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Phytochemistry and Biological Properties of Drimys Winteri JR Et G. Forster Var Chilensis (DC) A

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BOLETIN LATINOAMERICANO Y DEL CARIBE DE PLANTAS MEDICINALES Y AROMÁTICAS © / ISSN 0717 7917 / www.blacpma.ms-editions.cl Revisión / Review Phytochemistry and biological properties of Drimys winteri JR et G. Forster var chilensis (DC) A. [Fitoquímica y propiedades biológicas de Drimys winteri JR et G. Forster var chilensis (DC) A.] Orlando Muñoz1, Jorge Tapia-Merino2, Wolf Nevermann, & Aurelio San-Martín3 1Departamento de Quimica, Facultad de Ciencias, Universidad de Chile, Ñuñoa, Santiago, Chile 2Departamento de Ciencias Químicas y Biológicas, Facultad de Salud, Universidad Bernardo OHiggins, Santiago, Chile 3Departamento de Ciencias y Recursos Naturales, Facultad de Ciencias, Universidad de Magallanes, Punta Arenas, Chile Abstract: Drimys winteri JR et G. Forster var chilensis (DC) A. is a tree native to central and southern Chile. Also it found in part of Argentina. It is abundant in wet swampy localities from sea level to an altitude of 1700 m. This tree is sacred for the Mapuche culture; it is used in folk medicine in such as Reviewed by: inflammatory and painful processes. Phytochemical studies have demonstrated that this plant contains Arnaldo Bandoni Universidad de Buenos Aires mainly sesquiterpenes of the drimane type, flavonoids, essential oils, phytosterols and some lignans. Argentina These drimanes have attracted interest because of their antifeedant, plant growth regulation, cytotoxic, antimicrobial and insecticidal properties. The objective of this review is to establish clearly the Ali Parlar phytochemistry and biological activity of Drimys winteri JR et G. Forster var chilensis (DC) A. Articles Adiyaman University based on other varieties are not considered. Turkey Keywords: Drimys winteri; Sesquiterpenes; Essential oils; Lignans; Flavonoids; Biological properties. Correspondence: Aurelio SAN MARTIN [email protected] Section Review Received: 25 May 2020 Accepted: 25 January 2021 Accepted corrected: 29 January 2021 Resumen: Drimys winteri JR et G. Forster var chilensis (DC) A. es un árbol nativo del centro y sur de Published: 30 September 2021 Chile. Tambien se encuentra en parte de Argentina. Es abundante en localidades pantanosas y húmedas desde el nivel del mar hasta una altitud de 1700 m. Este árbol es sagrado para la cultura mapuche. Se utiliza en la medicina popular para tratar enfermedades como procesos inflamatorios y dolorosos. Los estudios fitoquímicos han demostrado que esta planta contiene principalmente sesquiterpenos del tipo Citation: drimano, flavonoides, aceites esenciales, fitoesteroles y algunos lignanos. Estos drimanos han despertado Muñoz O, Tapia-Merino J, interés debido a sus propiedades antialimentarias, regulación del crecimiento de las plantas, propiedades Nevermann W, San-Martín A. citotóxicas, antimicrobianas e insecticidas. El objetivo de este examen es establecer claramente la Phytochemistry and biological properties of fitoquímica y la actividad biológica de Drimys winteri JR et G. Forster var chilensis (DC) A. No se Drimys winteri JR et G. Forster var chilensis (DC) A. Bol Latinoam Caribe Plant Med Aromat consideran los artículos basados en otras variedades D. winteri var winteri. 20 (5): 443 - 462 (2021). https://doi.org/10.37360/blacpma.21.20.5.33 Palabras clave: Drimys winteri; Sesquiterpenos; Aceites esenciales; Lignanos; Flavonoides; Propiedades biologicas. 