View in EDS

Highly oxidized sesquiterpenes from the fruits of Illicium lanceolatum A. C. Smith.

Saved in:
Bibliographic Details
Title: Highly oxidized sesquiterpenes from the fruits of Illicium lanceolatum A. C. Smith.
Authors: Liu, Yang-Lan1 (AUTHOR), Li, Wen-Rui1 (AUTHOR), Wang, Xiao-Jing1 (AUTHOR), Wang, Ru-Bing1 (AUTHOR), Li, Mi1 (AUTHOR), Zhang, Jian-Pei1 (AUTHOR), Yong, Jing-Yao1 (AUTHOR), Bao, Xiu-Qi1 (AUTHOR), Zhang, Dan1 (AUTHOR), Ma, Shuang-Gang1 (AUTHOR) mashuanggang@163.com
Source: Phytochemistry. Apr2020, Vol. 172, pN.PAG-N.PAG. 1p.
Subjects: Sesquiterpenes, Fruit, X-ray diffraction
Abstract: Ten undescribed highly oxidized sesquiterpenes and six known sesquiterpenes were isolated from H 2 O-soluble part of the fruits of Illicium lanceolatum A. C. Smith. The structures of undescribed compounds were elucidated by interpretation of spectroscopic data, and the absolute configurations of 2 α -hydroxyneoanisatinic acid, (1 R ,5 R ,6 S ,7 R ,9 R ,10 R)-3,4-dehydro-12-hydroxy-floridanolide, and (1 R ,4 S ,5 R ,6 S ,7 S ,9 S)-1-deoxy-13-hydroxymerrilactone B were determined by the single-crystal X-ray diffraction analysis. Illilanceolatin A was the first example of a seco -prezizaane type sesquiterpene with a hemiacetal moiety located at C-10. 2 α -Hydroxyneoanisatinic acid and anisatinic acid were two naturally occurring undescribed seco -prezizaane type sesquiterpenes with a 5/5/6 tricyclic carbon skeleton. Plausible biosynthetic pathways of the isolated polycyclic and highly oxidized sesquiterpenes derived from the intermediate allo -cedrane were proposed. (1 R ,5 R ,6 S ,7 R ,9 R ,10 R)-3,4-dehydro-12-hydroxy-floridanolide, 1,3-dihydroxyneoanisatin, and 2 α -hydroxyneoanisatin displayed neuroprotective effects with protection rates of 19.9, 22.7 and 24.3% at 10 μ M, respectively. Additionally, the preliminary acute toxicity of anisatinic acid was also evaluated. Ten undescribed highly oxidized sesquiterpenes, along with six known analogues were isolated from the fruits of Illicium lanceolatum. Their neuroprotective, cytotoxic, anti-inflammatory, and antiviral activities were evaluated. Image 1 • Ten undescribed highly oxidized sesquiterpenes were isolated from the fruits of Illicium lanceolatum A. C. Smith. • Illilanceolatin A was the first example of a seco -prezizaane type sesquiterpene with a hemiketal moiety located at C-10. • Plausible biosynthetic pathways of sesquiterpenes derived from the intermediate allo -cedrane were proposed. [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
FullText Text:
  Availability: 0
Header DbId: egs
DbLabel: Engineering Source
An: 141942508
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Highly oxidized sesquiterpenes from the fruits of Illicium lanceolatum A. C. Smith.
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Liu%2C+Yang-Lan%22">Liu, Yang-Lan</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="%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="%22Zhang%2C+Jian-Pei%22">Zhang, Jian-Pei</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yong%2C+Jing-Yao%22">Yong, Jing-Yao</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Bao%2C+Xiu-Qi%22">Bao, Xiu-Qi</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zhang%2C+Dan%22">Zhang, Dan</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ma%2C+Shuang-Gang%22">Ma, Shuang-Gang</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> mashuanggang@163.com</i>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%22Phytochemistry%22">Phytochemistry</searchLink>. Apr2020, Vol. 172, pN.PAG-N.PAG. 1p.
