The new pentacyclic guanidine alkaloids, monanchoxymycalin A (1) and monanchoxymycalin B (2) were isolated from the Far-Eastern marine sponge Monanchora pulchra. Their structures were assigned on the basis of detailed analysis of 1D- and 2D-NMR spectroscopic and mass spectrometric data. Compounds 1 and 2 exhibited potent cytotoxic activities against cervical epithelioid carcinoma HeLa cells and breast adenocarcinoma MDA-MB231 cells.
BerlinckR.G.S., RommingerS. (2016) The chemistry and biology of guanidine natural products. Natural Product Reports, 33, 456–490, and other reviews in this series.
2.
KashmanY., HirshS., McConnellO.J., OhtaniI., KusumiT., KakisawaH. (1989) Ptilomycalin A: a novel polycyclic guanidine alkaloid of marine origin. Journal of the American Chemical Society, 111, 8925–8926.
3.
OhtaniI., KusumiT., KakisawaH., KashmanY., HirshS. (1992) Structure and chemical properties of ptilomycalin A. Journal of the American Chemical Society, 114, 8472–8479.
4.
OhtaniI., KusumiT., KakisawaH. (1992) An insight into the conformation of ptilomycalin A. The NMR properties of trifluoroacetylated spermidine analogues. Tetrahedron Letters, 33, 2525–2528.
5.
Jares-ErijmanE.A., SakaiR., RinehartK.L. (1991) Crambescidins: new antiviral and cytotoxic compounds from the sponge Crambe crambe. Journal of Organic Chemistry, 56, 5712–5715.
6.
BerlinckR.G.S., BraekmanJ.C., DalozeD., BrunoI., RiccoR., FerriS., SpampinatoS., SperoniE. (1993) Polycyclic guanidine alkaloids from the marine sponge Crambe crambe and Ca++ channel blocker activity of crambescidin 816. Journal of Natural Products, 56, 1007–1015.
7.
Jares-ErijmanE.A., IngrumA.L., CarneyJ.R., RinehartK.L., SakaiR. (1993) Polycyclic guanidine-containing compounds from the Mediterranean sponge Crambe crambe: the structure of 13,14,15-isocrambescidin 800 and the absolute stereochemistry of the pentacyclic guanidine moieties of the crambescidins. Journal of Organic Chemistry, 58, 4805–4808.
8.
TavaresR., DalozeD., BraekmanJ.C., HajduE., MuricyG., Van SoestR.W.M. (1994) Isolation of crambescidin 800 from Monanchora arbuscula (Porifera). Biochemical Systematics and Ecology, 22, 645–646.
9.
VenkateswarluY., ReddyM.V.R., RameshP., RaoJ.V. (1999) Neofolitispates, pentacyclic guanidine alkaloids from the sponge Neofolitispa dianchora. Indian Journal of Chemistry, 38B, 254–256.
10.
ChangL.C., WhittakerN.F., BewleyC.A. (2003) Crambescidin 826 and dehydrocrambine A: new polycyclic guanidine alkaloids from the marine sponge Monanchora sp that inhibit HIV-1 fusion. Journal of Natural Products, 66, 1490–1494.
11.
BraekmanJ.C., DalozeD., TavaresR., HajduE., Van SoestR.W.M. (2000) Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora. Journal of Natural Products, 63, 193–196.
12.
BensemhounJ., BombardaI., AkninM., VaceletJ., GaydouE.M. (2007) Ptilomycalin D, a polycyclic guanidine alkaloid from the marine sponge Monanchora dianchora. Journal of Natural Products, 70, 2033–2035.
13.
GuziiA.G., MakarievaT.N., DenisenkoV.A., DmitrenokP.S., KuzmichA.S., DyshlovoyS.A., KrasokhinV.B., StonikV.A. (2010) Monanchocidin: a new apoptosis-inducing polycyclic guanidine alkaloid from the marine sponge Monanchora pulchra. Organic Letters, 12, 4292–4295.
14.
MakarievaT.N., TabakmaherK.M., GuziiA.G., DenisenkoV.A., DmitrenokP.S., ShubinaL.K., KuzmichA.S., LeeH.S., StonikV.A. (2011) Monanchocidins B-E: polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra. Journal of Natural Products, 74, 1952–1958.
15.
MakarievaT.N., TabakmaherK.M., GuziiA.G., DenisenkoV.A., DmitrenokP.S., KuzmichA.S., LeeH.S., StonikV.A. (2012) Monanchomycalins A and B, unusual guanidine alkaloids from the sponge Monanchora pulchra. Tetrahedron Letters, 53, 4228–4231.
16.
TabakmakherK.M., GuziiA.G., DenisenkoV.A., DmitrenokP.S., LeeH.S., MakarievaT.N. (2013) Monanchomycalin C, a new pentacyclic guanidine alkaloid from the Far-Eastern marine sponge Monanchora pulchra. Natural Product Communications, 8, 1399–1402.
17.
TabakmakherK.M., MakarievaT.N., DenisenkoV.A., GuziiA.G., DmitrenokP.S., KuzmichA.S., StonikV.A. (2015) Normonanchocidins A, B and D, new pentacyclic guanidine alkaloids from the Far-Eastern marine sponge Monanchora pulchra. Natural Product Communications, 10, 913–916.
18.
BaltropJ.A., OwenT.C., CoryA.H., CoryJ.G. (1991) 5-(3-Carboxymethoxyphenyl)-2-(4,5-dimethylthiazolyl)-3-(4-sulfophenyl)tetrazolium, inner salt (MTS) and related analogs of 3-(4,5-dimethylthiazolyl)2,5-diphenyltetrazolium bromide (MTT) reducting to purple water-soluble formazans as cell-viability indicators. Bioorganic & Medicinal Chemistry Letters, 1, 611–614.