Cryptocarya massoia

Massoilactone (45) is the major component of the bark oil of Cryptocarya massoia (Lauraceae) (1, 74). The absolute configuration of (-)-massoilactone is (R) at C-5, which is enantiomeric to parasorbic acid (29, 78). An analogous lactone (46) was also isolated from the same plant (22). Massoi bark has been used for many centuries as a constituent of native medicines. The sedative action expected from the structural similarity between massoilactone and active Kawa-type lactones is dubious (9). (-)-Massoilactone has been isolated from cane molasses as one of, and the most characteristic, sugary-flavor substances (48). This compound was also obtained from two species of formicine ants of the genus Cam-ponotus (22). This powerful skin-irritating compound might be responsible for the defensive factor secreted by the ants. 

Cavill G W K, Clark D V, Whitefield F B 1968 Insect venoms, attractants, and repellents. XL Massoilactone from two species of formicine ants, and some observations on constituents of the bark oil of Cryptocarya massoia. Aust J Chem 21 1819-1823... 

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