Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2000-05-11
2002-06-04
Horlick, Kenneth R. (Department: 1656)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C435S007100
Reexamination Certificate
active
06399581
ABSTRACT:
BACKGROUND OF THE INVENTION
Penasterol (1, FIG.
1
), an acidic steroidal metabolite closely related to lanosterol (2,
FIG. 1
) and possessing potent antileukemic activity, was originally isolated from Penares sp. by Cheng et al in 1988 (Cheng, J.F., J. Kobayashi, H. Nakamura, Y. Ohizumi, Y. Hirata, and T. Sasaki [1988
] J. Chem. Soc. Perkin Trans.I
8:2403-2406; Kobayashi, J. and Y. Ooizurni, [1988] JP 01163196 A2 890627). The compound, together with its close analogues penasterone and acetylpenasterol, isolated from
Penares incrustans
, have been shown to inhibit IgE-dependent histamine release from rat mast cells (Shoji, N., A. Umeyama, S. Motoki, S. Arihara, T. Ishida, K Nomoto, J. Kobayashi, M. Takei [1992
] J. Nat. Prod
. 55(11):1682-1685; Takei, M., A. Umeyama,N. Shoji, S. Arihara, K. Endo [1995
] J. Pharm. Sci
. 84(2):228-230). The erylosides (Carmely, Y., M. Roll, Y. Loya, Y. Kashman [1989
] J. Nat. Prod
. 52(1):167-170; D'auria, M. V., Paloma L. Gomez, R. Riccio, C. Debitus [1992
] Tetrahedron Lett
48(3):491-498; Gulavita, N. K., A. E. Wright, M. Kelly-Borges, R. E. Longley [1994
] Tetrahedron Lett
35(25):4299-4302), isolated from various Erylus spp. constitute a family of glycosides of penasterol and related aglycones. Eryloside A possesses antitumor and antifungal activity, while Eryloside E is an antagonist of C5 a-receptorbinding. The penasterol tetrasaccharide formoside (Jaspars, M. and P. Crews [1994
] Tetrahedron Lett
. 35(41):75,01-7504) was recently isolated by Jaspars et al. from
Erylus formosus.
BRIEF SUMMARY OF THE INVENTION
The subject invention pertains to a novel penasterol disaccharide, eryloside F (3, FIG.
1
). Eryloside F has potent thrombin receptor antagonist activity and, furthermore, inhibits platelet aggregation. Advantageously, the compound has low toxicity against liver hepatocyte (HepG2) cells. The subject invention further concerns the use of salts, derivatives, and analogs of eryloside F. Such salts, derivatives, and analogs of eryloside F can be prepared by a person skilled in the art having the benefit of the disclosure provided herein.
REFERENCES:
patent: 5023250 (1991-06-01), Adams et al.
patent: 01163196 (1988-01-01), None
Kobayashi et al., Marine Natural Products. XXVIII. “The Structures of Sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, 9 New Norlanostane-Triterpenoidal Oligoglycosides from the Puauan Marine Sponge Asteropus Sarasinosum”, Chem. Pharm. Bull. 39 1991.*
Carmely et al., “The Structure of Eryloside A, A New Antitumor and Antifungal 4-Methylated Sterodial Glycoside From the Sponge Erylus Lendenfeldi”, J. Natural Products, vol. 52, No. 1 pp 167-170, 1989.*
Takei, et al., “mechanism of Inhibition of lgE-Dependent Histamine Release From Rat Mast Cells By Penasterol and Penasterone” J. Pharm. Sci. vol.84 No. 2, Feb. 1995.*
Gulativa et al., “ErylosideE from An Alantic Sponge Erylus goffrilleri” Tetrahedron Lett. vol. 35, No. 25, pp4299-4302, 1994.*
Kobayashi et al.(Marine Natural Products. XXVIII. The Structures of Sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine new Norlanostane-Triterpenoidal Oligoglycosides from the Palauan Marine Sponge Asteropus Sarasinosum, Chem. Pharm. Bull. 39, 1991).*
Carmely et al.(“The Structure of Eryloside A, A New Antitumor and Antifungal 4-Methylated Sterodial Glycoside From the Sponge Erylus Lendenfeldi”, J. Natural Products, vol. 52, No. 1, pp. 167-170, 1989).*
Takei, M., A. Umeyama, N. Shoji, S. Arihara, K. Endo (1995) “Mechanism of Inhibition of lgE-Dependent Histamine Release from Rat Mast Cells by Penasterol of Penasterone”Journal of Pharmaceutical Sciences84(2):228-230.
D'Auria, M. Valeria, Luigi Gomez Paloma, Luigi Minale, Raffaele Riccio (1992) “Structure Characterization By Two Dimensional NMR Spectroscopy, of Two Marine Triterpene Oligoglycosides From A Pacific Sponge of The Genus Erylus” (1992)Tetrahedron48(3):491-498.
Fujioka, Toshihiro, Masayo Iwamoto, Yukiko Iwase, Hikaru Okabe, Kunihide Mihashi, Tatsuo Yamauchi (1988) “Studies on the Constituents ofActinostermma lobatumMaxim. III. Structures of Actinostemmosides E and F, New Baccharane-Type Triterpene Glycosides Isolated from the Herb”Chem. Pharm. Bull.36(8):2772-2777.
Jaspars, Marcel and Phillip Crews (1994) “A Triterpene Tetrasaccharide, Formoside, from the Caribbean Choristida SponeErylus Formosus” Tetrahedron Letters35(41):7501-7504.
Carmely, Shumel, Michal Roll, Yosi Loya, Yoel Kashman (1989) “The Structure Of Eryloside A, A New Antitumor And Antifungal 4-Methylated Steroidal Glycoside From The SpongeErylus Lendenfeldi” (1989)Journal of Natural Products52(1):167-170.
Shoji, Noboru, Akemi Umeyama, Setsuko Motoki, Shigenobu Arhara (1992) “Potent Inhibitors of Histamine Release, Two Novel Triterpendoids From the Okinawan Marine SpongePenares Incrustans” Journal of Natural Products55(1):1682-1685.
Cheng, Jie-fei et al. (1988) “Penasterol, a Novel Antileukemic Sterol from the Okinawan Marine Sponge Penares sp.”J. Chem. Soc. Perkin Trans.I 8:2403-2406.
Gulavita, Nanda K., Amy E. Wright, Michelle Kelly-Borges, Ross E. Longley (1994) “Eryloside E From An Atlantic SpongeErylus goffrilleri” Tetrahedron Letters35(25):4299-4302.
Bewley, Carole A., Cécile Debitus, D. John Faulkner (1994) “Microscleroderma A and B. Antifungal Cyclic Peptides from the Lithisid Sponge Microscleroderma sp.”J. Am. Chem. Soc.116:7631-7636.
Schmidt, Eric W. and D. John Faulkner (1998) “Microsclerodermins C-E, Antifungal Cyclic Peptides from the Lithistid Marine SpongesTheonella sp.andMicroscleroderma sp.” (1998)Tetrahedron54:3043-3056.
Langley David
Pomponi Shirley A.
Stead Paul
Wright Amy E.
Harbor Branch Oceanographic Institution Inc.
Horlick Kenneth R.
Maupin Christine
Saliwanchik Lloyd & Saliwanchik
LandOfFree
Compound possessing potent thrombin receptor antagonist... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Compound possessing potent thrombin receptor antagonist..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compound possessing potent thrombin receptor antagonist... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2929364