Steganacin
![]() (−)-Steganacin | |
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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 | |
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Properties | |
Chemical formula | C24H24O9 |
Molar mass | 456.447 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Steganacin is an dibenzocyclooctadiene lactone, an unusual type of lignan.[1] It exhibits some antileukemic properties in vitro.[2] It has been isolated from Steganotaenia araliacea.[2] (−)-Steganacin is the natural form.[3]
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.
- ^ a b 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.
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Types of 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
- Arctiin
- Aviculin (isolariciresinol-9'-rhamnopyranoside)
- Secoisolariciresinol diglucoside (SDG)
- Balanophonin
- Eusiderin
- Honokiol
- Interiotherin
- Linderin A
- Magnolol
- Megaphone
- 4-O-Methylhonokiol
- Rhaphidecursinol A
- Rhaphidecursinol B
- 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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