ies related to flavonoids or other pigments are scarce (e.g. De Simone et al., (3); Crawford and Evans, (2)). Chenopodium hircinum and C. album are widely ...
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63 (112):279-281; XII - 1998
47th ANNTVERSARY
Leaf flavonoids in Chenopodium hircinum Schrad. and Chenopodium album L. (Chenopodiaceae)
Abstract. Four flavonoids from the leaves of two species of Chenopodium have been isolated. Three of them a r e common to C. hircinum and C. album and one of them was identified a s quercetin-3ramnoglucoside. The other two were not identified but their spectral characteristic are given. A fourth flavonoid, present only in the leaves of C. hircinum, was identified as kaempferol-3-galactoside.
Key words: Chenopodiaceae - flavonoids - quercetin - kaempferol - chemosystematics - alternative crops - medicinal plants
Members of the family Chenopodiaceae are considered new cultivated crops of polyvalent use (l),potential alternative world crops. This family provides edible roots (e.g. Beta vulgaris L.), leaf vegetables (e.g. Spinacia oleracea L.), oils (e.g. Chenopodium ambrosioides L.) and grain (e.g. Chenopodium quinoa Willd.). Chemical studies of Chenopodiaceae are very extensive especially those related to grain analysis or food production (e.g. C. quinoa), but studies related to flavonoids or other pigments are scarce (e.g. De Simone et al., (3); Crawford and Evans, (2)). Chenopodium hircinum and C. album are widely distributed in the world, and particularly in Argentina, where they have spread as weeds in many farming systems. These species were declared "plague" because of their invasion of cultivated fields of wheat, sorSupported by Fundación Miguel Lillo - Area Botánica Fundación Miguel Lillo - Area Botánica - Miguel Lillo 251 - 4000 Tucumán (Argentina) Facultad de Ciencias Naturales e I.M.L. - Universidad Nacional de Tucumán - Miguel Lillo 205 4000 Tucumán (Argentina). The authors are grateful to Dr. P. Seeligman who provided valuable information and comments of a n earlier version of the manuscript and also this one
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ghum, sunflower, potatoes, rice, flax, maize, alfalfa and tobacco, and even in mastic, orange and groves. These species have not been exploited for profit in large scale, but their use as fodder (young plants) and in popular medicine (diurectic) has been reported (8). The purpose of our research is the identification of the flavonoids synthesized by Ch. hircinum and Ch. album in order to get markers useful for the systematics of to get information on molecular markers useful for the systematics of the Chenopodiaceae, a family on which chemosystematic studies have been very scarce so far. From the morphological point of view these two species are easily confused because their leaves are very similar in shape. Thus, this contribution may provide a good tool for correct systematic identifications. MATERIAL & METHODS
Plant material. Leaves of Chenopodium hircinum Schrad. and Chenopodium album L. were collected during December on the banks of Lules river (Tucumán, Argentina), elevation 450 m above sea level. The leaves were put immediatly into paper bags and dried at 35-45°C. The dried material was ground and standard methods of flavonoid analysis were used (5, 7). Extraction of flavonoids. Flavonoids were extracted from 1 g of dried leaves which were macerated twice with the following solvents: MeOH (80% methanol) and MeOH 50% (methanol 50%) solvents: 80% methanol (MeOH) and 50% MeOH during 48 h. Both extracts were combined and concentrated under reduced pressure. The residue was dissolved in 1m1 of 80% MeOH and this solution was analyzed. Separation of flavonoids was carried out by two-dimensional paper chromatography on 3 M Whatman paper sheets (30 x 30 cm). The purification, separation, hydrolysis and identification of flavonoids was described by Israilev & Seeligmann (4). Spectrophotometric analysis was performed with a Metrolab Wvisible, model 2600 instrument. The acid hydrolisis (HCI 2N) of compounds 1 and 2 gave two aglycones identified by direct comparison (by TLC and by W spectra) as quercetin and kaempherol. RESULTS & DISCUSSION
Four flavonoids were isolated from the leaves of two species of Chenopodium. Three of them are common to Ch. hircinum and C. album. One of them (compound 2) was identified as quercetin 3-rhamnoglucoside. The other, present only in the leaves of Ch. hircinum (compound), was identified as kaempferol-3-galactoside which agrees with the findings in Ch. quinoa seeds [De Simone et al. (3)l. Two other compounds (3 and 4) were not identified but we
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Table 1.- Spectral characteristics of the flavonoids detected in Chenopodium hircinum and Chenopodium album leaves
MeOH: methanol; MeOK potasium rnetóxide; AIC13: Alurniniurn trichloride; AIC13 IHCI: Alurninium trichloridelclorhidric acid; NaOAc: sodiurn acetate; NgcOlH3B03 : Sodium acetate Iboric acid; sh: shoulder
provide their spectral characteristics (Table 1). On the chromatogram, compound 2 yields a dark spot under UV light and a yellow-green spot with W and NH,. The reaction with NA (Naturstoffreagenz A: 2-amino-etyl-diphenyl-borate)(7, 6) yields an orange colore substance indicating a compound with two hydroxyls in B ring. Compound 1, in Ch. hircinum, is very similar to compound 2 but the reaction with NA gives a yellow color which characterises compounds with one hydroxyl in B ring. The results show that leaf flavonoids are a good tool to separate Ch. hircinum from Ch. album because of their different flavonoid maps. The affinity between the two species is through one compound: quercetin-3-rhamnoglucoside. The presence of kaemphero-3-galactoside (compound 1) only in C. hircinum relates this species to C. quinoa according to the findings of De Simone et. al. (3). Detailed chemosystematic studies of other species are needed to proviede new insights into the phylogenetic relationships among the Chenopodiaceae. REFERENCES
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1. Carlsson R, In: Acta Universitatis Upsaliensis Symbolae Botanicae Upsaliensis XXVIII: 3.Proceedings of the 1987Naturforsch Kultursymposium held in Stockholm and Uppsala. Set. 14.17 (1988) 2. Crawford DJ, Evans KA, Brittonia 30 (1978)313 3. De Simone F, A Dini, C Piazza, P Saturnino, O Schettino, Phytochernistry 29 (1990)3690 4. Israilev LA de, P Seeligman, Lilloa 36 (1983)5 5. Mabry TJ, KR Markham, MB Thomas, The systematic identification of flavonoids. Springer Verlag (1970)p 354 6. Mc Cormick SP, Flavonoid chemistry of Pussiflora subgenus Plectostemma. PhD Thesis, The University of Texas at Austin. Texas (1982) 7. Markham KR,The Techniques of flavonoid identification. Academic Press London, (1982)p 113 8. Marzocca A, Manual de malezas. 3'" Edición. Editorial Hemisferio Sur, Buenos Aires (1976)p 241
