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Chlorogenic acid

February 16, 2024

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis.[1] The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid.[2]

Chlorogenic acid
Names
Preferred IUPAC name
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Other names
3-(3,4-Dihydroxycinnamoyl)quinate
3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinate
3-Caffeoylquinic acid
3-CQA
3-O-Caffeoylquinic acid
Chlorogenate
Chlorogenic acid
Heriguard
3-trans-Caffeoylquinic acid
5-O-Caffeoylquinic acid
Identifiers
  • 202650-88-2 Y
  • 327-97-9 (E/Z)
3D model (JSmol)
  • Interactive image
3DMet
  • B01342
ChEBI
  • CHEBI:16112 N
ChEMBL
  • ChEMBL284616 N
ChemSpider
  • 1405788 Y
KEGG
  • C00852
  • 1794427
RTECS number
  • GU8480000
UNII
  • 318ADP12RI (E) Y
  • InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1 Y
    Key: CWVRJTMFETXNAD-JUHZACGLSA-N Y
  • InChI=1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
    Key: CWVRJTMFETXNAD-JUHZACGLBD
  • O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
Properties
C16H18O9
Molar mass 354.311 g·mol−1
Density 1.28 g/cm3
Melting point 207 to 209 °C (405 to 408 °F; 480 to 482 K)
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability (yellow): no hazard codeSpecial hazards (white): no code
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (ghenos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized.

Structural properties edit

Structurally, chlorogenic acid is the ester formed between caffeic acid and the 3-hydroxyl of L-quinic acid.[3] Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring: 4-O-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA) and 5-O-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not yet been reported.[2]

Structures having more than one caffeic acid group are called isochlorogenic acids, and can be found in coffee.[4] There are several isomers, such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid.[5] and cynarine (1,5-dicaffeoylquinic acid)

Biosynthesis and natural occurrence edit

 
4-Coumaroyl-CoA is the biosynthetic precursor to chlorogenic acid.

The biosynthetic precursor to chlorogenic acid is 4-coumaroyl-CoA, containing a single hydroxyl group on the aryl ring, which in turn is produced from cinnamic acid. The hydroxylation of the coumaryl ester, i.e. installing the second hydroxy group, is catalyzed by a cytochrome P450 enzyme.[6]

Chlorogenic acid can be found in the bamboo Phyllostachys edulis,[7] as well as in many other plants,[8] such as the shoots of common heather (Calluna vulgaris).[9]

In food edit

Chlorogenic acid and the related compounds cryptochlorogenic acid, and neochlorogenic acid have been found in the leaves of Hibiscus sabdariffa.[10] Isomers of chlorogenic acid are found in potatoes.[11] Chlorogenic acid is present in the flesh of eggplants,[12] peaches,[13] prunes[14] and coffee beans.[15]

Research and safety edit

Chlorogenic acid is under preliminary research for its possible biological effects.[16][17][18]

Chlorogenic acid has not been approved as a prescription drug or food additive recognized as a safe ingredient for foods or beverages.[19] There is not enough evidence to determine whether it is safe or effective for human health, and its use in high doses, such as excessive consumption of green coffee, may have adverse effects.[20]

Chlorogenic acid has been studied as a possible chemical sensitizer involved in respiratory allergy to certain plant materials.[21]

Nomenclature edit

The atom-numbering of chlorogenic acid can be ambiguous.[22] The order of numbering of atoms on the quinic acid ring was reversed in 1976 following IUPAC guidelines, with the consequence that 3-CQA became 5-CQA, and 5-CQA became 3-CQA. This article uses the original numbering, which was exclusive prior to 1976, (chlorogenic acid being 3-CQA, while neochlorogenic acid is 5-CQA). Thereafter researchers and manufacturers have been divided, with both numbering systems in use. Even the 1976 IUPAC recommendations are not entirely satisfactory when applied to some of the less common chlorogenic acids.[23]

