The Chemistry of Brazilian Lauraceae. XLVII. Ferulic esters from Endlicheria and Ocotea species

Abstract

A specimen from the Torquato-Tapajós Highway, km 133, Amazonas, voucher Herbarium INPA 48255, was identified tentatively with Endlicheria anomala Nees (Lauraceae) by Dr. W. A. Rodrigues. A trunk wood sample (1 . 2 kg) was extracted with ethanol. The chloroform-benzene 1:1 soluble part (15 g) of the extract (38 g) was chromatographed on a silica (360 g) column. Elution with CsH6 gave, in order, fatty ester (2 g, oil). n-tetracosyl ferulate [347 mg, mp 65-67., (CsHs)]. n-tetracosanol [93 mg, 71-73° (CsHs)] and sitosterol [1230 mg, 138-140" (EtOH)]. Elution with CsHõCHCb 9:1, C6HõCHCb 8:2 to 0:10, CHCI:r -AcOEt 9:1 and AcOEt-MeOH 9:1 gave respectively stearic acid [70 mg, mp 68-69° (CsH6-EtOH)], a stearate of a fatty alcohol [58 mg, mp 86-88° (EtOH-CHCb)], a ferulate of a fatty alcohol [90 mg, mp 77-78° (EtOH-CHCb)] and a glycoside [28 mg, mp 291-293° (EtOH-CHCb)]. n-Tetracosyl ferulate was identifíed by spectral data (IR, 1 H NMR, MS) and direct comparison with an authentic sample [Franca et a/ .. 1975]. n-Tetracosanol was identified by direct comparison with the alcohol obtained by saponification of the ferulate. Sitostarol and stearic acid were identified by direct comparison with authentic samples . Saponification of the additional esters , mp 86-88° and 77-78°, gave respectively stearic acid, mp. 69-70°, and ferulic acid, 169-170°. The simplicity of composition of E. anomala contrasts w ith the diversity and complexity of cinnamate derived metabolites of Lauraceae species described in ali previous reports o f the present series [for part XLVI see Diaz et a /., 1977] . In this respcct. the species, nevertheless, does not occupy ~ peculiar position. Absence of detectable quantities of cinnamate derived metabolites and accumulation of ferulic acid was noted additionally for the following species.