Abstract
Ten neolignans or norlignans (1–10) including eight new compounds were isolated from the whole bodies of Polyphaga plancyi Bolivar. Their structures were identified by spectroscopic data. Compounds 3, 4, 8, and 9 are racemates indicated by chiral HPLC analysis. Chiral separation followed by ECD calculations allowed to clarify the absolute configurations of all the antipodes. All the new compounds were evaluated for their biological properties toward extracellular matrix in rat renal proximal tubular cells, human cancer cells (K562, A549, and Huh7), EV71, ROCK2, JAK3, DDR1, and coagulation.Graphic
Highlights
Insects are a special group of existence on the earth
As far as the title species was concerned, eight new compounds and two known compounds belonging to neolignans and norlignans were isolated in this study (Fig. 1)
Subsequent absolute configuration clarification was aided by electronic circular dichroism (ECD) calculations
Summary
Plancyin A (1) has the molecular formula C 18H18O6 deduced from analysis of its HRESIMS ([M−H]−, m/z 329.1040, calcd 329.1031), 13C NMR, and DEPT spectra, indicating 10 degrees of unsaturation. Plancyin E (5) has the molecular formula C17H18O4 (9 degrees of unsaturation), based on analysis of its HREIMS and NMR data Inspection of these NMR data disclosed that the structure of 5 extremely resemble that of 3, differing in that a carboxyl group of C-8 is absent gaining support from the HMBC correlations of H-8/C-1, C-4′, C-6′ and the chemical shift of C-8 (δC 39.0). A pivotal ROESY correlation of H-8/H7′ in consideration of the chemical shift of C-8′ (δC 139.9) suggests the position of ester oxygen and the presence of E-configurated olefinic protons (H-7′ and H-8′), in accordance with the requirement of degrees of unsaturation Taken together, these data enable assignment of the structure of 7. 6.69, d, 8.0 6.50, dd, 8.0, 1.6 3.87, overlap 4.10, dd, 11.0, 5.1; 3.64, dd, 11.0, 8.9
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