Harvesting canthinones: identification of the optimal seasonal point of harvest of Zanthoxylum chiloperone leaves as a source of 5-methoxycanthin-6-one

Abstract

This article is focused on the seasonal variation in the contents of 5-methoxycanthin-6-one from the leaves of Zanthoxylum chiloperone (Rutaceae). Based on the pharmacological interest presented by 5-methoxycanthin-6-one, its seasonal variation in Z. chiloperone leaves was analysed in order to determine the best time for harvesting, optimising the 5-methoxycanthin-6-one content. The seasonal dynamics of canthinone alkaloids can be the key to improve the isolation from natural sustainable sources, such as leaves. Complementarily, this study describes the phytochemistry of leaf from this Ruraceae species.

Phytoelectrochemical analysis of Zanthoxylum chiloperone

“…Figure shows the square wave voltammograms of a microparticulate film of canthin‐6‐one ( L1 ) with those obtained for extracts from leaves, stem bark and roots of Zanthoxylum chiloperone . Consistently with prior HPLC data (Cebrián‐Torrejón et al ; Ferreira et al ; Cebrián‐Torrejón et al ), L1 is the prevailing compound in the stem bark extracts whereas L3 predominates in the root extracts. Interestingly, this voltammetry can be reproduced using microparticulate deposits directly of powdered materials from different parts of the plant transferred by abrasion onto the surface of graphite electrodes following typical VMP procedures (Scho Scholz et al ; Scholz et al ).…”

“…Coincidentally with different studies on plants from other taxons (Wallace and Eigenbrode ; Bapela et al ), we obtained evidence that the composition of the extracts from the leaves of Z. chiloperone experienced significant seasonal variations in the contents of 5‐methoxycanthin‐6‐one ( L2 ) (Cebrián‐Torrejón et al ). Given the possibility of obtaining therapeutic formulations from different parts of the plants, controlling the influence of age, seasonality, rainfall, temperature, and altitude, among other factors, on the metabolite profile is an important analytical task (Gobbo‐Neto and Lopes ).…”

“…After solvent evaporation in air, the electrode was inserted into the electrochemical cell and electrochemical runs were performed. Similar procedures were used from dry extracts of different parts of the plants prepared as already described (Cebrián‐Torrejón et al ).…”

Total Synthesis of Bioactive Canthine Alkaloid Cordatanine Comprising in Situ Double Oxidative Aromatization of Tetrahydrocarbazole

“…11,12 The total synthesis of cordatanine and zanthochilone is a challenging task and is of current interest due to their structural features, potential bioactivities, and the seasonal changes that affect their concentration in natural sources. 8−13 Recently, Wu et al accomplished the synthesis of cordatanine in four steps with an 8% overall yield and unambiguously confirmed its revised structural assignment; 9,10,14 the synthesis of zanthochilone, however, is awaited. In continuation of our studies on the use of cyclic anhydrides to synthesize bioactive natural products, 15−19 we herein report a facile regioselective approach to cordatanine and attempted synthesis of zanthochilone from the readily available common precursors, tryptamine and methoxymaleic anhydride 20 (Schemes 1–4).…”

Fruitful Decades for Canthin-6-ones from 1952 to 2015: Biosynthesis, Chemistry, and Biological Activities

“…The canthin-6-one alkaloids, a subclass of β-carboline alkaloids with an additional D ring, have been isolated from various plants, principally those in the Rutaceae [1,2,3,4,5,6,7,8] and Simaroubaceae [9,10,11,12,13,14,15,16,17] families, but also those in the Amaranthaceae [18], Caryophyllaceae [19] and Zygophyllaceae [20] families, and more recently from fungi [21] and marine organisms [22]. Canthin-6-one ( 1 ) (Figure 1) was first isolated in 1952 by Haynes et al [23] from the Australian tree Pentaceras australis .…”