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Serratene triterpenoids from Lycopodium cernuum L. as α-glucosidase inhibitors: Identification, structure–activity relationship and molecular docking studies.

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Title: Serratene triterpenoids from Lycopodium cernuum L. as α-glucosidase inhibitors: Identification, structure–activity relationship and molecular docking studies.
Authors: Liu, Bing-Rui1,2 (AUTHOR), Zheng, Hai-Rong3,4 (AUTHOR), Jiang, Xian-Jun3,4 (AUTHOR), Zhang, Pu-Zhao1,5 (AUTHOR) zhpuzh@163.com, Wei, Guo-Zhu1,3,4 (AUTHOR) wgzcell@163.com
Source: Phytochemistry. Mar2022, Vol. 195, pN.PAG-N.PAG. 1p.
Subjects: Alpha-glucosidases, Molecular docking, Structure-activity relationships, Club mosses, Triterpenoids, Amino acid residues
Abstract: Phytochemical investigation of Lycopodium cernuum L. afforded seven undescribed serratene triterpenoids named 3 β, 21 β- dihydroxyserra-14-en-24-oic acid-3 β- (5′-hydroxybenzoate) (1), 3 β, 21 β , 24-trihydroxyserrat-14-en-3 β -(5′-hydroxyl benzoate) (2), 3 β , 14 α , 15 α , 21 β -tetrahydroxyserratane-24-methyl ester (3), 3 β , 14 α , 21 β -trihydroxyserratane-15 α -(4′-methoxy-5′-hydroxybenzoate)-24-methyl ester (4), 3 β , 14 α , 21 β -trihydroxyserratane-15 α -(4′-methoxy-5′-hydroxybenzoate) (5), 3 β -hydroxy-21 β -acetate-16-oxoserrat-14-en-24-oic acid (6), 3 β , 21 β -dihydroxy-16 α , 29-epoxyserrat-14-en-24-methyl ester (7), together with eleven known compounds (8 – 18), whose chemical structures were elucidated through spectroscopic analysis of HRESIMS, 1D NMR, 2D NMR and comparison between the literature. All compounds were evaluated for their α -glucosidase inhibitory activity for the first time. The results showed that compounds 1 , 2 , 4 , 5 , 6 , 10 , 13 , 15 , and 16 were among the most potent α-glucosidase inhibitors, with IC 50 values ranging from 23.22 ± 0.64 to 50.65 ± 0.82 μM. Structure – activity relationship (SAR) studies indicated that the combined properties of the 5-hydroxybenzoate moiety at C-3, β -OH at C-21, COOH- at C-24, and Δ14,15 groups enabled an increase in the α-glucosidase inhibitory effect. In addition, molecular docking studies showed that the potential inhibitors mainly interact with key amino acid residues in the active site of α -glucosidase through hydrogen bonds and hydrophobic forces. [Display omitted] • Seven undescribed serratene swere isolated from Lycopodium cernnum L. • Nine compounds showed significant inhibition against α-glucosidase for the first time. • The structure-activity relationship has been established. • The molecular docking studies of potential inhibitors were performed. [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.)
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  Data: Serratene triterpenoids from Lycopodium cernuum L. as α-glucosidase inhibitors: Identification, structure–activity relationship and molecular docking studies.
