Emodin Derivatives and
µ-Calpain Activity
453
De La Rue, W. and Müller, H., On some constituents of
rhubarb. Quart. J., Chem. Soc. London, 10, 298-307 (1858).
Di Napoli, G., Preparation and serine proteinase inhibition
activity of new rhein derivatives. EP 822178 A1 (1998).
Eder, R. and Widmer, C., Derivatives of methylanthraquinone.
III. Synthesis of "frangula" emodin. Helv. Chim. Acta, 6,
966-981 (1923)
Eder, R. and Hauser, F., β-Methylanthraquinone derivatives.
V. Frangula emodin, emodic acid and derivatives. Helv.
Chim. Acta, 8, 126-139 (1925).
Falk, H. and Schoppel, G. A synthesis of emodin anthrone.
Monat. Chem., 122, 739-744 (1991).
mination of 1,3,8-triacetylemodin. Reduction of emodin
and citreorosein with SnCl2 in a 1:1 mixture of HOAc
and HCl afforded the corresponding anthrones in 90%
and 92% yield, respectively, while the corresponding
10-desoxyemodin carbaldehyde was prepared by MnO2
oxidation of 10-desoxycitreorosein. 10-Desoxycitreoro-
sein and emodin carbaldehyde showed inhibitory
activities against
µ-calpain at the level of IC50 20.15
and 25.77 M, respectively. Studies on the derivatiza-
µ
tion and biological properties of the compounds are in
progress.
Fujimoto, H., Nakamura, E., Okuyama, E., and Ishibashi,
M., Six immunosuppressive features from an Ascomycete,
Zopfiella longicaudata, found in a screening study moni-
tored by immune-modulatory activity. Chem. Pharm.
Bull., 52, 1005-1008 (2004).
ACKNOWLEDGEMENTS
Financial support from Yeungnam University Re-
search Grant (2008) is gratefully appreciated.
Gill, M. and Morgan, P. M., New fungal anthraquinones.
ARKIVOC, 145-156 (2001).
REFERENCES
Goel, R. K., Das Gupta, G., Ram, S. N., and Pandey, V. B.,
Antiulcerogenic and anti-inflammatory effects of emodin,
isolated from Rhamnus triquerta wall. Indian J. Exp.
Biol., 29, 230-232 (1991).
Haller, J. W. E. and Goodall, F. L., Reduction products of the
hydroxyanthraquinones. Part IV. J. Chem. Soc. Trans.,
231-239 (1924)
Anslow, W. K., Breen, J., and Raistrick, H., Emodic acid (4,5,7-
trihydroxyanthraquinone-2-carboxylic acid) and ω-hydroxy-
emodin(4,5,7-trihydroxy-2-(hydroxymethyl)anthraquinone),
metabolic products of a strain of Penicillium cyclopium
Westling. Biochem. J., 34, 159-168 (1940).
Banville, J. and Prassard, P., Reactions of ketene acetals.
Part VI. Total syntheses of the anthraquinones (±)-nalgio-
vensin, (±)-isorhodoptilometrin, and (±)-rhodoptilometrin.
J. Chem. Soc. Perkin Trans. I, 613-619 (1976).
Bloomer, J. L., Staliano, K. W., and Gazzillo, J. A., Prepara-
tion of functionalized juglone acetates and juglones via
1,4-dimethoxynaphthalene derivatives: synthesis of anthra-
Haag-Berrurier, M., Garnier, P., and Anton, R., Chemical
study of Cassia rogeoni. Planta Med., 31, 201-211 (1977).
Hauschild, G., Steiner, M., and Glombitza, K. W., Quantita-
tive determination of the anthraquinones of various
lichens. Planta Med., 20, 1-7 (1971).
Hirose, Y., Suehiro, Y., Furukawa, Y., and Murakami, T.,
Chemische Stundien ueber natuerliche Anthraquinone,
II: Synthese von Citreoroseine, Fallacinol und Fallacinal.
Chem. Pharm. Bull., 30, 4186-4188 (1982).
Huang, H. C., Chang, J. H., Tung, S. F., Wu, R. T., Foegh, M.
L., and Chu, S. H., Immunosuppressive effect of emodin, a
free radical generator. Eur. J. Pharmacol., 211, 359-364
(1992).
quinones related to rhein and aloe-emodin. J. Org. Chem.,
58, 7906-7912 (1993).
Brockmann, H., Kluge, F., and Muxfeldt, H., Total synthesis
of hypericin. Chem. Ber., 90, 2302-2318 (1957).
Cameron, D. W. and Raverty, W. D., Pseudohypericin and
other phenanthroperylene quinines. Aust. J. Chem., 29,
1523-1533 (1976).
Cameron, D. W. and Crossley, M. J., Synthesis of emodin
methyl ethers. Aust. J. Chem., 30, 1161-1165 (1977)
Chandler, C. J., Deady, L. W., and Reiss, J. A., Synthesis of
some 2,9-disubstituted-1,10-phenanthrolines. J. Hetero-
cyclic Chem., 18, 599-601 (1981).
Ishii, H., Seo, S., Tori, K., Tozyo, T., and Yoshimura, Y., The
structures of saikosaponin-E and acetylsaikosaponins,
minor components isolated from Bupleurum falcatum L.,
determined by C-13 NMR spectroscopy. Tetrahedron
Lett., 1227-1230 (1977).
Chang, C. H., Lin, C. C., Yang, J. J., Namba, T., and Hattori,
M., Anti-inflammatory effects of emodin from Ventilago
leiocarpa. Am. J. Chin. Med., 24, 139-142 (1996).
Jacobson, R. and Adams, R., Trihydroxy-methylanthraqui-
nones. III. Synthesis of emodin. J. Am. Chem. Soc., 46,
1312-1316 (1924).
Chang, H. W. and Son, J. K., Pharmaceutical composition for
preventing and treating diseases comprising anthraqqui-
none derivatives. KR Patent 85517 (2011).
Jaysuriya, H., Koonchanok, N. M., Geahlen, R. L., Mc-
Laughlin, J. L., and Chang, C.-J., Emodin, a protein tyrosine
kinase inhibitor from Polyginium cuspidatum
. J. Nat.
Cohen, P. A., Hudson, J. B., and Toweres, G. H. N., Antiviral
activities of anthraquinones, bianthrones and hypericin
derivatives from lichens. Experimentia, 52, 180-184 (1996).
Danielson, K., Aksnes, D. W., and Francis, G. W., NMR study
of some anthraquinones from rhubar. Magn. Reson. Chem.,
30, 359-360 (1992).
Prod., 55, 696-698 (1992).
Kang, D. H., Jun, K. Y., Lee, J. P., Pak, C. S., Na, Y., and Kwon,
Y., Identification of 3-acetyl-2-aminoquinolin-4-one as a
novel, nonpeptidic scaffold for specific calpain inhibition
activity. J. Med. Chem., 52, 3093-3097 (2009).
Kelly, T. R., Chandrakumar, N. S., Walters, N., and Blancaflor,