Show legend Show as text

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

• Article ID: 12116
  De-Eknamkul W, Suttipanta N, Kutchan TM "Purification and characterization of deacetylipecoside synthase from Alangium lamarckii Thw." - Phytochemistry 55(2) (2000) 177-181
  

  Deacetylipecoside synthase (DIS), the enzyme catalyzing the condensation of dopamine and secologanin to form the (R)-epimer of deacetylipecoside, has been purified 570-fold from the leaves of Alangium lamarckii and partially characterized. The isolated enzyme is a single polypeptide with Mr 30,000, and has a pH optimum at 7.5 and a temperature optimum at 45 degrees C. The apparent Km values for dopamine and secologanin are 0.7 and 0.9 mM, respectively. DIS exhibits high substrate specificity toward dopamine, whereas neither tyramine nor tryptamine are utilized. The enzyme activity is not inhibited by its substrate dopamine, but is inhibited by alangimakine and dehydroalangimakine with similar I50 values of 10 μM. DIS presumably provides (R)-deacetylipecoside for the formation of tetrahydroisoquinoline monoterpene glucosides that also possess an (R)-configuration at the same chiral center.

  characterization, purification, Alangiaceae, Alangium lamarkii, deacetylipecoside, deacetylipecoside synthase, isoquinoline monoterpenoid biosynthesis

  NCBI PubMed ID: 11065292
  Publication DOI: 10.1016/s0031-9422(00)00260-0
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: De-Eknamkul W
  Institutions: Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, Leibniz-Institüt für Pflanzenbiochemie, Halle (Saale), Germany
  Methods: SDS-PAGE, inhibition studies, radiolabeling, radioactivity measurement, HPLC, GPC, extraction, CC, enzymatic assay, precipitation, centrifugation
  
   
  
  Alangium lamarckii
  CSDB ID 65259 (all data & tools)
• Article ID: 12746
  Tanahashi T, Kobayashi C, Itoh A, Nagakura N, Inoue K, Kuwajima H, Wu HX "A tetrahydroisoquinoline-monoterpene glucoside and an iridoid glucoside from Alangium kurzii" - Chemical and Pharmaceutical Bulletin 48(3) (2000) 415-419
  

  From the leaves of Alangium kurzii, a new tetrahydroisoquinoline-monoterpene glucoside, 6-O-methyl-N-deacetylipecosidic acid and a new iridoid glucoside, 10-O-benzoyladoxosidic acid, were isolated along with alangiside, demethylalangiside, 6"-O-β-D-glucosylhenryoside, uridine and four known flavonoid glycosides. The structures of new glucosides were determined on the basis of spectroscopic and chemical methods.

  Alangiaceae, Alangium kurzii, 6-O-methyl-N-deacetylipecosidic acid, 10-O-benzoyladoxosidic acid

  NCBI PubMed ID: 10726868
  Publication DOI: 10.1248/cpb.48.415
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kobe Pharmaceutical University, Kobe, Japan, Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Higashiosaka, Japan, Yunnan Pharmaceutical Group Corporation Technical Center, Kunming, China
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, HPLC, extraction, CC
  
   
  
  Alangium kurzii
  CSDB ID 68127 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: demethylalangiside
Compound class: glycoside, phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12378
  Itoh A, Tanahashi T, Ikejima (née Sato) S, Inoue M, Nagakura N, Inoue K, Kuwajima H, Wu HX "Five phenolic glycosides from Alangium chinense" - Journal of Natural Products 63(1) (2000) 95-98
  

  From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6‘-O-galloylsalicin (1); 4‘,6‘-di-O-galloylsalicin (2); 4‘,6‘-O-(S)-hexahydroxydiphenoylsalicin (3); 4‘,6‘-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-β-d-xylopyranosyl(1→6)-β-d-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods.

  phenolic glycosides, gallic acid, Alangium chinense, salicins

  NCBI PubMed ID: 10650086
  Publication DOI: 10.1021/np990391z
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: tanahash@kobepharma-u.ac.jp
  Institutions: Kobe Pharmaceutical University, Kobe, Japan, Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Higashiosaka, Japan, Yunnan Pharmaceutical Group Corporation, Kunming, China
  Methods: 13C NMR, 1H NMR, deacetylation, NMR-2D, IR, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, evaporation, SI-MS, RP-MPLC, PTLC, HR-SI-MS
  
   
  
  Alangium chinense
  CSDB ID 66393 (all data & tools)
• Article ID: 12745
  Tamaki A, Ide T, Otsuka H "Phenolic glycosides from the leaves of Alangium platanifolium var. platanifolium" - Journal of Natural Products 63(10) (2000) 1417-1419
  

  Chemical investigation of Alangiumplatanifolium var. platanifolium has resulted in the isolation of nine phenolic glycosides that were identified by means of 1D and 2D NMR experiments. Among them, catechol and salicinol O- and 1-O-β-d-(6-O-β-d-apiofuranosyl)glucopyranosides, respectively 1 and 2, and two compounds characterized as adducts of 2,6-dihydroxybenzoic acid with salicin (plataplatanoside, 3) and 4-hydroxysalicin (4-hydroxyalangifolioside, 4) were determined structurally as new compounds.

  phenolic glycosides, Alangium platanifolium var. platanifolium, catechol, salicinol

  NCBI PubMed ID: 11076566
  Publication DOI: 10.1021/np000119l
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Otsuka H
  Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
  
   
  
  Alangium platanifolium var. platanifolium
  CSDB ID 68124 (all data & tools)
• Article ID: 12746
  Tanahashi T, Kobayashi C, Itoh A, Nagakura N, Inoue K, Kuwajima H, Wu HX "A tetrahydroisoquinoline-monoterpene glucoside and an iridoid glucoside from Alangium kurzii" - Chemical and Pharmaceutical Bulletin 48(3) (2000) 415-419
  

  From the leaves of Alangium kurzii, a new tetrahydroisoquinoline-monoterpene glucoside, 6-O-methyl-N-deacetylipecosidic acid and a new iridoid glucoside, 10-O-benzoyladoxosidic acid, were isolated along with alangiside, demethylalangiside, 6"-O-β-D-glucosylhenryoside, uridine and four known flavonoid glycosides. The structures of new glucosides were determined on the basis of spectroscopic and chemical methods.

  Alangiaceae, Alangium kurzii, 6-O-methyl-N-deacetylipecosidic acid, 10-O-benzoyladoxosidic acid

  NCBI PubMed ID: 10726868
  Publication DOI: 10.1248/cpb.48.415
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kobe Pharmaceutical University, Kobe, Japan, Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Higashiosaka, Japan, Yunnan Pharmaceutical Group Corporation Technical Center, Kunming, China
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, HPLC, extraction, CC
  
   
  
  Alangium kurzii
  CSDB ID 68128 (all data & tools)