• Title/Summary/Keyword: bisdemethoxycurcumin

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Solid Phase Extraction(SPE) of Curcuminoids from Turmeric by Optimization Analytical Condition (최적 분석조건에 의한 강황으로부터 Curcuminoids의 고체상추출(SPE))

  • Lee, Kwang Jin;Ma, Jin Yeul;Kim, Young Jun;Kim, Young Sik
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.13 no.10
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    • pp.4927-4935
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    • 2012
  • Turmeric is a medicinal herb with various pharmacological activities. Curcumin, demethoxycurcumin(DMC) and bisdemethoxycurcumin(BDMC) were extracted from turmeric by dipping and ultrasonic wave method. And extraction efficiency was identified using solid phase extraction(SPE). The extracted sample were simultaneously separated and analyzed from three kinds of commercial $C_{18}$ reversed-phase high performance liquid chromatography using water and acetonitrile as mobile phase with isocratic elution mode. Flow rate 1.0mL/min, injection volume $10{\mu}L$ and column oven temperature $40^{\circ}C$ at 425nm wavelength has been conducted. From the experimental results, the optimum mobile phase composition of water/acetonitrile 50/50vol% using RS tech column. It is evident that the amount of curcuminoids extracted(extraction time 4h) by 100% MeOH was higher than any aqueous MeOH composition. Finally, in 100% water extraction, the amount(mAU${\times}$mim) of curcuminoids extracted by SPE was 14.3 and 24.5 times respectively higher than ultrasonic wave and dipping method. The shown results can be applied as sources for pharmaceuticals and functional material.

Changes in the Chemical Stability and Antioxidant Activities of Curcuminoids under Various Processing Conditions (다양한 가공 조건에서 curcuminoid의 화학안정성 및 항산화능 변화)

  • Lee, Bo-Hyun;Kim, Da-Ram;Kang, S-Mee;Kim, Mi-Ri;Hong, Jung-Il
    • Korean Journal of Food Science and Technology
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    • v.42 no.1
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    • pp.97-102
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    • 2010
  • Curcuminoids are polyphenolic compounds and include curcumin and its derivatives possessing a yellow color. In the present study, changes in the chemical stability and antioxidant activities of curcuminoids, including curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BMC), were investigated under various processing conditions. The yellowness of a mixture of the curcuminoids (79.4% curcumin, 16.8% DMC, and 3.8% BMC) at 405 nm was proportional to their amounts analyzed by HPLC. The curcuminoids became less stable with increases of pH and temperature during storage. Exposing a solution of the curcuminoids to autoclave conditions ($121^{\circ}C$, 1.2 atm for 15 min) decreased residual curcuminoid levels by 80-90%; however, as a powder under the same conditions the curcuminoids were much more stable with less than 10% loss. After autoclave treatment, scavenging activities of the curcuminoids for DPPH and ABTS radicals were reduced by 10.3 and 33.4%, respectively, whereas nitric oxide scavenging activity was slightly increased. The residual levels of curcumin, DMC, and BMC after autoclaving were 0.7, 1.4, and 0.9%, respectively, indicating that curcumin was the most sensitive to autoclave treatment. The results indicate that under processing conditions, pH and temperature markedly affect the stability of curcuminoids and major losses of curcuminoids occur after autoclaving. These conditions should be considered when processing foods containing curcuminoids.

Inhibitory Effects of Curcuminoids on $17{\beta}$-hydroxysteroid Dehydrogenase Type 1 Activity in Animal Livers

  • Lee, Sung-Eun;Park, Byeoung-Soo;Kim, Hye Jin;Lee, Eun-Woo;Yum, Jong Hwa
    • Biomedical Science Letters
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    • v.19 no.2
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    • pp.147-152
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    • 2013
  • 17-${\beta}$-hydroxysteroid dehydrogenase type 1 ($17{\beta}$-HSD type 1) mediates the reaction of $17{\beta}$-estradiol (E2) production from estrone (E1). Inhibitory effects of curcuminoids on $17{\beta}$-HSD type 1 activity were investigated to find a lead compound for treating estrogen-dependent diseases including breast cancer. Among curcuminoids, demethoxycurcumin showed potent inhibitory effect ($IC_{50}=2.7{\mu}M$) on mouse $17{\beta}$-HSD type 1. Curcuminoids also displayed their inhibitory effects on the production of $17{\alpha}$-estradiol which is a carcinogenic metabolite produced by the enzyme. Bisdemethoxycurcumin ($IC_{50}=1.3{\mu}M$) showed potent inhibitory effect on the $17{\alpha}$-estradiol production by chicken $17{\beta}$-HSD type 1. Curcuminoids did not inhibit ERE transcriptional activity with and without E2. Taken together, curcuminoids can be used for treating and preventing E2-dependent diseases via inhibition on $17{\beta}$-HSD type 1 activity.

