• 약학회지
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• 제35권3호
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• pp.147-153
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• 1991

Chemical constituents of fruits, leaves and barks of Acanthopanax senticosus forma inermis were studied. Their fruits have higher contents of crude ash, crude protein, crude fat, fructose and glucose than those of other Acanthopanax species, and contained larger amount of glutamic acid and malic acid among amino acid and organic acid, respectively. The compounds identified from their barks and leaves, were $\beta$-sitosterol and stigmasterol, sesamin, savinin, syringaresinol diglucoside, oleanolic acid, chiisanoside and polyacetytene ($C_9H_{10}O_2$, mp. 62~63).

• Journal of Applied Biological Chemistry
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• 제48권4호
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• pp.207-212
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• 2005

Prolyl endopeptidase (PEP, EC 3.4.21.26), also referred to as prolyl oligopeptidase, has been suggested to participate in learning and memory processes by cleaving peptide bonds on carboxyl side of prolyl residue within neuropeptides of less than 30 amino acids, and is abundant in brains of amnestic patients. Therefore, compounds possessing PEP inhibitory activity can be good candidate of drug against memory loss. Upon examination for PEP inhibition from traditional medicinal plants having tonic, stimulating, and anti-amnestic effects, Corni Fructus (Cornus officinallis) showed significant PEP inhibition. Ursolic and oleanolic acids, components of Corni Fructus, inhibited PEP with $IC_{50}$ values of $17.2\;{\pm}\;0.5$ and $22.5\;{\pm}\;0.7\;{\mu}M$, respectively.

• 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.

• 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.

• Molecules and Cells
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• 제41권8호
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• pp.771-780
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• 2018

Angiogenesis must be precisely controlled because uncontrolled angiogenesis is involved in aggravation of disease symptoms. Vascular endothelial growth factor (VEGF)/VEGF receptor 2 (VEGFR-2) signaling is a key pathway leading to angiogenic responses in vascular endothelial cells (ECs). Therefore, targeting VEGF/VEGFR-2 signaling may be effective at modulating angiogenesis to alleviate various disease symptoms. Oleanolic acid was verified as a VEGFR-2 binding chemical from anticancer herbs with similar binding affinity as a reference drug in the Protein Data Bank (PDB) entry 3CJG of model A coordination. Oleanolic acid effectively inhibited VEGF-induced VEGFR-2 activation and angiogenesis in HUVECs without cytotoxicity. We also verified that oleanolic acid inhibits in vivo angiogenesis during the development and the course of the retinopathy of prematurity (ROP) model in the mouse retina. Taken together, our results suggest a potential therapeutic benefit of oleanolic acid for inhibiting angiogenesis in proangiogenic diseases, including retinopathy.

• 생명과학회지
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• 제8권2호
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• pp.162-166
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• 1998

전 골수성 백혈병 세초인 HL-60 세포를 model로 하여, 민간요법으로 사용되어져 부작용이 극히 적은 거승로 알려진 고려인삼의 구성 성분 중 주요성분이 ginseng (Panzx ginseng C.A. Meyer) saponin 및 ginsenoside Rh1, Rh2, Rh3, 비파 (Eriobotrya japonica L.) 잎의 성분들 중에서 항발암 및 항암성분으로 알려진 ursolic acid 및 oleanolic acid, 웅담중의 중요성분 성분인 lithocholoc acid 드잉 분화능력이 있는 지를 조사하고자 본 실험을 수행아였다. Retinoic acid를 처리한 결과 타 연구자들의 연구결과들처럼 높은 분화력을 관찰할 수 있었으며, dbcAMP 단독 처리군에서도 높은 분화효과를 나타냈었다. Dexamethasone 처리군에서는 분화효과를 거의 관찰할 수 없었으나,dexamethansone과 구조적으로 유사한 ursolic acid와 oleanolic acid는 보다 높은 분화력을 보였고 웅담성분의 중요성분인 lirhocholic acid는 높은 분화력을 나타냈었다. Ginseng saponin은 0.00375% (w/v)에서 20% 이상의 분화력을 보였으며, Ginsenoside Rh2와 Rh3는 높은 분화력을 나타냈다.

