Pyrroloquinoline derivatives from a Tongan specimen of the marine sponge Strongylodesma tongaensis |
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| Institution: | 1. School of Chemical and Physical Sciences, and Centre for Biodiscovery, Victoria University of Wellington, New Zealand;2. School of Biological and Chemical Sciences, Faculty of Science, Technology and Environment, University of the South Pacific, Suva, Fiji;3. School of Biological Sciences, and Centre for Biodiscovery, Victoria University of Wellington, New Zealand;4. Department of Chemistry, University of Education, Attock Campus, Pakistan;5. Department of Chemistry, University of Management and Technology, Lahore, Pakistan;6. Department of Aquatic Zoology, Western Australian Museum, Australia;7. Ferrier Research Institute, and Centre for Biodiscovery, Victoria University of Wellington, New Zealand;8. Maurice Wilkins Centre for Molecular Biodiscovery, New Zealand;1. Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan;2. Department of Chemistry and Life Science, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan;1. National Museum of Marine Biology and Aquarium, Pingtung, 94450, Taiwan;2. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, 80424, Taiwan;3. Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, 33303, Taiwan;4. Instrumentation Center, National Taiwan University, Taipei, 10617, Taiwan;5. Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, 40402, Taiwan;6. Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung, 40447, Taiwan;7. Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung, 94450, Taiwan;8. Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, 80708, Taiwan;1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;2. Open Studio for Druggability Research of Marine Natural Products, Qingdao National Laboratory for Marine Science and Technology, 1 Wenhai Road, Aoshanwei, Jimo, Qingdao 266237, China;3. University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China;4. Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom;1. Laboratory of Natural Products, Chulabhorn Research Institute, Bangkok 10210, Thailand;2. Program of Chemical Biology, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Bangkok 10210, Thailand;3. Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand;4. The Center of Excellence on Environmental Health and Toxicology (EHT), Commission on Higher Education (CHE), Ministry of Education, Bangkok 10400, Thailand;1. Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China;2. Laboratory of Marine Drugs and Biological Products, National Laboratory of Marine Science and Technology, Qingdao 266235, China;3. National Museum of Natural History, PO Box 9517, 2300 RA Leiden, the Netherlands;4. College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, China;1. Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan;2. National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan;3. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan;4. Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan;5. Department of Pediatrics, E-DA Hospital, School of Medicine, College of Medicine, I-SHOU University, Kaohsiung 840, Taiwan;6. Center for Environmental Toxin and Emerging-Contaminant Research, Cheng Shiu University, Kaohsiung 833, Taiwan;7. Super Micro Mass Research and Technology Center, Cheng Shiu University, Kaoshiung 833, Taiwan;8. Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan;9. Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan;10. Department of Anaesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan;11. Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan;12. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan |
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| Abstract: | Pyrroloquinoline alkaloids are well known bioactive metabolites commonly found from latrunculiid sponges. Two new pyrroloquinoline alkaloids, 6-bromodamirone B (1) and makaluvamine W (2), were isolated from the Tongan sponge Strongylodesma tongaensis. Makaluvamine W (2) contains an oxazole moiety, which is rare in this large group of natural products, and is the first example of a pyrroloquinoline with nitrogen substitution at C-8. Both 1 and 2 lacked activity against a human promyelocytic leukemia cell line (HL-60), supporting the premise that an intact iminoquinone moiety plays a key role in the cytotoxicity of this compound class. The chemotaxonomic impact of these makaluvamine-type compounds is also discussed. |
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| Keywords: | Chemotaxonomy DP4 NMR Oxazole Pyrroloquinoline Sponge |
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