Steroids

9,11-Secogorgosterol, a secondary metabolite from the gorgonian Pseudopterogorgia americana, exhibits inhibitory activity against protein kinase C, and potent anti-proliferative and anti-inflammatory activity. An efficient method for the production of 9,11-secogorgosterol has been developed and optimized using an enzyme extract from the gorgonian P. americana. The gorgonian also produces two other 9,11-secosteroids which have marked differences in their side chains and nuclei, which suggested that the enzymes responsible for their production were likely relatively nonspecific. Novel 9,11-secosteroids have been synthesized using the enzyme extract from the gorgonian.

9,11-Secosteroids exhibit novel biological activity and interesting pharmacological properties. A biosynthetic study of 9,11-secogorgosterol and other novel 9,11-secosteroids using an enzyme extract from the gorgonian Pseudopterogorgia americana demonstrated that this system is an efficient catalyst for a wide range 9,11-secosteroid production. Two methods to recover the enzyme from 9,11-secosteroid synthesis have been developed: (1) membrane-enclosed enzymatic catalysis, which combines certain of the advantages of soluble enzymes and immobilized enzymes, shows high activity, simple recovery and at least 5 cycles or 23 days; (2) covalently bonded enzyme-agarose gel, attached by cyanogen bromide via the amino groups of enzymes, show 80% activity of free enzymes and at least 7 cycles or 46 days. Based on stability and kinetic studies of these immobilized enzymes in 9,11-secosteroid synthesis, a continuous flow column reactor for scale-up of 9,11-secosteroid production has been developed with great efficiency, which represents the first enzymatic production of a bioactive compound from a marine invertebrate on a large scale.