Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-03-10
2001-10-30
Carr, Deborah D. (Department: 1621)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S320000, C504S321000, C504S325000, C554S103000, C554S104000, C554S213000, C554S219000, C554S223000, C554S224000, C554S225000, C554S229000
Reexamination Certificate
active
06310007
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a novel trihydroxy unsaturated fatty acid, 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD), which is produced from ricinoleic acid by
Pseudomonas aeruginosa
strain PR3.
2. Description of the Prior Art
Microbial conversions of unsaturated fatty acids have been widely exploited to produce new, value-added products. Hou, (C. T Hou, “Microbial Oxidation of Unsaturated Fatty Acids”,
Advances in Applied Microbiology
Vol. 41, pp. 1-23, 1995) recently reviewed the work on some biological oxidation systems. Wallen et al., (L. L. Wallen et al., “The Microbiological Production of 10-Hydroxystearic Acid from Oleic acid”,
Arch. Biochem. Biophys.
99:249-253, 1962) reported the first bioconversion of oleic acid to 10-hydroxystearic acid by a Pseudomonad. The bioconversion of fatty acids to produce mono-, di-, and tri-hydroxy unsaturated fatty acids has also been found (A. C. Lanser et al., “Production of 15-, 16- and 17-Hydroxy-9-Octadecenoic Acid from Oleic Acid with
Bacillus pumilus”, J. Am. Oil Chem. Soc.
69:363-366, 1992), (C. T. Hou et al., “A Novel Compound, 7,10-Dihydroxy-8(E)-Octadecenoic Acid from Oleic Acid by Bioconversion”,
J. Am. Oil Chem. Soc.
68:99-101, 1991), (C. T. Hou et al., “Production of a New Compound, 7,10-Dihydroxy-8(E)-Octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3”,
J. Indust. Microbial.
7:123-130, 1991) and (C. T. Hou et al., “A Novel Compound, 12,13,17-Trihydroxy-9(Z)-Octadecenoic Acid, from Linoleic Acid by a New Microbial Isolate Clavibacter sp. ALA2”,
J. Am. Oil Chem. Soc.
73:1359-1362, 1996). The production of a novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) from oleic acid by strain PR3 has been described most extensively. Under optimal conditions, the yield of bioconversion is greater than 60%, (C. T. Hou et al., “Production of a New Compound, 7,10-Dihydroxy-8(E)-Octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3”,
J. Indust. Microbiol.
7:123-130, 1991). PR3 is a strain of
Pseudomonas aeruginosa
, and its DOD production is inversely correlated with the accumulation of phenazine 1-carboxylic acid (PCA), (C. T. Hou et al., “Identification of NRRL Strain B-18602 (PR3) as
Pseudomonas Aeruginosa
and Effect of Phenazine-1-Carboxylic Acid Formation on 7,10-Dihydroxy-8(E)-Octadecenoic Acid Accumulation”,
World J. Microbiol. Biotechnol.
9:570-573, 1993). The production of DOD and PCA by strain PR3, however, was not consistent, and studies were conducted to stabilize and maximize cultures for the bioconversion of oleic acid.
Oxygenated metabolites of unsaturated fatty acids play a variety of important roles in biological systems. Enzymatic conversion of lipid hydroperoxides to trihydroxy fatty acids has been reported in many higher plants, (B. A. Vick et al., “Oxidative Systems for Modification of Fatty Acids: The Lipoxygenase Pathway”,
The Biochemistry of Plants: A Comprehensive Treatise
Vol. 9, pp.53-90, 1987). 8,9,13-Trihydroxy docosanoic acid is an extracellular lipid component in yeast, (F. H. Stodola et al., “8,9,13-Trihydroxydocosanoic Acid, an Extracellular Lipid Produced by a Yeast”,
Biochemistry
4:1390-1394, 1965). 9,10,13-Trihydroxy-11(E)- and 9,12,13-trihydroxy-10(E)-octadecenoic acids were detected in beer, (A. Graveland, “Enzymatic Oxidations of Linoleic Acid and Glycerol-1-Monolinoleate in Doughs and Flour-Water Suspensions”,
J. Am. Oil Chem. Soc.
47:352-361, 1970) and presumably resulted from converting linoleic acid during the barley malting process, (C. Baur et al., “Investigation about the Taste of Di-,Tri- and Tetrahydroxy Fatty Acids”,
Z. Lebensm. Unters. Forsch.
165:82-84, 1977). Trihydroxy unsaturated fatty acids, 9S,12S,13S-trihydroxy-10-octadecenoic acid and 11,12,13-trihydroxy-9(Z),15(Z)-octadecadienoic acid, isolated from rice plants with blast disease, exhibited antifungal activity, (T. Kato et al., “Structure and Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids in Rice Plant Suffering from Rice Blast Disease”,
Tetrahedron Lett.
26:2357-2360, 1985), (H. Suemune et al., “Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids Isolated from Rice Plants Suffering from Rice Blast Disease”,
Chem. Pharm. Bull.
