Abstract
Basidiomycetes, a major class of higher fungi adapted to many different climates, habitats, and substrates, have developed a rich and very diverse secondary metabolism. Its products differ in biogenetic origin and structure remarkably from the metabolites of ascomycetes or other prolific producers of secondary metabolites like actinomycetes or myxobacteria. There are, however, some similarities to the products of plants, especially with regard to some polyketides, acetylenes, and sesquiterpenoids. It is noteworthy that many basidiomycete metabolites exhibit interesting biological activities, which in some cases led to the development of very successful plant protectants or antibiotics for human and veterinary uses.
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References
Abraham W-R (2001) Bioactive sesquiterpenes produced by fungi: are they useful for humans as well? Curr Med Chem 8:583–606. https://doi.org/10.2174/0929867013373147
Agger S, Lopez-Gallego F, Schmidt-Dannert C (2009) Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus. Mol Microbiol 72:1181–1195. https://doi.org/10.1111/j.1365-2958.2009.06717.x
Andernach L, Opatz T (2014) Assignment of the absolute configuration and total synthesis of (+)-caripyrin. Eur J Org Chem 2014:4780–4784. https://doi.org/10.1002/ejoc.201402540
Aqueveque P, Anke T, Sterner O (2002) The himanimides, new bioactive compounds from Serpula himantioides (Fr.)Karst. Z Naturforsch C J Biosci 57:257–262. https://doi.org/10.1515/znc-2002-3-410
Asakawa Y, Hashimoto T (1998) Biologically active substances of Japanese inedible mushrooms. Heterocycles 47:1067. https://doi.org/10.3987/REV-97-SR(N)6
Asakawa Y, Hashimoto T, Mizuno Y et al (1992) Cryptoporic acids A-G, drimane-type sesquiterpenoid ethers of isocitric acid from the fungus Cryptoporus volvatus. Phytochemistry 31:579–592. https://doi.org/10.1016/0031-9422(92)90042-O
Ayer WA, Cruz ER (1993) The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae. J Org Chem 58(26):7529–7534
Ayer WA, Shan R, Trifonov LS, Hutchison LJ (1998) Sesquiterpenes from the nematicidal fungus Clitocybula oculus in honour of professor G. H. Neil Towers 75th birthday. Phytochemistry 49:589–592. https://doi.org/10.1016/S0031-9422(98)00173-3
Bai R, Zhang CC, Yin X et al (2015) Striatoids A-F, cyathane diterpenoids with neurotrophic activity from cultures of the fungus Cyathus striatus. J Nat Prod 78:783–788. https://doi.org/10.1021/np501030r
Basavaiah D, Devendar B, Aravindu K, Veerendhar A (2010) A facile one-pot transformation of Baylis-Hillman adducts into unsymmetrical disubstituted maleimide and maleic anhydride frameworks: a facile synthesis of himanimide A. Chem Eur J 16(2031–2035):S2031/1–S2031/59. https://doi.org/10.1002/chem.200902887
Baumann C, Bröckelmann M, Fugmann B et al (1993) Haematopodin, an unusual pyrroloquinoline derivative isolated from the fungus Mycena haematopus, agaricales. Angew Chem Int Ed Eng 32:1087–1089. https://doi.org/10.1002/anie.199310871
Bertinetti B, Scandiani M, Cabrera G (2011) Analogs of antifungal indoles isolated from Aporpium caryae with activity against sudden-death syndrome of soybean. Am J Plant Sci 2:245–254. https://doi.org/10.4236/ajps.2011.22026
Bette E, Otto A, Dräger T et al (2015) Isolation and asymmetric total synthesis of fungal secondary metabolite hygrophorone B12. Eur J Org Chem 2015:2357–2365. https://doi.org/10.1002/ejoc.201403455
Borgström B (1988) Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin. Biochim Biophys Acta 962:308–316
Breheret S, Talou T, Rapior S, Bessiere J-M (1999) Geosmin, a sesquiterpenoid compound responsible for the musty-earthy odor of Cortinarius herculeus, Cystoderma amianthinum, and Cy. carcharias. Mycologia 91:117. https://doi.org/10.2307/3761199
Bresinsky A, Besl H (1985) Giftpilze. Wissenschaftliche Verlagsgesellschaft, Stuttgart
Bunyapaiboonsri T, Yoiprommarat S, Nopgason R et al (2014) Cadinane sesquiterpenoids from the basidiomycete Stereum cf. sanguinolentum BCC 22926. Phytochemistry 105:123–128. https://doi.org/10.1016/j.phytochem.2014.06.006
Cabrera GM, Roberti MJ, Wright JE, Seldes AM (2002) Cryptoporic and isocryptoporic acids from the fungal cultures of Polyporus arcularius and P. ciliatus. Phytochemistry 61:189–193. https://doi.org/10.1016/S0031-9422(02)00221-2
Cali V, Spatafora C, Tringali C (2004) Sarcodonins and sarcoviolins, bioactive polyhydroxy-p-terphenyl pyrazinediol dioxide conjugates from fruiting bodies of the basidiomycete Sarcodon leucopus. Eur J Org Chem 2004(3):592–599. https://doi.org/10.1002/ejoc.200300407
Cazal CM, Choosang K, Severino VGP et al (2010) Evaluation of effect of triterpenes and limonoids on cell growth, cell cycle and apoptosis in human tumor cell lines. Anti Cancer Agents Med Chem 10:769–776
Chen H-P, Zhao Z-Z, Yin R-H et al (2014) Six new vibralactone derivatives from cultures of the fungus Boreostereum vibrans. Nat Prod Bioprospect 4:271–276. https://doi.org/10.1007/s13659-014-0029-z