• 생약학회지
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• 제41권1호
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• pp.62-66
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• 2010

In result of analysis for the content determination of ursolic acid(UA) and oleanolic acid(OA) in extract of Eriobotryae folium using HPLC with UV detector, UA in chloroform extract of Moo-mok variety was showed highest content(2.7843 mg/g). And OA in ethyl acetate extract of Dae-bang variety was showed highest content(0.5898 mg/g). These result suggest that direct extraction using organic solvent(chloroform or ethyl acetate) was useful method for rapid quantitative analysis of UA and OA without preprocessing such as drying or fractionation.

• 생약학회지
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• 제33권4호통권131호
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• pp.267-271
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• 2002

Prunasin and pomolic acid together with a mixture of ursolic and oleanolic acids, (-)-epicatechin and ${\beta}-sitosterol$ glucoside were isolated from the roots of Chaenomeles japonica. Among these compounds, the isolation of pomolic acid and prunasin is the first report from the genus Chaenomeles.

• 대한화장품학회:학술대회논문집
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• 대한화장품학회 2003년도 IFSCC Conference Proceeding Book II
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• pp.319-329
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• 2003

Ursolic acid (UA) and oleanolic acid (OA) are pentacyclic triterpenoids which are widely distributed in plants, and their derivatives are aglycones of many naturally occurring saponins. It is known that pentacyclic acids may possibly enhance the mechanical barrier functions of cell membranes in plants. Recently, it has been reported that OA and UA have interesting biological activities on skin, such as anti-inflammatory and anti-wrinkle activities. Since triterpenoids are extremely insoluble and their solubility problem limits skin-care application, OA and UA were encapsulated in liposomes via micelle-to-vesicle transition to overcome poorly soluble property and enhance biological efficacy. Optimal molar ratio of OA to lecithin was found to exist for producing liposomes of small hydrodynamic size and liposomal suspensions without recrystallized precipitation of OA. From electron micrograph and dynamic light scattering studies, reconstituted OA-containing liposomes without severe mechanical treatment showed small hydrodynamic size about 150 nm. Wide-angle X-ray diffraction coupled with dynamic light scattering revealed that optimal amount of OA in liposome was 25.4 mole %. In biological evaluation, OA-containing liposome significantly increased filaggrin and transglutaminase as markers of keratinocyte differentiation in epidermal layer of hairless mouse, whereas ursolic acid-containing liposome did not show noticeable increase of filaggrin and transglutaminase compared to empty liposome. It is concluded that nano-scaled liposomes containing triterpenoids were spontaneously prepared by vesicular transition from mixed micelle and liposomal triterpenoids can enhance skin absorption of triterpenoid and biological efficacy.

• Archives of Pharmacal Research
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• 제21권4호
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• pp.398-405
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• 1998

We investigated the effects of triterpene acids (TAs), ursolic acid (UA) and oleanolic acid (OA), on the induction of proliferation and differentiation of normal rat mammary epithelial cells (RMEC) or organoids cultured in Matrigel or primary culture system. To elucidate the effects, we tested their differentiation inducing activities with intercellular communication ability, cell cycle patterns, induction of apoptosis, and morphological differentiation in the three dimensional extracellular culture system. To study the changes of RMEC subpopulation in culture, the cultured cells were isolated, immunostained with peanut lectin (PNA) and anti-Thy-1.1 antibody and then analyzed with flow cytometry. Four different subpopulations, such as PNA and Thy-1.1 negative cells (B-), PNA positive cells (PNA+), Thy-1.1 positive cells (Thy-1.1+), PNA and Thy-1.1 positive cells (B+), were obtained and the size of each subpopulation was changed in culture with time in the presence of TAs. Intercellular communication was observed in culture for 7 days in TAs-treated cells, but not in culture for 4 days with scrape-loading dye transfer technique. $G_2$/M phase cells and the number of apoptotic population were increased in TAs-treated groups in cell cycle analyses. S phase fractions were reduced and the change of $G_1$ phase cells was not observed. The colonies with distinct multicelfular structures, such as stellate, ductal, webbed, squamous, lobulo-ductal colonies, were observed in Matrigel culture and the frequencies of each colony were changed in the presence of TAs. These results suggest that UA and OA have differentiation inducing effects on rat mammary epithelial cells in primary or in Matrigel culture.