Preparation of 1,2,3,4,6-penta-O-galloyl-[U-14C]-D-glucopyranose

被引：12

作者：

Chen, YM ^{[1
]}

Hagerman, AE ^{[1
]}

Minto, RE ^{[1
]}

机构：

[1] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2003年 / 46卷 / 01期

关键词：

hydrolyzable tannin; polyphenol; antioxidant; pentagalloylglucose;

D O I：

10.1002/jlcr.648

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of 1,2,3,4,6-penta-O-galloyl-[U-C-14]-D-glucopyranose is described. [U-C-14]glucopyranose was reacted with tri-O-benzylgallic acid forming 1;2,3,4,6-penta(tri-O-benzylgalloyl)-[U-C-14]-D-glucopyranose as chromatograpically separable anomers. Removal of the benzyl group by catalytic hydrogenation afforded 1,2,3,4,6-penta-O-galloyl-[U-C-14]-D-glucopyranose in 54% overall yield. GRAPHICS. Copyright (C) 2002 John Wiley Sons, Ltd.

引用

页码：99 / 105

页数：7

共 29 条

[1] 1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose: Its Anti-Inflammatory and Antibacterial Properties
Bobrowska, Diana M.
Czyrko, Justyna
Eljaszewicz, Andrzej
Grubczak, Kamil
Wlodarczyk, Anna J.
Moniuszko, Marcin
Brzezinski, Krzysztof
Plonska-Brzezinska, Marta E.
CHEMISTRYSELECT, 2018, 3 (09): : 2498 - 2501
[2] Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose, castalagin, and grandinin
Hofmann, Thomas
Glabasnia, Arne
Schwarz, Bernd
Wisman, Kimberly N.
Gangwer, Kelly A.
Hagerman, Ann E.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (25) : 9503 - 9509
[3] 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose binds to the N-terminal metal binding region to inhibit amyloid β-protein oligomer and fibril formation
de Almeida, Natalia E. C.
Do, Thanh D.
LaPointe, Nichole E.
Tro, Michael
Feinstein, Stuart C.
Shea, Joan-Emma
Bowers, Michael T.
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2017, 420 : 24 - 34
[4] 1,2,3,4,6-penta-O-galloyl-β-D-glucose: A cholinesterase inhibitor from Terminalia chebula
Sancheti, S.
Sancheti, S.
Um, B. -H.
Seo, S. -Y
SOUTH AFRICAN JOURNAL OF BOTANY, 2010, 76 (02) : 285 - 288
[5] Antioxidant properties of 1,2,3,4,6-penta-O-galloyl-β-D-glucose from Elaeocarpus sylvestris var. ellipticus
Piao, Mei Jing
Kang, Kyoung Ah
Zhang, Rui
Ko, Dong Ok
Wang, Zhi Hong
Lee, Keun Hwa
Chang, Weon Young
Chae, Sungwook
Jee, Youngheun
Shin, Taekyun
Park, Jae Woo
Lee, Nam Ho
Hyun, Jin Won
FOOD CHEMISTRY, 2009, 115 (02) : 412 - 418
[6] Effects of Metal Ions on the Precipitation of Penta-O-galloyl-β-D-glucopyranose by Protein
Zhang, He
Zhang, Liangliang
Tang, Lihua
Hu, Xinyu
Xu, Man
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2021, 69 (17) : 5059 - 5066
[7] Antioxidant 1,2,3,4,6-Penta-O-galloyl-β-D-glucose Alleviating Apoptosis and Promoting Bone Formation Is Associated with Estrogen Receptors
Hua, Yongqing
Wang, Haili
Chen, Tingting
Zhou, Yeru
Chen, Zhiyuan
Zhao, Xinyue
Mo, Shaoqin
Mao, Hongyun
Li, Miao
Wang, Linxia
Hong, Min
MOLECULES, 2024, 29 (21):
[8] EFFECT OF 1,2,3,4,6-PENTA-O-GALLOYL-β-D-GLUCOSE ON ELASTASE AND HYALURONIDASE ACTIVITIES AND ITS TYPE II COLLAGEN EXPRESSION
Kim, Song-Ja
Sancheti, Sandesh A.
Sancheti, Shruti S.
Um, Byung-Hun
Yu, Seon-Mi
Seo, Sung-Yum
ACTA POLONIAE PHARMACEUTICA, 2010, 67 (02): : 145 - 150
[9] 1,2,3,4,6-Penta-O-galloyl-β-D-glucose, a bioactive compound in Elaeocarpus sylvestris extract, inhibits varicella-zoster virus replication
Bae, Sohee
Kim, Sun Yeou
Do, Moon Ho
Lee, Chan Hee
Song, Yoon-Jae
ANTIVIRAL RESEARCH, 2017, 144 : 266 - 272
[10] Characterization of soluble non-covalent complexes between bovine serum albumin and β-1,2,3,4,6-penta-O-galloyl-D-glucopyranose by MALDI-TOF MS
Chen, YM
Hagerman, AE
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (12) : 4008 - 4011

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