hydrocarbons (predominantly C25, C27 and C29 alkanes), the ethyl 

 esters of linoleic and linolenic acids, and a mixture of C29-C31 

 sterols (chiefly /3-sitosterol) esterified with C,^ and C,^ fatty acids 

 were obtained. A neutral chloroform fraction yielded, in addition 

 to small amounts of the above compounds, some free fatty acids 

 and the glucosides and glucoside palmitic/ oleic acid esters of 

 j3-sitosterol and stigmasterol — all known compounds. 



It was in the alcohol extract that the interesting chemistry of the 

 plant was revealed. Concentration, partition between aqueous 

 and organic phases at selected pH values, followed by chromato- 

 graphic separation and crystallization, yielded several com- 

 pounds. The odor principle was identified as 3-hydroxy-4,5- 

 dimethyl-2(5H)-furanone (IV): the first report of this compound 

 in a plant. It had been recognized previously as a constituent of 

 aged sake formed during the aging process rather than as a 

 constituent of sake itself (Takahashi, 1976); and as a constituent 

 of sugarcane molasses (Tokimoto, 1980). It had been synthesized 

 even earlier in a study of food flavorings (Sulser, 1972) and was 

 found to have one of the lowest threshold values known for food 

 flavoring compounds, perceivable in concentrations as low as 

 0.01 ppb. It is also attractive to cockroaches, houseflies and ants, 

 and has been described as having the flavor of walnuts. A structu- 

 rally similar ketone, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 

 has been reported from pineapple, contributing a "burnt pineap- 

 ple" note to the overall flavor of the fruit (Rodin, 1965). 



Two closely related aminolactones, 3-amino-4,5-dimethyl- 

 2(5H)-furanone (III) and its saturated analog (II) were also iso- 

 lated from the flowers and, to our knowledge, are likewise new to 

 the plant kingdom. The presence in Q.funebris of these lactones is 

 of more than passing interest in view of a recent publication on 

 the anticonvulsant activity and potential clinical usefulness of a 

 group of alkyl-substituted butyrolactones (Klunk, 1982) structu- 

 rally related to them. It is not unlikely that some of the folk- 

 medical use of the flowers is referable to these compounds. 

 Further, the hypothermic and behavioral effects reported for 

 7-hydroxybutyric acid itself (Snead, 1978) suggest that the utili- 

 zation of Q. funehris preparations as antipyretics and possibly as 

 an hallucinogen may not be at all unreasonable. Pharmacological 



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