A new β-carboline alkaloid, 3,4-dihydrohyrtiosulawesine (8), and fifteen known alkaloids were isolated from the tropical marine sponge Hyrtios sp. Among these known compounds, β-ketoserotonin (10) has been isolated for the first time from a natural source. The structures of the isolated compounds were determined by spectroscopic analyses and comparison with literature values. Compound 8 displayed potent inhibitory activities against isocitrate lyase (IC50: 92.9 μM) from Candida albicans.
KobayashiJ., MurayamaT., IshibashiM., KosugeS., TakamatsuM., OhizumiY., KobayashiH., OhtaT., NozoeS., SasakiT. (1990) Hyrtiosin-A and Hyrtiosin-B, New indole alkaloids from the Okinawan marine sponge Hyrtios erecta. Tetrahedron, 46, 7699–7702.
3.
LongeonA., CoppB.R., QuevrainE., RoueM., KientzB., CresteilT., PetekS., DebitusC., Bourguet-KondrackiM.L. (2011) Bioactive indole derivatives from the south Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Marine Drugs, 9, 879–888.
4.
SalmounM., DevijverC., DalozeD., BraekmanJ.C., van SoestR.W.M. (2002) 5-Hydroxytryptamine-derived alkaloids from two marine sponges of the genus Hyrtios. Journal of Natural Products, 65, 1173–1176.
5.
SauleauP., MartinM.T., DauM.E., YoussefD.T., Bourguet-KondrackiM.L. (2006) Hyrtiazepine, an azepino-indole-type alkaloid from the Red Sea marine sponge Hyrtios erectus. Journal of Natural Products, 69, 1676–1679.
YoussefD.T. (2005) Hyrtioerectines A-C, cytotoxic alkaloids from the Red Sea sponge Hyrtios erectus. Journal of Natural Products, 68, 1416–1419.
8.
LorenzM.C., FinkG.R. (2001) The glyoxylate cycle is required for fungal virulence. Nature, 412, 83–86.
9.
LeeH.S., LeeT.H., LeeJ.H., ChaeC.S., ChungS.C., ShinD.S., ShinJ., OhK.B. (2007) Inhibition of the pathogenicity of Magnaporthe grisea by bromophenols, isocitrate lyase inhibitors, from the red alga Odonthalia corymbifera. Journal of Agricultural and Food Chemistry, 55, 6923–6928.
HautzelR., AnkeH., SheldrickW.S. (1990) Mycenon, a new metabolite from a Mycena species TA 87202 (basidiomycetes) as an inhibitor of isocitrate lyase. Journal of Antibiotics, 43, 1240–1244.
12.
KoY.H., McFaddenB.A. (1990) Alkylation of isocitrate lyase from Escherichia coli by 3-bromopyruvate. Archives of Biochemistry and Biophysics, 278, 373–380.
13.
KoY.H., VanniP., McFaddenB.A. (1989) The interaction of 3-phosphoglycerate and other substrate analogs with the glyoxylate- and succinate-binding sites of isocitrate lyase. Archives of Biochemistry and Biophysics, 274, 155–160.
14.
McFaddenB.A., PurohitS. (1977) Itaconate, an isocitrate lyase-directed inhibitor in Pseudomonas indigofera. Journal of Bacteriology, 131, 136–144.
15.
ShinD.S., KimS., YangH.C., OhK.B. (2005) Cloning and expression of isocitrate lyase, a key enzyme of the glyoxylate cycle, of Candida albicans for development of antifungal drugs. Journal of Microbiology and Biotechnology, 15, 652–655.
SakaiE., KatoH., RotinsuluH., LosungF., MangindaanR.E., de VoogdN.J., YokosawaH., TsukamotoS. (2014) Variabines A and B: new β-carboline alkaloids from the marine sponge Luffariella variabilis. Journal of Natural Medicines, 68, 215–219.
18.
LaiZ.Q., LiuW.H., IpS.P., LiaoH.J., YiY.Y., QinZ., LaiX.P., SuZ.R., LinZ.X. (2014) Seven alkaloids from Picrasma quassioides and their cytotoxic activities. Chemistry of Natural Compounds, 50, 884–888.
19.
MusshoffF., DaldrupT., BonteW., LeitnerA., LeschO.M. (1996) Formaldehyde-derived tetrahydroisoquinolines and tetrahydro-β-carbolines in human urine. Journal of Chromatography B: Biomedical Sciences and Applications, 683, 163–176.
20.
GlinwoodR., PetterssonJ., AhmedE., NinkovicV., BirkettM., PickettJ. (2003) Change in acceptability of barley plants to aphids after exposure to allelochemicals from couch-grass (Elytrigia repens). Journal of Chemical Ecology, 29, 261–274.
21.
BlaggJ. (2011) Sepiapterin reductase inhibitors for the treatment of pain.PCT WO, 2011/047156 A1.
