Estudos dos constituintes químicos das espécies Hemerocallis fulva e Ocotea cymbarum

Abstract

From the bulbs of Hemerocallis fulva an herbacius plant of the Liliaceae family, five compounds have been isolated, β-sitosterol (Hf-2, 6) and four anthraquinones: 1,8-dihidroxy -3-methylanthraquinone (crisophanol, Hf-1, 4), 1,6,7-trihidroxy- 3-hidroxymethylanthraquinone (Hf-3, 11, which was isolated contaminated with another compound, possibly, 1,6,7-trihidroxy -3-methylanthraquinone, 12), 1,5-dihidroxy-2,6-dimethoxy-3- methylanthraquinone (Hf-4, 14), also isolated in mixture with probably, 1,5-dihidroxy-3-methylanthraquinone, 15) and 1-methoxy -5,6-dihidroxy-3-methylanthraquinone (Hf-5, 17). The structuresof the anthraquiones were determinated by analises of Ultraviolet, Infrared, Nuclear Magnetic Ressonance (1H) and Mass spectrals data. Only β-Sitosterol was identified by direct comparation with real sample through chromatographic methods and physicals constants. The obtainment of the acetoxy derivate from Hf-1 aided in it's structural determination. A table is presented listing the presence of the viii antrhraquinones in families, genuses and species of plants, fungus and lichens. (compiled from the Chemical Abstracts during 1973-1983). From the wood of Ocotea cymbarum, a tree of the Lauraceae Family, six compounds have been isolated, β-sitosterol (Oc-5, 38), three allylbenzenes 3-(2,5-dimethoxy-3,4- methylenedioxiphenyl)-1-propene (apiole, Oc-1, 21) , 3- (2,3- dimethoxy-4,5-methylenedioxiphenyl)-1-propene (dilapiole, Oc-2, 22) and 3-(2,3,5-trimethoxy-4-hidroxyphenyl)-1-propene (Oc-3, 23), one propanediolphenyl: 3-(2,5-dimethoxy-3,4- methylenedioxyphenyl)-2,3-propanediol (apioleglicol, Oc-6, 41) and one lignane: 4,4',9,9'-tetrahidroxy-3,3',5,5'- tetramethoxy-7,6',8,8'-lignane (lyoniresinol, Oc-4 37) In the same way the structures of the isolated compounds have been determinated through Ultraviolet, Infrared, Nuclear Magnetic Ressonance (1H and 13C) and Mass spectrals data. To confirm the structural determinaions acetoxy (Oc-3, 0c-4, and Oc-6) and methoxy (Oc-4) derivates were prepared. The compound Oc-6 was been sintetized strarting the reacton of a mixture of Oc-1 and Oc-2 with OsO 4. From the ten isolated compounds, five (Hf-3, Hf-4, Hf-5, Oc-3 and Oc-6) were previusly unknown as natural products in the literature.