3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus

Wan Fei Li, Zheng Ming Liang, Chen Liang Zhao, Nga Yi Tsang, Ji Xin Li, Ya Hua Liu, Kang He, Lu Tai Pan, Lijun Rong, Juan Zou*, Hong Jie Zhang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 1–3 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 1–3 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9–66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential.

Original languageEnglish
Article number3098
JournalMolecules
Volume27
Issue number10
DOIs
Publication statusPublished - 2 May 2022

Scopus Subject Areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

User-Defined Keywords

  • antifungal activity
  • antiviral activity
  • cytotoxicity
  • diterpenoids
  • Isodon flavidus

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