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

Abstract 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 1 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.