Cinnamic acid glycosides

The chemical formulae for a variety of plant phenols are given in Fig. 16.2, including examples of simpler phenols, such as cinnamic acid derivative, and of tocopherols, flavonoids, flavonoid glycosides and anthocyanidins. The flavonoids include the following subclasses flavanones (taxifolin), flavones (luteolin), flavonols (quercetin) and flavanols (catechin/epicatechin). The... 

The jalapin-like chloroform-soluble material from the dried tubers of I. batatas was subjected to successive column chromatography over silica gel and HPLC to yield batatosides J-L (55-57) with the oligosaccharide core based on operculinic acid E. The lactonization site was placed at C-2 of the first rhamnose unit. Cinnamic acid was present as the esterifying residue at the C-2 position of the third rhamnose unit. These resin glycosides also contain esterifying residues composed of n-dodecanoic or (25)-methylbutyric acids at the C-2 or C-3 positions on the second rhamnose unit of the oligosaccharide core as well as n-decanoic or n-dodecanoic acids at C-4 on the third rhamnose (40). 

The route for the cytotoxic ipomoeassin resin glycosides relied on the use of compound 256 as a new cinnamic acid surrogate with its trisubstituted double bond and meets the requirement of being hydrogenation resistant in the presence... 

Lycium chinense Miller Di Gu Pi (Matrimony vine) (root bark) Cinnamic acid, betaine, peptides, acyclic diterpene glycosides, polysaccharide, kukoamines.33 Lower blood sugar and blood pressure, antipyretic, stimulate uterine contraction, antibacterial. 

Cinnamic acids may condense with molecules other than quinic acid, including rosmarinic, malic and tartaric acid, aromatic amino acids, choline, mono- and polysaccharides, glycerol, myo-inositol, and different glycosides (anthocyanins, flavonols and diterpenes) [13]. 

Most phenolic glycosides are water soluble, but the corresponding aglycones are usually less so. Phenolic substances are aromatic and therefore show intense absorption in the UV region of the spectrum (2). Most of the benzoic acid derivatives displayed their maxima at 246-262 nm, with a shoulder at 290 - 315 nm, except gallic and syringic acid, which have absorption maxima at 271 and 275 nm, respectively (4). The cinnamic acids absorb in two regions in the ultraviolet, one... 

For phenolics in fruit purees and jams (54), an HPLC condition similar to that used for apple juice, but with acidified water (5% formic acid) and methanol, was utilized as a solvent system. In most cases, detection was achieved with diode array detection, at UV 280 nm and 320 nm. The different phenolic compounds were identified by their UV spectra and by chromatographic comparisons with authentic standards. Several classes of phenolic compounds (cinnamic acids, catechins, dihydrochalcones, and flavonol glycosides) could be detected along with arbutin in... 

For the red wines (82-84), which were injected directly into the HPLC without sample preparation, a ternary-gradient system using aqueous acetic acid (1% and 5% or 6%), and acidified acetonitrile (acetonitrile-acetic acid-water, 30 5 6) was used for cinnamic acid derivatives, catechins, flavonols, flavonol glycosides, and proanthocyanidins. Due to the large number of peaks, the gradient was extended to 150 min for the resolution of many peaks of important phenolics. This direct injection method was able to separate phenolic acids and esters, catechins, proanthocyanidins, flavonols, flavonol glycosides, and other compounds (such as tyrosol, and rrans-resveratrol) in wine in a single analysis. However, use of acetic acid did not permit the detector (PDA) to be used to record the UV spectra of phenolics below 240 nm (84). 

PP Mouly, EM Gaydou, R Faure, JM Estienne. Blood orange juice authentication using cinnamic acid derivatives. Variety differentiations associated with flavanone glycoside content. J Agric Food... 

Several cinnamic acids 53 are found in grapes and wine, but they are invariably esterified (e.g., with tartaric acid) or as simple glycosides 54 (65BSF2649,98JAFC4203,00JAFC2681,09MI515,07MI101) ... 

Flavone glycosides often occur as acylated derivatives either with aliphatic or aromatic acids. Hydroxy-cinnamic acid derivatives are the most frequent in nature and MS fragmentations of these types of compounds show ions produced by the loss of 146,162,176, or 206 m.u., corresponding to the losses of the acyl residues />-coumaroyl, caffeoyl, femloyl, or sinapoyl, respectively. Brassicaceae species are rich in flavonoid glycosides acylated with hydroxyl-cinnamic derivatives, and most of them... 

The simple coumarin nucleus (Fig 7.3), which is derived by lactone formation of an ortho-hydroxy-czs cinnamic acid, is a common metabolite in higher plants and is often found in glycosidic form. Coumarins are common in Api-aceae, in certain genera of Fabaceae (e.g. Dipteryx odorata, Melilotus officinalis), Poaceae (e.g. Anthoxanthum odoratum) and Rubiaceae (e.g. Galium odoratum). However, proliferation of coumarins to the status of major chemical markers occurs in only a few cases, most notably, but not exclusively, in the Api-aceae (subfamily Apioideae) and in the Rutaceae (Gray and Waterman, 1978 Murray et al., 1982). In these cases, the coumarin nucleus has almost invariably been embellished by the addition of a prenyl unit leading to furocoumarin (Fig 7.3) and pyranocoumarin structures. 

Glycosides of this vitamin (sometimes denoted as vitamin B3) were not described, however, there exists an evidence that bound niacin from wheat bran (termed niac)4in) has a single nicotinic acid moiety at least partially linked to an aromatic amine with glucose, xylose, and arabinose in a 6 3 1 molar ratio per molecule, with approximately three cinnamic acid esters [152,177,178]. It seems that these glycosidic complexes limit the bioavailability of the nicotinamide and for its liberation they must be treated, e. g., by soaking com in a lime solution, traditionally performed in Central America during production of tortillas [179]. 

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