Dysidinoid A, an Unusual Meroterpenoid with Anti-MRSA Activity from the South China Sea Sponge Dysidea sp.
Abstract
:1. Introduction
2. Results and Discussion
Position | δC | δH (J in Hz) | HMBC (H→C) | NOESY |
---|---|---|---|---|
1α | 19.0, CH2 | 1.83, m | C-2, 3, 5, 9, 10 | H-1β, 2β, 10 |
1β | 1.53, m | C-2, 5, 10 | H3-12, 14, H-1α, 2β | |
2α | 26.3, CH2 | 1.93, m | H-1α, 1β, 10 | |
2β | 2.07, m | C-3, 4, 10 | H-1α, 1β, 2α | |
3 | 120.5, CH | 5.16, br s | C-5, 11 | H3-11, H-2α, 2β |
4 | 143.9, C | |||
5 | 38.3, C | |||
6α | 36.2, CH2 | 1.08, m | C-8 | H-6β, 7a, 8, 10 |
6β | 1.68, dt (12.8, 3.4) | C-7, 8, 10, 12 | H3-11, 12, H-6α, 7b | |
7a | 27.4, CH2 | 1.41, m | C-5, 6, 9, 13 | H-6, 8 |
7b | 1.40, dd (6.9, 3.5) | H-6, 8, H3-12, 13, 14 | ||
8 | 37.4, CH | 1.28, m | C-7, 9, 13 | H-7b, 10, H3-13 |
9 | 42.4, C | |||
10 | 47.0, CH | 1.12, dd (12.4, 1.6) | C-2, 4, 5, 9, 12, 14, 15 | H-1α, 2α, 8, 15α, 15β |
11 | 17.7, CH3 | 1.55, br s | C-3, 4, 5 | H3-12, H-3 |
12 | 19.8, CH3 | 1.00, s | C-4, 5, 6, 10 | H3-11, 14, H-6β, 7β |
13 | 16.3, CH3 | 0.95, d (6.7) | C-7, 8, 9 | H3-14, H-7β, 8 |
14 | 18.0, CH3 | 0.88, s | C-8, 9, 10, 15 | H3-12, 13, H-1β, 7β |
15α | 32.5, CH2 | 2.61, d (14.1) | C-8, 9, 10, 14, 16, 17, 18 | H3-14, H-1α, 10 |
15β | 2.43, dd (14.1, 1.2) | C-8, 9, 10, 14, 16, 17, 18 | H3-13 | |
16 | 147.9, C | |||
17 | 171.7, C | |||
18 | 130.4, CH | 6.26, d (1.0) | C-15, 16, 19 | H3-13, H-10, 15α, 15β |
19 | 170.4, C | |||
20-NH | 7.33, br s |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Animal Material
3.3. Extraction, Isolation and Characterization
3.4. X-ray Crystallographic Analysis of Dysidinoid A (1)
3.5. Antimicrobial Assays
4. Conclusions
Supplementary Materials
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
- Figueroa, M.; Jarmusch, A.K.; Raja, H.A.; El-Elimat, T.; Kavanaugh, J.S.; Horswill, A.R.; Cooks, R.G.; Cech, N.B.; Oberlies, N.H. Polyhydroxyanthraquinones as quorum sensing inhibitors from the guttates of penicillium restrictum and their analysis by desorption electrospray ionization mass spectrometry. J. Nat. Prod. 2014, 77, 1351–1358. [Google Scholar]
- Li, T.; Song, Y.; Zhu, Y.; Du, X.; Li, M. Current status of Staphylococcus aureus infection in a central teaching hospital in Shanghai, China. BMC Microbiol. 2003, 13. [Google Scholar] [CrossRef]
- Payne, D.J. Desperately seeking new antibiotics. Science 2008, 321, 1644–1645. [Google Scholar]
- Plaza, A.; Keffer, J.L.; Bifulco, G.; Lloyd, J.R.; Bewley, C.A. Chrysophaentins A–H, antibacterial bisdiarylbutene macrocycles that inhibit the bacterial cell division protein FtsZ. J. Am. Chem. Soc. 2010, 132, 9069–9077. [Google Scholar]
- Li, M.; Du, X.; Villaruz, A.; Diep, B.; Wang, D.; Song, Y.; Tian, Y.; Hu, J.; Yu, F.; Lu, Y.; et al. MRSA epidemic linked to a quickly spreading colonization and virulence determinant. Nat. Med. 2012, 18, 816–819. [Google Scholar]
- Jiao, W.H.; Xu, T.T.; Yu, H.B.; Chen, G.D.; Huang, X.J.; Yang, F.; Li, Y.S.; Han, B.N.; Liu, X.Y.; Lin, H.W. Dysideanones A–C, unusual sesquiterpene quinones from the South China Sea sponge Dysidea avara. J. Nat. Prod. 2014, 77, 346–350. [Google Scholar]
- Jiao, W.H.; Xu, T.T.; Yu, H.B.; Mu, F.R.; Li, J.; Li, Y.S.; Yang, F.; Han, B.N.; Lin, H.W. Dysidaminones A–M, cytotoxic and NF-κB inhibitory sesquiterpene aminoquinones from the South China Sea sponge Dysidea fragilis. RSC Adv. 2014, 4, 9236–9246. [Google Scholar]
