Natürlich vorkommende Zuckerester von Phenolcarbonsäuren

Birkofer, Leonhard; Kaiser, Christelmargot; Nouvertné, Werner; Thomas, Ursula

doi:10.1515/znb-1961-0406

Cited by 44 publications

(4 citation statements)

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“…Spectra of the two derivatives agreed with those of synthetic glucose esters sf ferulic acid and 9-coumaric acid synthesized according to the procedure of Birkofer et al (4). Addition 0% sodium acetate to the derivatives had no effect on the absorption maxima whereas the addition of a few drops of sodium hydroxide solution caused bathochromie shifts as would be expected from compounds with free phenolic hydroxyl functions.…”

supporting

confidence: 70%

Conjugates of Hydroxycinnamic Acids and Glucose in Some Gymnosperms

Glennie¹,

Bohm²

1966

Can. J. Biochem.

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supporting

confidence: 70%

Conjugates of Hydroxycinnamic Acids and Glucose in Some Gymnosperms

Glennie¹,

Bohm²

1966

Can. J. Biochem.

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“…(c) Glucosylation (16). Acetyl-4-coumaroyl chloride (1.0 g) was allowed to react with 2,3,4,6-tetraacetyl-β-D-glucose (1.21 g) in a solution of chloroform (2.6 mL) and pyridine (0.4 mL) at room temperature for 20 h. Afterward, the reaction mixture was washed with 2 N H 2 SO 4 and 2 N NaHCO 3 and twice further with water.…”

Section: Syntheses Of 4-coumaroyl Glucose and Feruloyl Glucosementioning

confidence: 99%

Biosynthesis of Vanillin via Ferulic Acid in Vanilla planifolia

Negishi¹,

Sugiura²,

Negishi³

2009

J. Agric. Food Chem.

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(14)C-Labeled phenylalanine, 4-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from (14)C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the (14)C labels were also trapped by the unlabeled ferulic acid. However, (14)C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid --> --> ferulic acid --> --> vanillin --> glucovanillin in mature vanilla pods.

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“…In the extract from the anthers with fluorescent pollen, 1-3, 5, and a limited amount of 6-8 were detected, but 9-12 were not (Figure 7B). Compounds 2-4 were isolated from the extract of the anthers with non-fluorescent pollen, while monitoring the blue fluorescence and yellow coloration on TLC; they were identified as 1-O-(E)-feruloyl-β-Dglucose (2; Birkofer et al 1961;Bokern et al 1987) and its (Z)-isomer (3;Hixson et al 2016), and quercetin 3-O-β-D-glucoside (4; Bennini et al 1992;Perkin, 1909), based on its 1 H NMR and LC-MS spectral data. Amounts of 1-12 in the anthers with pollen are summarized in Table 1.…”

Section: Isolation and Identification Of Major Constituents From Anthers And Pollen Grainsmentioning

confidence: 99%

Fluorescence from abnormally sterile pollen of the Japanese apricot

Mori

Shimma

Masuko-Suzuki

et al. 2021

Plant Biotechnology

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We observed trees of the Japanese apricot, Prunus mume 'Nanko' (Rosaceae), bearing two types of flowers: 34% had blue fluorescent pollen under UV irradiation, and 66% had non-fluorescent pollen. The fluorescent pollen grains were abnormally crushed, sterile, and devoid of intine and pollenkitt. The development of microspores within anthers was investigated: in the abnormally developed anthers, tapetal cells were vacuolated at the unicellular microspore stage, and fluorescent pollen was produced. Compounds responsible for the blue fluorescence of pollen were identified as chlorogenic acid and 1-O-feruloyl-β-D-glucose. The anthers with fluorescent pollen contained 6.7-fold higher and 3.8fold lower amounts of chlorogenic acid and N 1 ,N 5 ,N 10 -tri-p-coumaroylspermidine, respectively, compared to those with non-fluorescent pollen. The tapetal vacuolization, highly accumulated chlorogenic acid, and deficiency of N 1 ,N 5 ,N 10 -tri-pcoumaroylspermidine imply that low-temperature stress during the early unicellular microspore stage caused a failure in microsporogenesis. Furthermore, potential effects of the visual difference on the bee behavior were also discussed through the colorimetry. The sterility, likely induced by low-temperature stress, and the preference of honeybees for fluorescence may reduce the pollination efficiency of P. mume.

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Natürlich vorkommende Zuckerester von Phenolcarbonsäuren

Cited by 44 publications

References 0 publications

Conjugates of Hydroxycinnamic Acids and Glucose in Some Gymnosperms

Conjugates of Hydroxycinnamic Acids and Glucose in Some Gymnosperms

Biosynthesis of Vanillin via Ferulic Acid in Vanilla planifolia

Fluorescence from abnormally sterile pollen of the Japanese apricot

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