Abstract
Four flavan-3-ols, (+)-catechin (1), (+)-catechin 7-O-β-D-apiofuranoside (2), (+)-catechin 7-O-β-D-xylopyranoside (3), (+)-catechin 7-O-β-D-glucopyranoside (4), and proanthocyanidin A-1 (5) as well as three other constituents, isolated from an EtOAc-soluble extract of the
stem barks of Ulmus davidiana var. japonica, were evaluated for inhibitory activity against the formation of AGEs. Compounds
1 – 5 exhibited a significant inhibitory activity on the formation of AGEs in an AGEs-BSA
assay by specific fluorescence and this was confirmed by an indirect AGEs-ELISA. Moreover,
compounds 1 and 5 markedly reduced AGEs-BSA cross-linking to collagen in a dose-dependent manner.
Abbreviations
AGEs:advanced glycation end products
BSA:bovine serum albumin
CC:column chromatography
CD:circular dichroism
Key words
Ulmus davidiana var. japonica
- Ulmaceae - flavan-3-ols - AGEs - AGEs-BSA cross-linking
References
- 1 Lee S J. Korean folk medicine. Seoul; Publishing Center of Seoul National University
1966: 39
- 2
Lee M K, Kim Y C.
Five novel neuroprotective triterpene esters of Ulmus davidiana var. japonica.
.
J Nat Prod.
2001;
64
328-31
- 3
Park S, Goo Y M, Na D S.
Isolation and structure elucidation of a catechin glycoside with phospholipase A2
inhibiting activity from Ulmi cortex.
Bull Kor Chem Soc.
1996;
17
101-3
- 4
Kalousová M, Zima T, Tesar V, Stipek S, Sulková S.
Advanced glycation end products in clinical nephrology.
Kidney Blood Press Res.
2004;
27
18-28
- 5
Vlassara H, Cai W, Crandall J, Goldberg T, Oberstein R, Dardaine V. et al .
Inflammatory mediators are induced by dietary glycotoxins, a major risk factor for
diabetic angiopathy.
Proc Natl Acad Sci USA.
2002;
99
15 596-601
- 6
Peyroux J, Sternberg M.
Advanced glycation endproducts (AGEs): Pharmacological inhibition in diabetes.
Pathol Biol.
2006;
54
405-19
- 7
Choi J H, Kim H S, Jung M J, Choi J S.
(+)-Catechin, an antioxidant principle from the leaves of Pinus densinora that acts on 1,1-diphenyl-2-picrylhydrazyl radical.
Nat Prod Sci.
2001;
7
1-4
- 8
Fuchino H, Satoh T, Tanaka N.
Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii.
.
Chem Pharm Bull.
1995;
43
1937-42
- 9
Foo L Y, Karchesy J J.
Polyphenolic glycosides from Douglas fir inner bark.
Phytochemistry.
1989;
28
1237-40
- 10
Lou H, Yamazaki Y, Sasaki T, Uchida M, Tanaka H, Oka S.
A-type proanthocyanidins from peanut skins.
Phytochemistry.
1999;
51
297-308
- 11
Hong N D, Rho Y S, Kim N J, Kim J S.
Studies on the constituents of Ulmi Cortex.
Kor J Pharmacogn.
1990;
21
201-4
- 12
Morikawa T, Tao J, Ueda K, Matsuda H, Yoshikawa M.
Medicinal foodstuffs. XXXI. Structures of new aromatic constituents and inhibitors
of degranulation in RBL-2H3 cells from a Japanese folk medicine, the stem bark of
Acer nikoense.
.
Chem Pharm Bull.
2003;
50
62-7
- 13
Slade D, Ferreira D, Marais J P.
Circular dichroism, a powerful tool for the assessment of absolute configuration of
flavonoids.
Phytochemistry.
2005;
66
2177-215
- 14
Bolton W K, Cattran D C, Williams M E, Adler S G, Appel G B, Cartwright K. et al .
Randomized trial of an inhibitor of formation of advanced glycation end products in
diabetic nephropathy.
Am J Nephrol.
2004;
24
32-40
- 15
Yokozawa T, Nakagawa T.
Inhibitory effects of Luobuma tea and its components against glucose-mediated protein
damage.
Food Chem Toxicol.
2004;
42
975-81
- 16
Urios P, Grigorova-Borsos A M, Sternberg M.
Flavonoids inhibit the formation of the cross-linking AGE pentosidine in collagen
incubated with glucose, according to their structure.
Eur J Nutr.
2007;
46
139-46
- 17
Vinson J A, Howard III T B.
Inhibition of protein glycation and advanced glycation end products by ascorbic acid
and other vitamins and nutrients.
J Nutr Biochem.
1996;
7
659-63
- 18
Engvall E.
Enzyme immunoassay ELISA and EMIT.
Methods Enzymol.
1980;
70
419-39
- 19
Forbes J M, Soulis T, Thallas V, Panagiotopoulus S, Long D M, Vasan S. et al .
Renoprotective effects of a novel inhibitor of advanced glycation.
Diabetologia.
2001;
44
108-14
Dr. Jin Sook Kim
Department of Herbal Pharmaceutical Development
Korea Institute of Oriental Medicine
Daejeon 305–811
Republic of Korea
Phone: +82-42-868-9465
Fax: +82-42-868-9471
Email: jskim@kiom.re.kr
