• Journal of Food Hygiene and Safety
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• v.30 no.1
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• pp.98-102
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• 2015

Oleanolic acid and its derivatives are pentacyclic triterpene acids, which are produced in many plants and herbs. These are considered safe and thus, oleanolic acid is now used for cosmetic and pharmaceutical industry. Oleanolic acid affects peptidoglycan in cell wall of bacteria. Hence, the antimicrobial activity of oleanolic acid is not very obvious to Gram-negative bacteria such as Escherichia coli, Yersinia enterocolitica, Shigella flexneri, and Shigella sonnei because the peptidoglycan is covered with outer membrane. However, oleanolic acid derivatives showed improved antimicrobial activity to Gram-negative bacteria. For Gram-positive bacteria such as Staphylococcus aureus and Listeria monocytogenes, oleanolic acid was very effective on reducing the cell counts of the pathogens. In addition, the cytotoxicity of oleanolic acid for human cell lines was minimal. Therefore, oleanolic acid should be considered as an antimicrobial food additive and a therapeutic agent to control foodborne pathogens.

• 한국생물공학회:학술대회논문집
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• 2003.04a
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• pp.267-270
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• 2003

Oleanolic acid is a triterpenoid compound that exists in Oldenlandia diffusa. Recently, oleanolic acid has been noted for antitumor effect. Application of both plant growth regulators, 2,4-D and kinetin, was found to be essential for the induction of callus and suspension cells. Optimum induction condition for callus and suspension cells of Oldenlandia diffusa was determined to be 0.5 mg/L 2,4-D and 0.1 mg/L kinetin. Chromatographic separation of oleanolic acid from its derivatives was achieved using Rexchrom S5-100-ODS column. The retention time of oleanolic acid was 12.6 min and the specific content of oleanolic acid was 0.41 mg/g dry weight.

• Journal of Ginseng Research
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• v.44 no.1
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• pp.96-104
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• 2020

Objectives: Oleanolic acid, a minor element of ginsenosides, and its derivatives have been shown to have cytotoxicity against some tumor cells. The impact of cytotoxic effect of oleanolic acid 3-acetate on ovarian cancer SKOV3 cells and endometrial cancer HEC-1A cells were examined both in vivo and in vitro to explore the underlying mechanisms. Methods: Cytotoxic effects of oleanolic acid 3-acetate were assessed by cell viability, phosphatidylserine exposure on the cell surface, mitochondrial release of cytochrome C, nuclear translocation of apoptosis-inducing factor, depolarization of mitochondrial transmembrane potential (∆Ψ_m), and generation of reactive oxygen species (ROS). In vivo inhibition of tumor growth was also assessed with xenografts in immunocompromised mice. Results: Oleanolic acid 3-acetate exhibited potent cytotoxicity toward SKOV3 and HEC-1A cells by decreasing cell viability in a concentration-dependent manner. Importantly, oleanolic acid 3-acetate effectively suppressed the growth of SKOV3 cell tumor xenografts in immunocompromised mice. Furthermore, oleanolic acid 3-acetate induced apoptotic cell death as revealed by loss of ∆Ψ_m, release of cytochrome c, and nuclear translocation of apoptosis-inducing factor with a concomitant activation of many proapoptotic cellular components including poly(ADP-ribose) polymerase, Bcl-2, and caspases-8, caspase-3, and caspase-7. Oleanolic acid 3-acetate, however, caused a decrease in ROS production, suggesting the involvement of an ROS-independent pathway in oleanolic acid 3-acetate-induced apoptosis in SKOV3 and HEC-1A cells. Conclusion: These findings support the notion that oleanolic acid 3-acetate could be used as a potent anticancer supplementary agent against ovarian and endometrial cancer. Oleanolic acid 3-acetate exerts its proapoptotic effects through a rather unique molecular mechanism that involves an unconventional ROS-independent but mitochondria-mediated pathway.

