Literature DB >> 20970943

Preparation of penta-O-galloyl-β-D-glucose from tannic acid and plasma pharmacokinetic analyses by liquid-liquid extraction and reverse-phase HPLC.

Li Li1, Ahmad Ali Shaik, Jinhui Zhang, Katai Nhkata, Lei Wang, Yong Zhang, Chengguo Xing, Sung-Hoon Kim, Junxuan Lü.   

Abstract

The gallotannin penta-O-galloyl-beta-D-glucose (PGG) has many biological activities including in vivo anti-cancer efficacy. We present in this paper a scaled-up protocol for its preparation in high purity from tannic acid by acidic methanolysis with typical yield of 15%. We also describe a method for the analysis of PGG in mouse plasma by HPLC and its application in preliminary pharmacokinetic studies. A liquid-liquid extraction (LLE) protocol was optimized for the extraction of PGG from mouse plasma. The extraction efficiency for PGG at 1 μg/mL in mouse plasma was 70.0±1.3% (n=5). The limit of detection (LOD) for PGG was approximately 0.2 μg/mL. Preliminary pharmacokinetic parameters of PGG following a single i.p. injection with 5% ethanol/saline vehicle in mice were established. The peak plasma PGG concentrations (C(max)) were approximately 3-4 μM at a dose of 0.5 mg per mouse (∼20 mg/kg) at 2 h post-injection (T(max)).
Copyright © 2010 Elsevier B.V. All rights reserved.

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Year:  2010        PMID: 20970943      PMCID: PMC2981694          DOI: 10.1016/j.jpba.2010.09.028

Source DB:  PubMed          Journal:  J Pharm Biomed Anal        ISSN: 0731-7085            Impact factor:   3.571


  16 in total

1.  Determination of hydrolyzable tannins (gallotannins and ellagitannins) after reaction with potassium iodate.

Authors:  Paul W Hartzfeld; Rebecca Forkner; Mark D Hunter; Ann E Hagerman
Journal:  J Agric Food Chem       Date:  2002-03-27       Impact factor: 5.279

2.  Liquid chromatography with multi-channel electrochemical detection for the determination of epigallocatechin gallate in rat plasma utilizing an automated blood sampling device.

Authors:  H Long; Y Zhu; M Cregor; F Tian; L Coury; C B Kissinger; P T Kissinger
Journal:  J Chromatogr B Biomed Sci Appl       Date:  2001-11-05

Review 3.  Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies.

Authors:  Claudine Manach; Gary Williamson; Christine Morand; Augustin Scalbert; Christian Rémésy
Journal:  Am J Clin Nutr       Date:  2005-01       Impact factor: 7.045

4.  Penta-O-galloyl-beta-D-glucose suppresses prostate cancer bone metastasis by transcriptionally repressing EGF-induced MMP-9 expression.

Authors:  Po-Tsun Kuo; Tsung-Pang Lin; Liang-Chih Liu; Chi-Hung Huang; Jen-Kun Lin; Jung-Yie Kao; Tzong-Der Way
Journal:  J Agric Food Chem       Date:  2009-04-22       Impact factor: 5.279

5.  Temporal stability of the urinary proteome after kidney transplant: more sensitive than protein composition?

Authors:  Sanjeev K Akkina; Yan Zhang; Gary L Nelsestuen; William S Oetting; Hassan N Ibrahlm
Journal:  J Proteome Res       Date:  2009-01       Impact factor: 4.466

6.  Analysis of plasma and urinary tea polyphenols in human subjects.

Authors:  M J Lee; Z Y Wang; H Li; L Chen; Y Sun; S Gobbo; D A Balentine; C S Yang
Journal:  Cancer Epidemiol Biomarkers Prev       Date:  1995-06       Impact factor: 4.254

7.  Penta-O-galloyl-beta-D-glucose suppresses tumor growth via inhibition of angiogenesis and stimulation of apoptosis: roles of cyclooxygenase-2 and mitogen-activated protein kinase pathways.

Authors:  Jeong-Eun Huh; Eun-Ok Lee; Min-Seok Kim; Kyung-Sun Kang; Cheol-Ho Kim; Bae-Cheon Cha; Young-Joon Surh; Sung-Hoon Kim
Journal:  Carcinogenesis       Date:  2005-04-21       Impact factor: 4.741

8.  In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus.

Authors:  Sung-Jin Lee; Hak-Kyo Lee; Min-Kyung Jung; Woongchon Mar
Journal:  Biol Pharm Bull       Date:  2006-10       Impact factor: 2.264

9.  In vitro anti-proliferative effect of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose on human hepatocellular carcinoma cell line, SK-HEP-1 cells.