Chen CC, Tzeng TT, Chen CC et al (2016a) Erinacine S, a rare sesterterpene from the mycelia of Hericium erinaceus. J Nat Prod 79:438–441. https://doi.org/10.1021/acs.jnatprod.5b00474
Chen H-P, Zhao Z-Z, Li Z-H et al (2016b) Novel natural oximes and oxime esters with a vibralactone backbone from the basidiomycete Boreostereum vibrans. ChemistryOpen 5:142–149. https://doi.org/10.1002/open.201500198
Cheng C-F, Lai Z-C, Lee Y-J (2008) Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction. Tetrahedron 64:4347–4353. https://doi.org/10.1016/j.tet.2008.02.077
Chepkirui C, Richter C, Matasyoh JC, Stadler M (2016) Monochlorinated calocerins A-D and 9-oxostrobilurin derivatives from the basidiomycete Favolaschia calocera. Phytochemistry 132:95–101. https://doi.org/10.1016/j.phytochem.2016.10.001
Chudzik M, Korzonek-Szlacheta I, Król W (2015) Triterpenes as potentially cytotoxic compounds. Molecules 20:1610–1625. https://doi.org/10.3390/molecules20011610
Clericuzio M, Sterner O (1997) Conversion of velutinal esters in the fruit bodies of Russula cuprea. Phytochemistry 45:1569–1572. https://doi.org/10.1016/S0031-9422(97)00259-8
Colland F (2010) The therapeutic potential of deubiquitinating enzyme inhibitors. Biochem Soc Trans 38:137–143. https://doi.org/10.1042/BST0380137
Daum RS, Kar S, Kirkpatrick P (2007) Retapamulin. Nat Rev Drug Discov 6:865–866. https://doi.org/10.1038/nrd2442
Davoli P, Mucci A, Schenetti L, Weber RWS (2005) Laetiporic acids, a family of non-carotenoid polyene pigments from fruit-bodies and liquid cultures of Laetiporus sulphureus (Polyporales, Fungi). Phytochemistry 66:817–823. https://doi.org/10.1016/j.phytochem.2005.01.023
De Silva DD, Rapior S, Sudarman E et al (2013) Bioactive metabolites from macrofungi: ethnopharmacology, biological activities and chemistry. Fungal Divers 62:1–40. https://doi.org/10.1007/s13225-013-0265-2
Dekker FJ, Rocks O, Vartak N et al (2010) Small-molecule inhibition of APT1 affects Ras localization and signaling. Nat Chem Biol 6:449–456. https://doi.org/10.1038/nchembio.362
Dong M, Chen S-P, Kita K et al (2009) Anti-proliferative and apoptosis-inducible activity of Sarcodonin G from Sarcodon scabrosus in HeLa cells. Int J Oncol 34:201–207. https://doi.org/10.3892/ijo_00000142
Engler-Lohr M, Ankea T, Hellwig V, Steglich W (1999) Noroudemansin A, a new antifungal antibiotic from Pterula species 82168 and three semisynthetic derivatives. Z Naturforsch C J Biosci 54:163–168
Evans L, Hedger J, O’Donnell G et al (2010) Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus. Tetrahedron Lett 51:5493–5496. https://doi.org/10.1016/j.tetlet.2010.08.036
Fabian K, Lorenzen K, Anke T et al (1998) Five new bioactive sesquiterpenes from the fungus Radulomyces confluens (Fr.) Christ. Z Naturforsch C J Biosci 53:939–945
Fang S-T, Zhang L, Li Z-H et al (2010) Cyathane diterpenoids and nitrogenous terphenyl derivative from the fruiting bodies of basidiomycete Phellodon niger. Chem Pharm Bull 58:1176–1179. https://doi.org/10.1248/cpb.58.1176
Fang S-T, Feng T, Zhang L et al (2011) Cyathane diterpenoids from fruiting bodies of Phellodon niger. Nat Prod Bioprospect 1:37–40. https://doi.org/10.1007/s13659-011-0002-z
Feng T, Li Z-H, Dong Z-J et al (2011) Non-isoprenoid botryane sesquiterpenoids from basidiomycete Boletus edulis and their cytotoxic activity. Nat Prod Bioprospect 1(1):29–32. https://doi.org/10.1007/s13659-011-0005-9
Feng Y, Wang L, Niu S et al (2012) Naphthalenones from a Perenniporia sp. inhabiting the larva of a phytophagous weevil, Euops chinesis. J Nat Prod 75:1339–1345. https://doi.org/10.1021/np300263u
Florey H, Chain E, Heatley N et al (1949) Antibiotics. A survey of penicillin, streptomycin, and other antimicrobial substances from fungi, actinomycetes, bacteria, and plants. Oxford University Press, Oxford
Fraga BM (2009) Natural sesquiterpenoids. Nat Prod Rep 26:1125–1155. https://doi.org/10.1039/B908720F
Fraga BM (2010) Natural sesquiterpenoids. Nat Prod Rep 27:1681–1708. https://doi.org/10.1039/C0NP00007H
Fraga BM (2011) Natural sesquiterpenoids. Nat Prod Rep 30:1226. https://doi.org/10.1039/c3np70047j
Fraga BM (2012) Natural sesquiterpenoids. Nat Prod Rep 29:1334–1366. https://doi.org/10.1039/C2NP20074K
Fraga BM (2013) Natural sesquiterpenoids. Nat Prod Rep 30:1226. https://doi.org/10.1039/c3np70047j
Froufe HJC, Abreu RMV, Ferreira ICFR (2013) Virtual screening of low molecular weight mushrooms compounds as potential Mdm2 inhibitors. J Enzyme Inhib Med Chem 28:569–575. https://doi.org/10.3109/14756366.2012.658787
Fukuda T, Tomoda H (2013) Tylopilusin C, a new diphenolic compound from the fruiting bodies of Tylopilus eximinus. J Antibiot 66:355–357. https://doi.org/10.1038/ja.2013.23
Fukuda T, Nagai K, Tomoda H (2012) (±)-Tylopilusins, diphenolic metabolites from the fruiting bodies of Tylopilus eximius. J Nat Prod 75:2228–2231. https://doi.org/10.1021/np300428r
Gao L, Han J, Si J et al (2017) Cryptoporic acid E from Cryptoporus volvatus inhibits influenza virus replication in vitro. Antivir Res 143:106–112. https://doi.org/10.1016/j.antiviral.2017.02.010
