Skip to main content
Log in

Isolation of five proanthocyanidins from pear (Pyrus pyrifolia Nakai) fruit peels

  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

Five proanthocyanidins, two B-type dimers and three A-type trimers, were purified and isolated from the fruit peels of Pyrus pyrifolia Nakai cv. Chuhwangbae. The isolated compounds were identified as (–)-epicatechin gallate-(4β → 8)-(–)-epicatechin (Hahashi et al. in Ann Biol Res 3:3200–3207, 2012), (–)-epicatechin-(4β → 8)-(–)-epicatechin (procyanidin B2) (Tanrioven and Eksi in Food Chem 93:89–93, 2005), (–)-epicatechin-(4β → 8, 2β → O-7)-(–)-epicatechin-(4β → 8)-(–)-epicatechin (cinnamtannins B1) (Salta et al. in J. Fun. Food 2: 153–157, 2010), (–)-epicatechin-(4β → 8)-(–)-epicatechin-(4β → 8, 2β → O-7)-(–)-epicatechin (aesculitannin A) (Challice and Westwood in Phytochemistry 11: 37–44, 1972), and (–)-epicatechin-(4β → 6)-(–)-epicatechin-(4β → 8, 2β → O→7)-(–)-epicatechin (Es-Safi et al. in J Agric Food Chem 54: 6969–6977, 2006). Their structures were determined by nuclear magnetic resonance and mass spectrometry. The three A-type proanthocyanidin trimers were identified for the first time from pear.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+
from $39.99 /Month
  • Starting from 10 chapters or articles per month
  • Access and download chapters and articles from more than 300k books and 2,500 journals
  • Cancel anytime
View plans

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Hahashi AA, Dashti S, Abdollahi H, Kermani MJ. Comparing vacuum agroinoculation in two pear (Pyrus communis L.) cultivars “Bartlett” and “Harrow Delight”. Ann. Biol. Res. 3: 3200–3207 (2012).

    Google Scholar 

  2. Tanrioven D, Eksi A. Phenolic compounds in pear juice from different cultivars. Food Chem. 93: 89–93 (2005).

    Article  Google Scholar 

  3. Salta J, Martins A, Santos RS, Neng NR, Nogueira JMF, Justino J, Rauter AP. Phenolics composition and antioxidant activity of Rocha pear and other pear cultivars-A comparative study. J. Fun. Food 2: 153–157 (2010).

    Article  CAS  Google Scholar 

  4. Challice JS, Westwood MN. Phenolic compounds of the genus Pyrus. Phytochemistry 11: 37–44 (1972).

    Article  CAS  Google Scholar 

  5. Es-Safi NE, Guyot S, Ducrot PH. NMR, ESI/MS, and MALDITOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity. J. Agr. Food Chem. 54: 6969–6977 (2006).

    Article  CAS  Google Scholar 

  6. Hamauze Y, Forest F, Hiramatsu K, Sugimoto M. Effect of pear (Pyrus communis L.) procyanidins on gastric lesions induced by HCl/ethanol in rats. Food Chem. 100: 255–263 (2007).

    Article  Google Scholar 

  7. Bilia AR, Gonzalez JG, Morelli I, Nieri E, Rubio ME. Flavonol glycosides from Pyrus bourgaeana. Phytochemistry 35: 1378–1380 (1994).

    Article  CAS  Google Scholar 

  8. Challice JS, Williams AH. Phenolic compounds of the genus Pyrus-I: The occurrence of flavones and phenolic acid derivatives of 3,4-dihydroxybenzyl alcohol 4-glucoside in Pyrus calleryana. Phytochemistry 7: 119–130 (1968).

    Article  CAS  Google Scholar 

  9. Lin LZ, Harnly JM. Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.). J. Agr. Food Chem. 56: 9094–9101 (2008).

    Article  CAS  Google Scholar 

  10. Iketani H, Manabe T, Matsuta N, Akihama T, and Hayashi T. Incongruence between RFLPs of chloroplast DNA and morphological classification in east Asian pear (Pyrus spp.). Genetic Res. Crop Evol. 45: 533–539 (1998).

    Article  Google Scholar 

  11. Li X, Zhang JY, Gao WY, Wang Y, Wang HY, Cao JG, Huang LQ. Chemical composition and anti-inflammatory and antioxidant activities of eight pear cultivars. J. Agric. Food Chem. 60: 8737–8744 (2012).

    Google Scholar 

  12. Li X, Zhang J, Gao W, Wang H. Study on chemical composition, anti-inflammatory and anti-microbial activities of extracts from Chinese pear fruit (Pyrus bretschneideri Rehd.). Food Chem. Toxicol. 50: 3673–3679 (2012).

    Article  CAS  Google Scholar 

  13. Lee KH, Cho JY, Lee HJ, Park KY, Ma YK, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Isolation and identification of phenolic compounds from an Asian pear (Pyrus pyrifolia Nakai) fruit peel. Food Sci. Biotechnol. 20: 1539–1545 (2011).

    Article  CAS  Google Scholar 

  14. Cho JY, Lee YG, Lee SH, Kim WS Park DK, Moon JH. An ether and three ester derivatives of phenylpropanoid from pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit and their radical-scavenging activity. Food Sci. Biotechnol. 23: 253–259 (2014).

    Article  CAS  Google Scholar 

  15. Lee YG, Cho JY, Kim CM, Jeong HY, Lee DI, Kim SR, Lee SH, Kim WS, Park KH, Moon JH. Isolation and identification of 3 low-molecular compounds from pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit peel. Korean J. Food Sci. Technol. 45: 174–179 (2013).

