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Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and
Tingting Liu1, Haibo Wu2, Hongyun Jiang1
1Key Laboratory of Control of Biological Hazard Factors (Plant Origin) for Agriproduct Quality and Safety, Ministry of Agriculture and Rural Affairs of the People's Republic of China , Institute of Plant Protection, Chinese Academy of Agricultural Sciences , Beijing 100193 , China.
Abstract:
A new dimeric eudesmane sesquiterpenoid with an unreported 6/6/5/6/6 fused carbon skeleton, echingridimer A (1), and five monomers (2-6), including two new compounds (2 and 3), were isolated from the roots of Echinops grijsii. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses and confirmed by X-ray crystallography or electronic circular dichroism spectra. Compound 1 represents the first example of a 3,15'-linked Michael-type adduct of two eudesmanes, which feature a unique 1-oxaspiro[4.5]decan moiety. The plausible biogenetic pathway for 1-6 was briefly discussed. The oxaspiro dimer (1) not only showed stronger aphicidal activity than closely related monomeric compounds (2-6) and the commercial aphicide pymetrozine but also exhibited remarkable insecticide activity against a broad range of aphids, thus could be used as a potential biobased insecticide to suppress aphids.
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