Gehrt A, Erkel G, Anke T, Sterner O (1998) Nitidon, a new bioactive metabolite from the basidiomycete Junghuhnia nitida (Pers.: Fr.) Ryv. Z Naturforsch C J Biosci 53:89–92
Geraci C, Neri P, Paterno C et al (2000) An unusual nitrogenous terphenyl derivative from fruiting bodies of the basidiomycete Sarcodon leucopus. J Nat Prod 63:347–351. https://doi.org/10.1021/np990293d
Gilardoni G, Clericuzio M, Tosi S et al (2007) Antifungal acylcyclopentenediones from fruiting bodies of Hygrophorus chrysodon. J Nat Prod 70:137–139. https://doi.org/10.1021/np060512c
Gill M (1999) Pigments of fungi (Macromycetes). Nat Prod Rep 16:301–317. https://doi.org/10.1039/a705730j
Gill M, Steglich W (1987) Pigments of fungi (Macromycetes). In: Zechmeier L (ed) Progress in the chemistry of organic natural products, vol 51. Springer, Heidelberg, pp 1–297
Hadváry P, Lengsfeld H, Wolfer H (1988) Inhibition of pancreatic lipase in vitro by the covalent inhibitor tetrahydrolipstatin. Biochem J 256:357–361
Han J-J, Bao L, He L-W et al (2013a) Phaeolschidins A-E, five hispidin derivatives with antioxidant activity from the fruiting body of Phaeolus schweinitzii collected in the tibetan plateau. J Nat Prod 76:1448–1453. https://doi.org/10.1021/np400234u
Han JJ, Chen YH, Bao L et al (2013b) Anti-inflammatory and cytotoxic cyathane diterpenoids from the medicinal fungus Cyathus africanus. Fitoterapia 84:22–31. https://doi.org/10.1016/j.fitote.2012.10.001
Han J-J, Zhang L, Xu J-K et al (2015) Three new cyathane diterpenoids from the medicinal fungus Cyathus africanus. J Asian Nat Prod Res 17:541–549. https://doi.org/10.1080/10286020.2015.1043900
Hanpude P, Bhattacharya S, Dey A, Maiti T (2015) Critical review: Deubiquitinating enzymes in cellular signaling and disease regulation enzymatic mechanism of DUBs. IUBMB Life 67:544–555. https://doi.org/10.1002/iub.1402
Hasegawa M, Akabori Y, Akabori S (1974) New indanone compounds from Onychium japonicum. Phytochemistry 13:509–511. https://doi.org/10.1016/S0031-9422(00)91246-9
Hashimoto T, Tori M, Mizuno Y, Asakawa Y (1987) Cryptoporic acids A and B, novel bitter drimane sesquiterpenoid ethers of isocitric acid, from the fungus Cryptoporus volvatus (Polyporaceae). Tetrahedron Lett 28:6303–6304. https://doi.org/10.1016/S0040-4039(01)91358-9
Hashimoto T, Tori M, Mizuno Y et al (1989) The superoxide release inhibitors, cryptoporic acids C, D, and E; dimeric drimane sesquiterpenoid ethers of isocitric acid from the fungus Cryptoporus volvatus. J Chem Soc Chem Commun 1989:258–259. https://doi.org/10.1039/c39890000258
He L, Han J, Li B et al (2016) Identification of a new cyathane diterpene that induces mitochondrial and autophagy-dependent apoptosis and shows a potent in vivo anti-colorectal cancer activity. Eur J Med Chem 111:183–192. https://doi.org/10.1016/j.ejmech.2016.01.056
Hellwig V, Dasenbrock J, Gräf C et al (2002) Calopins and cyclocalopins – bitter principles from Boletus calopus and related mushrooms. Eur J Org Chem 2002:2895–2904. https://doi.org/10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S
Hendriks IA, Vertegaal ACO (2016) A comprehensive compilation of SUMO proteomics. Nat Rev Mol Cell Biol 17:581–595. https://doi.org/10.1038/nrm.2016.81
Hill RA, Connolly JD (2015) Triterpenoids. Nat Prod Rep 32:273–327. https://doi.org/10.1039/C4NP00101J
Hirota M, Morimura K, Shibata H (2002) Anti-inflammatory compounds from the bitter mushroom, Sarcodon scabrosus. Biosci Biotechnol Biochem 66:179–184. https://doi.org/10.1271/bbb.66.179
Hirotani M, Furuya T, Shiro M (1991) Studies on the metabolites of higher fungi. Part 10. Cryptoporic acids H and I, drimane sesquiterpenes from Ganoderma neo-japonicum and Cryptoporus volvatus. Phytochemistry 30:1555–1559. https://doi.org/10.1016/0031-9422(91)84208-A
Ho C-L, Cheng H, Chen MC-M, Ettinger DS (2015) Antroquinonol to block Ras and Rho signaling via the inhibition of protein isoprenyltransferase activity in cancer cells. J Clin Oncol 33:e18526–e18526. https://doi.org/10.1200/jco.2015.33.15_suppl.e18526
Högenauer G (1979) Tiamulin and pleuromutilin. In: Hahn F (ed) Mechanism of action of antibacterial agents. Springer, Berlin, Heidelberg, pp 344–360
Hoppmann CD, Kurz MD, Müller G, Toti LD (2001) Inventors; Aventis pharma Deutschland GmbH, assignee. Percyquinnin, a process for its production and its use as a pharmaceutical. European patent EP1142886 (A1)
Hsu C-S, Chou H-H, Fang J-M (2015) A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone. Org Biomol Chem 13:5510–5519. https://doi.org/10.1039/C5OB00411J
Hu D, Li W, Zhao Z et al (2014) Highly unsaturated pyranone derivatives from the basidiomycete Junghuhnia nitida. Tetrahedron Lett 55:6530–6533. https://doi.org/10.1016/j.tetlet.2014.09.132
Huang Z, Dan Y, Huang Y et al (2004) Sesquiterpenes from the mycelial cultures of Dichomitus squalens. J Nat Prod 67:2121–2123. https://doi.org/10.1021/np0497144