- Marcos, I.S.; Conde, A.; Moro, R.F.; Basabe, P.; Diez, D.; Urones, J.G. Quinone/hydroquinone sesquiterpenes. Mini-Rev. Org. Chem. 2010, 7, 230–254. [Google Scholar]
- Ueda, K.; Kadekaru, T.; Siwu, E.R.; Kita, M.; Uemura, D. Haterumadysins A–D, sesquiterpenes from the Okinawan Marine sponge Dysidea c hlorea. J. Nat. Prod. 2006, 69, 1077–1079. [Google Scholar]
- Lu, Q.; Faulkner, D.J. Three dolabellanes and a macrolide from the sponge Dysidea sp. from Palau. J. Nat. Prod. 1998, 61, 1096–1100. [Google Scholar]
- De Almeida Leone, P.; Redburn, J.; Hooper, J.N. A.; Quinn, R.J. Polyoxygenated Dysidea sterols that inhibit the binding of [I125] IL-8 to the human recombinant IL-8 receptor type A. J. Nat. Prod. 2000, 63, 694–697. [Google Scholar]
- Bai, R.; Paull, K.; Herald, C.; Malspeis, L.; Pettit, G.; Hamel, E. Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data. J. Biol. Chem. 1991, 266, 15882–15889. [Google Scholar]
- Fu, X.; Ferreira, M.L.G.; Schmitz, F.J.; Kelly-Borges, M. New diketopiperazines from the sponge Dysidea chlorea. J. Nat. Prod. 1998, 61, 1226–1231. [Google Scholar]
- Kazlauskas, R.; Murphy, P.; Warren, R.; Wells, R.; Blount, J. New quinones from a dictyoceratid sponge. Aust. J. Chem. 1978, 31, 2685–2697. [Google Scholar]
- Ciavatta, M.L.; Lopez Gresa, M.P.; Gavagnin, M.; Romero, V.; Melck, D.; Manzo, E.; Guo, Y.W.; van Soest, R.; Cimino, G. Studies on puupehenone-metabolites of a Dysidea sp.: Structure and biological activity. Tetrahedron 2007, 63, 1380–1384. [Google Scholar]
- Urban, S.; Capon, R.J. 5-epi-Isospongiaquinone, a new sesquiterpene/quinone antibiotic from an Australian Marine sponge, Spongia hispida. J. Nat. Prod. 1992, 55, 1638–1642. [Google Scholar]
- Pérez-García, E.; Zubía, E.; Ortega, M.J.; Carballo, J.L. Merosesquiterpenes from two sponges of the genus Dysidea. J. Nat. Prod. 2005, 68, 653–658. [Google Scholar]
- Jiao, W.H.; Huang, X.J.; Yang, J.S.; Yang, F.; Piao, S.J.; Gao, H.; Li, J.; Ye, W.C.; Yao, X.S.; Chen, W.S.; et al. Dysidavarones A–D, new sesquiterpene quinones from the marine sponge Dysidea avara. Org. Lett. 2012, 14, 202–205. [Google Scholar]
- McNamara, C.E.; Larsen, L.; Perry, N.B.; Harper, J.L.; Berridge, M.V.; Chia, E.W.; Kelly, M.; Webb, V.L. Anti-inflammatory sesquiterpene-quinones from the New Zealand sponge Dysidea cf. cristagalli. J. Nat. Prod. 2005, 68, 1431–1433. [Google Scholar]
- Utkina, N.K.; Denisenko, V.A.; Krasokhin, V.B. Sesquiterpenoid aminoquinones from the marine sponge Dysidea sp. J. Nat. Prod. 2010, 73, 788–791. [Google Scholar]
- Sample Availability: Sample of the compound 1is available from the authors.
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Jiao, W.-H.; Li, J.; Liu, Q.; Xu, T.-T.; Shi, G.-H.; Yu, H.-B.; Yang, F.; Han, B.-N.; Li, M.; Lin, H.-W. Dysidinoid A, an Unusual Meroterpenoid with Anti-MRSA Activity from the South China Sea Sponge Dysidea sp. Molecules 2014, 19, 18025-18032. https://doi.org/10.3390/molecules191118025
Jiao W-H, Li J, Liu Q, Xu T-T, Shi G-H, Yu H-B, Yang F, Han B-N, Li M, Lin H-W. Dysidinoid A, an Unusual Meroterpenoid with Anti-MRSA Activity from the South China Sea Sponge Dysidea sp. Molecules. 2014; 19(11):18025-18032. https://doi.org/10.3390/molecules191118025
Chicago/Turabian StyleJiao, Wei-Hua, Jing Li, Qian Liu, Ting-Ting Xu, Guo-Hua Shi, Hao-Bing Yu, Fan Yang, Bing-Nan Han, Min Li, and Hou-Wen Lin. 2014. "Dysidinoid A, an Unusual Meroterpenoid with Anti-MRSA Activity from the South China Sea Sponge Dysidea sp." Molecules 19, no. 11: 18025-18032. https://doi.org/10.3390/molecules191118025