A new pentacyclic guanidine alkaloid, monanchomycalin C (1), along with the earlier known ptilomycalin A (2), were isolated from the Far-Eastern marine sponge Monanchora pulchra. The structure of 1 was elucidated using 1D and 2D NMR spectroscopic and mass spectrometric data. Compounds 1 and 2 exhibited cytotoxic activities against human breast cancer MDA-MB-231 cells with IC50 values of 8.2 μM and 4.3 μM, respectively.
BerlinckR.G.S., BurtolosoA.C.B., KossugaM.H. (2008) The chemistry and biology of organic guanidine derivatives. Natural Product Reports, 25, 919–954.
4.
BerlinckR.G.S., BurtolosoA.C.B., Trindade-SilvaA.E., RommingerS., MoraisR.P., BandeiraK., MizunoC.M. (2010) The chemistry and biology of organic guanidine derivatives. Natural Product Reports, 27, 1871–1907.
5.
BerlinckR.G.S., Trindade-SilvaA.E., SantosM.F.C. (2012) The chemistry and biology of organic guanidine derivatives. Natural Product Reports, 29, 1382–1406.
6.
AbbasS., KellyM., BowlingJ., SimsJ., WatersA., HamannM. (2011) Advancement into the Arctic region for bioactive sponge secondary metabolites. Marine Drugs, 9, 2423–2437.
7.
MeragelmanK.M., McKeeT.C., McMahonJ.B. (2004) Monanchorin, a bicyclic alkaloid from the sponge Monanchora ungiculata. Journal of Natural Products, 67, 1165–1167.
8.
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.
9.
TavaresR., DalozeD., BraekmanJ.C., HajduE., Van SoestR.W.M. (1995) 8b-hydroxyptilocaulin, a new guanidine alkaloid from the sponge Monanchora arbuscula. Journal of Natural Products, 58, 1139–1142.
10.
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.
11.
KossugaM.H., de LiraS.P., NascimentoA.M., GambardellaM.T.P., BerlinckR.G.S., TorresY.R., NascimentoG.G.E., PimentaE.E., SilvaM., ThiemannO.H., OlivaG., TemponeA.G., MelhemM.S.C., de SouzaA.O., GalettiF.C.S., SilvaC.L., CavalcantiB., PessoaC.O., MoraesM.O., HajduE., PeixinhoS., RochaR.M. (2007) Isolation and biological activities of secondary metabolites from the sponges Monanchora aff. arbuscula, Aplysina sp. Petromica ciocalyptoides and Topsentia ophiraphidites, from the ascidian Didemnum ligulum and from the octocoral Carijoa riisei.Quimica Nova, 30, 1194–1202.
12.
LavilleR., ThomasO.P., BerrueF., MarquezD., VaceletJ., AmadeP. (2009) Bioactive guanidine alkaloids from two Caribbean marine sponges. Journal of Natural Products, 72, 1589–1594.
13.
FerreiraE.G., WilkeD.V., JimenezP.C., de OliveiraJ.R., PessoaO.D.L., SilveiraE.R., VianaF.A., PessoaC., de MoraesM.O., HajduE., Costa-LotufoL.V. (2011) Guanidine alkaloids from Monanchora arbuscula: chemistry and antitumor potential. Chemistry & Biodiversity, 8, 1433–1445.
14.
TakishimaS., IshiyamaA., IwatsukiM., OtoguroK., YamadaH., OmuraS., KobayashiH., van SoestR.W.M., MatsunagaS. (2009) Merobatzelladines A and B, anti-infective tricyclic guanidines from a marine sponge Monanchora sp. Organic Letters, 11, 2655–2658.
15.
HuaH.M., PengJ.N., FronczekF.R., KellyM., HamannM.T. (2004) Crystallographic and NMR studies of antiinfective tricyclic guanidine alkaloids from the sponge Monanchora unguifera. Bioorganic & Medicinal Chemistry, 12, 6461–6464.
16.
