Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation |
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| Institution: | 1. Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute, ul. Czartoryskich 8, 24-100 Puławy, Poland;2. Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoléculas (INBIO), Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real (Cádiz), Spain;1. Shandong Analysis and Test Center, Shandong Academy of Sciences, Jinan 250014, P. R. China;2. Reyoung Pharmaceutical Co., Ltd, No. 44 Cultural West Road, Jinan 250012, P. R. China;1. Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China;2. Jiangzhong Pharmaceutical Group Company Limited, Nanchang 330096, China;3. State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;4. Graduate School of Medicine and Pharmaceutical Sciences for Research, University of Toyama, Toyama 930-0194, Japan;1. Hematology Division, Tokyo Metropolitan Cancer and Infectious Diseases Center, Komagome Hospital, Japan;2. Department of Clinical Laboratory, Tokyo Metropolitan Cancer and Infectious Diseases Center, Komagome Hospital, Japan;3. Department of Radiology, Tokyo Metropolitan Cancer and Infectious Diseases Center, Komagome Hospital, Japan;1. Department of Neurosurgery and Neurotraumatology, Saint Edvige Provincial Hospital No. 2 in Rzeszow, Lwowska 60, 35-301 Rzeszów, PL, Poland;2. Department of Medical Chemistry, Medical University of Lublin, Chodźki 4, 20-093 Lublin, PL, Poland;3. Department of Maxillofacial Surgery, Medical University of Lublin, Poland;1. Shaanxi Collaborative Innovation Center of Chinese Medicinal Resource Industrialization, Shaanxi Province Key Laboratory of New Drugs and Chinese Medicine Foundation Research, Shaanxi Rheumatism and Tumor Center of TCM Engineering Technology Research, School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang 712046, China |
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| Abstract: | Four triterpenoid saponins (1–4) were isolated from the aerial parts of Trifolium argutum Sol. (sharp-tooth clover) and their structures were elucidated by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Two of them are new compounds, characterized as 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (1) and 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (2). The occurrence of 3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (melilotigenin) in its natural form is reported for the first time as a triterpenoid aglycone within Trifolium species. The phytotoxicity of compounds was evaluated on four STS at concentration 1 μM to 333 μM. Compound 1 was the most active, showing more than 60% inhibition on the root growth of L. sativa at the higher dose, with IC50 (254.1 μM) lower than that of Logran® (492.6 μM), a commercial herbicide used as positive control. The structure–activity relationships indicated that both aglycones and glycosidic parts may influence the phytotoxicity of saponins. |
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| Keywords: | Triterpenoid saponins Structural elucidation Phytotoxic activity Structure–activity relationship |
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