• 제목/요약/키워드: Glycoside compounds

검색결과 153건 처리시간 0.018초

TLC-DM을 이용한 Rubus속 4종 식물의 Triterpenoid 함량 비교 (Comparison of Triterpenoid Contents of the Four Rubus Plants in Korea Using TLC-DM)

  • 남정환;정현주;최종원;김원배;박희준
    • 생약학회지
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    • 제38권2호통권149호
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    • pp.187-191
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    • 2007
  • The extraction yield of the methanolic extracts and 19${\alpha}$-hydroxyursane-type triterpenoid (19${\alpha}$-HUT) fraction were investigated in the unripe and ripe fruits and the leaves of the four Rubus plants (Rubus coreanus, R. crataegifolius, R. phoenicolasius, R. pungens var. oldhami) to develop the biomaterial 19${\alpha}$-HUT mixture as functional foods. Thin layer chromatogaphy-Densitometer (TLC-DM) was used to analyze the individual quantity of 19${\alpha}$-HUTs using standard compounds (euscaphic acid, tormentic acid, 23-hydroxytormentic acid, kaji-ichigoside F$_1$, rosamultin, niga-ichigoside F$_1$). The content of methanolic extract of the fruits were higher in the ripe stage than in the unripe stage whereas the content of 19${\alpha}$-HUT mixture varied with each Rubus species. The Rubus plants containing the highest amount of 19${\alpha}$-HUTs in the leaves were R. coreanus, R. phoenicolasius and R. pungens var. oldhami while only R. cratagefolius showed the highest content in the ripe fruits. The mean of total genin content of 19${\alpha}$-HUTs was 0.94 mg/g; that of the glycosides was 0.60 mg/g. The genin quantity was found in the order of 23-hydroxytormentic acid> euscaphic acid> tormentic acid; the glycoside was observed in the order of niga-ichig-oside F$_1$> kaji-ichigoside F$_1$> rosmaultin, by which the biosynthetic pathway of 23-hydroxytormentic acid and its glucoside niga-ichigoside F$_1$ via the intermediates tormentic acid and/or rosamultin was presumed. It is also suggested that the ripe fruits of R. crataegifolius will be desirable to use as functional foods rather than unripe fruits.

A Novel pH-Stable, Bifunctional Xylanase Isolated from a Deep-Sea Microorganism, Demequina sp. JK4

  • Meng, Xin;Shao, Zongze;Hong, Yuzhi;Lin, Ling;Li, Chanjuan;Liu, Ziduo
    • Journal of Microbiology and Biotechnology
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    • 제19권10호
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    • pp.1077-1084
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    • 2009
  • A genomic library was constructed to clone a xylanase gene (Mxyn10) from Demequina sp. JK4 isolated from a deep sea. Mxyn10 encoded a 471 residue protein with a calculated molecular mass of 49 kDa. This protein showed the highest sequence identity (70%) with the xylanase from Streptomyces lividans. Mxyn10 contains a catalytic domain that belongs to the glycoside hydrolase family 10 (GH10) and a carbohydrate-binding module (CBM) belonging to family 2. The optimum pH and temperature for enzymatic activity were pH 5.5 and $55^{\circ}C$, respectively. Mxyn10 exhibited good pH stability, remaining stable after treatment with buffers ranging from pH 3.5 to 10.0. The protein was not significantly affected by a variety of chemical reagents, including some compounds that usually inhibit the activity of other related enzymes. In addition, Mxyn10 showed activity on cellulose. These properties mark Mxyn10 as a potential enzyme for industrial application and saccharification processes essential for bioethanol production.

Anti-Inflammatory Effect of Flavonoids from Brugmansia arborea L. Flowers

  • Kim, Hyoung-Geun;Jang, Davin;Jung, Young Sung;Oh, Hyun-Ji;Oh, Seon Min;Lee, Yeong-Geun;Kang, Se Chan;Kim, Dae-Ok;Lee, Dae Young;Baek, Nam-In
    • Journal of Microbiology and Biotechnology
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    • 제30권2호
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    • pp.163-171
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    • 2020
  • Brugmansia arborea L. (Solanaceae), commonly known as "angel's trumpet," is widely grown in North America, Africa, Australia, and Asia. It has been mainly used for ornamental purposes as well as analgesic, anti-rheumatic, vulnerary, decongestant, and anti-spasmodic materials. B. arborea is also reported to show anti-cholinergic activity, for which many alkaloids were reported to be principally responsible. However, to the best of our knowledge, a phytochemical study of B. arborea flowers has not yet been performed. Four flavonol glycosides (1-4) and one dihydroflavanol (5) were for the first time isolated from B. arborea flowers in this study. The flavonoids showed significant antioxidant capacities, suppressed nitric oxide production in lipopolysaccharide (LPS)-treated RAW 264.7 cells, and reduced inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2) protein production increased by LPS treatment. The contents of compounds 1-4 in n-BuOH fraction were determined to be 3.8 ± 0.9%, 2.2 ± 0.5%, 20.3 ± 1.1%, and 2.3 ± 0.4%, respectively, and that of compound 5 in EtOAc fraction was determined to be 12.7 ± 0.7%, by HPLC experiment. These results suggest that flavonol glycosides (1-4) and dihydroflavanol (5) can serve as index components of B. arborea flowers in standardizing anti-inflammatory materials.