Huang L, Han J, Ben-Hail D, He L, Li B, Chen Z, Wang Y, Yang Y, Liu L, Zhu Y, Shoshan-Barmatz V, Liu H, Chen Q (2015) A new fungal diterpene induces VDAC1-dependent apoptosis in bax/bak-deficient cells. J Biol Chem 290(39):23563–23578
IndexFungorum Index Fungorum. www.indexfungorum.org. Accessed 20 June 2017
Isaka M, Srisanoh U, Sappan M et al (2012) Sterostreins F–O, illudalanes and norilludalanes from cultures of the basidiomycete Stereum ostrea BCC 22955. Phytochemistry 79:116–120. https://doi.org/10.1016/j.phytochem.2012.04.009
Isaka M, Chinthanom P, Danwisetkanjana K, Choeyklin R (2014a) A new cryptoporic acid derivative from cultures of the basidiomycete Poria albocincta BCC 26244. Phytochem Lett 7:97–100. https://doi.org/10.1016/j.phytol.2013.10.009
Isaka M, Chinthanom P, Sappan M, Supothina S (2014b) Phenylglycol metabolites from cultures of the basidiomycete Mycena pruinosoviscida BCC 22723. Helv Chim Acta 97:909–914
Isaka M, Chinthanom P, Sappan M, Danwisetkanjana K (2016a) Antitubercular lanostane triterpenes from cultures of the basidiomycete Ganoderma sp. BCC 16642. J Nat Prod 79(1):161–169. https://doi.org/10.1021/acs.jnatprod.5b00826
Isaka M, Palasarn S, Sappan M et al (2016b) Hirsutane sesquiterpenes from cultures of the basidiomycete Marasmiellus sp. BCC 22389. Nat Prod Bioprospect 6:257–260. https://doi.org/10.1007/s13659-016-0105-7
Isaka M, Palasarn S, Supothina S et al (2016c) Seco-Tremulanes from cultures of the basidiomycete Flavodon flavus BCC 17421. Helv Chim Acta 99:232–236. https://doi.org/10.1002/hlca.201500249
Ishikawa NK, Yamaji K, Tahara S et al (2000) Highly oxidized cuparene-type sesquiterpenes from a mycelial culture of Flammulina velutipes. Phytochemistry 54:777–782. https://doi.org/10.1016/S0031-9422(00)00189-8
Ishikawa NK, Fukushi Y, Yamaji K et al (2001) Antimicrobial cuparene-type sesquiterpenes, enokipodins C and D, from a mycelial culture of Flammulina velutipes. J Nat Prod 64:932–934. https://doi.org/10.1021/np000593r
Ito-Kobayashi M, Aoyagi A, Tanaka I et al (2008) Sterenin A, B, C and D, novel 11β-hydroxysteroid dehydrogenase type 1 inhibitors from Stereum sp. SANK 21205. J Antibiot 61:128–135. https://doi.org/10.1038/ja.2008.121
Jaeger RJR, Spiteller P (2010) Mycenaaurin A, an antibacterial polyene pigment from the fruiting bodies of Mycena aurantiomarginata. J Nat Prod 73:1350–1354. https://doi.org/10.1021/np100155z
Jaeger RJR, Lamshöft M, Gottfried S et al (2013) HR-MALDI-MS imaging assisted screening of beta-Carboline alkaloids discovered from Mycena metata. J Nat Prod 76:127–134. https://doi.org/10.1021/np300455a
JGI (2016) Joint Genome Institute. http://genome.jgi.doe.gov/programs/fungi/index.jsf. Accessed 12 December 2016
Jiang M-Y, Wang F, Yang X-L et al (2008) Derivatives of vibralactone from cultures of the basidiomycete Boreostereum vibrans. Chem Pharm Bull 56:1286–1288. https://doi.org/10.1248/cpb.56.1286
Jiang M-Y, Zhang L, Liu R et al (2009) Speciosins A-K, oxygenated cyclohexanoids from the basidiomycete Hexagonia speciosa. J Nat Prod 72:1405–1409. https://doi.org/10.1021/np900182m
Jiang M, Zhang L, Dong Z et al (2010) Vibralactones D-F from cultures of the basidiomycete Boreostereum vibrans. Chem Pharm Bull (Tokyo) 58:113–116. https://doi.org/10.1248/cpb.58.113
Jiang M-Y, Li Y, Wang F, Liu J-K (2011) Isoprenylated cyclohexanoids from the basidiomycete Hexagonia speciosa. Phytochemistry (Elsevier) 72:923–928. https://doi.org/10.1016/j.phytochem.2011.03.011
Johansson M, Sterner O, Labischinski H, Anke T (2001) Coprinol, a new antibiotic cuparane from a Coprinus species. Z Naturforsch C J Biosci 56:31–34
Jones RN, Fritsche TR, Sader HS, Ross JE (2006) Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci. Antimicrob Agents Chemother 50:2583–2586. https://doi.org/10.1128/AAC.01432-05
Jülich C, Nord CL, Menkis A et al (2013) Protoilludane sesquiterpenes from the wood decomposing fungus Granulobasidium vellereum (Ellis & Cragin) Jülich. Phytochemistry 90:128–134. https://doi.org/10.1016/j.phytochem.2013.02.015
Kahner L, Dasenbrock J, Spiteller P et al (1998) Polyene pigments from fruit-bodies of Boletus laetissimus and B. rufo-aureus (Basidiomycetes). Phytochemistry 49:1693–1697. https://doi.org/10.1016/S0031-9422(98)00319-7
Kalb D, Lackner G, Hoffmeister D (2013) Fungal peptide synthetases: an update on functions and specificity signatures. Fungal Biol Rev 27:43–50. https://doi.org/10.1016/j.fbr.2013.05.002
Kamo T, Imura Y, Hagio T et al (2004) Anti-inflammatory cyathane diterpenoids from Sarcodon scabrosus. Biosci Biotechnol Biochem 68:1362–1365. https://doi.org/10.1271/bbb.68.1362
Kang H-S, Kim J-P (2016) Ostalactones A–C, β- and ε-lactones with lipase inhibitory activity from the cultured basidiomycete Stereum ostrea. J Nat Prod 79:3148–3151. https://doi.org/10.1021/acs.jnatprod.6b00647
Kavanagh F, Hervey A, Robbins WJ (1951) Antibiotic substances from basidiomycetes: VIII. Pleurotus multilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat. Proc Natl Acad Sci USA 37:570–574
