A new depside and two new diphenyl ether compounds from the lichen Ramalina farinacea (L.) Ach |
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| Institution: | 1. Department of Organic Chemistry, University of Science, National University—Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, 748355 Ho Chi Minh City, Vietnam;2. Department of Chemical–Food Technology, University of Technical Education—Ho Chi Minh City, 1 Vo Van Ngan Str., Thu Duc Dist., 720214 Ho Chi Minh City, Vietnam;3. Department of Chemistry, Ho Chi Minh City University of Pedagogy, 280 An Duong Vuong Street, District 5, 748342 Ho Chi Minh City, Vietnam;4. Department of Chemistry, College of Natural Sciences, Can Tho University, Can Tho, Vietnam;1. Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, 25240 Erzurum, Turkey;2. Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, 06100 Ankara, Turkey;3. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;1. School of Life Science, Beijing Institute of Technology, Beijing 100081, PR China;2. Beijing BIT&GY Pharmaceutical R&D Co. Ltd., Beijing 100081, PR China;1. Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China;2. State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Macau 999078, China;1. ICMR-UMR CNRS 7312, Groupe Isolement et Structure, Campus Sciences, Bât. 18, BP 1039, 51687 Reims Cedex 2, France;2. Laboratoire de Chimie Organique Biologique, 01 BPV 34 Abidjan 01, Université Félix-Houphouët Boigny d’Abidjan-Cocody, Cote d’Ivoire;3. ICMR-UMR CNRS 7312, Service Commun d’Analyses, Campus Sciences, Bât. 18, BP 1039, 51687 Reims Cedex 2, France |
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| Abstract: | The chemical investigation of the Vietnamese lichen Ramalina farinacea (L.) Ach. led to the isolation and the structure elucidation of eight compounds (1–8), including one new depside, formulated as methyl homosekikate (1) and two new diphenyl ethers, 3-(2-carboxy-5-methoxy-3-propylphenoxy)-2-hydroxy-4-methoxy-6-propylbenzoic acid, namely ramalinic acid A (2), and 3-(2-carboxy-5-methoxy-3-propylphenoxy)-2-hydroxy-4-methoxy-6-pentylbenzoic acid, namely ramalinic acid B (3). Their chemical structures were unambiguously determined by analysis of 1D and 2D NMR and high resolution ESI mass spectroscopic data, as well as by comparison with literature data. We also proposed a possible biosynthetic route for the formation of the two new diphenyl ethers (2) and (3) via an enzymatically induced intramolecular Smiles rearrangement of the depsides sekikaic acid and homosekikaic acid, respectively. |
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| Keywords: | Lichen Diphenyl ether Biosynthetic considerations |
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