Over the past twenty years, our research group has been studying the chemical constituents of mushrooms. From nineteen species, namely, Amanita virgineoides Bas (Amanitaceae), Daedaleopsis tricolor (Bull.: Fr.) Bond. et Sing. (Polyporaceae), Grifola frondosa (Fr.) S. F. Gray (Polyporaceae), Hericium erinaceum (Bull.: Fr.) Pers. (Hericiaceae), Hypsizigus marmoreus (Peck) Bigelow (Tricholomataceae), Lactarius piperatus (Scop.: Fr.) S. F. Gray (Russulaceae), Lentinula edodes (Berk.) Sing. (Pleurotaceae), Lyophyllyum connatum (Schum.: Fr.) Sing. (Tricholomataceae), Naematoloma sublateritium (Fr.) Karst. (Strophariaceae), Ompharia lapidescens Schroeter (Polyporaceae), Panellus serotinus (Pers.: Fr.) Kuhn. (Tricholomataceae), Pholiota nameko (T. Ito) S. Ito et Imai in Imai (Strophariaceae), Pleurotus eringii (DC.: Fr.) Quel. (Pleurotaceae), Polyporus umbellatus Fries (Polyporaceae), Russula delica Fr. (Russulaceae), Russula sanguinea (Bull.) Fr. (Russulaceae), Sarcodon aspratus (Berk.) S. Ito (Thelephoraceae), Tricholoma matsutake (S. Ito et Imai) Sing. (Tricholomataceae), and Tricholoma portentosum (Fr.) Quel. (Tricholomataceae), we isolated eight new sesquiterpenoids, six new meroterpenoids, three new triterpenoids, and twenty eight new sterols. In this review, structural features of these new compounds are discussed.
HansonJ.R. (2008) The Chemistry of Fungi.RSC Publishing, Cambridge, UK, 1–221.
3.
WhittakerR.H. (1969) New concepts of kingdoms or organisms. Evolutionary relations are better represented by new classifications than by the traditional two kingdoms. Science, 163, 150–160.
4.
FushiyaS., WatariF., TashiroT., KusanoG., NozoeS. (1988) A new acidic amino acid from a basidiomycetes, Lactarius piperatus. Chemical & Pharmaceutical Bulletin, 34, 1366–1370.
5.
SternerO., BergmanR., FranzenC., WickbergB. (1985) New sesquiterpenes in a proposed Russulaceae chemical defense system. Tetrahedron Letters, 26, 3163–3166.
6.
WangY., YangS.P., YueJ.M., ChowS., KitchingW. (2003) Novel sesquiterpenes from the fungus Lactarius piperatus. Helvetica Chimica Acta, 86, 2424–2433.
7.
YaoitaY., MachidaK., KikuchiM. (1999) Structures of new marasmane sesquiterpenoids from Lacrarius piperatus (Scop.: Fr.) S. F. Gray. Chemical & Pharmaceutical Bulletin, 47, 894–896.
8.
ClericuzioM., GilardoniG., MalagonO., VidariG., Vita FinziP. (2008) Fungal metabolites. 54. Sesquiterpenes of Lactarius and Russula (mushrooms): an update. Natural Product Communications, 3, 951–974.
9.
ClericuzioM., FuJ., PanF., PanZ., SternerO. (1997) Structure and absolute configuration of protoilludane sesquiterpenes from Russula delica. Tetrahedron, 53, 9735–9740.
10.
ClericuzioM., HanF., PanF., PangZ., SternerO. (1998) The sesquiterpenoid contents of fruit bodies of Russula delica. Acta Chemica Scandinavica, 52, 1333–1337.
11.
YasukawaK., KannoH., KaminagaT., TakidoM., KasaharaY., KumakiK. (1996) Inhibitory effect of methanol extracts from edible mushroom on TPA-induced ear oedema and tumour promotion in mouse skin. Phytotherapy Research, 10, 367–369.
