Use of phyllocladane diterpenoids for plant growth promotion...

Details Use of phyllocladane diterpenoids for plant growth promotion... Use of phyllocladane diterpenoids for plant growth promotion...

2002-12-31

2004-01-06

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S353000

Reexamination Certificate

active

06673749

ABSTRACT:

FIELD OF THE INVENTION
The present invention provides plant growth-promoting activities of natural plant active constituent, calliterpenone and its derivatives belonging to the group phyllocladane diterpenoids. These phytochemicals and derivatives exhibit remarkable growth promoting activities on plant roots, shoots and promote seed germination both in monocotyledonous and dicotyledonous plants. These phytomolecules also possess antagonistic activity against allelochemicals of plant growth retardant nature and hence can be used to alleviate their detrimental effects.
BACKGROUND OF THE INVENTION
Auxins and gibberellins are two main classes of natural compounds discovered simultaneously as plant growth stimulants. Besides these, cytokinins, abscisic acid, ethylene and many other compounds are also reported to possess plant growth regulatory properties. So far, more than 50 gibberellins have been discovered from natural sources. The growth stimulating activity has also been observed in several other types of natural plant constituents. Kaurenoic acid and steviol have been reported to be naturally occurring compounds having gibberellin like activity (Srivastava HS. 1999. Elements of Biochemistry. Rastogi Publications, Shivagi Road Merrut. Pp: 245-246). Helminthosporic acids isolated from Helminthosporium sativum and phaseolic acid isolated from the bean (Phaseolus species) seeds have also showed growth promoting activities. (Leopold A. C. and Kriedemann P. E. Plant Growth and Development Tata McGraw Hill Publishing Company Ltd., New Delhi. 137-140. 1981).
In recent years many papers and patents dealing with the plant growth promoting activities of natural and synthetic compounds have appeared. Important of them are salicilic acid (H S Gehlot et al. Advances in Plant Physiology Vol-I, 273-289, 1998), trioctanol(Ries et al, Science, 195 :1339, 1977) and other compounds reported from time to time. Goyal R. et al. reported three oxygenated alantolides from
Inula racemosa
(Phytochemistry 29(7) 2341-2343, 1990), three sesquiterpenoids, Saussureal, dehydrocostus lactone and costunolide isolated from
Saussurea lappa
have also shown growth promoting activities (I. P. Singh et al. Phytochemistry 31(7) 2529-2531, 1992 & K. K. Talwar et al. Phytochemistry 31 (1) 336-338 1992).
Among the synthetic derivatives, many compounds like triazoles, have been reported as a new group of promising plant growth promoters (R. P.Raghava et al. Advances in Plant Physiology, Vol-I 291-320, 1998). Various derivatives of organic acids reported to have plant growth promoting activity (e.g. West German Patent No. 1916054 discloses uses of &agr;-hydroxy and &agr;-ketoalkanoic acid having 7-10 carbon atoms and their derivatives; U.S. Pat. No. 3, 148,049 discloses growth promoting activity of certain halogenated keto acids under drought conditions). Mikami et al. (Agr Biol Chem 1970 3 4, 977-979) reported a number of hydroxy acids as plant growth regulators. Kamuro et al.(U.S. Pat. Nos. 6,093,683; 2000; 5,776,860; 1998; 4,846,877; 1989 and 6,271,176; 2001) described the derivatives of jasmonic acids as plant growth promoters. Danzig Morris J. et al. (U.S. Pat. No. 4,806,149; 1989) disclosed that monoxanthates and dixanthates of dipropylene glycol and triethylene glycol increase the growth and concentration of chlorophyll in plants.
Thus many active compounds have been reported so far to promote growth in plants. These compounds help in the increase in sizes of fruit, root, and shoot and in the total yield of the crop. However, it is difficult to obtain these compounds in great quantities from plants and cost to prepare them synthetically will be very high.
Callicarpa macrophylla
