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Prenylated C6–C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity.

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Title: Prenylated C6–C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity.
Authors: Zhang, Jian-Pei1 (AUTHOR), Li, Wen-Rui1 (AUTHOR), Wu, Shuo2 (AUTHOR), Wang, Xiao-Jing1 (AUTHOR), Wang, Ru-Bing1 (AUTHOR), Li, Mi1 (AUTHOR), Su, Guo-Zhu1 (AUTHOR), Wang, Hai-Qiang1 (AUTHOR), Yong, Jin-Yao1 (AUTHOR), Yang, Jia1 (AUTHOR), Li, Li1 (AUTHOR), Li, Yu-Huan1,2 (AUTHOR) yuhuanlibj@126.com, Ma, Shuang-Gang1 (AUTHOR) mashuanggang@imm.ac.cn
Source: Phytochemistry. Dec2021, Vol. 192, pN.PAG-N.PAG. 1p.
Subjects: Influenza A virus, Influenza viruses, Coxsackieviruses, X-ray crystallography
Abstract: Thirteen compounds were isolated from the lipid-soluble extracts of Illicium ternstroemioides A. C. Smith, including eleven previously undescribed prenylated C 6 –C 3 compounds, a previously undescribed prenylated C 6 –C 3 derivative-abscisic acid ester hybrid, and a known compound (4 S)-illicinone I. Their structures and configurations were mainly elucidated by spectroscopic analyses, CD experiments and X-ray crystallography. (2 S ,4 R ,11 S)-4- O -methyl-12-chloroillifunone C, (2 S ,4 R ,11 R)-2,3-dihydro-4- O -methyl illioliganfunone D, and illiternfunol A were found to exhibit weak activity against Coxsackievirus B3, with IC 50 values ranging from 27.8 to 33.3 μM. Illiternone B exhibited more potent activities against Coxsackievirus B3 and influenza virus A than did its geometric isomer illiternone A, with IC 50 values of 7.7 μM and 2.5 μM, respectively. None of these compounds displayed cytotoxic activities. Twelve undescribed prenylated C 6 –C 3 derivatives were isolated from Illicium ternstroemioides A. C. Smith. Illiternfunone A (10) represents the first example of prenylated C 6 –C 3 derivative-abscisic acid ester hybrid. Illiternone B (12) was found to exhibit potent activities against Coxsackie virus B3 and influenza virus A. [Display omitted] • Thirteen undescribed prenylated C 6 –C 3 derivatives were isolated from Illicium ternstroemioides A. C. Smith. • Illiternone B was found to exhibit potent activities against coxsackie virus B3 and influenza virus A. • Illiternfunone A represents the first example of prenylated C 6 –C 3 derivative-abscisic acid ester hybrid. [ABSTRACT FROM AUTHOR]
Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
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PubTypeId: academicJournal
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  Label: Title
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  Data: Prenylated C6–C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity.
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  Data: <searchLink fieldCode="AR" term="%22Zhang%2C+Jian-Pei%22">Zhang, Jian-Pei</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Li%2C+Wen-Rui%22">Li, Wen-Rui</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Wu%2C+Shuo%22">Wu, Shuo</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Wang%2C+Xiao-Jing%22">Wang, Xiao-Jing</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Wang%2C+Ru-Bing%22">Wang, Ru-Bing</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Li%2C+Mi%22">Li, Mi</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Su%2C+Guo-Zhu%22">Su, Guo-Zhu</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Wang%2C+Hai-Qiang%22">Wang, Hai-Qiang</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yong%2C+Jin-Yao%22">Yong, Jin-Yao</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yang%2C+Jia%22">Yang, Jia</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Li%2C+Li%22">Li, Li</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Li%2C+Yu-Huan%22">Li, Yu-Huan</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<i> yuhuanlibj@126.com</i><br /><searchLink fieldCode="AR" term="%22Ma%2C+Shuang-Gang%22">Ma, Shuang-Gang</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> mashuanggang@imm.ac.cn</i>
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  Data: <searchLink fieldCode="JN" term="%22Phytochemistry%22">Phytochemistry</searchLink>. Dec2021, Vol. 192, pN.PAG-N.PAG. 1p.
– Name: Subject
  Label: Subjects
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  Data: <searchLink fieldCode="DE" term="%22Influenza+A+virus%22">Influenza A virus</searchLink><br /><searchLink fieldCode="DE" term="%22Influenza+viruses%22">Influenza viruses</searchLink><br /><searchLink fieldCode="DE" term="%22Coxsackieviruses%22">Coxsackieviruses</searchLink><br /><searchLink fieldCode="DE" term="%22X-ray+crystallography%22">X-ray crystallography</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Thirteen compounds were isolated from the lipid-soluble extracts of Illicium ternstroemioides A. C. Smith, including eleven previously undescribed prenylated C 6 –C 3 compounds, a previously undescribed prenylated C 6 –C 3 derivative-abscisic acid ester hybrid, and a known compound (4 S)-illicinone I. Their structures and configurations were mainly elucidated by spectroscopic analyses, CD experiments and X-ray crystallography. (2 S ,4 R ,11 S)-4- O -methyl-12-chloroillifunone C, (2 S ,4 R ,11 R)-2,3-dihydro-4- O -methyl illioliganfunone D, and illiternfunol A were found to exhibit weak activity against Coxsackievirus B3, with IC 50 values ranging from 27.8 to 33.3 μM. Illiternone B exhibited more potent activities against Coxsackievirus B3 and influenza virus A than did its geometric isomer illiternone A, with IC 50 values of 7.7 μM and 2.5 μM, respectively. None of these compounds displayed cytotoxic activities. Twelve undescribed prenylated C 6 –C 3 derivatives were isolated from Illicium ternstroemioides A. C. Smith. Illiternfunone A (10) represents the first example of prenylated C 6 –C 3 derivative-abscisic acid ester hybrid. Illiternone B (12) was found to exhibit potent activities against Coxsackie virus B3 and influenza virus A. [Display omitted] • Thirteen undescribed prenylated C 6 –C 3 derivatives were isolated from Illicium ternstroemioides A. C. Smith. • Illiternone B was found to exhibit potent activities against coxsackie virus B3 and influenza virus A. • Illiternfunone A represents the first example of prenylated C 6 –C 3 derivative-abscisic acid ester hybrid. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.phytochem.2021.112935
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      – Code: eng
        Text: English
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        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Influenza A virus
        Type: general
      – SubjectFull: Influenza viruses
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      – SubjectFull: Coxsackieviruses
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      – SubjectFull: X-ray crystallography
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      – TitleFull: Prenylated C6–C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity.
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              Text: Dec2021
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