Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-05-01
1999-10-12
Burn, Brian M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
549275, 514453, A01N 4312
Patent
active
059654937
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND AND SUMMARY OF THE INVENTION
The botanical family Simaroubaceae includes numerous species distributed primarily in pantropical regions. These plant species have been the source of a large family of bitter terpenoid substances collectively termed quassinoids. Like many plant alkaloids or naturally isolated plant extracts, quassinoids have been found to have diverse biologic activity, including anti-malarial, anti-insecticidal, anti-amoebicidal, anti-leukemic, and anti-viral activity.
The great majority of quassinoids are heavily oxygenated lactones that include the following twenty carbon skeleton, ##STR1## conventionally termed picrasane, although eighteen, nineteen, and twenty-five carbon skeletons are also known. Many variant ring structures and sidechains, particularly at C-15, are known (See eg. Polonsky, "Quassinoid Bitter Principles II", Fortschr.Chem.Org Naturst, Progress in the Chemistry of Organic Natural Products, 1985, 47, 221). The present invention includes both novel and synthetically derived quassinoid analogs, as well as novel uses for such synthetic quassinoids and previously identified and isolated natural quassinoids. In one aspect of the present invention, disclosed is a compound characterized by the formula ##STR2## wherein R.sub.1 represents hydrogen, oxygen, alkyl, alkenyl, acyl, aryl, halogen, sulfo, nitro, carboxyl, hydroxyl, hydroxyalkyl, alkoxy, or other water soluble sidechain, and Y is a sidechain comprising hydrogen, alkyl, hydroxyalkyl, carboxyl, aryl, alkenyl, cycloalkanes, cycloalkenes, glycosaccharides, water soluble sidechains, amino acid, peptide, and any of the foregoing attached at C-15 by an ether, ester, carbonyl, or glycosidic linkage.
In preferred embodiments, the sidechain Y is represented by the formula ##STR3## wherein R.sub.2, R.sub.3, and R.sub.4 taken separately or together represent hydrogen, alkyl, hydroxyalkyl, carboxyl, aryl, alkenyl, cycloalkanes, cycloalkenes, glycine, glycosaccharides, water soluble sidechains, amino acids, peptide, and any of the foregoing attached to the central carbon by an ether, ester, carbonyl, or glycosidic linkage.
Specific embodiments of the present invention include those wherein R.sub.2 is a methyl group, R.sub.3 is a methyl group, and R.sub.4 is a hydroxyl group, those wherein R.sub.2 is a methyl group, R.sub.3 is a methyl group, and R.sub.4 is a hydroxyalkane, hydroxyalkene, glycyl, glycosaccharides, or water soluble sidechain, or those wherein R.sub.2 is an ethyl group, R.sub.3 is a hydroxyl group, and R.sub.4 is an ethyl group. In addition, compounds wherein R.sub.2 is a methyl group, R.sub.3 is a methyl group, and R.sub.4 is a hydroxymethyl group, or wherein R.sub.2 is a methyl group, R.sub.3 is a methyl group, and R.sub.4 is a methyl group are included in the scope of the present invention.
Alternatively, the Y sidechain of Formula III above can be modified to support ring structures such as aryls or cycloalkanes. For example, R.sub.2 and R.sub.3 taken together can form a C.sub.3 to C.sub.8 membered carbon ring, and R.sub.4 substituted with a hydroxymethyl group. More specifically, R.sub.2 and R.sub.3 can be taken together form a three membered cycloalkane, with R.sub.4 being a hydroxymethyl group.
In still other embodiments, the sidechain Y can be represented as ##STR4## wherein R.sub.5, R.sub.6, and R.sub.7 taken separately or together represent hydrogen, alkyl, hydroxyalkyl, carboxyl, aryl, alkenyl, cycloalkanes, cycloalkenes, glycine, glycosaccharides, or water soluble sidechains, amino acids, peptide, and any of the foregoing attached to the terminal carbon by an ether, ester, carbonyl, or glycosidic linkage.
More specifically, embodiments of the present invention wherein R.sub.5 is an isopropyl group, R.sub.6 is an isopropyl group, and R.sub.7 is a hydroxyl group; wherein R.sub.5 and R.sub.6 taken together comprise a double bonded carbon group, and R.sub.7 is a methyl group; or wherein R.sub.5 is a hydrogen, R.sub.6 is a hydrogen, and R.sub.7 is a carboxyl group are contemplated as within the scope of
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Pierre et
Corbett Thomas H.
Grieco Paul A.
Morre D. James
Valeriote Frederick A.
Advanced Research And Technology Institute, Inc.
Burn Brian M.
Purdue Reseach Foundation
The Board of Governors of Wayne State University
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