Advanced search
Publication Cover
Bioscience, Biotechnology, and Biochemistry Volume 78, 2014 - Issue 7
Journal homepage
1,878
Views
38
CrossRef citations to date
0
Altmetric
Organic Chemistry

Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities

Daisuke SatoFaculty of Medicine, Department of Chemistry, Oita University, Oita, Japan
,
Nobuyoshi ShimizuAdvanced Research Center for Genome Super Power, Keio University, Tsukuba, Japan
,
Yoshiko ShimizuAdvanced Research Center for Genome Super Power, Keio University, Tsukuba, Japan
,
Masaaki AkagiFaculty of Pharmaceutical Sciences, Department of Pharmacology, Tokushima Bunri University, Tokushima, Japan
,
Yuki EshitaFaculty of Medicine, Department of Infectious Disease Control, Oita University, Oita, Japan
,
Shin-ichi OzakiFaculty of Agriculture, Department of Biological Sciences, Yamaguchi University, Yamaguchi, Japan
,
Nobuyoshi NakajimaIndustry, Government, and Academic Promotional Center, Regional Cooperative Research Organization, Okayama Prefectural University, Soja, Japan
,
Kohji IshiharaFaculty of Science, Department of Life Science, Okayama University of Science, Okayama, Japan
,
Noriyoshi MasuokaFaculty of Science, Department of Life Science, Okayama University of Science, Okayama, Japan
,
Hiroki HamadaFaculty of Science, Department of Life Science, Okayama University of Science, Okayama, JapanCorrespondence[email protected] [email protected]
,
Kei ShimodaFaculty of Medicine, Department of Chemistry, Oita University, Oita, JapanCorrespondence[email protected] [email protected]
&
Naoji KubotaFaculty of Medicine, Department of Chemistry, Oita University, Oita, Japan
 show all
Pages 1123-1128 | Received 14 Nov 2013, Accepted 28 Feb 2014, Published online: 09 Jun 2014

Citations (38)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (2)

Daisuke Uesugi, Hiroki Hamada, Kei Shimoda, Naoji Kubota, Shin-ichi Ozaki & Naoki Nagatani. (2017) Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene. Bioscience, Biotechnology, and Biochemistry 81:2, pages 226-230.
Read now
Lijuan Xu, Tingting Qi, Li Xu, Lili Lu & Min Xiao. (2016) Recent progress in the enzymatic glycosylation of phenolic compounds. Journal of Carbohydrate Chemistry 35:1, pages 1-23.
Read now

Articles from other publishers (36)

Lianghao Huang, Jinyu Wang, Xiaoyao Ma, Lishan Sun, Cui Hao & Wei Wang. (2023) Inhibition of influenza a virus infection by natural stilbene piceatannol targeting virus hemagglutinin. Phytomedicine 120, pages 155058.
Crossref
Mazharul Maishan, Andrew Stuart, Kurt Bachmaier, Shotaro Matsumoto, Hiroki Taenaka, Abhalaxmi Singh, Patricia Bucko, Li Wang, Lindsay R. Vivona, Wolfgang M. Kuebler, Jalees Rehman, Asrar B. Malik & Michael A. Matthay. (2023) Engineered Albumin Nanoparticles Targeting Inflammatory Neutrophils in Human Lungs Mitigate Endotoxemia-Induced Lung Injury. ACS Applied Nano Materials.
Crossref
A. Gorga, G.M. Rindone, M.E. Dasso, C.L. Centola, E.H. Pellizzari, M.C. Camberos, J. Toneatto, M.F. Riera, M.N. Galardo & S.B. Meroni. (2023) Simultaneous regulation of lactate production and fatty acid metabolism by Resveratrol in rat Sertoli cells. Biochimie 208, pages 75-85.
Crossref
Guizhen Wang, Hongtao Liu, Yawen Gao, Xiaodi Niu, Xuming Deng, Jianfeng Wang, Haihua Feng, Zhimin Guo & Jiazhang Qiu. (2022) Piceatannol Alleviates Clostridium perfringens Virulence by Inhibiting Perfringolysin O. Molecules 27:16, pages 5145.