12.
YaoitaY., OnoH., KikuchiM. (2003) A new norsesquiterpenoid from Russula delica Fr. Chemical & Pharmaceutical Bulletin, 51, 1003–1005.
13.
YaoitaY., WatanabeN., TakanoD., KikuchiM. (2004) Sesquiterpenoids from the fruit bodies of Russula delica. Natural Medicines, 58, 235.
14.
JenningsJ.P., KlyneW., ScopesP.M. (1965) Optical rotatory dispersion. XXVI. Some bridged ring lactones. Journal of the Chemical Society, 7229–7237.
15.
ChidaM., YaoitaY., KikuchiM. (2004) Constituents of mushrooms. XXII. Methylation of russulanorol, a norsesquiterpenoid isolated from the fruiting bodies of Russula delica, with trimethylsilyldiazomethane. Journal of Tohoku Pharmaceutical University, 51, 31–34.
16.
YaoitaY., KikuchiM. (2004) Constituents of mushrooms. XXIII. Conformational analysis and absolute structure of lactarorufin B, a sesquiterpenoid isolated from the fruiting bodies of Russula delica. Journal of Tohoku Pharmaceutical University, 51, 35–40.
17.
YaoitaY., HiraoM., KikuchiM., MachidaK. (2012) Three new lactarane sesquiterpenoids from the mushroom Russula sanguinea. Natural Product Communications, 7, 1133–1135.
18.
CornforthJ.W. (1968) Terpenoid biosynthesis. Chemistry in Britain, 4, 102–106.
19.
GerisR., SimpsonJ.T. (2009) Meroterpenoids produced by fungi. Natural Product Reports, 26, 1063–1094.
20.
KawagishiH., AndoM., MizunoT. (1990) Hericenone A and B as cytotoxic principles from the mushroom Hericium erinaceum. Tetrahedron Letters, 31, 373–376.
21.
KawagishiH., AndoM., SakamotoH., YoshidaS., OjimaF., IshiguroY., UkaiN., FurukawaS. (1991) Hericenones C, D and E, simulators of nerve growth factor (NGF) synthesis, from the mushroom Hericium erinaceum. Tetrahedron Letters, 32, 4561–4564.
22.
KawagishiH., AndoM., ShinbaK., SakamotoH., YoshidaS., OjimaF., IshiguroY., UkaiN., FurukawaS. (1992) Chromans, hericenones F, G and H from the mushroom Hericium erinaceum. Phytochemistry, 32, 175–178.
23.
KimuraY., NishibeM., NakajimaH., HamasakiT., ShimadaA., TsunedaA., ShigematsuN. (1991) Hericerin, a new pollen growth inhibitor from the mushroom Hericium erinaceum. Agricultural and Biological Chemistry, 55, 2673–2674.
24.
MiyazawaM., TakahashiT., HoribeI., IshikawaR. (2012) Two new aromatic compounds and a new D-arabinitol ester from the mushroom Hericium erinaceum. Tetrahedron, 68, 2007–2010.
25.
KimK.H., NohH.J., ChoiS.U., LeeK.R. (2012) Isohericenone, a new cytotoxic isoindolinone alkaloid from Hericium erinaceum. The Journal of Antibiotics, 65, 575–577.
26.
RaoA.V.R., ReddyR.G. (1992) First unambiguous total synthesis of hericenone A: proposed structure revised. Tetrahedron Letters, 33, 4061–4064.
27.
YaoitaY., YonezawaS., KikuchiM. (2012) A new geranylated aromatic compound from the mushroom Hericium erinaceum. Natural Product Communications, 7, 527–528.
28.
YaoitaY., DanbaraK., KikuchiM. (2005) Two new aromatic compounds from Hericium erinaceum (Bull.: Fr.) Pers. Chemical & Pharmaceutical Bulletin, 53, 1202–1203.
29.
