Derivatives of (+)(-) limonene.  Effect of chain length in n-alkyl quaternary ammonium derivatives on plant growth retardant activity

Pieringer, A. P.; Newhall, William F.

doi:10.1021/jf60157a024

Cited by 8 publications

(5 citation statements)

References 3 publications

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“…The compounds are listed in order of decreasing inhibition. Most effective were the steroid synthesis inhibitor SKF-525A, Phosfon D and Phosfon S. These inhibitors plus Amo-1618, the steroid synthesis inhibitor SKF-3301A, and the limonene derivatives Q-64 and Q-58, also known plant growth retardants (22), were effective inhibitors of activity A at 1 ,UM.…”

Section: Methodsmentioning

confidence: 99%

Properties of Kaurene Synthetase from Marah macrocarpus

Frost¹,

West²

1977

Plant Physiol.

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The kaurene synthetase from immature seeds of Marah macrocarpus (Greene) Greene was partialy purified from cell-free homogenates of endosperm by a combination of QAE-Sephadex A-25 chromatography and hydroxyapatite chromatography and freed of contaminating phosphatase activity. The two catalytic activities associated with kaurene synthetase, the cyclization of geranylgeranyl-pyrophosphate to copalylpyrophosphate (activity A) and the cyclization of copalyl-pyrophosphate to ent-kaurene (activity B), were not even partially resolved from one another during these procedures. Both activities had identical elation profiles from a calibrated Sepharose 4B column corresponding to a molecular weight less than that of ovalbumin (45,000).The A and B activities had pH optima of 7.3 and 6.9, respectively. Both activities required millimolar concentrations of the following divalent cations in the order: Mg2+ > Mn2+ > Co2+. Activities A and B were both sensitive to inhibition by Hg2+, Cu2+, p-hydroxymercuribenzoate, and N-ethylmaleimide, but activity B was much more sensitive than activity A. The average value of Km' (apparent Km in the absence of substrate inhibition) for geranylgeranyl-pyrophosphate was 1.6 FLM. Values of 0.5 and 0.6 JFM were obtained for Km' and Km, respectively, for copalyl-pyrophosphate. The Vm' values for the two activities were similar: 12 and 9 pmol/minute p.g protein for activities A and B, respec-tively.N,N-Dimethylaminoethyl-2,2-diphenylpentanoate (SKF-525A) and N,N-dimethylaminoethyl-2,2-diphenylpentyl ether (SKF-3301A), tributyl-2,4-dichlorobenzylphosphonium chloride (Phosfon D), tributyl-2,4-dichlorobenzylammonium chloride (Phosfon S), 2'-isopropyl-4'-(trimethylammonium chloride)-5'-methylphenyl piperidine-l-carboxylate (Amo-1618), . 2-(N1N-dimethyl-N-heptylammonium bromide)-pmethan-l-ol (Q-58), and 2-(NT%-dimethyl-N-octylammonium bromide)-p-methan-1-ol (Q-64), at concentrations from 1 to 5 FLM, were effective inhibitors of kaurene synthetase activity A. Acetylcholine chloride and 2-chloroethyl-trimethylammonium chloride were effective inhibitors of activity A only at concentrations of 5 mm or greater. Absdsic acid, indole-3-acetate, gibberellin Al, gibberellin A3, a mixture of gibberellins A4 and A7, gibberellin A13, and N)V-dimethylaminosuccinamic acid (B995) were not inhibitory at any of the levels tested. None of these compounds was an effective inhibitor of activity B at concentrations less than 0.5 mM. biosynthesis has been well established (7,12,32). Cell-free enzyme systems capable of catalyzing the biosynthesis of kaurene have been obtained from a number of higher plant sources (2, 4, 5, 11-13, 26, 33) and from the gibberellin-producing fungus Fusarium moniliforme Sheld (9, 28). The biosynthesis of kaurene from the acyclic precursor trans-geranylgeranyl-PP has been shown to occur in two steps (14, 28) as follows:geranylgeranyl-PP copalyl-PP ent-kaurene The name kaurene synthetase has been used to refer to the enzyme or enzymes catalyzing the over-all reaction that is the sum of th...

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Section: Methodsmentioning

confidence: 99%

Properties of Kaurene Synthetase from Marah macrocarpus

Frost¹,

West²

1977

Plant Physiol.