Crossref
Nattawadee Lorthongpanich, Panupong Mahalapbutr, Thanyada Rungrotmongkol, Thanapon Charoenwongpaiboon & Manchumas Hengsakul Prousoontorn. (2022) Fisetin glycosides synthesized by cyclodextrin glycosyltransferase from Paenibacillus sp. RB01: characterization, molecular docking, and antioxidant activity . PeerJ 10, pages e13467.
Crossref
Chang Hyung Lee, Hee Yang, Jung Han Yoon Park, Jong-Eun Kim & Ki Won Lee. (2022) Piceatannol, a metabolite of resveratrol, attenuates atopic dermatitis by targeting Janus kinase 1. Phytomedicine 99, pages 153981.
Crossref
Ram Krishna Sahu, Ved Vrat Verma, Amit Kumar, Simran Tandon, Bhudev Chandra Das & Suresh T. Hedau. (2022) In silico prediction and interaction of resveratrol on methyl-CpG binding proteins by molecular docking and MD simulations study . RSC Advances 12:18, pages 11493-11504.
Crossref
Monika Bielecka, Bartosz Pencakowski & Rosario Nicoletti. (2022) Using Next-Generation Sequencing Technology to Explore Genetic Pathways in Endophytic Fungi in the Syntheses of Plant Bioactive Metabolites. Agriculture 12:2, pages 187.
Crossref
Chengyuan Liang, Juan Li, Bin Tian, Lei Tian, Yuzhi Liu, Jingyi Li, Liang Xin, Jun Wang, Chao Fu, Zhenfeng Shi, Juan Xia, Yiting Liang & Kun Wang. (2021) Foresight regarding drug candidates acting on the succinate–GPR91 signalling pathway for non-alcoholic steatohepatitis (NASH) treatment. Biomedicine & Pharmacotherapy 144, pages 112298.
Crossref
Lingfeng Wang, Ying Guo, Jiayi Ye, Zeyue Pan, Peihao Hu, Xiaoming Zhong, Fengmei Qiu, Danni Zhang & Zhen Huang. (2021) Protective Effect of Piceatannol Against Cerebral Ischaemia–Reperfusion Injury Via Regulating Nrf2/HO-1 Pathway In Vivo and Vitro. Neurochemical Research 46:7, pages 1869-1880.
Crossref
Ryusuke Hosoda, Hiroki Hamada, Daisuke Uesugi, Naotoshi Iwahara, Iyori Nojima, Yoshiyuki Horio & Atsushi Kuno. (2021) Different Antioxidative and Antiapoptotic Effects of Piceatannol and Resveratrol. Journal of Pharmacology and Experimental Therapeutics 376:3, pages 385-396.
Crossref
Yue Fan, Si-Lin Huang, Hong Li, Yu-Lin Cui & Dong-yan Li. (2021) Resveratrol attenuates inflammation by regulating macrophage polarization via inhibition of toll-like receptor 4/MyD88 signaling pathway. Pharmacognosy Magazine 17:74, pages 321.
Crossref
Yuya Fujitaka, Hiroki Hamada, Hatsuyuki Hamada, Kohji Ishihara, Takafumi Iwaki, Kei Shimoda, Yuya Kiriake & Tomohiro Saikawa. (2021) Synthesis of Ester-Linked Paclitaxel–Glycoside Conjugate and Its Drug Delivery System Using Hybrid-Bio-Nanocapsules Targeted With Trastuzumab. Natural Product Communications 16:1, pages 1934578X2095365.
Crossref
Yuya Fujitaka, Hiroki Hamada, Hatsuyuki Hamada, Takafumi Iwaki, Kei Shimoda, Yuya Kiriake & Tomohiro Saikawa. (2020) Synthesis of Glycosides of α-Tocopherol, Daidzein, Resveratrol, Hesperetin, Naringenin, and Chrysin as Antiallergic Functional Foods and Cosmetics. Natural Product Communications 15:9, pages 1934578X2094466.
