• 한국식품위생안전성학회지
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• 제30권1호
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• pp.98-102
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• 2015

Oleanolic acid는 다수의 식물 종에서 분리 되어 왔고 주로 유해한 영향이 없는 과일과 약초에 존재하기 때문에 전세계적으로 많은 나라에서 안전하게 소비되고 있으며, 현재는 화장품이나 약품에 사용되고 있다. Oleanolic acid는 peptidoglycan을 표적으로 하기 때문에 petidoglycan이 세균외막에 덮여있는 그람음성세균인 E. coli, Y. enterocolitica, S. flexneri, S. sonnei와 같은 세균에는 뚜렷한 oleanolic acid 항균활성이 관찰되지 않았다. 하지만 oleanolic acid의 유도체를 사용할 경우 그람음성세균에 대한 항균활성도 증가하였다. 반면 S. aureus와 L. monocytogenes와 같은 그람양성세균의 경우 peptidoglycan층이 세균외막에 덮여 있지 않기 때문에 oleanolic acid에 매우 민감하였다. 또한 oleanolic acid는 사람에 대한 세포독성 실험에서도 그 독성이 낮은 것으로 판단되었기 때문에 식중독 세균제어를 목적으로 연구를 진행할 필요가 있으며, 이 결과들은 식품에 적용되거나 항생제 대체를 위한 치료목적으로도 사용될 수 있을 것으로 사료된다.

• 한국생물공학회:학술대회논문집
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• 한국생물공학회 2003년도 생물공학의 동향(XII)
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• pp.267-270
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• 2003

백화사설초에 함유되어 있는 oleanolic acid를 세포배양을 이용하여 생산하기 위한 연구를 수행하였다. Oleanolic acid를 생산하기 위해, 백화사설초의 캘러스와 현탁세포를 2,4-D 0.5 mg/L, kinetin 0.1 mg/L가 포함된 SH 배지에서 유도하였다. Oleanolic acid의 분석을 위해, Rexchrom S5-100-ODS column을 사용한 HPLC를 이용하였다. 분석 결과, oleanolic acid의 retention time은 12.6분 이었고, 그 양은 0.41 mg/g dry weight였다.

• Journal of Ginseng Research
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• 제44권1호
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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.

• 한국식품영양과학회지
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• 제45권3호
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• pp.307-312
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• 2016

본 연구는 선행연구를 통한 으름 추출물의 간 보호 효과에 대하여 으름 추출물 내 유효물질로 알려진 oleanolic acid와 hederagenin을 생쥐에 투여하였을 때 알코올로 인한 급성 간독성 상태에서 간 보호 효과를 조사하였다. 그 결과 oleanolic acid와 hederagenin의 투여는 알코올로 유발된 급성 간독성 상태에서 혈중 알코올 농도 감소 및 alcohol dehydrogenase mRNA 발현을 증가시키는 것으로 나타났으며, 간 조직 내 항산화 물질인 glutathione(GSH)의 농도를 증가시키고, GSH synthetic enzyme의 mRNA 발현 역시 증가시키는 것으로 확인되었다. 또한 염증반응 지표인 tumor necrosis factor-alpha의 mRNA 발현도 억제하는 것으로 분석되었다. 위의 결과들과 기존의 실험에서 확인한 으름 추출물의 간 보호 효과를 종합하였을 때 으름 추출물의 알코올로 유발된 산화 스트레스, 염증반응에 대한 간 보호 효과는 추출물 내 유효물질로 알려진 oleanolic acid 및 hederagenin의 작용에 의한 것이라 생각한다.

• The Korean Journal of Physiology and Pharmacology
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• 제21권2호
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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.

• 약학회지
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• 제6권1호
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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.

• 약학회지
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• 제26권1호
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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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• 제6권1호
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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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• 제16권2호
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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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• 제22권4호
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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.