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Acutissimin A

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Acutissimin A
Chemical structure of acutissimin A
Chemical structure of acutissimin A
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C56H38O31/c57-15-2-1-10(3-17(15)59)47-22(64)4-11-16(58)8-18(60)27(48(11)84-47)32-31-34-30(43(73)46(76)44(31)74)29-33-28(41(71)45(75)42(29)72)26-14(7-21(63)37(67)40(26)70)53(78)83-23-9-82-52(77)12-5-19(61)35(65)38(68)24(12)25-13(6-20(62)36(66)39(25)69)54(79)85-49(23)51(87-56(33)81)50(32)86-55(34)80/h1-3,5-8,22-23,32,47,49-51,57-76H,4,9H2/t22-,23+,32+,47+,49+,50-,51-/m0/s1Key: DRHVFLXLYQESEQ-DHGKJAGISA-N
  • InChI=1/C56H38O31/c57-15-2-1-10(3-17(15)59)47-22(64)4-11-16(58)8-18(60)27(48(11)84-47)32-31-34-30(43(73)46(76)44(31)74)29-33-28(41(71)45(75)42(29)72)26-14(7-21(63)37(67)40(26)70)53(78)83-23-9-82-52(77)12-5-19(61)35(65)38(68)24(12)25-13(6-20(62)36(66)39(25)69)54(79)85-49(23)51(87-56(33)81)50(32)86-55(34)80/h1-3,5-8,22-23,32,47,49-51,57-76H,4,9H2/t22-,23+,32+,47+,49+,50-,51-/m0/s1Key: DRHVFLXLYQESEQ-DHGKJAGIBL
SMILES
  • OC1=C(C2=C(O)C(O)=C(O)C=C2C(O((OC3=O)(O4)(C5=C(O)C=C(O)C6=C5O(C7=CC=C(O)C(O)=C7)(O)C6)C8=C(O)C(O)=C(O)C(C9=C3C%10=C(O)C(O)=C9O)=C8C4=O)(OC(C%11=C%10C(O)=C(O)C(O)=C%11)=O)COC%12=O)=O)C%12=CC(O)=C1O
Properties
Chemical formula C56H38O31
Molar mass 1206.88 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acutissimin A is a flavono-ellagitannin, a type of tannin formed from the linking of a flavonoid with an ellagitannin.

In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with a flavanoid in wine acutissimin A is created. In separate studies this phenolic compound has been shown to be 250 times more effective than the pharmaceutical drug Etoposide in stopping the growth of cancerous tumors.

See also

References

  1. Quideau S, Jourdes M, Saucier C, Glories Y, Pardon P, Baudry C (December 2003). "DNA topoisomerase inhibitor acutissimin a and other flavano-ellagitannins in red wine". Angewandte Chemie. 42 (48): 6012–4. doi:10.1002/anie.200352089. PMID 14679557.
  2. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH (August 1992). "Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents". Journal of Natural Products. 55 (8): 1033–43. doi:10.1021/np50086a002. PMID 1431932.
  3. Quideau S, Jourdes M, Saucier C, Glories Y, Pardon P, Baudry C (2003). "DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano-Ellagitannins in Red Wine". Angewandte Chemie. 115 (48): 6194–6. Bibcode:2003AngCh.115.6194Q. doi:10.1002/ange.200352089. While it would be quite inappropriate to infer from the presence of acutissimin A in red wine that this beverage possesses antitumor properties, our work shows for the first time that wine contains polyphenolic molecules displaying both ellagitannin and flavanoid structural features.
Flavono-ellagitannins (complex tannins)
Types
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