• 제목/요약/키워드: synthesis of natural product

검색결과 124건 처리시간 0.032초

Melanin Inhibitory Effect of Tuber himalayense Isolated in Incheon, Korea

  • Byeong Min Choi;Minkyeong Kim;Hyehyun Hong;Tae-Jin Park;Changmu Kim;Jin-Soo Park;Won-Jae Chi;Seung-Young Kim
    • Journal of Microbiology and Biotechnology
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    • 제34권4호
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    • pp.949-957
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    • 2024
  • There has been a growing interest in skin beauty and antimelanogenic products. Melanogenesis is the process of melanin synthesis whereby melanocytes are activated by UV light or hormone stimulation to produce melanin. Melanogenesis is mediated by several enzymes, such as tyrosinase (TYR), microphthalmia-associated transcription factor (MITF), tyrosinase-related protein-1 (TRP-1), and TRP-2. In this study, we investigated the effect of Tuber himalayense extract on melanin synthesis in α-melanocyte-stimulating hormone (α-MSH)-treated B16F10 melanoma cells. We confirmed that T. himalayense extract was not toxic to α-MSH-treated B16F10 melanoma cells and exhibited a significant inhibitory effect on melanin synthesis at concentrations of 25, 50, and 100 ㎍/ml. Additionally, the T. himalayense extract inhibited melanin, TRP-1, TRP-2, tyrosinase, and MITF, which are enzymes involved in melanin synthesis, in a concentration-dependent manner. Furthermore, T. himalayense extract inhibited the mitogen-activated protein kinase (MAPK) pathways, such as extracellular signal-regulated kinase-1/2 (ERK), c-Jun N-terminal kinase (JNK), and p38. Therefore, we hypothesized that various components of T. himalayense extract affect multiple factors involved in melanogenesis in B16F10 cells. Our results indicate that T. himalayense extract could potentially be used as a new material for preparing whitening cosmetics.

Tyrosinase Inhibitory Constituents of Morus bombycis Cortex

  • Kang, Kyo-Bin;Kim, Sang-Du;Kim, Tae-Bum;Jeong, Eun-Ju;Kim, Young-Choong;Sung, Jong-Hyuk;Sung, Sang-Hyun
    • Natural Product Sciences
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    • 제17권3호
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    • pp.198-201
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    • 2011
  • Tyrosinase is one of the important enzymes in the mammalian melanin synthesis. In the process of melanin synthesis, tyrosine is oxidized to DOPA (3,4-dihydroxyphenylalanine), and DOPA is further oxidized to dopaquinone. Tyrosinase is an enzyme catalyzing this oxidation of tyrosine, so chemicals that inhibit the activity of tyrosinase can be used as skin whitening agents. In this study, we isolated five constituents from the 80% MeOH extract of Morus bombycis cortex by bioactivity-guided fractionation. We performed mushroom tyrosinase inhibition assay. As a result, 7,2',4'-trihydroxyflavanone (1), 2',4',2,4,-tetrahydroxychalcone (2), and oxyresveratrol (3) showed the more potent inhibitory effect compared to kojic acid, a well-known skin whitening agent with antityrosinase effect. Moracinoside M (4) and moracin M-3'-O-${\beta}$-D-glucopyranoside (5) also showed the moderate tyrosinase inhibitory activities.

Identification of a Polyketide Synthase Gene in the Synthesis of Phleichrome of the Phytopathogenic Fungus Cladosporium phlei

  • So, Kum-Kang;Chung, Yun-Jo;Kim, Jung-Mi;Kim, Beom-Tae;Park, Seung-Moon;Kim, Dae-Hyuk
    • Molecules and Cells
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    • 제38권12호
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    • pp.1105-1110
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    • 2015
  • Phleichrome, a pigment produced by the phytopathogenic fungus Cladosporium phlei, is a fungal perylenequinone whose photodynamic activity has been studied intensively. To determine the biological function of phleichrome and to engineer a strain with enhanced production of phleichrome, we identified the gene responsible for the synthesis of phleichrome. Structural comparison of phleichrome with other fungal perylenequinones suggested that phleichrome is synthesized via polyketide pathway. We recently identified four different polyketide synthase (PKS) genes encompassing three major clades of fungal PKSs that differ with respect to reducing conditions for the polyketide product. Based on in silico analysis of cloned genes, we hypothesized that the non-reducing PKS gene, Cppks1, is involved in phleichrome biosynthesis. Increased accumulation of Cppks1 transcript was observed in response to supplementation with the application of synthetic inducer cyclo-(${_L}-Pro-{_L}-Phe$). In addition, heterologous expression of the Cppks1 gene in Cryphonectria parasitica resulted in the production of phleichrome. These results provide convincing evidence that the Cppks1 gene is responsible for the biosynthesis of phleichrome.

