Chemical structure-activity relationships of the inhibition of sterol biosynthesis by N-substituted morpholines in higher plants |
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| Affiliation: | 1. Laboratoire de Biochimie Végétale, Institut de Botanique, 28, rue Goethe 67083, Strasbourg, France;2. Landwirtschaftliche Versuchstation der BASF Aktiengesellschaft, Postfach 220, D-6703, Limburgerhof, Federal Republic of Germany;1. Division of Horticulture and Forestry, ICAR – Central Island Agricultural Research Institute, Port Blair 744105, Andaman and Nicobar Islands, India;2. ICAR-Indian Institute of Spices Research, Kozhikode 673012, Kerala, India;1. Zhejiang University, College of Biosystems Engineering and Food Science, Fuli Institute of Food Science, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang R & D Center for Food Technology and Equipment, Key Laboratory for Agro-Food Risk Assessment of Ministry of Agriculture, Hangzhou 310058, China;2. School of Life Sciences, Shaoxing University, Shaoxing 312000, China;3. Food Refrigeration and Computerized Food Technology (FRCFT), School of Biosystems and Food Engineering, University College Dublin, National University of Ireland, Agriculture and Food Science Centre, Belfield, Dublin 4, Ireland;4. Zhejiang Economic & Trade Polytechnic, Department of Applied Technology, Hangzhou 310018, China;5. Institute of Quality Standard and Testing Technology for Agro-Products of CAAs, Quality Standard Research Center of Ministry of agriculture of Agro-Products, Beijing 100081, China;1. Laboratory of Botany and Plant Ecology, Faculty of Sciences of Bizerta, Jarzouna, 7021, Bizerta, University of Carthage, Tunisia;2. Silvo-Pastoral Resources Laboratory, Silvo-Pastoral Institute of Tabarka, BP. 345, Tabarka, 8110, University of Jendouba, Tunisia;3. Laboratory of Botany, Cryptogamy and Plant Biology, Faculty of Pharmacy of Monastir, BP 207, Avenue Avicenna, 5000, Monastir, University of Monastir, Tunisia;4. Research Unit 13ES63, Applied Chemistry and Environment, Monastir University, Faculty of Sciences of Monastir, Monastir, 5000, University of Monastir, Tunisia;5. Transmissible Diseases and Biologically Active Substances LR99ES27, Faculty of Pharmacy, University of Monastir, Avenue Avicenna, 5000, Monastir, Tunisia;6. Department of Phytochemistry, ICMR-National Institute of Traditional Medicine, Nehru Nagar, Belagavi, 590010, Karnataka, India |
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| Abstract: | Tridemorph and fenpropimorph as well as several related N-alkyl morpholines have been tested in vitro on the cycloeucalenol-obtusifoliol isomerase, a microsomal enzyme involved in higher plant sterol biosynthesis. The results showed that N-substituted morpholines inhibit powerfully the enzyme (I50 = 0.4 μM for fenpropimorph). The following important molecular parameters of the inhibition could be determined: (i) the inhibitory capacity was probably related to the presence of a positive charge on the nitrogen atom, (ii) the length of the alkyl group was critical, with a maximum activity for n = 13 carbons in the case of a linear hydrocarbon chain, (iii) the presence of bulky substituents at the proximity of the nitrogen atom led to a strong decrease of the inhibitory power, (iv) in the fenpropimorph series where a chiral center is present at C-2 of the alkyl chain, a remarkable enantiomeric selectivity of the inhibition was observed, (v) the N-oxide derivative of fenpropimorph was shown to be as active as the parent compound. The N-alkyl morpholines have been also assayed on suspension cultures of bramble cells and led to a strong accumulation of 9β, 19-cyclopropyl- and Δ8-sterols. This result confirmed that the cycloeucalenol-obtusifoliol isomerase was a major target of the N-substituted morpholines and suggested that the Δ8 → Δ7-sterol isomerase was also a target for these chemicals. The molecular parameters implied in the in vivo accumulation of 9β, 19-cyclopropyl sterols were very similar to those resulting from the in vitro study. The chemical structure-inhibitory activity relationship of N-alkyl morpholines was discussed with respect to their fungicidal activity which has been described in a previous study [E. H. Pommer, Pestic. Sci. 15, 285 (1984)]. The comparison revealed that the better the inhibitory capacity on the cycloeucalenol-obtusifoliol isomerase was, the higher was the fungicidal activity in vivo. |
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