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Structure type: oligomer
C₄₁H₆₈O₁₄
Trivial name: astragaloside I, astragaloside I (astrasieversianin IV)
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_983931,SB_192

• Article ID: 11140
  Baratta MT, Ruberto G "Cycloartane triterpene glycosides from Astragalus siculus" - Planta Medica 63(3) (1997) 280-282
  

  Based on spectroscopic analysis and chemical degradation, the structures of two saponins isolated from the methanol extract of fresh roots of Astragalus siculus Biv. were established to be that of astrasieversianin II and astragaloside I (also known as astrasieversianin IV), two saponins previously isolated from A. sieversianus Pall and A. membranaceus Benge. A complete assignment of NMR data to the two compounds 1 and 2 is reported for the first time.

  NCBI PubMed ID: 17252355
  Publication DOI: 10.1055/s-2006-957677
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Istituto del C.N.R. per Io Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico, Via del Santuario 110, I-95028 Valverde (CT), Italy
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, acid hydrolysis, chemical methods, extraction
  
   
  
  Astragalus siculus
  CSDB ID 60304 (all data & tools)
• Article ID: 11375
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus" - Journal of Natural Products 61(12) (1998) 1469-1472
  

  Three new cycloartane-type triterpene glycosides, brachyosides A (1), B (3), and C (2), from the roots of Astragalus brachypterus and one new glycoside, cyclocephaloside II (4), from the roots of Astragalusmicrocephalus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol. The structures of the new compounds were established as 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl-6-O-beta-D-gluc opyranosyl-3beta,6alpha,16beta,24(S),25-pentahydrox ycycloartane (1), 3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-24-O-beta-D-glucop yranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxyc ycloartane (2), 20(R),24(S)-epoxy-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta , 25-tetrahydroxycycloartane (3), and 20(R), 24(S)-epoxy-3-O-(4'-O-acetyl)-beta-D-xylopyranosyl-6-O-beta-D-glucopy ranosyl-3beta,6alpha,16beta,25-tetrahydroxycycloart ane (4). For the structure elucidations, 1D- and 2D-NMR experiments and FABMS were used.

  NMR, spectroscopy

  NCBI PubMed ID: 9868145
  Publication DOI: 10.1021/np9801763
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Facoltà di Farmacia, Università degli Studi di Salerno, Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, extraction, optical rotation measurement, TOCSY, CC, DQF-COSY, HMBC, DEPT, HOHAHA, HSQC
  
   
  
  Astragalus microcephalus
  CSDB ID 61482 (all data & tools)
• Article ID: 11830
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Secondary metabolites from the roots of Astragalus trojanus" - Journal of Natural Products 62(4) (1999) 563-568
  

  Six novel cycloartane-type glycosides were isolated from the roots of Astragalus trojanus. Two of these, compounds 1 and 2, have (20R,24S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane as the aglycon, while compounds 3-6 possess 3β,6α,16β,(24S),25-pentahydroxycycloartane as the aglycon. The saccharide moieties linked to the C-3, C-6, and C-24 or C-25 positions of the aglycons in 1-6 contained either xylopyranose, glucopyranose, rhamnopyranose, or arabinopyranose units. Structure elucidation of compounds 1-6 was accomplished through the extensive use of 1D and 2D NMR techniques. In addition, a new oleanene glycoside (7) and a new tryptophan derivative (8) were also isolated and characterized.

  glycoside, cycloartane, Astragalus trojanus

  NCBI PubMed ID: 10217709
  Publication DOI: 10.1021/np980399t
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Çalis I
  Institutions: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy, epartment of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HOHAHA, HSQC
  
   
  
  Astragalus trojanus
  CSDB ID 63172 (all data & tools)
• Article ID: 12024
  Bedir E, Pugh N, Calis I, Pasco DS, Khan IA "Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species" - Biological and Pharmaceutical Bulletin 23(7) (2000) 834-837
  

  In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-κB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 μg/ml except astragaloside I which increased NF-κB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 μg/ml. None of the compounds were active at low dosage levels (0.1 μg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.

  macrophage, immunostimulatory, THP-1, Astragalus, astragaloside I, nuclear factor kappa B (NF-κB)

  NCBI PubMed ID: 10919362
  Publication DOI: 10.1248/bpb.23.834
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Correspondence: Bedir E ; Caliş I ; Khan IA
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Missisippi, Missisippi, USA, Department of Pharmacognosy, School of Pharmacy, The University of Missisippi, Missisippi, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, PCR, MS, RT-PCR, macrophage activity assay
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64864 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₁H₆₈O₁₄
Trivial name: astrasieversianin II
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332

• Article ID: 11140
  Baratta MT, Ruberto G "Cycloartane triterpene glycosides from Astragalus siculus" - Planta Medica 63(3) (1997) 280-282
  

  Based on spectroscopic analysis and chemical degradation, the structures of two saponins isolated from the methanol extract of fresh roots of Astragalus siculus Biv. were established to be that of astrasieversianin II and astragaloside I (also known as astrasieversianin IV), two saponins previously isolated from A. sieversianus Pall and A. membranaceus Benge. A complete assignment of NMR data to the two compounds 1 and 2 is reported for the first time.

  NCBI PubMed ID: 17252355
  Publication DOI: 10.1055/s-2006-957677
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Istituto del C.N.R. per Io Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico, Via del Santuario 110, I-95028 Valverde (CT), Italy
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, acid hydrolysis, chemical methods, extraction
  
   
  
  Astragalus siculus
  CSDB ID 160307 (all data & tools)
• Article ID: 11830
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Secondary metabolites from the roots of Astragalus trojanus" - Journal of Natural Products 62(4) (1999) 563-568
  

  Six novel cycloartane-type glycosides were isolated from the roots of Astragalus trojanus. Two of these, compounds 1 and 2, have (20R,24S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane as the aglycon, while compounds 3-6 possess 3β,6α,16β,(24S),25-pentahydroxycycloartane as the aglycon. The saccharide moieties linked to the C-3, C-6, and C-24 or C-25 positions of the aglycons in 1-6 contained either xylopyranose, glucopyranose, rhamnopyranose, or arabinopyranose units. Structure elucidation of compounds 1-6 was accomplished through the extensive use of 1D and 2D NMR techniques. In addition, a new oleanene glycoside (7) and a new tryptophan derivative (8) were also isolated and characterized.

  glycoside, cycloartane, Astragalus trojanus

  NCBI PubMed ID: 10217709
  Publication DOI: 10.1021/np980399t
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Çalis I
  Institutions: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy, epartment of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HOHAHA, HSQC
  
   
  
  Astragalus trojanus
  CSDB ID 63171 (all data & tools)
• Article ID: 12024
  Bedir E, Pugh N, Calis I, Pasco DS, Khan IA "Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species" - Biological and Pharmaceutical Bulletin 23(7) (2000) 834-837
  

  In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-κB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 μg/ml except astragaloside I which increased NF-κB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 μg/ml. None of the compounds were active at low dosage levels (0.1 μg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.

  macrophage, immunostimulatory, THP-1, Astragalus, astragaloside I, nuclear factor kappa B (NF-κB)

  NCBI PubMed ID: 10919362
  Publication DOI: 10.1248/bpb.23.834
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Correspondence: Bedir E ; Caliş I ; Khan IA
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Missisippi, Missisippi, USA, Department of Pharmacognosy, School of Pharmacy, The University of Missisippi, Missisippi, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, PCR, MS, RT-PCR, macrophage activity assay
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64862 (all data & tools)