GallimoreW.A., KellyM., ScheuerP.J. (2005) Alkaloids from the sponge Monanchora unguifera. Journal of Natural Products, 68, 1420–1423.
17.
HuaH.M., PengJ., DunbarD.C., SchinaziR.F., AndrewsAGDC, CuevasC., Garcia-FernandezL.F., KellyM., HamannM.T. (2007) Batzelladine alkaloids from the Caribbean sponge Monanchora unguifera and the significant activities against HIV-1 and AIDS opportunistic infectious pathogens. Tetrahedron, 63, 11179–11188.
18.
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.
19.
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.
20.
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.
21.
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.
22.
SunaH., AokiS., SetiawanA., KobayashiM. (2007) Crambescidin 800, a pentacyclic guanidine alkaloid, protects a mouse hippocampal cell line against glutamate-induced oxidative stress. Journal of Natural Medicines, 61, 288–295.
23.
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.
24.
VenkateswarluY., ReddyM.V.R., RameshP., RaoJ.V. (1999) Neofolitispates, pentacyclic guanidine alkaloids from the sponge Neofolitispa dianchora. Indian Journal of Chemistry, 38B, 254–256.
25.
GuziiA.G., MakarievaT.N., KorolkovaY.V., AndreevY.A., MosharovaI.V., TabakmaherK.M., DenisenkoV.A., DmitrenokP.S., OgurtsovaE.K., AntonovA.S., LeeH.S., GrishinE.V. (2013) Pulchranin A, isolated from the Far-Eastern marine sponge, Monanchora pulchra: the first marine non-peptide inhibitor of TRPV-1 channels. Tetrahedron Letters, 54, 1247–1250.
26.
MakarievaT.N., OgurtsovaE.K., KorolkovaY.V., AndreevY.A., MosharovaI.V., TabakmaherK.M., GuziiA.G., DenisenkoV.A., DmitrenokP.S., LeeH.S., GrishinE.V., StonikV.A. (2013) Pulchranins B and C, new acyclic guanidine alkaloids from the Far-Eastern marine sponge Monanchora pulchra. Natural Product Communications, 8, 1229–1232.
27.
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.
28.
OhtaniI., KusumiT., KakisawaH., KashmanY., HirshS. (1992) Structure and chemical properties of ptilomycalin A. Journal of the American Chemical Society, 114, 8472–8479.
29.
PalagianoE., DemarinoS., MinaleL., RiccioR., ZolloF., IorizziM., CarreJ.B., DebitusC., LucarainL., ProvostJ. (1995) Ptilomicalin A, crambescidin 800 and related new higly cytotoxic guanidine alkaloids from the starfishes Formia monilis and Celerina hefferenani. Tetrahedron, 51, 3675–3682.
30.
MakarievaT.N., DmitrenokP.S., ZakharenkoA.M., DenisenkoV.A., GuziiA.G., LiR., SkepperC.K., MolinskiT.F., StonikV.A. (2007) Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo–sphingolipid and a facile method for determination of the carbonyl position in α,ω–bifunctionalized ketosphingolipidsJournal of Natural Products, 70, 1991–1998.
31.
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.
32.
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.
33.
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.
34.
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.
35.
DyshlovoyS.A., FedorovS.N., KalinovskyA.I., ShubinaL.K., BokemeyerC., StonikV.A., HoneckerF. (2012) Mycalamide A shows cytotoxic properties and prevents EGF-induced neoplastic transformation through inhibition of nuclear factors. Marine Drugs, 10, 1212–1224.
36.
DyshlovoyS.A., NaethI., VenzS., PreukschasM., SievertH., JacobsenC., ShubinaL.K., SalazarM.G., ScharfC., WaltherR., KrepstakiesM., PriyadarshiniP., HauberJ., FedorovS.N., BokemeyerC., StonikV.A., BalabanovS., HoneckerF. (2012) Proteomic profiling of germ cancer cells treated with aaptamine, a marine alkaloid with antiproliferative activity. Journal of Proteome Research, 11, 2316–2330.
