Two new prenylhydroquinone-derived compounds, lentinospirol (1) and 1-(2,5-dihydroxyphenyl)-4-hydroxy-3-methyl-1-butanone (2), were isolated from cultures of the basidiomycete Lentinus similis BCC 52578, together with the known compounds panepoxydone (3), panepoxydione (4), isopanepoxydone (5), 2,2-dimethyl-6-hydroxy-2H-chromene (6), and (3R,4S)-3,4-dihydroxy-2,2-dimethyl-6-methoxychroman (7). Compounds 3 and 4 exhibited cytotoxicity against all cell-lines tested, while the other compounds were inactive.
De SilvaDD, RapiorS, SudarmanE, StadlerM, XuJ, AliasSA, HydeKD. (2013) Bioactive metabolites from macrofungi: ethnopharmacology, biological activities and chemistry. Fungal Diversity, 62, 1–40.
2.
AbateD, AbrahamWR. (1994) Antimicrobial metabolites from Lentinus crinitus. Journal of Antibiotics, 47, 1348–1350.
3.
RukachaisirikulV, TansakulC, SaithongS, PakawatchaiC, IsakaM, SuvannakadR. (2005) Hirsutane sesquiterpenes from the fungus Lentinus connatus BCC 8996. Journal of Natural Products, 68, 1674–1676.
4.
WunderA, AnkeT, KlostermeyerD, SteglichW. (1996) Lactarane type sesquiterpenoids as inhibitors of leukotriene biosynthesis and other, new metabolites from submerged cultures of Lentinus cochleatus. Zeitschrift für Naturforschrung C, 51c, 493–499.
5.
AbrahamWR, AbadeD. (1995) Chromanones from Lentinus crinitus (Basidiomycetes). Zeitschrift für Naturforschrung C, 50c, 748–750.
6.
ZhengY, ZhaoB, LuC, LinX, ZhengZ, SuY. (2009) Isolation, structure elucidation and apoptosis-inducing activity of new compounds from the edible fungus Lentinus striguellus. Natural Product Communications, 4, 501–506.
7.
Barros-FilhoBA, de OliveiraMCF, MafezoliJ, BarbosaFG, Rodrigues-FilhoE. (2012) Pyridone secondary metabolite production by the basidiomycete, Lentinus strigellus, under different culture conditions. Natural Product Communications, 7, 771–773.
8.
IsakaM, SappanM, RachtaweeP, BoonpratuangT. (2011) A tetrahydrofuran derivative from the fermentation broth of Lentinus squarrosulus BCC 22366. Phytochemistry Letters, 4, 106–108.
9.
KisZ, ClosseA, SiggHP, HrubanL, SnatzkeG. (1970) Die structur von panepoxydon und verwandten pilzmetaboliten. Helvetica Chimica Acta, 53, 1577–1597.
10.
ShotwellJB, HuS, MedinaE, AbeM, ColeR, CrewsCM, WoodJL. (2000) Efficient stereoselective synthesis of isopanepoxydone and panepoxydone: a re-assignment of relative configuration. Tetrahedron Letters, 41, 9639–9643.
11.
HowardBM, ClarksonK, BernsteinRL. (1979) Simple prenylated hydroquinone derivatives from the marine urochordate Aplidium californicum. Natural anticancer and antimutagenic agents. Tetrahedron Letters, 20, 4449–4452.
12.
WangQ, SheX, RenX, MaJ, PanX. (2004) The first asymmetric total synthesis of several 3,4-dihydroxy-2,2-dimethyl-chroman derivatives. Tetrahedron: Asymmetry, 15, 29–34.
13.
ErkelG, AnkeT, SternerO. (1996) Inhibition of NF-κB activation by panepoxydone. Biochemical and Biophysical Research Communications, 226, 214–221.
14.
ErkelG, WisserG, AnkeT. (2007) Influence of the fungal NF-κB inhibitor panepoxydone on inflammatory gene expression in MonoMac6 cells. International Immunopharmacology, 7, 612–624.
15.
AroraR, YatesC, GaryBD, McClellanS, TanM, XiY, ReedE, PiazzaGA, OwenLB, Dean-ColombW. (2014) Panepoxydone targets NF-κB and FOXM1 to inhibit proliferation, induce apoptosis and reverse epithelial to mesenchymal transition in breast cancer. PLoS ONE, 9, e98370.
16.
PeglerDN. (1983) The Genus Lentinus: A World Monograph. HMSO, London.
17.
O'BrienJ, WilsonI, OrtonT, PognanF. (2000) Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. European Journal of Biochemistry, 267, 5421–5426.
18.
ChangsenC, FranzblauSG, PalittapongarnpimP. (2003) Improved green fluorescent protein reporter gene-based microplate screening for antituberculosis compounds by utilizing an acetaminase promoter. Antimicrobial Agents and Chemotherapy, 47, 3682–3687.
