Preparative isolation and purification of five flavonoid glycosides and one benzophenone galloyl glycoside from psidium guajava by high-Speed counter-current chromatography (HSCCC)

Molecules

Volumn 18, Issue 12, 2013, Pages 15648-15661

  Zhu, Yindi ^a   Liu, Yue ^b   Zhan, Ying ^a   Liu, Lin ^a   Xu, Yajuan ^b   Xu, Tunhai ^a   Liu, Tonghua ^a  

^a BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

^b Jilin Academy of Chinese Medicine Sciences   (China)

Author keywords

Benzophenone galloyl glycoside; Flavonoid glycosides; HSCCC; Psidium guajava

Indexed keywords

BENZOPHENONE; BENZOPHENONE DERIVATIVE; FLAVONOID; GLYCOSIDE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COUNTER CURRENT CHROMATOGRAPHY; ISOLATION AND PURIFICATION; PSIDIUM;

BENZOPHENONES; COUNTERCURRENT DISTRIBUTION; FLAVONOIDS; GLYCOSIDES; MOLECULAR STRUCTURE; PSIDIUM; SOLVENTS;

EID: 84890965356     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181215648     Document Type: Article

References (34)

1. Gutierrez, R.M.; Mitchell, S.; Solis, R.V. Psidium guajava: A review of its traditional uses, phytochemistry and pharmacology. J. Ethnopharmacol. 2008, 117, 1-27.
2. Juarez-Vazquez Mdel, C.; Carranza-Alvarez, C.; Alonso-Castro, A.J.; Gonzalez-Alcaraz, V.F.; Bravo-Acevedo, E.; Chamarro-Tinajero, F.J.; Solano, E. Ethnobotany of medicinal plants used in Xalpatlahuac, Guerrero, Mexico. J. Ethnopharmacol. 2013, 148, 521-527.
3. McCook-Russell, K.P.; Nair, M.G.; Facey, P.C.; Bowen-Forbes, C.S. Nutritional and nutraceutical comparison of Jamaican Psidium cattleianum (strawberry guava) and Psidium guajava (common guava) fruits. Food Chem. 2012, 134, 1069-1073.
4. Lin, C.Y.; Yin, M.C. Renal protective effects of extracts from guava fruit (Psidium guajava L.) in diabetic mice. Plant Foods Hum. Nutr. 2012, 67, 303-308.
5. Owen, P.L.; Martineau, L.C.; Caves, D.; Haddad, P.S.; Matainaho, T.; Johns, T. Consumption of guava (Psidium guajava L.) and noni (Morinda citrifolia L.) may protect betel quid-chewing Papua New Guineans against diabetes. Asia Pac. J. Clin. Nutr. 2008, 17, 635-643.
6. Ojewole, J.A.; Awe, E.O.; Chiwororo, W.D. Antidiarrhoeal activity of Psidium guajava Linn. (Myrtaceae) leaf aqueous extract in rodents. J. Smooth Muscle Res. 2008, 44, 195-207.
7. Cheng, F.C.; Shen, S.C.; Wu, J.S. Effect of guava (Psidium guajava L.) leaf extract on glucose uptake in rat hepatocytes. J. Food Sci. 2009, 74, H132-H138.
8. Shen, S.C.; Cheng, F.C.; Wu, N.J. Effect of guava (Psidium guajava L.) leaf soluble solids on glucose metabolism in type 2 diabetic rats. Phytother. Res. 2008, 22, 1458-1464.
9. Soman, S.; Rauf, A.A.; Indira, M.; Rajamanickam, C. Antioxidant and antiglycative potential of ethyl acetate fraction of Psidium guajava leaf extract in streptozotocin-induced diabetic rats. Plant Foods Hum. Nutr. 2010, 65, 386-391.
10. Shabana, S.; Kawai, A.; Kai, K.; Akiyama, K.; Hayashi, H. Inhibitory activity against urease of quercetin glycosides isolated from Allium cepa and Psidium guajava. Biosci. Biotechnol. Biochem. 2010, 74, 878-880.
11. Choi, J.H.; Park, B.H.; Kim, H.G.; Hwang, Y.P.; Han, E.H.; Jin, S.W.; Seo, J.K.; Chung, Y.C.; Jeong, H.G. Inhibitory effect of Psidium guajava water extract in the development of 2,4-dinitrochlorobenzene-induced atopic dermatitis in NC/Nga mice. Food Chem. Toxicol. 2012, 50, 2923-2929.
12. Chen, K.C.; Hsieh, C.L.; Huang, K.D.; Ker, Y.B.; Chyau, C.C.; Peng, R.Y. Anticancer activity of rhamnoallosan against DU-145 cells is kinetically complementary to coexisting Polyphenolics in Psidium guajava budding leaves. J. Agric. Food Chem. 2009, 57, 6114-6122.
13. Livingston Raja, N.R.; Sundar, K. Psidium guajava Linn confers gastro protective effects on rats. Eur. Rev. Med. Pharmacol. Sci. 2012, 16, 151-156.
14. Rattanachaikunsopon, P.; Phumkhachorn, P. Bacteriostatic effect of flavonoids isolated from leaves of Psidium guajava on fish pathogens. Fitoterapia 2007, 78, 434-436.
