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Structure type: monomer
Trivial name: gentiopicrin, gentiopicroside, gentiopicrin, gentiopicroside
Compound class: saponin glycoside, glycoside, iridoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7872
  Yin H, Zhao Q, Sun FM, An T "Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla" - Phytomedicine 16(8) (2009) 793-797
  

  Gentiana macrophylla is a traditional Chinese medicinal plant. Its dominant active constituents are secoiridoids, mainly gentiopicrin. The objective of this study was to determine whether endophytic fungi isolated from this plant produce the bioactive ingredient gentiopicrin. Primary screening was done by Dragendorff's reaction and the strain re-selection was done with thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC) to identify the fermentation products of the selected strains. In this study, 20 strains of endophytic fungi were isolated from G. macrophylla, and the extracts from five strains had a positive Dragendorff's reaction. Two strains (QJ16 and QJ18) had a component with the same R(f) value in TLC as that of authentic gentiopicrin and one ingredient of the QJ18 extract had a retention time identical with that of authentic gentiopicrin in HPLC. Therefore, the fungus appears to produce the bioactive ingredient gentiopicrin, as does its host plant, and could be used for the production of gentiopicrin by fermentation.

  endophytic fungus, Gentiana macrophylla, gentiopicrin, secoiridoid, medicinal plant

  NCBI PubMed ID: 19200701
  Publication DOI: 10.1016/j.phymed.2008.12.009
  Journal NLM ID: 9438794
  Publisher: Stuttgart: Urban & Fischer Verlag
  Correspondence: hyin2006@163.com
  Institutions: College of Life Science, Northwest University, Xi’an, China
  Methods: TLC, HPLC, extraction, cell growth
  
   
  
  (fungi), Gentiana macrophylla
  CSDB ID 45955 (all data & tools)
• Article ID: 8337
  de Souza JJ, Vieira IJ, Rodrigues-Filho E, Braz-Filho R "Terpenoids from endophytic fungi" - Molecules 16(12) (2011) 10604-10618
  

  This work reviews the production of terpenoids by endophytic fungi and their biological activities, in period of 2006 to 2010. Sixty five sesquiterpenes, 45 diterpenes, five meroterpenes and 12 other terpenes, amounting to 127 terpenoids were isolated from endophytic fungi

  endophytic fungi, terpenoids

  NCBI PubMed ID: 22183885
  Publication DOI: 10.3390/molecules161210604
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: curcino@uenf.br
  Institutions: Laboratory of Chemical Science, State University of North Fluminense Darcy Ribeiro, Campos dos Goytacazes, Brazil, Laboratory of Biochemistry of Microorganisms Micromolecules (LaBioMMi), Federal University of São Carlos, São Carlos, Brazil, Fundação de Amparo a Pesquisa do Estado do Rio de Janeiro / State University of North Fluminense Darcy Ribeiro / Federal Rural Universty of Rio de Janeiro, Rio de Janeiro, Brazil
  
   
  
  (fungi) sp. QJ16, (fungi) sp. QJ18
  CSDB ID 48040 (all data & tools)
• Article ID: 10883
  Wolfender JL, Hamburger M, Hostettmann K, Msonthi JD, Mavi S "Search for bitter principles in Chironia species by LC-MS and isolation of a new secoiridoid glycoside from Chironia krebsii" - Journal of Natural Products 56 (1993) 682-689
  

  The MeOH root extracts of four Chironia species, Chironia krebsii, Chironia palustris, Chironia purpurascens, and Chironia baccifera, have been screened for secoiridoids by thermospray lc-ms and lc-uv. Swertiamarine [1], gentiopicroside [3], sweroside [4], eustomoside [5], and eustomorusside [6] were tentatively identified, and the presence of the secoiridoid diglycoside 2 was detected. Compounds 1-4 were subsequently isolated from C. krebsii and C. palustris. The structure of the new secoiridoid 2 (chironioside) was established as swertiamarine-6'-O-(b-D-xylopyranoside) by chemical and spectroscopic methods, including double-quantum-filtered phase-sensitive COSY.

