Add time:09/06/2019 Source:sciencedirect.com
The structures of cynanchogenin (1) and sarcostin (2) have been based on chemical and physicochemical evidence, and the correlations of lineolon (-deacylcynanchogenin; 3) with a conventional steroid is described. In 1959, the authors proposed the tentative structure (A),2 for cynanchogenin (1), an aglycone from Cynanchum caudatum Maxim. (Asclepiadaceae).3 In the same year, Cornforth gave the structure (B),4 for sarcostin (2), which is also an aglycone from an Australian plant, Sarcostemma australe.5 Abisch et al. also isolated several compounds from an African plant, Pachycarpus lineolatus, among which lineolon (-deacylcynanchogenin) (3) and sarcostin (2) are the main components.6 Since then, both compounds have been isolated from many plants and have been shown to be a very widely distributed steroids.1The C-nor-D-homopregnane skeleton of the structures A and B was assumed mainly on the basis of selenium dehydrogenation data,7 but after our new finding on the dehydrogenation,1b we reinvestigated the whole problem and reached new tentative structures.2 Meanwhile, Reichstei's group published a communication,8 in which they proposed the same structures mainly on physico-chemical evidence, and this prompted us to publish a short summary of our work without conclusive evidence.1c Now, our success in correlating the compounds, enables us to report all the details of the structural study.9
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