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PubMed2003

[Comparative study on content of chlorogenic acid in Lonicera japonica and L. macranthoides].

OBJECTIVE: To exploit and utilize reasonably the abundant natural resources by appraising the medicinal purposes of Lonicera macranthoides Hands-Mazz. through the content of the useful chemical constitutents chlorogenic acid. METHOD: The content of chlorogenic acid in the flowers of L. macranthoides Hands-Mazz in Human and L. japonica Thunb. in Henan and Shandong was compared by HPLC. RESULT: The contents of chlorogenic acid were 4.00% and 4.52% in L. macrathoides from Longhui and Xinning County of Hunan respectively. The contents were 2.20% and 2.46% in L. japonica from Shangdong and Henan respectively. CONCLUSION: The content of chlorogenic acid in L. macranthoides was higher than that in Lonicera japonica.

Chlorogenic Acid↗
PubMed2005

Analyses of arbutin and chlorogenic acid, the major phenolic constituents in Oriental pear.

The HPLC retention time, photodiode array UV spectrum analysis, and LC/MS results indicated that arbutin and chlorogenic acid are the main phenolic constituents in Oriental pear. The two compounds exist in different organs of the Yali pear, which is one of the major cultivars of Pyrus bretschnrideri. The contents of arbutin in the leaf bud, floral bud, flower, and young fruit were 11.9, 12.4, 8.29, and 9.92 mg/g fresh weight (FW), respectively. Chlorogenic acid amounts in the same organs were 2.26, 3.22, 5.32, and 3.72 mg/g FW, respectively. During development, the concentration of the two compounds in Yali pears was the greatest in young fruit (9.92 mg/g FW of arbutin and 3.72 mg/g FW of chlorogenic acid), and then declined swiftly with fruit growth to less than 0.400 and 0.226 mg/g FW, respectively, in mature fruit. Large differences existed in the distribution of the two compounds in parts of the mature fruit of 14 Oriental pear cultivars. The greatest concentration of arbutin was found in the peel (1.20 mg/g FW), which was 3-5 times greater than that found in the core and 10-45 times greater than the level in the pulp. The concentration of chlorogenic acid in the core was greater than that in the peel. The compounds in 17 cultivars of Oriental pear, including P. bretschnrideri, Pyrus pyrifolia, Pyrus ussuriensis, and Pyrus sinkiangensis, were compared with those in 5 cultivars of Occidental pear (Pyrus communis). The mean concentration of arbutin in the Oriental pear cultivars was 0.164 mg/g FW, greater than the 0.083 mg/g FW found in the Occidental pear cultivars. The greatest arbutin content was 0.400 mg/g FW, found in the Yali pear. However, the mean concentration of chlorogenic acid in the Oriental pear was 0.163 mg/g FW, less than that found in the Occidental pear (0.309 mg/g FW).

Arbutin↗
PubMed1986

Inhibitory effect of chlorogenic acid on methylazoxymethanol acetate-induced carcinogenesis in large intestine and liver of hamsters.

The effect of dietary chlorogenic acid on methylazoxymethanol (MAM) acetate-induced carcinogenesis was examined in Syrian golden hamsters. The combined incidence of total large intestinal tumors from male and female hamsters, and the combined incidence of large intestinal adenocarcinomas or the incidence of the carcinomas of male or female animals of the group given a single intravenous injection of MAM acetate (20 mg/kg body wt) and then fed the diet containing 0.025% chlorogenic acid for 24 weeks were significantly lower than those of hamsters given MAM acetate alone. The numbers of hyperplastic liver cell foci in male and female hamsters given MAM acetate and chlorogenic acid were also significantly smaller than those of hamsters given MAM acetate alone. These results indicate an inhibitory effect of chlorogenic acid on MAM acetate-induced carcinogenesis in hamsters.

Animals↗
PubMed2004

[Study on technique of extraction and purifying chlorogenic acid in Eucommia ulmoides Oliver leaves].

Ethanol was used as solvent to extract chlorogenic acid from leaves of Eucommia ulmoides Oliver leaves. The optimum conditions are obtained by response surface analytical method. Optimized conditions for the extraction of chlorogenic acid were obtained: ethanol 51.7%, extraction temperature 55.8 degrees C, ratio of material to liquor 1:12.8, extraction time 2 h. The static adsorption tests are conducted among six kinds of macroporous resins to select NKA-II resin as a optimum resin to adsorb the chlorogenic acid in Eucommia ulmoides Oliver leaves. The optimum adsortion-elution conditions are as follow: adsorption flow rate is 2 ml/min, crude liquid flew twice through the adsorption column,the optimum adsorbent is 40% ethanol.