Chemical Constituents from Artemisia iwayomogi Increase the Function of Osteoblastic MC3T3-E1 Cells

  • Ding, Yan;Liang, Chun;Choi, Eun-Mi;Ra, Jeong-Chan;Kim, Young-Ho
    • Natural Product Sciences
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    • 제15권4호
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    • pp.192-197
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    • 2009
  • Chemical investigation of the aerial parts of Artemisia iwayomogi has afforded five glycoside compounds. Their chemical structures were characterized by spectroscopic methods to be turpinionoside A (1), (Z)-3-hexenyl O-${\alpha}$-arabinopyranosyl-(1${\rightarrow}$6)-O-${\beta}$-D-glucopyranoside (2), (Z)-5'-hydroxyjasmone 5'-O-${\beta}$-Dglucopyranoside (3), (-)-syringaresinol-4-O-${\beta}$-D-glucopyranoside (4), and methyl 3,5-di-O-caffeoyl quinate (5). All of them were isolated for the first time from Artemisia species. The effect of compounds 1 - 5 on the function of osteoblastic MC3T3-E1 cells was examined by checking the cell viability, alkaline phosphatase (ALP) activity, collagen synthesis, and mineralization. Turpinionoside A (1) significantly increased the function of osteoblastic MC3T3-E1 cells. Cell viability, ALP activity, collagen synthesis, and mineralization were increased up to 117.2% (2 ${\mu}M$), 110.7% (0.4 ${\mu}M$), 156.0% (0.4 ${\mu}M$), and 143.0 % (2 ${\mu}M$), respectively.

Plant genome analysis using flow cytometry

  • 이재헌;김기영;정대수;정원복;권오창
    • 한국작물학회:학술대회논문집
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    • 한국작물학회 1999년도 춘계 학술대회지
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    • pp.162-163
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    • 1999
  • The goal of this research was (1) to describe the conditions and parameters required for the cell cycle synchronization and the accumulation of large number of metaphase cells in maize and other cereal root tips, (2) to isolate intact metaphase chromosomes from root tips suitable for characterization by flow cytometry, and (3) to construct chromosome-specific libraries from maize. Plant metaphase chromosomes have been successfully synchronized and isolated from many cereal root-tips. DNA synthesis inhibitor (hydroxyurea) was used to synchronize cell cycle, follwed by treatement with trifluralin to accumulate metaphase chromosomes. Maize flow karyotypes show substantial variation among inbred lines. thish variation should be sueful in isolating individual chromosome types. In addition, flow cytometry is a useful method to measure DNA content of individual chromosomes in a genotyps, and to detect chromosomal variations. Individual chromosome peaks have been sorted from the maize hybrid B73/Mol7. Libraries were generated form the DOP-PCR amplification product from each peak. To date, we have analyzed clones from a library constructed from the maize chromosome 1 peak. Hybridization of labeled genomic DNA to clone inserts indicated that $24\%,\;18\%,\;and\;58\%$ of the clones were highly repetitive, medium repetitive, and low copy, respectively. Fifty percent of putative low cpoy clones showed single bands on inbred screening, blots, and the remaining $50\%$ were low copy repeats. Single copy clones showing polymorphism will be mapped using recombinant inbred mapping populations. Repetitive clones are being characterized by Southern blot analysis, and will be screened by in situ hybridization for their potential utility as chromosome specific markers.

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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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    • 제22권3호
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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.

A Stereoselective Synthesis of (Z,Z)-3,13-Octadecadien-1-yl Acetate, and Its (E,Z)-Isomer, the Sex Pheromone of the Cherry Tree Borer, Synanthedon hector Butler

  • Kang, Suk-Ku;Park, Sun-Ku
    • Bulletin of the Korean Chemical Society
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    • 제9권3호
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    • pp.149-152
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    • 1988
  • A mixture of (Z,Z)-3,13-octadecadien-1-yl acetate(1) and its (E,Z)-isomer(2), the sex pheromone of the cherry tree borer, Synanthedon hector Butler was synthesized. (Z)-11-Octadecen-1-al(3) was prepared from 1,10-decandiol. The Wittig reaction the above aldehyde3 with carboethoxymethylenetriphenylphosphorane, or the Wadsworth-Emmons reaction of the above aldehyde3 with the anion of triethylphosphonoacetate gave ethyl (Z,Z)-2,13-octadecadienoate and its (E,Z)-isomer. Deconjugative protonation of ethyl (Z,Z)-2,13-octadecadienoate and its (E,Z)-isomer with potassium hexamethyldisilazide followed by aqueous ammonium chloride work-up afforded stereoselectiv디y ethyl (E,Z)-3,13-octadecadienoate and its (Z,Z)-isomer, respectively, of which stereoselectivity was adjusted to give the product in the required ratio. Exposure of the above deconjugated ester to excess lithium aluminium hydride resulted in formation of the penultimate (Z,Z)-3,13-octadecadien-1-ol and its (E,Z)-isomer. Acetylation of the desired alcohols afford the final products, (Z,Z)-3,13-octadecadien-1-yl acetate(1) and its (E,Z)-isomer(2).