443 Muñoz et al. Properties of Drimys winteri JR et G. Forster var chilensis INTRODUCTION (24 ft) by 6 m (19ft) at a medium rate. It is hardy to Plants of the genus Drimys, (Winteraceae) are widely zone. It is in leaf all year, in flower from January to distribute all over the America (from Mexico until June. The species is hermaphrodite. Suitable for: light Chile and part of Argentina). The species, descrited (sandy) and medium (loamy) soils and prefers well- for this continent are: Drimys angustifolia Miers drained soil. Suitable pH: acid and neutral soils. It (south of Brasil), Drimys brasiliensis Miers (Brasil can grow in semi-shade (light woodland). It prefers until south of México), Drimys confertifolia Phil. moist soil. The plant can tolerate strong winds but not (endemic plant of Juan Fernandez Island, Chile), maritime exposure (Jordan, 2005). There are three Drimys andina (Reiche) R. A. Rodr. & Quez. (syn D. species of Drimys in Chile: D. winteri (two varieties winteri var. andina) endemic of Chile, Drimys have been described) and D. andina Reiche granadensis L.f. south México until south of Perú), (Rodriguez & Quezada, 1991). The most abundant is Drimys winteri J. R. Forst. & G. Forster var chilensis the tree Dwch, whereas D. andina is a shrub and less (DC) A. (Chile, and south Argentina), and Drimys common (Marticorena & Quezada, 1985; Muñoz- winteri var winteri occurring in Southwestern Concha et al., 2007). Currently two arbnorescent Patagonia (45º44’- 55º58’S) (Rodriguez & Quezada, species are recognized in Chile: D. winteri JR Forst et 1991; Ruiz et al., 2008). Most of these species, are G. Forst with two varieties, D. winteri var. winteri traditionally used as wild vegetables and as a occurring in Southwestern Patagonia (45°44¨- therapeutic agent. 55°58´S) and D. winteri var. chilensis (DC.) A. Gray The genus Drimys includes approximately being widespread in Chile and Argentina (30°20¨-46° between six and eight Central and South American 25¨S) (Ruiz et al., 2008). According to the literature, species that are distributed from Mexico to Navarin the variety chilensis it is not found in Brazil (Santos Island (Molina et al., 2016). One species (Drimys et al., 2017) confertifolia Phil. is endemic to the Juan Fernandez The objective of this review is to establish Islands (Silva et al., 1992). Of these species, only clearly the phytochemistry and biological activity of Drimys winteri JR et G. Forster var chilensis Drimys winteri JR et G. Forster var chilensis (DC) A. (DC) A. (Dwch) (Figure No. 1) commonly called As in many studies the variety analyzed is not canelo is well known in cultivation (Hernandez et al., specified but in its totality corresponds to samples 1996; Jordan, 2005). It is found up to 1200 m above collected in Chile (except from Patagonia), we have sea level and between latitude 32° south and Cape assumed that the samples are from Dwch. Articles Horn at latitude 56° south in Patagonia. Drimys based on others varieties, are not considered. winteri JR is an evergreen shrub growing to 7.5 m Figure No. 1 Drimys winteri JR et G. Forster var chilensis (DC) A. (Vogel et al., 2008) (Photo S. Teillier) Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas / 444 Muñoz et al. Properties of Drimys winteri JR et G. Forster var chilensis D. winteri JR et G. Forster var chilensis (DC) A. is a harvested in autumn and winter and is dried for later sacred plant to the indigenous Mapuche people, who use. Another important use of bark infusion is in the use its aerial parts for the treatment of dermatitis, treatment of rheumatic illnesses (Muñoz et al., 2015). stomach pain, toothache, tumors, and other illnesses (Muñoz & Barrera, 1981; Muñoz et al., 2001; Phytochemical Analysis Estomba et al., 2006). Extracts of the stem bark have Phytochemical studies of the extracts of aerial parts long been used to treat human (Muñoz & Barrera, of Dwch performed several decades ago in Chile 1981) and bovine diseases: gastrointestinal (Appel et al., 1964; Appel et al., 1960; Brown, 1994) nematodes, (Rodriguez et al., 2005). In the past, the reported phytonutrients and pest repellent agents stem bark of Dwch was exported to Europe as an (Jansen & de Groot, 2004; Zapata et al., 2009; antiscorbutic medicine (Muñoz et al., 2001; Jordan, Monsálvez et al., 2010). Phytochemical reports on 2005). The tree is also used for commercial purposes, the chemical composition of continental Dwch in wood production, crafts, manufacturing