Authors:  G S Oh; H O Pae; H Oh; S G Hong; I K Kim; K Y Chai; Y G Yun; T O Kwon; H T Chung
Journal:  Cancer Lett       Date:  2001-12-10       Impact factor: 9.756

10.  Penta-1,2,3,4,6-O-galloyl-beta-D-glucose induces p53 and inhibits STAT3 in prostate cancer cells in vitro and suppresses prostate xenograft tumor growth in vivo.

Authors:  Hongbo Hu; Hyo-Jeong Lee; Cheng Jiang; Jinhui Zhang; Lei Wang; Yan Zhao; Qiu Xiang; Eun-Ok Lee; Sung-Hoon Kim; Junxuan Lü
Journal:  Mol Cancer Ther       Date:  2008-09       Impact factor: 6.009

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  10 in total

1.  Stability of Polyphenols Epigallocatechin Gallate and Pentagalloyl Glucose in a Simulated Digestive System.

Authors:  Melanie A Krook; Ann E Hagerman
Journal:  Food Res Int       Date:  2012-08-04       Impact factor: 6.475

2.  Oral administration of penta-O-galloyl-β-D-glucose suppresses triple-negative breast cancer xenograft growth and metastasis in strong association with JAK1-STAT3 inhibition.

Authors:  Hyo-Jeong Lee; Nam-Jun Seo; Soo-Jin Jeong; Yongjin Park; Deok-Beom Jung; Wonil Koh; Hyo-Jung Lee; Eun-Ok Lee; Kwang Seok Ahn; Kyoo Seok Ahn; Junxuan Lü; Sung-Hoon Kim
Journal:  Carcinogenesis       Date:  2011-02-02       Impact factor: 4.741

3.  Involvement of autophagy induction in penta-1,2,3,4,6-O-galloyl-β-D-glucose-induced senescence-like growth arrest in human cancer cells.

Authors:  Yinhui Dong; Shutao Yin; Cheng Jiang; Xiaohe Luo; Xiao Guo; Chong Zhao; Lihong Fan; Yubing Meng; Junxuan Lu; Xinhua Song; Xudong Zhang; Ni Chen; Hongbo Hu
Journal:  Autophagy       Date:  2013-12-18       Impact factor: 13.391

4.  Tannic acid, a higher galloylated pentagalloylglucose, suppresses antigen-specific IgE production by inhibiting ɛ germline transcription induced by STAT6 activation.

Authors:  Yoon Hee Kim; Miki Yoshimoto; Kazuko Nakayama; Sousuke Tanino; Yoshinori Fujimura; Koji Yamada; Hirofumi Tachibana
Journal:  FEBS Open Bio       Date:  2013-08-05       Impact factor: 2.693

5.  The synthesis and antitumor activity of twelve galloyl glucosides.

Authors:  Chang-Wei Li; Hua-Jin Dong; Cheng-Bin Cui
Journal:  Molecules       Date:  2015-01-27       Impact factor: 4.411

6.  Comparison of Antioxidant Properties of Evening Primrose Seeds by Different Processing Methods, and Physiological Properties of Evening Primrose Seed Powder.

Authors:  Song Min Lee; Hee Sook Kim; Hye-Jung Park; Ka-Yoon Oh; Ji-Youn Kim; Sang-Hyeon Lee; Jeong Su Jang; Mun Hyon Lee
Journal:  Prev Nutr Food Sci       Date:  2020-12-31

7.  Investigation of the inhibition effect of 1,2,3,4,6-pentagalloyl-β-D-glucose on gastric cancer cells based on a network pharmacology approach and experimental validation.

Authors:  Jing-Hui Bi; Yu-Han Jiang; Shi-Jie Ye; Min-Rui Wu; Yang Yi; Hong-Xun Wang; Li-Mei Wang
Journal:  Front Oncol       Date:  2022-08-03       Impact factor: 5.738

8.  1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.

Authors:  Lorna M Cryan; Lauren Bazinet; Kaiane A Habeshian; Shugeng Cao; Jon Clardy; Kenneth A Christensen; Michael S Rogers
Journal:  J Med Chem       Date:  2013-02-22       Impact factor: 8.039

9.  Pentagalloylglucose, isolated from the leaf extract of Anacardium occidentale L., could elicit rapid and selective cytotoxicity in cancer cells.

Authors:  Bamigboye J Taiwo; Temidayo D Popoola; Fanie R van Heerden; Amos A Fatokun
Journal:  BMC Complement Med Ther       Date:  2020-09-21

10.  Factors Influencing Oral Bioavailability of Thai Mango Seed Kernel Extract and Its Key Phenolic Principles.

Authors:  Pimsumon Jiamboonsri; Pimolpan Pithayanukul; Rapepol Bavovada; Jiraporn Leanpolchareanchai; Taijun Yin; Song Gao; Ming Hu
Journal:  Molecules       Date:  2015-11-30       Impact factor: 4.927

  10 in total

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