Yuccalechins A-C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities

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Pecio L., Alilou M., Kozachok S., ERDOĞAN ORHAN İ., EREN G., ŞENOL DENİZ F. S., ...Daha Fazla

MOLECULES, cilt.24, sa.22, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24 Sayı: 22
  • Basım Tarihi: 2019
  • Doi Numarası: 10.3390/molecules24224162
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: Yucca schidigera, Asparagaceae, spirobiflavonoid, absolute configuration, DP4+, ECD, Alzheimer's disease, MAGNETIC-RESONANCE SPECTRA, TANDEM MASS-SPECTROMETRY, ALZHEIMERS-DISEASE, STEROIDAL SAPONINS, PHENOLIC-COMPOUNDS, STEREOELECTRONIC INTERACTIONS, STRUCTURAL REVISION, COMPLETE PREDICTION, ORGANIC-MOLECULES, DFT CALCULATIONS
  • Gazi Üniversitesi Adresli: Evet

Özet

The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC50 47.44 and 47.40 mu g mL(-1), respectively). Gel filtration on Sephadex LH-20 and further RP-C-18 preparative HPLC of EtOAc fraction afforded 15 known and 3 new compounds, stereoisomers of larixinol. The structures of the isolated spirobiflavonoids 15, 26, and 29 were elucidated using 1D and 2D NMR and MS spectroscopic techniques. The relative configuration of isolated compounds was assigned based on coupling constants and ROESY (rotating-frame Overhauser spectroscopy) correlations along with applying the DP4+ probability method in case of ambiguous chiral centers. Determination of absolute configuration was performed by comparing calculated electronic circular dichroism (ECD) spectra with experimental ones. Compounds 26 and 29, obtained in sufficient amounts, were evaluated for activities against AChE and BChE, and they showed a weak inhibition only towards AChE (IC50 294.18 mu M for 26, and 655.18 mu M for 29). Furthermore, molecular docking simulations were performed to investigate the possible binding modes of 26 and 29 with AChE.