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  Data: <searchLink fieldCode="AR" term="%22Liu%2C+Bing-Rui%22">Liu, Bing-Rui</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zheng%2C+Hai-Rong%22">Zheng, Hai-Rong</searchLink><relatesTo>3,4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Jiang%2C+Xian-Jun%22">Jiang, Xian-Jun</searchLink><relatesTo>3,4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zhang%2C+Pu-Zhao%22">Zhang, Pu-Zhao</searchLink><relatesTo>1,5</relatesTo> (AUTHOR)<i> zhpuzh@163.com</i><br /><searchLink fieldCode="AR" term="%22Wei%2C+Guo-Zhu%22">Wei, Guo-Zhu</searchLink><relatesTo>1,3,4</relatesTo> (AUTHOR)<i> wgzcell@163.com</i>
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  Data: <searchLink fieldCode="JN" term="%22Phytochemistry%22">Phytochemistry</searchLink>. Mar2022, Vol. 195, pN.PAG-N.PAG. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Alpha-glucosidases%22">Alpha-glucosidases</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+docking%22">Molecular docking</searchLink><br /><searchLink fieldCode="DE" term="%22Structure-activity+relationships%22">Structure-activity relationships</searchLink><br /><searchLink fieldCode="DE" term="%22Club+mosses%22">Club mosses</searchLink><br /><searchLink fieldCode="DE" term="%22Triterpenoids%22">Triterpenoids</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+acid+residues%22">Amino acid residues</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Phytochemical investigation of Lycopodium cernuum L. afforded seven undescribed serratene triterpenoids named 3 β, 21 β- dihydroxyserra-14-en-24-oic acid-3 β- (5′-hydroxybenzoate) (1), 3 β, 21 β , 24-trihydroxyserrat-14-en-3 β -(5′-hydroxyl benzoate) (2), 3 β , 14 α , 15 α , 21 β -tetrahydroxyserratane-24-methyl ester (3), 3 β , 14 α , 21 β -trihydroxyserratane-15 α -(4′-methoxy-5′-hydroxybenzoate)-24-methyl ester (4), 3 β , 14 α , 21 β -trihydroxyserratane-15 α -(4′-methoxy-5′-hydroxybenzoate) (5), 3 β -hydroxy-21 β -acetate-16-oxoserrat-14-en-24-oic acid (6), 3 β , 21 β -dihydroxy-16 α , 29-epoxyserrat-14-en-24-methyl ester (7), together with eleven known compounds (8 – 18), whose chemical structures were elucidated through spectroscopic analysis of HRESIMS, 1D NMR, 2D NMR and comparison between the literature. All compounds were evaluated for their α -glucosidase inhibitory activity for the first time. The results showed that compounds 1 , 2 , 4 , 5 , 6 , 10 , 13 , 15 , and 16 were among the most potent α-glucosidase inhibitors, with IC 50 values ranging from 23.22 ± 0.64 to 50.65 ± 0.82 μM. Structure – activity relationship (SAR) studies indicated that the combined properties of the 5-hydroxybenzoate moiety at C-3, β -OH at C-21, COOH- at C-24, and Δ14,15 groups enabled an increase in the α-glucosidase inhibitory effect. In addition, molecular docking studies showed that the potential inhibitors mainly interact with key amino acid residues in the active site of α -glucosidase through hydrogen bonds and hydrophobic forces. [Display omitted] • Seven undescribed serratene swere isolated from Lycopodium cernnum L. • Nine compounds showed significant inhibition against α-glucosidase for the first time. • The structure-activity relationship has been established. • The molecular docking studies of potential inhibitors were performed. [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.)
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RecordInfo BibRecord:
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      – Type: doi
        Value: 10.1016/j.phytochem.2021.113056
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      – Code: eng
        Text: English
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        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Alpha-glucosidases
        Type: general
      – SubjectFull: Molecular docking
        Type: general
      – SubjectFull: Structure-activity relationships
        Type: general
      – SubjectFull: Club mosses
        Type: general
      – SubjectFull: Triterpenoids
        Type: general
      – SubjectFull: Amino acid residues
        Type: general
    Titles:
      – TitleFull: Serratene triterpenoids from Lycopodium cernuum L. as α-glucosidase inhibitors: Identification, structure–activity relationship and molecular docking studies.
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            NameFull: Liu, Bing-Rui
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            NameFull: Jiang, Xian-Jun
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            NameFull: Zhang, Pu-Zhao
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              Text: Mar2022
              Type: published
              Y: 2022
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              Value: 195
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