Solid-Phase Extraction of Curcuminoid from Turmeric Using Physical Process Method (물리적 가공법을 이용한 강황으로부터 Curcuminoid의 고체상추출)

  • Lee, Kwang-Jin;Yang, Hye-Jin;Jeong, Sang-Won;Ma, Jin-Yeul
    • Korean Journal of Pharmacognosy
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    • v.43 no.3
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    • pp.250-256
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    • 2012
  • In order to extract the curcuminoid such as curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC) in turmeric (Curcuma longa), solvent extraction methods (dipping and ultrasonic extraction method) and solid-phase extraction (SPE) were used. RP-HPLC (reverse-phase high-performance liquid chromatography) and TLC (thin-layer chromatography) were used for identification and analysis the three curcuminoid. From the experimental results, it is evident that the percentage of curcuminoid extracted from turmeric by ultrasonic extraction method was higher than dipping method. The percentage of curcumin extracted from turmeric by pure methanol was higher than any aqueous methanolic composition. Moreover, the total peak area of three curcuminoid was above 92% in RP-HPLC using solid-phase extraction. These results will form a database for investigating the constituents of natural products and the resources of pharmaceutical, nutrition, and cosmetic products.

Changes in chemical properties and cytotoxicity of turmeric pigments by microwave treatment (마이크로파처리에 의한 심황색소의 화학안정성 및 세포독성 변화)

  • Song, EiSeul;Hong, Jungil
    • Korean Journal of Food Science and Technology
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    • v.49 no.6
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    • pp.693-698
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    • 2017
  • Turmeric is a yellow food-coloring spice containing curcuminoids, curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BMC), which have several physiological effects. In the present study, the effect of microwave irradiation on the chemical properties, antioxidant activity, and cytotoxicity of turmeric were investigated. Degradation of turmeric pigments was accelerated upon increase in irradiation time or intensity at 405 nm. Residual levels of curcumin, DMC, and BMC after 5 minutes of irradiation at 700 W were 11.3, 34.4, and 71.2%, respectively. Scavenging activities of turmeric pigment against 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-azobis (2-amidinopropane) dihydrochloride (AAPH) peroxyl radical and nitrite were enhanced significantly after microwave radiation. However, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity remained unaffected. Cytotoxic activity of turmeric was significantly reduced, and hydrogen peroxide generated from turmeric increased after microwave irradiation. The results obtained indicate that microwave irradiation affects chemical stability and bioactivity of turmeric pigment. Hence, these effects should be considered when processing foods containing turmeric pigments.

Characterization of Natural Compounds as Inhibitors of NS1 Endonuclease from Canine Parvovirus Type 2

  • So-Hyung Kwak;Hayeong Kim;Hyeli Yun;Juho Lim;Dong-Hyun Kang;Doman Kim
    • Journal of Microbiology and Biotechnology
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    • v.33 no.6
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    • pp.788-796
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    • 2023
  • Canine parvovirus type 2 (CPV-2) has high morbidity and mortality rates in canines. Nonstructural protein 1 (NS1) of CPV-2 has endonuclease activity, initiates viral DNA replication, and is highly conserved. Thus, it is a promising target for antiviral inhibitor development. We overexpressed a 41.9 kDa active recombinant endonuclease in Escherichia coli and designed a nicking assay using carboxyfluorescein and quencher-linked ssDNA as substrates. The optimal temperature and pH of the endonuclease were 37℃ and pH 7, respectively. Curcumin, bisdemethoxycurcumin, demethoxycurcumin, linoleic acid, tannic acid, and α-tocopherol inhibited CPV-2 NS1 endonuclease with IC50 values of 0.29 to 8.03 µM. The extracted turmeric, yerba mate, and sesame cake suppressed CPV-2 NS1 endonuclease with IC50 values of 1.48, 7.09, and 52.67 ㎍/ml, respectively. The binding affinity between curcumin, the strongest inhibitor, and CPV-2 NS1 endonuclease by molecular docking was -6.4 kcal/mol. Curcumin inhibited CPV-2 NS1 endonuclease via numerous hydrophobic interactions and two hydrogen bonds with Lys97 and Pro111 in the allosteric site. These results suggest that adding curcuminoids, linoleic acid, tannic acid, α-tocopherol, extracted turmeric, sesame cake, and yerba to the diet could prevent CPV-2 infection.

Quantitative Determination and Stability of Curcuminoid Pigments from Turmeric (Curcuma longa L.) Root (강황 (Curcuma longa L.) 색소의 정량 및 안정성)

  • Kim Kwan-Su;Choung Myoung-Gun;Park Si-Hyung
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.50 no.spc1
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    • pp.211-215
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    • 2005
  • Three curcuminoids [curcumin (CUR), demethoxycurcumin(DEM), bisdemethoxycurcu in (BIS)] are major yellow pigments in turmleric (Curcuma longa L.) root. Contents of curcuminoids in turmeric roots collected from 6 locations were analyzed using, high performance liquid chromatography (HPLC) equipped with reversed-phase column, an UV-Vis detector at 420nm, and eluted with a mixture of acetonitrile: $0.1\%$ acetic acid in water (50 : 50, v/v) as mobile phase. The stability of curcuminoid pigments in $80\%$ methanol extract solution were investigated during storage in a freezer at $-20^{\circ}C$, room temperature in the dark, and light condition. Calibration curves for the determination of curcuminoids were made with significant linearity $(r^2=0.999**)$. Average content of total curcuminoids was 171.5 mg/g, with 91.6 mg/g of CUR, 56.9 mg/g of DEM, and 23.0 mg/g of BIS. Amount of curcuminoids during storage in a freezer was almost not changed while those in room temperature wert reduced and rapid degradation appeared after 60 days. Within 90 days, about $50\%$ curcuminoid decreased in the dark and about $70\%$ in the light condition, indicating the decomposition of curcuminoid pigments followed under light and heat.

