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Structure type: monomer ; 383 [M+Na]+
C₁₇H₂₉O₈
Trivial name: monoterpene glycoside
Compound class: saponin glycoside

• Article ID: 11144
  Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" - Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
  

  From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

  13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside

  Publication DOI: 10.1248/cpb.45.807
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
  
   
  
  Acacia concinna
  CSDB ID 60327 (all data & tools)

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Structure type: oligomer
Trivial name: kinmoonoside A
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_136907,IEDB_140628,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 12757
  Tezuka Y, Honda K, Banskota AH, Thet MM, Kadota S "Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar" - Journal of Natural Products 63(12) (2000) 1658-1664
  

  Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.

  cytotoxicity, Acacia concinna, kinmoonosides A-C, HT-1080 fibrosarcoma

  NCBI PubMed ID: 11141109
  Publication DOI: 10.1021/np000347f
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: kadota@ms.toyama-mpu.ac.jp
  Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  
   
  
  Acacia concinna
  CSDB ID 68182 (all data & tools)