• Title/Summary/Keyword: Ursolic Acid

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Oleanolic acid regulates NF-κB signaling by suppressing MafK expression in RAW 264.7 cells

  • Hwang, Yu-Jin;Song, Jaewhan;Kim, Haeng-Ran;Hwang, Kyung-A
    • BMB Reports
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    • v.47 no.9
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    • pp.524-529
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    • 2014
  • Oxidative stress and inflammation are common to many pathological conditions. Defense mechanisms protect cells from oxidative stress, but can become over-activated following injury and inflammation. NF-${\kappa}B$ and Nrf2 transcription factors regulate proinflammatory and antioxidant gene expression, respectively. Studies have shown that many natural dietary compounds regulate NF-${\kappa}B$ and Nrf2, preventing inflammation and oxidative stress. Here, we report major compounds of Prunella vulgaris var. lilacina such as rosmarinic acid, oleanolic acid, ursolic acid and caffeic acid as a potential therapeutic for oxidative stress and inflammation. The major compounds exhibited high anti-inflammatory activity, inhibiting NO, PGE2 production, NF-${\kappa}B$ expression and activating Nrf2 expression. In addition, we examined the effect of major compounds on MafK expression. Among the compounds, oleanolic acid significantly decreased MafK expression and MafK-mediated p65 acetylation. These findings suggest that oleanolic acid as NF-${\kappa}B$ inhibitors can potentially be used in therapeutic applications for the treatment of oxidative stress-induced diseases.

Antioxidant Flavonoids and Chlorogenic Acid from the Leaves of Erobotrya japonica

  • Jung, Hyun-Ah;Park, Jong-Cheol;Chung, Hae-Young;Kim, Jong;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.22 no.2
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    • pp.213-218
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    • 1999
  • The antioxidant activity of Eriobotrya japonica was determined by measuring the radical scavenging effect on DPPH (1,1-diphenyl-2-picrylhydrazyl) radical and lipid peroxidation produced when mouse liver homogenate was exposed to the air at $37^{\circ}C$, using 2-thiobarbituric acid (TBA). The methanol extract and its factions of Eriobotrya japonica leaves showed strong antioxidant activity. The antioxidant activity of EtOAc and n-BuOH soluble fractions were stronger than the others, and were further purified by repeated silica gel, MCl gel CHP-20P, and Sephadex LH-20 column chromatography. Antioxidant chlorogenic acid, quercetin-3-sambubioside from n-BuOH fraction and methyl chlorogenate, kaempferol- and quercetin-3-rhamnosides, together with the inactive ursolic acid and$ 2{\alpha}$-hydroxyursolic acid from EtOAc fraction were isolated. Antioxidant flavonoids and chlorogenic acid also showed prominent inhibitory activity against free radical generation in dichlorofluorescein (DCF) method.

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Effective Component Contents and Antioxidative Activities of Unripe Apple by Extraction Methods (추출방법에 따른 미숙사과 추출물의 유용성분 함량 및 항산화 활성)

  • Hong, Jeong Jin;Seol, Hui Gyeong;Oh, Ju Youl;Jeong, Eun Ho;Chang, Young Ho
    • The Korean Journal of Food And Nutrition
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    • v.34 no.2
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    • pp.174-180
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    • 2021
  • The purpose of this study was to determine the optimum extraction method suitable for the availability of biological activities in unripe apples known to be rich in functional components. Unripe apples 'Hongro' picked on May 28th, 2019 were extracted by various extraction methods (hot water, ethanol, enzymatic pre-treatment, ultrasonic wave, and subcritical water) and their extracts were investigated yield, effective component contents, and antioxidant activities. Overall, the yields by the extraction solvent were higher in water than in organic solvent(ethanol) because water-soluble compounds were eluted from a polar solvent. Total phenol contents of the ultrasonic wave (ethanol) extracts were significantly higher in 6 times than hot water extract. Contents of flavonoid were highest in the ethanol extract at 29.14 mg QE/g. Contents of tannin and ursolic acid were also significantly higher in the ultrasonic wave (ethanol) extract. The DPPH radical and ABTS radical scavenging activities were the strongest in the ultrasonic wave (ethanol) extract. Correlation between effective components and antioxidant activities was high in the total phenol content with ABTS and the ursolic acid content with DPPH (p<0.01). The above results suggested that ultrasonic wave (ethanol) extract of unripe apples has the potential to act as a functional material.

