Diverse prieurianin-type limonoid derivatives from the fruits of Aphanamixis grandifolia and their absolute configuration determination

Twenty-five new highly oxygenated prieurianin-type limonoids, zaphaprinins A-Y (1-25), were isolated from the fruits of Aphanamixis grandifolia. Their structures were elucidated by extensive spectroscopic analyses. Absolute configurations for the key structures like I were assigned by a comprehensive method, such as comparing the calculated electronic circular dichroism (ECD) with the experimental one, single-crystal X-ray and Mosher ester method were also involved for other compounds' study. The solid data from X-ray diffraction allowed revision of the stereochemistry of the C-1-C-14 tetrahydropyran ring-type limonoid. The insecticidal activities of all the limonoids were evaluated. (C) 2014 Elsevier Ltd. All rights reserved.