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

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

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

Natural occurrence

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

Biosynthesis

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

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

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).[5]

Chemistry

Pentagalloyl glucose can undergo oxidation reactions which are depending on the pH.[9]

Research

Pentagalloyl glucose has been studied for its potential use as an antimicrobial, anti-inflammatory, anticarcinogenic, antidiabetic, and antioxidant.[10] It has also been studied for radioprotection.[11] 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]

Notes and References

  1. Cammann J, Denzel K, Schilling G, Gross GG . 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 . August 1989 . 2757399 . 10.1016/0003-9861(89)90161-6 .
  2. Hagerman AE, Rice ME, Ritchard NT . 10.1021/jf971097k. 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. 1998 .
  3. Gyémánt G, Zajácz A, Bécsi B, Ragunath C, Ramasubbu N, Erdodi F, Batta G, Kandra L . 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 . February 2009 . 19038368 . 10.1016/j.bbapap.2008.10.012 .
  4. 10.1016/S0031-9422(00)83125-8. Punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry. 24. 9. 2075. 1985. Tanaka. Takashi. Nonaka. Gen-Ichiro. Nishioka. Itsuo . 1985PChem..24.2075T.
  5. 10.1016/S0031-9422(98)00014-4. 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. 1998. Niemetz. Ruth. Gross. Georg G . 1998PChem..49..327N.
  6. 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 . 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 . June 2009 . 19457098 . 10.1111/j.1471-4159.2009.06069.x . 205620592 . free .
  7. 10.1016/j.fbp.2017.07.005. Extraction of antioxidants from mango seedkernel: Optimization assisted by microwave . Food and Bioproducts Processing. 105. 188–196. 2017. Torres-León. Cristian. Rojas. Romeo. Aguilar. Cristóbal . 102513001 .
  8. 10.1155/2020/5686029. 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. 2020. Kantapan. Jiraporn. Paksee. Siwaphon. Chawapun. Pornthip. Sangthong. Padchanee. Dechsupa. Nathupakorn. 32382295. free. 7193289.
  9. Chen Y, Hagerman AE . Reaction pH and protein affect the oxidation products of beta-pentagalloyl glucose . Free Radical Research . 39 . 2 . 117–24 . February 2005 . 15763959 . 10.1080/10715760400013789 . 85098105 .
  10. Torres-Leon C, Ventura-Sobrevilla J, Serna-Cock L, Ascacio-Valdes JA, Contreras-Esquivel J, Aguilar CN . 10.1016/j.jff.2017.07.045. Pentagalloylglucose (PGG): A valuable phenolic compound with functional properties. Journal of Functional Foods. 37. 176–189. 2017 .
  11. Park E, Lee NH, Baik JS, Jee Y . Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection . Phytotherapy Research . 22 . 8 . 1046–51 . August 2008 . 18570220 . 10.1002/ptr.2430 . 44278609 .
  12. Patnaik SS, Simionescu DT, Goergen CJ, Hoyt K, Sirsi S, Finol EA . Pentagalloyl Glucose and Its Functional Role in Vascular Health: Biomechanics and Drug-Delivery Characteristics . Annals of Biomedical Engineering . 47 . 1 . 39–59 . January 2019 . 30298373 . 6318003 . 10.1007/s10439-018-02145-5 .
  13. Patnaik. Sourav S.. Piskin. Senol. Pillalamarri. Narasimha Rao. Romero. Gabriela. Escobar. G. Patricia. Sprague. Eugene. Finol. Ender A.. 2019-07-03. Biomechanical Restoration Potential of Pentagalloyl Glucose after Arterial Extracellular Matrix Degeneration. Bioengineering. 6. 3. 58. 10.3390/bioengineering6030058. 2306-5354. 31277241. 6783915. free.
  14. Anderson. Jennifer L.. Niedert. Elizabeth E.. Patnaik. Sourav S.. Tang. Renxiang. Holloway. Riley L.. Osteguin. Vangelina. Finol. Ender A.. Goergen. Craig J.. January 2021. Animal Model Dependent Response to Pentagalloyl Glucose in Murine Abdominal Aortic Injury. Journal of Clinical Medicine. en. 10. 2. 219. 10.3390/jcm10020219. 33435461. 7827576. free.
  15. Arnold. Frances. Muzzio. Nicolas. Patnaik. Sourav S.. Finol. Ender A.. Romero. Gabriela. 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. 10.1021/acsami.1c05344. 1944-8252. 34030437. 235199265 .

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