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Acutissimin A

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Acutissimin A
Chemical structure of acutissimin A
Chemical structure of acutissimin A
Identifiers
3D model (JSmol)
ChemSpider
  • 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/s1 checkY
    Key: DRHVFLXLYQESEQ-DHGKJAGISA-N checkY
  • 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/s1
    Key: DRHVFLXLYQESEQ-DHGKJAGIBL
  • OC1=C(C2=C(O)C(O)=C(O)C=C2C(O[C@@H]([C@H](OC3=O)[C@@H](O4)[C@@H](C5=C(O)C=C(O)C6=C5O[C@H](C7=CC=C(O)C(O)=C7)[C@@H](O)C6)C8=C(O)C(O)=C(O)C(C9=C3C%10=C(O)C(O)=C9O)=C8C4=O)[C@H](OC(C%11=C%10C(O)=C(O)C(O)=C%11)=O)COC%12=O)=O)C%12=CC(O)=C1O
Properties
C56H38O31
Molar mass1206.88 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

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

In 2003, scientists at Institut Européen de Chimie et Biologie inPessac, France found that when the oak tanninvescalagin interacts with a flavanoid in wine acutissimin A is created. In separate studies thisphenolic compound has been shown to be 250 times more effective than the pharmaceutical drugEtoposide in stopping the growth ofcanceroustumors.[1][2][3]

See also

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References

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  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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