)-PINORESINOL; (+)-Pinoresinol; (±)-Pinoresinol; pino-resinol; Pinoresinol; (+)-Pinoresinol



数据库引用编号

16 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)

1079 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


文献列表

  • Jingxian Feng, Yuan Yao, Yuqi Qiao, Xueqi Ma, Zongtai Wu, Yonghao Duan, Peng Di, Wansheng Chen, Ying Xiao. Effect of pinoresinol-lariciresinol reductases on biosynthesis of lignans with substrate selectivity in Schisandra chinensis. Phytochemistry. 2024 May; 221(?):114053. doi: 10.1016/j.phytochem.2024.114053. [PMID: 38479587]
  • Mona Soltani, Reza Fotovat, Mohsen Sharifi, Najmeh Ahmadian Chashmi, Mehrdad Behmanesh. In Vitro Comparative Study on Antineoplastic Effects of Pinoresinol and Lariciresinol on Healthy Cells and Breast Cancer-Derived Human Cells. Iranian journal of medical sciences. 2024 Jan; 49(1):30-39. doi: 10.30476/ijms.2023.94805.2611. [PMID: 38322161]
  • Mareia Ahmed-M Elgaleidh, Hafize Dilek Tepe, Fatma Doyuk, Talip Çeter, İdris Yazgan. Identification of Marker Molecules in Aqueous Plant Extracts Affecting the Gold Nanostructures' Morphology and Size. Chemistry & biodiversity. 2023 Dec; ?(?):e202301349. doi: 10.1002/cbdv.202301349. [PMID: 38108659]
  • Fabiola Muro-Villanueva, Leonard D Pysh, Hoon Kim, Tyler Bouse, John Ralph, Zhiwei Luo, Bruce R Cooper, Amber S Jannasch, Zeyu Zhang, Chong Gu, Clint Chapple. Pinoresinol rescues developmental phenotypes of Arabidopsis phenylpropanoid mutants overexpressing FERULATE 5-HYDROXYLASE. Proceedings of the National Academy of Sciences of the United States of America. 2023 08; 120(31):e2216543120. doi: 10.1073/pnas.2216543120. [PMID: 37487096]
  • Meng-Ting Li, He-Jia Hu, Yang Jin, Yi Chen, Si-Ying Chen, Yue-Ting Li, Yong Huang, Lin Zheng, Jing Huang, Zi-Peng Gong. [Content determination of seven active components of Eucommiae Cortex in aortic vascular endothelial cells of spontaneously hypertensive rats by UPLC-MS/MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Jul; 48(13):3623-3632. doi: 10.19540/j.cnki.cjcmm.20230224.202. [PMID: 37474995]
  • Yakun Pei, Wenhan Cao, Wenwen Yu, Chaoyang Peng, Wenhao Xu, Yayun Zuo, Wenjun Wu, Zhaonong Hu. Identification and functional characterization of the dirigent gene family in Phryma leptostachya and the contribution of PlDIR1 in lignan biosynthesis. BMC plant biology. 2023 May; 23(1):291. doi: 10.1186/s12870-023-04297-6. [PMID: 37259047]
  • Niamh M O'Boyle, Ida B Niklasson, David J Ponting, Miguel A Ortega, Tina Seifert, Andreas Natsch, Kristina Luthman, Ann-Therese Karlberg. Nature-derived epoxy resins: Synthesis, allergenicity, and thermosetting properties of pinoresinol diglycidyl ether. Toxicology and industrial health. 2022 May; 38(5):259-269. doi: 10.1177/07482337221089595. [PMID: 35465773]
  • Ying Xiao, Kai Shao, Jingwen Zhou, Lian Wang, Xueqi Ma, Di Wu, Yingbo Yang, Junfeng Chen, Jingxian Feng, Shi Qiu, Zongyou Lv, Lei Zhang, Peng Zhang, Wansheng Chen. Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases. Nature communications. 2021 05; 12(1):2828. doi: 10.1038/s41467-021-23095-y. [PMID: 33990581]
  • Li Yang, Ronghua Liu, Yiwei Fang, Junwei He. Anti-inflammatory effect of phenylpropanoids from Dendropanax dentiger in TNF-α-induced MH7A cells via inhibition of NF-κB, Akt and JNK signaling pathways. International immunopharmacology. 2021 May; 94(?):107463. doi: 10.1016/j.intimp.2021.107463. [PMID: 33618295]
