fbpx
Wikipedia

1,2,3,4,6-Pentagalloyl glucose

April 12, 2024

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.[1]

1,2,3,4,6-Pentagalloyl glucose
Names
IUPAC name
β-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate)
Systematic IUPAC name
(2S,3R,4S,5R,6R)-6-{[(3,4,5-Trihydroxybenzoyl)oxy]methyl}oxane-2,3,4,5-tetrayl tetrakis(3,4,5-trihydroxybenzoate)
Other names
1,2,3,4,6-Penta-O-galloyl-β-D-glucose
1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose
beta-Penta-O-galloyl-glucose
PGG
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose
Identifiers
  • 14937-32-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18082 Y
ChEMBL
  • ChEMBL382408 Y
ChemSpider
  • 58735 Y
ECHA InfoCard 100.113.489
  • 65238
UNII
  • 3UI3K8W93I Y
  • InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1 Y
    Key: QJYNZEYHSMRWBK-NIKIMHBISA-N Y
  • C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
Properties
C41H32O26
Molar mass 940.681 g·mol−1
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 ?)

Pentagalloyl glucose can precipitate proteins,[2] including human salivary α-amylase.[3]

Natural occurrence edit

1,2,3,4,6-Pentagalloyl glucose can be found in Punica granatum (pomegranate),[4] Elaeocarpus sylvestris,[5] Rhus typhina (Staghorn sumac),[6] Paeonia suffruticosa (Tree Peony),.,[7] Mangifera indica (mango) [8] and Bouea macrophylla Griffith (maprang).[9]

Biosynthesis edit

The enzyme beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase uses 1-O-galloyl-beta-D-glucose and 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose to produce D-glucose and pentagalloyl glucose.

Metabolism edit

Tellimagrandin II is formed from pentagalloyl glucose by oxidative dehydrogenation and coupling of 2 galloyl groups.

β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase is an enzyme found in the leaves of Rhus typhina that catalyzes the galloylation of 1,2,3,4,6-penta-O-galloyl-β-D-glucose to 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-β-d-glucose (hexa-galloylglucose).[6]

Chemistry edit

Pentagalloyl glucose can undergo oxidation reactions which are depending on the pH.[10]

Research edit

Pentagalloyl glucose has been studied for its potential use as an antimicrobial, anti-inflammatory, anticarcinogenic, antidiabetic, and antioxidant.[11] It has also been studied for radioprotection.[5] This compound helps stabilize the elastin and collagen in vascular tissues[12] and restores the biomechanical properties of arterial ECM.[13] In addition, pentagalloyl glucose has shown to reduce arterial calcification and helps promote extracellular matrix preservation in animal models of abdominal aortic aneurysm.[14] In vitro studies with mouse C2C12 myoblast cells have shown the PGG helps in lowering reactive oxygen species (ROS) and matrix metalloproteinase-2 (MMP-2) expression in a dose-dependent manner. [15]

