Isolation and identification of antioxidant and α-glucosidase inhibitory compounds from fruit juice of Nitraria tangutorum

Food Chemistry

Volumn 227, Issue , 2017, Pages 93-101

  Zhao, Jian Qiang ^a   Wang, Yan Ming ^b   Yang, Yan Long ^c   Zeng, Ying ^c   Wang, Qi Lan ^a   Shao, Yun ^a   Mei, Li Juan ^a   Shi, Yan Ping ^b   Tao, Yan Duo ^a  

^a NORTHWEST INSTITUTE OF PLATEAU BIOLOGY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^c KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Antioxidants; Glucose derived carbolines; Nitraria tangutorum; Glucosidase inhibitory

Indexed keywords

AGENTS; AMINO ACIDS; FRUIT JUICES; FRUITS; GLUCOSE; PYRIDINE; SPECTROSCOPIC ANALYSIS;

ANTI-OXIDANT ACTIVITIES; CARBOLINES; GLUCOSIDASE; INHIBITORY ACTIVITY; INHIBITORY COMPOUNDS; ISOLATION AND IDENTIFICATION; NITRARIA TANGUTORUM; QINGHAI TIBET PLATEAU;

ANTIOXIDANTS;

7 O BETA GLUCOSYL 4 (2 METHOXY 2 OXOETHYL)HEPTA 3,5 DIENOIC ACID; ACARBOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; ANTIOXIDANT; BETA CARBOLINE DERIVATIVE; NATURAL PRODUCT; TANGUTORID A; TANGUTORID B; TANGUTORID C; TANGUTORID D; TANGUTORID E; TANGUTORID F; TRYPTOPHAN; UNCLASSIFIED DRUG; GLYCOSIDASE INHIBITOR; PLANT EXTRACT;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL COMPOSITION; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; FRUIT JUICE; MEDICINAL PLANT; NITRARIA TANGUTORUM; NONHUMAN; PICTET SPENGLER REACTION; ANALYSIS; ANGIOSPERM; CHEMISTRY; FRUIT; FRUIT AND VEGETABLE JUICE; ISOLATION AND PURIFICATION; TIBET;

ALPHA-GLUCOSIDASES; ANGIOSPERMS; ANTIOXIDANTS; FRUIT; FRUIT AND VEGETABLE JUICES; GLYCOSIDE HYDROLASE INHIBITORS; PLANT EXTRACTS; TIBET;

EID: 85010400054     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2017.01.031     Document Type: Article

References (41)