Adsorption↗
PubMed1988

Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate.

The effects of topically applied curcumin, chlorogenic acid, caffeic acid, and ferulic acid on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced epidermal ornithine decarboxylase activity, epidermal DNA synthesis, and the promotion of skin tumors were evaluated in female CD-1 mice. Topical application of 0.5, 1, 3, or 10 mumol of curcumin inhibited by 31, 46, 84, or 98%, respectively, the induction of epidermal ornithine decarboxylase activity by 5 nmol of TPA. In an additional study, the topical application of 10 mumol of curcumin, chlorogenic acid, caffeic acid, or ferulic acid inhibited by 91, 25, 42, or 46%, respectively, the induction of ornithine decarboxylase activity by 5 nmol of TPA. The topical application of 10 mumol of curcumin together with 2 or 5 nmol of TPA inhibited the TPA-dependent stimulation of the incorporation of [3H]-thymidine into epidermal DNA by 49 or 29%, respectively, whereas lower doses of curcumin had little or no effect. Chlorogenic acid, caffeic acid, and ferulic acid were less effective than curcumin as inhibitors of the TPA-dependent stimulation of DNA synthesis. Topical application of 1, 3, or 10 mumol of curcumin together with 5 nmol of TPA twice weekly for 20 weeks to mice previously initiated with 7,12-dimethylbenz[a]anthracene inhibited the number of TPA-induced tumors per mouse by 39, 77, or 98%, respectively. Similar treatment of mice with 10 mumol of chlorogenic acid, caffeic acid, or ferulic acid together with 5 nmol of TPA inhibited the number of TPA-induced tumors per mouse by 60, 28, or 35%, respectively, and higher doses of the phenolic acids caused a more pronounced inhibition of tumor promotion. The possibility that curcumin could inhibit the action of arachidonic acid was evaluated by studying the effect of curcumin on arachidonic acid-induced edema of mouse ears. The topical application of 3 or 10 mumol of curcumin 30 min before the application of 1 mumol of arachidonic acid inhibited arachidonic acid-induced edema by 33 or 80%, respectively.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed1994

[Relationship between three extracting factors and extracting rate and stability of chlorogenic acid in the refining process of flos Lonicerae].

Content determination of chlorogenic acid in the extract of Flos Lonicerae by reversed-phase HPLC has proved that relatively long time boiling in weak acid conditions is beneficial to increasing the extracting rate of the acid. Also, verifying experiments have shown that chlorogenic acid remains stable in the above-said conditions.

Chlorogenic Acid↗
PubMed1975

Effect of chlorogenic acid in a casein diet for rats. Nutritional and pathological observations.

3-week-old male rats were fed on a casein diet containing 1% (w/w) of chlorogenic acid in order to find out if the ingestion of chlorogenic acid may be associated with a reduced utilization of dietary proteins or with causing other adverse effects. The protein efficiency ratio, biological value and digestibility of this diet did not differ from a corresponding casein diet free from chlorogenic acid. No change was observed in the nitrogen balance of the experimental rats. Neither did the rats show any change in hematological values or volumes and pH of the urine. Some deviation was noticed in the weights of kidneys and adrenals of the chlorogec acid-free casein diet. The findings that were made were normal in the microscopic examinations of various organs. Chlorogenic acid did not seem to influence the ultrastructure of the liver as revealed by electron microscopy.

Adrenal Glands↗
PubMed2000

Influence of storage upon light-induced chlorogenic acid accumulation in potato tubers (Solanum tuberosum L.).

The influence of 2 weeks and 3 months of dark storage upon light-induced chlorogenic acid accumulation within tuber tissue of four potato cultivars and upon 5-, 4-, and 3-caffeoylquinic acid concentrations within cv. King Edward was determined. Storage period significantly affected (P < 0.05) the magnitude of the light-induced chlorogenic acid response with accumulation rates 3-4 times higher in tubers exposed to light after 2 weeks compared with those placed under light after 3 months. Comparison of chlorogenic acid concentrations in controls after 2 and 3 months of dark storage indicated that tuber chlorogenic concentrations decline during prolonged cold store at 5 degrees C. Rates of accumulation in response to light were cultivar-dependent with cv. Fianna the most light-sensitive and cv. Maris Piper relatively light-insensitive. In virtually all cases exposure to sodium and fluorescent light promoted higher rates of accumulation than did exposure to high-pressure mercury light sources. Chlorogenic acid values steadily increased over 15 days of illumination with, in the majority of cases, no indication of cessation. Light exposure increased 5-, 4-, and 3-caffeoylquinic acid accumulation rates in cv. King Edward. Irrespective of storage period and light source, ratios of 5-:4-:3-caffeoylquinic acid were ca. 85:15:0 at day 0 and 52:42:6 by day 15.

