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Squalene derivatives from Eurycoma longifolia



Squalene derivatives from Eurycoma longifolia



Phytochemistry 34(3): 765-771



Three novel cytotoxic squalene-type triterpenes, eurylene, 14-deacetyl eurylene and longilene peroxide, together with teurilene were isolated from the wood of Eurycoma longifolia. Their structures were elucidated by spectroscopic, chemical and X-ray analyses. The absolute stereostructures of eurylene was determined by the advanced Mosher's method. The molecular conformation of eurylene is extended, while those of longilene peroxide and teurilene have 'horse shoe' structures. In 14-deacetyl eurylene, an intramolecular hydrogen bond forms a tetrahydrofuran-like structure ensuring a molecular conformation similar to that of longilene peroxide and teurilene. The relationship of the structure and conformation of the compounds and their cytotoxicity are discussed.

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Accession: 002699418

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DOI: 10.1016/0031-9422(93)85356-v


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