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Structure type: monomer
C₁₆H₂₀O₈
Trivial name: kalopanaxin A, coniferylaldehyde 4-O-glucoside
Compound class: glycoside, phenylethanoid glycoside, phenylpropanoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10698
  Sano K, Sanada S, Ida Y, Shoji J "Studies on the constituents of the bark of Kalopanax pictus Nakai" - Chemical and Pharmaceutical Bulletin 39(4) (1991) 865-870
  

  Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P_ (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-glucopyranosyl(1→6)-β-D-glucopyranoside (2), ferulyldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O-(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).

  glycoside, hederagenin, triterpenoid, araliaceae, oleanolic acid, saponin, Kalopanax pictus, phenylpropanoid, kalopanaxin, phenolic compound

  Publication DOI: 10.1248/cpb.39.865
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Showa University, Hatanodai, Japan
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, MS, methanolysis, alkaline hydrolysis, enzymatic digestion, CC
  
   
  
  Kalopanax pictus
  CSDB ID 119761 (all data & tools)
• Article ID: 11492
  Park HJ, Kim DH, Choi JW, Park JH, Han YN "A potent anti-diabetic agent from Kalopanax pictus" - Archives of Pharmacal Research 21(1) (1998) 24-29
  

  To search for the anti-diabetic principle from the stem bark of Kalopanax pictus, seven kinds of chemical constituents including hederagenin glycosides and phenolic glycosides were isolated. The anti-diabetic evaluation of these isolates in the streptozotocin-induced diabetic rats exhibited that kalopanaxsaponin A has a potent anti-diabetic activity in contrast to a mild activity of hederagenin. In addition, significant hypocholesterolemic and hypolipidemic activities of kalopanaxsaponin A and hederagenin were observed. The structure-activity relationship of kalopanaxsaponin A was also investigated in the present work.

  araliaceae, anti-diabetic, Kalopnax pictus, kalopnaxsapoinin A, hedearagenin

  NCBI PubMed ID: 9875510
  Publication DOI: 10.1007/BF03216748
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, Department of Botanical Resources, Sangji University, Wonju, South Korea, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, College of Pharmacy, Kyungsung University, Pusan, South Korea, College of Pharmacy, Pusan Universoty, Pusan, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, extraction, optical rotation measurement, CC, melting point determination
  
   
  
  Kalopanax pictus
  CSDB ID 61985 (all data & tools)
• Article ID: 11794
  Park HJ, Lee MS, Lee KT, Sohn IC, Han YN, Miyamoto KI "Studies on constituents with cytotoxic activity from the stem bark of Syringa velutina" - Chemical and Pharmaceutical Bulletin 47(7) (1999) 1029-1031
  

  Cytotoxic compounds, oleuropein (1) and a phenylethanoid glycoside (2) were isolated from the stem bark of Syringa velutina KOM. along with coniferylaldehyde 4-O-glucoside, syringin, ligstroside, (+)-syringaresinol 4-O-glucoside, (+)-medioresinol 4"-O-glucoside and (-)-olivil 4"-O-glucoside. Phenylethanoid glycoside (2) was identified to be 3,4-dihydroxyphenylethyl alcohol 8-O-β-D-glucopyranoside. THis compound showed the most potent cytotoxic effect on several tumor cell lines (P-388, L-1210, SNU-5 and HL-60) among eitht compounds isolated in the present study. We suggest that the 3,4-dihydroxyphenylethoxy moiety of this compound contributes to cytotoxicity.

  3, cytotoxicity, tumor cell, phenylethanoid glycoside, oleuropein, Syringa velutina, 4-dihydroxyphenylethy alcohol 8-O-β-D-glucopyranoside

  NCBI PubMed ID: 10434406
  Publication DOI: 10.1248/cpb.47.1029
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Botanical Resources, Sangi University, Wonju 220-702, Korea, College of Pharmacy, Kyung-Hee University, Seoul 130-701, Korea, Natural Products Research Institute, Seoul National University, Seoul 110-460, Korea, Department of Pharmacology and Pharmaceutics, Graduate School of Natural Science and Technology, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-9042, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, alkaline hydrolysis, optical rotation measurement, cytotoxicity assay, HMBC, COSY, NOESY
  
   
  
  Syringa velutina
  CSDB ID 62982 (all data & tools)