1. Adachi, J., Mizoi, Y., Naito, T., Ogawa, Y., Uetani, Y., Ninomiya, I., Identification of tetrahydro-β-carboline-3-carboxylic acid in foodstuffs, human urine and human milk. JN The Journal of Nutrition 121 (1991), 646–652.
2. Di Giorgio, C., Delmas, F., Ollivier, E., Elias, R., Balansard, G., Timon-David, P., In vitro activity of the β-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. Experimental Parasitology 106 (2004), 67–74.
3. Diem, S., Bergmann, J., Herderich, M., Tryptophan-N-glucoside in fruits and fruit juices. Journal of Agricultural and Food Chemistry 48 (2000), 4913–4917.
4. Diem, S., Herderich, M., Reaction of tryptophan with carbohydrates: Identification and quantitative determination of novel β-carboline alkaloids in food. Journal of Agricultural and Food Chemistry 49 (2001), 2486–2492.
5. Du, X.P., Xin, H.L., Peng, C., Pharmacology and phytochemistry of the Nitraria genus. Molecular Medicine Reports 11 (2015), 11–20.
6. Duan, J.A., Williams, I.D., Chen, C.T., Tangutorine: A novel β-carboline alkaloid from Nitraria tangutorum. Tetrahedron Letters 40 (1999), 2593–2596.
7. Gao, D.F., Xu, M., Yang, C.R., Xu, M., Zhang, Y.J., Phenolic antioxidants from the leaves of Camellia pachyandra Hu. Journal of Agricultural and Food Chemistry 58 (2010), 8820–8824.
8. Georgopoulou, C., Aligiannis, N., Fokialakis, N., Mitaku, S., Acretoside, a new sucrose ester from Aristolochia cretica. Journal of Asian Natural Products Research 7 (2005), 799–803.
9. Goda, Y., Hoshino, K., Akiyama, H., Ishikawa, T., Abe, Y., Nakamura, T.,. Toyoda, M., Constituents in watercress: Inhibitors of histamine release from RBL-2H3 cells induced by antigen stimulation. Biological & Pharmaceutical Bulletin 22 (1999), 1319–1326.
10. Herraiz, T., Ethyl 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate: a novel β-carboline found in alcoholic beverages. Food Chemistry 66 (1999), 313–321.
11. Herraiz, T., Tetrahydro-β-carboline bioactive alkaloids in beverages and foods. Shahidi, F., Weerasinghe, D.K., (eds.) Nutraceutical beverages, 2004, American Chemical Society, Washington, DC, 405–426.
12. Herraiz, T., β-Carboline alkaloids. Gilbert, J., Senyuva, H.Z., (eds.) Bioactive compounds in foods, 2009, Blackwell Publishing Ltd, Oxford, 199–223.
13. Herraiz, T., Galisteo, J., Identification and occurrence of the novel alkaloid penthydroxypentyl-tetrahydro-β-carboline-3-carboxylic acid as a tryptophan glycoconjugate in fruit juices and jams. Journal of Agricultural and Food Chemistry 50 (2002), 4690–4695.
14. Herraiz, T., Galisteo, J., Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. Journal of Agricultural and Food Chemistry 51 (2003), 7156–7161.
15. Herraiz, T., Galisteo, J., Hydroxyl radical reactions and the radical scavenging activity of β-carboline alkaloids. Food Chemistry 172 (2015), 640–649.
16. Hu, N., Zheng, J., Li, W.C., Suo, Y.R., Isolation, stability, and antioxidant activity of anthocyanins from Lycium ruthenicum Murray and Nitraria tangutorum Bobr of qinghai-tibetan plateau. Separation and Purification Technology 49 (2014), 2897–2906.
17. Hu, Y.M., Ye, W.C., Li, Q., Tian, H.Y., Wang, H., Du, H.Y., C-glycosylflavones from Stellaria media. Chinese Journal of Natural Medicines 4 (2006), 420–424.
18. Jiao, W.H., Gao, H., Li, C.Y., Zhao, F., Jiang, R.W., Wang, Y.,. Yao, X.S., Quassidines A-D, bis-β-carboline alkaloids from the stems of Picrasma quassioides. Journal Natural Products 73 (2010), 167–171.
19. Kazuma, K., Noda, N., Suzuki, M., Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62 (2003), 229–237.
20. Kitajima, J., Ishikawa, T., Tanaka, Y., Ono, M., Ito, Y., Nohara, M., Water-soluble constituents of fennel. V. Glycosides of aromatic compounds. Chemical & Pharmaceutical Bulletin 46 (1998), 1587–1590.
21. Kusurkar, R.S., Goswami, S.K., Efficient one-pot synthesis of anti-HIV and anti-tumour β-carbolines. Tetrahedron 60 (2004), 5315–5318.
