Humulene Sesquiterpenoids from Endemic Ferula brevipedicellata


Çaşkurlu A., Rebollar-Ramos D., Friesen B. J., Santarsiero B., Chen S., Pauli G. F., ...More

ASP 2023 Annual Meeting, Maryland, United States Of America, 22 - 26 July 2023, pp.244

  • Publication Type: Conference Paper / Summary Text
  • City: Maryland
  • Country: United States Of America
  • Page Numbers: pp.244
  • Istanbul University Affiliated: Yes

Abstract

Ferula plants are traditional medicines and sources of structurally distinct sesquiterpenes, coumarins, and monoterpenes, which collectively have been associated with therapeutically relevant bioactivities. F. brevipedicellata Peșmen ex Sağıroğlu & H. Duman occurs endemically in Turkey. Its constituents and bioactivities have not been studied yet. We now report its first systematic phytochemical investigation. While Ferula species are known to contain different classes of sesquiterpenes, humulenes are relatively rare, yet represent a major proportion of the CH2Cl2 extract of F. brevipedicellata. Isolates include the previously described humulene sesquiterpenes, kurubaschic acid angelate and kurubaschaldehyde benzoate, which were structurally dereplicated by spectroscopic methods as well as quantum-mechanics driven 1H iterative functionalized Spin Analysis (HifSA) for confirmatory relative stereochemical assignments. Characterization of three new compounds also involved crystal X-ray diffraction analysis for absolute stereochemical reference. A new methodology enables the definitive identification and distinction of angelic vs. tiglic acid using high-resolution long-range 1H,1H J coupling patterns. The outcomes support the distinct chemotaxonomical placement of F. brevipedicellata in the genus.