Kawagishi H, Zhuang C (2008) Compounds for dementia from Hericium erinaceum. Drugs Future 33:149. https://doi.org/10.1358/dof.2008.033.02.1173290
Kawai T, Mizutani S, Enoki T et al (2005) Inventors; Takara Bio Inc., assignee. Antitumor agent. WO2005115364 A1
Kettering M, Sterner O, Anke T (2004) Antibiotics in the chemical communication of fungi. Z Naturforsch C J Biosci 59:816–823
Ki D-W, Kim D-W, Hwang BS et al (2015) New antioxidant sesquiterpenes from a culture broth of Coprinus echinosporus. J Antibiot 68:351–353. https://doi.org/10.1038/ja.2014.158
Kim H-J, Vinale F, Ghisalberti EL et al (2006) An antifungal and plant growth promoting metabolite from a sterile dark ectotrophic fungus. Phytochemistry 67:2277–2280. https://doi.org/10.1016/j.phytochem.2006.07.022
Kim KH, Moon E, Choi SU et al (2013) Lanostane triterpenoids from the mushroom Naematoloma fasciculare. J Nat Prod 76:845–851. https://doi.org/10.1021/np300801x
Kim SO, Sakchaisri K, Asami Y et al (2014) Illudins C2 and C3 stimulate lipolysis in 3T3-L1 adipocytes and suppress adipogenesis in 3T3-L1 preadipocytes. J Nat Prod 77:744–750. https://doi.org/10.1021/np400520a
Kita T, Takaya Y, Oshima Y et al (1998) Scabronines B, C, D, E, F, novel diterpenoids showing stimulating activity of nerve growth factor-synthesis, from the mushroom Sarcodon scabrosus. Tetrahedron 54:11877–11886. https://doi.org/10.1016/S0040-4020(98)83045-7
Klaiklay S, Rukachaisirikul V, Phongpaichit S et al (2012) Flavodonfuran: a new difuranylmethane derivative from the mangrove endophytic fungus Flavodon flavus PSU-MA201. Nat Prod Res 27:1722. https://doi.org/10.1080/14786419.2012.750315
Kokubun T, Scott-Brown A, Kite GC, Simmonds MSJ (2016) Protoilludane, illudane, illudalane, and norilludane sesquiterpenoids from Granulobasidium vellereum. J Nat Prod 79:1698–1701. https://doi.org/10.1021/acs.jnatprod.6b00325
Kornsakulkarn J, Thongpanchang C, Chainoy R et al (2010) Bioactive metabolites from cultures of basidiomycete Favolaschia tonkinensis. J Nat Prod 73:759–762
Lee I, Jeong C, Cho S et al (1996) Illudins C2 and C3, new illudin C derivatives from Coprinus atramentarius ASI20013. J Antibiot 49:821–822
Lee T-H, Lee C-K, Tsou W-L et al (2007) A new cytotoxic agent from solid-state fermented mycelium of Antrodia camphorata. Planta Med 73:1412–1415. https://doi.org/10.1055/s-2007-990232
Lee JS, Maarisit W, Abdjul DB et al (2016) Structures and biological activities of triterpenes and sesquiterpenes obtained from Russula lepida. Phytochemistry 127:63–68. https://doi.org/10.1016/j.phytochem.2016.03.014
Levy LM, Cabrera GM, Wright JE, Seldes AM (2000) Indole alkaloids from a culture of the fungus Aporpium caryae. Phytochemistry 54:941–943. https://doi.org/10.1016/S0031-9422(00)00127-8
Levy LM, Cabrera GM, Wright JE, Seldes AM (2003) 5H-Furan-2-ones from fungal cultures of Aporpium caryae. Phytochemistry (Elsevier) 62:239–243. https://doi.org/10.1016/S0031-9422(02)00455-7
Li G-H, Duan M, Yu Z-F et al (2008) Stereumin A-E, sesquiterpenoids from the fungus Stereum sp. CCTCC AF 207024. Phytochemistry 69:1439–1445. https://doi.org/10.1016/j.phytochem.2008.01.012
Li G, Liu F, Shen L et al (2011) Stereumins H-J, stereumane-type sesquiterpenes from the fungus Stereum sp. J Nat Prod 74:296–299. https://doi.org/10.1021/np100813f
Liermann JC, Schüffler A, Wollinsky B et al (2010) Hirsutane-type sesquiterpenes with uncommon modifications from three basidiomycetes. J Org Chem 75:2955–2961. https://doi.org/10.1021/jo100202b
Liermann JC, Thines E, Opatz T, Anke H (2012) Drimane sesquiterpenoids from Marasmius sp. Inhibiting the conidial germination of plant-pathogenic fungi. J Nat Prod 75:1983–1986. https://doi.org/10.1021/np300337w
Lin J, Wang R, Xu G et al (2016) New cadinane sesquiterpenoids from the basidiomycetous fungus Pholiota sp. RSC Adv 6:112527–112533. https://doi.org/10.1039/C6RA22448B
List A, Zeiler E, Gallastegui N et al (2014) Omuralide and vibralactone: differences in the proteasome-beta-lactone-gamma-lactam binding scaffold alter target preferences. Angew Chem Int Ed 53:571–574. https://doi.org/10.1002/anie.201308567
Liu J-K (2006) Natural terphenyls: developments since 1877. Chem Rev 106:2209–2223. https://doi.org/10.1021/cr050248c
Liu D-Z (2014) A review of ergostane and cucurbitane triterpenoids of mushroom origin. Nat Prod Res 28:1099–1105. https://doi.org/10.1080/14786419.2014.900767
Liu D-Z, Wang F, Liao T-G et al (2006) Vibralactone: a lipase inhibitor with an unusual fused β-lactone produced by cultures of the basidiomycete Boreostereum vibrans. Org Lett 8:5749–5752. https://doi.org/10.1021/ol062307u
Liu D-Z, Wang F, Liu J-K (2007) Sesquiterpenes from cultures of the basidiomycete Conocybe siliginea. J Nat Prod 70:1503–1506. https://doi.org/10.1021/np070140n
Liu D-Z, Jia R-R, Wang F, Liu J-K (2008a) A new spiroaxane sesquiterpene from cultures of the basidiomycete Pholiota adiposa. Z Naturforsch B Chem Sci 63:111–113
Liu DZ, Wang F, Jia RR, Liu JK (2008b) A novel sesquiterpene from the basidiomycete Boletus calopus. Z Naturforsch B J Chem Sci 63:114–116