Effects of Hahella chejuensis-Derived Prodigiosin on UV-Induced ROS Production, Inflammation and Cytotoxicity in HaCaT Human Skin Keratinocytes

  • Lee, Jieun;Kim, Hyun Ju;Lee, Sang Jun;Lee, Moo-Seung
    • Journal of Microbiology and Biotechnology
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    • 제31권3호
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    • pp.475-482
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    • 2021
  • Prodigiosins, which are natural tripyrrole red pigments and synthetic derivatives, reportedly have multiple biological effects mainly on various types of cancer cells. However, the effects of bacterial prodigiosin on non-cancerous HaCaT human skin keratinocytes have not been reported. Therefore, the present study aimed to investigate the functional activities of prodigiosin derived from cultures of the bacterium Hahella chejuensis in HaCaT cells. Cell viability, the cell proliferation rate, and reactive oxygen species (ROS) production in vitro were assayed following treatment of HaCaT cells with prodigiosin. Prodigiosin did not cause cytotoxicity and notably increased proliferation of HaCaT cells. Furthermore, prodigiosin reduced ultraviolet (UV) irradiation-induced ROS production and the inflammatory response in HaCaT cells. More importantly, prodigiosin reduced matrix metalloproteinase-9 expression and increased collagen synthesis in UV-irradiated HaCaT cells, demonstrating that it elicits anti-aging effects. In conclusion, our results reveal that H. chejuensis-derived prodigiosin is a potential natural product to develop functional cosmetic ingredients.

Synthesis of new apicidin derivatives as Histone deacetylase(HDAC) inhibitors

  • H.O. Kang;C.H. Jin;J.W. Han;Lee, H.W.;Lee, Y.W.;Park, H.J.;O.P. Zee;Y.H. Jung
    • 한국응용약물학회:학술대회논문집
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    • 한국응용약물학회 2001년도 추계학술대회 및 정기총회
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    • pp.110-110
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    • 2001
  • Histone deacetylase(HDAC), a neuclear enzyme that regulates gene trascription and the assembly of newly synthesized chromatin, has received much attention in recent literature. The explosion of activity in this field has yielded the cloning of a mammalian gene which encodes a complementary histone acetyl trasferases. Several cyclic tetrapeptide inhibitors of HDAC has been reported to affect the hyperacetylation of mammalian and plant histones. Apicidin, a natural product HDAC inhibitor recently isolated at Merck Research Laboratories, induces therapeutic applications as a broad spectrum antiprotozoal agent to multi-drug resistant malaria and a potential antitumor agnet. The biological activity of apicidin appears to be attributable to inhibition of apicocomplexan HDAC at low nanomolar concentrations.

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Regio- and Stereoselective Reactions of (S)-(1-Methylpyrrolidin-2-yl)methyl Allyl Sulfide

  • Park, Ho-Koon;Baik, Nam-Hoon;Lee, Jae-Yeol;Kim, Soo-Ja;Ham, Won-Hoon
    • Archives of Pharmacal Research
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    • 제14권4호
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    • pp.364-369
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    • 1991
  • The synthesis and regioselective reactions of a chiral allyl sulfide. (S)-(+)-(1-methylpyrrolidin-2-yl)methyl allyl sulfide (MAS, 1) are described. Remarkable ${\alpha}-regioselectivity$ was observed in the alkylation of the carbanion of MAS while 1:3 mixtures of ${\alpha}-and\;{\gamma}-adducts$ were produced in the addition of the MAS anion to aldehydes. However, a dramatic change of the regioselectivity was witnessed when Lewis acids such as $Et_3Al$, $Et_3B$, and $Ti(O^iPr)_4$ were used as additives in the addition reaction. In these cases, ${\alpha}-adducts$ were formed exclusively. A rationale for the change of regioselectivity is provided. And the stereochemical aspect of the addition reaction is also described.

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