Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

Yun Hyeok Choi, Changon Seo, Wonsik Jeong, Ji Eun Lee, Jae Yeon Lee, Eun Kyung Ahn, Jae Shin Kang, Jae Ho Lee, Chun Whan Choi, Joa Sub Oh, Dongho Lee, Seong Su Hong

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Abstract

The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC 50 values between 0.05 and 4.28 μM.

Original languageEnglish
Pages (from-to)714-719
Number of pages6
JournalBioorganic Chemistry
Volume87
DOIs
Publication statusPublished - 2019 Jun 1

Keywords

  • 2-Quinolone alkaloid
  • Glycopentanolone
  • Glycosmis pentaphylla
  • β-hexosaminidase

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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    Choi, Y. H., Seo, C., Jeong, W., Lee, J. E., Lee, J. Y., Ahn, E. K., Kang, J. S., Lee, J. H., Choi, C. W., Oh, J. S., Lee, D., & Hong, S. S. (2019). Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla. Bioorganic Chemistry, 87, 714-719. https://doi.org/10.1016/j.bioorg.2019.03.069