New 3,4-seco-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge Spongia sp.

Chi Jen Tai, Chih Hua Chao, Atallah F. Ahmed, Chia Hung Yen, Tsong Long Hwang, Fang Rong Chang, Yusheng M. Huang, Jyh Horng Sheu*

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

1 Scopus citations

Abstract

Continuing chemical investigation of the Red Sea sponge Spongia sp. led to the isolation of four new 3,4-seco-3,19-dinorspongian diterpenoid lactones, secodinorspongins A−D (1−4), along with a classical spongian diterpenoid lactone, sponginolide (5). The chemical structures, including the absolute configurations of these compounds, were elucidated using the extensive spectroscopic study composed of 1D and 2D NMR data analyses, and a comparison between calculated-electronic-circular-dichroism (ECD) and experimental-circular-dichroism (CD) spectra. A plausible biosynthetic pathway of 1−4 was also proposed. Furthermore, the cytotoxicity, antibacterial and anti-inflammatory activities of 1−5 were evaluated. Compound 1 was found to exhibit inhibitory activity against the growth of Staphylococcus aureus (S. aureus), and 4 and 5 exhibited suppression of superoxide-anion generation and elastase release in fMLF/CB-induced human neutrophils.

Original languageEnglish
Article number1252
JournalInternational Journal of Molecular Sciences
Volume24
Issue number2
DOIs
StatePublished - 08 01 2023

Bibliographical note

Publisher Copyright:
© 2023 by the authors.

Keywords

  • 3,4-seco-3,19-dinorspongian diterpenoid lactones
  • Red Sea sponge
  • Spongiasp
  • anti-inflammatory
  • antibacterial assay
  • secodinorspongins A−D
  • spongian diterpene
  • Humans
  • Lactones
  • Diterpenes/chemistry
  • Animals
  • Molecular Structure
  • Porifera/chemistry
  • Staphylococcus aureus

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