Benzaldehyde is a precursor of phenylpropylamino alkaloids as revealed by targeted metabolic profiling and comparative biochemical analyses in Ephedra spp. |
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| Institution: | 1. Department of Aromatic, Medicinal and Spice Crops, Newe Ya’ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel;2. Albert Katz Department of Dryland Agriculture, The Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Sede Boqer 84990, Israel;3. Department of Biology, University of Haifa-Oranim, Tiv’on 36006, Israel;4. Department of Biological Sciences, University of Calgary, Calgary, Alberta, Canada;5. Department of Biology, Western University, London, Ontario, Canada;6. Southern Crop Protection and Food Research Centre, Agriculture and Agri-Food, Canada;7. Department of Pharmacology, School of Pharmacy, Faculty of Health Sciences, Ben-Gurion University of the Negev, P.O. Box 653, Beer-Sheva 84105, Israel;8. The Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, P.O. Box 653, Beer-Sheva, Bergman Campus 84105, Israel;1. UCIBIO, REQUIMTE, Laboratory of Toxicology, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal;2. UFP Energy, Environment and Health Research Unit (FP-ENAS), University Fernando Pessoa, Praça Nove de Abril, 349, 4249-004, Porto, Portugal;1. School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, PR China;2. Guangdong Provincial Key Laboratory of Chinese Medicine Pharmaceutics, Southern Medical University, Guangzhou 510515, PR China;3. Department of Pharmacy, People''s Hospital of Xishuangbanna Prefecture, Jinghong 666100, PR China;1. Chung-Yeon Korean Medicine Hospital, Gwangju, Republic of Korea;2. Chung-Yeon Central Institute, Gwangju, Republic of Korea;3. Dongshin Korean Medicine Hospital, Seoul, Republic of Korea;4. Jaonmi Korean Medicine Clinic, Seoul, Republic of Korea;5. Department of Pharmacology, College of Korean Medicine, Kyung Hee University, Seoul, Republic of Korea;1. Department of Forensic Science, Fujian Police College, Fuzhou, PR China;2. School of Life and Environmental Sciences, Faculty of Science Engineering, Deakin University, Geelong, Australia;1. Department of Chemistry, Annamalai University, Annamalainagar 608002, Tamilnadu, India;2. Mathematics Wing, DDE, Annamalai University, Annamalainagar 608002, Tamilnadu, India |
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| Abstract: | Ephedrine and pseudoephedrine are phenylpropylamino alkaloids widely used in modern medicine. Some Ephedra species such as E. sinica Stapf (Ephedraceae), a widely used Chinese medicinal plant (Chinese name: Ma Huang), accumulate ephedrine alkaloids as active constituents. Other Ephedra species, such as E. foeminea Forssk. (syn. E. campylopoda C.A. Mey) lack ephedrine alkaloids and their postulated metabolic precursors 1-phenylpropane-1,2-dione and (S)-cathinone. Solid-phase microextraction analysis of freshly picked young E. sinica and E. foeminea stems revealed the presence of increased benzaldehyde levels in E. foeminea, whereas 1-phenylpropane-1,2-dione was detected only in E. sinica. Soluble protein preparations from E. sinica and E. foeminea stems catalyzed the conversion of benzaldehyde and pyruvate to (R)-phenylacetylcarbinol, (S)-phenylacetylcarbinol, (R)-2-hydroxypropiophenone (S)-2-hydroxypropiophenone and 1-phenylpropane-1,2-dione. The activity, termed benzaldehyde carboxyligase (BCL) required the presence of magnesium and thiamine pyrophosphate and was 40 times higher in E. sinica as compared to E. foeminea. The distribution patterns of BCL activity in E. sinica tissues correlates well with the distribution pattern of the ephedrine alkaloids. (S)-Cathinone reductase enzymatic activities generating (1R,2S)-norephedrine and (1S,1R)-norephedrine were significantly higher in E. sinica relative to the levels displayed by E. foeminea. Surprisingly, (1R,2S)-norephedrine N-methyltransferase activity which is a downstream enzyme in ephedrine biosynthesis was significantly higher in E. foeminea than in E. sinica. Our studies further support that benzaldehyde is the metabolic precursor to phenylpropylamino alkaloids in E. sinica. |
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