A new tetramic acid glycoside, aurantoside K, was isolated from a marine sponge belonging to the genus Melophlus. The structure of the compound was elucidated on the basis of spectroscopic analysis ( 1H NMR, 1H– 1H COSY, HSQC, and HMBC, as well as high-resolution ESILCMS). Aurantoside K did not show any significant activity in antimalarial, antibacterial, or HCT-116 cytotoxicity assays, but exhibited a wide spectrum of antifungal activity against wild type Candida albicans, amphotericin-resistant C. albicans, Cryptococcus neoformans, Aspergillus niger, Penicillium sp ., Rhizopus sporangia and Sordaria sp .
References
[1]
Newman, D.J.; Cragg, G.M.; Snader, K.M. Natural products as sources of new drugs over the period 1981–2002. J. Nat. Prod. 2003, 66, 1022–1037, doi:10.1021/np030096l. 12880330
[2]
Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007, 70, 461–477, doi:10.1021/np068054v. 17309302
Simmons, T.L.; Coates, R.C.; Clark, B.R.; Engene, N.; Gonzalez, D.; Esquenazi, E.; Dorrestein, P.C.; Gerwick, W.H. Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages. Proc. Natl. Acad. Sci. USA 2008, 105, 4587–4594, doi:10.1073/pnas.0709851105. 18250337
[8]
Aoki, S.; Higuchi, K.; Ye, Y.; Satari, R.; Kobayashi, M. Melophlins A and B, novel tetramic acids reversing the phenotype of ras-transformed cells, from the marine sponge Melophlus sarassinorum. Tetrahedron 2000, 56, 1833–1836, doi:10.1016/S0040-4020(00)00092-2.
[9]
Wang, C.-Y.; Wang, B.-G.; Wiryowidagdo, S.; Wray, V.; van Soest, R.W.M.; Steube, K.G.; Guan, H.-S.; Proksch, P.; Ebel, R. Melophlins C–O, thirteen novel tetramic acids from the marine sponge Melophlus sarassinorum. J. Nat. Prod. 2003, 66, 51–56, doi:10.1021/np0202778. 12542345
[10]
Xu, J.; Hasegawa, M.; Harada, K.-I.; Kobayashi, H.; Nagai, H.; Namikoshi, M. Melophlins P, Q, R, and S: Four new tetramic acid derivatives, from two palauan marine sponges of the genus Melophlus. Chem. Pharm. Bull. 2006, 54, 852–854, doi:10.1248/cpb.54.852. 16755057
[11]
Lee, S.-H.; Seo, Y.; Cho, K.W.; Rho, J.-R.; Shin, J.; Paul, V. New triterpenoid saponins from the sponge Melophlus isis. J. Nat. Prod. 2000, 63, 915–919, doi:10.1021/np990589j. 10924165
[12]
Dai, H.-F.; Edrada, R.A.; Ebel, R.; Nimtz, M.; Wray, V.; Proksch, P. Norlanostane triterpenoidal saponins from the marine sponge Melophlus sarassinorum. J. Nat. Prod. 2005, 68, 1231–1237, doi:10.1021/np050152d. 16124767
[13]
Prasad, P.; Aalbersberg, W.; Feussner, K.-D.; Wagoner, R.M.V. Papuamides E and F, cytotoxic depsipeptides from the marine sponge Melophlus sp. Tetrahedron 2011, 67, 8529–8531. 22003260
[14]
Matsunaga, S.; Fusetani, N.; Kato, Y.J. Aurantosides A and B: Cytotoxic tetramic acid glycosides from the marine sponge Theonella sp. J. Am. Chem. Soc. 1991, 113, 9690–9692, doi:10.1021/ja00025a054.
[15]
Wolf, D.; Schmitz, F.J.; Qui, F.; Kelly-Borges, M. Aurantoside C, a new tetramic acid glycoside from the sponge Homophymia conferta. J. Nat. Prod. 1999, 62, 170–172, doi:10.1021/np980283x. 9917312
[16]
Sata, N.U.; Matsunaga, S.; Fusetani, N.; van Soest, R.W.M. Aurantosides D, E, and F: New antifungal tetramic acid glycosides from the marine sponge Siliquariaspongia japonica. J. Nat. Prod. 1999, 62, 969–971, doi:10.1021/np9900021. 10425118
[17]
Ratnayake, A.S.; Davis, R.A.; Harper, M.K.; Veltri, C.A.; Andjelic, C.D.; Barrows, L.R.; Ireland, C.M. Aurantosides G, H, and I: Three new tetramic acid Glycosides from a Papua New Guinea Theonella swinhoei. J. Nat. Prod. 2005, 68, 104–107, doi:10.1021/np049721s. 15679329
[18]
Angawi, R.F.; Bavestrello, G.; Calcinai, B.; Dien, H.A.; Donnarumma, G.; Tufano, M.A.; Paoletti, I.; Grimaldi, E.; Chianese, G.; Fattorusso, E.; et al. Aurantoside J: A new tetramic acid glycoside from Theonella swinhoei. Insights into the antifungal potential of aurantosides. Mar. Drugs 2011, 9, 2809–2817, doi:10.3390/md9122809.
[19]
Blunt, J.W.; Munro, M.H.G. Marinlit vpc 15.5; University of Canterbury: Christchurch, New Zealand, 2011.
[20]
Schmidt, E.W.; Harper, M.K.; Faulkner, D.J. Mozamides A and B, cyclic peptides from a theonellid sponge from mozambique. J. Nat. Prod. 1997, 60, 779–782, doi:10.1021/np970195x.
[21]
Lee, F.Y.F.; Borzilleri, R.; Fairchild, C.R.; Kim, S.H.; Long, B.H.; Raventos-Suarez, C.; Vite, G.D.; Rose, W.C.; Kramer, R.A. A novel epothilone analog with a mode of action similar to paclitaxel but possessing superior antitumor efficacy. Clin. Cancer Res. 2001, 7, 1429–1437. 11350914
[22]
Smilkstein, M.; Sriwilaijaroen, N.; Kelly, J.X.; Wilairat, P.; Riscoe, M. Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening. Antimicrob. Agents Chemother. 2004, 48, 1803–1806, doi:10.1128/AAC.48.5.1803-1806.2004. 15105138
[23]
Bennett, T.N.; Paguio, M.; Gligorijevic, B.; Seudieu, C.; Kosar, A.D.; Davidson, E.; Roepe, P.D. Novel, rapid, and inexpensive cell-based quantification of antimalarial drug efficacy. Antimicrob. Agents Chemother. 2004, 48, 1807–1810, doi:10.1128/AAC.48.5.1807-1810.2004. 15105139
[24]
Trager, W.; Jensen, J.B. Human malaria parasites in continuous culture. Science 1976, 193, 673–675, doi:10.1126/science.781840. 781840
[25]
Kubanek, J.; Prusak, A.C.; Snell, T.W.; Giese, R.A.; Hardcastle, K.I.; Fairchild, C.R.; Aalbersberg, W.; Raventos-Suarez, C.; Hay, M.E. Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus. Org. Lett. 2005, 7, 5261–5264, doi:10.1021/ol052121f. 16268553