FLAVONOIDS OF AERIAL PARTS OF SPREADING MARIGOLD (TAGETES PATULA L.)

Abstract

The arial parts of the spreading marigold (Tagetes patula L.) of the Asteraceae family is a promising source of biologically active compounds, including flavonoids. It is known, that the content of total flavonoids in the flowers of this plant reaches 9% (calculated on patulitrin), and in the aboveground part (leaves and stems) – about 3.0% (calculated on rutin), however, data on the component composition of flavonoids are contradictory.
 The aim of the study is to study the flavonoid component composition of the arial p part of the rejected marigolds.
 As a result of studies using column chromatography on silica gel L 40/100, 6-methoxykaempferol (2), 7-O-glucoside of methoxykaempferol (3), quercetin (6), patuletin (7) and patulitrin (7-O-β-D-glucopyranoside of patuletin) (12) were isolated for the first time from the flowers of Tagetes patula L. (Mandarin variety), and from the arial parts (leaves and stems) of this species - kaempferitrin (3-O-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside of kaempferol) (4), 3-O-β-D-xylopyranoside-7-O-α-L-rhamnopyranoside of kaempferol (5), quercetin (6), patuletin (7), 3-O-β-D-xylopyranoside-7-O-α-L-rhamnopyranoside of quercetin (8), 7-O-α-L-rhamnopyranoside of quercetin (9), quercitrin (10), isoquercitrin (11). Interestingly, that the common components of the herbs (leaves and stems) and flowers are only two flavonoids – quercetin (6) and patuletin (7). As for patulitrin (7-O-β-D-glucopyranoside of 3,5,7,3’,4’-pentahydroxy-6-methoxyflavone, or patuletin) (12), which is the dominant flavonoid of the flowers of this plant, this component is not found in the herbs of this plant. It was determined, that glycosides of kaempferol (1) and quercetin (6) predominate in the herb of the Tagetes patula L. with the dominant flavonoid being 3,7-O-dirhamnoside of kaempferol (4).
 The identification of the isolated flavonoids was carried out using UV, 1H-NMR, 13C-NMR spectroscopy and mass spectrometry, as well as the results of acid and enzymatic hydrolysis.
 3-O-β-D-xylopyranoside-7-O-α-L-rhamnopyranoside of kaempferol (5) and 3-O-β-D-xylopyranoside-7-O-α-L-rhamnopyranoside of quercetin (8), isolated from the herb of the Tagetes patula L., are new natural compounds.