New gallotannin and other phytochemicals from sycamore maple (Acer pseudoplatanus) leaves

Natural Product Communications

Volumn 10, Issue 11, 2015, Pages 1977-1980

  Zhang, Lu ^a,b   Tu, Zong Cai ^b   Yuan, Tao ^a,c   Ma, Hang ^a   Niesen, Daniel B ^a   Wang, Hui ^b   Seeram, Navindra P ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

^b NANCHANG UNIVERSITY   (China)

^c XINJIANG TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Acer pseudoplatanus; Antioxidant; Gallotannins; Sycamore maple; Glucosidase

Indexed keywords

1,2,3 TRI O GALLOYL 6 O (PARA HYDROXYBENZOYL) BETA DEXTRO GLUCOPYRANOSIDE; 1,2,3,6 TETRA O GALLOYL BETA DEXTRO GLUCOPYRANOSIDE; 1,2,4,6 TETRA O GALLOYL BETA DEXTRO GLUCOPYRANOSIDE; 1,2,6 TRI O GALLOYL BETA DEXTRO GLUCOPYRANOSIDE; 3 FERULOYLQUINIC ACID; 4 FERULOYLQUINIC ACID; 5 COUMAROYLQUINIC ACID; 5 FERULOYLQUINIC ACID; CHLOROGENIC ACID; ELLAGIC ACID; GALLOCATECHIN; KAEMPFEROL 3 O ALPHA LEVO ARABINOFURANOSIDE; KAEMPFEROL 3 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O BETA LEVO ARABINOPYRANOSIDE; MACATANNIN B; METHYL 5 PARA COUMAROYLQUINIC ACID; NATURAL PRODUCT; NEOCHLOROGENIC ACID; PARA COUMARIC ACID; QUERCETIN; QUERCETIN 3 O (2'' O GALLOYL) ALPHA LEVO RHAMNOPYRANOSIDE; QUERCETIN 3 O (2'',6'' O GALLOYL) BETA DEXTRO GLUCOPYRANOSIDE; QUERCETIN 3 O ALPHA LEVO ARABINOFURANOSIDE; QUERCETIN 3 O ALPHA LEVO RHAMNOPYRANOSIDE; QUERCETIN 3 O BETA (2'' O GALLOYL BETA LEVO ARABINOFURANOSIDE); QUERCETIN 3 O BETA DEXTRO GLUCOPYRANOSIDE; QUERCETIN 3 O BETA LEVO ARABINOPYRANOSIDE; QUERCETIN 7 ALPHA LEVO RHAMNOPYRANOSIDE; TANNIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; GLYCOSIDASE INHIBITOR; PLANT EXTRACT; PLANT MEDICINAL PRODUCT;

ACER; ACER PSEUDOPLATANUS; ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; HETERONUCLEAR MULTIPLE BOND CORRELATION; MASS SPECTROMETRY; NONHUMAN; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; ISOLATION AND PURIFICATION;

ACER; GLYCOSIDE HYDROLASE INHIBITORS; HYDROLYZABLE TANNINS; MOLECULAR STRUCTURE; PHYTOCHEMICALS; PLANT EXTRACTS; PLANT LEAVES;

EID: 84955154897     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1501001143     Document Type: Article

References (32)

