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4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids — Their Synthesis and Determination in Berry Fruit and Vegetable

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4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids — Their Synthesis and Determination in Berry Fruit and Vegetable 4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids — Their Synthesis and Determination in Berry Fruit and Vegetable Bernhard Schuster, Michael Winter, and Karl Herrmann* Institut für Lebensmittelchemie der Universität Hannover, Wunstorfer Straße 14, D-3000 Hannover 91 Z. Naturforsch. 41c, 511—520 (1986); received October 22, 1985/January 10, 1986 4-O-ß-D-Glucosides of Hydroxybenzoic Acids, 4-O-ß-D-Glucosides of Hydroxycinnamic Acids, Synthesis, Quantitative Determination, Berry Fruit, Vegetable Protocatechuic acid-4-, gallic acid-4-, caffeic acid-4-, ferulic acid- and p-coumaric acid-O-ß-D- glucoside were synthesized. These substances were characterized by UV, 'H NMR, 13C NMR and FAB-MS. Their proportions in berry fruit and vegetable were determined by means of HPLC and capillary GC. Introduction Materials and Methods The derivatives of hydroxybenzoic and hy­ Synthesis of protocatechuic- and gallic acid-4-O-ß-D- droxycinnamic acids are widespread in the plant glucoside kingdom. A considerable number of these deriva­ Scheme 1 shows the course of synthesis of both tives are well known [1], Nevertheless there is only glucosides. little existing information about the glucosides of these compounds and their distribution. 3-O-acetyl-protocatechuic acid Syringic acid-O-ß-D-glucoside was detected in By the method of Lesser and Gad [13] the 3-O- Anodendron affine. [2], as well as /»-hydroxybenzoic acetyl-protocatechuic acid was prepared for use as a acid-O-ß-D-glucoside in a great number of Apiaceae protected start material. [3]. Protocatechuic acid-4-O-ß-D-glucoside was Protocatechuic acid (4.5 g) was dissolved in 2 n found in cockroaches of Periplaneta americana and NaOH (15 ml). After cooling with ice, 2 n NaOH Blatta orientalis [4], (15 ml) and acetic acid anhydride (3 g) were added The glucosides of hydroxycinnamic acids also simultaneously while stirring the solution. After one could be detected in plants. The O-ß-D-glucosides of hour and acidifying with HC1 the resulting 3-O- p-coumaric and ferulic acid were found in the need­ acetyl-protocatechuic acid was filtered off. This les of Conifers besides the glucosides of /?-hydroxy- crude product was used for the following reactions. benzoic, protocatechuic and vanillic acid [5—8]. But these compounds were not completely characterized. Acetylated l-0-protocatechoyl-(4-0-ß-D-glucosyl)- Furthermore the glucosides of caffeic, p-coumaric ß-D-glucose and ferulic acid were detected in tobacco [9] and in tomatoes [10—12]. The received derivative was coupled with a-aceto- To acquine further information about the distribu­ bromoglucose (2,3,4,6-tetra-O-acetyl-D-glucosyl-a- tion of the 4-O-ß-D-glucosides of the hydroxybenzoic bromide) to an acetylated l-0-protocatechoyl-(4-0- and hydroxycinnamic acids we synthesized these ß-D-glucosyl)-ß-D-glucose in presence of quinoline compounds. The substances were characterized by and silver oxide [14]. 3-O-acetyl-protocatechuic acid (3 g) was dissolved UV, ‘H NMR, I3C NMR and FAB-MS. This process was necessary to obtain pure and authentic reference in quinoline (7 ml). This solution was treated with substances for HPLC and GC. Additionally the a-acetobromoglucose (5 g) and silver oxide (1.4 g). While stirring intensively the reactants became paper reports on the quantitative determination of warm. Afterwards the mixture was allowed to stand these glucosides in fruit and vegetable. for 2—3 hours in a vacuum desiccator. Subsequently it was extracted with acetic acid (10 ml). Then the * Reprint requests to Prof. K. Herrmann. filtered extract was poured into iced water (100 ml). Verlag der Zeitschrift für Naturforschung, D-7400 Tübingen The resulting product being insoluble and crude was 0341 - 0382/86/0500 - 0511 $ 0 1 .3 0 /0 purified by repeated recrystallization from methanol. Bereitgestellt von | Technische Informationsbibliothek Hannover Angemeldet Heruntergeladen am | 23.11.17 13:40 512 B. Schuster et al. ■ 4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids COOH ture was neutralized with sulphuric acid. Afterwards the precipitated barium sulphate was filtered off. Using preparative HPLC the crude product was purified. OH 3,5-Diacetyl-gallic acid 0H~ This compound was synthesized using the method Acetic anhydride of Lesser and Gad [13]. Gallic acid (5 g) was dissolved in 2 n NaOH COOH (15 ml) and cooled with ice. While stirring 2 n NaOH (30 ml) and acetic acid anhydride (6 g) were added simultaneously. After one hour the mixture was acidified with HC1. The precipitating 3,5- OH diacetyl-gallic acid was filtered off. A g2 0 Gallic acid-4-O-ß-D-glucoside Qui no line This glucoside was prepared as described above Acetobromogiucose for protocatechuic acid-4-O-ß-D-glucoside. Synthesis of caffeic acid-4- and p-coumaric acid-O-ß-D-glucoside Forming the glucosides of the corresponding hy- droxybenzaldehydes (p-hydroxybenzaldehyde and protocatechualdehyde) using a-acetobromoglucose, the resulting glucosides were obtained by deacetyla- tion and a final Knoevenagel-reaction [16—18]. Ba(0H)2 The process of synthesis will be described using /?