• Title/Summary/Keyword: squalene

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Isolation and Identification of Secondary Metabolites from the Ovary of Nelumbo nucifera (연꽃 자방으로부터 이차대사물질 분리 및 구조동정)

  • Ji, Seung-Heon;Lee, Jae-Won;Lee, Seung-Eun;Lee, Young-Seob;Kim, Geum-Soog;Ahn, Young-Sup;Baek, Nam-In;Lee, Yi;Lim, Heung-Bin;Lee, Dae Young
    • Journal of Life Science
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    • v.26 no.10
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    • pp.1196-1201
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    • 2016
  • The ovary parts of Nelumbo nucifera were extracted in 80% methanol (MeOH), and the concentrated extract was then partitioned using n-hexane, ethyl acetate (EtOAc), n-butanol (n-BuOH), and H2O, successively. Using an octadecyl silica gel (ODS) column, silica gel (SiO2) column chromatography, and a HPLC purification system, five compounds were isolated from the n-hexane fraction obtained from the extract of N. nucifera ovary. The chemical structures of the metabolites were determined using several spectroscopic methods, including NMR and GC/MS and MS of 1-eicosanol (1), cycloartenol (2), trans-squalene (3), pentadecanoic acid (4), and β-sitosterol (5). This study is a first attempt to isolate and identify secondary metabolites from the ovary of N. nucifera. The results indicated that the extract of N. nucifera ovary has biological effects, such as antibacterial and -tumor activity. Therefore, it could decrease the risk of HIV transmission through breastfeeding.

The Functionalities and Active Constituents of Olive Oil (올리브유의 기능성과 활성성분)

  • Heo, Wan;Lee, So Yoon;Lim, Su-Young;Pan, Jeong Hoon;Kim, Hyung Min;Kim, Young Jun
    • Korean Journal of Food Science and Technology
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    • v.44 no.5
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    • pp.526-531
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    • 2012
  • Olive oil is widely consumed in Korea, and is a representative fat source in the Mediterranean diet, known to be effective in the prevention of coronary artery disease. In addition, diverse functionalities have been reported, such as anti-cancer, anti-oxidation, and anti-inflammation effects. In this review, the status of production and variety were investigated with respect to the functionalities of olive oil. The main functional constituents of olive oil are oleic acid, known to improve blood cholesterol, and the minor constituents are polyphenol, tocopherol, squalene, and phospholipid, the concentrations of which can be used to distinguish pressed from refined olive oil. A number of studies of the functionality of olive oil have dealt with the minor constituents, and the beneficial functionalities, such as anti-oxidation, anti-inflammation, and improving blood circulation have been reported. This review intensively investigates the functionalities and the responsible components, and suggests that continual studies on olive oil are necessary for the prevention of various metabolic diseases.

Alleviative Effects of Jujube Water Extract on the Inflammation and Barrier Damage in Hairless Mice Skin (Hairless 마우스에서 대추 열수추출물의 피부내 염증 및 장벽 손상 완화 효과)

  • Choi, So-Young;Kim, Young-Chul
    • Environmental Analysis Health and Toxicology
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    • v.24 no.4
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    • pp.351-357
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    • 2009
  • To investigate the alleviative effects of jujube water extract (JWE) on the inflammation and skin barrier damage, both the irradiation of UVB and the application of squalene monohydroperoxide (Sq-OOH) were applied to the back skin of experimental animals for 4 weeks. And at the same time experimental materials were applied topically. Six weeks female SKH-1 hairless mice were divided into five groups (five animals for each group) including normal (N; saline), control (C; UVB+Sq-OOH+saline), vehicle control (VC; UVB+Sq-OOH+vehicle), positive control (PC; UVB+Sq-OOH+0.01% retinoic acid) and experimental (E; UVB+Sq-OOH+JWE) groups. The skin erythema index in the E group was significantly low compared to the C group (p<0.05). Lipid (p<0.05) and water (p<0.01) capacities in the E group were significantly high compared to the C group. In comparison with the C group, E group showed a relatively well preserved lipid lamellae in the epidermis and a relatively much less infiltration of mast cells in the dermis or hypodermis. As for the both absolute and relative weights of the spleen, PC group were significantly higher than the other groups. These results suggest that JWE have a considerably inhibitory effect on the inflammation and the skin barrier damage induced by UVB irradiation and Sq-OOH application.