YaoitaY., KikuchiM. (2005) Constituents of mushrooms. XXV. Structures of new aromatic compounds from the fruiting bodies of Hericium erinaceum (Bull.: Fr.) Rers. Journal of Tohoku Pharmaceutical University, 52, 39–42.
30.
KobayashiS., InoueT., AndoA., TamanoiH., RyuI., MasuyamaA. (2012) Total synthesis and structural revision of hericerin. The Journal of Organic Chemistry, 77, 5819–5822.
31.
Gomez-PradoR.A., MirandaL.D. (2013) Concise total synthesis of hericerin natural product. Tetrahedron Letters, 54, 2131–2132.
32.
YasukawaK., AkihisaT. (2000) Antitumor-promoting activities of sterols and triterpenoids. Journal of Japan Oil Chemists’ Society, 49, 571–582.
33.
OhnumaN., YaoitaY., KakudaR., MachidaK., KikuchiM. (2000) Studies on the constituents of mushrooms. XI. Chemical constituents from the fruiting bodies of Tricholoma matsutake (S. Ito et Imai) Sing. Journal of Tohoku Pharmaceutical University, 47, 67–70.
34.
IijimaT., MatsukiK., YaoitaY., KakudaR., MachidaK., KikuchiM. (2001) Constituents of mushrooms. XIII. Chemical constituents from the fruiting bodies of Panellus serotinus (Pers.: Fr.) Kuhn. and Naematoloma sublateritium (Fr.) Karst. Journal of Tohoku Pharmaceutical University, 48, 77–81.
35.
TanakaN., KitamuraA., MizushinaY., SugawaraF., SakaguchiK. (1998) Fomitellic acid, triterpenoid inhibitors of eukaryotic DNA polymerases from a basidiomycete, Fomitella fraxinea. Journal of Natural Products, 61, 193–197.
36.
YaoitaY., MatsukiK., IijimaT., NakanoS., KakudaR., MachidaK., KikuchiM. (2001) New sterols and triterpenoids from four edible mushrooms. Chemical & Pharmaceutical Bulletin, 49, 589–584.
37.
KimK.H., MoonE., ChoiS.U., KimS.Y., LeeK.R. (2013) Lanostane triterpenoids from the mushroom Naematoloma fasciculare. Journal of Natural Products, 76, 845–851.
38.
KimJ.A., TayD., de BlancoE.C. (2008) NF-κB inhibitory activity of compounds isolated from Cantharellus cbarius. Phytotherapy Research, 22, 1104–1106.
YaoitaY., EndoM., TaniY., MachidaK., AmemiyaK., FurumuraK., KikuchiM. (1999) Sterol constituents from seven mushrooms. Chemical & Pharmaceutical Bulletin, 47, 847–851.
41.
WuJ., FushimiK., TokuyamaS., OhnoM., MiwaT., KoyamaT., YazawaK., NagaiK., MatsumotoT., HiraiH., KawagishiH. (2011) Functional-food constituents in the fruiting bodies of Stropharia rugosoannulata. Bioscience, Biotechnology, and Biochemistry, 75, 1631–1634.
42.
DemarcoP.V., FarkasE., DoddrellD., MylariB.L., WenkertE. (1968) Pyridine-induced solvent shifts in the nuclear magnetic resonance spectra of hydroxylic compounds. Journal of the American Chemical Society, 90, 5480–5486.
43.
YaoitaY., AmemiyaK., OhnumaH., FurumuraK., MasakiA., MatsukiT., KikuchiM. (1998) Sterol constituents from five edible mushrooms. Chemical & Pharmaceutical Bulletin, 46, 944–950.
44.
OhnumaN., AmemiyaK., KakudaR., YaoitaY., MachidaK., KikuchiM. (2000) Sterol constituents from two edible mushrooms, Lentinula edodes and Tricholoma matsutake. Chemical & Pharmaceutical Bulletin, 48, 749–751.