36:3632-3637, 1988), (B. Gosse-Kobo et al., “Total Synthesis of Unsaturated Trihydroxy C-18 Fatty Acids”,
Tetrahedron Lett.
30:4235-4236, 1989) and (T. Kato et al., “Structure and Synthesis of 11,12,13-Trihydroxy-9(Z), 15(Z)-Octadecadienoic Acids from Rice Plant Suffering Rice Blast Disease”,
Chem Lett.
27:577-580, 1986). 9,12,13-Trihydroxy-10(E)-octadecenoic acid was also isolated from
Colocasia antiguorum
inoculated with
Ceratocystis fimbriata
and was shown to possess anti-black rot fungal activity, (H. Masui et al., “An Antifungal Compound, 9,12,13-Trihydroxy-(E)-10-Octadecenoic Acid, from
Colocasia antiguorum
Inoculated with
Ceratocystis fimbriata”, Phytochemistry
28:2613-2615, 1989). Recently, Hou, (C. T. Hou et al., “A Novel Compound, 12,13,17-Trihydroxy-9(Z)-Octadecenoic Acid, from Linoleic Acid by a New Microbial Isolate Clavibacter sp. ALA2”,
J. Am. Oil Chem. Soc.
73:1359-1362, 1996) reported the first production of a trihydroxy unsaturated fatty acid, 12,13,17-trihydroxy-9(Z)-octadecenoic acid (THOA), by microbial transformation of linoleic acid with Clavibacter sp. ALA2.
SUMMARY OF THE INVENTION
We have now discovered that
Pseudomonas aeruginosa
strain PR3 is one of several
P. aeruginosa
strains to produce a novel compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD) from ricinoleic acid. TOD and its derivatives have activity in controlling biological organisms such as fungal diseases and insect pests. TOD is useful in field-control of certain diseases and pests on crops, and also in stored grains and other agricultural commodities.
In accordance with this discovery, it is an object of the invention to provide a novel chemical compound, TOD and derivatives thereof.
It is also an object of the invention to produce TOD from ricinoleic acid by bioconversion with
P. aeruginosa.
It is a further object of the invention to provide a novel selective antifungal agent useful for controlling fungus growth and fungal metabolite production in field crops and in stored agricultural commodities.
Another object of the invention is to provide a selective insect control agent.
Other objects and advantages of the invention will be readily apparent from the ensuing description.
DEPOSIT OF BIOLOGICAL MATERIAL
Pseudomonas aeroginosa
strain PR3 was deposited under the terms of the Budapest Treaty in the USDA, Agricultural Research Service Patent Culture Collection in Peoria, Ill., on Jan. 30, 1990, and has been assigned Accession No. NRRL B-18602. All restrictions on the availability of this deposit have been removed.
REFERENCES:
patent: 4151817 (1979-05-01), Mueller
patent: 4205634 (1980-06-01), Tourtelot, Jr.
patent: 4498352 (1985-02-01), Hedelin
patent: 4522085 (1985-06-01), Kane
patent: 4770060 (1988-09-01), Elrod et al.
patent: 4771742 (1988-09-01), Nelson et al.
patent: 4887563 (1989-12-01), Ishida et al.
patent: 4917058 (1990-04-01), Nelson et al.
patent: 5136887 (1992-08-01), Elrod et al.
patent: 5161429 (1992-11-01), Elrod et al.
patent: 5553573 (1996-09-01), Hara et al.
patent: 5622144 (1997-04-01), Nakamura et al.
patent: 5852196 (1998-12-01), Hou
Kuo et al, JAOCS, vol. 75(7), pp. 875-879, May 1998.*
A Naturally Aspirated Miller Cycle Gasoline Engine—Its Capability of Emission, Power and Fuel Economy, SAE Technical Paper Series, No. 960589, Feb. 26-29, 1996.
An Initial Study of Variable Valve Timing Implemented with a Secondary Valve in the Intake Runne, SAE Technical Paper Series, No. 960590, Feb. 26-29, 1996.
Controlling Engine Load by Means of Late Intake-Valve Closing, SAE Technical Paper Series, No. 800794, Jun. 9-13, 1980.
Effects of Intake-Valve Closing Timing on Spark-Ignition Engine Combustion, SAE Technical Paper Series, No. 850074, Feb. 25-Mar. 1, 1985.
T.M. Kuo et al, “Fatty Acid Bioconversions byPseudomonas aeruginosaPR3”American Oil Chemists Society 89thAnnual
Hou Ching T.
Kuo Tsung Min
Carr Deborah D.
Fado John D.
Ribando Curtis P.
Silverstein M. Howard
The United States of America as represented by the Secretary of
LandOfFree
7,10,12-trihydroxy-8(E)-octadecenoic acid and derivatives... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 7,10,12-trihydroxy-8(E)-octadecenoic acid and derivatives..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 7,10,12-trihydroxy-8(E)-octadecenoic acid and derivatives... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2570181