Acutissimin A

Acutissimin A

Identifiers
CAS number	108906-66-7
PubChem	44559699
ChemSpider	10258694^Y
Jmol-3D images	Image 1
SMILES 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
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/s1^Y Key: DRHVFLXLYQESEQ-DHGKJAGISA-N^Y 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
Properties
Molecular formula	C₅₆H₃₈O₃₁
Molar mass	1206.88 g/mol
Exact mass	1206.139705 u
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 phenols in wine acutissimin A is created. In separate studies this polyphenol has been shown to be 250 times more effective then the pharmaceutical drug Etoposide in stopping the growth of cancerous tumors.^[1]^[2]^[3]

References

^ 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.
^ 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.
^ Quideau, StéPhane; Jourdes, Michael; Saucier, Cédric; Glories, Yves; Pardon, Patrick; Baudry, Christian (2003). "DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano-Ellagitannins in Red Wine". Angewandte Chemie 115 (48): 6194–6. 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	Acutissimin A and B \| Epicutissimin A \| Mongolicain \| Mongolicin A and B