Chlorogenic Acid↗
PubMed2005

Content of chalconaringenin and chlorogenic acid in cherry tomatoes is strongly reduced during postharvest ripening.

The contents of chalconaringenin, chlorogenic acid, rutin, ascorbic acid, lycopene, and beta-carotene were analyzed during postharvest and vine ripening of cherry tomatoes (Lycopersicon esculentumMill.) (cv. Jennita) produced in a greenhouse. A remarkable decrease in the content of chalconaringenin took place during postharvest ripening. The tomatoes were found to contain 15.26 mg 100 g(-1) fresh weight (FW) at harvest but held only 0.41 mg after 3 weeks at 20 degrees C in darkness. Chalconaringenin did not convert into naringenin. The content of chlorogenic acid fell from 0.51 to 0.06 mg 100 g(-1) FW at the same conditions. The content of rutin and that of total phenolics remained stable during postharvest ripening. The amounts of lycopene as well as beta-carotene and ascorbic acid increased during postharvest ripening. No significant change in the amount of methanol soluble antioxidants or total soluble solids was found during postharvest ripening of the tomato fruits. During vine ripening, the total amount of phenolics and that of soluble solids (% Brix) increased. The content of phenolics correlated well with the content of methanol soluble antioxidants (p < 0.001). The amount of ascorbic acid increased from 9.7 mg in green-yellow tomatoes to 17.1 mg 100 g(-1) FW in red tomatoes. The amount of chalconaringenin decreased to 8.16 mg 100 g(-1) FW, whereas no significant change was observed for chlorogenic acid or rutin. Possible causes for the decrease in chalconaringenin are discussed.

Ascorbic Acid↗
PubMed2005

Effect of roasting on the formation of chlorogenic acid lactones in coffee.

Of all plant constituents, coffee has one of the highest concentrations of chlorogenic acids. When roasting coffee, some of these are transformed into chlorogenic acid lactones (CGL). We have studied the formation of CGL during the roasting of coffee beans in Coffea arabica cv. Bourbon; C. arabicacv. Longberry; and C. canephora cv. Robusta. Individual CGL levels were determined by comparison of HPLC peaks with those of synthetic CGL standards. Seven CGL were identified: 3-caffeoylquinic-1,5-lactone (3-CQL), 4- caffeoylquinic-1,5-lactone (4-CQL), 3-coumaroylquinic-1,5-lactone (3-pCoQL), 4-coumaroylquinic-1,5-lactone (4-pCoQL), 3-feruloylquinic-1,5-lactone (3-FQL), 4-feruloylquinic-1,5-lactone (4-FQL), and 3,4-dicaffeoylquinic-1,5-lactone (3,4-diCQL). 3-CQL was the most abundant lactone in C. arabica and C. canephora, reaching peak values of 230 +/- 9 and 254 +/- 4 mg/100 g (dry weight), respectively, at light medium roast ( approximately 14% weight loss). 4-CQL was the second most abundant lactone (116 +/- 3 and 139 +/- 2 mg/100 g, respectively. The maximum amount of CGL represents approximately 30% of the available precursors. The relative levels of 3-CQL and 4-CQL in roasted coffee were reverse to those of their precursors in green coffee. This suggests that roasting causes isomerization of chlorogenic acids prior to the formation of lactones and that the levels of lactones in roasted coffee do not reflect the levels of precursors in green coffee.

Chlorogenic Acid↗
PubMed1984

[Occurrence of chlorogenic acids in potatoes].

Ten varieties of potato cultivated under the same conditions were analyzed for the occurrence of chlorogenic acids by high performance liquid chromatography. 3-O-caffeoylquinic acid (n-chlorogenic acid) is the predominant compound with 22-71 ppm, (on average of 41 ppm) depending on variety. 4-O-caffeoylquinic acid (phi 11 ppm), 5-O-caffeoylquinic acid (phi 7 ppm), 3,4-dicaffeoylquine acid (phi 3 ppm), and at times 3,5-dicaffeoylquinic acid (in traces) were also demonstrated. Caffeic acid compounds are not distributed uniformly in the potato tuber. They occur in strongly decreasing concentration from the outer sections to the inner ones. About 50% of these compounds are located in the potato peel and the adjoining tissue.

