3,4- seco-Norclerodane Diterpenoids from the Roots of Polyalthia laui.

ABSTRACT

Ten new clerodane diterpenoids, polylauioids A-J (1-10), and five known analogues (11-15) were isolated from the roots of Polyalthia laui. Among the new compounds, 3 and 8 are artifacts. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. The absolute configurations of 4, 5, and 7 were defined based on single-crystal X-ray diffraction and electronic circular dichroism data. Compounds 1 and 2 represent the first examples of rearranged 3,4- seco-norclerodane diterpenoids, and a putative biosynthesis pathway for these compounds is proposed. Compounds 1, 4, 6, 7, 9, and 10 showed anti-HIV activities with EC50 values ranging from 12.2 to 35.2 µM.