Liu YJ, Liu Y, Zhang KQ (2008c) Xanthothone, a new nematicidal N-compound from Coprinus xanthothrix. Chem Nat Compd 44:203–205. https://doi.org/10.1007/s10600-008-9014-2
Liu F-F, Li G-H, Yang Z-S et al (2010) Two new sesquiterpenes from the fungus Stereum sp. Helv Chim Acta 93:1737–1741. https://doi.org/10.1002/hlca.200900433
Liu L, Shi X-W, Zong S-C et al (2012) Scabronine M, a novel inhibitor of NGF-induced neurite outgrowth from PC12 cells from the fungus Sarcodon scabrosus. Bioorg Med Chem Lett 22:2401–2406. https://doi.org/10.1016/j.bmcl.2012.02.031
Liu L-Y, Li Z-H, Si J et al (2013) Two new sesquiterpenoids from the fungus Ceriporia alachuana. J Asian Nat Prod Res 15:300–304. https://doi.org/10.1080/10286020.2013.763798
Long KS, Hansen LH, Jakobsen L, Vester B (2006) Interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center. Antimicrob Agents Chemother 50(4):1458–1462
Lopez-Gallego F, Agger SA, Abate-Pella D et al (2010) Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers. ChemBioChem 11:1093–1106. https://doi.org/10.1002/cbic.200900671
Lorenzen K, Anke T (1998) Biologically active metabolites from basidiomycetes. Curr Org Chem 2:329–364
Lu M-C, El-Shazly M, Wu T-Y et al (2013) Recent research and development of Antrodia cinnamomea. Pharmacol Ther 139:124–156. https://doi.org/10.1016/j.pharmthera.2013.04.001
Luana G, Fabiano S, Fabio G, Paolo G (2015) Comparing visual inspection of trees and molecular analysis of internal wood tissues for the diagnosis of wood decay fungi. Forestry 88:465–470. https://doi.org/10.1093/forestry/cpv015
Lübken T (2006) Hygrophorone, neue antifungische Cyclopentenonderivate aus Hygrophorus-Arten. PhD thesis, University of Halle, Halle, Germany
Lübken T, Schmidt J, Porzel A et al (2004) Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes). Phytochemistry 65:1061–1071. https://doi.org/10.1016/j.phytochem.2004.01.023
Lübken T, Arnold N, Wessjohann L et al (2006) Analysis of fungal cyclopentenone derivatives from Hygrophorus spp. by liquid chromatography/electrospray-tandem mass spectrometry. J Mass Spectrom 41:361–371. https://doi.org/10.1002/jms.996
Ma B-J, Liu J-K (2005) An unusual nitrogenous terphenyl derivative from fruiting bodies of the basidiomycete Sarcodon scabrosus. Z Naturforsch B Chem Sci 60:565–568
Ma B-J, Ruan Y (2008) Scabronine J, a new cyathane-type diterpenoid from the basidiomycete Sarcodon scabrosus. J Antibiot 61:86–88. https://doi.org/10.1038/ja.2008.115
Ma B-J, Zhu H-J, Liu J-K (2004) Isolation and characterization of new bitter diterpenoids from the basidiomycete Sarcodon scabrosus. Helv Chim Acta 87:2877–2881. https://doi.org/10.1002/hlca.200490259
Ma B-J, Shen J-W, Yu H-Y et al (2010) Hericenones and erinacines: stimulators of nerve growth factor (NGF) biosynthesis in Hericium erinaceus. Mycology 1:92–98. https://doi.org/10.1080/21501201003735556
Ma K, Bao L, Han J et al (2014a) New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum. Food Chem 143:239–245. https://doi.org/10.1016/j.foodchem.2013.07.124
Ma K, Han J, Bao L et al (2014b) Two sarcoviolins with antioxidative and α-glucosidase inhibitory activity from the edible mushroom Sarcodon leucopus collected in Tibet. J Nat Prod 77:942–947. https://doi.org/10.1021/np401026b
Ma K, Ren J, Han J et al (2014c) Ganoboninketals A-C, antiplasmodial 3,4-seco-27-norlanostane triterpenes from Ganoderma boninense Pat. J Nat Prod 77:1847–1852. https://doi.org/10.1021/np5002863
Malagòn O, Porta A, Clericuzio M et al (2014) Structures and biological significance of lactarane sesquiterpenes from the European mushroom Russula nobilis. Phytochemistry 107:126–134. https://doi.org/10.1016/j.phytochem.2014.08.018
Marcotullio MC (2011) Sarcodon mushrooms: biologically active metabolites. In: Rasooli I (ed) Phytochemicals – bioactivities and impact on health. InTech, Rijeka
Matsunaga S, Furuya-Suguri H, Nishiwaki S et al (1991) Differential effects of cryptoporic acids D and E, inhibitors of superoxide anion radical release, on tumor promotion of okadaic acid in mouse skin. Carcinogenesis 12:1129–1131. https://doi.org/10.1093/carcin/12.6.1129
McMorris TC, Anchel M (1965) Fungal metabolites. The structures of the novel sesquiterpenoids illudin-S and -M. J Am Chem Soc 87:1594–1600
McMorris TC, Staake MD, Kelner MJ (2004) Synthesis and biological activity of enantiomers of antitumor irofulven. J Org Chem 69:619–623. https://doi.org/10.1021/jo035084j
Mehta G, Pallavi K (2006) Total synthesis of the putative structure of the novel triquinane based sesquiterpenoid natural product dichomitol. Tetrahedron Lett 47:8355–8360. https://doi.org/10.1016/j.tetlet.2006.09.084
Melkonyan FS, Topolyan AP, Karchava AV, Yurovskaya MA (2008) Simple synthesis of methyl 1-(1,1-dimethyl-prop-2-en-1-yl)-1h-indole-3-carboxylate. Chem Heterocycl Compd 44:1288–1290. https://doi.org/10.1007/s10593-009-0183-0
Meng J, Li Y-Y, Ou Y-X et al (2011) New sesquiterpenes from Marasmius cladophyllus. Mycology 2:30–36. https://doi.org/10.1080/21501203.2011.554908