References edit

  1. ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
  2. ^ a b Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids". Journal of Agricultural and Food Chemistry. 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369.
  3. ^ Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture. 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D.
  4. ^ Barnes, H. M.; Feldman, J. R.; White, W. V. (1950). "Isochlorogenic Acid. Isolation from Coffee and Structure Studies". J. Am. Chem. Soc. 72 (9): 4178–4182. doi:10.1021/ja01165a095.
  5. ^ Corse, J.; Lundin, R. E.; Waiss, A. C. (May 1965). "Identification of several components of isochlorogenic acid". Phytochemistry. 4 (3): 527–529. Bibcode:1965PChem...4..527C. doi:10.1016/S0031-9422(00)86209-3.
  6. ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3 (1): 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
  7. ^ Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin (2001). "Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis)". Journal of Agricultural and Food Chemistry. 49 (20): 4646–4652. doi:10.1021/jf010514x. PMID 11600002.
  8. ^ Clifford, M. N. (2003). "14. The analysis and characterization of chlorogenic acids and other cinnamates". In Santos-Buelga, C.; Williamson, G. (eds.). Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. pp. 314–337. ISBN 978-0-85404-580-8.
  9. ^ Jalal, Mahbubul A. F.; Read, David J.; Haslam, E. (1982). "Phenolic composition and its seasonal variation in Calluna vulgaris". Phytochemistry. 21 (6): 1397–1401. Bibcode:1982PChem..21.1397J. doi:10.1016/0031-9422(82)80150-7.
  10. ^ Zhen, Jing; Villani, Thomas S.; Guo, Yue; Qi, Yadong; Chin, Kit; Pan, Min-Hsiung; Ho, Chi-Tang; Simon, James E.; Wu, Qingli (2016). "Phytochemistry, antioxidant capacity, total phenolic content and anti-inflammatory activity of Hibiscus sabdariffa leaves". Food Chemistry. 190: 673–680. doi:10.1016/j.foodchem.2015.06.006. PMID 26213025.
  11. ^ Friedman, Mendel (1997). "Chemistry, Biochemistry, and Dietary Role of Potato Polyphenols. A Review". Journal of Agricultural and Food Chemistry. 45 (5): 1523–1540. doi:10.1021/jf960900s.
  12. ^ Luthria, Devanand L.; Mukhopadhyay, Sudarsan (2006). "Influence of Sample Preparation on Assay of Phenolic Acids from Eggplant". J. Agric. Food Chem. 54 (1): 41–47. doi:10.1021/jf0522457. PMID 16390175.
  13. ^ Cheng, G. W.; Crisosto, C. H. (September 1995). "Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue". Journal of the American Society for Horticultural Science. 120 (5): 835–838. doi:10.21273/JASHS.120.5.835.
  14. ^ Stacewicz-Sapuntzakis, M.; Bowen, P. E.; Hussain, E. A.; Damayanti-Wood, B. I.; Farnsworth, N. R. (2001). "Chemical composition and potential health effects of prunes: a functional food?". Critical Reviews in Food Science and Nutrition. 41 (4): 251–286. doi:10.1080/20014091091814. PMID 11401245. S2CID 31159565.
  15. ^ Macheiner, Lukas; Schmidt, Anatol; Schreiner, Matthias; Mayer, Helmut K. (2019). "Green coffee infusion as a source of caffeine and chlorogenic acid". Journal of Food Composition and Analysis. 84: 103307. doi:10.1016/j.jfca.2019.103307. S2CID 202882087.
  16. ^ Naveed, M; Hejazi, V; Abbas, M; Kamboh, AA; Khan, GJ; Shumzaid, M; Ahmad, F; Babazadeh, D; FangFang, X; Modarresi-Ghazani, F; WenHua, L; XiaoHui, Z (January 2018). "Chlorogenic acid (CGA): A pharmacological review and call for further research". Biomedicine & Pharmacotherapy. 97: 67–74. doi:10.1016/j.biopha.2017.10.064. PMID 29080460. Retrieved 10 September 2020.
  17. ^ Tajik, N; Tajik, M; Mack, I; Enck, P (2017). "The potential effects of chlorogenic acid, the main phenolic components in coffee, on health: A comprehensive review of the literature". European Journal of Nutrition. 56 (7): 2215–2244. doi:10.1007/s00394-017-1379-1. PMID 28391515. S2CID 5177390.
  18. ^ Onakpoya, I. J.; Spencer, E. A.; Thompson, M. J.; Heneghan, C. J. (19 June 2014). "The effect of chlorogenic acid on blood pressure: a systematic review and meta-analysis of randomized clinical trials". Journal of Human Hypertension. 29 (2): 77–81. doi:10.1038/jhh.2014.46. PMID 24943289. S2CID 2881228.
  19. ^ "Substances generally recognized as safe". Code of Federal Regulations, Title 21, Part 582, US Food and Drug Administration. 20 April 2022. Retrieved 25 April 2022.
  20. ^ "Green coffee". MedlinePlus, US National Library of Medicine. 11 August 2021. Retrieved 25 April 2022.
  21. ^ Freedman, Samuel O.; Shulman, Robert; Krupey, John; Sehon, A. H. (1964). "Antigenic properties of chlorogenic acid". The Journal of Allergy and Clinical Immunology. 35 (2): 97–107. doi:10.1016/0021-8707(64)90023-1. PMID 14129665.
  22. ^ Ventura, K. (2016). "Unremitting problems with chlorogenic acid nomenclature: a review". Química Nova. 39 (4): 530–533. doi:10.5935/0100-4042.20160063. hdl:10195/66766.
  23. ^ M. N. Clifford and L. Abranko. Some Notes on the Chlorogenic Acids. 1. Numbering and Nomenclature. ResearchGate. doi:10.13140/RG.2.2.22301.31202 2017.

