• Title/Summary/Keyword: Corosolic acid

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Structure Determination of a New Lupane-type Triterpene, Tiarellic Acid, Isolated from Tiarella polyphylla

  • Lee, Hyeong-Kyu;Park, Si-Hyung;Oh, Sei-Ryang;Ahn, Kyung-Seop;Kim, Jae-Gil
    • Archives of Pharmacal Research
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    • v.25 no.1
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    • pp.57-60
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    • 2002
  • A new 27-carboxylic lupane-type triterpene, tiarellic acid (1), was isolated from Tiarella polyphylla together with corosolic acid (2) and tormentic acid (3). Tiarellic acid was characterized as 3,23-dihydroxy-20(29)-lupen-27-oic acid and its NMR data were unambiguously assigned using 2-D NMR techniques.

Isolation and Identification of Triterpenoids and Sterols from the Flowers of Chionanthus retusus Lindl. & Paxton (이팝나무(Chionanthus retusus Lindl. & Paxton) 꽃으로부터 Triterpenoid 및 Sterol 화합물의 분리 및 동정)

  • Jung, Jae-Woo;Seo, Kyeong-Hwa;Oh, Eun-Ji;Lee, Dae-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.3
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    • pp.237-240
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    • 2015
  • The flowers of Chionanthus retusus Lindl. & Paxton were extracted with 80% aqueous MeOH at room temperature. The concentrated extract was partitioned as EtOAc, n-BuOH, and $H_2O$ fractions. From the EtOAc fraction, two triterpenoids and two sterols were isolated using the repeated silica gel ($SiO_2$) and octadecyl $SiO_2$ (ODS) column chromatographies. According to the results of physico-chemical and spectroscopic data including nuclear magnetic resonance, mass spectrometry, and infrared. The chemical structures of the compounds were respectively determined as ursolic acid (1), corosolic acid (2), ${\beta}$-sitosterol (3), and daucosterol (4). All the compounds were isolated for the first time from the flowers of Chionanthus retusus Lindl. & Paxton.

Triterpenes from Perilla frutescens var. acuta and Their Cytotoxic Activity

  • Woo, Kyeong Wan;Han, Ji Young;Choi, Sang Un;Kim, Ki Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.71-75
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    • 2014
  • Nine triterpenes were isolated from the petroleum ether and MeOH extract of Perilla frutescens var. acuta leaves. Their structures were determined to be arjunic acid (1), maslinic acid (2), oleanolic acid (3), euscaphic acid (4), tormentic acid (5), 3-O-trans-p-coumaroyltormentic acid (6), 28-formyloxy-$3{\beta}$-hydroxy-urs-12-ene (7), ursolic acid (8), and corosolic acid (9) by spectroscopic methods. The compounds 1, 2, 4, 6, and 7 were isolated for the first time from this plant and the Genus Labiatae. The isolated compounds (1-9) were tested for cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) in vitro using a Sulforhodamin B bioassay.

Ursane-Type Triterpenoids from the Aerial Parts of Potentilla discolor

  • Jang, Dae-Sik;Kim, Jong-Min;Lee, Ga-Young;Kim, Joo-Hwan;Kim, Jin-Sook
    • Journal of Applied Biological Chemistry
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    • v.49 no.2
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    • pp.48-50
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    • 2006
  • Four ursane-type triterpenoids, ursolic acid (1), 23-hydroxyursolic acid (2), corosolic acid (3), and tormentic acid (4), and a phytosterol, ${\beta}-sitosterol-3-O-{\beta}-D-glucoside$, were isolated from an EtOAcsoluble extract of the aerial parts of Potentilla discolor. The structures of 1-4 were identified by spectroscopic methods, particularly by extensive NMR studies. This is the first report on the isolation of compounds 1-4 from this plant.

Chemicals Constituents from Leaves of Diospyros iturensis (Gürke) Letouzey & F. White and their Biological Activities

  • Feusso, Hermann Marius Feumo;Dongmo, Jean de dieu;Djomkam, Hermine Laure Maza;Akak, Carine Mvot;Lateef, Mehreen;Ahmed, Ayaz;Azebaze, Anatole Guy Blaise;Waffo, Alain Francois Kamdem;Ali, Muhammad Shaiq;Vardamides, Juliette Catherine
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.311-316
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    • 2020
  • The chemical investigation of the methanolic crude extract of leaves of Diospyros iturensis gave us 15 known secondary metabolites identified as mixture of α-amyrenone (1) and β-amyrenone (2), β-amyrin (3), mixture of β-sitosterol (4) and stigmasterol (5), betulin (6), uvaol (7), betulinic acid (8), ursolic acid (9), corosolic acid (10), actinidic acid (11),11-O-p-hydroxybenzoylbergenin (12), bergenin (13) and mixture of stigmasterol glucoside (14) and β-sitosterol glucoside (15) respectively. The structures of secondary metabolites were elucidated with the help of NMR and mass spectral data and by comparison of their spectral data with literature. Among the fifteen isolated compounds, four compounds were identified for the first time in Diospyros genus. These included uvaol (7), corosolic acid (10), actinidic acid (11) and 11-O-p-hydroxybenzoylbergenin (12). Crude methanolic extract of leaves and four isolated compounds including betulin (6), betulinic acid (8), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) were evaluated for their antiproliferative activity against two cancer cell lines CAL-27 and NCI-H460 by the MTT assay, antioxidant potential and inhibitory activity against the lipoxygenase and urease enzymes, respectively. The results indicated that the methanolic crude extract of leaves exhibited moderate antioxidant activity and was inactive against the two cancer cell lines. Betulin (6), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate antioxidant and lipoxygenase inhibition with IC50 = 65.8, 85.6, 82.5 μM and IC50 = 58.5, 95.2, 76.2 μM, respectively. Furthermore, 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate urease inhibition activity with IC50 values of 45.6 μM and 49.8 μM, respectively.

