Systematic naming system for Actaea triterpenes and the demand for dreiding models

Abstract

The genus Actaea, recently expanded to include the now obsolete genera Cimicifuga and Souliea, has been the source of ˜200 structurally defined triterpenes (TTs). Except for a few ubiquitous TTs, all are endemic to Actaea and derivatives of the simple cycloartanol, 1. Despite this one common denominator, the TTs comprise chemically diverse substructures, formed by oxidation, ring closure and ring cleavage. Extracts of many Actaea species are ethno-medicinal and CAM products. During their discovery, the TTs were given a wide variety of names, derived haphazardly from names of the species, the traditional medicine, or occasionally from a previously described structure. Often, there is little or no chemical logic to these names. We have developed a systematic naming system based on “actanol” for 1, with all modifications following standard chemical nomenclature. The standard α and β TT stereo designation breaks down in several substructural types with spiro ring systems, and the Cahn-Ingold-Prelog system is used exclusively for defining the skeleton. In the more complex structures, this created a demand for stereo models, and the inability to purchase our favored Dreiding models, led us to establish the Dreiding Model Exchange (http://tigger.uic.edu/˜gfp/dreiding/dreidingexchange.htm), which currently has over 3,000 pieces and is currently actively buying and selling these models.