Isolation of Ciliatamide D from a Marine Sponge Stelletta sp. and a Reinvestigation of the Configuration of Ciliatamide A
- Yasufumi Imae ,
- Kentaro Takada ,
- Shigeru Okada ,
- Yuji Ise ,
- Hiroshi Yoshimura ,
- Yasuhiro Morii , and
- Shigeki Matsunaga
View Author Information
† Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan
‡ Misaki Marine Biological Station, The University of Tokyo, Miura, Kanagawa 238-0225, Japan
§ Faculty of Fisheries, Nagasaki University, Bunkyo-machi, Nagasaki 852-8521, Japan
*Tel: +81-3-5841-5297. Fax: +81-3-5841-8166. E-mail: [email protected]
Abstract
A new lipopeptide, ciliatamide D (1), was isolated from a marine sponge Stelletta sp., collected at Oshimashinsone, together with the known compound ciliatamide A (2). Ciliatamide D (1) is a congener of 2, in which N-Me-Phe is replaced by N-Me-Met(O). Marfey’s analysis of the acid hydrolysate of 1 demonstrated that the two constituent amino acids were both in the l-form. This result prompted us to carefully investigate the configuration of 2, resulting in the assignment of the l-form for both residues.
Cited By
This article is cited by 9 publications.
- Allison K. Stewart, Rudravajhala Ravindra, Ryan M. Van Wagoner, and Jeffrey L. C. Wright . Metabolomics-Guided Discovery of Microginin Peptides from Cultures of the Cyanobacterium Microcystis aeruginosa. Journal of Natural Products 2018, 81 (2) , 349-355. https://doi.org/10.1021/acs.jnatprod.7b00829
- Kentaro Takada, Raku Irie, Rei Suo, and Shigeki Matsunaga . Resolution of the Confusion in the Assignments of Configuration for the Ciliatamides, Acylated Dipeptides from Marine Sponges. Journal of Natural Products 2017, 80 (10) , 2845-2849. https://doi.org/10.1021/acs.jnatprod.7b00684
- Noémie Emmanuel, Carlos Mendoza, Marc Winter, Clemens R. Horn, Alessandra Vizza, Laurent Dreesen, Benoît Heinrichs, and Jean-Christophe M. Monbaliu . Scalable Photocatalytic Oxidation of Methionine under Continuous-Flow Conditions. Organic Process Research & Development 2017, 21 (9) , 1435-1438. https://doi.org/10.1021/acs.oprd.7b00212
- Chang-Kwon Kim, Inn-Hye Song, Ha Young Park, Yeon-Ju Lee, Hyi-Seung Lee, Chung J. Sim, Dong-Chan Oh, Ki-Bong Oh, and Jongheon Shin . Suvanine Sesterterpenes and Deacyl Irciniasulfonic Acids from a Tropical Coscinoderma sp. Sponge. Journal of Natural Products 2014, 77 (6) , 1396-1403. https://doi.org/10.1021/np500156n
- Yuqi Du, Chen Wang, Guodong Cui, Yiwen Chu, Qian Jia, Yi Wang, Weiming Zhu. Cytotoxic and Optically Active Pyrisulfoxins From the Endophytic Streptomyces albolongus EA12432. Frontiers in Chemistry 2020, 8 https://doi.org/10.3389/fchem.2020.00248
- Qihao Wu, Bastien Nay, Min Yang, Yeke Ni, Hong Wang, Ligong Yao, Xuwen Li. Marine sponges of the genus Stelletta as promising drug sources: chemical and biological aspects. Acta Pharmaceutica Sinica B 2019, 9 (2) , 237-257. https://doi.org/10.1016/j.apsb.2018.10.003
- Javier Mazuela, Thomas Antonsson, Laurent Knerr, Stephen P. Marsden, Rachel H. Munday, Magnus J. Johansson. Iridium‐Catalyzed Asymmetric Hydrogenation of N ‐Alkyl α‐Aryl Furan‐Containing Imines: an Efficient Route to Unnatural N ‐Alkyl Arylalanines and Related Derivatives.. Advanced Synthesis & Catalysis 2019, 361 (3) , 578-584. https://doi.org/10.1002/adsc.201801143
- Krishnakumari Avula, Debendra K. Mohapatra. Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation. Tetrahedron Letters 2016, 57 (15) , 1715-1717. https://doi.org/10.1016/j.tetlet.2016.03.017
- John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2015, 32 (2) , 116-211. https://doi.org/10.1039/C4NP00144C