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. |
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| 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] |
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| Database: | Engineering Source |
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