References edit

  1. ^ Cammann J, Denzel K, Schilling G, Gross GG (August 1989). "Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose". Archives of Biochemistry and Biophysics. 273 (1): 58–63. doi:10.1016/0003-9861(89)90161-6. PMID 2757399.
  2. ^ Hagerman AE, Rice ME, Ritchard NT (1998). "Mechanisms of Protein Precipitation for Two Tannins, Pentagalloyl Glucose and Epicatechin16(4→8) Catechin (Procyanidin)". Journal of Agricultural and Food Chemistry. 46 (7): 2590–2595. doi:10.1021/jf971097k.
  3. ^ Gyémánt G, Zajácz A, Bécsi B, Ragunath C, Ramasubbu N, Erdodi F, Batta G, Kandra L (February 2009). "Evidence for pentagalloyl glucose binding to human salivary alpha-amylase through aromatic amino acid residues". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1794 (2): 291–6. doi:10.1016/j.bbapap.2008.10.012. PMID 19038368.
  4. ^ Tanaka T, Nonaka GI, Nishioka I (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075. Bibcode:1985PChem..24.2075T. doi:10.1016/S0031-9422(00)83125-8.
  5. ^ a b Park E, Lee NH, Baik JS, Jee Y (August 2008). "Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection". Phytotherapy Research. 22 (8): 1046–51. doi:10.1002/ptr.2430. PMID 18570220. S2CID 44278609.
  6. ^ a b Niemetz R, Gross GG (1998). "Gallotannin biosynthesis: Purification of β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase from sumac leavesfn1fn1In honour of Professor G. H. Neil Towers' 75th birthday". Phytochemistry. 49 (2): 327. Bibcode:1998PChem..49..327N. doi:10.1016/S0031-9422(98)00014-4.
  7. ^ Fujiwara H, Tabuchi M, Yamaguchi T, Iwasaki K, Furukawa K, Sekiguchi K, Ikarashi Y, Kudo Y, Higuchi M, Saido TC, Maeda S, Takashima A, Hara M, Yaegashi N, Kase Y, Arai H (June 2009). "A traditional medicinal herb Paeonia suffruticosa and its active constituent 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose have potent anti-aggregation effects on Alzheimer's amyloid beta proteins in vitro and in vivo". Journal of Neurochemistry. 109 (6): 1648–57. doi:10.1111/j.1471-4159.2009.06069.x. PMID 19457098. S2CID 205620592.
  8. ^ Torres-León C, Rojas R, Aguilar C (2017). "Extraction of antioxidants from mango seedkernel: Optimization assisted by microwave". Food and Bioproducts Processing. 105: 188–196. doi:10.1016/j.fbp.2017.07.005. S2CID 102513001.
  9. ^ Kantapan J, Paksee S, Chawapun P, Sangthong P, Dechsupa N (2020). "Pentagalloyl Glucose- and Ethyl Gallate-Rich Extract from Maprang Seeds Induce Apoptosis in MCF-7 Breast Cancer Cells through Mitochondria-Mediated Pathway". Evidence-Based Complementary and Alternative Medicine. 2020: 1–19. doi:10.1155/2020/5686029. PMC 7193289. PMID 32382295.
  10. ^ Chen Y, Hagerman AE (February 2005). "Reaction pH and protein affect the oxidation products of beta-pentagalloyl glucose". Free Radical Research. 39 (2): 117–24. doi:10.1080/10715760400013789. PMID 15763959. S2CID 85098105.
  11. ^ Torres-Leon C, Ventura-Sobrevilla J, Serna-Cock L, Ascacio-Valdes JA, Contreras-Esquivel J, Aguilar CN (2017). "Pentagalloylglucose (PGG): A valuable phenolic compound with functional properties". Journal of Functional Foods. 37: 176–189. doi:10.1016/j.jff.2017.07.045.
  12. ^ Patnaik SS, Simionescu DT, Goergen CJ, Hoyt K, Sirsi S, Finol EA (January 2019). "Pentagalloyl Glucose and Its Functional Role in Vascular Health: Biomechanics and Drug-Delivery Characteristics". Annals of Biomedical Engineering. 47 (1): 39–59. doi:10.1007/s10439-018-02145-5. PMC 6318003. PMID 30298373.
  13. ^ Patnaik SS, Piskin S, Pillalamarri NR, Romero G, Escobar GP, Sprague E, Finol EA (2019-07-03). "Biomechanical Restoration Potential of Pentagalloyl Glucose after Arterial Extracellular Matrix Degeneration". Bioengineering. 6 (3): 58. doi:10.3390/bioengineering6030058. ISSN 2306-5354. PMC 6783915. PMID 31277241.
  14. ^ Anderson JL, Niedert EE, Patnaik SS, Tang R, Holloway RL, Osteguin V, Finol EA, Goergen CJ (January 2021). "Animal Model Dependent Response to Pentagalloyl Glucose in Murine Abdominal Aortic Injury". Journal of Clinical Medicine. 10 (2): 219. doi:10.3390/jcm10020219. PMC 7827576. PMID 33435461.
  15. ^ Arnold F, Muzzio N, Patnaik SS, Finol EA, Romero G (2021-05-24). "Pentagalloyl Glucose-Laden Poly(lactide-co-glycolide) Nanoparticles for the Biomechanical Extracellular Matrix Stabilization of an In Vitro Abdominal Aortic Aneurysm Model". ACS Applied Materials & Interfaces. 13 (22): 25771–25782. doi:10.1021/acsami.1c05344. ISSN 1944-8252. PMID 34030437. S2CID 235199265.

