Immunomodulatory Biscembranoids and Assignment of Their Relative and Absolute Configurations: Data Set Modulation in the Density Functional Theory/Nuclear Magnetic Resonance Approach.
Peng SunFeng-Yuan CaiGianluigi LauroHua TangLi SuHong-Liang WangHuan Huan LiAttila MándiTibor KurtánRaffaele RiccioGiuseppe BifulcoWen ZhangPublished in: Journal of natural products (2019)
Five new biscembranoids, bistrochelides A-E (3-7), were isolated together with glaucumolides A (1) and B (2) from the soft coral Sarcophyton trocheliophorum. Their structures and absolute configurations were determined by spectroscopic methods, X-ray crystal diffraction, and DFT/NMR (density functional theory/nuclear magnetic resonance) and TDDFT/ECD (time-dependent density functional theory/electronic circular dichroism) calculations. A new approach is introduced to determine the relative configuration of a stereocenter through the dynamic evaluation of the mean absolute errors (MAEs) between the investigated diastereoisomers, moving from an "extended" to a more diagnostic "restricted" set of atoms. This research leads to the structure revision of glaucumolides A and B. In in vitro immunomodulatory screening, compounds 1 and 4 significantly induced the proliferation of CD3+ T cells, while compounds 1 and 5 significantly increased the CD4+/CD8+ ratio at 3 μM.
Keyphrases
- density functional theory
- magnetic resonance
- molecular dynamics
- high resolution
- total knee arthroplasty
- contrast enhanced
- molecular docking
- signaling pathway
- electronic health record
- diabetic rats
- drug induced
- atomic force microscopy
- patient safety
- solid state
- emergency department
- magnetic resonance imaging
- mass spectrometry
- computed tomography
- oxidative stress
- artificial intelligence
- crystal structure
- molecular dynamics simulations