SQUALENE DERIVATIVES FROM EURYCOMA-LONGIFOLIA

Three novel cytotoxic squalene-type triterpenes, eurylene, 14-deacetyl eurylene and longilene peroxide, together with teurilene were isolate d from the wood of Eurycoma longifolia. Their structures were elucidat ed by spectroscopic, chemical and X-ray analyses. The absolute stereos tructure of eurylene was determined by the advanced Mosher's method. T he molecular conformation of eurylene is extended, while those of long ilene peroxide and teurilene have 'horse shoe' structures. In 14-deace tyl eurylene, an intramolecular hydrogen bond forms a tetrahydrofuran- like structure ensuring a molecular conformation similar to that of lo ngilene peroxide and teurilene. The relationship of the structure and conformation of the compounds and their cytotoxicity are discussed.