April 12, 2024
pentagalloyl, glucose, pentagalloylglucose, pentagallic, acid, ester, glucose, gallotannin, precursor, ellagitannins, namesiupac, name, glucopyranose, pentakis, trihydroxybenzoate, systematic, iupac, name, trihydroxybenzoyl, methyl, oxane, tetrayl, tetrakis, t. 1 2 3 4 6 Pentagalloylglucose is the pentagallic acid ester of glucose It is a gallotannin and the precursor of ellagitannins 1 1 2 3 4 6 Pentagalloyl glucose NamesIUPAC name b D Glucopyranose pentakis 3 4 5 trihydroxybenzoate Systematic IUPAC name 2S 3R 4S 5R 6R 6 3 4 5 Trihydroxybenzoyl oxy methyl oxane 2 3 4 5 tetrayl tetrakis 3 4 5 trihydroxybenzoate Other names 1 2 3 4 6 Penta O galloyl b D glucose1 2 3 4 6 Pentakis O galloyl beta D glucosebeta Penta O galloyl glucosePGG1 2 3 4 6 Penta O galloyl beta D glucoseIdentifiersCAS Number 14937 32 7 Y3D model JSmol Interactive imageChEBI CHEBI 18082 YChEMBL ChEMBL382408 YChemSpider 58735 YECHA InfoCard 100 113 489PubChem CID 65238UNII 3UI3K8W93I YInChI InChI 1S C41H32O26 c42 17 1 12 2 18 43 28 17 52 36 57 62 11 27 33 64 37 58 13 3 19 44 29 53 20 45 4 13 34 65 38 59 14 5 21 46 30 54 22 47 6 14 35 66 39 60 15 7 23 48 31 55 24 49 8 15 41 63 27 67 40 61 16 9 25 50 32 56 26 51 10 16 h1 10 27 33 35 41 56H 11H2 t27 33 34 35 41 m1 s1 YKey QJYNZEYHSMRWBK NIKIMHBISA N YSMILES C1 C C C C C1O O O C O OCC2C C C C O2 OC O C3 CC C C C3 O O O OC O C4 CC C C C4 O O O OC O C5 CC C C C5 O O O OC O C6 CC C C C6 O O OPropertiesChemical formula C 41H 32O 26Molar mass 940 681 g mol 1Except 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 Pentagalloyl glucose can precipitate proteins 2 including human salivary a amylase 3 Contents 1 Natural occurrence 2 Biosynthesis 3 Metabolism 4 Chemistry 5 Research 6 ReferencesNatural occurrence edit1 2 3 4 6 Pentagalloyl glucose can be found in Punica granatum pomegranate 4 Elaeocarpus sylvestris 5 Rhus typhina Staghorn sumac 6 Paeonia suffruticosa Tree Peony 7 Mangifera indica mango 8 and Bouea macrophylla Griffith maprang 9 Biosynthesis editThe enzyme beta glucogallin tetrakisgalloylglucose O galloyltransferase uses 1 O galloyl beta D glucose and 1 2 3 6 tetrakis O galloyl beta D glucose to produce D glucose and pentagalloyl glucose Metabolism editTellimagrandin II is formed from pentagalloyl glucose by oxidative dehydrogenation and coupling of 2 galloyl groups b glucogallin 1 2 3 4 6 pentagalloyl b d glucose galloyltransferase is an enzyme found in the leaves of Rhus typhina that catalyzes the galloylation of 1 2 3 4 6 penta O galloyl b D glucose to 3 O digalloyl 1 2 4 6 tetra O galloyl b d glucose hexa galloylglucose 6 Chemistry editPentagalloyl glucose can undergo oxidation reactions which are depending on the pH 10 Research editPentagalloyl glucose has been studied for its potential use as an antimicrobial anti inflammatory anticarcinogenic antidiabetic and antioxidant 11 It has also been studied for radioprotection 5 This compound helps stabilize the elastin and collagen in vascular tissues 12 and restores the biomechanical properties of arterial ECM 13 In addition pentagalloyl glucose has shown to reduce arterial calcification and helps promote extracellular matrix preservation in animal models of abdominal aortic aneurysm 14 In vitro studies with mouse C2C12 myoblast cells have shown the PGG helps in lowering reactive oxygen species ROS and matrix metalloproteinase 2 MMP 2 expression in a dose dependent manner 15 References edit Cammann J Denzel K Schilling G Gross GG August 1989 Biosynthesis of gallotannins beta glucogallin dependent formation of 1 2 3 4 6 pentagalloylglucose by enzymatic galloylation of 1 2 3 6 tetragalloylglucose Archives of Biochemistry and Biophysics 273 1 58 63 doi 10 1016 0003 9861 89 90161 6 PMID 2757399 Hagerman AE Rice ME Ritchard NT 1998 Mechanisms of Protein Precipitation for Two Tannins Pentagalloyl Glucose and Epicatechin16 4 8 Catechin Procyanidin Journal of Agricultural and Food Chemistry 