The Effect of Two Terpenoids, Ursolic Acid and Oleanolic Acid on Epidermal Permeability Barrier and Simultaneously on Dermal Functions (우솔릭산과 올레아놀산이 피부장벽과 진피에 미치는 영향에 대한 연구)

  • Suk Won, Lim;Sung Won, Jung;Sung Ku, Ahn;Bora, Kim;In Young, Kim;Hee Chang , Ryoo;Seung Hun, Lee
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.2
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    • pp.263-278
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    • 2004
  • Ursolic acid (UA) and Oleanolic acid (ONA), known as urson, micromerol and malol, are pentacyclic triterpenoid compounds which naturally occur in a large number of vegetarian foods, medicinal herbs, and plants. They may occur in their free acid form or as aglycones for triterpenoid saponins, which are comprised of a triterpenoid aglycone, linked to one or more sugar moieties. Therefore UA and ONA are similar in pharmacological activity. Lately scientific research, which led to the identification of UA and ONA, revealed that several pharmacological effects, such as antitumor, hepato-protective, anti-inflammatory, anticarcinogenic, antimicrobial, and anti-hyperlipidemic could be attributed to UA and ONA. Here, we introduced the effect of UA and ONA on acutely barrier disrupted and normal hairless mouse skin. To evaluate the effects of UA and ONA on epidermal permeability barrier recovery, both flanks of 8-12 week-old hairless mice were topically treated with either 0.01-0.1mg/mL UA or 0.1-1mg/mL ONA after tape stripping, and TEWL (transepidermal water loss) was measured. The recovery rate increased in those UA or ONA treated groups (0.1mg/mL UA and 0.5mg/mL ONA) at 6h more than 20% compared to vehicle treated group (p < 0.05). Here, we introduced the effects of UA and ONA on acute barrier disruption and normal epidermal permeability barrier function. For verifying the effects of UA and ONA on normal epidermal barrier, hydration and TEWL were measured for 1 and 3 weeks after UA and ONA applications (2mg/mL per day). We also investigated the features of epidermis and dermis using electron microscopy (EM) and light microscopy (LM). Both samples increased hydration compared to vehicle group from 1 week without TEWL alteration (p < 0.005). EM examination using RuO4 and OsO4 fixation revealed that secretion and numbers of lamellar bodies and complete formation of lipid bilayers were most prominent (ONA=UA > vehicle). LM finding showed that thickness of stratum corneum (SC) was slightly increased and especially epidermal thickening and flattening was observed (UA > ONA > vehicle). We also observed that UA and ONA stimulate epidermal keratinocyte differentiation via PPAR Protein expression of involucrin, loricrin, and filaggrin increased at least 2 and 3 fold in HaCaT cells treated with either ONA (10${\mu}$M) or UA (10${\mu}$M) for 24 h respectively. This result suggested that the UA and ONA can improve epidermal permeability barrier function and induce the epidermal keratinocyte differentiation via PPAR Using Masson-trichrome and elastic fiber staining, we observed collagen thickening and elastic fiber elongation by UA and ONA treatments. In vitro results of collagen and elastin synthesis and elastase inhibitory activity measurements were also confirmed in vivo findings. These data suggested that the effects of UA and ONA related to not only epidermal permeability barrier functions but also dermal collagen and elastic fiber synthesis. Taken together, UA and ONA can be relevant candidates to improve epidermal and dermal functions and pertinent agents for cosmeseutical applications.

Anti-oxidative and Anti-bacterial Constituents from the Extracts of Rhododendron weyrichii Leaves (참꽃나무 잎 추출물 유래 항산화 및 항균 활성 성분)

  • Kim, Jung Eun;Jo, Seong Mi;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.45 no.4
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    • pp.341-351
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    • 2019
  • In this study, we investigated anti-oxidative and anti-bacterial constituents from Rhododendron weyrichii leaves. DPPH and ABTS+ radical scavenging activities were screened for the ethanol extract and solvent fractions. Potent scavenging activities were appeared from the extract, ethyl acetate (EtOAc) and n-butanol (BuOH) fractions. Upon the anti-bacterial tests using Staphylococcus epidermidis and Propionibacterium acnes, extract, n-hexane (Hex) and EtOAc fractions showed strong activities. To isolate the active constituents, the EtOAc fraction was further purified to afford five phytochemicals; ursolic acid (1), corosolic acid (2), asiatic acid (3), astragalin (4) and isoquercetin (5). All of the compounds 1-5 were isolated for the first time from this plant. Among the isolates, the compound 4 and 5 showed strong DPPH and ABTS+ radical scavenging activities. Also, compound 3 exhibited the most potent anti-bacterial activity. In addition, the content of astragalin isolated from this plant was determined by UPLC and the quantity was about 8.1 mg/g for the 70% ethanol extract and 34.8 mg/g for the EtOAc fraction. Based on these results, it is concluded that R. weyrichii extract could be potentially applicable as anti-oxidative and anti-bacterial ingredients in cosmetic formulations.

