Eremophila mitchelli

Eremophila mitchelli is a rich source of various eremophilane sesquiter-penoids and to those already known can now be added the dienone (285). The chemistry of the eremophilane-related sesquiterpenoid bakkenolide-A (286) has been published. ... 

Remarkably few triterpenes have been isolated from Eremophila species. Oleanolic acid and ursolic acid were isolated from E. caerulea (134) and 3-ept-oleanolic acid from E. platycalyx (16). Two unusual triterpenes (218 and 219) have been isolated from the wood oil of Eremophila mitchelli. Their structures were determined from a combination of spectroscopic techniques, aided by an X-ray diffraction study of the tetrahydro-derivative (220) of the dione (218). The... 

The Australian tree Eremophila mitchelli gave its name to the eremophilanes with both methyl groups in p-positions of the decalin bicycle flie wood of Eremophila mitchelli contains various eremophiladienones. Non-toxic metabolites of the fungus... 

Constituent of oil of Eremophila Mitchelli. Prisms from MeOH. M.p. 102-3°. [a]j4gi + 94° ill MeOH. Readily sol. most org. solvents e.vcept MeOH, EtOH. Insol. HaO. Reduces Fcliling s. 

Although eremophUone was isolated from an Australian shrub (Eremophila mitchelli) in the 1930s, it took nearly a decade before its structure was elucidated. The problem, in part, was that it does not obey the isoprene rule (a methyl group... 

Of the rearranged eudesmanes, eremophilanes (216) are most prolific ( 150 derivatives). The subject was reviewed in 1977 (314). Two stereochemical classes, 239 and 240, have been recognized in principle, these are related to the eudesmane (222) and intermedeane types (225), respectively. The first member of this class to be characterized was eremophilone (241), which occurs in the wood oil of the Australian tree Eremophila mitchelli, along with other related compounds. This was the first terpene structure not consistent with the isoprene rule and Robinson (327) invoked a 1,2-methyl shift from a eudesmane precursor to rationalize this structure. (-)-Eremoligenol (242) is a component of roots of Ligularia fischeri, while isovalencenic acid (243) has been isolated from vetiver oil. (-h)-Nootkatone (244) was first isolated from the heartwood of Alaska-cedar... 

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