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“…The effect of chain length in n-alkyl quaternary ammonium derivatives of (+)-limonene on plant growth has also been studied (Pieringer and Newhall, 1968). Two additional benzyl quaternary ammonium compounds, prepared from (+)-limonene, have been reported (Newhall and Pieringer, 1969), and their effect on the growth of citrus described (Pieringer and Newhall, 1970).…”

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confidence: 99%

“…The plant growth-retardant activity of six benzyl quaternary ammonium derivatives synthesized from the terpene (+)limonene, found abundantly in citrus peel oil, has been reported (Newhall and Pieringer, 1966). The effect of chain length in «-alkyl quaternary ammonium derivatives of (+)limonene on plant growth has also been studied (Pieringer and Newhall, 1968). Two additional benzyl quaternary ammonium compounds, prepared from (+)-limonene, have been reported (Newhall and Pieringer, 1969), and their effect on the growth of citrus described (Pieringer and Newhall, 1970).…”

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confidence: 99%

Effect of phenyl substitutents in benzyl quaternary ammonium derivatives of (+)-limonene on plant growth-retardant activity

Newhall¹

1971

J. Agric. Food Chem.

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The growth-retardant activity of 26 benzyl quaternary ammonium derivatives of (+)-limonene was evaluated using two bioassays, one based on the root growth of cucumber seed and the other on total fresh weight increase of alfalfa seeds exposed to dilute aqueous solutions of each compound. Inhibition of human blood serum cholinesterase was also determined manometrically. A highly significant correlation between serum cholinesterase inhibition and plant growth retardation found for 24 compounds on cucumber and 22 compounds on alfalfa suggests that these derivatives retard plant growth by inhibition of an enzyme system associated with a growth process. Electron withdrawing groups on the benzene ring, such as nitro and cyano, caused inactivation. A chloro group at 2 or 4 produced more activity than substitution at position 3. Monobromo and monomethyl derivatives substituted at 2 and 3 were equally active, while substitution at C-4 approximately doubled activity. The disubstituted chloro and methyl benzyl compounds were all highly active, regardless of the positions of these groupings.he ability of certain quaternary ammonium compounds to reduce stem elongation of bean plants without caus-T ing abnormal, formative changes was first reported by Mitchell et al. (1949). One of the most active compounds was a quaternary ammonium carbamate, designated Amo-1618(4-hydroxyl-5-isopropyl -2 -methylphenyltrimethylatnmonium chloride, 1-piperidine carboxylate), prepared from the terpene thymol by R. L. Shriner at the University of Illinois. Much work has been done on the synthesis and testing of derivatives ofAmo-l618 (Krewson et al., 1959). Knight et al. (1969) have studied the influence on plant growth-retardant activity of various substituents of aryl quaternary ammonium, phosfonium, and sulfonium compounds. 3-Chloro-and 4-chloro-benzyltributyl ammonium bromides were the most active compounds.The plant growth-retardant activity of six benzyl quaternary ammonium derivatives synthesized from the terpene (+)-limonene, found abundantly in citrus peel oil, has been reported (Newhall and Pieringer, 1966). The effect of chain length in n-alkyl quaternary ammonium derivatives of (+)-limonene on plant growth has also been studied (Pieringer and Newhall, 1968). Two additional benzyl quaternary ammonium compounds, prepared from (+)-limonene, have been reported (Newhall and Pieringer, 1969), and their effect on the growth of citrus described (Pieringer and Newhall, 1970).All of these limonene derivatives have somewhat different structural requirements for plant growth-retardant activity than other known growth regulants. A highly significant correlation between the plant growth-retardant activities of Florida Citrus Experiment Station, IFAS, Lake Alfred, Fla. 33850 these compounds and their ability to function as inhibitors of human blood serum (pseudo) cholinesterase has been demonstrated (Newhall, 1969).In the present study, 18 additional, new, substituted benzyl quaternary ammonium derivatives of (+)-limonene were synthesized both to det...

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“…Many examples can be found in literature on the syntheses of substituted quinolines , but there has been no systematic study on the syntheses of (monoalkyl)‐8‐aminoquinolines substituted at each alternate position of the quinoline ring. In this manuscript, a systematic study on the synthesis of 8‐aminoquinoline derivatives with an n ‐butyl group at each alternate position of the quinoline ring is presented.…”

Section: Introductionmentioning

confidence: 99%

A Systematic Study on the Synthesis of n‐Butyl Substituted 8‐Aminoquinolines

Koseoglu

Gül

Acar

2015

Journal of Heterocyclic Chem

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A systematic study on the synthesis of 8‐aminoquinoline derivatives with an n‐butyl group at each alternate position of the quinoline ring was carried out. Skraup Reaction and its Doebner–von Miller variation were used to obtain most of the quinoline ring except for the 2‐butyl‐8‐aminoquinolines and 4‐butyl‐8‐aminoquinolines where the commercially available methylquinoline derivatives were used as precursors. The structures of the synthesized compounds were characterized by FTIR, 1H‐NMR, COSY, 13C‐NMR and HRMS spectra.

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Derivatives of (+)(-) limonene. Effect of chain length in n-alkyl quaternary ammonium derivatives on plant growth retardant activity

Cited by 8 publications

References 3 publications

Properties of Kaurene Synthetase from Marah macrocarpus

Properties of Kaurene Synthetase from Marah macrocarpus

Effect of phenyl substitutents in benzyl quaternary ammonium derivatives of (+)-limonene on plant growth-retardant activity

A Systematic Study on the Synthesis of n‐Butyl Substituted 8‐Aminoquinolines

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