    Google Scholar 

  16. Lee KH, Cho JY, Lee HJ, Ma YK, Kwon J, Park SH, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Hydroxycinnamoylmalic acids and their methyl esters from pear (Pyrus pyrifolia Nakai) fruit peel. J. Agric. Food. Chem. 59: 10124–10128 (2011).

    Article  CAS  Google Scholar 

  17. Lee YG, Cho JY, Kim CM, Lee SH, Kim WS, Jeon TL, Park KH, Moon JH. Coumaroyl quinic acid derivatives and flavonoids from immature pear (Pyrus pyrifolia Nakai) fruit. Food Sci. Biotechnol. 22: 803–810 (2013).

    Article  CAS  Google Scholar 

  18. Cho JY, Kim CM, Lee HJ, Lee SH, Cho JA, Kim WS, Park KH, Moon JH. Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma. J. Agric. Food Chem. 61: 4563–4569 (2013).

    Article  CAS  Google Scholar 

  19. Lee YG, Cho JY, Lee HJ, Lee YH, Lee SH, Han TH, Kim WS, Park KH, Moon JH. Isolation and identification of a sterol and three glucosides from peel of pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit peel. Korean J. Food Sci. Technol. 45: 557–564 (2013).

    Article  Google Scholar 

  20. Mohri Y, Sagehashi M, Yamado T, Hattori Y, Morimura K, Hamauzu Y, Kamo T, Hirota M, Makabe H. An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate. Heterocycles 79: 549–563 (2009).

    Article  CAS  Google Scholar 

  21. Zhang YB, Choi HJ, Han HS, Park JH, Son JH, Bae JH, Seung TS, An BJ, Kim HG, Choi C. Chemical structure of polyphenol isolated from Korean pear (Pyrus pyrifolia Nakai). Korean J. Food Sci. Technol. 35: 959–967 (2003).

    Google Scholar 

  22. Saito A, Mizushina Y, Ikawa H, Yosida H, Doi Y, Tanaka A, Nakajima N. Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases. Bioorg. Med. Chem. 13: 2759–2771 (2005).

    Article  CAS  Google Scholar 

  23. Khan ML, Haslam E, Williamson MP. Structure and conformation of the procyanidin B-2 dimer. Mag. Res. Chem. 35:854–858 (1997).

    Article  CAS  Google Scholar 

  24. Baldé A, Bruyne TD, Pieters L, Claeys M, Berghe DV, Vlietinck A, Wray V, Kolodziej H. Proanthocyanidins from stem bark of Pavetta owariensis, 3. Nmr study of acetylated trimeric proanthocyanidins possessing a doubly-linked structure. J. Nat. Prod. 56 (7): 1078–1088 (1993).

    Article  Google Scholar 

  25. Idowe TO, Ogundaini AO, Salau AO, Obuotor EM, Bezabih M, Abegaz M. Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry 71: 2092–2098 (1993).

    Article  Google Scholar 

  26. Morimoto S, Nonaka G, Nishioka I. Tannins and related compounds. LIX. Aesculitannins, novel proanthocyanidins with doubly-bonded structures from Aesculus hippocastanum L. Chem. Pharm. Bull. 35 (12): 4717–4729 (1987).

    Article  CAS  Google Scholar 

  27. Foo LY, Lu Y, Howell AB, Vorsa N. A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli. J. Nat. Prod. 63 (9): 1225–1228 (2000).

    Article  CAS  Google Scholar 

  28. Prior RL, Gu L. Occurrrence and biological significance of proanthocyanidins in the American diet. Phytochemistry 66: 2264–2280 (2005).

    Article  CAS  Google Scholar 

  29. Hamauzu Y, Sakai I. Change in polyphenolic compounds and antioxidant functions in ‘Bartlett’ pear fruit during storage and postharvest ripening. Food Preserv. Sci. 28: 25–32 (2002).

    Article  Google Scholar 

  30. Yobota K, Kimura H, Ogavwa S, Akihiro T. Analysis of A-type and B-type highly polymeric proantocyanidins and their biological activities as nutraceuticals. J. Chem. (2013). doi:10.1155/2013/352042.

    Google Scholar 

  31. Smeriglio A, Barreca D, Bellocco E, Trombetta D. Proanthocyanidins and hydrolysable tannins: occurrence, dietary intake and pharmacological effects. Br. J. Pharmacol. (2016).

  32. Howell AB, Reed JD, Krueger CG, Winterbottom R, Cunningham G, Leahy M. A-type cranberry proanthocyanidins and uropathogenic bacterial anti-adhesion activity. Phytochemistry 66: 2281–2291 (2005).

    Article  CAS  Google Scholar 

  33. Neto CC. Cranberry and its phytochemicals: a review of in vitro anticancer studies. J. Nutr. 137: 186s–193s (2007).

    CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the Korea Institute of Planning and Evaluation for Technology in Food, Agriculture, Forestry and Fisheries (iPET) through the High Value-Added Food Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) (Grant No. 315069-3). HR-ESI–MS and NMR spectral data were obtained from the Korea Basic Science Institute, Ochang and Gwan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jae-Hak Moon.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jeong, D.E., Cho, JY., Lee, Y.G. et al. Isolation of five proanthocyanidins from pear (Pyrus pyrifolia Nakai) fruit peels. Food Sci Biotechnol 26, 1209–1215 (2017). https://doi.org/10.1007/s10068-017-0157-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-017-0157-4

Keywords