587
Activity of oleanolic acid derivatives on gastric lesions
1
-
protease with an IC50 of 10 lg mL (Ma et al 2000),
inhibition of DNA polymerase b (Deng et al 1999),
cytotoxicity against cultured human tumour cell lines
(Kim et al 2000), chitin synthase II inhibitory activity
References
Handbookof naturalproducts data.
Ahmad, V. U., Rahman,A. (1994)
Volume 1. Pentacyclic triterpenoids
. Elsevier, Amsterdam, pp 86±
87, 111±112
1
-
with an IC50 of 5.6 lg mL (Jeong et al 1999), inhibi-
Antonio, M., Souza Brito, A. (1998)Oral anti-in¯ ammatory and anti-
tion of 12-O-tetradecanoylphorbol-13-acetate stimu-
lated 32Pi-incorporation into phospholipids of cultured
cells (Kinoshita et al 1999), and inhibition of insoluble
glucan synthesis from Streptococcus mutans (Kozai et al
1999).
Turnera ulmifolia
(Turneraceae).
steroid dehydrogenase: an evolutionary perspective.
Several biological activities have been associated with
OA and its close relative ursolic acid. OA is widely
distributed in plants and occurs in several medicinal and
food plants in variable concentrations. The pharma-
cology of OA and ursolic acid has been revised by Liu
(1995). Both compounds are eŒective against chemically
induced liver injury and have anti-in¯ ammatory and
antihyperlipidaemic properties in laboratory animals
and antitumour-promotion eŒects.
Deng, J. Z., Starck, S. R., Hecht, S. M. (1999) DNA polymerase beta
inhibitors from
.
Desai, J. K., Parmar, N. S. (1993) Gastric and duodenal anti-ulcer
Statistics for toxicologists principles and
.
Gad, S., Weil, C. (1994)
methods of toxicology
. Wallace, A. (ed.) Raven Press, Ltd., New
York, pp 221±274
Hiruma-Lima, C., Gracioso, J., Toma, W., Almeida, A., Paula, A.,
Brasil, D., Muller, A., Souza Brito, A. (2001) Gastroprotective
Aparisthmium
eŒect of aparisthman, a diterpene isolated from
OA and its glycosides display hepatoprotective ac-
tivity. Kinjo et al (1999) studied the protective eŒects of
OA saponins and its derivatives on in-vitro immuno-
logical liver injury of primary cultured rat hepatocytes.
OA showed both hepatoprotective action and weak
hepatotoxicity, while the eŒect of the saponins repre-
sented a balance between hepatoprotective action and
hepatotoxicity. The protective eŒects of OA against car-
bon tetrachloride (CCl4)-induced hepatotoxicity may,
at least in part, be owing to its ability to block bio-
activation of CCl4 mainly by inhibiting the expression
and activity of cytochrome P450 2E1 (Jeong 1999).
Other studies on OA and its derivatives include the
anti-HIV activity of OA, pomolic acid and structurally
related triterpenoids (Kashiwada et al 1998). OA inhi-
bited HIV-1 replication in acutely infected H9 cells with
Jeong, H. G. (1999)Inhibition of cytochrome P450 2E1 expression by
chloride-induced hepatic injury.
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. (1999) Chitin synthase II
Crataegus pinna
inhibitory activity of ursolic acid, isolated from
-
.
Kashiwada, Y., Wang, H. K., Nagao, T., Kitanaka, S., Yasuda, I.,
Fujioka, T., Yamagishi, T., Cosentino, L. M., Kozuka, M., Okabe,
H., Ikeshiro, Y., Hu, C. Q., Yeh, E., Lee, K. H. (1998) Anti-AIDS
structurally related triterpenoids.
Kim, Y. K., Yoon, S. K., Ryu, S. Y. (2000) Cytotoxic triterpenes
from stem bark of
Kinjo, J., Okawa, M., Udayama, M., Sohno, Y., Hirakawa, T., Shii,
Y., Nohara, T. (1999) Hepatoprotectiveand hepatotoxic actions of
oleanolic acid-type triterpenoidal glucuronides on rat primary
1
-
an EC50 of 1.7 lg mL , and inhibited H9 cell growth
1
-
with an IC50 of 21.8 lg mL , being less toxic than
hepatocyte cultures.
Kinoshita, K., Yang, Y., Koyama, K., Takahashi, K., Nishino, H.
(1999) Inhibitory eŒect of some triterpenes from cacti on 32Pi-
incorporation into phospholipids of HeLa cells promoted by 12-O-
ursolic acid. OA derivatives proved to be even more
active than the natural product.
In conclusion, this study demonstrates that OA dis-
plays a signi®cant gastroprotective eŒect against gastric
ulcers induced by pyloros ligature and ethanol in rats.
The gastroprotective eŒect was dose-dependent in the
ethanol model and was not diŒerent at doses of 100 and
tetradecanoylphorbol-13-acetate.
Kozai, K., Suzuki, J., Okada, M., Nagasaka, N. (1999) EŒect of
by in vitro experimentand rat-caries model.
Lewis, D. A., Hanson, D. (1991) Anti-ulcer drugs of plant origin. In:
Progress in medicinal chemistry
Ellis, G. P., West, G. B. (eds)
.
1
-
200 mg kg . Some structure±activity relationships can
Elsevier Science Publishers, B. V., Amsterdam, pp 201±231
be deduced from the experiment with OA and its deriva-
tives. Oxidation of the OH at C-3 reduced the activity of
the triterpene, whereas methylation of the COOH at C-
28 with or without acetylation at C-3 did not aŒect the
gastroprotective eŒect of the compounds. More studies
are necessary to determine the mechanism of action of
OA and its derivatives.
Litch®eld, J. T. Jr, Wilcoxon, F. (1949) A simpli®ed method of
Ma, C., Nakamura, N., Hattori, M., Kakuda, H., Qiao, J., Yu, H.
(2000)Inhibitory eŒects on HIV-1 protease of constituentsfrom the
wood of
.