Antioxidant activity and anti-inflammatory activity of ethanol extract and fractions of Doenjang in LPS-stimulated RAW 264.7 macrophages

  • Kwak, Chung Shil;Son, Dahee;Chung, Young-Shin;Kwon, Young Hye
    • Nutrition Research and Practice
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    • 제9권6호
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    • pp.569-578
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    • 2015
  • BACKGROUND/OBJECTIVES: Fermentation can increase functional compounds in fermented soybean products, thereby improving antioxidant and/or anti-inflammatory activities. We investigated the changes in the contents of phenolics and isoflavones, antioxidant activity and anti-inflammatory activity of Doenjang during fermentation and aging. MATERIALS/METHODS: Doenjang was made by inoculating Aspergillus oryzae and Bacillus licheniformis in soybeans, fermenting and aging for 1, 3, 6, 8, and 12 months (D1, D3, D6, D8, and D12). Doenjang was extracted using ethanol, and sequentially fractioned by hexane, dichloromethane (DM), ethylacetate (EA), n-butanol, and water. The contents of total phenolics, flavonoids and isoflavones, 2,2-diphenyl-1 picryl hydrazyl (DPPH) radical scavenging activity, and ferric reducing antioxidant power (FRAP) were measured. Anti-inflammatory effects in terms of nitric oxide (NO), prostaglandin (PG) E2 and pro-inflammatory cytokine production and inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 expressions were also measured using LPS-treated RAW 264.7 macrophages. RESULTS: Total phenolic and flavonoid contents showed a gradual increase during fermentation and 6 months of aging and were sustained thereafter. DPPH radical scavenging activity and FRAP were increased by fermentation. FRAP was further increased by aging, but DPPH radical scavenging activity was not. Total isoflavone and glycoside contents decreased during fermentation and the aging process, while aglycone content and its proportion increased up to 3 or 6 months of aging and then showed a slow decrease. DM and EA fractions of Doenjang showed much higher total phenolic and flavonoid contents, and DPPH radical scavenging activity than the others. At $100{\mu}g/mL$, DM and EA fractions of D12 showed strongly suppressed NO production to 55.6% and 52.5% of control, respectively, and PGE2 production to 25.0% and 28.3% of control with inhibition of iNOS or COX-2 protein expression in macrophages. CONCLUSIONS: Twelve month-aged Doenjang has potent antioxidant and anti-inflammatory activities with high levels of phenolics and isoflavone aglycones, and can be used as a beneficial food for human health.

Novel enzymatic elimination method for the chromatographic purification of ginsenoside Rb3 in an isomeric mixture

  • Cui, Chang-Hao;Fu, Yaoyao;Jeon, Byeong-Min;Kim, Sun-Chang;Im, Wan-Taek
    • Journal of Ginseng Research
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    • 제44권6호
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    • pp.784-789
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    • 2020
  • Background: The separation of isomeric compounds from a mixture is a recurring problem in chemistry and phytochemistry research. The purification of pharmacologically active ginsenoside Rb3 from ginseng extracts is limited by the co-existence of its isomer Rb2. The aim of the present study was to develop an enzymatic elimination-combined purification method to obtain pure Rb3 from a mixture of isomers. Methods: To isolate Rb3 from the isomeric mixture, a simple enzymatic selective elimination method was used. A ginsenoside-transforming glycoside hydrolase (Bgp2) was employed to selectively hydrolyze Rb2 into ginsenoside Rd. Ginsenoside Rb3 was then efficiently separated from the mixture using a traditional chromatographic method. Results: Chromatographic purification of Rb3 was achieved using this novel enzymatic elimination-combined method, with 58.6-times higher yield and 13.1% less time than those of the traditional chromatographic method, with a lower minimum column length for purification. The novelty of this study was the use of a recombinant glycosidase for the selective elimination of the isomer. The isolated ginsenoside Rb3 can be used in further pharmaceutical studies. Conclusions: Herein, we demonstrated a novel enzymatic elimination-combined purification method for the chromatographic purification of ginsenoside Rb3. This method can also be applied to purify other isomeric glycoconjugates in mixtures.