Inhibitory Effect on TNF-${\alpha}$-Induced IL-8 Production in the HT29 Cell of Constituents from the Leaf and Stem of Weigela subsessilis

  • Thuong Phuong Thien;Jin WenYi;Lee JongPill;Seong RackSeon;Lee Young-Mi;Seong YeonHee;Song KyungSik;Bae KiHwan
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1135-1141
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    • 2005
  • Twelve compounds were isolated from the MeOH extract of the leaf and stem of the Korean endemic plant Weigela subsessilis L. H. Bailey. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. These compounds were identified as three sterols, ${\beta}$-sitosterol acetate (2), ${\beta}$-sitosterol (3), daucosterol (11), eight triterpenoids, squalene (1), ursolic acid (4), ilekudinol A (5), corosolic acid (6), ilekudinol B (7), esculentic acid (8), pomolic acid (9), asiatic acid (10), and one iridoid glycoside, alboside I (12). This is the first report pertaining to the isolation of these compounds from Weigela subsessilis L. H. Bailey. In addition, three compounds 7, 9, and 12 were found to display a strong inhibitory effect on the production of IL-8 in the HT29 cells stimulated by TNF-${\alpha}$.

A Study on the Function and Role of Morinda citrifolia L. (Noni) (노니의 기능 및 역할에 관한 연구)

  • Hwang, Hyo-Jeong;Shin, Kyung-Ok;Han, Kyoung-Sik
    • The Korean Journal of Food And Nutrition
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    • v.32 no.4
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    • pp.275-283
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    • 2019
  • This study was carried out to investigate the various roles and effects of Morinda citrifolia L.(noni) on the human body and to utilize the findings obtained for future disease related research on food and nutrition. Morinda citrifolia L. has been used in folk medicine by Polynesians for over 2,000 years and is reported to have a broad range of therapeutic effects. Noni is an alkaloid system such as proxeronine, scopoletin, octanoic acid, terpenoids, alkaloids, anthraquinones, nordamnacanthal, morindone, rubiadin, b-sitosterol, flavone glycosides, linoleic acid, acubin, L-asperuloside, caproic acid, caprylic acid, ursolic acid, rutin. Noni's side effects have been reported to affect anti-inflammatory, analgesics, LDL antioxidant, anti-tumor, antifungal, antibiotic, antiviral, antiparasitic and immunosuppressive effects. In particular, noni's efficacy is considered to be important for the prevention of diseases by inhibiting active oxygen, which is a direct cause of oxidative stress, through various metabolites through 'xeronine system'. Noni's functions and effects that have been examined in this study include anti-inflammation, pain relief, antioxidant, anticancer, hepatocyte protection among others. Therefore, noni's extracts are considered highly useful for diverse scientific and nutritional health functional foods.

Isolation of Anticancer Agents from the Leaves of Platycarya strobilacea S. et Z. (굴피나무잎으로부터 항암활성을 갖는 천연물질의 분리)

  • Kim, Yang-Il;Cho, Tai-Soon;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.27 no.3
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    • pp.238-245
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    • 1996
  • The activity guided fractionation of $CH_2Cl_2$ soluble part of Platycarya strobilacea leaves(Juglandaceae) has led to the isolation of eight active principles, identified as 5-hydroxy-2-methoxy-1,4-naphthoquinone(1), ursolic acid(2), gallic acid(3), 4,8-dihydroxynaphthalene $1-O-{\beta}-_D-glucoside(4)$, eriodictyol(5), quercetin $3-O-(2'-O-galloyl)-{\beta}-_D-glucoside(6)$. quercetin $3-O-(2'-O-galloyl)-{\beta}-_D-galactoside(7)$ and quercetin $3-O-{\alpha}-_L-rhamnoside(8)$ by the means of chemical and spectral evidence, respectively.

