Structural, stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum

Lin Fu Liang, T. Kurtán, Attila Mándi, Li Gong Yao, Jia Li, Le Fu Lan, Yue Wei Guo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A series of highly oxidative new cembranoids with diverse structural features such as a dienoate moiety (sarcophytonolides S – U, 1–3) or an α,β-unsaturated ε-lactone (sartrolides H – J, 4–6) were obtained from Hainan soft coral Sarcophyton trocheliophorum, along with known related analogues 7–13. It is an extremely challenging work to determine the absolute configurations of these metabolites. For compounds 1, 3 and 4, solution TDDFT calculation of ECD and specific rotation were applied in combination with conformational analysis and NMR data to determine their relative and absolute configurations, leading to the revision of relative configuration of 14. The absolute configurations of compounds 8–10 were determined by the solid-state TDDFT-ECD approach, and that of 8 was further confirmed by single-crystal X-ray diffraction experiment with Cu Kα radiation. In the bioassays, compound 8 exhibited not only moderate protein tyrosine phosphatase 1B (PTP1B) inhibitory activity (IC50 = 15.4 μM) but also moderate antibacterial activity against Staphylococcus aureus Newman strain (MIC50 = 250 μM).

Original languageEnglish
Pages (from-to)1933-1941
Number of pages9
JournalTetrahedron
Volume74
Issue number15
DOIs
Publication statusPublished - Apr 12 2018

Fingerprint

Non-Receptor Type 1 Protein Tyrosine Phosphatase
Anthozoa
Bioassay
Lactones
Metabolites
X-Ray Diffraction
Biological Assay
Inhibitory Concentration 50
Staphylococcus aureus
Nuclear magnetic resonance
Single crystals
Radiation
X ray diffraction
Experiments

Keywords

  • Absolute configuration
  • Biological activities
  • Cembranoid
  • Sarcophyton trocheliophorum
  • Structure elucidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Structural, stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum. / Liang, Lin Fu; Kurtán, T.; Mándi, Attila; Yao, Li Gong; Li, Jia; Lan, Le Fu; Guo, Yue Wei.

In: Tetrahedron, Vol. 74, No. 15, 12.04.2018, p. 1933-1941.

Research output: Contribution to journalArticle

Liang, Lin Fu ; Kurtán, T. ; Mándi, Attila ; Yao, Li Gong ; Li, Jia ; Lan, Le Fu ; Guo, Yue Wei. / Structural, stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum. In: Tetrahedron. 2018 ; Vol. 74, No. 15. pp. 1933-1941.
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