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4-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata
  • ISSN号:1006-687X
  • 期刊名称:《应用与环境生物学报》
  • 时间:0
  • 分类:R284[医药卫生—中药学;医药卫生—中医学]
  • 作者机构:State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College
  • 相关基金:the National Natural Science Foundation of China (NNSFC; Nos. 30825044 and 20932007);the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT, No. IRT1007);the National Science and Technology Project of China (Nos. 2012ZX09301002-002 and 2011ZX09307002-01) is acknowledged
中文摘要:

Seven new 4-hydroxybenzyl-substituted amino acid derivatives(1-7), together with 11 known compounds, were isolated from an aqueous extract of the rhizomes of Gastrodia elata Blume.Their structures were determined by spectroscopic and chemical methods. Compounds 1-3 are pyroglutamate derivatives containing 4-hydroxybenzyl units at the N atom and 4-7 are the first examples of natural products with the 4-hydroxybenzyl unit linked via a thioether bond to 2-hydroxy-3-mercaptopropanoic acid(4-6) and 2-hydroxy-4-mercaptobutanoic acid(7), which would be biogenetically derived from cysteine and homocysteine, respectively. The structures of 1 and 2 were verified by synthesis, while the absolute configurations of 4, 5 and 7 were assigned using Mosher’s method based on the MPA determination rule of ΔδRS values. The known compound 4-(hydroxymethyl)-5-nitrobenzene-1,2-diol(8) exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation with IC50 values of 9.99×10-6 mol/L.

英文摘要:

Seven new 4-hydroxyben l-substituted amino acid derivatives (1-7), together with 11 known compounds, were isolated from an aqueous extract of the rhizomes of Go,arodia data Blume. Their structures were determined by spectroscopic and chemical methods. Compounds 1-3 are pyroglutamate derivatives containing 4-hydroxybenzyl units at the N atom and 4-7 are the first examples of natural products with the 4-hydroxybenzyl unit linked vici a thioether bond to 2-hydroxy-3mercaptopropanoic acid (4-6) and 2-hydroxy-4-mercaptobutanoic acid (7), which would be biogenetically derived from cysteine and homocysteine, respectively. The structures of 1 and 2 were verified hi synthesis, while the absolute configurations of 4, 5 and 7 were assigned using Mosher 's method based on the MPA determination rule of A5Rs values. The known compound 4-(hydroxymethy0-5-nifrobenzene1,2-diol (8) exhibited activity against Fe2 r--cysteine induced rat liver microsomal lipid peroxidation with 1050 values of 9.99 x 10 6 mon. (C) 2015 Chinese Pharmaceutical Association and Institute of Materia Medica, Chinese Academy of Medical Sciences. Production and hosting by Elsevier B.'s/. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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期刊信息
  • 《应用与环境生物学报》
  • 北大核心期刊(2011版)
  • 主管单位:中国科学院
  • 主办单位:中国科学院成都生物研究所
  • 主编:吴宁
  • 地址:成都市人民南路4段9号
  • 邮编:610041
  • 邮箱:biojaeb@cib.ac.cn
  • 电话:028-82890917
  • 国际标准刊号:ISSN:1006-687X
  • 国内统一刊号:ISSN:51-1482/Q
  • 邮发代号:62-15
  • 获奖情况:
  • 中国农业期刊金犁奖学术类一等奖(2006),* 中国期刊方阵双效期刊(2002年),* 四川省第二届优秀期刊(2000年),* 四川省一级学术期刊(1998年)
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘(网络版),荷兰文摘与引文数据库,美国生物科学数据库,英国动物学记录,日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊(2004版),中国北大核心期刊(2008版),中国北大核心期刊(2011版),中国北大核心期刊(2014版)
  • 被引量:23016