Sesquiterpenoids—III

Dendocarbin A: a sesquiterpene lactone fromDrimys winteri

“…Drimys winteri (Winteraceae) is a native tree of Chile, sacred for the native people (Araucanian) due to its medicinal properties, including bactericidal, antifungal and insecticidal activity (Kubo et al, 2005;Jansen & de Groot, 2004). The main secondary metabolites in its barks are drimane sesquiterpenoids which have been described by Appel et al (1963). On the other hand, the main scope of the present report, the natural compound dendocarbin A, (I), even if not novel, has been treated only tangentially in the literature.…”

6,6,9a-Trimethyl-5,5a,6,7,8,9,9a,9b-octahydronaphtho[1,2-c]furan-1(3H)-one

“…For related literature, see: Almeida et al (2001); Appel et al (1963); Cremer & Pople (1975); Cruz et al (1973); Harinantenaina et al (2007); Sierra et al (1986).…”

“…In Chile, Drimys winteri (canelo) is used by the indigenous Mapuche in the treatment of several stomachal diseases, ulcers and hemorrhages (Almeida et al, 2001). Chemical studies has shown the presence of a variety of sesquiterpenes with drimano skeleton (Appel et al, 1963) and flavonoids. Some of these compounds have shown significant antibacterial, antifungi, antitumor and insecticide properties (Cruz et al, 1973;Sierra et al, 1986).…”

A monoclinic form of dendocarbin A: a borderline case of one-dimensional isostructural polymorphism

“…Due to its medicinal properties (such as antifungal, insecticidal and bactericidal) (Kubo et al, 2005;Jansen & de Groot, 2004), the tree, locally called Canelo, was considered sacred by the native Araucanians. Drimane sequiterpinoids, found in the bark, have been described in detail previously (Appel et al, 1963). Dendocarbin A belongs to this sesquiterpinoid family but has been infrequently discussed in the literature.…”