Phytochemical Analysis of Alkaloids From the Chilean Endemic Tree Cryptocarya Alba

Abstract

A phytochemical study of the roots and aerial parts of Cryptocarya alba (Mol.) Looser (Lauraceae), an endemic Chilean tree and the southernmost Cryptocarya species, led for the first time to the isolation and unambiguous characterization of four known alkaloids by NMR techniques: boldine, laurolitsine, laurotetanine and norglaucine, in addition to the previously identified reticuline, and the identification via UHPLC-MS of seven more alkaloids, coclaurine, N-methylcoclaurine, norreticuline, isocorydine, N-methyllaurotetanine, predicentrine and glaucine. In spite of this fairly broad variety of benzyltetrahydroisoquinolines and aporphines, the concentrations of these alkaloids in the different organs of C. alba are quite low, which is in contrast with the sometimes generous yields of alkaloids in this genus.

Antimicrobial Activity of Extracts of Two Native Fruits of Chile: Arrayan (Luma apiculata) and Peumo (Cryptocarya alba)

“…In agreement with our results, Timmermann et al [26], also reported flavonoids (isorhamnetin, kaempferol, quercetin, and their glycosides) and chlorogenic acid present in leaves extract of peumo. In contrast to the previous report of Castro-Saavedra et al [27], no alkaloid was detected by U-HPLC/MS. Both fruit extracts showed the presence of quercetins and their derivatives.…”

Variation of Secondary Metabolites in the Aerial Biomass of Cryptocarya alba

“…The alkaloid composition of the branches (wood and bark) is largely consistent with results obtained previously. 10 In 67% of the individuals, laurolitsine was the most abundant wood alkaloid, while laurotetanine and reticuline predominated in the bark. In 88% of the trees, reticuline was the major bark alkaloid, but exceptions were found in the southern population, with laurotetanine predominating in the bark of 6 individuals, and reticuline in the wood of another 7, while only 2 individuals had both high bark laurotetanine and wood reticuline.…”

“…31 In our earlier work on C. alba, the best results for leaves were obtained from young saplings (<3 years old). 10 Therefore, a detailed analysis of farmed individuals was deemed important. The amount of sunlight can influence the yield of some alkaloids so we compared subpopulations with different degrees of shading.…”

“…9 Until a couple of years ago, C. alba leaves and bark were only known to contain reticuline, 4 but low concentrations of aporphines have been identified recently. 10 The fruit contains cryptofolione and a methoxylated derivative (α-pyrones). 11 The essential oil (EO) of the leaves analyzed presents variations.…”

“…Nevertheless, it is possible to find higher concentrations in this species, for example, in old trees, where some individuals had more than 500 µg/g DW. 10 Although higher concentrations have been reported in California poppy ( Eschscholzia californica ), 24 in the roots of Litsea cubeba, 25 and in the wood and bark of boldo ( P. boldus ), 26 a significant advantage of C. alba bark is that reticuline is the major alkaloid in this abundant species, making its purification simpler. Both reticuline enantiomers are intermediates in the biosynthesis of most isoquinoline alkaloids and are therefore very interesting as precursors in potential biotechnological processes.…”