Tropane alkaloid metabolism by Pseudomonas AT3 cell cultures: Interchange between the nortropine and norpseudotropine catabolic pathways |
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| Institution: | 1. Elucidation of Biosynthesis by Isotopic Spectrometry Group, Unit for Interdisciplinary Chemistry: Synthesis-Analysis-Modelling (CEISAM), University of Nantes-CNRS UMR6230, 2, rue de la Houssinière, 44322 Nantes, France;2. Multistep Synthesis and Bioscience Group, Unit for Interdisciplinary Chemistry: Synthesis-Analysis-Modelling (CEISAM), University of Nantes-CNRS UMR6230, 2, rue de la Houssinière, 44322 Nantes, France;1. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, People''s Republic of China;2. JNU-HKUST Joint Laboratory for Neuroscience & Innovative Drug Research, Jinan University, Guangzhou 510632, People''s Republic of China;3. College of Pharmacy, Wannan Medical College, Wuhu 241000, People''s Republic of China;1. Laboratory of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon;2. School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, I-62032 Camerino, Italy;3. Laboratoire de Pharmacognosie, UFR des Sciences de Santé (Pharmacie), EA 4267 (FDE/UFC), Université de Bourgogne, 7, Boulevard Jeanne d’Arc, BP 87900, 21079 Dijon Cedex, France;4. School of Pharmacy, Physiology Division, University of Camerino, Via Gentile III da Varano, I-62032 Camerino, Italy;1. Qilu University of Technology, Key Laboratory of Pulp & Paper Science and Technology, Jinan 250353, PR China;2. Laboratory of Soft Materials & Green Chemistry, North Carolina State University, Department of Forest Biomaterials, Raleigh, NC 27695-8005, United States;3. Laboratory of Soft Materials & Green Chemistry, North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, United States;1. Faculty of Pharmacy, Umm Al-Qura University, Makka, Saudi Arabia;2. Faculty of Pharmacy (Girls), Al-Azhar University, Nasr-City, Cairo, Egypt;3. Faculty of Pharmacy, Egyptian-Russian University, Cairo, Egypt;4. National Organization for Drug Control and Research, Dokki, P.O. 29, Cairo, Egypt |
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| Abstract: | Selected strains of Pseudomonas bacteria can degrade tropane alkaloids to obtain both nitrogen and carbon for growth. In order to probe the mechanisms of the catabolic enzymes involved, the metabolic process responsible for the opening of the 8-azabicyclo3.2.1]octan-3-ol ring of nortropane alkaloids has been explored. It is found that the bacteria contain considerable flexibility in their enzyme complement and can convert (3-endo)-8-azabicyclo3.2.1]octan-3-ol) (nortropine (2) to (3-exo)-8-azabicyclo3.2.1]octan-3-ol) (norpseudotropine). Both of these compounds can serve as substrates for the catalytic cascade. In order to establish the proportionation between direct and indirect pathways, metabolism has been probed by competitive substrate availability and by incorporation of stable heavy labels into substrate pools. The results indicate that, while norpseudotropine is almost entirely metabolized directly, nortropine is partitioned c. 4:1 between direct and indirect catabolism. |
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| Keywords: | Nor(pseudo)tropine catabolism Stable isotope label |
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