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.

Comparison of Chemicals in Lagerstroemia speciosa (L.) Pers. at Growing Stage Levels by GC-MS

  • Choi, Joo-Soo;Ku, Pyung-Tae;Cho, Kyung-Soon;Huh, Man-Kyu
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.55 no.3
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    • pp.200-206
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    • 2010
  • Banaba, Lagerstroemia speciosa (L.) Pers. (Lythraceae) is a tree that grows in the tropic islands of the Pacific. This plants are used for medical purposes in the world. The components of L. speciosa were analyzed for the contents according to growing stages at leaves. The distributions of the corosolic acid ($2{\alpha}$, $3{\beta}$-dihydroxyurs-12-en-28-oic acid), phytol, campestrol, and vitamin E were rich among samples in this study. These were contained much fatty acids. The mean content of palmitic acid was from 2.4% across all growing stages, varying from 2.15% for young leaves with the lowest content and 2.86% for fallen leaves with the highest content. Oleic acid, linoleic acid, and linolenic acid were contained nearly mean 2.0% in all leaves of banaba. Our results have shown that the phytochemical profile of young L. speciosa leaves differs quite radically from that of old L. speciosa leaves. In addition, these subdividing results according to plant growth should allow future researches to conduct targeted experimental studies and use of particular medical components of interest, examining chemical variation on the inter-developmental levels.

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-${\alpha}$.

Anti-diabetic Effects of Banaba Leaf Extracts (Lagerstroemia speciosa Pers.) through Solvents (추출용매 변화에 따른 바나바(Lagerstroemia speciosa Pers.) 잎 추출물의 항당뇨 효과)

  • Kim, Kyun-Ha;Roh, Sang-Geun;Li, Chun-Ri;Jin, Chun-Feng;Kim, Andre;Choi, Won-Chul
    • Journal of Life Science
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    • v.18 no.9
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    • pp.1305-1311
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    • 2008
  • This study investigated that the antidiabetic effects of banaba extracts with variety solvents selectivity in vitro and in vivo. Banaba extracts were prepared with water, 70% ethanol, 90% ethanol, 100% ethanol and water-ethanol that of extract twice times sequentially water and ethanol. Cell toxicity and insulin secretion of banaba extracts was tested by MTT (3-[4,5-dimetylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) assay on hamster insulinoma cell line, HIT-T15. Also we tested that insulin, body weight, blood glucose, total cholesterol, HDL-cholesterol, triglyceride and free fatty acid in streptozotocin diabetic rats. Water-ethanol extract has remarkable antidiabetic effect compare with the other banaba extracts. For water-ethanol extract has both of hydrophilic and hydrophobic antidiabetic materials from banaba. Expecially, corosolic acid, as known as unique polyphenol, has antidiabetic effect studied by many researchers till nowadays. But corosolic acid does not solve in water. Otherwise, we suggest that banaba extract of hydrophilic and hydrophobic materials (polyphenol and antioxidants) mixture more increased antidiabetic effects.

Anti-inflammatory and Anti-bacterial Active Ingredients Derived from the Extract of the Leaves of Hydrangea Petiolaris (등수국 잎 추출물 유래 항염 및 항균 활성 성분)

  • Jo, Seong Mi;Kim, Jung Eun;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.46 no.3
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    • pp.207-218
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    • 2020
  • In this study, the anti-inflammatory and anti-bacterial activities of the extracts from the leaves of the Hydrangea petiolaris were identified, and the chemical structure was identified by separating the active ingredient. As the result of the anti-inflammatory activity experiment using RAW 264.7 cells, it was confirmed that the n-hexane (Hex) and ethyl acetate (EtOAc) fractions inhibited the production of nitric oxide (NO) and the expression of iNOS protein in a concentration-dependent manner without cytotoxicity. In addition, the n-Hex and EtOAc fractions reduced the production of pro-inflammatory cytokines (TNF-α, IL-1β and IL-6). Upon the anti-bacterial tests using Staphylococcus epidermidis and Cutibacterium acnes, the extract, n-Hex, EtOAc and n-butanol (BuOH) fractions showed potent activities. In order to isolate the active constituents, the n-Hex and EtOAc fractions were further purified to afford four phytochemicals; phytol (1), corosolic acid (2), asiatic acid (3) and 1-O-p-coumaroyl-β-D-glucopyranoside (4). All of the compounds 1 - 4 were isolated for the first time from this plant. In addition, the contents of isolated compounds were determined by HPLC and the quantity of phytol (1) was 27.8 mg/g for the 70% EtOH extract. Based on the above research results, it is believed that it will be possible to develop a natural cosmetic material that has anti-inflammatory and anti-bacterial effects using the extract of H. petiolaris leaves.