• Journal of the Korean Society of Food Science and Nutrition
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• v.45 no.3
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• pp.307-312
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• 2016

We studied the effects of oleanolic acid and hederagenin on acute alcohol-induced hepatotoxicity in mice. Oleanolic acid [10 and 20 mg/kg body weight (BW)/d] or hederagenin (10 and 20 mg/kg BW/d) was orally administered to the study group for 1 week. On the last day of treatment, ethanol (5 g/kg BW) was orally administered to induce acute liver injury. The oleanolic acid-treated group showed lower levels of alanine aminotransferase compared to the ethanol-treated group (EtOH). The mRNA expression level of alcohol dehydrogenase was significantly increased in the high dosage oleanolic acid-treated group compared with the control and EtOH groups. The glutathione levels of the oleanolic acid or hederagenin-treated groups were elevated significantly compared with those of the control and EtOH groups. The mRNA expression levels of glutathione synthetic enzymes were also elevated in the oleanolic acid-treated groups. The oleanolic acid or hederagenin-treated groups also showed lower levels of mRNA expression of tumor necrosis factor alpha. Thus, these results show that oleanolic acid and hederagenin could reduce oxidative stress and hepatotoxicity in ethanol-treated mouse liver.

• The Korean Journal of Physiology and Pharmacology
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• v.21 no.2
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• pp.197-204
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• 2017

In the present study, we tried to examine whether oleanolic acid regulates the activity, secretion and gene expression of matrix metalloproteinase-3 (MMP-3) in primary cultured rabbit articular chondrocytes, as well as the production of MMP-3 in the knee joint of rat to evaluate the potential chondroprotective effect of oleanolic acid. Rabbit articular chondrocytes were cultured in a monolayer, and reverse transcription-polymerase chain reaction (RT-PCR) was used to measure interleukin-$1{\beta}$ (IL-$1{\beta}$)-induced gene expression of MMP-3, MMP-1, MMP-13, a disintegrin and metalloproteinase with thrombospondin motifs-4 (ADAMTS-4), ADAMTS-5 and type II collagen. In rabbit articular chondrocytes, the effects of oleanolic acid on IL-$1{\beta}$-induced secretion and proteolytic activity of MMP-3 were investigated using western blot analysis and casein zymography, respectively. The effect of oleanolic acid on in vivo MMP-3 protein production was also examined, after intra-articular injection to the knee joint of rat. The results were as follows: (1) oleanolic acid inhibited the gene expression of MMP-3, MMP-1, MMP-13, ADAMTS-4, and ADAMTS-5, but increased the gene expression of type II collagen; (2) oleanolic acid reduced the secretion and proteolytic activity of MMP-3; (3) oleanolic acid suppressed the production of MMP-3 protein in vivo. These results suggest that oleanolic acid can regulate the activity, secretion and gene expression of MMP-3, by directly acting on articular chondrocytes.

• YAKHAK HOEJI
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• v.6 no.1
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• pp.25-27
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• 1962

The derivative of glycyrrhetinic acid which have similar effects of desoxycorticosterone acetate was prepared glycyrrhetinyl chloride by the chlorination with thionyl chloride at low temperature. 2-Acetyl-11-keto-.DELTA. : 13 oleanolic ketol acetate (30) was synthesized by diazotating glycyrrhetinyl chloride with diazomethan and the acetylation with anhydro acetic acid. 2-Acetyl-.DELTA.12 : 13 oleanolic ketol acetate (28) was synthesized by chlorinating oleanolic acid with thionyl chloride, and by diazotatating oleanolyl chloride with diazomethan and the acetylation with anhydroacetic acid.

