Molecular structures and antiviral activities of naturally occurring and modified cassane furanoditerpenoids and friedelane triterpenoids from Caesalpinia minax.

Further investigation of the active components of the chloroform fraction of the seeds of Caesalpinia minax led to the isolation of a new cassane furanoditerpenoid, caesalmin H (1), together with two known furanoditerpenoid lactones, caesalmin B (2) and bonducellpin D (3). Reduction of the naturally abundant caesalmin D (9), E (10) and F (11) resulted in three new furanoditerpenoid derivatives 4-6. Phytochemical study of the stem of the same plant and subsequent reduction afforded two friedelane triterpenoids (7-8), which were identified by spectroscopic methods. Compounds 1-2 and 4-8 were corroborated by single crystal X-ray analysis. The factors governing the reduction of cassane furanoditerpenoids and friedelane triterpenoids were investigated by correlating the crystallographic results with density functional theory. The inhibitory activities of 2-8 on the Para3 virus were evaluated by cytopathogenic effects (CPE) reduction assay.