February 16, 2024
chlorogenic, acid, ester, caffeic, acid, quinic, acid, functioning, intermediate, lignin, biosynthesis, term, chlorogenic, acids, refers, related, polyphenol, family, esters, including, hydroxycinnamic, acids, caffeic, acid, ferulic, acid, coumaric, acid, with. Chlorogenic acid CGA is the ester of caffeic acid and quinic acid functioning as an intermediate in lignin biosynthesis 1 The term chlorogenic acids refers to a related polyphenol family of esters including hydroxycinnamic acids caffeic acid ferulic acid and p coumaric acid with quinic acid 2 Chlorogenic acid NamesPreferred IUPAC name 1S 3R 4R 5R 3 2E 3 3 4 Dihydroxyphenyl prop 2 enoyl oxy 1 4 5 trihydroxycyclohexane 1 carboxylic acidOther names 3 3 4 Dihydroxycinnamoyl quinate3 3 4 Dihydroxycinnamoyl quinic acid3 Caffeoylquinate3 Caffeoylquinic acid3 CQA3 O Caffeoylquinic acidChlorogenateChlorogenic acidHeriguard3 trans Caffeoylquinic acid5 O Caffeoylquinic acidIdentifiersCAS Number 202650 88 2 Y327 97 9 E Z 3D model JSmol Interactive image3DMet B01342ChEBI CHEBI 16112 NChEMBL ChEMBL284616 NChemSpider 1405788 YKEGG C00852PubChem CID 1794427RTECS number GU8480000UNII 318ADP12RI E YInChI InChI 1S C16H18O9 c17 9 3 1 8 5 10 9 18 2 4 13 20 25 12 7 16 24 15 22 23 6 11 19 14 12 21 h1 5 11 12 14 17 19 21 24H 6 7H2 H 22 23 b4 2 t11 12 14 16 m1 s1 YKey CWVRJTMFETXNAD JUHZACGLSA N YInChI 1 C16H18O9 c17 9 3 1 8 5 10 9 18 2 4 13 20 25 12 7 16 24 15 22 23 6 11 19 14 12 21 h1 5 11 12 14 17 19 21 24H 6 7H2 H 22 23 b4 2 t11 12 14 16 m1 s1Key CWVRJTMFETXNAD JUHZACGLBDSMILES O C O C 2 O C C H O C H O C H OC O C C c1ccc O c O c1 C2PropertiesChemical formula C 16H 18O 9Molar mass 354 311 g mol 1Density 1 28 g cm3Melting point 207 to 209 C 405 to 408 F 480 to 482 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501NFPA 704 fire diamond 10Safety data sheet SDS External MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Despite the chloro of the name chlorogenic acids contain no chlorine Instead the name comes from the Greek xlwros khloros light green and genos ghenos a suffix meaning giving rise to pertaining to the green color produced when chlorogenic acids are oxidized Contents 1 Structural properties 2 Biosynthesis and natural occurrence 2 1 In food 3 Research and safety 4 Nomenclature 5 ReferencesStructural properties editStructurally chlorogenic acid is the ester formed between caffeic acid and the 3 hydroxyl of L quinic acid 3 Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring 4 O caffeoylquinic acid cryptochlorogenic acid or 4 CQA and 5 O caffeoylquinic acid neochlorogenic acid or 5 CQA The epimer at position 1 has not yet been reported 2 Structures having more than one caffeic acid group are called isochlorogenic acids and can be found in coffee 4 There are several isomers such as 3 4 dicaffeoylquinic acid and 3 5 dicaffeoylquinic acid 5 and cynarine 1 5 dicaffeoylquinic acid Biosynthesis and natural occurrence edit nbsp 4 Coumaroyl CoA is the biosynthetic precursor to chlorogenic acid The biosynthetic precursor to chlorogenic acid is 4 coumaroyl CoA containing a single hydroxyl group on the aryl ring which in turn is produced from cinnamic acid The hydroxylation of the coumaryl ester i e installing the second hydroxy group is catalyzed by a cytochrome P450 enzyme 6 