Caulerpenyne and Related Bis-enol Esters Are Novel-Type Inhibitors of Human 5-Lipoxygenase

Richter P., Schubert G., Schaible A. M., ÇAVAŞ L., Werz O., Pohnert G.

CHEMMEDCHEM, cilt.9, sa.8, ss.1655-1659, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 9 Sayı: 8
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1002/cmdc.201402065
  • Dergi Adı: CHEMMEDCHEM
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1655-1659
  • Anahtar Kelimeler: caulerpenyne, inhibition, lipoxygenase, structure activity, synthetic analogues, TAXIFOLIA, 15-LIPOXYGENASE, ANTIOXIDANT
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

Caulerpenyne (CYN) is a sesquiterpene from green algae with known inhibitory properties against soybean lipoxygenase. Here we introduce a detailed structure-activity study elucidating the inhibitory effects of CYN and a library of six synthetic CYN analogues on isolated human 5-lipoxygenase (5-LO) and cellular 5-LO in polymorphonuclear leukocytes. Essential structural elements are identified and a structurally simplified inhibitor is introduced. The modes of 5-LO inhibition by CYN and the synthetic inhibitors cannot be assigned to any of the known categories of lipoxygenase inhibitors. These compounds clearly interfere directly with 5-LO and represent rather small and flexible molecules, with unique structures among 5-LO inhibitors identified thus far.