-coumaric acid-O-ß-D-glucoside as an example (Scheme 2). Acetylated 4-O-ß-D-glucosyl-benzaldehyde p-Hydroxybenzaldehyde (6.1 g) and a-aceto­ bromoglucose (8.0 g) were dissolved in acetone (40 ml). After addition of 7% NaOH (10 ml) the COOH solution was stirred intensively and was allowed to Scheme 1. Synthesis of protocatechuic acid- and gallic acid- react for 24 h. After this time the solution was 4-O-ß-D-glucoside. R' — H, protocatechuic acid; R' = OH, gallic acid; R" = H, 3-acetylprotocatechuic acid; R" = poured into iced water and stirred for 60 min. In the OAc, 3,5-diacetylgallic acid. mean-time crystallization started slowly. The crys- talls were filtered off and became recrystallized from Protocatechuic acid-4-O-ß-D-glucoside 50% methanol. Protocatechuic acid-4-O-ß-D-glucoside was pre­ pared by alkaline hydrolysis [15]. 4-O-ß-D-glucosyl-benzaldehyde The acetylated l-0-protocatechoyl-(4-0-ß-D- After the desolving of the acetylated product, glucosyl)-ß-D-glucose (1.5 g) was dissolved in using methanol ( 2 0 ml) as solvent, 0 . 1 n methanolic methanol (10—15 ml) during warming. Using nitro­ sodium methylate (0.5 ml) as reactant was added. gen atmosphere a saturated solution of barium hy­ This mixture was allowed to saponify for 20 min in a droxide (10 ml) was added. water bath at 80 °C under reflux. The still warm solu­ This solution was kept in a boiling water bath for tion was treated with petroleum ether until it became 5 min. After cooling to room temperature the mix­ turbid. Colourless crystalls precipitated slowly. Bereitgestellt von | Technische Informationsbibliothek Hannover Angemeldet Heruntergeladen am | 23.11.17 13:40 B. Schuster et al. ■ 4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids 513 Ac0^CH2 A c O - ^ ^ 0 h ° —( c ^ - cho AcO I Br R oC-Acetobro moglucose Hydroxybenzaldehyde NaOH; CH3COCH3 Malic acid acetylated Ferulic acid-O-ß-D-glucoside ' Pyridine Piperidine CH30-Na+. CHCl3 HO—CHi HO 0-(C)\-CH=CH-COOH H H3C0 Ferulic acid-O-ß-D-glucoside p-Coumaric acid-O-ß-D-glucoside Caffeie acid-4-0-ß-D-gtucoside Scheme 2. Synthesis of p-coumaric acid-, caffeic acid- and ferulic acid-O-ß-D-glucoside. R = H, p-hydroxybenzaldehyde resp. p-coumaric acid; R = OH, protocatechualdehyde resp. caffeic acid; R — OCH3, vanillin. which were recrystallized twice from methanol for pyridine (2 ml). Piperidine (0.03 ml) was added as a purification. catalytic agent. This mixture was heated up to 78—80 °C for 12-14 h. The start of the reaction can p-Coumaric acid-O-ß-D-glucoside be observed by nascent bubbles of carbondioxide. Malonic acid (0.6 g) and the O-ß-D-glucoside of The solution was poured into ether, which contained p-hydroxybenzaldehyde (0.5 g) were dissolved in 5% acetic acid. With stirring precipitation started. Bereitgestellt von | Technische Informationsbibliothek Hannover Angemeldet Heruntergeladen am | 23.11.17 13:40 514 B. Schuster et al. ■ 4-O-ß-D-Glucosides of Hydroxybenzoic and Hydroxycinnamic Acids The ether was decanted and the rest of it was blown The solution was brought to dryness using a rotation off. The residue was dissolved in ethanol and precipi­ evaporator. The dry residue was washed out with tated again with ether. After the ether has been ethanol repeatedly. The ethanolic extracts were drained off the glucoside was recrystallized from dried out again. Recrystallization from water and water. finally from ethanol followed. Caffeic acid-4-O-ß-D-glucoside Chemical identification This glucoside was prepared as described above Alkaline hydrolysis: The glucoside (1—2 mg), dis­ for p-coumaric acid-O-ß-D-glucoside. solved in 2 n NaOH (2 ml) was allowed to react for four hours at room temperature under nitrogen Synthesis of ferulic acid-O-ß-D-glucoside atmosphere. After neutralization with 2 n HC1 this Vanillin as start material was treated with a-aceto- solution can be used directly for HPLC and for GC bromoglucose by the method of Reichel and Schickle after derivatisation (see enzymatical hydrolysis). [19]. The resulting acetylated glucoside of vanillin Acidic hydrolysis: The glucoside (1—2 mg), dis­ was caused to react with malonic acid to acetylated solved in 2 n HC1 (2 ml), was heated under reflux up ferulic acid-O-ß-D-glucoside by the method of Hann to 90 °C in a water bath for 90 min. After neutraliza­ [20]. Subsequently to the Knoevenagel-reaction the tion with 2 n NaOH the solution was analysed by product was saponified (Scheme 2). HPLC. Enzymatical hydrolysis: The glucoside (1—2 mg) was added to a solution of 1 mg ß-glucosidase in Acetylated vanillin-O-ß-D-glucoside bidistilled water (1 mg).
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