22. Landtag, J., Baumert, A., Degenkolb, T., Schmidt, J., Wray, V., Scheel, D.,. Rosahl, S., Accumulation of tyrosol glucoside in transgenic potato plants expressing a parsley tyrosine decarboxylase. Phytochemistry 60 (2002), 683–689.
23. 13C Nuclear magnetic resonance. Magnetic Resonance in Chemistry 30 (1992), 1035–1040.
24. Li, X.C., Cai, L., Wu, C.D., Antimicrobial compounds from Ceanothus americanus against oral pathogens. Phytochemistry 46 (1997), 97–102.
25. Liang, N., Xue, W., Kennepohl, P., Kitts, D.D., Interactions between major chlorogenic acid isomers and chemical changes in coffee brew that affect antioxidant activities. Food Chemistry 213 (2016), 251–259.
26. Lu, H.L., Ouyang, F., Su, Y.L., Ji, T.F., Liu, H., Study on chemical constituents of the fruits of Nitraria tangutorum Bobr. Northwest Pharmaceutical Journal 28 (2013), 221–223.
27. Nakatsuka, S.I., Feng, B.N., Goto, T., Kihara, K., Structures of flazin and YS, highly fluorescent compounds isolated from japanese soy sauce. Tetrahedron Letters 29 (1986), 3399–3402.
28. Papavergou, E., Herraiz, T., Identification and occurrence of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid: The main β-carboline alkaloid in smoked foods. Food Research International 36 (2003), 843–848.
29. Park, B.J., Tomohiko, M., Feruloyl, caffeoyl, and flavonol glucosides from Equisetum hyemale. Chemistry of Natural Compounds 47 (2011), 363–365.
30. Pedras, M.S.C., Smith, K.C., Taylor, J.L., Production of 2,5-dioxopiperazine by a new isolate type of the blackleg fungus Phoma lingam. Phytochemistry 49 (1998), 1575–1577.
31. Piacente, S., Carbone, V., Plaza, A., Zampelli, A., Pizza, C., Investigation of the tuber constituents of Maca (Lepidium meyenii Walp.). Journal of Agricultural and Food Chemistry 50 (2002), 5621–5625.
32. Röper, H., Röper, S., Heyns, K., N.m.r. spectroscopy of N-(1-deoxy-d-fructos-1-yl)-l-amino acids (“fructose-amino acids”). Carbohydrate Research 116 (1983), 159–183.
33. Sayed, H.M., Mohamed, M.H., Farag, S.F., Mohamed, G.A., Omobuwajo, O.R.M., Proksch, P., Fructose-amino acid conjugate and other constituents from Cyperus rotundus L. Natural Product Research 22 (2008), 1487–1497.
34. Sen, N.P., Seaman, S.W., Lau, B.P.-Y., Weber, D., Lewis, D., Determination and occurrence of various tetrahydro-β-carboline-3-carboxylic acids and the corresponding N-nitroso compounds in foods and alcoholic beverages. Food Chemistry 54 (1995), 327–337.
35. Suzuki, C., Hirano, K., Satoh, T., Miura, M., Direct synthesis of N-H carbazoles via iridium (III)-catalyzed intramolecular C-H amination. Organic Letters 17 (2015), 1597–1600.
36. Uda, Y., Ozawa, Y., Takayama, M., Suzuki, K., Maeda, Y., Free and soluble bound phenolic acids in some cruciferous vegetables. Journal of the Japanese Society for Food Science and Technology 35 (1998), 360–366.
37. Wu, Z.B., Yao, X.Y., Wang, W., Li, Y.T., Xu, Y.H., Chen, W., Flavonoids from Nitraria tangutorum. Chemistry of Natural Compounds 49 (2014), 1125–1126.
38. Yang, Y., Wei, X., Shi, R., Fan, Q., An, L., Salinity induced physiological modification in the callus from halophyte Nitraria tangutorum Bobr. Journal of Plant Growth Regulation 29 (2010), 465–476.
39. Yang, Y., Yang, F., Li, X., Shi, R., Lu, J., Signal regulation of proline metabolism in callus of the halophyte Nitraria tangutorum Bobr. grown under salinity stress. Plant Cell, Tissue and Organ Culture 112 (2013), 33–42.
40. Yilmazer-Musa, M., Griffith, A.M., Michels, A.J., Schneider, E., Frei, B., Grape seed and tea extracts and catechin 3-gallates are potent inhibitors of α-amylase and α-glucosidase activity. Journal of Agricultural and Food Chemistry 60 (2012), 8924–8929.
41. Zhao, M., Bi, L.R., Wang, W., Wang, C., Baudy-Floc'h, M., Ju, J.F., Peng, S.Q., Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates. Bioorganic & Medicinal Chemistry 14 (2006), 6998–7010.