Issue 29, 2023

Ternifolipyrons A–J: new cytotoxic α-pyrones from Isodon ternifolius (D. Don) Kudô

Abstract

Isodon ternifolius (D.Don) Kudô is an important Asian herb used in traditional medicine against several diseases. Nineteen compounds were isolated from the dichloromethane–methanol (1 : 1) extract of I. ternifolius roots, including ten new α-pyrone derivatives, named ternifolipyrons A–J. The chemical structures of the isolates were determined by a combination of 1D and 2D NMR, along with LR- and HRMS spectroscopy. The absolute configurations of the α-pyrone derivatives were constructed based upon the X-ray signal crystal of the bromobenzoyl derivative of 1 as well as the electronic circular dichroism (ECD). All isolates (1–19) were investigated for their growth-inhibitory potential towards CCRF-CEM-leukemia cells at a fixed concentration of 30 μM. The compounds which exerted more than 50% inhibition at this concentration, compounds (7, 10, 12, 15–17), were tested at a different concentration range to determine their IC50 values in CCRF-CEM leukemia, MDA-MB-231 triple-negative breast cancer, and MCF7 breast cancer cell lines. Ursolic acid (16) showed the most potent activity against the three cancer cell lines with IC50 values of 8.37, 18.04, and 18.93 μM, respectively.

Graphical abstract: Ternifolipyrons A–J: new cytotoxic α-pyrones from Isodon ternifolius (D. Don) Kudô

Supplementary files

Article information

Article type
Paper
Submitted
11 mei 2023
Accepted
07 jun 2023
First published
29 jun 2023
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 19710-19720

Ternifolipyrons A–J: new cytotoxic α-pyrones from Isodon ternifolius (D. Don) Kudô

A. I. Elshamy, T. A. Mohamed, N. Swapana, Y. Kasai, M. Noji, T. Efferth, H. Imagawa, M. F. Hegazy and A. Umeyama, RSC Adv., 2023, 13, 19710 DOI: 10.1039/D3RA03146B

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