Guidongnins I–J: Two New 6,7-seco-7,20-Olide-ent-kaurene Diterpenes with Unusual Structures from Isodon rubescens

Juan Zou, Jianghai Ye, Chenliang Zhao, Jingjie Zhang, Yahua Liu, Lutai Pan, Kang He*, Hongjie Zhang*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

Abstract

Two undescribed ent-kaurene diterpenes, named guidongnins I (1) and J (2), were isolated from the medicinal plant Isodon rubescens. Compound 1 was determined to contain an unprecedented 23 carbons in the skeleton by bearing an extra isopropyl group at C-17 out of the diterpenoid parent structure, and compound 2 was the first example of 6,7-seco-7,20-olide-ent-kaurenes with two fused-tetrahydrofuran rings formed between C-6 and C-19/C-20 through oxygen bridges. Their structures, including their absolute configurations, were determined using the analyses of the spectroscopic and X-ray diffraction data. Guidongnins I (1) and J (2) were assessed for their anti-cancer activities against the growth of various cancer cell lines, and 2 displayed cytotoxic potency against HepG2 at IC50 27.14 ± 3.43 μM.

Original languageEnglish
Article number13451
Number of pages8
JournalInternational Journal of Molecular Sciences
Volume24
Issue number17
Early online date30 Aug 2023
DOIs
Publication statusPublished - Sept 2023

Scopus Subject Areas

  • Organic Chemistry
  • Drug Discovery
  • Spectroscopy
  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Molecular Biology
  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

User-Defined Keywords

  • Isodon rubescens
  • ent-kaurene diterpenoid
  • isopropyl group
  • anti-cancer
  • plausible biosynthetic pathway

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