Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine

Abstract

Sarcophine (1), a cembranoid diterpene is known to inhibit the process of tumorigenesis. Sarcophine can be isolated in large amounts from the Red Sea soft coral Sarcophyton glaucum and hence is an ideal target for semisynthetic or biocatalytic modifications. Hydroxylated derivatives of 1 were reported to improve its anticancer activity. Despite the promising results and ready availability, there are limited attempts towards further diversifying the library of sarcophine derivatives. Hence, the current study targets the epoxide ring to generate sulfur-containing derivatives of sarcophine by reacting it with ammonium thiocyanate and Lawesson's reagent. Structure elucidation of the products was based on extensive 1D and 2D NMR and high resolution mass spectrometry, in addition to mechanistic considerations. The effect of these derivatives on highly malignant +SA mammary epithialial cell proliferation is reported. Anti-inflammatory potential of sarcophine and its derivatives is also demonstrated. © 2006 Pharmaceutical Society of Japan.