• Title/Summary/Keyword: synthesis of natural product

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Antaroide, a Novel Natural Nine-Membered Macrolide, Inhibits Melanin Biosynthesis in B16F10 Murine Melanoma Cells

  • Ryu, Min-Ji;Baek, Eun-Ki;Kim, Soyeon;Seong, Chi Nam;Yang, Inho;Lim, Kyung-Min;Nam, Sang-Jip
    • Biomolecules & Therapeutics
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    • v.29 no.1
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    • pp.98-103
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    • 2021
  • The demand for natural substances with anti-melanogenic activity is increasing due to the recent interest in skin whitening. Intensive investigation on the culture broth of Streptomyces sp. SCO-736, a marine bacterium from the Antarctica coast, has led to the isolation of a new natural product named antaroide (1). The chemical structure was established through the interpretation of MS, UV, and NMR spectroscopic data. Antaroide is a nine-membered macrolide with lactone and lactam moieties. To investigate its applicability in skin whitening cosmetics, its anti-melanogenic activity in B16F10 murine melanoma cells was examined. As a result, antaroide displayed strong inhibitory activities against melanin synthesis and also attenuated the dendrite formation induced by the α-melanocyte stimulating hormone (α-MSH). Antaroide suppressed the mRNA expression of the melanogenic enzymes such as tyrosinase, TRP-1 and TRP-2. This suggests that it may serve as a transcriptional regulator of melanogenesis. Collectively, the discovery of this novel natural nine-membered macrolide and its anti-melanogenic activity could give new insights for the development of skin whitening agents.

Butein Disrupts Hsp90's Molecular Chaperoning Function and Exhibits Anti-proliferative Effects Against Drug-resistant Cancer Cells

  • Seo, Young Ho
    • Bulletin of the Korean Chemical Society
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    • v.34 no.11
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    • pp.3345-3349
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    • 2013
  • Hsp90 shows great promise as a therapeutic target due to its potential to disable multiple signaling pathways simultaneously. In this study, we discovered that a natural product, butein moderately inhibited the growth of drug-resistant cancer cells (A2780cis and H1975), and brought about the degradation of oncogenic Hsp90 client proteins. The study demonstrated that butein would be a therapeutic lead to circumvent drug-resistance in cancer chemotherapy. The structure-based screening, synthesis, and biological evaluation of butein are described herein.

Approach to the Total Synthesis of Acanthoside-D

  • Ngoc, Thyen-Truong;Park, Hae-Il
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.186.4-187
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    • 2003
  • Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

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An Oxalic Acid Sensor Based on Platinum/Carbon Black-Nickel-Reduced Graphene Oxide Nanocomposites Modified Screen-Printed Carbon Electrode

  • Income, Kamolwich;Ratnarathorn, Nalin;Themsirimongkon, Suwaphid;Dungchai, Wijitar
    • Journal of Electrochemical Science and Technology
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    • v.10 no.4
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    • pp.416-423
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    • 2019
  • A novel non-enzymatic oxalic acid (OA) sensor based on the platinum/carbon black-nickel-reduced graphene oxide (Pt/CBNi-rGO) nanocomposite is reported. The nanocomposites were prepared by the ethylene glycol reduction method. Their morphology and chemical composition were characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and transmission electron microscopy (TEM). The results clearly demonstrated the formation of the Pt/CB-Ni-rGO nanocomposite. The electrocatalytic activity of the Pt/CB-Ni-rGO electrode was investigated by cyclic voltammetry. It was determined that the appropriate amount of Pt enhanced the catalytic activity of Pt for oxalic acid electro-oxidation. Moreover, the modified electrode was determined to be highly selective for oxalic acid without interference from compounds commonly found in urine including uric acid and ascorbic acid. The chronoamperometric signal gave a wide linearity range of 20 μM-60 mM and the detection limit (3σ) was found to be 2.35 μM. The proposed method showed high selectivity, stability, and good reproducibility and could be used with micro-volumes of sample for the detection of oxalic acid. Finally, the oxalic acid content in artificial and control urine samples were successfully determined by our proposed electrode.

Synthesis Conditions and Rheological Characteristics of Aluminum Phosphate (인산 알루미늄의 합성조건과 유동학적 특성)

  • 신화우;안세민;정동훈;강태욱;이광표
    • YAKHAK HOEJI
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    • v.35 no.4
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    • pp.319-325
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    • 1991
  • Aluminum phosphate gel was synthesized by reacting aluminum sulfate as a soluble aluminum salt to tribasic sodium phosphate in this study. The optimal synthesis conditions based on the yield of product were investigated by applying Box-Wilson experimental design. It was found that optimal synthesis conditions were as follows: Reaction temperature; $61~71^{\circ}C$, concentration of two reactants; 12.27~13.83%, concentration ratio of two reactants; [AI$_{2}$(SO$_{4}$)$_{3}$]/[Na$_{3}$PO$_{4}$]= 0.5, reaction time; 10.9~12.1 minutes, drying temperature of product; $60~72^{\circ}C$. Aluminum phosphate gel prepared by the optimal synthesis conditions was suspended with four types of natural and synthetic gums at the concentration of 0.375~1.5wv%. Their Theological properties of aluminum phosphate gels were examined with Haake-Rotovisco RV 20 rotational viscometer. It showed that the higher concentration of suspending agents and lower temperature, the higher viscosity. Aluminum phosphate gel suspended by pectin and agar showed plastic flow with rheopexy, and their gels suspended by sodium alginate and sod. CMC showed plastic flow with thixotropy.

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An Efficient and Concise Synthesis of Biologically Interesting Pyranochromenes by Ethylenediamine Diacetate-Catalyzed Double Condensation of Substituted Trihydroxybenzenes to α,β-Unsaturated Aldehydes and Application to Natural Product Analoges

  • Lee, Yong-Rok;Li, Xin
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1739-1745
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    • 2007
  • A new methodology for the preparation of pyranochromenes was developed starting from substituted trihydroxybenzenes. This methodology was applied successfully to the total synthesis of biologically interesting compounds, clusiaphenone A, octandrenolone, O-methyloctandrenolone, trans-3''',4'''-dihydro- 3''',4'''-dihydroxy-O-methyloctandrenolone, trans-3'',4''-dihydro-3'',4''-dihydroxy-O-methyloctandrenolone, flemiculosin, laxichalcone, and racemic 3-deoxy-Ms-II.