  Publication DOI: 10.1021/np50095a004
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Institutions: Institut de Pharmacognosie et Pbytochimie, Ecole de Pharmacie, Universite de Lausanne, Lausanne, Switzerland, Department of Chemistry, Chancellor College, University of Malawi, Zomba, Malawi, National Herbarium and National Botanic Garden, Causeway, Zimbabwe
  Methods: 13C NMR, 1H NMR, gel filtration, TLC, acid hydrolysis, HPLC, UV, LC-MS, LC-UV
  
   
  
  Chironia baccifera, Chironia krebsii, Chironia palustris, Chironia purpurascens, Gentiana asclepiadea
  CSDB ID 140818 (all data & tools)
• Article ID: 11182
  Bergeron C, Marston A, Gauthier R, Hostettmann K "Iridoids and secoiridoids from Gentiana linearis" - Phytochemistry 44(4) (1997) 633-637
  

  Phytochemical investigation of the methanolic extract of Gentiana linearis roots led to the isolation of two novel iridoids (7-O-coumaroyl-loganic acid; 7-O-(4″-O-glucosyl)coumaroyl-loganic acid) and a new secoiridoid (6″″-O-glucosyltrifloroside) together with trifloroside, gentiopicroside, isovitexin and isosaponarin. The structures have been elucidated by MS and NMR spectral data, enzymic and chemical degradation. The chemotaxonomic significance of the isolated secoiridoids and iridoids is briefly discussed.

  flavonoids, Gentianaceae, Iridoids, secoiridoids, Gentiana linearis, 6″″-O-glucosyltrifloroside, 7-O-coumaroyl-loganic acid, 7-O-(4″-O-glucosyl)coumaroyl-loganic acid, linearoside, 4″-O-glucosyllinearoside

  Publication DOI: 10.1016/S0031-9422(96)00636-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, B.E.P., CH-1015 Lausanne, Switzerland
  Methods: 13C NMR, 1H NMR, FAB-MS, sugar analysis, enzymatic hydrolysis, chemical methods, HPLC, alkaline hydrolysis, UV, extraction
  
   
  
  Gentiana linearis
  CSDB ID 60625 (all data & tools)
• Article ID: 11904
  Takeda Y, Masuda T, Honda G, Takashi Y, Ito M, Ashurmetov OA, Khodzhimatov OK, Otsuka H "Secoiridoid glycosides from Gentiana olivieri" - Chemical and Pharmaceutical Bulletin 47(9) (1999) 1338-1340
  

  From the whole plants of Gentiana olivieri, three new bitter secoiridoid glycosides, olivierosides A (1), B (2) and C (3) were isolated together with the known compounds, gentiopicroside, sweroside, 6'-O-β-D-glucosylgentiopicroside, swertiapunimarin, eustomoside, eustomorusside and septemfidoside, and the structures of the new compounds were elucidated based on spectroscopic and chemical evidence.

  Gentianaceae, Olivieroside, Gentiana olivieri, bitter secoiridoid glycoside

  Publication DOI: 10.1248/cpb.47.1338
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Faculty of Integrated Arts and Scinces, The University of Tokushima, Tokushima 770-8502, Japan, Faculty of Pharmaceutical Sciences, The University of Tokushima, Tokushima 770-8505, Japan, Institute of Botany, Academy of Sciences Uzbekistan Republic, 700143, Tashkent, Uzbekistan, Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima 734-8551, Japan
  Methods: 13C NMR, 1H NMR, IR, TLC, enzymatic hydrolysis, HPLC, UV, optical rotation measurement, acetylation, HR-FAB-MS, alkaline methanolysis
  
   
  
  Gentiana olivieri
  CSDB ID 63841 (all data & tools)
• Article ID: 12196
  Glatz Z, Pospísilová J, Musil P "Determination of gentiopicroside in extracts of Centaurium erythreae and Gentiana lutea by micellar electrokinetic capillary chromatography" - Journal of Liquid Chromatography & Related Technologies 23(12) (2000) 1831-1839
  

  Micellar electrokinetic capillary chromatography has been developed as a promising method for the determination of gentiopicroside in plant samples. The separation conditions have been optimised with respect to the different parameters including SDS concentration, pH, and ion strength of the background electrolyte, and temperature of capillary. A buffer consisting of 100 mM SDS in 20 mM sodium dihydrogen phosphate, 20 mM disodium tetraborate pH 8.6 was found to be the most suitable electrolyte for this separation. The applied voltage of 28 kV (positive polarity) and the temperature of capillary 20°C gave the best analysis of gentiopicroside. The linear detection range for concentration versus peak area for the assay is from 5 to 500 μg/mL (correlation coefficient 0.9998) with a detection limit of 0.3 μg/mL. The inter-day reproducibility of the peak area was below 2.5% and the inter-day reproducibility of the migration time was below 0.16 %.

  chromatography, electrophoresis, gentiopicroside, Centaurium erythraea, Gentiana lutea

  Publication DOI: 10.1081/JLC-100100454
  Journal NLM ID: 9605507
  Publisher: Monticello, NY: Marcel Dekker
  Institutions: Department of Biochemistry, Faculty of Science, Masaryk University, Brno, Czechia, Centre of Biochemical Methods, Faculty of Medicine, Masaryk University, Brno, Czechia, Centre of Medicinal Plants, Faculty of Medicine, Masaryk University, Brno, Czechia
  Methods: UV, extraction, capillary electrophoresis (CE), evaporation, sonication
  
