Callistiviminenes A-O: Diverse adducts of β-triketone and sesqui- or monoterpene from the fruits of Callistemon viminalis

Published on Nov 1, 2016in Phytochemistry3.044
· DOI :10.1016/J.PHYTOCHEM.2016.08.014
Lin Wu8
Estimated H-index: 8
(CPU: China Pharmaceutical University),
Xiao-Bing Wang31
Estimated H-index: 31
(CPU: China Pharmaceutical University)
+ 4 AuthorsLing-Yi Kong58
Estimated H-index: 58
(CPU: China Pharmaceutical University)
Abstract Callistiviminenes A-O, fifteen adducts of β-triketone with sesqui- or monoterpene, along with a known compound, were isolated from the fruits of Callistemon viminalis . Callistiviminenes A and B are β-triketone-coupled (−)-bicyclosequiphellandrene contained an oxaspiro[5.5]undecene unit, and callistiviminenes C-E are rare adducts of β-triketone and bicyclogermacrene. Their structures and absolute configurations were elucidated by spectroscopic and computational methods, as well as by single-crystal X-ray diffraction experiment. A plausible biosynthetic pathway to these compounds involves a hetero-Diels–Alder reaction. Callistiviminenes C and D exhibited inhibition against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages with IC 50 value of 20.3  μ M and 32.5  μ M, respectively.
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