Vahl. (Verbanaceae) is an erect shrub common to Indo-Gangetic plains and sub-Himalayan tracts from Kashmir to Assam ascending upto 2000 m. Leaves of plant are commonly used in rheumatism and aromatic root oil is given in stomach troubles. The plant has been investigated for its chemical constituents (Asolkar et al. Second supplement to Glossary of Indian Medicinal Plants with active principles, part 1. PID,CSIR, New Delhi, 155,1992).
The isolation of calliterpenone and its monoacetate from
Callicarpa macrophylla
was first reported by Chaterjee et al, Tetrahedron 28, 4319, 1972, and assigned the structure as 16&agr;, 17 dihydroxy-ent kauan-II-one and its 17-acetate. Based on chemical and spectroscopic evidences, these structures were however, revised as 16&agr;, 17 dihydroxy phyllocladan-3one and its 17-acetate on the basis further chemical ‘H NMR, NOE and LIS and X-ray crystallographic data studies by Ahmad and Zaman (Tetrahedron Lett. 2179,1973), Fujita et al (Phytochemistry 14 1975 2249) and Wong et al (Acta Crystallography Sec. C 47 1991 906). Later, this compound was also isolated from some other species of the genus Callicarpa.
During previous studies on
Callicarpa macrophylla, natural compounds
16&agr;, 17 dihydroxy phyllocladan-3 one (calliterpenone), its 17-acetate (calliterpenone monoacetate) and two related minor constituents 16&agr;, 17-isopropylidino 3-oxo phyllocladane (isopropylideno calliterpenone) and 30&bgr;, 16&agr;, 17. trihydroxy phyllocladane (trihydroxy calliterpenone) werwe isolated and diacetate derivative of calliterpenone also prepared (Singh et al. Phytochemistry 37, 1994,587 and
Indian Jour. of Chem
.33B, 1994 1205). The complete spectral assignment of all the 5 phllocladane diterpenoids have also been done (Agarwal et al.
Ind. Jour. of Chem
.35B. 1996. 803-805).
SUMMARY OF THE INVENTION
The basis of the present invention is the finding that these pyllocladane diterpenoids when used in particular concentrations behave as growth promoters. Some of these compounds on certain dilutions produce more growth enhancement than that produced by GA
3
(Gibberellic acid) in identical conditions.
The invention also provides novel growth promoting activity of phyllocladane diterpenoids like calliterpenone and derivatives isolated from plants of
Callicarpa macrophylla
and their antagonizing effects against plant growth retardants.
Further the invention also provides the effective amount of phyllocladane diterpenoids selected from calliterpenone, calliterpenone mono-acetate, calliterpenone di-acetate, isopropylidino calliterpenone and tryhydroxy calliterpenone wherein 0.001 to 0.1 &mgr;M (w/v) concentrations of the said compounds can be used as sprays or in the media in tissue cultures or soaking of seeds, roots, shoots etc in said solutions.
The said solutions are prepared by dissolving required amount in minimum amount of water/organic solvents like ethyl alcohol, methanol, propenol followed by gentle warming and then the desired concentrations are achieved by adding suitable amount of distilled water.
DETAILED DESCRIPTION OF THE INVENTION
The present invention describes the growth promoting activities of phyllocladane diterpenoids isolated from the leaves of plant
Callicarpa macrophylla
that are not only cheap but show better activity at a particular dilution than the well known growth promoting hormone Gibberellic Acid (GA
3
). In our experiment calliterpenone, its monoacetate and certain other derivatives naturally isolated from the plant
Callicarpa macrophylla
Vahl. (Verbanaceae) have shown promising growth promoting activities.
Calliterpenone(16&agr;, 17 dihydroxy phyllocladan-3 one),a phyllocladane diterpenoid, is a stereoisomer of abbeokutone (16,17 dihydroxy kauran-3-one). Abbeokutone has kauranoid skeleton while calliterpenone has phyllocladane skeleton. The antagonistic activity of these phytoderivatives against negative allelochemicals makes their utility much higher as plant growth supporting chemicals.
As noted above the activity of phyllocladane diterpenoids used in the practice of this invention was observed when these compounds were tested for their effects on seed germination, root and shoot growth of certain plant species and their antagonistic effect on plant growth retardants by the method described by Bagchi G. D. et al Phytochemistry, 45(6)1131-1133, 1997.
Since the assay involves growin

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