Neochlorogenic acid

Fig. 2.48. Separation of an extract by HPLC under optimized conditions in a 250 mm X 2 mm i.d., 5 pm particle, C18 column. The mobile phase was a gradient prepared from 0.03 per cent TFA in water (a) and acetonitrile (b) mobile phase composition (%) was changed from 90a 10b to 64a 36b in 35 min. The flow rate was 0.2 ml/min, the temperature 25°C, and detection was performed at 210 and 330 nm. Peak assignments 1 = pseudochlorogenic acid 2 = neochlorogenic acid 3 = chlorogenic acid 4 = cryptochlorogenic acid 5 = cynarin 6 = cynaroside 7 = scolymoside 8 = 3,4-di-O-caffe- oylquinic acid 9 = 1,3-di-O-caffeoylquinic acid 10 = 4,5-di-O-caffeoylquinic acid 11 = cynaropikrin. Reprinted with permission from M. Hausler et al. [148].

Mate contains both caffeine (0.4-2.4%) and theobromine (0.3-0.5%). Also found are triterpene saponins and the caffeic acid derivatives—chlorogenic acid, neochlorogenic acid, and cryptochlorogenic acid. Flavonoids in mate are rutin, isoquercetin, and kaemferol glycosides. A nitrile glycoside, menisdaurin, is also present, which is noncyanogenic. 

Elaeagnus pungens Thunb. E. umbellata Thunb. Hu Tin Chi (root, leaf, fruit) Harman, tetrahydroharman, dihydroharman, 2-methyl-l,2,3, 4-tetrahydro-P-carboline, caffeic acid, chlorogenic acid, catechin, neochlorogenic acid, epicatechin.48 Treat coughs, watery diarrhea, an astringent in hemoptysis. 

Fig. 9 HPLC chromatogram of pitted prune extract. 1996, Society of Chemical Industry. Reproduced with permission. A. HMF B. neochlorogenic acid C. cinnamic D. 3 -p-coumaroylquinic E. chlorogenic F. caffeic G. cinnamate H. coumaric I. flavonol J. rutin K. sorbic acid.

Coffee brewed from roasted beans and those prepared from instant powder, including the caffeine-free type, all display mutagenic activity. Apart from natural mutagens such as caffeic acid and its precursors chlorogenic and neochlorogenic acids, these drinks contain mutagenic products of pyrolysis methylglyoxal and less active gly-oxal and diacetyl (Ames, 1986) ... 

Cinnamic acid, 3,4-dihydroxy-, 5-ester with 1,3,4,5-tetrahydroxycyclohexane-carboxylic acid neochlorogenic acid 51. Phenol, 4-methyl- /7-cresol... 

The phenolic compound content of the Cucurbitaceae is very low. Only trace amounts (3mg/ kg f w.) of neochlorogenic acid (3 -caffeoylquinic acid) were detected in one out of three zucchini (summer-squash) cultivars [40]. In an extensive study on the phenolic content of melons, watermelon, etc., only traces (ferulic acid were detected after hydrolysis. Very small antioxidant activity was reported for cucumber extracts [61], consistent with the very small phenolic compound content. However, the phenolic metabolism of melons is activated under environmental stress and wounding induces the phenylalanine ammonia lyase (PAL) gene [62]. 

An HPLC study of the individual phenolic acid derivatives showed chlorogenic acid to be the predominant compound in potato (22-71 mg/kg). Cryptochlorogenic acid (11 mg/kg), neochlorogenic acid (7 mg/kg) and isochlorogenic acid (4,5-dicaffeoyl quinic acid) (Fig. 4) (3 mg/kg) were also present in smaller amounts [80]. It was also demonstrated that caffeic acid compounds are not distributed uniformly in the tuber, but occur in strongly decreasing concentrations from the outer to the inner section. About 50% of the compounds as a whole are located in the potato peel and adjoining tissue. 

Caffeoylquinic acid (chlorogenic add) 4-0-Caffeoylquinic acid (cryptochlorogenic acid) 3-0-Caffeoylquinic acid (neochlorogenic acid) Isorhamnetin rutinoside Isorhamnetin glucoside Kaempferol rutinoside Kaempferol glucoside... 

FIGURE 8.3 Chemical structures of chlorogenic, cryptochlorogenic, and neochlorogenic acids. 

Phenolic acids Hydroxycinnamic acids Caffeic acid Chlorogenic acid Ferulic acid Sinapic acid Caftaric acids Neochlorogenic acid p-Coumaric acid Blackberry, raspberry, strawberry, blackcurrant, blueberry, cranberry, pear, sweet cherry, apple, orange, grapefruit, lemon, and peach [8]... 

The free hydroxyl cinnamic acids in raw cocoa seeds were p-coumaric acid [41, 42], caffeic acid [43, 44], femlic acid [41], chlorogenic acid, and neochlorogenic acid [43, 45] in raw cocoa extracts. The existence of chlorogenic acid was also stated by Wollgast [46]. Aesculetin was found 1965 [41]. 

In case of I. batatas, the biosynthesis of chlorogenic acid proceeds via 1-0-caffeoyl-P-glucose in contrast to different solanaceous species e.g., Nicotiana taba-cum, which used caffeoyl-CoA for that purpose (Strack et al. 1987 and references therein). Furthermore, it was shown that chlorogenic acid acted as the acyl donor in the biosynthesis of isochlorogenic acid in the roots of this species (Kojima and Kondo 1985) which was also shown to produce neochlorogenic acid. 

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