Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-08-08
1998-12-15
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568338, 514691, 514729, C07C 49307
Patent
active
058499563
DESCRIPTION:
BRIEF SUMMARY
This is the U. S. National Stage Application of PCT/JP96/00259 filed Feb. 7, 1996 now WO96/24681 published Aug. 15, 1996.
TECHNICAL FIELD
The present invention relates to phytocassanes which are rice phytoalexins and are novel diterpene compounds exhibiting an antifungal activity against rice blast fungus, Pyricularia oryzae (Magnaporthe grisea) and rice sheath blight fungus, Rhizoctonia solani, and more specifically, it relates to phytocassanes A, B, C and D. Phytocassanes A, B, C and D according to the present invention have a high antifungal activity against Pyricularia oryzae and Rhizoctonia solani and are useful for protecting rice plants from rice blast and rice sheath blight.
In addition, the present invention relates a process for producing phytocassanes or momilactones, antifungal diterpene compounds, at a high yield comprising adding cellular extracts of plant pathogenic fungi such as Pyricularia oryzae or potato pathogenic fungi to the liquid culture medium of rice calluses to yield phytocassanes and momilactones, diterpene compounds exhibiting an antifungal activity against Pyricularia oryzae and so forth and then separating the product.
Further, the present invention relates to phytocassane EL, a novel diterpene compound having an activity of deriving phytoalexins extracted from rice plants; more specifically, it relates to phytocassane EL having an activity of deriving the formation of phytoalexins in rice plants and exhibiting an antifungal activity against Pyricularia oryzae and Rhizoctonia solani itself, and a process for producing the same, and low-toxic and harmless rice disease control drugs free from so-called residual toxicity. Since phytoalexins have a high antifungal activity against these pathogenic fungi, they can prevent rice plants from being infected with Pyricularia oryzae and Rhizoctonia solani by applying phytocassane EL according to the present invention onto rice plants.
TECHNICAL BACKGROUND
Plants perform self-defense against various kinds of stress causing diseases such as the invasion of pathogenic fungi, actions by ultraviolet rays and heavy metals and injuries, according to various kinds of resistance mechanism. As physiologically active substances concerned in such a disease resistance reaction of plants can be mentioned antifungal substances and plant hormones. Of them, the former inhibits the growth of pathogenic fungi directly, while the latter is concerned in the expression of symptoms of a disease.
As antifungal substances of plants, various types have been reported; they are generally classified into four groups according to the expression mechanism, namely, prohibiting, inhibiting, post inhibitins and phytoalexins. Of them, prohibitins are antifungal substances being present at a sufficient concentration on a sound plant tissue; inhibitins are antifungal substances being present at a low concentration on a sound plant tissue and the concentration thereof increases after they are infected with pathogenic fungi, and post inhibitins are substances being present on a sound plant tissue and exhibiting an antifungal activity according to a simple chemical change thereof when they are invaded with pathogenic fungi though they exhibit no antifungal activity as they are. These three substances are considered to be pre-antifungal substances. In contrast, phytoalexins are antifungal substances being absent on a sound plant tissue and being derived and synthesized after they are infected with pathogenic fungi, and being dynamic defense substances playing an important role in a plant disease resistance reaction.
It is known that plants show an antibiotic reaction (hypersensitive reaction) when they come into contact with pathogenic fungi and yield phytoalexins having an antifungal activity against the pathogenic fungi on a tissue surrounding the reaction site. The antifungal activity of these phytoalexins itself is not so high, but it is thought that they exhibit an antifugnal activity when they are transferred to a disease part and are present at a high concentratio
REFERENCES:
Koga et al, Tetrahedron, vol. 51, #29, pp. 7907-7918, 1995.
Bohlmann et al; Phytochemistry, vol. 22, #07, pp. 1645-1651, 1983.
Koga et al, Phytochemistry, vol. 44, #02, pp. 249-253, 1997.
D. Cartwright et al, "Chemical Activation of Host Defence Mechanisms as a Basis for Crop Protection", Nature, vol. 267, Jun. 9, 1977, pp. 511-513.