Crossref
Jinhu Ma, Yongheng Cao, Liangliang Sun, Ying Li, Qiong Ju, Xiaohuan Yang & Jin Xu. (2020) Methyl 3-(4-hydroxyphenyl) propionate modulates plant growth and secondary metabolite accumulation by inducing metabolic changes in Perilla frutescens. Plant and Soil 453:1-2, pages 577-593.
Crossref
Kei Shimoda, Naoji Kubota, Daisuke Uesugi, Yusuke Kobayashi, Hatsuyuki Hamada & Hiroki Hamada. (2020) Glycosylation of Stilbene Compounds by Cultured Plant Cells. Molecules 25:6, pages 1437.
Crossref
Chongyang Wang, Liangchang Li, Jingzhi Jiang, Li Li, Junfeng Li, Chang Xu, Shan Jin, Lianhua Zhu & Guanghai Yan. (2020) Pterostilbene Inhibits FcεRI Signaling through Activation of the LKB1/AMPK Pathway in Allergic Response. Journal of Agricultural and Food Chemistry 68:11, pages 3456-3465.
Crossref
Yao Lu, Chao Ye, Jinxin Che, Xiaoguang Xu, Dongyan Shao, Chunmei Jiang, Yanlin Liu & Junling Shi. (2019) Genomic sequencing, genome-scale metabolic network reconstruction, and in silico flux analysis of the grape endophytic fungus Alternaria sp. MG1. Microbial Cell Factories 18:1.
Crossref
Yuya Fujitaka, Hiroki Hamada, Daisuke Uesugi, Atsuhito Kuboki, Kei Shimoda, Takafumi Iwaki, Yuya Kiriake & Tomohiro Saikawa. (2019) Synthesis of Daidzein Glycosides, α-Tocopherol Glycosides, Hesperetin Glycosides by Bioconversion and Their Potential for Anti-Allergic Functional-Foods and Cosmetics. Molecules 24:16, pages 2975.
Crossref
Xiaohui Zhao, Jihong Tao, Ting Zhang, Sirong Jiang, Wei Wei, Hongping Han, Yun Shao, Guoyin Zhou & Huilan Yue. (2019) Resveratroloside Alleviates Postprandial Hyperglycemia in Diabetic Mice by Competitively Inhibiting α-Glucosidase. Journal of Agricultural and Food Chemistry 67:10, pages 2886-2893.
Crossref
Zhenxian Zhang, Hiroki Hamada & Phillip M. Gerk. (2019) Selectivity of Dietary Phenolics for Inhibition of Human Monoamine Oxidases A and B. BioMed Research International 2019, pages 1-12.
Crossref
Jeongmin Park, Yingqing Chen, Min Zheng, Jinhyun Ryu, Gyeong Jae Cho, Young-Joon Surh, Daisuke Sato, Hiroki Hamada, Stefan W. Ryter, Uh-Hyun Kim, Yeonsoo Joe & Hun Taeg Chung. (2018) Pterostilbene 4 - β -Glucoside Attenuates LPS-Induced Acute Lung Injury via Induction of Heme Oxygenase-1 . Oxidative Medicine and Cellular Longevity 2018, pages 1-16.
Crossref
Tava Shelan NagapanAhmad Rohi GhazaliDayang Fredalina Basri & Wenna Nallance Lim. (2018) Photoprotective Effect Of Stilbenes And Its Derivatives against Ultraviolet Radiation-Induced Skin Disorders. Biomedical and Pharmacology Journal 11:3, pages 1199-1208.
Crossref
Hiroki Hamada, Shouta Okada, Noriyoshi Masuoka, Hatsuyuki Hamada, Kei Shimoda, Katsuhiko Mikuni & Yuya Fujitaka. (2018) Synthesis of Ester-linked Taxol-glycoside Conjugate and Its Application to Drug Delivery System Using Immunoliposome Targeted with Trastuzumab and Cetuximab. Natural Product Communications 13:7, pages 1934578X1801300.