  • Davide Decembrino, Esther Ricklefs, Stefan Wohlgemuth, Marco Girhard, Katrin Schullehner, Guido Jach, Vlada B Urlacher. Assembly of Plant Enzymes in E. coli for the Production of the Valuable (-)-Podophyllotoxin Precursor (-)-Pluviatolide. ACS synthetic biology. 2020 11; 9(11):3091-3103. doi: 10.1021/acssynbio.0c00354. [PMID: 33095000]
  • Zsuzsanna Hajdú, Peter Forgo, Gergely Király, Gyula Pinke, István Zupkó, Judit Hohmann. Isolation of chemical constituents from Filago vulgaris and antiproliferative activity of the plant extract and its flavonoid against human tumor cell lines. Pakistan journal of pharmaceutical sciences. 2020 Jul; 33(4):1593-1597. doi: . [PMID: 33583792]
  • Madhura Shettigar, Sahil Balotra, Annette Kasprzak, Stephen L Pearce, Michael J Lacey, Matthew C Taylor, Jian-Wei Liu, David Cahill, John G Oakeshott, Gunjan Pandey. Oxidative Catabolism of (+)-Pinoresinol Is Initiated by an Unusual Flavocytochrome Encoded by Translationally Coupled Genes within a Cluster of (+)-Pinoresinol-Coinduced Genes in Pseudomonas sp. Strain SG-MS2. Applied and environmental microbiology. 2020 05; 86(10):. doi: 10.1128/aem.00375-20. [PMID: 32198167]
  • Hejia Hu, Linlin Wu, Mei Li, Cun Xue, Guangcheng Wang, Siying Chen, Yong Huang, Lin Zheng, Aimin Wang, Yueting Li, Zipeng Gong. Comparative absorption kinetics of seven active ingredients of Eucommia ulmoides extracts by intestinal in situ circulatory perfusion in normal and spontaneous hypertensive rats. Biomedical chromatography : BMC. 2020 Jan; 34(1):e4714. doi: 10.1002/bmc.4714. [PMID: 31633806]
  • Sun Young Kim, Joo Young Lee, Changho Jhin, Ji Min Shin, Myungsuk Kim, Hong Ruyl Ahn, Gyhye Yoo, Yang-Ju Son, Sang Hoon Jung, Chu Won Nho. Reduction of Hepatic Lipogenesis by Loliolide and Pinoresinol from Lysimachia vulgaris via Degrading Liver X Receptors. Journal of agricultural and food chemistry. 2019 Nov; 67(45):12419-12427. doi: 10.1021/acs.jafc.9b01488. [PMID: 31610126]
  • Ji-Won Choi, Joon Yeon Shin, Il-Joo Jo, Dong-Gu Kim, Ho-Joon Song, Chi-Su Yoon, Hyuncheol Oh, Youn-Chul Kim, Gi-Sang Bae, Sung-Joo Park. 8α-Hydroxypinoresinol isolated from Nardostachys jatamansi ameliorates cerulein-induced acute pancreatitis through inhibition of NF-κB activation. Molecular immunology. 2019 10; 114(?):620-628. doi: 10.1016/j.molimm.2019.09.002. [PMID: 31542607]
  • Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
  • So-Ra Lee, Khong Trong Quan, Hee Sun Byun, InWha Park, Kidong Kang, Xuezhe Piao, Eunjin Ju, Hyunju Ro, MinKyun Na, Gang Min Hur. Accelerated degradation of cFLIPL and sensitization of the TRAIL DISC-mediated apoptotic cascade by pinoresinol, a lignan isolated from Rubia philippinensis. Scientific reports. 2019 09; 9(1):13505. doi: 10.1038/s41598-019-49909-0. [PMID: 31534206]
  • Lucija Markulin, Cyrielle Corbin, Sullivan Renouard, Samantha Drouet, Laurent Gutierrez, Ivan Mateljak, Daniel Auguin, Christophe Hano, Elisabeth Fuss, Eric Lainé. Pinoresinol-lariciresinol reductases, key to the lignan synthesis in plants. Planta. 2019 Jun; 249(6):1695-1714. doi: 10.1007/s00425-019-03137-y. [PMID: 30895445]