• YAKHAK HOEJI
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• v.26 no.1
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• pp.1-8
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• 1982

Derivation of triterpenoids and then the screening for corticomimetics among them is our primary interest. $C_{11}$-oxo-triterprenoids except glycyrrhetinic acid are rarely found in the plant kingdom. Based on the facts that $C_{3}$ and $C_{11}$-Oxo-group are essential for the corticoid-like-activity through its competitive inhibition on the corticoid-5.betha.-reductase, it was attempted to produce artificial inhibitor on the enzyme by introducing $C_{11}$-oxo group to the triterpenoids of oleanene series such as oleanolic acid and hederagenin. We could obtain the $C_{11}$-oxo-oleanolic acid m.p. $264-6^{\circ}$, uv ${\lambda}max$ 249 and $C_{11}$-oxo-hederagenin amorp. uv ${\lambda}max$ 251 by acetylation, $CrO_{3}$-oxid., and deacetylation. Glycyrrhetinic acid, a natural 11-oxo-compound and the other 11-oxo-derivatives of oleanolic acid and hederagenin were compared in their inhibitory activity on the corticoid-5.betha.-reductase. The inhibitory activity of those compound were decreased in the order of $C_{11}$-oxo-oleanolic acid, $C_{11}$-oxo- hederagenin, glycyrrhetinic acid. This suggests more strong corticomimetic activity of those artificially derived $C_{11}$-oxo-oleanolic acid and $C_{11}$-oxa-hederagenin. Their Ki value were $4.6{\times}10^{-4}M$ and $5.8{\times}10^{-4}M$ respectively.

• Archives of Pharmacal Research
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• v.16 no.2
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• pp.104-108
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• 1993

From the root barks of Araila elata Seem.(Araliaceae) three known saponins together with oleanolic acid and $\beta$-sitosterol $3-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucopyranosyl ester, oleanolic acid $3-O-\beta$-D-glucuronopyranoside and oleanolic acid $3-O-\alpha$-L-arabinofuranoysyl-(1$\rightarrow$4)-$\beta$-D-glucuronopyranoside(narcissiflo on the basis of chemical and spectra data. The latter two saponins were isolated as their dimethylesters as well as monomethylesters.

• Archives of Pharmacal Research
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• v.6 no.1
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• pp.29-33
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• 1983

From the roots of Pandia siamensis, D-mannitol, a mixture of .betha.-sitosterol and campesterol, oleanolic acid acetate, oleanolic acid-3-.alpha.-L-arabino side and mesembryanthemoidigenic acid as a sapogenin were isolated and characterized.

• Archives of Pharmacal Research
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• v.22 no.4
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• pp.428-431
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• 1999

Seven known oleanolic acid glycosides (1-7) were isolated form the MeOH extract of Tiarella polyphylla. The structures were identified to be 3-O-($\beta$-glucopyranosyl) oleanolic acid (1), 3-O-[$\beta$-D-glucopyranosyl-(1 3)-$\beta$-D-glucopyranosyl] oleanolic acid (2), 3-O-D-[$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glycopyranosyl] oleanolic acid (3), 3-O-[$\beta$-D-glucopyranosyl-(1 3)-$\beta$-D-glucopyranosyl] oleanolic acid 28-O-$\beta$D-glucopyranosyl ester (4), 3-O-[$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glucopyranosyl] oleanolic acid 28-O-$\beta$-D-glucopyranosyl ester (5), 3-O-[a-L-rahmnopyranosyl-(1 3)-$\beta$-D-glucururonopyranosyl] oleanolic acid (6), and 3-O-[$\alpha$-L-rhamnopyranosyl-(1 3)-$\alpha$-D-glucuronopyranosyl] oleanolic acid 28-O-$\alpha$-D-glucopyranosyl ester (7) on the basis of physicochemical and spectral data. These triterpene glycosides were tested for the anti-complement activity and hemolytic activity. Bisdesmosidic saponins, 4, 5, and 7, showed anti-complement activity; in contrast, monodesmosidic saponins, 1-3, and 6, showed direct hemolytic activity. Methyl esterified monodesmosidic saponins showed anti-complement activity at a low concentration and hemolytic activity at a high concentration.