and the indicated the presence of tannins, flavonoids, pulp industry, due to the high quality of its fibers. Its essential oils, drimane-type sesquiterpenes, architectural characteristics and natural resistance to sesquiterpene lactones (Muñoz et al., 2001), lignans insects and microorganisms are advantageous for and phytosterols (Muñoz et al., 2015). playgrounds in parks and gardens in a wide range of climatic conditions. The wood of this species is Drimane-type sesquiterpenes highly valued and used to manufacture furniture and The name drimane was proposed for the saturated musical instruments as well as to protect crops hydrocarbon with the structure and absolute (Rodriguez, 1998; Franco et al., 2006; Monsálvez et configuration depicted in Figure No. 2 (Jansen & de al., 2010). Furthermore, extracts of aerial parts of Groot, 1991; Jansen & de Groot, 2004). This Dwch have shown industrial applications in products structure is related to the sesquiterpene drimenol, such as cosmetics (Rodriguez, 1998; MINSAL, isolated from the bark of Dwch Forst. reported by 2010), phytonutrients and pest repellent agents Appel (Appel, 1948). The structures of the (Jansen & de Groot, 2004; Zapata et al., 2009; sesquiterpenes isolated up to now from Dwch (Figure Monsálvez et al., 2010); the bark produces a pungent No. 2), and the numbering of the carbon skeleton bitter herb tonic that relieves indigestion. It is follows the system established by Djerassi (Djerassi antiscorbutic, aromatic, febrifuge, and also used as a et al., 1954). parasiticide (Moya & Escudero, 2015). The bark is Compound R1 R2 References Confertifolin CH2 H Appel et al., 1960 Valiviolide CH2OH H Appel et al., 1963 Fueguin CH2OH OH Appel
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  • Reconstructing the Basal Angiosperm Phylogeny: Evaluating Information Content of Mitochondrial Genes

    Reconstructing the Basal Angiosperm Phylogeny: Evaluating Information Content of Mitochondrial Genes

    55 (4) • November 2006: 837–856 Qiu & al. • Basal angiosperm phylogeny Reconstructing the basal angiosperm phylogeny: evaluating information content of mitochondrial genes Yin-Long Qiu1, Libo Li, Tory A. Hendry, Ruiqi Li, David W. Taylor, Michael J. Issa, Alexander J. Ronen, Mona L. Vekaria & Adam M. White 1Department of Ecology & Evolutionary Biology, The University Herbarium, University of Michigan, Ann Arbor, Michigan 48109-1048, U.S.A. [email protected] (author for correspondence). Three mitochondrial (atp1, matR, nad5), four chloroplast (atpB, matK, rbcL, rpoC2), and one nuclear (18S) genes from 162 seed plants, representing all major lineages of gymnosperms and angiosperms, were analyzed together in a supermatrix or in various partitions using likelihood and parsimony methods. The results show that Amborella + Nymphaeales together constitute the first diverging lineage of angiosperms, and that the topology of Amborella alone being sister to all other angiosperms likely represents a local long branch attrac- tion artifact. The monophyly of magnoliids, as well as sister relationships between Magnoliales and Laurales, and between Canellales and Piperales, are all strongly supported. The sister relationship to eudicots of Ceratophyllum is not strongly supported by this study; instead a placement of the genus with Chloranthaceae receives moderate support in the mitochondrial gene analyses. Relationships among magnoliids, monocots, and eudicots remain unresolved. Direct comparisons of analytic results from several data partitions with or without RNA editing sites show that in multigene analyses, RNA editing has no effect on well supported rela- tionships, but minor effect on weakly supported ones. Finally, comparisons of results from separate analyses of mitochondrial and chloroplast genes demonstrate that mitochondrial genes, with overall slower rates of sub- stitution than chloroplast genes, are informative phylogenetic markers, and are particularly suitable for resolv- ing deep relationships.