Quality Evaluation of Modified Bo-Yang-Hwan-O-Tang by Capillary Electrophoresis and High-performance Liquid Chromatography

  • Chen, Jianbo;Wu, Enqi;Zhu, Hongmei;Lee, Kwan-Jun;Chu, Van Men;Cho, Cheong-Weon;Kim, Young-Ho;Park, Yong-Ki;Lee, Won-Jae;Kang, Jong-Seong
    • Bulletin of the Korean Chemical Society
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    • 제32권8호
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    • pp.2666-2670
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    • 2011
  • High-performance liquid chromatography (HPLC) and capillary electrophoresis (CE) were used to identify five active components in the modified herbal decoction Bo-Yang-Hwan-O-Tang (mBHT), i.e., amygdalin, decursin, paeoniflorin, salvianolic acid B, and calycosin-7-O-${\beta}$-D-glycoside. These components were identified by comparing their retention times and mass spectra with those of reference compounds. The conditions of both analytical methods were optimized and validated. Sufficient separation of target analytes was achieved using a buffer consisting of 40 mM sodium borate and 60 mM sodium dodecylsulfate (SDS) containing 10% methanol (pH 9.5) at 250 nm for CE analysis and gradient elution with a water-methanol mobile phase and ultraviolet (UV) photodiode array detector (DAD) at 250 nm for HPLC analysis. The mBHT components were determined within 65 min by HPLC and 16 min by CE. All calibration curves showed high linearity (R > 0.999) within the ranges tested. Intra-day and inter-day precision were less than 1.6% and 1.8% for HPLC and 2.5% and 4.8% for CE, respectively. The accuracy of the methods ranged from 98.8% to 102.3% for HPLC and from 95.9% to 108.2% for CE.

Cyclodextrin의 Inclusion Complex 형성능과 Fatty Acid와의 Complex 형성조건과 특성 (Comparison of Inclusion Complex Formation Capacity of Cyclodextrins with Various Molecules and Characterization of Cyclodextrin-fatty Acid Complex)

  • 이용현;정승환박동찬
    • KSBB Journal
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    • 제10권2호
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    • pp.149-158
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    • 1995
  • 각종 CD와 여러 종류의 화합물, pH indicator, biostain, 아미노산, 천연배당체, 그리고 fatty acid 간의 inclusion complex 형성능을 비교하였다. Fatty acid가 각종 CD에 대한 포접형성능과 선택성 이 높아 CD 분리용 ligand로 적합함을 알았다. Fatty acid의 포접능과 선택성은 탄소쇄의 길이와 밀접한 상관관계를 나타내어 capric acid는 ${\alpha}$- CD와 palmitic acid는 ${\beta}$-CD와 높은 선택성을 보였다. Complex형성에 미치는 반융조건인 흔합 농도비, pH, ionic strength, 그리고 온도의 영향을 검토하였다. 적정 혼합 농도비는 CD가 50mM 그리고 lig and 인 fatty acid가 50mM 일 때 였으며 , 온도가 중 요한 형성조건으로 작용하였다. 포접되지 않은 CD 와 fatty acid가 포접 된 CD의 분자구조를 X-ray diffraction과 IR spectrum을 사용하여 비교 검토하였으며, DSC로 inclusion complex 형성반응의 en­t thalpy의 변화값(${\gamma}H$)을 측정하여 발열반응임을 확인하였다.

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서양고추냉이 추출물과 분리한 Kaempferol 배당체들의 브로모벤젠 처리 흰쥐에서 in Vitro 지질과산화억제효과 (Effect of Methanol Extract and Kaempferol Glycosides from Armoracia rusticana on the Formation of Lipid Peroxide in Bromobenzene-treated Rats In Vitro)

  • 허종문;이종호;최종원;황기욱;정신교;김문성;박종철
    • 생약학회지
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    • 제29권3호
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    • pp.231-236
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    • 1998
  • Three flavonoid glycosides have been isolated from the aerial part of Armoracia rusticana P. (Cruciferae) in Korea and identified by means of spectral analysis as $kaempferol-3-O-{\beta}-D-xylofuranoside(l)$, $kaempferol-3-O-{\beta}-D-galactopyranoside(2)$ and $kaempferol-3-O-{\beta}-D-xylofuranosyl(1\rightarrow2)-b{\beta}-D-galactopyranoside(3)$. When 1 mg/ml of the methanol extract from the aerial part of this plant was added, lipid peroxide formation in the bromobenzene-treated rat liver decreased by 64%. Among the components isolated from title plant, compounds 2 and 3 reduced the formation of lipid peroxide by 16% and 39% respectively at the concentration of ${10}^{-1}$ mg/ml.

