Steganacin

Steganacin is an dibenzocyclooctadiene lactone, an unusual type of lignan.[1] It exhibits some antileukemic properties. It has been isolated from Steganotaenia araliacea.[2] (−)-Steganacin is the natural form.[3]

Steganacin

(−)-Steganacin
Names
Preferred IUPAC name
(3aS,14S,14aS)-6,7,8-Trimethoxy-3-oxo-1,3,3a,4,14,14a-hexahydro-11H-benzo[3,4]furo[3′,4′:6,7]cycloocta[1,2-f][1,3]benzodioxol-14-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C24H24O9/c1-11(25)33-21-14-8-18-17(31-10-32-18)7-13(14)20-12(5-15-16(21)9-30-24(15)26)6-19(27-2)22(28-3)23(20)29-4/h6-8,15-16,21H,5,9-10H2,1-4H3/t15-,16+,21+/m0/s1
    Key: XJTXBUKLGQCZHC-GCKMJXCFSA-N
  • (−): InChI=1S/C24H24O9/c1-11(25)33-21-14-8-18-17(31-10-32-18)7-13(14)20-12(5-15-16(21)9-30-24(15)26)6-19(27-2)22(28-3)23(20)29-4/h6-8,15-16,21H,5,9-10H2,1-4H3/t15-,16+,21+/m1/s1
    Key: XJTXBUKLGQCZHC-XFQAVAEZSA-N
  • (+): CC(=O)O[C@H]1[C@@H]2COC(=O)[C@H]2CC3=CC(=C(C(=C3C4=CC5=C(C=C14)OCO5)OC)OC)OC
  • (−): CC(=O)O[C@H]1c2cc3c(cc2-c4c(cc(c(c4OC)OC)OC)C[C@@H]5[C@@H]1COC5=O)OCO3
Properties
C24H24O9
Molar mass 456.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Notes
  1. Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews. 2 (3): 371–390. doi:10.1023/B:PHYT.0000045487.02836.32. S2CID 6276953.
  2. Kupchan, SM; Britton, RW; Ziegler, MF; Gilmore, CJ; Restivo, RJ; Bryan, RF (21 February 1973). "Steganacin and steganangin, novel antileukemic lignan lactones from Steganotaenia araliacea". Journal of the American Chemical Society. 95 (4): 1335–6. doi:10.1021/ja00785a054. PMID 4687687.
  3. Augros, David; Yalcouye, Boubacar; Choppin, Sabine; Chessé, Matthieu; Panossian, Armen; Leroux, Frédéric R. (18 January 2017). "Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin: Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin" (PDF). European Journal of Organic Chemistry. 2017 (3): 497–503. doi:10.1002/ejoc.201601239.
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