Chemical Phenomena↗
PubMed2006

Effects of chlorogenic acid and its metabolites on spontaneous locomotor activity in mice.

Chlorogenic acid possessed a weak caffeine-like psychostimulant property when assessed for its effect on spontaneous locomotor activity in mice. In the evaluation of the effects for the major metabolites of chlorogenic acid which were detected upon incubation with rat feces and/or excreted in urine after oral administration to rats, caffeic and m-coumaric acids were found to be the principal active metabolites, while the others contributed little to this caffeine-like psychostimulant activity.

Animals↗
PubMed2006

Characterization by LC-MS(n) of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids.

LC-MS4 has been used to detect and characterize in green coffee beans 12 chlorogenic acids not previously reported in nature. These comprise three isomeric dimethoxycinnamoylquinic acids (7-9) (Mr 382), three caffeoyl-dimethoxycinnamoylquinic acids (22, 24, and 26) (Mr 544), three diferuloylquinic acids (13-15) (Mr 544), and three feruloyl-dimethoxycinnamoylquinic acids (28, 30, and 32) (Mr 558). Structures have been assigned on the basis of LC-MS4 patterns of fragmentation and relative hydrophobicity and, in the case of the dimethoxycinnamoylquinic acids, by comparison with authentic standards. Several new structure-diagnostic fragmentations have been identified for use with diacyl-chlorogenic acids, for example, m/z 299 and 255 for C4 caffeoyl, m/z 313 and 269 for C4 feruloyl, nearly equal elimination of both cinnamoyl residues for vic-3,4-diacyl, and an increasing ratio of "dehydrated" ions to "non-dehydrated" ions at MS2 with increasing methylation of those cinnamoyl residues. Possible mechanisms have been proposed to account for the fragmentations observed. The mass spectrometric resolution of six isomeric chlorogenic acids (Mr 544) in a crude plant extract by fragment-targeted LC-MS2 and LC-MS3 experiments illustrates the analytical power and advantage of ion trap mass spectroscopy.

Chlorogenic Acid↗
PubMed2005

Insulin receptor exon 11+/- is expressed in Zucker (fa/fa) rats, and chlorogenic acid modifies their plasma insulin and liver protein and DNA.

In vivo studies confirmed that chlorogenic acid (CGA) improved glucose tolerance and mineral pool distribution in obese Zucker (fa/fa) rats. We found a significant decrease (P<.05) in postprandial blood glucose concentrations, which may have been due to an improved sensitivity to insulin. Impaired glucose tolerance and insulin resistance have been associated with differences in the hepatic mRNA expression of the spliced variants of the insulin receptor at exon 11. Spliced variants of the insulin receptor have not been studied in obese Zucker (fa/fa) rats, and no information exists about the effects of CGA in vivo as a possible insulin sensitizer. Thus, we studied the in vivo effect of CGA on plasma insulin concentrations during a glucose tolerance test, liver protein and DNA concentrations, the hepatic activity of glucose-6-phosphatase (G-6-PASE) and the mRNA expression of the two variants of the insulin receptor at exon 11. Zucker (fa/fa) rats were implanted with jugular vein catheters. Chlorogenic acid was administered (5 mg/kg body weight per day) for 3 weeks via intravenous infusion. In the CGA-treated group, areas under the curve (AUC) for blood glucose and plasma insulin improved (P<.005), and the protein and DNA concentrations in the liver increased (P<.05). No significant differences (P>.05) were found between groups for the hepatic G-6-PASE activity. The insulin receptor exon 11(+) and the exon 11(-) variants were expressed in the liver of Zucker (fa/fa) rats without significant changes (P>.05). Chlorogenic acid improved some cellular mechanisms that are stimulated by insulin.

Animals↗
PubMed2006

Determination of chlorogenic acid in rat plasma by high performance chromatography after peritoneal administration of compound Daqingye injection.

A simple and sensitive high performance liquid chromatographic method has been developed for the determination of chlorogenic acid (3-O-caffeoyl-D-quinic acid) in rat plasma and applied to its pharmacokinetic study in rats after peritoneal administration of compound Daqingye injection. Plasma samples are extracted with perchloric acid. HPLC analysis of the chlorogenic acid is performed on a C(18) reversed-phase column using methanol-water (80: 20, v/v, pH 2.8) as mobile phase with UV detector set at 327 nm. The standard curves are linear in the range of 0.200-10.0 microg/ml (r=0.9982). The inter- and intra-day precision (relative standard deviation) was less than 9% and the accuracy (relative error) was less than 10%. The limit of quantitation was 0.200 microg/ml. The plasma concentration of chlorogenic acid shows a C(max) of 7.53+/-0.52 microg/ml at 13.33+/-4.00 min with a t(1/2) of 59.10+/-5.42 min.