Chlorogenic acid can be found in the bamboo Phyllostachys edulis 7 as well as in many other plants 8 such as the shoots of common heather Calluna vulgaris 9 In food edit Chlorogenic acid and the related compounds cryptochlorogenic acid and neochlorogenic acid have been found in the leaves of Hibiscus sabdariffa 10 Isomers of chlorogenic acid are found in potatoes 11 Chlorogenic acid is present in the flesh of eggplants 12 peaches 13 prunes 14 and coffee beans 15 Research and safety editChlorogenic acid is under preliminary research for its possible biological effects 16 17 18 Chlorogenic acid has not been approved as a prescription drug or food additive recognized as a safe ingredient for foods or beverages 19 There is not enough evidence to determine whether it is safe or effective for human health and its use in high doses such as excessive consumption of green coffee may have adverse effects 20 Chlorogenic acid has been studied as a possible chemical sensitizer involved in respiratory allergy to certain plant materials 21 Nomenclature editThe atom numbering of chlorogenic acid can be ambiguous 22 The order of numbering of atoms on the quinic acid ring was reversed in 1976 following IUPAC guidelines with the consequence that 3 CQA became 5 CQA and 5 CQA became 3 CQA This article uses the original numbering which was exclusive prior to 1976 chlorogenic acid being 3 CQA while neochlorogenic acid is 5 CQA Thereafter researchers and manufacturers have been divided with both numbering systems in use Even the 1976 IUPAC recommendations are not entirely satisfactory when applied to some of the less common chlorogenic acids 23 References edit Boerjan Wout Ralph John Baucher Marie 2003 Lignin biosynthesis Annual Review of Plant Biology 54 519 546 doi 10 1146 annurev arplant 54 031902 134938 PMID 14503002 a b Clifford M N Johnston K L Knigh S Kuhnert N 2003 Hierarchical Scheme for LC MSn Identification of Chlorogenic Acids Journal of Agricultural and Food Chemistry 51 10 2900 2911 doi 10 1021 jf026187q PMID 12720369 Clifford M N 1999 Chlorogenic acids and other cinnamates nature occurrence and dietary burden Journal of the Science of Food and Agriculture 79 3 362 372 doi 10 1002 SICI 1097 0010 19990301 79 3 lt 362 AID JSFA256 gt 3 0 CO 2 D Barnes H M Feldman J R White W V 1950 Isochlorogenic Acid Isolation from Coffee and Structure Studies J Am Chem Soc 72 9 4178 4182 doi 10 1021 ja01165a095 Corse J Lundin R E Waiss A C May 1965 Identification of several components of isochlorogenic acid Phytochemistry 4 3 527 529 Bibcode 1965PChem 4 527C doi 10 1016 S0031 9422 00 86209 3 Vogt T 2010 Phenylpropanoid Biosynthesis Molecular Plant 3 1 2 20 doi 10 1093 mp ssp106 PMID 20035037 Kweon Mee Hyang Hwang Han Joon Sung Ha Chin 2001 Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo Phyllostachys edulis Journal of Agricultural and Food Chemistry 49 20 4646 4652 doi 10 1021 jf010514x PMID 11600002 Clifford M N 2003 14 The analysis and characterization of chlorogenic acids and other cinnamates In Santos Buelga C Williamson G eds Methods in Polyphenol Analysis Cambridge Royal Society of Chemistry pp 314 337 ISBN 978 0 85404 580 8 Jalal Mahbubul A F Read David J Haslam E 1982 Phenolic composition and its seasonal variation in Calluna vulgaris Phytochemistry 21 