Anti-inflammatory Compounds from the Leaves of Ailanthus altissima Meihua JIN

  • Jin, Me-Ihua;Bae, Ki-Hwan;Chang, Hyeun-Wook;Son, Jong-Keun
    • Biomolecules & Therapeutics
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    • v.17 no.1
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    • pp.86-91
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    • 2009
  • In our ongoing search for biological components from the Korea endemic plants, the MeOH extract of Ailanthus altissima leaves (Simaroubaceae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2$ ($PGD_2$) and leukotriene $C_4$ ($LTC_4$) in mouse bone marrow-derived mast cells (BMMCs). In further study, eight compounds, squalene (1), ${\beta}$-sitosterol (2), scopoletin (3), quercetin (4), luteolin (5), astragalin (6), scopolin (7), and daucosterol (8) were isolated, the chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. Among the compounds, 2, 4, and 5 strongly inhibited both the COX-2-dependent PGD2 generation with $IC_{50}$ values of 2.6, 7.3 and 2.5 ${\mu}M$, respectively and the generation of $LTC_4$ in the 5-LOX dependent phase with $IC_{50}$ values of 2.0, 5.1 and 1.8 ${\mu}M$, respectively, which suggest that the anti-inflammatory activity of A. altissima might occur in part via the inhibition of both $PGD_2$ and $LTC_4$ generation by 2, 4 and 5.

Topoisomerase I and II Inhibitory Activities and Cytotoxic Constituents from the Barks of Tilia amurnesis

  • Piao, Dong Gen;Lee, You-Jeong;Seo, Chang-Seob;Lee, Chong-Soon;Kim, Jae-Ryong;Chang, Hyun-Wook;Son, Jong-Keun
    • Natural Product Sciences
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    • v.17 no.3
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    • pp.245-249
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    • 2011
  • Eight compounds, squalene (1), friedelin (2), ${\beta}$-sitosterol (3), ${\beta}$-sitosterol-3-O-glucoside (4), ${\alpha}$-tocopherol (5), betulinic acid (6), trilinolein (7) and 1-O-(9Z,12Z-Octadecadienoyl)-3-nonadecanoyl glycerol (8), were isolated from the barks of Tilia amurensis. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in the literature. These isolated compounds were examined for their inhibitory activities against topoisomerase I and II. Compound 7 showed significant inhibition of DNA topoisomerase I and II activities, with percent decreases in activity of 87 and 95%, respectively at a concentration of $100\;{\mu}M$. Compound 6 exhibited cytotoxicity against the human colon adenocarcinoma cell line (HT-29), the human breast adenocarcinoma cell line (MCF-7) and the human liver hepatoblastoma cell line (HepG-2), with $IC_{50}$ values of 20, 59 and $16\;{\mu}M$, respectively.

Modulation of Melanin Synthesis by Amaranthus spp. L Seed Extract in Melan-a Cells

  • Seo, Jae Ok;Do, Moon Ho;Lee, Jae Hak;Lee, Taek Hwan;Wahedi, Hussain Mustatab;Park, Yong Un;Kim, Sun Yeou
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.168-174
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    • 2016
  • Anti-melanogenic effects of amaranth (AT), one of the key source of squalene, were investigated in melanocytes. Amaranth seed powder was extracted with water and melan-a cells were treated with various concentrations of AT. By using HPLC, content of myo-inositol, one of potential active components, was measured in the crude extract of AT.AT reduced the melanin content in melan-a melanocytes and down-regulated melanogenic enzyme activity such as tyrosinase, TRP-1 and TRP-2. By regulating melanogenic enzyme activity, AT may be a potential natural source for whitening agent. Myo-inositol was detected in AT by HPLC and may be one of the active compounds from AT involved in the regulation of anti-melanogenesis. In this study, we demonstrated that AT has anti-melanogenesis properties. This new function of amaranth may be useful in the development of new skin-whitening products and its value as food.