Crossref
José González-Alfonso, David Rodrigo-Frutos, Efres Belmonte-Reche, Pablo Peñalver, Ana Poveda, Jesús Jiménez-Barbero, Antonio Ballesteros, Yoshihiko Hirose, Julio Polaina, Juan Morales, María Fernández-Lobato & Francisco Plou. (2018) Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase. Molecules 23:6, pages 1271.
Crossref
Bo Fan, Wenxin Dong, Tianyi Chen, Jianlin Chu & Bingfang He. (2018) Switching glycosyltransferase UGT BL 1 regioselectivity toward polydatin synthesis using a semi-rational design . Organic & Biomolecular Chemistry 16:14, pages 2464-2469.
Crossref
Ibrahim Khalifa, Wei Zhu, Kai-kai Li & Chun-mei Li. (2018) Polyphenols of mulberry fruits as multifaceted compounds: Compositions, metabolism, health benefits, and stability—A structural review. Journal of Functional Foods 40, pages 28-43.
Crossref
Catarina Dias, Ana M. Matos & Amélia P. Rauter. 2018. Coupling and Decoupling of Diverse Molecular Units in Glycosciences. Coupling and Decoupling of Diverse Molecular Units in Glycosciences 167 194 .
Thien-Kim Le, Hyun-Hee Jang, Ha Thi Huong Nguyen, Tiep Thi My Doan, Ga-Young Lee, Ki Deok Park, Taeho Ahn, Young Hee Joung, Hyung-Sik Kang & Chul-Ho Yun. (2017) Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3. Enzyme and Microbial Technology 97, pages 34-42.
Crossref
Hiroki Hamada, Kei Shimoda, Yoshiyuki Horio, Tsubasa Ono, Ryusuke Hosoda, Noriyuki Nakayama & Koichi Urano. (2017) Pterostilbene and Its Glucoside Induce Type XVII Collagen Expression. Natural Product Communications 12:1, pages 1934578X1701200.
Crossref
Yingqing Chen, Jeongmin Park, Yeonsoo Joe, Hyeok-Jun Park, Seung-Joo Jekal, Daisuke Sato, Hiroki Hamada & Hun Taeg Chung. (2017) Pterostilbene 4′- β -Glucoside Protects against DSS-Induced Colitis via Induction of Tristetraprolin . Oxidative Medicine and Cellular Longevity 2017, pages 1-10.
Crossref
Young-Joon Surh & Hye-Kyung Na. 2016. Anti-inflammatory Nutraceuticals and Chronic Diseases. Anti-inflammatory Nutraceuticals and Chronic Diseases 185 211 .
Qing Jin, Jiufang Yang, Liyan Ma, Jieling Cai & Jingming Li. (2015) Comparison of Polyphenol Profile and Inhibitory Activities Against Oxidation and α-Glucosidase in Mulberry (Genus Morus ) Cultivars from China . Journal of Food Science 80:11, pages C2440-C2451.
Crossref
Kei Shimoda, Naoji Kubota, Daisuke Uesugi, Hatsuyuki Hamada, Masato Tanigawa & Hiroki Hamada. (2015) Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol. Annals of the New York Academy of Sciences 1348:1, pages 141-149.
Crossref
Yu Zhou, Xue-mei Zhang, Ang Ma, Ya-li Zhang, Yan-yi Chen, Hao Zhou, Wen-jun Li & Xin Jin. (2015) Orally administrated pterostilbene attenuates acute cerebral ischemia–reperfusion injury in a dose- and time-dependent manner in mice. Pharmacology Biochemistry and Behavior 135, pages 199-209.
Crossref
Guohua Han, Jufeng Xia, Jianjun Gao, Yoshinori Inagaki, Wei Tang & Norihiro Kokudo. (2015) Anti-tumor effects and cellular mechanisms of resveratrol. Drug Discoveries & Therapeutics 9:1, pages 1-12.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.