Alkaloids from Chilean species of the genus Rhodophiala C. Presl (Amaryllidaceae) and their chemotaxonomic importance

Abstract

The family Amaryllidaceae is widely distributed from temperate to tropical regions. Amaryllidaceae species from the subfamily Amaryllidoideae can biosynthesize alkaloids with important physiological effects. Rhodophiala C. Presl is one of the native genera of Amaryllidoideae of Chile, Argentina, Paraguay, Uruguay and Brazil. However, despite the diversity of this genus in Chile, their alkaloids have only been studied previously in one species of this country. The present work aims to analyze the alkaloid profi les and chemotaxonomically compare three other Chilean species of Rhodophiala: Rhodophiala bagnoldii (Herb.) Traub, Rhodophiala pratensis (Poepp.) Traub and Rhodophiala volckmannii Phil. Bulb extracts were analyzed by means of gas chromatography-mass spectrometry (GC-MS) and alkaloids were characterized according to retention time and fragmentation pattern. The skeleton type alkaloids detected were lycorine, crinine, galanthamine, homolycorine, tazettine and montanine. All analyzed species showed different alkaloid profi les, indicating these compounds can be used as a chemotaxonomic tool. Furthermore, the alkaloid types detected in this genus have multiple reported biological properties and these species can constitute new sources of important medicinal products.

Genetic Diversity and Chemical Profile of Rhodophiala bifida Populations from Brazil

“…Traub, and R. volckmannii Phil. (Lizama-Bizama et al 2018). The results obtained in this work and the information described in the literature corroborate the finding that montanine-type alkaloids could be characteristic of the Rhodophiala genus.…”

In vitro micropropagation and alkaloids analysis by GC–MS of Chilean Amaryllidaceae plants: Rhodophiala pratensis

“…Previous studies in species of the Rhodophiala genus have reported the presence of 37 alkaloids characteristic of the family Amaryllidaceae and 40 compounds corresponding to alkaloids, which according to their fragmentation patterns would present a skeleton of the lycorine type, haemanthamine, tazettine, homolycorine, galanthamine, montanine and narciclasine . Our study contributes to the knowledge of the alkaloids present in the species R. pratensis , which had not been included in the previously reported studies.…”

“…which used the areas of different alkaloids and standardised with the area of codeine (internal standard).Previous studies in species of the Rhodophiala genus have reported the presence of 37 alkaloids characteristic of the family Amaryllidaceae and 40 compounds corresponding to alkaloids, which according to their fragmentation patterns would present a skeleton of the lycorine type, haemanthamine, tazettine, homolycorine, galanthamine, montanine and narciclasine 9,14,15. Our study contributes to the knowledge of the alkaloids present in the species R. pratensis, which had not been included in the previously reported studies.When comparing the amount and type of alkaloids obtained from both wild bulbs and those obtained by in vitro culture, it can be observed that wild plants have 34 alkaloids whereas in vitro bulbs show only 12.…”

Hippeastrum escoipense (Amaryllidaceae, Amaryllidoideae): una nueva especie críptica del noroeste de Argentina

“…de las ecorregiones del Cerrado y la Caatinga en los estados brasileños de Bahía, Minas Gerais y Tocantins (Büneker et al, 2016;García et al, 2019;Dutilh et al, 2020) Dentro de las Amaryllidaceae, los representantes de la subfamilia Amaryllidoideae se caracterizan por sintetizar un gran número de alcaloides cuyas variaciones estructurales y relaciones biosintéticas hacen de estos compuestos un buen carácter quimiotaxonómico (Takos & Rook, 2013;Berkov et al, 2020). Estudios fitoquímicos realizados en algunos géneros de Amaryllidoideae revelan diferencias entre los patrones alcaloideos que permiten definir quimiotaxonómicamente a las especies ante la falta de rasgos morfológicos (Berkov et al, 2008(Berkov et al, , 2011Lizama-Bizama et al, 2018). Akram et al (2021) demostraron, en el caso de Narcissus pseudonarcissus L., que la edad del bulbo así como la locación del cultivo son factores que afectan solamente los niveles de alcaloides y no siempre de modo significativo.…”