Structural characterization,in vivo toxicity and biological activity of two new pyro-type diterpenoid alkaloids derived from 3-acetylaconitine |
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| Institution: | 1. School of Ethnic Medicine, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, Sichuan Province, China;2. School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, Sichuan Province, China;1. Department of Persian Medicine, School of Medicine, Shiraz University of Medical Sciences, Shiraz 7134845794, Iran;2. Department of Traditional Medicine, School of Persian Medicine, Tehran University of Medical Sciences, Tehran 1417613151, Iran;3. Department of History of Medicine, School of Traditional Medicine, Tehran University of Medical Sciences, Tehran 1417613151, Iran;4. International School, Beijing University of Chinese Medicine, Beijing 100029, China;5. Alkali Life Center, Healthy Life & Consultancy and Education, Ataşehir-İstanbul 34750, Turkey;6. Research Center for Traditional Medicine and History of Medicine, Department of Persian Medicine, School of Medicine, Shiraz University of Medical Sciences, Shiraz 7134845794, Iran;1. School of Pharmacy, Wingate University, Wingate, NC 28174, USA;2. Applied Science and Technology Department, North Carolina State University of Agriculture and Technology, Greensboro, NC 27411, USA;3. College of Nursing, University of Colorado Anschutz Medical Campus, Aurora, CO 80045, USA;4. Collage of Arts and Science, Department of Chemistry and Physics, Wingate University, Wingate, NC 28174, USA;1. Department of Meridian & Acupoint, College of Korean Medicine, Kyung Hee University, Seoul 02447, Republic of Korea;2. WHO Collaborating Center for Traditional Medicine, East-West Medical Research Institute, Kyung Hee University, Seoul 02447, Republic of Korea;3. Department of Meridian and Acupoint, College of Korean Medicine, Sang Ji University, Wonju 26339, Republic of Korea;1. Department of Rehabilitation, Changhai Hospital, Naval Medical University, Shanghai 200433, China;2. Department of Traditional Chinese Medicine, The 920th Hospital of Joint Logistics Support Force, Kunming 650000, Yunnan Province, China;3. Second Team, Graduate School, Naval Medical University, Shanghai 200433, China;4. College of Integrated Traditional Chinese and Western Medicine, Nanjing University of Traditional Chinese Medicine, Nanjing 210023, Jiangsu Province, China;5. Department of Military Traditional Chinese Medicine, Faculty of Traditional Chinese Medicine, Naval Medical University, Shanghai 200433, China;1. Traditional Chinese Medicine Epigenomics Research Center, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China;2. Department of Rheumatology and Immunology, Nanjing Lishui District Hospital of Traditional Chinese Medicine, Nanjing 211299, Jiangsu Province, China;3. Department of Rheumatology and Immunology, Yangzhou University Medical College, Yangzhou 225000, Jiangsu Province, China;4. Department of Cardiovascular Physiology, Faculty of Medicine, Kagawa University, Kita-gun, Kagawa 761-0793, Japan;5. Department of Gastroenterology, Yueyang Hospital of Integrated Traditional Chinese and Western Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 200437, China |
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| Abstract: | ObjectiveThe transformations that occur in diterpenoid alkaloids during the process of sand frying for Chinese herbal medicine preparation have yet to be clarified. This study investigated the structural changes that take place in 3-acetylaconitine during a simulation of heat-processing and evaluated the toxicity and biological activity of the pyrolysis products.MethodsThe diterpenoid alkaloid 3-acetylaconitine was heated at 180 °C for 15 min to simulate the process of sand frying. The pyrolysis products were separated using column chromatography, and their structures were investigated using high-resolution electrospray ionization mass spectroscopy and nuclear magnetic resonance spectroscopy. Further, in vivo cardiotoxicity and acute toxicity of 3-acetylaconitine and its pyrolysis products were compared, and the aconitine-induced arrhythmia model was employed to evaluate the antiarrhythmic effect of the pyrolysis products.ResultsTwo new diterpenoid alkaloids, pyroacetylaconitine and 16-epi-pyroacetylaconitine, a pair of epimers at C-16, were isolated. After comparing the structures of these compounds, possible transformation pathways were proposed. Compared with the prototype compound, 3-acetylaconitine, the cardiotoxicity and acute toxicity of the heat-transformed products were significantly decreased. In the biological activity assay, the two pyrolysis products exhibited an effective increase in ventricular premature beat latency, a reduction in the occurrence of ventricular tachycardia, as well as an increase in the rate of arrhythmia inhibition, implying strong antiarrhythmic activity.ConclusionCompared with 3-acetylaconitine, its pyrolysis products displayed lower toxicity and good antiarrhythmic effects; thus, they have potential for being developed into antiarrhythmic medicines.Please cite this article as: Wang YJ, Wang Y, Tao P. Structural characterization, in vivo toxicity and biological activity of two new pyro-type diterpenoid alkaloids derived from 3-acetylaconitine. J Integr Med. 2023; 21(3): 302–314. |
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| Keywords: | 3-Acetylaconitine Acute toxicity Antiarrhythmic agents 16-Epi-pyroacetylaconitine Pyroacetylaconitine Processing |
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