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Planta Med 2013; 79(17): 1674-1679
DOI: 10.1055/s-0033-1350925
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

New Phenolics from the Flowers of Punica granatum and Their In Vitro α-Glucosidase Inhibitory Activities

Tao Yuan
1   Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island, United States
,
Chunpeng Wan
1   Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island, United States
,
Hang Ma
1   Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island, United States
,
Navindra P. Seeram
1   Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island, United States
› Author Affiliations
Further Information

Publication History

received 06 August 2013
revised 11 September 2013

accepted 12 September 2013

Publication Date:
09 October 2013 (online)

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Abstract

Two new phenolics, a 3-substituted coumarin, 7,8-dihydroxy-3-carboxymethylcoumarin-5-carboxylic acid (1), and a hydrolyzable tannin, namely punicatannin C (2), together with 10 known phenolics, were isolated from the flowers of pomegranate (Punica granatum). Their structures were determined on the basis of extensive spectroscopic analyses including HRESIMS, 1D and 2D NMR data. All the isolates were evaluated for in vitro α-glucosidase inhibitory activities.

Key words

pomegranate - Punica granatum - Punicaceae - coumarin - hydrolyzable tannin - α-glucosidase inhibition

Supporting Information

 

  • References

  • 1 Seeram NP, Schulman RN, Heber D. Pomegranates: ancient roots to modern medicine. Boca Raton: Taylor & Francis; 2006
    Google Scholar
  • 2 Huang THW, Peng G, Kota BP, Li GQ, Yamahara J, Roufogalis BD, Li Y. Anti-diabetic action of Punica granatum flower extract: activation of PPAR-γ and identification of an active component. Toxicol Appl Pharmacol 2005; 207: 160-169
    CrossrefPubMedGoogle Scholar
  • 3 Li Y, Wen S, Kota BP, Peng G, Li GQ, Yamahara J, Roufogalis BD. Punica granatum flower extract, a potent α-glucosidase inhibitor, improves postprandial hyperglycemia in Zucker diabetic fatty rats. J Ethnopharmacol 2005; 99: 239-244
    CrossrefPubMedGoogle Scholar
  • 4 Pereira AC, Arruda MSP, da Silva EAS, da Silva MN, Lemos VS, Cortes SF. Inhibition of α-glucosidase and hypoglycemic effect of stilbenes from the Amazonian plant Deguelia rufescens var. urucu (Ducke) A. M. G. Azevedo (Leguminosae). Planta Med 2012; 78: 36-38
    Article in Thieme ConnectPubMedGoogle Scholar
  • 5 Zhou T, Zhang X, Zhang S, Liu S, Xuan L. New phenylpropanoids and in vitro α-glucosidase inhibitors from Balanophora japonica . Planta Med 2011; 77: 477-481
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Yuan T, Ding Y, Wan C, Li L, Xu J, Liu K, Slitt A, Ferreira D, Khan IA, Seeram NP. Antidiabetic ellagitannins from pomegranate flowers: inhibition of α-glucosidase and lipogenic gene expression. Org Lett 2012; 14: 5358-5361
    CrossrefPubMedGoogle Scholar
  • 7 Okuda T, Yoshida T, Hatano T, Ito H. Ellagitannins renewed the concept of tannins. In: Quideau S, editor Chemistry and biology of ellagitannins, an underestimated class of bioactive plant polyphenols. Singapore: World Scientific Publishing; 2009: 30
    CrossrefGoogle Scholar
  • 8 Chang WL, Lee SS. Norneolignan and phenols from Curculigo capitulate . Phytochemistry 1998; 49: 2133-2136
    CrossrefPubMedGoogle Scholar
  • 9 Hirai N, Okamoto M, Udagawa H, Yamamuro M, Kato M, Koshimizu K. Absolute configuration of dehydrodiconiferyl alcohol. Biosci Biotechnol Biochem 1994; 58: 1679-1684
    CrossrefPubMedGoogle Scholar
  • 10 Hudson CS. The significance of certain numerical relations in the sugar group. J Am Chem Soc 1909; 31: 66-86
    CrossrefPubMedGoogle Scholar
  • 11 Liao SG, Yuan T, Zhang C, Yang SP, Wu Y, Yue JM. Cinnacassides A–E, five geranylphenylacetate glycosides from Cinnamomum cassia . Tetrahedron 2009; 65: 883-887
    CrossrefPubMedGoogle Scholar
  • 12 Khanbabaee K, Lötzerich K, Borges M, Grober M. The first total syntheses of enantiomerically pure naturally occuring ellagitannins gemin D and its regioisomer hippomanin A. J Prakt Chem 1999; 341: 159-166
    CrossrefPubMedGoogle Scholar
  • 13 Nonaka GI, Nishioka I. Tannins and related compounds. X. Rhubarb (2): isolation and structures of a glycerol gallate, gallic acid glucoside gallates, galloylglucoses and isolindleyin. Chem Pharm Bull 1983; 31: 1652-1658
    CrossrefPubMedGoogle Scholar
  • 14 Nawwar MA, Hussein SAM. Gall polyphenolics of Tamarix aphylla . Phytochemistry 1994; 36: 1035-1037
    CrossrefPubMedGoogle Scholar
  • 15 Wilkins C. Galloyl glucose derivatives from Heuchera cylindrical . Phytochemistry 1988; 27: 2317-2318
    CrossrefPubMedGoogle Scholar
  • 16 Tanaka T, Nonaka GI, Nishioka I. Tannins and related compounds. XVI. Isolation and characterization of six methyl glucoside gallates and a gallic acid glucoside gallate from Sanguisorba officinalis L. Chem Pharm Bull 1984; 32: 117-121
    CrossrefPubMedGoogle Scholar
  • 17 Yoshida T, Itoh H, Matsunaga S, Tanaka R, Okuda T. Tannins and related polyphenols of euphorbiaceous plants. IX. Hydrolyzable tannins with 1C4 glucose core form Phyllanthus flexuosus MUELL. ARG. Chem Pharm Bull 1992; 40: 53-60
    CrossrefPubMedGoogle Scholar
  • 18 Yoshikawa K, Eiko K, Mimura N, Kondo Y, Arihara S. Hovetrichosides C−G, five new glycosides of two auronols, two neolignans, and a phenylpropanoid from the bark of Hovenia trichocarea . J Nat Prod 1998; 61: 786-790
    CrossrefPubMedGoogle Scholar
  • 19 Lu Y, Foo LY. Identification and quantification of major polyphenols in apple pomace. Food Chem 1997; 59: 187-194
    CrossrefPubMedGoogle Scholar