ent-Labdane and ent-kaurane diterpenoids from Chelonopsis odontochila with alpha-glucosidase inhibitory activity
Deng, Zhen-Tao1; Chen, Ji-Jun1,2; Geng, Chang-An1
Corresponding AuthorGeng, Chang-An(gengchangan@mail.kib.ac.cn)
2020
Source PublicationBIOORGANIC CHEMISTRY
ISSN0045-2068
Volume95Pages:10
AbstractEleven new ent-labdane diterpenoids, cheodontoins A-K (1-11), and thirteen known diterpenoids involving two ent-labdanes (12-13) and eleven ent-kauranes (14-24), were isolated from the active part of Chelonopsis odontochila (Lamiaceae) under the guidance of bioassay. The structures of cheodontoins A-K (1-11) were elucidated by extensive HRESIMS, 1D and 2D NMR, [alpha](D) and ECD experiments, X-ray diffraction and quantum calculation. Interestingly, five nor-ent-labdanes (9-13) were obtained from this genus for the first time. One ent-labdane diterpenoid (12) and four ent-kaurane diterpenoids (16, 19, 23, and 24) showed a-glucosidase inhibitory activity with IC50 values of 326.5 +/- 3.5, 599.1 +/- 13.8, 620.1 +/- 16.1, 185.0 +/- 4.2, and 190.7 +/- 11.6 mu M, respectively. Compounds 12 and 16 were a-glucosidase mixed-type inhibitors with K-i values of 334.1 and 589.2 mu M according to the enzyme kinetics using Lineweaver-Burk and Dixon plots. Docking study manifested that compounds 12 and 23 well located in the catalytic pocket of a-glucosidase by hydrophobic effects with Trp1355, Trp1369, Phe1427, Phe1559, and Phe1560 residues. This study provides new insights for the antidiabetic effects of C. odontochila with ent-labdane and ent-kaurane diterpenoids as the active constituents.
KeywordCheodontoins A-K Ent-Labdane diterpenoids Ent-Kaurane diterpenoids alpha-Glucosidase inhibitory activity Chelonopsis odontochila Enzyme kinetics Docking study
DOI10.1016/j.bioorg.2020.103571
Indexed BySCI ; SCI
Language英语
WOS Research AreaBiochemistry & Molecular Biology ; Chemistry
WOS SubjectBiochemistry & Molecular Biology ; Chemistry, Organic
WOS IDWOS:000512762900077
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/71186
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorGeng, Chang-An
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Deng, Zhen-Tao,Chen, Ji-Jun,Geng, Chang-An. ent-Labdane and ent-kaurane diterpenoids from Chelonopsis odontochila with alpha-glucosidase inhibitory activity[J]. BIOORGANIC CHEMISTRY,2020,95:10.
APA Deng, Zhen-Tao,Chen, Ji-Jun,&Geng, Chang-An.(2020).ent-Labdane and ent-kaurane diterpenoids from Chelonopsis odontochila with alpha-glucosidase inhibitory activity.BIOORGANIC CHEMISTRY,95,10.
MLA Deng, Zhen-Tao,et al."ent-Labdane and ent-kaurane diterpenoids from Chelonopsis odontochila with alpha-glucosidase inhibitory activity".BIOORGANIC CHEMISTRY 95(2020):10.
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