46 7 2590 2595 doi 10 1021 jf971097k Gyemant G Zajacz A Becsi B Ragunath C Ramasubbu N Erdodi F Batta G Kandra L February 2009 Evidence for pentagalloyl glucose binding to human salivary alpha amylase through aromatic amino acid residues Biochimica et Biophysica Acta BBA Proteins and Proteomics 1794 2 291 6 doi 10 1016 j bbapap 2008 10 012 PMID 19038368 Tanaka T Nonaka GI Nishioka I 1985 Punicafolin an ellagitannin from the leaves of Punica granatum Phytochemistry 24 9 2075 Bibcode 1985PChem 24 2075T doi 10 1016 S0031 9422 00 83125 8 a b Park E Lee NH Baik JS Jee Y August 2008 Elaeocarpus sylvestris modulates gamma ray induced immunosuppression in mice implications in radioprotection Phytotherapy Research 22 8 1046 51 doi 10 1002 ptr 2430 PMID 18570220 S2CID 44278609 a b Niemetz R Gross GG 1998 Gallotannin biosynthesis Purification of b glucogallin 1 2 3 4 6 pentagalloyl b d glucose galloyltransferase from sumac leavesfn1fn1In honour of Professor G H Neil Towers 75th birthday Phytochemistry 49 2 327 Bibcode 1998PChem 49 327N doi 10 1016 S0031 9422 98 00014 4 Fujiwara H Tabuchi M Yamaguchi T Iwasaki K Furukawa K Sekiguchi K Ikarashi Y Kudo Y Higuchi M Saido TC Maeda S Takashima A Hara M Yaegashi N Kase Y Arai H June 2009 A traditional medicinal herb Paeonia suffruticosa and its active constituent 1 2 3 4 6 penta O galloyl beta D glucopyranose have potent anti aggregation effects on Alzheimer s amyloid beta proteins in vitro and in vivo Journal of Neurochemistry 109 6 1648 57 doi 10 1111 j 1471 4159 2009 06069 x PMID 19457098 S2CID 205620592 Torres Leon C Rojas R Aguilar C 2017 Extraction of antioxidants from mango seedkernel Optimization assisted by microwave Food and Bioproducts Processing 105 188 196 doi 10 1016 j fbp 2017 07 005 S2CID 102513001 Kantapan J Paksee S Chawapun P Sangthong P Dechsupa N 2020 Pentagalloyl Glucose and Ethyl Gallate Rich Extract from Maprang Seeds Induce Apoptosis in MCF 7 Breast Cancer Cells through Mitochondria Mediated Pathway Evidence Based Complementary and Alternative Medicine 2020 1 19 doi 10 1155 2020 5686029 PMC 7193289 PMID 32382295 Chen Y Hagerman AE February 2005 Reaction pH and protein affect the oxidation products of beta pentagalloyl glucose Free Radical Research 39 2 117 24 doi 10 1080 10715760400013789 PMID 15763959 S2CID 85098105 Torres Leon C Ventura Sobrevilla J Serna Cock L Ascacio Valdes JA Contreras Esquivel J Aguilar CN 2017 Pentagalloylglucose PGG A valuable phenolic compound with functional properties Journal of Functional Foods 37 176 189 doi 10 1016 j jff 2017 07 045 Patnaik SS Simionescu DT Goergen CJ Hoyt K Sirsi S Finol EA January 2019 Pentagalloyl Glucose and Its Functional Role in Vascular Health Biomechanics and Drug Delivery Characteristics Annals of Biomedical Engineering 47 1 39 59 doi 10 1007 s10439 018 02145 5 PMC 6318003 PMID 30298373 Patnaik SS Piskin S Pillalamarri NR Romero G Escobar GP Sprague E Finol EA 2019 07 03 Biomechanical Restoration Potential of Pentagalloyl Glucose after Arterial Extracellular Matrix Degeneration Bioengineering 6 3 58 doi 10 3390 bioengineering6030058 ISSN 2306 5354 PMC 6783915 PMID 31277241 Anderson JL Niedert EE Patnaik SS Tang R Holloway RL Osteguin V Finol EA Goergen CJ January 2021 Animal Model Dependent Response to Pentagalloyl Glucose in Murine Abdominal Aortic Injury Journal of Clinical Medicine 10 2 219 doi 10 3390 jcm10020219 PMC 7827576 PMID 33435461 Arnold F Muzzio N Patnaik SS Finol EA Romero G 2021 05 24 Pentagalloyl Glucose Laden Poly lactide co glycolide Nanoparticles for the Biomechanical Extracellular Matrix Stabilization of an In Vitro Abdominal Aortic Aneurysm Model ACS Applied Materials amp Interfaces 13 22 25771 25782 doi 10 1021 acsami 1c05344 ISSN 1944 8252 PMID 34030437 S2CID 235199265 Retrieved from https en wikipedia org w index php title 1 2 3 4 6 Pentagalloyl glucose amp oldid 1209623363, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.