15. Shu, J.C.; Chou, G.X.; Wang, Z.T. One new galloyl glycoside from fresh leaves of Psidium guajava L. Acta Pharm. Sin. 2010, 45, 334-337.
16. Shu, J.C.; Chou, G.X.; Wang, Z.T. One new diphenylmethane glycoside from the leaves of Psidium guajava L. Nat. Prod. Res. 2012, 26, 1971-1975.
17. Shao, M.; Wang, Y.; Jian, Y.Q.; Huang, X.J.; Zhang, D.M.; Tang, Q.F.; Jiang, R.W.; Sun, X.G.; Lv, Z.P.; Zhang, X.Q.; et al. Guadial A and psiguadials C and D, three unusual meroterpenoids from Psidium guajava. Org. Lett. 2012, 14, 5262-5265.
18. Gao, Y.; Wang, G.Q.; Wei, K.; Hai, P.; Wang, F.; Liu, J.K. Isolation and biomimetic synthesis of (+/-)-guajadial B, a novel meroterpenoid from Psidium guajava. Org. Lett. 2012, 14, 5936-5939.
19. Begum, S.; Hassan, S.I.; Ali, S.N.; Siddiqui, B.S. Chemical constituents from the leaves of Psidium guajava. Nat. Prod. Res. 2004, 18, 135-140.
20. Eidenberger, T.; Selg, M.; Krennhuber, K. Inhibition of dipeptidyl peptidase activity by flavonol glycosides of guava (Psidium guajava L.): A key to the beneficial effects of guava in type II diabetes mellitus. Fitoterapia 2013, 89, 74-79.
21. Yang, L.; Li, X.F.; Gao, L.; Zhang, Y.O.; Cai, G.P. Suppressive effects of quercetin-3-O-(6″-Feruloyl)-beta-D-galactopyranoside on adipogenesis in 3T3-L1 preadipocytes through down-regulation of PPARgamma and C/EBPalpha expression. Phytother. Res. 2012, 26, 438-444.
22. Liu, R.L.; Xiong, Q.J.; Shu, Q.; Wu, W.N.; Cheng, J.; Fu, H.; Wang, F.; Chen, J.G.; Hu, Z.L. Hyperoside protects cortical neurons from oxygen-glucose deprivation-reperfusion induced injury via nitric oxide signal pathway. Brain Res. 2012, 1469, 164-173.
23. Fujii, Y.; Kimura, M.; Ishii, Y.; Yamamoto, R.; Morita, R.; Hayashi, S.M.; Suzuki, K.; Shibutani, M. Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats. Toxicology 2013, 305, 30-40.
24. Schmidt, J.S.; Lauridsen, M.B.; Dragsted, L.O.; Nielsen, J.; Staerk, D. Development of a bioassay-coupled HPLC-SPE-ttNMR platform for identification of alpha-glucosidase inhibitors in apple peel (Malus xdomestica Borkh.). Food Chem. 2012, 135, 1692-1699.
25. Metwally, A.M.; Omar, A.A.; Harraz, F.M.; El Sohafy, S.M. Phytochemical investigation and antimicrobial activity of Psidium guajava L. leaves. Pharmacogn. Mag. 2010, 6, 212-218.
26. Matsuzaki, K.; Ishii, R.; Kobiyama, K.; Kitanaka, S. New benzophenone and quercetin galloyl glycosides from Psidium guajava L. J. Nat. Med. 2010, 64, 252-256.
27. Ito, Y. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J. Chromatogr. A 2005, 1065, 145-168.
28. Han, L.; Ji, L.; Boakye-Yiadom, M.; Li, W.; Song, X.; Gao, X. Preparative isolation and purification of four compounds from Cistanches deserticola Y.C. Ma by high-speed counter-current chromatography. Molecules 2012, 17, 8276-8284.
29. Faure, K.; Bouju, E.; Suchet, P.; Berthod, A. Use of limonene in countercurrent chromatography: A green alkane substitute. Anal. Chem. 2013, 85, 4644-4650.
30. Du, Q.; Jiang, Z.; Wang, D. Excellent combination of counter-current chromatography and preparative high-performance liquid chromatography to separate galactolipids from pumpkin. J. Chromatogr. A 2009, 1216, 4176-4180.
31. Cao, X.L. HSCCC Technology and Application; Chemical Industry Press: Beijing, China, 2005; pp. 71-78.
32. Lee, S.Y.; Kim, K.H.; Lee, I.K.; Lee, K.H.; Choi, S.U.; Lee, K.R. A new flavonol glycoside from Hylomecon vernalis. Arch. Pharm. Res. 2012, 35, 415-421.
33. Nguelefack, T.B.; Mbakam, F.H.; Tapondjou, L.A.; Watcho, P.; Nguelefack-Mbuyo, E.P.; Ponou, B.K.; Kamanyi, A.; Park, H.J. A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis. Arch. Pharm. Res. 2011, 34, 543-550.
34. Camargo, L.M.D.M.; Férézoub, J.-P.; Tinoco, L.W.; Kaiser, C.R.; Costa, S.S. Flavonoids from Mimosa xanthocentra (Leguminosae: Mimosoideae) and molecular modeling studies for isovitexin-2″-O-a-L-rhamnopyranoside rotamers. Phytochem. Lett. 2012, 5, 427-431.