Alfred J. Weinheimer

Chemistry of coelenterates. I. Occurrence of terpenoid compounds in gorgonians.

As part of a study of the comparative biochemistry of marine invertebrates, we have examined a number of gorgonians (class Anthozoa; subclass Alcyonaria; order Gorgonacea) for the occurrence of nonlipid organic compounds. From certain species we have obtained crystalline as well as liquid substances that seem to be terpenoid compounds. These substances appear to account for the antibiotic activity of gorgonian extracts,l for part of the odor of the animals, and for the irritation of skin and eyes caused by handling gorgonians. Yields of the crystalline compounds ranged from 0.005 to 1.5 per cent of the dry weight of gorgonian cortex. The infrared spectra of the solid compounds show strong absorption in the carbonyl region, and the compounds appear to be lactones. The nonlipid oils obtained from the animals are unsaturated hydrocarbons with an admixture of ketonic material.

Naturally Occurring Cembranes

The first studies which established the structures of members of the new group of diterpenes known as cembranes appeared in 1962 when Dauben, Thiessen, and Resnick (1), and Kobayashi and Akiyoshi (2) simultaneously published the structure of the hydrocarbon cembrene (1) from pine oleoresins, and Rowland and Roberts (3) published the structure of two diastereomeric cembrenediols from tobacco. Since that time, many more members of this new class of diterpenes have been discovered. Those originating in terrestrial plants have been encountered primarily in pines and tobacco. More recently, growing numbers of cembranoids have been found in the coelenterate phylum of lower marine invertebrates.

Echinolactone A and B: isolation and structures of two novel lactones from the marine coelenterate Echinopora lamellosa

Two novel pentacyclic triterpenes were isolated from the marine coelenterate Echinopora lamellose; their structures and absolute configuration (determined from spectroscopic and X-ray diffraction data) are reported.