Chemical investigation of a collection of the fungus Neosartorya glabra from Thailand furnished sartoryglabins A-C (1a, 1b and 2) which are analogs of the reverse prenylated indole alkaloids known as (-) ardeemins. Structures of these compounds were established by NMR spectrometry and an X-ray analysis. Sartoryglabins A-C were evaluated for their in vitro growth inhibitory activity on three human tumor cell lines: MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma). All the compounds exhibited strong to moderate activity against the MCF-7 cell line but weak or no activity against the NCI-H460 and A375-C5 cell lines. Sartoryglabin B was found to exhibit selectivity towards the MCF-7 cell line.
HongS.B., ChoH.S., ShinH.D., FrisvadJ.C., SamsonR.A. (2006) Novel Neosartorya species isolated from soil in Korea. International Journal of Systematic and Evolution of Microbiology, 56, 477–486.
2.
SamsonR.A., HongS., PetersonS.W., FrisvadJ.C., VargaJ. (2007) Polyphasic taxonomy of Aspergillus section Fumigati and its teleomorph Neosartorya. Studies in Mycology, 59, 147–203.
3.
HongS.B., ShinH.D., HongJ., FrisvadJ.C., NielsenP.V., VargaJ., SamsonR.A. (2008) New taxa of Neosartorya and Aspergillus in Aspergillus section Fumigati. Antonie Van Leeuwenhoek, 93, 87–98.
4.
LarsenT.O., SmedsgaardJ., NielsenK.F., HansenM.A.E., SamsomR.A., FrisvadJ.C. (2007) Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati. Medical Mycology, 45, 225–232.
5.
YinW.B., GrundmannA., ChengJ., LiS.M. (2009) Acetylaszonalenin biosynthesis in Neosartorya fischeri. Identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes by biochemical investigation. Journal of Biological Chemistry, 284, 100–109.
6.
YinY.B., XieX.L., MatuscheckM., LiS.M. (2010) Reconstruction of pyrrolo[2,3-b]indoles carrying an alpha-configured reverse C-3 dimethylallyl moiety by using recombinant enzymes. Organic & Biomolecular Chemistry, 8, 1133–1141.
7.
LiS.M. (2009) Application of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products. Applied Microbiology and Biotechnology, 84, 631–639.
8.
YinW.B., ChengJ., LiS.M. (2009) Stereospecific synthesis of aszonalenins by using two recombinant prenyltransferases. Organic & Biomolecular Chemistry, 7, 2202–2207.
9.
LiS.M. (2010) Evolution of aromatic prenyltransferases in the biosynthesis of indole derivatives. Phytochemistry, 70, 1746–1757.
10.
LiS.M. (2010) Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis. Natural Product Reports, 27, 57–78.
11.
JayasuriyaH., ZinkD., BasilioA., VicenteF., ColladoJ.BillsG., GoldmanM.L., MotylM., HuberJ., DezenyG., ByrneK., SinghS.B. (2009) Discovery and antibiotic activity of glabramycin A-C from Neosartorya glabra by an antisense strategy. The Journal of Antibiotics, 62, 265–269.
12.
KarwowskiJ.P., JacksonM., RasmussenR.R., HumphreyP.E., PoddigJ.P., KohlW.L., CherrM.H., KadamS., McAlpineJ.B. (1993) 5-N-Acetylardeemin, a novel heterocyclic compound which reverses multiple drug resistance in tumor cells. I. Taxonomy and fermentation of the prpducing organism and biological activity. The Journal of Antibiotics, 46, 374–379.
13.
HochlowskiJ.E., MullallyM.M., SpantonS.G., WhitternD.N., PrestonH., McAlpineJ.B. (1993) 5-N-Acetylardeemin, a novel heterocyclic compound which reverses multiple drug resistance in tumor cells. II. Isolation and elucidation of the structure of 5-N-acetylardeemin and two congeners. The Journal of Antibiotics, 46, 380–386.
14.
ChouT.C., DepewK.M., ZhengY.H., SaferM.L., ChanD., HelfridchB., ZatorskaD., ZartoskiA., BornmannW.G., DanishefskyS.J. (1998) Reverseal of anticancer multiple resistance by the ardeemins. Proceedings of the National Academy of Sciences of the United States of America, 95, 8369–8374.
15.
MarsdenS.P., DepewK.M., DanishefskyS.J. (1994) Stereoselective total synthesis of amauromine and 5-N-acetylardeemin. A concise route to the family of “Reverse Prenylated” hexahydropyrroloindole alkaloids. Journal of the American Chemical Society, 116, 11143–11144.
16.
DepewK.M., MarsdenS.P., ZatorskaD., ZartoskiA., BornmannW.G., DanishefskyS.J. (1999) Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agent. Journal of the American Chemical Society, 121, 11953–11963.
17.
HeB., SongH., DuY., QinY. (2009) Total synthesis of (-) ardeemin. The Journal of Organic Chemistry, 74, 298–304.
18.
GeH.M., PengH., GuoZ.K., CuiJ.T., SongY.C., TanR.X. (2010) Bioactive alkaloids from the plant endophytic fungus Aspergillus terreus. Planta Medica, 76, 822–824.
19.
SheldrickG.M. (1997) SHELXS-97: Program for the Solution of Crystal Structures, University of Gottingen, Germany.
20.
SheldrickG.M. (1997) SHELXS-97: Program for the Refinement of Crystal Structures, University of Gottingen, Germany.
21.
VazJ.A., HelenoS.A., MartinsA., AlmeidaG.M., VasconcelosM.H., FerreiraI. (2010) Wild mushroom Clitocybe alexandri and Lepista inversa: In vitro antioxidant activity and growth inhibition of human tumor cell lines. Food and Chemical Toxicology, 48, 2881–2884.
22.
MonksA., ScudieroD., SkehanP., ShoemakerR., PaulK., VisticaD., HoseC., LangleyJ., CroniseP., Vaigro-WolffA., Gray-GoodrichM., CampbelH., MayoJ., BoydM. (1991) Feasibility of a high-flux anticancer drugs screen using a diverse panel of cultured human cell line. Journal of the National Cancer Institute, 83, 757–776.