   
  
  Centaurium erythraea, Gentiana lutea
  CSDB ID 65587 (all data & tools)
• Article ID: 12414
  Liu H, Wang K, Zhao Y, Zhang H, Chen X, Hu Z "Identification and determination of active components in Gentiana rigescens Franch by micellar electrokinetic chromatography" - Journal of High Resolution Chromatography 23(12) (2000) 697-698
  

  gentiopicroside, Gentiana rigescens Franch, swertiamarin, MEKC

  Publication DOI: 10.1002/1521-4168(20001201)23:12<697::AID-JHRC697>3.0.CO;2-D
  Journal NLM ID: 8914670
  Publisher: Heidelberg; New York: A. Huethig
  Institutions: Department of Chemistry, Lanzhou University, Lanzhou, China
  Methods: extraction, micellar electrokinetic chromatography
  
   
  
  Gentiana rigescens
  CSDB ID 66582 (all data & tools)
• Article ID: 12474
  Menkovic N, Savikin-Fodulović K, Savin K "Chemical composition and seasonal variations in the amount of secondary compounds in Gentiana lutea leaves and flowers" - Planta Medica 66(2) (2000) 178-180
  

  The chemical investigation of MeOH extracts of Gentiana lutea leaves and flowers showed that xanthones were one of the dominant class of compounds. Secoiridoids and flavonoids were also recorded. The amount of secondary metabolites varied depending on development stage. In the phase of flowering, leaves are rich with compounds possessing C-glycoside structures while O-glycoside structures accumulate mainly before flowering.

  flavonoids, secoiridoids, xanthones, Gentiana lutea, C- and O-glycosides, seasonal variations

  NCBI PubMed ID: 10763597
  Publication DOI: 10.1055/s-0029-1243126
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Menković N ; Menković N
  Institutions: Institute for Medicinal Plants Research, Belgrade, Yugoslavia, Faculty of Pharmacy, Department of Pharmacognosy, Belgrade, Yugoslavia
  Methods: 1H NMR, IR, MS, HPLC, UV
  
   
  
  Gentiana lutea
  CSDB ID 66838 (all data & tools)
• Article ID: 12475
  Menkovic N, Savikin-Fodulović K, Momcilović I, Grubisić D "Quantitative determination of secoiridoid and γ-pyrone compounds in Gentiana lutea cultured in vitro" - Planta Medica 66(1) (2000) 96-98
  

  The production of secondary metabolites was studied in shoots, roots, and hairy roots of Gentiana lutea obtained in vitro. In shoots, both secoiridoid and γ-pyrone compounds were detected in amounts similar to those found in aerial parts of plants collected from nature. The most abundant secoiridoid was gentiopicrin while mangiferin was the main compound among the γ-pyrones. The adventitious roots obtained in vitro showed a poor biosynthetic capacity. Upon infection with Agrobacterium rhizogenes, nine hairy root clones were established which differed in the amount of secondary metabolites.

  in vitro, secoiridoids, xanthones, different parts of plant

  NCBI PubMed ID: 10705751
  Publication DOI: 10.1055/s-0029-1243123
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Menković N ; Menković N
  Institutions: Institute for Medicinal Plants Research, Belgrade, Yugoslavia, Institute for Biological Research, Belgrade, Yugoslavia
  Methods: HPLC
  
   
  
  Gentiana lutea
  CSDB ID 66844 (all data & tools)
• Article ID: 12620
  Rojas A, Bah M, Rojas JI, Gutiérrez DM "Smooth muscle relaxing activity of gentiopicroside isolated from Gentiana spathacea" - Planta Medica 66(8) (2000) 765-767
  

  Bioassay directed fractionation of the (1:1) chloroform-methanol extract of Gentiana spathacea H.B.K (Gentianaceae) led to the isolation of gentiopicroside (gentiopicrin) (1), the major spasmolytic component of the plant. Gentiopicroside inhibited, in a concentration-dependent manner, the spontaneous contractions of isolated guinea pig ileum. Contractions induced by histamine, acetylcholine, BaCl2 and KCl on the ileum were also significantly blocked by this monoterpene glucoside, which suggests that this compound might be interfering with calcium influx into the smooth muscle cells.

  gentiopicroside, Gentiana spathacea, smooth muscle cells, calcium influx

  NCBI PubMed ID: 11199140
  Publication DOI: 10.1055/s-2000-9774
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: rojasa@sunserver.uaq.mx
  Institutions: Facultad de Química, Universidad Autónoma de Querétaro, Centro Universitario, Querétaro, México
  Methods: biological assays
  
   
  
  Gentiana spathacea
  CSDB ID 67459 (all data & tools)