The leaves and stalks of Solanum laciniatum AIT grown in Egypt were found by isolation to contain the steroid alkaloid solasodine (25 R)-22 a N-spirosol-5 en-30-01 (I) and two steroid sapogenins, diosgenin (25 D)-spirost-5-en-3b-01 (11) and chlorogenin (25 D)-5a-spirostane-3(3-6a-diol(III). Solanurn laciniaturn AIT. is a subtropical plant originating form Australia and New Zealand. It is considered as an important source for large scale production of solasodine especially in countries where supplies of other steroid raw materials, e. g., sapogenins are not sufficiently available (SCHREIBER 1968). The plant has received extensive inv.estigati0n.s by different research groups. SCHREIBER etal., (1961) isolated from the leaves solasonine, solamargine and fi-solamargine. BITE et al. (1962) isolated from the roots solasonine and solamargine together with two new alkaloids which were designated as solaradixine and solaradinine. GUSEVA et al. (1965) and FAYEZ et al. (1969) reported the presence of solasonine and solamargine in the leaves.In the present investigation, solasodine (25 R)-22 a N-spirosol-5-en-3fi-01 (I) and two steroid sapogenins, diosgenine (25 D)-spirosta-5-en-30-01 (11) and chlorogenin (25 D)-Sa-spirostane-30-6a-diol (111) were isolated from Solanum laciniaturn.The presence of diosgenin together with solasodine in Solanum laciniatum has been reported by some authors (SCHREIBER 1957, 1963) ,and MADAJEVA et al. (1965). SCHREIBER (1957), SANDER (1961) and FAYEZ et al. (1967,1967a) reported the presence of dihydroxylic sapogenins in a number of Solanurn species, but asfar as the present author is aware, this is the first reported occurrence of chlorogenin in S. laciniatum. The joint occurrence of spirostanes in spirosolane-bearing plants is now recognized as to be expected from the common biogenetic pathway. SANDER (1961, 1963) and WILLUHN (1966, 1967) reported that in Solanurn and Lycopersicon species the spirosolane content of their fruits was found to decrease gradually during ;he ripening process, in contrast, the spirostanes do not disappear, but their content more or less increases, suggesting an interconversion of spirosolanes into spirostanes. The biogenetic relation between the commoner Solanum alkaloids and monohydroxylic spirostanes is both evident and understandable from a consideration of their hydroxyl content and their stereochemistry at C-5, C-22 and C-25. The existence of dihydroxylic spirostanes in Solanum plants indicates that the relation may be further complicated by an additional hydroxylation or dehydroxylation mechanism induced by enzymes.In the present study, the processing of the plant material was conducted as follows: The defatted powdered plant material (leaves and stalks) was extracted by hot ethanol. The concentrated alcoholic extract was hydrolyzed with mineral acid and the precipitated material was collected by filtration. Inspection of the residue on TLC using silica gel, as adsorbent and chloroform-methanol (19 : I), as solvent. A chromatoplate sprayed with Dragendorff's reagent revealed only one spot (orange). Another plate sprayed with the p-anisaldehyde reagent revealed 3 spots Rf 0.25 (yellow); Rr 0.32 (blue) and Rr 0.7 (yellow). It was previously shown that steroid sapogenins may conveniently be differentiated from steroid alkaloids on silica gel chromatoplates by the use of p-anisaldeyde spray reagent (FAYEZ et al. 1967). Pure solasodine was obtained from the residue by extraction with chloroform, which removed the sapogenins only as solasodine hydrochloride is insoluble in chloroform. Re-extraction of the residue with methanol, then addition of ammonia to pH 10 liberated the aglycone. Addition of water precipitated crude solasodine. Pure solasodine was extracted from this crude precipitate by chlorofornl. Inspection of this solution on TLC using above mentioned conditions revealed one spot Rt 0.32 identical in location and colour with a spot of authentic solasodine, besides 2 minor spots Rr 0.25 and Rr 0.7. Evaporation of the chloroform extract to dryness and dissolving the material obtained in methanol, charcoaling and crystallization from methanolwater afforded long plates m. p. 199- 200" C; [a],, - 104 (chloroform) undepressed with authentic solasodine.Evaporation of the chloroform extract afforded a residue containing two sapogenins as shown by TLC. This mixture was resolved on an alumina column. Elution with petroleum ether- benzene (3 : 7) afforded diosgenin as revealed by TLC (three developments) on 2% silver nitrate-impregnated silica gel chromato- ~lates, as developer was used a mixture of dichloromethane-acetone (98 : 2) and spraying with p-anisaldehyde reagent, revealed a yellow spot Rr 0.63 identicalin location and colour with authentic diosgenin. Evaporation of the eluent afforded a solid, which after crystallization from chloroform-methanol gave colo~irless plates m. p. 192-19.5' C; [u]~ - 121' (chloroform). The presence of the double bond was proved by the appearence of a yellow colour after addition of a drop of tetranitromethane to a small portion of the material in chloroform. IR spectra showed band near 920 cm-I stronger than that near 900 cm-' as is usual with the 25 D sapogenins. The spiroketal side chain was porved by the four bands near 866, 900, 922 and 982 cm-'. The acetate derivative m. p. 187-189O C undepressed with authentic diosgenin acetate.Elution with benzene afforded chlorogenin as shown by TLC on 5% silver nitrate impregnated silica gel and developing with dichloromethane-acetone (6 : 4) a spot Rr 0.55 identical in colour (yellow) and location with authentic chlorogenin. After evaporation of benzene, the solid obtained was crystallized from chloroform aqueous methanol to afford chlorogenin as colourless needles m. p. 275-278", [u]~ -65 (chloroform), undepressed with authentic chlorogenin. This identity was further confirmed by the comparison of the IR spectra of the isolated compound and chlorogenin. The two spectra were found to be identical in every detail.