Molecular networking-assisted isolation of chlorophenolic glycosides from the rhizomes of Curculigo orchioides and their inhibitory effect on α-glucosidase

Jun Gu Kim, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang

Research output: Contribution to journalArticlepeer-review

Abstract

Molecular networking analysis and in silico tools, such as Network Annotation Propagation (NAP) and MolNetEnhancer, were applied to explore bioactive constituents present in the ethyl acetate-soluble fraction of the rhizomes of Curculigo orchioides. Among the molecular networks, the most abundant cluster was classified as a phenolic glycoside using the ClassyFire module of MolNetEnhancer. Further, the major node in this cluster was accurately predicted as curculigine A using the in silico fragment analysis tool, NAP. Six undescribed chlorophenolic glycosides (1–6) and 11 known phenolic glycosides were isolated, using molecular networking-assisted isolation methods, and their structures were elucidated using 1D, 2D-NMR and HRESIMS. In particular, the structures of the isolated chlorophenolic glycosides, which have non-protonated aromatic rings, were determined using various NMR experiments, such as 1D-selective NOE, ROESY, and LR-HMBC, and acid hydrolysis. All isolated compounds were examined to determine their inhibitory effects on α-glucosidase and compounds 3, 8, 10, 11, 13, 14, and 16 revealed the IC50 values ranging from 19.6 to 35.5 μM. Their structure-activity relationships were also evaluated based on the analysis of their inhibitory effects and performance of molecular docking simulations.

Original languageEnglish
Article number113820
JournalPhytochemistry
Volume214
DOIs
Publication statusPublished - 2023 Oct

Bibliographical note

Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST, 2020R1A2C1008406) and Medical Research Center program (2017R1A5A2015541). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST, 2020R1A2C1008406 ) and Medical Research Center program ( 2017R1A5A2015541 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Publisher Copyright:
© 2023 Elsevier Ltd

Keywords

  • Amaryllidaceae
  • Chlorophenolic glycosides
  • Curculigo orchioides
  • α-Glucosidase inhibitory activity

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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