Abstract
Two new furo-1,2-naphthoquinones, crataequinones A (1) and B (2), were isolated from the fruits of Crataegus pinnatifida. The structures of two new compounds were determined as 11,12-dimethoxy-3,4-furo-1,2-naphthoquinone (1) and 11,12-dimethoxy-5-hydroxy-3,4-furo-1,2-naphthoquinone (2) by spectroscopic analysis. The two compounds 1 and 2 showed significant inhibitory activity with IC50 values of 33 and 90 μM, respectively, against the expression of intercellular adhesion molecule-1 (ICAM-1).
Key words
Furo-1,2-naphthoquinone
-
Crataegus pinnatifida
- Rosaceae
- crataequinone A
- crataequinone B
- ICAM-1 inhibitory activity
References
-
1
Ahn K S, Kim J H, Oh S R, Ryu S Y, Lee H K.
Inhibitory activity of stilbenes from medicinal plants on the expression of cell adhesion molecule on THP1 cells.
Planta Medica.
2000;
66
641-4
-
2
Buckle A M, Hogg N.
Human memory T cells express intercellular adhesion molecule-1 which can be increased by interleukin 2 and interferon-gamma.
Eur J Immunol.
1990;
20
337-41
-
3
Webb D S, Mostowski H S, Gerrard T L.
Cytokine-induced enhancement of ICAM-1 expression results in increased vulnerability of tumor cells to monocyte-mediated lysis.
J Immunol.
1991;
146
3682-9
-
4
Ahn K S, Jung K Y, Kim J H, Oh S R, Lee H K.
Inhibitory activity of lignan components from the flower buds of Magnoliae fargesii on the expression of cell adhesion molecules.
Biol Pharm Bull.
2001;
24
1085-7
-
5
Min B S, Jung H J, Lee J S, Kim Y, Bok S H, Ma C M, Nakamura N, Hattori M, Bae K H.
Inhibitory effect of triterpenes from Crataegus pinnatifida on HIV-1 protease.
Planta Medica.
1999;
65
374-5
-
6
Jeong T S, Hwang E I, Lee H B, Lee E S, Kim Y K, Min B S, Bae K H, Bok S H, Kim S U.
Chitin synthase II inhibitory activity of ursolic acid, isolated from Crataegus pinnatifida
.
Planta Medica.
1999;
65
261-3
-
7
Min B S, Kim Y H, Lee S M, Jung H J, Lee J S, Na MK Lee C O, Lee J P, Bae K H.
Cytotoxic triterpenes from Crataegus pinnatifida
.
Arch Pharm Res.
2000;
23
155-8
-
8
Al-Numani D, Segura M, Dore M, Gottschalk M.
Up-regulation of ICAM-1, CD11a/CD18 and CD11c/CD18 on human THP-1 monocytes stimulated by Streptococcus suis serotype 2.
Clin Exp Immunol.
2003;
133
67-77
-
9
Ahmed S A, Gogal R M, Walsh J E.
A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: an alternative to [3
H]thymidine incorporation assay.
J Immunol Methods.
1994;
170
211-24
-
10
Dustin M L, Rothlein R, Bhan A K, Dinarello C A, Springer T A.
Induction by IL-1 and interferon-gamma: tissue distribution, biochemistry, and function of a natural adherence molecule (ICAM-1).
J Immunol.
1986;
137
245-54
-
11
Inoue K, Ueda S, Nayeshiro H, Inouye H.
Quinones of Streptocarpus dunnii
.
Phytochemistry.
1983;
22
737-41
-
12
Rothlein R, Czajkowski M, O’Neil M M, Marlin S D, Mainolfi E, Merluzzi V J.
Induction of intercellular adhesion molecule 1 on primary and continuous cell lines by pro-inflammatory cytokines. Regulation by pharmacologic agents and neutralizing antibodies.
J Immunol.
1988;
141
1665-9
Dr. KiHwan Bae
College of Pharmacy
Chungnam National University
Daejeon 305-764
Korea
Phone: +82-42-821-5925
Fax: +82-42-823-6566
Email: baekh@cnu.ac.kr
