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The sterols of nine mature plant species in seven families ranging from the subphylum Lycopsida through the Filicopsida and the classes Gymnospermae and Angiospermae in the Pteropsida were structurally and stereochemically defined. Two plant categories were found. In the first, comprised by Dryopteris {Thelypteris) noveboracensis, Polystichum acrostichoides, Dennstaedtia punctilobuIa, Osmunda cinnamomea, Ginkgo biloba, Cucurbita pepo, and Kalmia latifolia, 24ot-alkylsterols were dominant and were composed principally of 24~-ethylcholesterol (sitosterol) or (in Cucurbita pepo) 24a-ethyllathosterol and its trans-22-dehydro derivative (spinasterol). Depending on the species, small amounts of 24a-ethyl-trans-22-dehydrocholesterol (stigmasterol), 24a-methylcholesterol (campesterol), 2 4fl-methylcholesterol (dihydrobrassicasterol, always less than campesterol), cholesterol, lathosterol, 2 4a-ethyllathosterol, 24~-methyllathosterol, trans-24-ethylidenelathosterol (AT-avenasterol), and (tentatively identified) 24-ethyl-24(25)-dehydrolathosterol were present. Spinacea oleracea was alsoCucurbitaceae, from Magnoliales through Theales to Ericales, nor from Ranales to Saxifragales. However, they are consonant with a relationship between Cucurbitaceae and Theales and between Rosales and Lamiales. Triterpenoids found in various of the families studied included cycloartenol and friedelin. The spectroscopic properties of the latter are described.

24‐Ethylcholesterol was shown by proton magnetic resonance spectroscopy to have only the α‐configuration in a series of tracheophytes ranging through the evolutionary hierarchy from ferns through gymnosperms and primitive angiosperms to climax angiosperms. 24‐Methylcholesterol, however, was consistently an epimeric mixture, with the 24α‐epimer present in about twice the concentration of the 24β‐epimer. 24‐Methylcholesterol was always present in smaller amount than the 24‐ethylcholesterol.

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