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Isolation and identification of l / d -lactate-conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians

Three pairs of bufadienolide l / d -lactate epimers ( 16 ) were isolated from the eggs of the toad Bufo bufo gargarizans . The structures were elucidated by using spectroscopic methods, X-ray diffraction analysis and a modified Mosher's method. Compounds 16 represent the first occurrence of lactate-... Full description

Journal Title: Organic & Biomolecular Chemistry 2017, Vol.15(26), pp.5609-5615
Main Author: Zhou, Shiwen
Other Authors: Zheng, Qingfei , Huang, Xiuyong , Wang, Yong , Luo, Sifan , Jiang, Renwang , Wang, Lei , Ye, Wencai , Tian, Haiyan
Format: Electronic Article Electronic Article
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ID: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/c7ob01055a
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title: Isolation and identification of l / d -lactate-conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians
format: Article
creator:
  • Zhou, Shiwen
  • Zheng, Qingfei
  • Huang, Xiuyong
  • Wang, Yong
  • Luo, Sifan
  • Jiang, Renwang
  • Wang, Lei
  • Ye, Wencai
  • Tian, Haiyan
subjects:
  • Acyltransferase
  • Lactic Acid
  • Racemization
  • Enzymes
  • Cytotoxic Agents
  • X-Ray Diffraction
  • Gastric Cancer
  • Lactate Racemase
  • Eggs
  • Lung Cancer
  • Amphibia
  • Bufo Bufo Gargarizans
  • Food Biotechnology
ispartof: Organic & Biomolecular Chemistry, 2017, Vol.15(26), pp.5609-5615
description: Three pairs of bufadienolide l / d -lactate epimers ( 16 ) were isolated from the eggs of the toad Bufo bufo gargarizans . The structures were elucidated by using spectroscopic methods, X-ray diffraction analysis and a modified Mosher's method. Compounds 16 represent the first occurrence of lactate-conjugated bufadienolides in nature, and illustrate the existence of an enzyme-controlled epimerization from l - to d -lactate in amphibians. The biosynthetic pathways, in which two key enzymes might be involved ( i.e. , lactate racemase and acyltransferase), were proposed. In addition, the biological assays revealed that compounds 14 are potent cytotoxic agents against human gastric cancer cells BGC-823 and human lung cancer cells A549 with IC 50 values in a range of 8.0 to 80.0 nM.
language:
source:
identifier: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/c7ob01055a
fulltext: no_fulltext
issn:
  • 1477-0520
  • 1477-0539
  • 14770539
  • 14770520
url: Link


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titleIsolation and identification of l / d -lactate-conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians
creatorZhou, Shiwen ; Zheng, Qingfei ; Huang, Xiuyong ; Wang, Yong ; Luo, Sifan ; Jiang, Renwang ; Wang, Lei ; Ye, Wencai ; Tian, Haiyan
ispartofOrganic & Biomolecular Chemistry, 2017, Vol.15(26), pp.5609-5615
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descriptionThree pairs of bufadienolide l / d -lactate epimers ( 16 ) were isolated from the eggs of the toad Bufo bufo gargarizans . The structures were elucidated by using spectroscopic methods, X-ray diffraction analysis and a modified Mosher's method. Compounds 16 represent the first occurrence of lactate-conjugated bufadienolides in nature, and illustrate the existence of an enzyme-controlled epimerization from l - to d -lactate in amphibians. The biosynthetic pathways, in which two key enzymes might be involved ( i.e. , lactate racemase and acyltransferase), were proposed. In addition, the biological assays revealed that compounds 14 are potent cytotoxic agents against human gastric cancer cells BGC-823 and human lung cancer cells A549 with IC 50 values in a range of 8.0 to 80.0 nM.
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subjectAcyltransferase ; Lactic Acid ; Racemization ; Enzymes ; Cytotoxic Agents ; X-Ray Diffraction ; Gastric Cancer ; Lactate Racemase ; Eggs ; Lung Cancer ; Amphibia ; Bufo Bufo Gargarizans ; Food Biotechnology;
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titleIsolation and identification of l / d -lactate-conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians
descriptionThree pairs of bufadienolide l / d -lactate epimers ( 16 ) were isolated from the eggs of the toad Bufo bufo gargarizans . The structures were elucidated by using spectroscopic methods, X-ray diffraction analysis and a modified Mosher's method. Compounds 16 represent the first occurrence of lactate-conjugated bufadienolides in nature, and illustrate the existence of an enzyme-controlled epimerization from l - to d -lactate in amphibians. The biosynthetic pathways, in which two key enzymes might be involved ( i.e. , lactate racemase and acyltransferase), were proposed. In addition, the biological assays revealed that compounds 14 are potent cytotoxic agents against human gastric cancer cells BGC-823 and human lung cancer cells A549 with IC 50 values in a range of 8.0 to 80.0 nM.
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titleIsolation and identification of l / d -lactate-conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians
authorZhou, Shiwen ; Zheng, Qingfei ; Huang, Xiuyong ; Wang, Yong ; Luo, Sifan ; Jiang, Renwang ; Wang, Lei ; Ye, Wencai ; Tian, Haiyan
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abstractThree pairs of bufadienolide l / d -lactate epimers ( 16 ) were isolated from the eggs of the toad Bufo bufo gargarizans . The structures were elucidated by using spectroscopic methods, X-ray diffraction analysis and a modified Mosher's method. Compounds 16 represent the first occurrence of lactate-conjugated bufadienolides in nature, and illustrate the existence of an enzyme-controlled epimerization from l - to d -lactate in amphibians. The biosynthetic pathways, in which two key enzymes might be involved ( i.e. , lactate racemase and acyltransferase), were proposed. In addition, the biological assays revealed that compounds 14 are potent cytotoxic agents against human gastric cancer cells BGC-823 and human lung cancer cells A549 with IC 50 values in a range of 8.0 to 80.0 nM.
doi10.1039/c7ob01055a
pages5609-5615
date2017-07-05