New Flavone Glucoside Malonylesters from Bryum capillare

Stein, W.; Anhut, Siegbert; Dietmar, H.; Mues, Rüdiger; Barz, Wolfgang; Köster, Johannes

doi:10.1515/znc-1985-7-802

Cited by 19 publications

(7 citation statements)

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“…123 The malonyl equivalent of 131 has been reported previously. 146 The isolation of 3 0 -desmethoxysudachiin C (133) from the peel of the citrus fruit Citrus sudachi (Rutaceae) deserves comment, as this source is a waste product of food processing (the annual fruit production from this species is approximately 8000 tons in Japan). 138 The results of bioassays carried out with the flavone glycosides in Table 1 comprise data on antioxidant (95,97,105,126,134,135,137), immunomodulatory (139,140,142), nerve growth factor potentiating (101,102) and xanthine oxidase inhibition (100, 104) activity.…”

Section: Flavone O-glycosidesmentioning

confidence: 99%

Flavonoids and their glycosides, including anthocyanins

2008

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This review describes more than 600 new examples of naturally occurring flavonoids found either as aglycones or glycosides, comprising flavones, flavonols, chalcones, dihydrochalcones, aurones, flavanones, dihydroflavonols, anthocyanidins and anthocyanins. The main topics addressed are source, identification, biological activity, biosynthesis, synthesis, and ecological or chemosystematic significance, and 514 references are cited.

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Section: Flavone O-glycosidesmentioning

confidence: 99%

Flavonoids and their glycosides, including anthocyanins

2008

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“…This conclusion is consistent with the structures of formononetin 7-O-β-D-glucoside 6′′-O-malonate (40) and biochanin A 7-O-β-D-glucoside 6′′-O-malonate (41), which were established by spectral analysis of the pure compounds from this plant (Beck et al, 1971). Thus, peaks 12A, 14A, 14B, 16, 18A, 22, 23, and 27 (Figure 3) were identified as isoquercitrin 6′′-O-malonate (quercetin 3-malonylglucoside, 45) (Asen, 1984;Gluchoff-Fiasson et al, 1997), pratensein 7-O-β-D-glucoside 6′′-O-malonate [pratensein 7-O-β-(6′′-malonyl)glucoside, 44] (Anhut et al, 1984;Stein et al, 1985), genistin 6′′-O-malonate (6′′-O-malonylgenistin, 39) (Kudou et al, 1991;Park et al, 1995;Stobiecki et al, 1999) 41), and trifoside 6′′-Omalonate (42), respectively. Their structures are shown in Figure 1.…”

Section: Lc-esi-ms Analyses Of the Extract And Its Malonate-free Samp...mentioning

confidence: 99%

LC-ESI-MS Study of the Flavonoid Glycoside Malonates of Red Clover (Trifolium pratense)

Lin

Lindenmaier

et al. 2000

J. Agric. Food Chem.

142

103

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High-performance liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, approximately 20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6' '-O-malonate (39), formononetin 7-O-beta-D-glucoside 6' '-O-malonate (40), biochanin A 7-O-beta-D-glucoside 6' '-O-malonate (41), trifoside 6' '-O-malonate (42), irilone 4'-O-beta-D-glucoside 6' '-O-malonate (43), pratensein 7-O-beta-D-glucoside 6' '-O-malonate (44), isoquercitrin 6' '-O-malonate (45), and 3-methylquercetin 7-O-beta-D-glucoside 6' '-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42-46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.

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“…Field desorption. The first real "soft" spectra of flavonoid glycosides were measured using FD ionization in the positive mode (Schulten and Games, 1974;Beckey and Schulten, 1975;Domon et al, 1982;Stein et al, 1985). Glycosides with up to three sugars, like robinin, have been ionized ( Fig.…”

Section: Flavonoid Glycosidesmentioning

confidence: 99%

Mass spectrometry of underivatized naturally occurring glycosides

Wolfender

Maillard

Marston

et al. 1992

Phytochemical Analysis

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Mass spectrometry is essential for the structure determination of naturally occurring glycosides. Molecular weight and sugar sequence information can be obtained. Development of “soft” ionization techniques has allowed a direct mass spectrometric investigation of underivatized glycosides. Numerous different and complementary methods of ionization have been used for their study. For a given compound, the choice of a particular technique is crucial in order to obtain the structural information needed. A brief survey of these ionization techniques is given, together with examples of their use in major classes of plant glycosides.

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New Flavone Glucoside Malonylesters from Bryum capillare

Cited by 19 publications

References 0 publications

Flavonoids and their glycosides, including anthocyanins

Flavonoids and their glycosides, including anthocyanins

LC-ESI-MS Study of the Flavonoid Glycoside Malonates of Red Clover (Trifolium pratense)

Mass spectrometry of underivatized naturally occurring glycosides

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