T. Akatsuka et al, "3-Hydroxy-7-oxo-sandaracopimaradiene (Oryzalexin A), a New Phytoalexin Isolated from Rice Blast Leaves", Agric. Biol. Chem., vol. 47, No. 2, 1983, pp. 445-447.
Y. Kono et al, "Absolute Configuration of Oryzalexin A and Structures of Its Related Phytoalexins Isolated from Rice Blast Leaves Infected with Pyricularia oryzae", Agric. Biol. Chem., vol. 48, No. 1, 1984, pp. 253-255.
T. Akatsuka et al, "Novel Phytoalexins (Oryzalexins A,B and C) Isolated from Rice Blast Leaves Infected with Pyricularia oryzae. Part l: Isolation, Characterization and Biological Activities of Oryzalexins", Agric. Biol. Chem., vol. 49, No. 6, 1985, pp. 1689-1694.
Y. Kono et al, "Novel Phytoalexins (Oryzalexins A, B and C) Isolated from Rice Blast Leaves Infected with Pyricularia oryzae. Part ll: Structural Studies of Oryzalexins", Agric. Biol. Chem., vol. 49, No. 6, 1985, 1695-1701.
H. Sekido et al, "Oryzalexin D (3,7-Dihydroxy-(+)-sandaracopimaradiene), a New Phytoalexin Isolated from Blas-infected Rice Leaves", J. Pesticide Sci., vol. 11, 1986, pp. 369-372.
H. Kato et al, "Oryzalexin E, A Diterpene Phytoalexin from UV-Irradiated Rice Leaves", Phytochemistry, vol. 33, No. 1, 1993, pp. 79-81.
H. Kato et al, "Oryzalexin F, A Diterpene Phytoalexin from UV-Irradiated Rice Leaves", Phytochemistry, vol. 36, No. 2, 1994, pp. 299-301.
O. Kodama et al, "Oryzalexin S, a Novel Stemarane-type Diterpene Rice Phytoalexin", Biosci. Biotech. Biochem., vol. 56, No. 6, 1992, pp. 1002-1003.
O. Kodama et al, "Sakuranetin, a Flavanone Phytoalexin from Ultraviolet-Irradiated Rice Leaves", Phytochemistry, vol. 31, No. 11, 1992, pp. 3807-3809.
M. Watanabe et al, "Novel C.sub.19 -Kaurane Type of Diterpene (Oryzalide A), a New Antimicrobial Compound Isolated from Healthy Leaves of a Bacterial Leaf Blight-resistant Cultivar of Rice Plant", Agric. Biol. Chem., vol. 54, No. 4, 1990, pp. 1103-1105.
Y. Kono et al, "Structures of Oryzalides A and B, and Oryzalic Acid A, A Group of Novel Antimicrobial Diterpenes, Isolated from Healthy Leaves of a Bacterial Leaf Blight-resistant Cultivar of Rice Plant", Agric. Biol. Chem., vol. 55, No. 3, 1991, pp. 803-811.
M. Watanabe et al, "Structures of Oryzalic Acid B and Three Related Compounds, a Group of Novel Antibacterial Diterpenes, Isolated from Leaves of a Bacterial Leaf Blight-Resistant Cultivar of Rice", Biosci. Biotech. Biochem., vol. 56, No. 1, 1992,pp. 113-117.
F. Bohlmann et al, "Diterpenes and Sesquiterpenes from Osteospermum Species", Phytochemistry, vol. 22, No. 7, 1983, pp. 1645-1651.
Koga Jinichiro
Ogasawara Nagakatsu
Ogasawara Yoko
Shimura Masaru
Suzuki Jyunko
Killos Paul J.
Padmanabhan Sreeni
Plant Biological Defense System Laboratories
LandOfFree
Antifungal terpene compounds and process for producing the same does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Antifungal terpene compounds and process for producing the same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antifungal terpene compounds and process for producing the same will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1459712