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Chemical constituents of Synurus deltoides (Aiton)Nakai

  • Lee, Hyun-Yong;Jin, Wen-Yi;An, Ren-Bo;Na, Min-Kyun;Bae, Ki-Hwan
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.375.2-375.2
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    • 2002
  • S.deltoides (Compositae) distributed widely in Korea. China. It is edible as a food additive. but there has been no study on chemical constituents. Therefore. we isolated nine compounds from S.deltoldes. On the basis of spectroscopic evidence. the structure of these compounds were characterized as lupeol( 1), $\alpha$-amyrin(2).$\beta$-amyrin (3), ursolic acid(4), nonacosanol(5), nonacosanoic acid(6). mixture of $\beta$-sitosterol. stigmasterol and campesterol (7), $\beta$-sitosteryl-3-O-$\beta$-D-glucopyranoside(8), stigmasteryI-3-O-$\beta$-D-glucopyranoside(9). (omitted)

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The effect of two Terpenoids, Ursolic acid and Oleanolic acid on epidermal permeability barrier and simultaneously on dermal functions

  • Lim Suk Won;Jung Sung Won;Ahn Sung Ku;Kim Bora;Ryoo Hee Chang;Lee Seung Hun
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.29 no.2 s.43
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    • pp.205-232
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    • 2003
  • Ursolic acid (UA) and Oleanolic acid (ONA), known as urson, micromerol and malol, are pentacyclic triterpenoid compounds which naturally occur in a large number of vegetarian foods, medicinal herbs, and plants. They may occur in their free acid form or as aglycones for triterpenoid saponins, which are comprised of a triterpenoid aglycone, linked to one or more sugar moieties. Therefore UA and ONA are similar in pharmacological activity. Lately scientific research, which led to the identification of UA and ONA, revealed that several pharmacological effects, such as antitumor, hepato-protective, anti-inflammatory, anticarcinogenic, antimicrobial, and anti-hyperlipidemic could be attributed to UA and ONA. Here, we introduced the effect of UA and ONA on acutely barrier disrupted and normal hairless mouse skin. To evaluate the effects of UA and ONA on epidermal permeability barrier recovery, both flanks of 8-12 week-old hairless mice were topically treated with either 0.01-0.1 mg/ml UA or 0.1-1 mg/ml ONA after tape stripping, and TEWL (Transepidermal water loss) was measured . The recovery rate increased in those UA or ONA treated groups (0.1 mg/ml UA and 0.5 mg/ml ONA) at 6 h more than $20\%$ compared to vehicle treated group (p<0.05). Here, we introduced the effects of UA and ONA on acute barrier disruption and normal epidermal permeability barrier function. For verifying the effects of UA and ONA on normal epidermal barrier, hydration and TEWL were measured for 1 and 3 weeks after UA and ONA applications (2mg/ml per day). We also investigated the features of epidermis and dermis using electron microscopy (EM) and light microscopy (LM). Both samples increased hydration compared to vehicle group from f week without TEWL alteration (p<0.005). EM examination using RuO4 and OsO4 fixation revealed that secretion and numbers of lamellar bodies and complete formation of lipid bilayers were most prominent $(ONA{\geq}UA>Vehicle)$. LM finding showed that thickness of stratum corneum (SC) was slightly increased and especially epidermal thickening and flattening was observed (UA>ONA>Veh). We also observed that UA and ONA stimulate epidermal keratinocyte differentiation via $PPAR\;\alpha$. Protein expression of involucrin, loricrin, and filaggrin increased at least 2 and 3 fold in HaCaT cells treated with either $ONA\;(10{\mu}M)$ or UA $(10{\mu}M)$ for 24h respectively. This result suggested that the UA and ONA can improve epidermal permeability barrier function and induce the epidermal keratinocyte differentiation via $PPAR\;{\alpha}$. Using Masson-trichrome and elastic fiber staining, we observed collagen thickening and elastic fiber elongation by UA and ONA treatments. In vitro results of collagen and elastin synthesis and elastase inhibitory activity measurements were also confirmed in vivo findings. These data suggested that the effects of UA and ONA related to not only epidermal permeability barrier functions but also dermal collagen and elastic fiber synthesis. Taken together, UA and ONA can be relevant candidates to improve epidermal and dermal functions and pertinent agents for cosmeseutical applications.