6 1397 1401 Bibcode 1982PChem 21 1397J doi 10 1016 0031 9422 82 80150 7 Zhen Jing Villani Thomas S Guo Yue Qi Yadong Chin Kit Pan Min Hsiung Ho Chi Tang Simon James E Wu Qingli 2016 Phytochemistry antioxidant capacity total phenolic content and anti inflammatory activity of Hibiscus sabdariffa leaves Food Chemistry 190 673 680 doi 10 1016 j foodchem 2015 06 006 PMID 26213025 Friedman Mendel 1997 Chemistry Biochemistry and Dietary Role of Potato Polyphenols A Review Journal of Agricultural and Food Chemistry 45 5 1523 1540 doi 10 1021 jf960900s Luthria Devanand L Mukhopadhyay Sudarsan 2006 Influence of Sample Preparation on Assay of Phenolic Acids from Eggplant J Agric Food Chem 54 1 41 47 doi 10 1021 jf0522457 PMID 16390175 Cheng G W Crisosto C H September 1995 Browning Potential Phenolic Composition and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue Journal of the American Society for Horticultural Science 120 5 835 838 doi 10 21273 JASHS 120 5 835 Stacewicz Sapuntzakis M Bowen P E Hussain E A Damayanti Wood B I Farnsworth N R 2001 Chemical composition and potential health effects of prunes a functional food Critical Reviews in Food Science and Nutrition 41 4 251 286 doi 10 1080 20014091091814 PMID 11401245 S2CID 31159565 Macheiner Lukas Schmidt Anatol Schreiner Matthias Mayer Helmut K 2019 Green coffee infusion as a source of caffeine and chlorogenic acid Journal of Food Composition and Analysis 84 103307 doi 10 1016 j jfca 2019 103307 S2CID 202882087 Naveed M Hejazi V Abbas M Kamboh AA Khan GJ Shumzaid M Ahmad F Babazadeh D FangFang X Modarresi Ghazani F WenHua L XiaoHui Z January 2018 Chlorogenic acid CGA A pharmacological review and call for further research Biomedicine amp Pharmacotherapy 97 67 74 doi 10 1016 j biopha 2017 10 064 PMID 29080460 Retrieved 10 September 2020 Tajik N Tajik M Mack I Enck P 2017 The potential effects of chlorogenic acid the main phenolic components in coffee on health A comprehensive review of the literature European Journal of Nutrition 56 7 2215 2244 doi 10 1007 s00394 017 1379 1 PMID 28391515 S2CID 5177390 Onakpoya I J Spencer E A Thompson M J Heneghan C J 19 June 2014 The effect of chlorogenic acid on blood pressure a systematic review and meta analysis of randomized clinical trials Journal of Human Hypertension 29 2 77 81 doi 10 1038 jhh 2014 46 PMID 24943289 S2CID 2881228 Substances generally recognized as safe Code of Federal Regulations Title 21 Part 582 US Food and Drug Administration 20 April 2022 Retrieved 25 April 2022 Green coffee MedlinePlus US National Library of Medicine 11 August 2021 Retrieved 25 April 2022 Freedman Samuel O Shulman Robert Krupey John Sehon A H 1964 Antigenic properties of chlorogenic acid The Journal of Allergy and Clinical Immunology 35 2 97 107 doi 10 1016 0021 8707 64 90023 1 PMID 14129665 Ventura K 2016 Unremitting problems with chlorogenic acid nomenclature a review Quimica Nova 39 4 530 533 doi 10 5935 0100 4042 20160063 hdl 10195 66766 M N Clifford and L Abranko Some Notes on the Chlorogenic Acids 1 Numbering and Nomenclature ResearchGate doi 10 13140 RG 2 2 22301 31202 2017 Retrieved from https en wikipedia org w index php title Chlorogenic acid amp oldid 1193929790, wikipedia, wiki, book, books, library,

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