Non-flavonoids

Fukuda, K.,Ohra, T. 8cYamazoe,Y. (1997). Grapefruit component interacting with rat andhuman P450 CYP3A possible involvement on non-flavonoid components in drug interaction. Biol. Pharm. Bull, 20, 560-4. 

There are two groups of non-flavonoid polyphenols having lower molecular weights, which are themselves not heterocyclic compounds, but nevertheless are precursors to oxygen heterocycles ... 

These non-flavonoid phenolic compounds are easily oxidized (89JC428, 89JAFC1069) and show anticancer activities (04MI3707). 

Upon analysis of the non-flavonoid fraction of wine, pyrimidines have been found (65MI307, 79AJEV98) by chromatography on Sep-hadex 6-25 and phenol assayed by colorimetry. Of the nucleic acids (mainly guanine 96 and xanthine 97) less than 5mg/L can be assumed to be present. 

Fukuda K, Ohta T, Yamazoe Y. Grapefruit component interacting with rat and human P450 CYP3A possible involvement of non-flavonoid components in dmg interaction. Biol Pharm Bull 1997 20 560 564. 

Grape phenolics compounds are important to wine colour, flavour, astringency and bitterness, with red wines generally containing 1200-1800 mg gallic acid equiv-alents/L of total phenolics, six- to ninefold more than present in white wines (Kennedy et al. 2006). Hydroxycinnamic acids (non-flavonoid phenolics) are major phenolic compounds of white wines and are responsible for their colour. Other non-flavonoid phenolics contribute flavour, such as vanillin, vinyl phenols and gallic acid. Vinyl and ethyl phenols, which can be present to variable extents, elicit phenolics, medical, Bandaid , barnyard and spicy characters in wine, which are generally... 

The non-flavonoid phenolic constituents in wine are divided into hydroxybenzoic acids and hydroxycinnamic acids, volatile phenols, stilbenes and miscellaneous compounds (e.g. lignans and coumarins). Although non-colored, the non-flavonoid constituents are known to enhance and stabilize the color of red wines by intra- and intermolecular reactions. They furthermore contribute to wine flavor (volatile phenolic acids) and some of them (e.g. resveratrol) exhibit potent biological activities. 

Trans-resveratrol (trans-3,5,4 -trihydroxystilbene) is a non-flavonoid polyphenol found in grapes, mulberries, and other food prod-ucts. It is responsible for the antioxidant activity of red wine. Intake of moderate amount of red wine has been found to reduce the risk of cardiovascular diseases. In addition to antioxidant activity, resveratrol could inhibit platelet aggregation, and showed anticancer activity. The phenoxyl radicals of resveratrol produced during oxidation by hydroxyl radicals, one-electron oxidants, and peroxyl radicals showed absorption maximum at 410 nm (Fig. I). Reports indicate that trans-resveratrol is a better radical scavenger than vitamins E and C and its activity is similar to that of the flavonoids epicatechin and quercetin. From the comparison of the spectral and kinetic properties of the transients derived from trans-resveratrol and its analogues, it could be concluded that in the neutral and acidic solutions, the para-hydroxy... 

Yamanaka, N. Oda, O. Nagao, S. Prooxidant activity of caffeic acid, dietary non-flavonoid phenolic acid, on Cu -induced low density lipoprotein oxidation. FEBS Lett. 1997, 405, 186-190. 

Table 2. Non-flavonoidal Chromone Alkaloids from Natural Sources...

Apart from the flavone cochliophilin A methyl ether (10), it has been found that other, non-flavonoid, natural products (e.g. the anthraquinone, emodin) also exhibit potent antidote activity. Whilst the significance of these plant-produced chemicals, in reducing the efficiency of several widely used benomyl-type fungicides, has still to be evaluated, the fact that flavones occur widely in the Plant Kingdom may suggest that crop plants should be routinely screened for potential flavone (and non-flavone)... 