45.
IshizukaT., YaoitaY., KikuchiM. (1997) Sterol constituents from the fruit bodies of Grifola frondosa (Fr.) S. F. Gray. Chemical & Pharmaceutical Bulletin, 45, 1756–1760.
MansoorT.A., LeeY.M., HongJ., LeeC., ImK.S., JungJ.H. (2006) 5,6:8,9-Diepoxy and other cytotoxic sterols from the marine sponge Homaxinella sp. Journal of Natural Products, 69, 131–134.
48.
YaoitaY., YoshiharaY., KakudaR., MachidaK., KikuchiM. (2002) New sterols from two edible mushrooms, Pleurotus eryngii and Panellus serotinus. Chemical & Pharmaceutical Bulletin, 50, 551–553.
49.
OkinoT., YoshimuraE., HirotaH., FusetaniN. (1996) New antifouling sesquiterpenes from four nudibranchs of the family Phyllidiidae. Tetrahedron, 52, 9447–9454.
50.
XuL., KoradeZ., PorterN.A. (2010) Oxysterols from free radical chain oxidation of 7-dehydrocholesterol: product and mechanistic studies. Journal of the American Chemical Society, 132, 2222–2232.
51.
RajeevR., SunojR.B. (2013) Mechanism and stereoselectivity of biologically important oxygenation reactions of the 7-dehydrocholesterol radical. The Journal of Organic Chemistry, 78, 7023–7029.
52.
UenoT., YaoitaY., KakudaR., MachidaK., KikuchiM. (1999) Constituents of mushrooms. VII. On the sterol constituents from the fruit bodies of Sarcodon aspratus. Journal of Tohoku Pharmaceutical University, 46, 71–76.
53.
KishiH., OkabeS., YaoitaY., KikuchiM. (2002) Constituents of mushrooms. XVIII. Chemical constituents from the fruiting bodies of Pholiota terrestris Overholts and Lyophyllum connatum (Schum.: Fr.) Sing. Journal of Tohoku Pharmaceutical University, 49, 85–89.
54.
YaoitaY., YamazakiK., KikuchiM., MachidaK. (2011) Sterols from the mushroom Russula sanguinea. Shoyakugaku Zasshi, 65, 143–144.
55.
OhtaK., YaoitaY., MatsudaN., KikuchiM. (1996) Sterol constituents from the sclerotium of Polyporus umbellatus Fries. Natural Medicines, 50, 179–181.
56.
CiminielloP., FattorussoE., MagnoS., MangoniA., PansiniM. (1990) Incisterols, a new class of highly degraded sterols from the marine sponge Dictyonella incisa. Journal of the American Chemical Society, 112, 3505–3509.
57.
RiccardisF.D., SpinellaA., IzzoI., GiordanoA., SodanoG. (1995) Synthesis of (17R)–17-methylincisterol, a highly degraded marine steroid. Tetrahedron Letters, 36, 4303–4306.
58.
MansoorT.A., HongJ., LeeC., BaeS., ImK.S., JungJ.H. (2005) Cytotoxic sterol derivatives from a marine sponge Homaxinella sp. Journal of Natural Products, 68, 331–336.
59.
KobayashiJ., IshibashiM., NakamuraH., OhizumiY., HirataY. (1989) Hymenosulfate, a novel sterol sulfate with calcium-releasing activity from the cultured marine haptophyte. Journal of the Chemical Society, Perkin Transactions1, 101–103.
60.
BohlinL., SjoestrandU., DjerassiC., SullivanB.W. (1981) Minor and trace sterols in marine invertebrates. Part 20. 3ξ-hydroxymethyl-A-nor-patinosterol and 3ξ-hydroxymethyl-A-nor-dinosterol. Two new sterols with modified nucleus and side-chain from the sponge Teichaxinella morchella. Journal of the Chemical Society, Perkin Transactions1, 1023–1028.