  • Yingling Wu, Dawei Xing, Guoliang Ma, Xinlong Dai, Liping Gao, Tao Xia. A variable loop involved in the substrate selectivity of pinoresinol/lariciresinol reductase from Camellia sinensis. Phytochemistry. 2019 Jun; 162(?):1-9. doi: 10.1016/j.phytochem.2019.02.003. [PMID: 30844490]
  • Yang Ning, Yue Ling Fu, Qing Hua Zhang, Chun Zhang, Ying Chen. Inhibition of in vitro and in vivo ovarian cancer cell growth by pinoresinol occurs by way of inducing autophagy, inhibition of cell invasion, loss of mitochondrial membrane potential and inhibition Ras/MEK/ERK signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2019 Mar; 24(2):709-714. doi: . [PMID: 31128027]
  • Jing Li, Xiaoli Liang, Beixian Zhou, Xiaowei Chen, Peifang Xie, Haiming Jiang, Zhihong Jiang, Zifeng Yang, Xiping Pan. (+)‑pinoresinol‑O‑β‑D‑glucopyranoside from Eucommia ulmoides Oliver and its anti‑inflammatory and antiviral effects against influenza A (H1N1) virus infection. Molecular medicine reports. 2019 01; 19(1):563-572. doi: 10.3892/mmr.2018.9696. [PMID: 30483751]
  • Joséphine Ottavioli, Mathieu Paoli, Joseph Casanova, Félix Tomi, Ange Bighelli. Identification and Quantitative Determination of Resin Acids from Corsican Pinus pinaster Aiton Oleoresin Using 13 C-NMR Spectroscopy. Chemistry & biodiversity. 2019 Jan; 16(1):e1800482. doi: 10.1002/cbdv.201800482. [PMID: 30632681]
  • Nadiah Syafiqah Nor Azman, Md Shahadat Hossan, Veeranoot Nissapatorn, Chairat Uthaipibull, Parichat Prommana, Khoo Teng Jin, Mohammed Rahmatullah, Tooba Mahboob, Chandramathi Samudi Raju, Hassan Mahmood Jindal, Banasri Hazra, Mohd Ridzuan Mohd Abd Razak, Vijay Kumar Prajapati, Rajan Kumar Pandey, Norhaniza Aminudin, Khozirah Shaari, Nor Hadiani Ismail, Mark S Butler, Vladimir V Zarubaev, Christophe Wiart. Anti-infective activities of 11 plants species used in traditional medicine in Malaysia. Experimental parasitology. 2018 Nov; 194(?):67-78. doi: 10.1016/j.exppara.2018.09.020. [PMID: 30268422]
  • Taewoong Rho, Kee Dong Yoon. Application of off-line two-dimensional high-performance countercurrent chromatography on the chloroform-soluble extract of Cuscuta auralis seeds. Journal of separation science. 2018 May; 41(10):2169-2177. doi: 10.1002/jssc.201701498. [PMID: 29450982]
  • Madhura Shettigar, Sahil Balotra, David Cahill, Andrew C Warden, Michael J Lacey, Hans-Peter E Kohler, Daniel Rentsch, John G Oakeshott, Gunjan Pandey. Isolation of the (+)-Pinoresinol-Mineralizing Pseudomonas sp. Strain SG-MS2 and Elucidation of Its Catabolic Pathway. Applied and environmental microbiology. 2018 02; 84(4):. doi: 10.1128/aem.02531-17. [PMID: 29222099]
  • Xiaojian Gong, Qingxiang Luan, Xin Zhou, Yang Zhao, Chao Zhao. UHPLC-ESI-MS/MS determination and pharmacokinetics of pinoresinol glucoside and chlorogenic acid in rat plasma after oral administration of Eucommia ulmoides Oliv extract. Biomedical chromatography : BMC. 2017 Nov; 31(11):. doi: 10.1002/bmc.4008. [PMID: 28493441]
  • Eun Jin Mo, Jong Hoon Ahn, Yang Hee Jo, Seon Beom Kim, Bang Yeon Hwang, Mi Kyeong Lee. Inositol Derivatives and Phenolic Compounds from the Roots of Taraxacum coreanum. Molecules (Basel, Switzerland). 2017 Aug; 22(8):. doi: 10.3390/molecules22081349. [PMID: 28805750]