Animals↗
PubMed2006

Determination and pharmacokinetic study of syringin and chlorogenic acid in rat plasma after administration of Aidi lyophilizer.

A high-performance liquid chromatographic (HPLC) method was developed for the first time to simultaneously quantify syringin and chlorogenic acid in rat plasma using wavelength-transfer technology. The analysis was performed on a Diamonsil C(18) column (200 x 4.6 mm i.d., 5 microm particle size) with isocratic mobile phase consisting of acetonitrile-0.05% phosphoric acid (12:88, v/v). The linear ranges were 0.20-10 and 0.25-30 microg/mL, respectively. The lower limits of quantification were 0.20 and 0.25 microg/mL, respectively. The method was shown to be reproducible and reliable with intraday precision below 8.5 and 6.1%, interday precision below 7.1 and 5.5%, accuracy within +/-7.1 and +/-8.6%, and mean extraction recovery excess of 92.1 and 80.9%, respectively, which were all calculated from the blank plasma sample spiked with syringin and chlorogenic acid at three concentrations of 0.20, 1.0 and 6.0 microg/mL for syringin and 0.25, 2.0 and 20 microg/mL for chlorogenic acid. This method was validated for specificity, accuracy and precision and was successfully applied to the pharmacokinetic study of syringin and chlorogenic acid in rat plasma after intravenous administration of Aidi lyophilizer.

Animals↗
PubMed2000

[Quantitative determination of chlorogenic acid in eucommia leaf by high performance liquid chromatography].

An HPLC method for the quantitative determination of chlorogenic acid in Eucommia leaf was investigated. The sample was extracted with methanol solution containing 5% fomic acid and then analyzed by HPLC. The operating conditions were Shim-pack CLC-ODS column (6.0 mm i.d. x 150 mm, 5 microns) at 40 degrees C, mobile phase of methanol-0.01 mol/L KH2PO4(25:75, V/V; pH 3.9) at 1 mL/min and UV detection at 328 nm. Mercaptopurine was selected as the internal standard. There was a good linear relationship between the response (area ratio of chlorogenic acid to mercaptopurine) and the concentration of sample in the range of 25-300 mg/L for chlorogenic acid. The corresponding regression equation was Y = 8.0368X + 0.001275, r = 0.9999. The average recovery was 99.89% and RSD was 1.45%(n = 6). The results showed that this method is simple, specific and accurate.

Chlorogenic Acid↗
PubMed2006

Chlorogenic acid attenuates hypertension and improves endothelial function in spontaneously hypertensive rats.

BACKGROUND AND OBJECTIVES: Epidemiologic studies indicate that ingestion of vegetables and fruit inhibits the development of cardiovascular disease. Chlorogenic acids are abundant phenolic compounds contained in vegetables and fruits, but the impact of dietary chlorogenic acids on vascular function in hypertension is not known. We therefore examined the effects of 5-caffeoylquinic acid (CQA), a representative chlorogenic acid, on blood pressure and vascular function in age-matched normotensive Wistar-Kyoto rats and spontaneously hypertensive rats. METHODS AND RESULTS: A single ingestion of CQA (30-600 mg/kg) reduced blood pressure in spontaneously hypertensive rats, an effect that was blocked by administration of a nitric oxide synthase inhibitor, N(G)-nitro-L-arginine methyl ester. When spontaneously hypertensive rats were fed diets containing 0.5% CQA for 8 weeks (approximately 300 mg/kg per day), the development of hypertension was inhibited compared with the control diet group. CQA ingestion increased urinary excretion of nitric oxide metabolites and decreased urinary excretion of hydrogen peroxide; decreased NADPH-dependent superoxide anion production in the aorta, suggesting that dietary CQA inhibited vascular NADPH oxidase activity; significantly improved acetylcholine-induced endothelium-dependent vasodilation in the aorta; and markedly reduced the degree of immunohistochemical staining for nitrotyrosine and media hypertrophy in aorta sections. In contrast, CQA had no effects in Wistar-Kyoto rats. CONCLUSIONS: Dietary CQA reduces oxidative stress and improves nitric oxide bioavailability by inhibiting excessive production of reactive oxygen species in the vasculature, and leads to the attenuation of endothelial dysfunction, vascular hypertrophy, and hypertension in spontaneously hypertensive rats.

Animals↗