cis,trans-Tetrahydromitchelladione

Abstract

Abstract. C3oH4402, M r : 436.68, orthorhombic, P21212 ~, a = 18.723(9), b = 12.334(6), c = 11.300(6) A,Z= 4, Dm= 1.100 (2), Dx = 1.112 Mg m -a. The structure was solved by direct methods with diffractometer data. Refinement of the structure gave a final value of R = 0.073 on F for 1325 non-zero reflections. The sesquiterpene dimer from the wood oil of Eremophila mitchelli exhibits a conformation in which the centres of the two halves of the molecule are as close as possible, most probably due to a dipolar interaction between them.

Chemical composition and cytotoxicity of oils and eremophilanes derived from various parts of Eremophila mitchellii Benth. (Myoporaceae)

“…Their isolation and characterisation is complicated because they share similar molecular weights and many were found to co-elute with the major compounds throughout HPLC (both NP and RP) and GC-MS (both polar and apolar systems). Several structural analogues of the eremophilones have been reported in the literature including the aldehyde 2 (Abel and Massy-Westropp, 1985), isoeremophilone (11) (Chetty and Zalkow, 1969), alloeremophilone (12) (Bates and Paknikar., 1966) and the dimers 7 and 8 (Lewis et al, 1979(Lewis et al, , 1982. The analogues, if present, appear to be very minor constituents.…”

Natural disesquiterpenoids

“…104 Tetrahydromitchelladione 104, a novel eremophilane dimer with an unusual carbon skeleton, was isolated from the wood oil of Eremophila mitchelli. 105 Further research resulted in the isolation of two more dimers, 105-106, possessing the same skeleton as 104. 106 A symmetrical eremophilane dimer 107 was identified as a component of the rhizomes of Farfugium japonica.…”

Syringenes M – Q, Eremophilane Sesquiterpenoid Dimers from the Peeled Stems ofSyringa pinnatifolia

“…There were a few eremophilane dimers reported from several genera such as Ligularia, [18 -20] Incarvillea, [21] and Eremophila, [22] but none has been described in Oleaceae except for syringenes AÀ L from SP. [15] Therefore, compared to humulane such as zerumbone, and alashanoids AÀ S, [9,11,12,14] dimeric eremophilane might serve as a more characteristic chemical marker to distinguish SP from other Syringa species, which provides another chemical evidence to support the classification controversy for previous methods.…”