Mudalungu CM, Richter C, Wittstein K et al (2016) Laxitextines A and B, cyathane xylosides from the tropical fungus Laxitextum incrustatum. J Nat Prod 79:894–898. https://doi.org/10.1021/acs.jnatprod.5b00950
Nakada M (2014) Enantioselective total syntheses of cyathane diterpenoids. Chem Rec (New York, NY) 14:641–662. https://doi.org/10.1002/tcr.201402019
Narisawa T, Fukaura Y, Kotanagi H, Asakawa Y (1992) Inhibitory effect of cryptoporic acid E, a product from fungus Cryptoporus volvatus, on colon carcinogenesis induced with N-methyl-N-nitrosourea in rats and with 1,2-dimethylhydrazine in mice. Jpn J Cancer Res 83:830–834. https://doi.org/10.1111/j.1349-7006.1992.tb01987.x
Nishimura H, Tsuda S, Shimizu H et al (2008) De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Phytochemistry 69:2593–2602. https://doi.org/10.1016/j.phytochem.2008.07.014
Nishimura H, Murayama K, Watanabe T et al (2009) Absolute configuration of ceriporic acids, the iron redox-silencing metabolites produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Chem Phys Lipids 159:77–80. https://doi.org/10.1016/j.chemphyslip.2009.03.006
Nishimura H, Setogawa Y, Watanabe T et al (2011) Epoxy ceriporic acid produced by selective lignin-degrading fungus Ceriporiopsis subvermispora. Chem Phys Lipids 164:707–712. https://doi.org/10.1016/j.chemphyslip.2011.07.005
Nishimura H, Murayama K, Watanabe T et al (2012a) Diverse rare lipid-related metabolites including ω-7 and ω-9 alkenylitaconic acids (ceriporic acids) secreted by a selective white rot fungus, Ceriporiopsis subvermispora. Chem Phys Lipids 165:97–104. https://doi.org/10.1016/j.chemphyslip.2011.10.007
Nishimura H, Sasaki M, Seike H et al (2012b) Alkadienyl and alkenyl itaconic acids (ceriporic acids G and H) from the selective white-rot fungus Ceriporiopsis subvermispora: a new class of metabolites initiating ligninolytic lipid peroxidation. Org Biomol Chem 10:6432–6442. https://doi.org/10.1039/c2ob25415h
Nord C, Menkis A, Broberg A (2014a) Cytotoxic illudalane sesquiterpenes from the wood-decay fungus Granulobasidium vellereum (Ellis & Cragin) Jülich. Molecules 19:14195–14203. https://doi.org/10.3390/molecules190914195
Nord CL, Menkis A, Lendel C et al (2014b) Sesquiterpenes from the saprotrophic fungus Granulobasidium vellereum (Ellis & Cragin) Jülich. Phytochemistry 102:197–204. https://doi.org/10.1016/j.phytochem.2014.03.012
Nord C, Menkis A, Broberg A (2015) Cytotoxic illudane sesquiterpenes from the fungus Granulobasidium vellereum (Ellis and Cragin) Jülich. J Nat Prod 78:2559–2564. https://doi.org/10.1021/acs.jnatprod.5b00500
Norikura T, Fujiwara K, Narita T et al (2011) Anticancer activities of thelephantin O and vialinin A isolated from Thelephora aurantiotincta. J Agric Food Chem 59:6974–6979. https://doi.org/10.1021/jf200461j
Norikura T, Fujiwara K, Yanai T et al (2013) P-terphenyl derivatives from the mushroom Thelephora aurantiotincta suppress the proliferation of human hepatocellular carcinoma cells via iron chelation. J Agric Food Chem 61:1258–1264. https://doi.org/10.1021/jf3041098
Obara Y, Nakahata N, Kita T et al (1999) Stimulation of neurotrophic factor secretion from 1321N1 human astrocytoma cells by novel diterpenoids, scabronines A and G. Eur J Pharmacol 370:79–84. https://doi.org/10.1016/S0014-2999(99)00077-1
Obara Y, Kobayashi H, Ohta T et al (2001) Scabronine G-methylester enhances secretion of neurotrophic factors mediated by an activation of protein kinase C-ζ. Mol Pharmacol 59:1287–1297
Ohashi Y, Kan Y, Watanabe T et al (2007) Redox silencing of the Fenton reaction system by an alkylitaconic acid, ceriporic acid B produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Org Biomol Chem 5:840. https://doi.org/10.1039/b614379b
Ohta T, Kita T, Kobayashi N et al (1998) Scabronine A, a novel diterpenoid having potent inductive activity of the nerve growth factor synthesis, isolated from the mushroom, Sarcodon scabrosus. Tetrahedron Lett 39:6229–6232. https://doi.org/10.1016/S0040-4039(98)01282-9
Okada K, Ye YQ, Taniguchi K et al (2013) Vialinin A is a ubiquitin-specific peptidase inhibitor. Bioorg Med Chem Lett 23:4328–4331. https://doi.org/10.1016/j.bmcl.2013.05.093
Oliveira AG, Stevani CV (2009) The enzymatic nature of fungal bioluminescence. Photochem Photobiol Sci 8:1416–1421. https://doi.org/10.1039/b908982a
Onose J, Xie C, Ye YQ et al (2008) Vialinin A, a novel potent inhibitor of TNF-α production from RBL-2H3 cells. Biol Pharm Bull 31:831–833. https://doi.org/10.1248/bpb.31.831
Onose J, Yoshioka Y, Qi Y et al (2012) Inhibitory effects of vialinin A and its analog on tumor necrosis factor- a release and production from RBL-2H3 cells. Cell Immunol 279:140–144. https://doi.org/10.1016/j.cellimm.2012.10.008
Opatz T, Kolshorn H, Anke H (2008) Sterelactones: new isolactarane type sesquiterpenoids with antifungal activity from Stereum sp. IBWF 01060. J Antibiot (Tokyo) 61:563–567