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-${\alpha}$.

Effects of Precursor and Thidiazuron on Triterpene Saponin Biosynthesis in Centella asiatica (L.) Urban

  • Kim, Ok-Tae;Kim, Min-Young;Ahn, Jun-Cheul;Li, Mei-Yang;Hwang, Baik
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.2
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    • pp.91-94
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    • 2005
  • Plants have been known to accumulate a very diverse range of triterpene saponins. We have investigated the regulation of saponin biosynthesis in higher plants using Centella asiatica (L.) Urban as a model plant. Effects of a feeding precursor on asiaticoside production from leaves and on the level of two-type OSCs mRNA were investigated. As a feeding precursor, squalene negatively affected the levels of CYS and bAS mRNA, but it also decreased the production of asiaticoside from whole plants. Plant hormones regulate secondary metabolism, and in plant tissue cultures they could affect both culture growth and secondary metabolite production. Although enhancement of asiaticoside production from whole plant cultures by addition of TDZ (thidiazuron) has been reported, the positive effect of TDZ on the levels of OSCs transcripts was not observed.

The Metabolism of (2-$^{14}C$) Mevalonic Acid on Photoperiodic Induction in Grafted Solanum Andigena

  • Bae, Moo;Mercer, E.I.
    • Nuclear Engineering and Technology
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    • v.2 no.2
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    • pp.73-84
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    • 1970
  • The metabolism of sterol precurosor in leaves of Salanum andigena grafted between photoinduced and noninduced plant was investigated with the use of (2-$^{14}$ C) mevalonic acid. By the technique of the preparative gas-liquid chromatography, radioactive compounds of squalene, 4,4’-dimethylsterols and 4-demethylsterol were isolated and determined quantitatively. When labeled mevalonic acid n as applied to leaves radioactivity was extensively incorporated into non-saponifiable materials of lipid fraction and aqueous fraction (ethanol-water fraction). Radioactivity of 14C derived from (2-$^{14}$ C) mevalonic acid was transmissible from photoinduced plant to non-induced plant across the graft union, as tuberization hormone was, and incorporated into the sterols of the non-induced plant. Inhibitors of sterol biosynthesis, SK & F 7997 and nicotinic acid, are effective suppressors of tuber growing, if applied to leaves during photoinduction period. The experimental results suggest that certain substance containing isoprene unit, or sterol-like compound may participate in tuber growing.

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Upregulation of Isoprenoid Pathway Genes During Enhanced Saikosaponin Biosynthesis in the Hairy Roots of Bupleurum falcatum

  • Kim, Young Soon;Cho, Jung Hyun;Ahn, Juncheul;Hwang, Baik
    • Molecules and Cells
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    • v.22 no.3
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    • pp.269-274
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    • 2006
  • In order to characterize saikosaponin biosynthesis in Bupleurum falcatum, the expression of five isoprenoid pathway genes and their relationship to saikosaponin accumulation in the hairy roots were analyzed. The hairy roots exhibited a rapid accumulation of saikosaponins when incubated in a root culture medium (3XRCM). Homology-based RT-PCR was used to isolate core fragments of five genes, HMGR, IPPI, FPS, SS, and OSC, from the hairy roots. The deduced amino acid sequences exhibited amino acid identities of more than 85% to previously reported genes. Using the fragments as probes, the expression of these five genes in the hairy roots during incubation in 3XRCM medium was examined. Expression of all five genes in the hairy roots increased soon after incubation. In particular, the SS and OSC genes were coordinately induced at 8 days of incubation, and their expression persisted throughout the incubation period. A quantitative HPLC analysis showed that the saikosaponin content of the hairy root culture also began to increase at 8 days of culture. The correlation between SS transcript level and saikosaponin content in the hairy roots suggests that transcriptional regulation plays a regulatory role in saikosaponin biosynthesis.