  • Anna Sólyomváry, Ágnes Alberti, András Darcsi, Rita Könye, Gergő Tóth, Béla Noszál, Ibolya Molnár-Perl, László Lorántfy, Judit Dobos, László Őrfi, Szabolcs Béni, Imre Boldizsár. Optimized conversion of antiproliferative lignans pinoresinol and epipinoresinol: Their simultaneous isolation and identification by centrifugal partition chromatography and high performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 May; 1052(?):142-149. doi: 10.1016/j.jchromb.2017.03.036. [PMID: 28384606]
  • Yun Zhu, Kayoko Kawaguchi, Ryoiti Kiyama. Differential and directional estrogenic signaling pathways induced by enterolignans and their precursors. PloS one. 2017; 12(2):e0171390. doi: 10.1371/journal.pone.0171390. [PMID: 28152041]
  • Jiaolin Bao, Ren-Bo Ding, Yeer Liang, Fang Liu, Kai Wang, Xuejing Jia, Chao Zhang, Meiwan Chen, Peng Li, Huanxing Su, Jian-Bo Wan, Yitao Wang, Chengwei He. Differences in Chemical Component and Anticancer Activity of Green and Ripe Forsythiae Fructus. The American journal of Chinese medicine. 2017; 45(7):1513-1536. doi: 10.1142/s0192415x17500823. [PMID: 28946767]
  • Qi Li, Yan Zhang, Jun-Ling Shi, Yi-Lin Wang, Hao-Bin Zhao, Dong-Yan Shao, Qing-Sheng Huang, Hui Yang, Ming-Liang Jin. Mechanism and Anticancer Activity of the Metabolites of an Endophytic Fungi from Eucommia ulmoides Oliv. Anti-cancer agents in medicinal chemistry. 2017; 17(7):982-989. doi: 10.2174/1871520616666160923094814. [PMID: 27671307]
  • Fadia S Youssef, Mohamed L Ashour, Mansour Sobeh, Hesham A El-Beshbishy, Abdel Nasser Singab, Michael Wink. Eremophila maculata-Isolation of a rare naturally-occurring lignan glycoside and the hepatoprotective activity of the leaf extract. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2016 Nov; 23(12):1484-1493. doi: 10.1016/j.phymed.2016.08.006. [PMID: 27765369]
  • Yongjun Li, Zipeng Gong, Xu Cao, Yonglin Wang, Aimin Wang, Lin Zheng, Yong Huang, Yanyu Lan. A UPLC-MS Method for Simultaneous Determination of Geniposidic Acid, Two Lignans and Phenolics in Rat Plasma and its Application to Pharmacokinetic Studies of Eucommia ulmoides Extract in Rats. European journal of drug metabolism and pharmacokinetics. 2016 Oct; 41(5):595-603. doi: 10.1007/s13318-015-0282-5. [PMID: 25990756]
  • Yan-xi Chang, Bao-quan Bao, Xuan Zhang, J I Rimubatu, Ping Zhang. [Chemical Constituents from A Taditional Mongolian Medicine Clematis aethusifolia]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jul; 39(7):1545-9. doi: . [PMID: 30203953]
  • Esther Ricklefs, Marco Girhard, Vlada B Urlacher. Three-steps in one-pot: whole-cell biocatalytic synthesis of enantiopure (+)- and (-)-pinoresinol via kinetic resolution. Microbial cell factories. 2016 May; 15(?):78. doi: 10.1186/s12934-016-0472-0. [PMID: 27160378]
  • Yue-ping Jiang, Yu-feng Liu, Qing-lan Guo, Cheng-bo Xu, Sheng Lin, Cheng-gen Zhu, Yong-chun Yang, Jian-gong Shi. [Lignanoids from an aqueous extract of the roots of Codonopsis pilosula]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 04; 51(4):616-25. doi: . [PMID: 29860746]
  • Nuoendagula, Naofumi Kamimura, Tetsuya Mori, Ryo Nakabayashi, Yukiko Tsuji, Shojiro Hishiyama, Kazuki Saito, Eiji Masai, Shinya Kajita. Expression and functional analyses of a putative phenylcoumaran benzylic ether reductase in Arabidopsis thaliana. Plant cell reports. 2016 Mar; 35(3):513-26. doi: 10.1007/s00299-015-1899-1. [PMID: 26601823]
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