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건조방법에 따른 충주산 병풀의 영양성분과 생리활성 (Nutritional Components and Physiological Activity of Centella asiatica Cultured in Chungju by Drying Method)

  • 엄현주;신현영;지영미;권누리;윤향식;김인재;송용섭;유광원
    • 한국식품영양학회지
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    • 제34권2호
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    • pp.165-173
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    • 2021
  • Centella asiatica (CA) has been used as a nutritional plant as well as a traditional herbal medicine around the world. This study, quality component (proximate composition, total polyphenol, and triterpenoid compound), and antioxidant and anti-inflammatory activities of CA dried using various methods were investigated. Proximate compositions of CA with different drying methods included a large amount of carbohydrates, crude protein, crude ash, and crude fiber. Among the drying methods, cold drying provided the highest total polyphenol content and antioxidant activity, while hot-air drying at 75℃ provided the lowest total polyphenol content and antioxidant activity. In addition, when the major triterpenoid compounds of CA were analyzed, the highest content of asiaticoside of triterpenoid glycoside was obtained with all drying methods. With respect to the total triterpenoid, the highest content was obtained with cold drying (68.8 mg/g) whereas natural drying (31.4 mg/g) provided the lowest content. In anti-inflammatory activity of LPS-stimulated RAW 264.7 cells, EtOH extract of cold drying showed a significantly higher inhibitory activity in comparison to the other drying methods. In conclusion, it is considered that the cold drying method is suitable for industrial preparation of functional materials with high physiological ingredients, and antioxidant and anti-inflammatory activities from CA.

식물유래 2차 대사물질의 병충해 및 잡초 방제효과 (Pathogen, Insect and Weed Control Effects of Secondary Metabolites from Plants)

  • 김종범
    • Applied Biological Chemistry
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    • 제48권1호
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    • pp.1-15
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    • 2005
  • 농작물이 병해충 및 잡초 등에 의하여 피해를 받게 되면 농업생산성은 상당히 저하된다. 따라서 농업생산성을 높이기 위하여 합성농약을 과용해 왔고, 이로 인하여 토양의 질과 농업환경이 파괴되는 결과를 초래하고 있어서 지속적인 농업이 점차 어려워지고 있다. 오늘날의 농업은 농업환경의 파괴를 최소화하고 농산물의 안전성을 확보함과 동시에 생산성을 증대해야하는 복합적인 문제에 직면해 있다. 한편, 식물은 일반적으로 생존하기 위하며 외부의 침입으로부터 자신을 보호하거나 자신의 영역을 확보하기 위하며 다양한 종류의 2차대사물질을 생산하고 방출한다. 병원균이 침입했을 때 식물이 생산하는 항생물질인 phytoalexin으로는 화본과 식물의 경우 flavonoid계와 diterpenoid계의 물질을 생성하고, 쌍자엽 식물은 감염된 병원균의 종류에 상관없이 Leguminosae과는 flavonoids계, Cruciferae과는 indole 유도체, Solanaceae과는 sesquiterpenoid계, Umbelliferae과는 coumarin계 물질들을 생성하여 병원균에 저항성을 가진다. 곤충의 생리작용을 저해하거나 섭생을 싫어하게 하는 기능의 물질로는 terpene계의 pyrethrin, azadirachtin, limonin, cedrelanoid, toosendanin, fraxinellone/dictamnine 등이 있으며, alkaloid계로서는 terpenoid와 alkaloid가 결합된 sesquiterpene pyridine 및 norditerpenoids alkaloids와 azepine계, amide계, loline계, stemofoline계, pyrrolizidine계 alkaloids 등이 있다. 식물은 또한 자신의 영역을 확보하기 위하여 다른 식물의 생장을 저해하는 물질을 생성하는데 여기에는 terpene계의 essential oil 및 sesquiterpene lactone과 이외에 benzoxazinoids, glucosinolate, quassinoid, cyanogenic glycoside, saponin, sorgolennone, juglone 등 다수의 2차 대사물질들이 있다. 이와 같은 기능의 2차 대사물질을 병해충 및 잡초 방제에 직, 간접으로 이용하는 것은 친환경농업의 한 가지 방법일 수 있다. 그러나 천연물질들은 자연계에서 쉽게 분해되어 효율이 떨어지는 경우가 많고 식물을 통하여 생산하는데도 한계가 있다. 따라서 보다 안전성과 효율성이 뛰어난 2차 대사물질을 찾아내는 연구와 아울러 방제기능이 있는 물질의 생합성경로를 구명하고 대사공학적으로 이용하므로 병해충에 저항성이 있고 잡초 방제효과를 갖는 형질전환 식물을 육성하는 연구가 지속적으로 이루어져야 할 것이다.