6'-Hydroxyoxosorbicillinol, a New Lipoxygenase Inhibitor and PGD₂/LTB₄Release Suppressor fromPenicilliumsp.

Abstract

A new lipoxygenase inhibitor, 60 -hydroxyoxosorbicillinol (1, C 14 H 16 O 6 ), was identified from a culture of Penicillium sp. A known compound, oxosorbicillinol (2, C 14 H 16 O 5 ), was also isolated. Compound 1 showed an approximately 10 times greater inhibitory effect on soybean lipoxygenase (IC 50 , 16M) than 2 (IC 50 , 150 M), and also showed prostaglandin D 2 (PGD 2 ) and leucotriene B 4 (LTB 4 ) release suppression activity (IC 50 , 10 M for PGD 2 and 100 M for LTB 4 ).

Sorbicillinoids from Fungi and Their Bioactivities

“…[22] Bisvertinolone (34) Inhibitory effect on β-l,6-glucan biosynthesis [42] Isobisvertinol (38) Inhibitory effect on lipid droplet accumulation in mouse macrophages [40] Trichodimerol (42) Inhibitory effect on bacterial endotoxin-induced production of tumor necrosis factor (TNF-α) in murine macrophages and human peripheral blood monocytes [46] Inhibitory effect on lipopolysaccharide-induced eicosanoid secretion in THP-1 human monocytic cells [66] Suppression of the production of tumor necrosis factor-α and nitric oxide in LPS-stimulate RAW264.7 cells [50] Dihydrotrichodimerol (44) Activation of peroxisome proliferator-activated recptor γ (PPAR γ) with an ED 50 of 80 ng/mL [50] Suppression of the production of tumor necrosis factor-α and nitric oxide in LPS-stimulate RAW264.7 cells [50] Effect on feeding perference of the aphid [48] Bislongiquinolide (49) Effect on feeding perference of the aphid [48] Sorbiterrin A (79) Inhibitory effect on acetylcholinesterase activity with IC 50 value of 25 µg/mL [61] Note: "ED 50 " means the median effective dose. "IC 50 " means the median inhibitory concentration.…”

“…6 1 -Hydroxyoxosorbicillinol (4) also exhibited prostaglandin D 2 and leukotriene B 4 release suppression activity with IC 50 values of 10 and 100 µM, respectively [22]. Sorbiterrin A (79) showed moderate acetylcholinesterase (AChE) inhibitory effect with IC 50 value of 25 µg/mL [61].…”