1. Zhang J, Li L, Kim S-H, Hagerman AE, Lü J. (2009) Anti-cancer, anti-diabetic and other pharmacologic and biological activities of penta-galloylglucose. Pharmaceutical Research, 26, 2066-2080.
2. Haddock EA, Gupta RK, Al-Shafi SM, Haslam E, Magnolato D. (1982) The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part1. Introduction. Naturally occurring galloyl esters. Journal of the Chemical Society, Perkin Transactions 1, 2515-2524.
3. Hatano T, Hattori S, Ikeda Y, Shingu T, Okuda T. (1990) Gallotannins having a 1, 5-anhydro-D-glucitol core and some ellagitannins from Acer species. Chemical and Pharmaceutical Bulletin, 38, 1902-1905.
4. Wan C, Yuan T, Li L, Kandhi V, Cech NB, Xie M, Seeram NP. (2012) Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems. Bioorganic & Medicinal Chemistry Letters, 22, 597-600.
5. Honma A, Koyama T, Yazawa K. (2011) Anti-hyperglycaemic effects of the Japanese red maple Acer pycnanthum and its constituents the ginnalins B and C. Journal of Enzyme Inhibition and Medicinal Chemistry, 26, 176-180.
6. Liu W, Ouyang Y, Wan C-P. (2013) Flavonoids of the genus of Acer: A mini review. Asian Journal of Chemistry, 25, 7075-7078.
7. Yuan T, Ding Y, Wan C, Li L, Xu J, Liu K, Slitt A, Ferreira D, Khan IA, Seeram NP. (2012) Antidiabetic ellagitannins from pomegranate flowers: inhibition of α-glucosidase and lipogenic gene expression. Organic Letters, 14, 5358-5361.
8. Duan D, Li Z, Luo H, Zhang W, Chen L, Xu X. (2004) Antiviral compounds from traditional Chinese medicines Galla chinese as inhibitors of HCV NS3 protease. Bioorganic & Medicinal Chemistry Letters, 14, 6041-6044.
9. Roselli M, Lentini G, Habtemariam S. (2012) Phytochemical, antioxidant and anti-α-glucosidase activity evaluations of Bergenia cordifolia. Phytotherapy Research, 26, 908-914.
10. Gunawan-Puteri MD, Kato E, Kawabata J. (2012) α-Amylase inhibitors from an Indonesian medicinal herb, Phyllanthus urinaria. Journal of the Science of Food and Agriculture, 92, 606-609.
11. Wu Q, Qi J, Li M, Xu M, Liu L. (2012) Chemical constituents of Erodium stephanianum Willd. [J]. Acta Chinese Medicine and Pharmacology, 1, 31-34.
12. Lei W, Ling F, Lin J, You A, Lu J. (2012) Studies of chemical constituents from Rosa chinensis Jacq. Chemical Journal of Chinese Universities, 11, 16-19.
13. Zhao HX, Bai H, Li W, Wang YS, Liu YJ, Liu AQ. (2011) Chemical constituents from Polygonum capitatum. Natural Product Research Development 23, 262-266.
14. Rösch D, Krumbein A, Kroh LW. (2004) Antioxidant gallocatechins, dimeric and trimeric proanthocyanidins from sea buckthorn (Hippophae rhamnoides) pomace. European Food Research and Technology, 219, 605-613.
15. Wang H, Du Y-J, Song H-C. (2010) α-Glucosidase and α-amylase inhibitory activities of guava leaves. Food Chemistry, 123, 6-13.
16. Wang N, Zhu B, Sheng H, Chen Y, Yang Y. (2011) Studies on chemical constituents of Rumex nepalensis J. Chinese Journal of Experimental Traditional Medical Formulae, 19, 41-45.
17. Cheng K-W, Yang R-Y, Tsou SC, Lo CS, Ho C-T, Lee T-C, Wang M. (2009) Analysis of antioxidant activity and antioxidant constituents of Chinese toon. Journal of Functional Foods, 1, 253-259.
18. Xie Y, Zhang H, Liu T, Wen C, Guo L. (2014) Chemical constituents from Pouzolzia zeylanica (L.) Benn. var. microphylla (Wedd.) WT Wang. Chinese Journal of Experimental Traditional Medical Formulae, 20, 43-47.
19. Islam MS, Yoshimoto M, Yahara S, Okuno S, Ishiguro K, Yamakawa O. (2002) Identification and characterization of foliar polyphenolic composition in sweetpotato (Ipomoea batatas L.) genotypes. Journal of Agricultural and Food Chemistry, 50, 3718-3722.
20. Wan C, Yuan T, Cirello AL, Seeram NP. (2012) Antioxidant and α-glucosidase inhibitory phenolics isolated from highbush blueberry flowers. Food Chemistry, 135, 1929-1937.
21. Pauli G, Poetsch F, Nahrstedt A. (1998) Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques. Phytochemical Analysis, 9, 177-185.
22. Li S, Chen R, Yu D. (2007) Study on chemical constituents of Myricaria paniculata I. China Journal of Chinese Materia Medica, 32, 403-406.
23. Zhou C, Liu C, Huang X, Wu J, Li L, Li D, Song S. (2013) Isolation and identification of aromatic compounds from leaves of Crataegus pinnatifida Bge. Chinese Journal of Medicinal Chemistry, 23, 213-217.
24. Xu G. (2011) Chemical constituents from Paraixeris serotina Chinese Traditional and Herbal Drugs, 42, 1079-1082.
25. Jeon KS, Na H-J, Kim Y-M, Kwon HJ. (2005) Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume. Biochemical and Biophysical Research Communications, 330, 1268-1274.
26. Ma H, Yuan T, Gonzalez-Sarrias A, Li L, Edmonds ME, Seeram NP. (2012) New galloyl derivative from winged sumac (Rhus copallinum) fruit. Natural Product Communications, 7, 45-46.
27. Ding Y, Liang C, Nguyen HT, Choi EM, Kim JA, Kim YH. (2010) Chemical constituents from Acer mandshuricum and their effects on the function of osteoblastic MC3T3-E1 cells. Bulletin of Korean Chemical Society, 31, 929-932.
28. Pojchaijongdee N, Sotanaphun U, Limsirichaikul S, Poobrasert O. (2010) Geraniinic acid derivative from the leaves of Phyllanthus reticulatus. Pharmaceutical Biology, 48, 740-744.
29. Huang SX, Yang J, Xiao WL, Zhu YL, Li RT, Li LM, Pu JX, Li X, Li SH, Sun HD. (2006) Three novel terpenoids from Schisandra pubescens var. pubinervis. Helvetica Chimica Acta, 89, 1169-1175.
30. Zhang Z, Zhang W, Ji YP, Zhao Y, Wang CG, Hu JF. (2010). Gynostemosides A-E, megastigmane glycosides from Gynostemma pentaphyllum. Phytochemistry, 71, 693-700.
31. Li L, Seeram NP. (2010) Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds. Journal of Agricultural and Food Chemistry, 58, 11673-11679.
32. Ma H, Liu W, Frost L, Wang L, Kong L, Dain JA, Seeram NP. (2015) The hydrolyzable gallotannin, penta-O-galloyl-β-d-glucopyranoside, inhibits the formation of advanced glycation endproducts by protecting protein structure. Molecular BioSystems, 11, 1338-1347.