Cycloartane- and Lanostane-Type Triterpenoids from the Resin of Parthenium Argentatum AZ-2, a Byproduct of Guayule Rubber Production.

A total of 12 new cycloartane- and lanostane-type triterpenoids including 16-deoxyargentatin A (1), 16-deoxyisoargentatin A (2), 7-oxoisoargentatin A (3), 24-epi-argentatin H (4), 24-O-p-anisoylargentatin C (5), 24-O-trans-cinnamoylargentatin C (6), 16-dehydroargentatin C (7), 16,17(20)-didehydroargentatin C (8), isoargentatin C (9), isoargentatin H (10), 3-epi-quisquagenin (11), and isoquisquagenin (12) together with 10 known triterpenoids (13-22) were isolated from the resin of Parthenium argentatum AZ-2 obtained as a byproduct of Bridgestone guayule rubber production. The structures of new triterpenoids 1-12 and argentatin H (13), which has previously been characterized as its diacetate (23), were elucidated by extensive analysis of their spectroscopic data and chemical conversions, and the known compounds 14-22 were identified by comparison of their spectroscopic data with those reported. Of these, 13, 14, and 18 exhibited weak cytotoxic activity for several cancer cell lines.