Extraction properties and chemical stability of turmeric pigments in salt, sucrose, and acetic acid preservation (염, 당, 산 침지조건에서 심황색소의 추출특성 및 화학적 특성 변화)

  • Kang, Smee;Sung, Yunkyung;Hong, Jungil
    • Korean Journal of Food Science and Technology
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    • v.52 no.1
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    • pp.19-25
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    • 2020
  • Turmeric pigments have been used as coloring agents and functional ingredients. In this study, the extraction property and chemical stability of the pigments were evaluated in several preservative solutions containing NaCl, sucrose, and acetic acid. After 72 h of infusion, the protein and polyphenol levels and antioxidant activity of the turmeric extracts in the solutions were less pronounced than those in water. Acetic acid (12%) was more efficient at extracting curcuminoids from turmeric than water, NaCl (20%), or sucrose (25%). Curcumin was highly abundant in all solutions. The relative yield of bisdemethoxycurcumin (BMC) was the highest in acetic acid, whereas that of curcumin was highest in NaCl and sucrose solutions. Curcuminoids were relatively stable in sucrose and acetic acid; among them, BMC had the highest stability. The stability of the curcuminoid solution decreased based on the increase in NaCl content, whereas it was significantly enhanced in sucrose and acetic acid. The observations from this study can be applied to the processing and storage of turmeric-derived products in these preservative agents.

Antiinflammatory and Antiallergic Activity of Fermented Turmeric by Lactobacillus johnsonii IDCC 9203 (Lactobacillus johnsonii IDCC 9203으로 발효한 울금의 소염 및 항알레르기 효과)

  • Kim, Seong-Beom;Kang, Byung-Hwa;Kwon, Hyuk-Sang;Kang, Jae-Hoon
    • Microbiology and Biotechnology Letters
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    • v.39 no.3
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    • pp.266-273
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    • 2011
  • Although turmeric has numerous pharmacological effects, the poor water-solubility of curcuminoids, active components of turmeric, restricts their systemic availability in orally administered formulations and limits their therapeutic potential. In this study we attempted turmeric fermentation using several probiotic bacteria to improve its solubility, and also investigated the effects of turmeric and fermented turmeric on anti-inflammatory activity. Fermented turmeric, by L. johnsonii IDCC 9203, more strongly inhibited LPS-induced expression of the pro-inflammatory cytokines than non-fermented turmeric and fermented turmeric by other probiotic strains. We used an NC/Nga mouse model for mite antigen-induced atopic dermatitis to examine the efficacy of the fermented turmeric. Fermented turmeric-fed mice exhibited a significantly reduced serum IgE level and mitigated acute inflammation. When the fermented turmeric was pre-treated by oral administration, it had more preventive activity against acute anaphylactic reaction than the non-fermented group. In addition, we observed that fermentation of turmeric leads to increased water-solubility of curcumin and a change in the active components ratios for bisdemethoxycurcumin, demethoxycrucumin and curcumin. Taken together, these results strongly suggest that fermented turmeric by L. johnsonii IDCC 9203 could be used as a functional food ingredient for improving treatments for atopic dermatitis.

Changes in chemical properties, antioxidant activities, and cytotoxicity of turmeric pigments by thermal process (가열처리에 의한 심황색소의 화학적 특성, 산화방지 활성 및 세포독성 변화)

  • Song, Eiseul;Kang, Smee;Hong, Jungil
    • Korean Journal of Food Science and Technology
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    • v.50 no.1
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    • pp.21-27
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    • 2018
  • Turmeric oleoresin, extracted from the rhizome of Curcuma longa L., is a widely-used natural food colorant. Curcuminoids, the major pigments in turmeric, which include curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BMC), possess various physiological activities. In the present study, changes in the chemical properties, antioxidant activities, and cytotoxicity of turmeric pigments upon heating were investigated. Color intensity of turmeric was significantly reduced after heating. Residual levels of curcumin, DMC, and BMC after 15 min of heating at $95^{\circ}C$ were 11.9, 37.4, and 77.3% respectively. Scavenging activities of turmeric against 2,2'-azobis-3-ethyl-benz-thiazoline-6-sulfonic acid (ABTS), 2,2-azobis (2-amidinopropane) hydrochloride (AAPH) peroxyl radicals, and nitrite were significantly enhanced after heating, while 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging activity remained unaffected. Generation of $H_2O_2$ from turmeric was increased via thermal decomposition. Cytotoxicity of turmeric pigments against colon cancer and normal intestinal cells was reduced significantly after heating. The results indicate that thermal processing affects chemical properties and bioactivities of turmeric pigments. These effects should be considered during the processing of foods containing turmeric pigments.