Steganacin - Misplaced Pages

Steganacin
Names
(−)-Steganacin
Preferred IUPAC name (3aS,14S,14aS)-6,7,8-Trimethoxy-3-oxo-1,3,3a,4,14,14a-hexahydro-11H-benzofurocyclooctabenzodioxol-14-yl acetate
Identifiers
CAS Number	(−): 41451-68-7
3D model (JSmol)	(+): Interactive image (−): Interactive image
ChEBI	(−): CHEBI:9259
ChEMBL	(−): ChEMBL154064
ChemSpider	(+): 264758 (−): 391322
KEGG	(−): C10886
PubChem CID	(+): 299674 (−): 443021
InChI 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/s1Key: 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/s1Key: XJTXBUKLGQCZHC-XFQAVAEZSA-N
SMILES (+): CC(=O)O12COC(=O)2CC3=CC(=C(C(=C3C4=CC5=C(C=C14)OCO5)OC)OC)OC (−): CC(=O)O1c2cc3c(cc2-c4c(cc(c(c4OC)OC)OC)C51COC5=O)OCO3
Properties
Chemical formula	C₂₄H₂₄O₉
Molar mass	456.447 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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

Notes

Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews. 2 (3): 371–390. Bibcode:2003PChRv...2..371U. doi:10.1023/B:PHYT.0000045487.02836.32. S2CID 6276953.
^ 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.
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. S2CID 100375916.

v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether

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