Abstract
Two novel compounds, 3-methoxypterolactone (1 ) and 2-amino-3,4-dihydroxy-5-methoxybenzoic acid (2 ), were isolated from leaves of Cyclocarya paliurus (Batal.) Iljinsk, together with nine known compounds: pterolactone (3 ), gallic acid (4 ), 4-hydroxy-3-methoxybenzoic acid (5 ), oleanolic acid (6 ), β-boswellic acid (7 ), α-boswellic acid (8 ), β-amyrin (9 ), β-amyrone (10 ) and 3β-O-trans -caffeoyl-morolic acid (11 ). The structure elucidation was based on spectroscopic methods, including two-dimensional NMR experiments (1 H-1 H COSY, HMQC and HMBC). All isolated compounds were evaluated for their glycosidase and glycogen phosphorylase inhibitory activities. 2-Amino-3,4-dihydroxy-5-methoxybenzoic acid and gallic acid showed significant α-glucosidase and glycogen phosphorylase inhibitory activities.
Key words
Cyclocarya paliurus
- Cyclocaryaceae - 3-methoxypterolactone - 2-amino-3,4-dihydroxy-5-methoxybenzoic acid - α-glucosidase - glycogen phosphorylase
References
1 He S A. Chinese rare plants. Shanghai; Shanghai Science and Technology Press 1988: 72-3
2 Plant Index Editional committee of the Chinese Academy of Science. The plant index of China, Vol. 23. Beijing; Scientific Press 1979: 18-9
3
Shu R G, Xu C R, Li L N, Yu Z L.
Cyclocariosides and secondammarane triterpenoid saponins from Cyclocarya Paliurus .
Planta Med.
1995;
61
551-3
4
Shu R Y, Xu C R, Li L N.
Studies on the sweet principle from the leaves of Cyclocarya paliurus (Batal.) Iljinsk.
Acta Pharmaceut Sin.
1995;
30
757-61
5
Zhong R J, Gao Y H, Xu C R, Li L N.
Pentacyclic triterpenoids from roundingfruits Cyclocarya paliurus.
.
Chin Tradit Herb Drugs.
1996;
27
387-9
6
Zhong R J, Gao Y H, Ni X L, Xu C R, Li L N.
Studies on chemical structure of cyclocalic acid A.
Acta Pharmaceut Sin.
1996;
31
398-400
7
Li J, Lu Y Y, Li F.
Advance on the study of Cyclocarya paliurus.
.
J Jiangxi Univ Tradit Med.
2006;
18
76-7
8
Zhou G X, Zhang Y J, Peng D M, Yu D Q, Chen Y F.
Pterolactone, a new norsesquiterpene lactone from Pterocarya stnoptera .
J Chin Pharm Sci.
1999;
8
11-4
9
Kroes B H, Van den Berg A JJ, Van Ufford H CQ, Van Dijk H, Labadie R P.
Anti-inflammatory activity of gallic acid.
Planta Med.
1992;
58
499-504
10
Yamanak M, Shimomura K, Sasak K, Yoshihira K, Ishimaru K.
Glucosylation of phenolics by hairy root cultures of Lobelia sessilifolia .
Phytochemistry.
1995;
40
1149-50
11
Bajad S, Bedi K, Singla A, Johri R.
Antidiarrhoeal activity of piperine in mice.
Planta Med.
2001;
67
284-7
12
Belsner K, Buchele B, Werz U, Syrovets T, Simmet T.
Structural analysis of pentacyclic triterpenes from the gum resin of Boswellia serrata by NMR spectroscopy.
Magn Reson Chem.
2003;
41
115-22
13
Zhou J Y, Cui R.
Chemical constituents of Boswellia serrata.
.
Acta Pharmaceut Sin.
2002;
37
633-5
14
Hasmeda M, Kweifio-Okai G, Macrides T, Polya G M.
Selective inhibition of eukaryote protein kinases by anti-inflammatory triterpenoids.
Planta Med.
1999;
65
14-8
15
Luo X D, Wu S H, Ma B Y, Wu D G.
The chemical constituents of Amoora yuuanensis .
Acta Bot Sin.
2001;
43
426-30
16
Guo X D, An L K, Xu D, Ma L, Gu L Q.
New triterpenoids from Helicteres angus tifolia .
Chem J Chin Univ.
2003;
24
2022-3
17
Pierre C, Roland R, Tremblay D.
p -Nitrophenol-α-glucopyramoside as substrate for measurement of maltase activity in human semen.
J Clin Chem.
1978;
24
208-11
18
Martin W H, Hoover D J, Armento S J, Stock I A, McPherson R K, Danley D E. et al .
Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo .
Proc Natl Acad Sci USA.
1998;
95
1776-81
Prof. Dr. Yongcheng Lin Dr. Zhigang She
School of Chemistry and Chemical Engineering
Sun Yat-sen University
Guangzhou 510275
People’s Republic of China
Phone: +86-20-8403-9623
Fax: +86-20-8403-9623
Email: ceslyc@mail.sysu.edu.cn
Email: cesshzhg@mail.sysu.edu.cn