Purification and characterization of pentagalloylglucose, and α-glucosidase inhibitor/antibiotic from the freshwater green alga <i>Spirogyra varians</i>

Cannell, Richard J. P.; Farmer, Peter B.; Walker, John M.

doi:10.1042/bj2550937

Cited by 45 publications

(29 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Kinetic studies indicated that PGG was a mixed-type inhibitor of FabG with respect to NADPH. In another study, Cannell et al isolated a isomer of PGG, 3- O -digalloyl- 1,2,6-trigalloylglucose, from the freshwater green alga Spirogyra varians , and found that this compound irreversibly inhibited α-glucosidase and was more potent than PGG, 1 ,2, 3, 6-Tetra- O -galloylglucose or 1 ,2, 6-Tri- O -galloylglucose (75). The PGG isomer was proposed as the antibacterial agent in the methanol extract of Spirogyra varians .…”

Section: Other Biological Activitiesmentioning

confidence: 99%

Anti-Cancer, Anti-Diabetic and Other Pharmacologic and Biological Activities of Penta-Galloyl-Glucose

et al. 2009

View full text Add to dashboard Cite

Abstract1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose (PGG) is a polyphenolic compound highly enriched in a number of medicinal herbals. Several in vitro and a handful of in vivo studies have shown that PGG exhibits multiple biological activities which implicate a great potential for PGG in the therapy and prevention of several major diseases including cancer and diabetes. Chemically and functionally, PGG appears to be distinct from its constituent gallic acid or tea polyphenols. For anti-cancer activity, three published in vivo preclinical cancer model studies with PGG support promising efficacy to selectively inhibit malignancy without host toxicity. Potential mechanisms include antiangiogenesis, anti-proliferative actions through inhibition of DNA replicative synthesis and S-phase arrest and also G 1 arrest, induction of apoptosis, anti-inflammation and anti-oxidation. Putative molecular targets include p53, Stat3, Cox-2, VEGFR1, AP-1, SP-1, Nrf-2 and MMP-9. For antidiabetic activity, PGG and analogues appear to improve glucose uptake. However, very little is known about the absorption, pharmacokinetics and metabolism of PGG, nor its toxicity profile. The lack of large quantity of highly pure PGG has been a bottleneck limiting in vivo validation of cancer preventive and therapeutic efficacies in clinically relevant models.

show abstract

Section: Other Biological Activitiesmentioning

confidence: 99%

Anti-Cancer, Anti-Diabetic and Other Pharmacologic and Biological Activities of Penta-Galloyl-Glucose

et al. 2009

View full text Add to dashboard Cite

show abstract

“…This includes the genus Rhus, Schinus, Galla, Paeoniae Radix (the root of Paeonia lactiflora Pallas), Moutan cortex (the root cortex of Paeonia suffruicos), Macaranga tanariu, Quercus pedunculata, peony, and green alga Spirogyra varians. 5GG has been found to have various biological activities; it inhibits lipopolysaccharide-stimulated tumor necrosis factor-␣ secretion (22), gastric H ϩ ,K ϩ -ATPase (23), NADH dehydrogenase I/II (24 -27), xanthine oxidase (28), and ␣-glucosidase (29). 5GG also exhibits an endothelium-dependent vasodilator effect on isolated rat aorta (30) and manifests an anticonvulsant action (31).…”

mentioning

confidence: 99%

Induction of G1 Arrest and Apoptosis in Human Jurkat T Cells by Pentagalloylglucose through Inhibiting Proteasome Activity and Elevating p27Kip1, p21Cip1/WAF1, and Bax Proteins

Chen

Lin

2004

Journal of Biological Chemistry

View full text Add to dashboard Cite

Pentagalloylglucose, which is found in many medicinal plants, can arrest the cell cycle at G 1 phase through down-regulation of cyclin-dependent kinases 2 and 4 and up-regulation of the cyclin-dependent kinase inhibitors p27 Kip1 and p21 Cip1/WAF1 in human breast cancer cells. Pentagalloylglucose also induces apoptosis in human leukemic cells. However, the mechanisms by which pentagalloylglucose induces these effects is unclear. We now show that pentagalloylglucose inhibits the activities of purified 20 and 26 S proteasomes in vitro, the 26 S proteasome in Jurkat T cell lysates, and chymotrypsinlike activity of the 26 S proteasome in intact Jurkat T cells. The turnover of p27 Kip1 and p21 Cip1/WAF1 , which is necessary for cell cycle progression mediated by proteasome degradation, was disrupted by treatment of human Jurkat T cells with pentagalloylglucose. This was shown by cycloheximide treatment and in vivo pulsechase labeling experiments, and this effect correlated with the arrest of proliferation of Jurkat T cells at G 1 . Inhibition of the proteasome by pentagalloylglucose and by the proteasome inhibitor MG132 caused accumulation of ubiquitin-tagged proteins in Jurkat T cells. The addition of pentagalloylglucose to Jurkat T cells enhanced the stability of the proteasome substrate Bax and increased cytochrome c release and apoptosis. Our findings suggest a mechanism for the effect of pentagalloylglucose on the cell cycle in human leukemic cells: that pentagalloylglucose down-regulates proteasomemediated pathways because it is a proteasome inhibitor.In eukaryotic cells, there are two distinct proteolytic mechanisms essential for regulating levels of cellular proteins. One is lysosomal mediated degradation, which is involved in the breakdown of intracellular proteins under conditions of cellular stress, membrane-associated proteins, and proteins that have entered the cell by endocytosis. The ubiquitin-proteasome pathway is the other mechanism responsible for the turnover of intracellular proteins. This second system works by marking specific substrates with ubiquitins and degrading the marked proteins by the 26 S proteasome in an ATP-dependent manner.

show abstract

“…PGG, being a tannic acid, was first isolated and purified from the freshwater green alga Spirogyra varians or a Paraguayan crude drug, bMolle-iQ (Schinus terebinthifolius) [13,14], and it has also been synthesized [15]. It is reported to be a xanthine oxidase inhibitor and to exert an effect on mitochondrial respiration and oxidative phosphorylation through action on the membrane and on succinate dehydrogenase, NADH dehydrogenase and on the cytochrome c complex of mitochondria [14,16].…”

Section: Discussionmentioning

confidence: 98%

The screening and isolation of an effective anti-endotoxin monomer from Radix Paeoniae Rubra using affinity biosensor technology

Genfa

Zheng

Zhou

et al. 2005

International Immunopharmacology

View full text Add to dashboard Cite

Purification and characterization of pentagalloylglucose, and α-glucosidase inhibitor/antibiotic from the freshwater green alga Spirogyra varians

Abstract: An alpha-glucosidase inhibitor/antibiotic was purified from the freshwater green alga Spirogyra varians and was determined to be the pentagalloylglucose 3-O-digalloyl-1,2,6-trigalloylglucose.

Cited by 45 publications

References 10 publications

Anti-Cancer, Anti-Diabetic and Other Pharmacologic and Biological Activities of Penta-Galloyl-Glucose

Anti-Cancer, Anti-Diabetic and Other Pharmacologic and Biological Activities of Penta-Galloyl-Glucose

Induction of G1 Arrest and Apoptosis in Human Jurkat T Cells by Pentagalloylglucose through Inhibiting Proteasome Activity and Elevating p27Kip1, p21Cip1/WAF1, and Bax Proteins

The screening and isolation of an effective anti-endotoxin monomer from Radix Paeoniae Rubra using affinity biosensor technology

Contact Info

Product

Resources

About