– Name: Subject
  Label: Subjects
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Sesquiterpenes%22">Sesquiterpenes</searchLink><br /><searchLink fieldCode="DE" term="%22Fruit%22">Fruit</searchLink><br /><searchLink fieldCode="DE" term="%22X-ray+diffraction%22">X-ray diffraction</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Ten undescribed highly oxidized sesquiterpenes and six known sesquiterpenes were isolated from H 2 O-soluble part of the fruits of Illicium lanceolatum A. C. Smith. The structures of undescribed compounds were elucidated by interpretation of spectroscopic data, and the absolute configurations of 2 α -hydroxyneoanisatinic acid, (1 R ,5 R ,6 S ,7 R ,9 R ,10 R)-3,4-dehydro-12-hydroxy-floridanolide, and (1 R ,4 S ,5 R ,6 S ,7 S ,9 S)-1-deoxy-13-hydroxymerrilactone B were determined by the single-crystal X-ray diffraction analysis. Illilanceolatin A was the first example of a seco -prezizaane type sesquiterpene with a hemiacetal moiety located at C-10. 2 α -Hydroxyneoanisatinic acid and anisatinic acid were two naturally occurring undescribed seco -prezizaane type sesquiterpenes with a 5/5/6 tricyclic carbon skeleton. Plausible biosynthetic pathways of the isolated polycyclic and highly oxidized sesquiterpenes derived from the intermediate allo -cedrane were proposed. (1 R ,5 R ,6 S ,7 R ,9 R ,10 R)-3,4-dehydro-12-hydroxy-floridanolide, 1,3-dihydroxyneoanisatin, and 2 α -hydroxyneoanisatin displayed neuroprotective effects with protection rates of 19.9, 22.7 and 24.3% at 10 μ M, respectively. Additionally, the preliminary acute toxicity of anisatinic acid was also evaluated. Ten undescribed highly oxidized sesquiterpenes, along with six known analogues were isolated from the fruits of Illicium lanceolatum. Their neuroprotective, cytotoxic, anti-inflammatory, and antiviral activities were evaluated. Image 1 • Ten undescribed highly oxidized sesquiterpenes were isolated from the fruits of Illicium lanceolatum A. C. Smith. • Illilanceolatin A was the first example of a seco -prezizaane type sesquiterpene with a hemiketal moiety located at C-10. • Plausible biosynthetic pathways of sesquiterpenes derived from the intermediate allo -cedrane were proposed. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  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.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=141942508
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.phytochem.2020.112281
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Sesquiterpenes
        Type: general
      – SubjectFull: Fruit
        Type: general
      – SubjectFull: X-ray diffraction
        Type: general
    Titles:
      – TitleFull: Highly oxidized sesquiterpenes from the fruits of Illicium lanceolatum A. C. Smith.
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Liu, Yang-Lan
      – PersonEntity:
          Name:
            NameFull: Li, Wen-Rui
      – PersonEntity:
          Name:
            NameFull: Wang, Xiao-Jing
      – PersonEntity:
          Name:
            NameFull: Wang, Ru-Bing
      – PersonEntity:
          Name:
            NameFull: Li, Mi
      – PersonEntity:
          Name:
            NameFull: Zhang, Jian-Pei
      – PersonEntity:
          Name:
            NameFull: Yong, Jing-Yao
      – PersonEntity:
          Name:
            NameFull: Bao, Xiu-Qi
      – PersonEntity:
          Name:
            NameFull: Zhang, Dan
      – PersonEntity:
          Name:
            NameFull: Ma, Shuang-Gang
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 01
              M: 04
              Text: Apr2020
              Type: published
              Y: 2020
          Identifiers:
            – Type: issn-print
              Value: 00319422
          Numbering:
            – Type: volume
              Value: 172
          Titles:
            – TitleFull: Phytochemistry
              Type: main
ResultId 1