Cinnamate esters arc the only non-flavonoid (word used in a very general sense) and non-alkaloidal, bioactive, identifiable secondary metabolites reported in the genus. Cinnamate esters have been reported in several Erythrina species [24,48.56,90,107-108]. Several cinnamate esters have been reported in the genus and these include erythrinasinate (octacosanyl E isoferulate), erythrinasinate B (octacosanyl E ferulate), erythrinasinate C (tetradecanyl E ferulate), erythrinasinate D (hexacosanyl E isoferulate), hexacosanyl E... 

Chlorogenic acid (43-108 mg/kg fw. as caffeic acid) [19] and arbutin (1-gucosyl-1,4-dihydroxy-benzene) are the main non-flavonoid phenolics. Catechin and, especially, epicatechin (7-12 mg/kg) have also been found in pears [19]. In the peels, a complex flavonoid pattern of quercetin and isorhamnetin 3-glycosides has been detected. The occurrence of characteristic flavonols acylated with dicarboxylic acids in pears has recently been reported [28]. 

Antioxidants are used to presmve food and other tuomaterials by retarding randdity, discoloration or deterioration due to autoxidation [3]. Chlorogaiic add (CHG) and caffeic acid (CA) ate two of die most interesting non-flavonoid catecholic compounds, vdiich are present in many plants and possess anti-inflammatory, antimuta nic, and anticarcinogenic properties [4]. 

Resveratrol (3,5,4 -trihydroxystilbene C14H12O3, molecular weight 228.25 g/mol) is a non-flavonoid polyphenolic compound abundant in grapes, peanuts, and other foods that are commonly consumed as part of the human diet [29]. The compound was first isolated from the root of Polygonum cuspidatum, a plant used in traditional Chinese and Japanese medicine [30]. Resveratrol (Fig. Ic) exists as two structural isomers cis- Z) and trans- E). The traws-isomer is biologically more active than the cis-isomer, probably due to its non-planar conformation [31, 32]. Despite its poor water solubility, resveratrol exhibits high membrane permeability and can be... 

Some researchers have reported that there is no increase of non-flavonoid phenolics with increasing skin contact time (Sims and Bates, 1994), while others have reported the opposite (Kovac et al., 1992). In this research. Cabernet Sauvignon showed no significantly increases in caftaric acid concentration with increasing skin contact time. However, in the Chambourcin wines, there was a significant decrease of caftaric acid with increasing skin contact time. This could be due to tyrosinase or polyphenoloxidase (PO) activity during maceration (Ricardo da Silva et al., 1993). In Noble, caftaric acid was present in very low levels compared to the other two varieties. 

At present, the percentage contribution of vitamins to the cancer-protective activity of vegetables or fruits is unknown. In this paper, we present results suggesting an involvement of naturally occurring phenolics in the prevention of genotoxicity and carcinogenicity. Since the number of phenolics in various plants is staggering and the discussion of their beneficial or toxic effects is beyond the scope of any short review, we have focused on non-flavonoid simple phenolics (C6), phenolic acids (C6-C1), cinnamic acid and related compounds (C6-C3). 

Table 5. Genotoxicity of Non-Flavonoid Phenolics or Catecholamines in Various In Vitro Test Systems... 

Such contradictory results also plague the experimental studies on rodents. Polyphenolic betel nut fractions induce oral and gastric lesions in rodents (Bhide et al., 1979 Ranadive et al., 1979 Shivapurkar et al., 1980). Various phenolics have cocarcinogenic (Mori and Hirono, 1977 Van Duuren, 1981) or tumour-promoting activities (e.g., Boutwell, 1967 Van Duuren et al., 1973 Hecht et al., 1981 Van Duuren, 1982). However, non-flavonoid phenolics were also found to possess strong anticarcinogenic properties (see preceding section) and lack the capacity of tumour induction (e.g., Hirono et al., 1980). 

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