Compounds from the insect Blaps japanensis with COX-1 and COX-2 inhibitory activities

[Display omitted] Blapsols A–D (1–4), four new compounds possessing a 2,3-dihydrobenzo[b][1,4]dioxin group, together with five known N-acetyldopamine dimers (5–9), were isolated from Blaps japanensis. Their structures including the absolute configuration of (+)-1 were determined by means of spectros...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2015-06, Vol.25 (12), p.2469-2472
Main Authors: Yan, Yong-Ming, Li, Li-Ji, Qin, Xiao-Chu, Lu, Qing, Tu, Zheng-Chao, Cheng, Yong-Xian
Format: Article
Language:English
Subjects:
Animals
Blaps japanensis
Coleoptera - chemistry
Coleoptera - metabolism
COX-1
COX-2
Crystallography, X-Ray
Cyclooxygenase 1 - chemistry
Cyclooxygenase 1 - metabolism
Cyclooxygenase 2 - chemistry
Cyclooxygenase 2 - metabolism
Cyclooxygenase Inhibitors - chemistry
Dioxins - chemistry
Insects
Magnetic Resonance Spectroscopy
Molecular Conformation
N-Acetyldopamine dimers
Stereoisomerism
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Summary:[Display omitted] Blapsols A–D (1–4), four new compounds possessing a 2,3-dihydrobenzo[b][1,4]dioxin group, together with five known N-acetyldopamine dimers (5–9), were isolated from Blaps japanensis. Their structures including the absolute configuration of (+)-1 were determined by means of spectroscopic and X-ray crystallographic methods. Chiral HPLC was used to separate (−)- and (+)-enantiomers of compounds 1–4, which were isolated from this insect as racemic mixtures. All the compounds were found to have inhibitory effects towards COX-2 with IC50 values in the range of 1.3–17.8μM.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.04.085