Show legend Show as text

Structure type: monomer ; 769.1251 [M+H]+
C₃₅H₂₈O₂₀
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61854 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61855 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61856 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61857 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61858 (all data & tools)
• Article ID: 11876
  Calis I, Kuruüzüm A, Demirezer LO, Sticher O, Ganci W, Rüedi P "Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium" - Journal of Natural Products 62(8) (1999) 1101-1105
  

  (3R)-O-β-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-β-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[β-D-glucopyranosyl-(1→-6)-glucopyranosyl]-oxy-2'-hydroxy-3',6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-β-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-β-D-galactopyranoside (5), quercetin-3-O-β-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-β-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2'-O-galloyl)-β-D-glucopyranoside (8), and quercetin-3-O-β-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.

  isoquercitrin, hyperoside, flavonoid glycoside, phenylvaleric acid glycoside, Polygonum salicifolium, astragalin

  NCBI PubMed ID: 10479312
  Publication DOI: 10.1021/np9900674
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Calis I
  Institutions: Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, TR-061000 Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zurich, Department of Pharmacy, CH-8057 Zurich, Switzerland, University of Zurich, Institute of Organic Chemistry, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, HPLC, UV, optical rotation measurement, ROESY, reduction with NaBH4, antioxidant activities, HMBC, HMQC, DEPT, COSY, MPLC, hydrogenation, DFQ-COSY
  
   
  
  Polygonum salicifolium
  CSDB ID 63331 (all data & tools)
• Article ID: 11901
  Park SH, Oh SR, Jung KY, Lee IS, Ahn KS, Kim JH, Kim YS, Lee JJ, Lee HK "Acylated flavonol glycosides with anti-complement activity from Persicaria lapathifolia" - Chemical and Pharmaceutical Bulletin 47(10) (1999) 1484-1486
  

  During a search for biologically active compounds from traditional medicines, a crude extract of Persicaria lapathifolia was found to have anti-complement activity. Bioassay-guided chromatographic separation of the active constituents led to the isolation of a new acylated kaempferol glycoside (1) and three known acylated quercetin glycosides (2-4). The structures of compounds 1-4 were characterized as kaempferol 3-O-β-D-(6"-p-hydroxybenzoyl)-galactopyranoside, quercetin 3-O-β-D-(6"-feruloyl)-galactopyranoside, quercetin 3-O-β-D-(2"-galloyl)-rhamnopyranoside and quercetin 3-O-β-D-(2"-galloyl)-glucopyranoside, respectively. Compounds 1-4 showed strong anti-complement activity (IC50 values of 4.3, 9.7, 3.9 and 7.6 x 10-5 M, respectively) on the classical pathway of the complement. On the other hand, six isolated flavonol glycosides (5-10) did not show any activity on this system.

  anti-complement activity, Persicaria lapathifolia, kaempferol 3-O-β-D-(6"-p-hydroxybenzoyl)-galctopyranoside, quercetin 3-O-β-D-(6"-feruloyl)-galactopyranoside, quercetin 3-O-β-D-(2"-galloyl)-rhamnopyranoside, quercetin 3-O-β-D-(2"-galloyl)-glucopyranoside

  NCBI PubMed ID: 10553645
  Publication DOI: 10.1248/cpb.47.1484
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Natural Product Biosynthesis Research Unit, Korea Research Institute of Bioscience & Biotechnology, Yusong P.O. Box 115, Taejon 305-600, Korea and College of Pharmacy, Chungbuk National University, Cheongju 361-763, Korea
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, UV, complement assays, HMBC, HR-FAB-MS
  
   
  
  Persicaria lapathifolia
  CSDB ID 63827 (all data & tools)
• Article ID: 12275
  Kim Y, Jang DS, Park SH, Yun J, Min BK, Min KR, Lee HK "Flavonol glycoside gallate and ferulate esters from Persicaria lapathifolia as inhibitors of superoxide production in human monocytes stimulated by unopsonized zymosan" - Planta Medica 66(1) (2000) 72-74
  

  Aerial parts of Persicaria lapathifolia S.F. Gray (Polygonaceae) exhibited an inhibitory effect on superoxide production in unopsonized zymosan-stimulated human monocytes. Two known compounds, quercetin 3-O-β-(2″-galloyl)-glucopyranoside and quercetin 3-O-β-(2″-galloyl)-rhamnopyranoside, and a new compound, quercetin 3-O-β-(6″-feruloyl)-galactopyranoside, were isolated as the inhibitors of superoxide production by activity-guided fractionation. IC50 values were shown at the concentrations of 2.1µM by quercetin 3-O-β-(2″-galloyl)-glucopyranoside, 1.9µM by quercetin 3-O-β-(2″-galloyl)-rhamnoypranoside, and 3.5µM by quercetin 3-O-β-(6″-feruloyl)-galactopyranoside whose inhibitory potencies were similar to oxyphenylbutazone (IC50 = 1.9µM) as a positive control.

  Antioxidant activity, zymozan, flavonol glycosides, Persicaria lapathifolia, feruloyl and galloyl esters

  NCBI PubMed ID: 10705740
  Publication DOI: 10.1055/s-0029-1243112
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: youngsoo@cbucc.chungbuk.ac.kr
  Institutions: Natural Product Biosynthesis Research Unit, Korea Research Institute of Bioscience & Biotechnology, Taejeon, South Korea, College of Pharmacy, Chungbuk National University, Cheongju, South Korea
  Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, biological assays, extraction, CC, evaporation, fluorescence detection
  
   
  
  Persicaria lapathifolia
  CSDB ID 65959 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11465
  Kim HJ, Woo ER, Shin CG, Park H "A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase" - Journal of Natural Products 61(1) (1998) 145-148
  

  Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-0-(2 ",6 "-0-digalloyl)-beta-D-galactopyra (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2 "-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 mu g/mL, respectively, against HIV-1 integrase.

  iridoid glucosides, secoiridoid glucosides, loganic acid, loganin, Loasa acerifolia, Loasaceae, acerifolioside, tricoloroside methyl ester

  NCBI PubMed ID: 9461665
  Publication DOI: 10.1021/np970171q
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Woo ER
  Institutions: Division of Applied Science, Korea Institute of Science & Technology, Seoul, South Korea, Department of Biotechnology, Chung-Ang University, An-Sung, Korea
  Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, ESI-MS, acid hydrolysis, MS, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, HR-FAB-MS
  
   
  
  Acer okamotoanum
  CSDB ID 61859 (all data & tools)