Methyl 2-naphthoates from a traditional Chinese herb Morinda officinalis var. officinalis |
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| Institution: | 1. College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yangzitang Road, Yongzhou, 425100, China;2. School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi, 832003, China;1. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People''s Republic of China;2. University of Chinese Academy of Sciences, Beijing, 100039, People''s Republic of China;1. Department of Chemistry, University of Douala, Faculty of Science, P.O. Box: 24157 Douala, Cameroon;2. Department of Applied Chemistry, National Advanced School of Agro-Industrial Science, University of Ngaoundere, P.O. Box: 454 Ngaoundere, Cameroon;3. Department of Chemistry, University of Ngaoundere, Faculty of Science, P.O. Box: 454 Ngaoundere, Cameroon;4. Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany |
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| Abstract: | Fifteen methyl 2-naphthoate derivatives (1–15), including 11 previously undescribed ones (1–10 and 13), have been isolated from the roots of a well-known Chinese herb, Morinda officinalis var. officinalis. The structures of these isolates were determined on the basis of detailed spectroscopic analyses, and 12 of them were identified as six pairs of enantiomers (1–12). While the relative configurations of 1 and 5 were confirmed by X-ray crystallographic analysis and calculated 13C NMR data, respectively, the absolute configurations of 1–12 were established via interpretation of experimental and computed ECD data. Compounds 1–4 possessed a novel heterocylic bridge ring system incorporating a 2,6-dioxabicyclo3.2.1]oct-3-ene motif. Our biological evaluations revealed that (−)-mornaphthoate E (9) showed significant cytotoxicity against a panel of human cancer cell lines (MDA-MB-231, MCF-7 and A549, IC50 1–10 μM), while (−)-mornaphthoate A (2) displayed mild inhibition against butyrylcholinesterase (IC50 37.98 ± 1.98 μM). |
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| Keywords: | Rubiaceae Natural enantiomer Methyl 2-naphthoate Cytotoxicity ECD calculation |
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