Syringaresinol

Syringaresinol
Names

IUPAC name 4,4'-(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)
Other names (+)-Syringaresinol (−)-Syringaresinol
Identifiers
CAS Number	21453-69-0
3D model (Jmol)	Interactive image
ChemSpider	391324
PubChem	443023
InChI InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m0/s1 Key: KOWMJRJXZMEZLD-HCIHMXRSSA-N
SMILES O4[C@H](c1cc(OC)c(O)c(OC)c1)[C@@H]2[C@@H]([C@H](OC2)c3cc(OC)c(O)c(OC)c3)C4
Properties
Chemical formula	C₂₂H₂₆O₈
Molar mass	418.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Syringaresinol is a lignan found in Castela emoryi,^[1] in Prunus mume^[2] or in Magnolia thailandica.^[3]

This compound inhibits Helicobacter pylori motility.^[2]

Eleutheroside E, one of the glycosides isolated from the prickly eleutherococcus, is identical with acanthoside D, which is one of the glycosides isolated from the cluster-flowering acanthopanax and represents the di-β-D-glucoside of (−)-syringaresinol.^[4]

Gallery

(+)-syringaresinol -O-β-D-glucoside (eletheroside E) A constituent of Eleutherococcus senticosus.

References

↑ Stöcklin, W.; De Silva, L.B.; Geissman, T.A. (1969). "Constituents of holacantha emoryi". Phytochemistry. 8 (8): 1565. doi:10.1016/S0031-9422(00)85931-2.
1 2 Miyazawa, M; Utsunomiya, H; Inada, K; Yamada, T; Okuno, Y; Tanaka, H; Tatematsu, M (2006). "Inhibition of Helicobacter pylori motility by (+)-Syringaresinol from unripe Japanese apricot". Biological & Pharmaceutical Bulletin. 29 (1): 172–3. doi:10.1248/bpb.29.172. PMID 16394533.
↑ Monthong (2011). "(+)-Syringaresinol Lignan from New Species Magnolia Thailandica". American Journal of Applied Sciences. 8 (12): 1268. doi:10.3844/ajassp.2011.1268.1271.
↑ Identity of eleutheroside E with acanthoside D. Yu. S. Ovodov, G. M. Frolova, L. A. Elyakova and G. B. Elyakov, Bulletin of the Academy of Sciences of the USSR, Division of chemical science, November 1965, Volume 14, Issue 11, pages 2035-2036, doi:10.1007/BF00845912

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

Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol

Neolignans	Balanophonin Eusiderin Honokiol 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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