Otto A, Porzel A, Schmidt J et al (2015) A study on the biosynthesis of hygrophorone B12 in the mushroom Hygrophorus abieticola reveals an unexpected labelling pattern in the cyclopentenone moiety. Phytochemistry 118:174–180. https://doi.org/10.1016/j.phytochem.2015.08.018
Otto A, Porzel A, Schmidt J et al (2016) Structure and absolute configuration of pseudohygrophorones A12 and B12, alkyl cyclohexenone derivatives from Hygrophorus abieticola (Basidiomycetes). J Nat Prod 79:74–80. https://doi.org/10.1021/acs.jnatprod.5b00675
Otto A, Porzel A, Westermann B et al (2017) Structural and stereochemical elucidation of new hygrophorones from Hygrophorus abieticola (Basidiomycetes). Tetrahedron 73:1682–1690. https://doi.org/10.1016/j.tet.2017.02.013
Paci A, Rezai K, Deroussent A et al (2006) Pharmacokinetics, metabolism, and routes of excretion of intravenous irofulven in patients with advanced solid tumors. Drug Metab Dispos 34:1918–1926. https://doi.org/10.1124/dmd.106.010512
Palermo JA, Rodríguez Brasco MF, Spagnuolo C, Seldes AM (2000) Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: The first natural nitrate esters. J Org Chem 65:4482–4486. https://doi.org/10.1021/jo991740x
Pei D, Xu J, Zhuang Q et al (2010) Secondary metabolites from higher fungi: discovery, bioactivity, and bioproduction. Adv Biochem Eng Biotechnol 123:127–141
Peters S, Spiteller P (2007a) Sanguinones A and B, blue pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena sanguinolenta. J Nat Prod 70:1274–1277. https://doi.org/10.1021/np070179s
Peters S, Spiteller P (2007b) Mycenarubins A and B, red pyrroloquinoline alkaloids from the mushroom Mycena rosea. Eur J Org Chem 2007(10):1571–1576. https://doi.org/10.1002/ejoc.200600826
Peters S, Jaeger RJR, Spiteller P (2008) Red pyrroloquinoline alkaloids from the mushroom Mycena haematopus. Eur J Org Chem 2008(2):319–323. https://doi.org/10.1002/ejoc.200700739
Pettit GR, Meng Y, Pettit RK et al (2010a) Antineoplastic agents 582. Part 1: Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae). Bioorg Med Chem 18:4879–4883. https://doi.org/10.1016/j.bmc.2010.06.023
Pettit GR, Meng Y, Pettit RK et al (2010b) Antineoplastic agents. 556. Isolation and structure of Coprinastatin 1 from Coprinus cinereus. J Nat Prod 73:388–392. https://doi.org/10.1021/np900371j
Pinedo C, Wang C-M, Pradier J-M et al (2008) Sesquiterpene synthase from the botrydial biosynthetic gene cluster of the phytopathogen Botrytis cinerea. ACS Chem Biol 3:791–801. https://doi.org/10.1021/cb800225v
Prateeptongkum S, Driller KM, Jackstell R, Beller M (2010) Iron-catalyzed carbonylation as a key step in the short and efficient syntheses of himanimide A and B. Chem Asian J 5:2173–2176. https://doi.org/10.1002/asia.201000384
Pulte A, Wagner S, Kogler H, Spiteller P (2016) Pelianthinarubins A and B, red pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena pelianthina. J Nat Prod 79:873–878. https://doi.org/10.1021/acs.jnatprod.5b00942
Purtov KV, Petushkov VN, Baranov MS et al (2015) The chemical basis of fungal bioluminescence. Angew Chem Int Ed 54:8124–8128. https://doi.org/10.1002/anie.201501779
Qin X, Shao H, Dong Z, Liu J (2008) Six new induced sesquiterpenes from the cultures of ascomycete Daldinia concentrica. J Antibiot (Tokyo) 61:556–562
Quang DN, Hashimoto T, Hitaka Y et al (2003a) Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry (Elsevier) 63:919–924. https://doi.org/10.1016/S0031-9422(03)00220-6
Quang DN, Hashimoto T, Nukada M et al (2003b) Thelephantins A, B and C: three benzoyl p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry 62:109–113
Quang DN, Hashimoto T, Hitaka Y et al (2004) Thelephantins I-N; p-terphenyl derivatives from the inedible mushroom Hydnellum caeruleum. Phytochemistry 65:1179–1184. https://doi.org/10.1016/j.phytochem.2004.02.018
Quin MB, Flynn CM, Wawrzyn GT et al (2013a) Mushroom hunting by using bioinformatics: application of a predictive framework facilitates the selective identification of sesquiterpene synthases in basidiomycota. Chembiochem 14:2480–2491. https://doi.org/10.1002/cbic.201300349
Quin MB, Wawrzyn G, Schmidt-Dannert C (2013b) Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius. Acta Crystallogr Sect F: Struct Biol Cryst Commun 69:574–577. https://doi.org/10.1107/S1744309113010749
Quin MB, Flynn CM, Schmidt-Dannert C (2014) Traversing the fungal terpenome. Nat Prod Rep 31:1449–1473. https://doi.org/10.1039/c4np00075g
Radulović N, Quang DN, Hashimoto T et al (2005) Terrestrins A-G: p-terphenyl derivatives from the inedible mushroom Thelephora terrestris. Phytochemistry 66(9):1052. https://doi.org/10.1016/j.phytochem.2005.03.008
Rahmawati N, Ohashi Y, Watanabe T et al (2005) Ceriporic acid B, an extracellular metabolite of Ceriporiopsis subvermispora, suppresses the depolymerization of cellulose by the fenton reaction. Biomacromolecules 6:2851–2856. https://doi.org/10.1021/bm050358t
Richter C, Helaly SE, Thongbai B et al (2016) Pyristriatins A and B: pyridino-cyathane antibiotics from the basidiomycete Cyathus cf. striatus. J Nat Prod 79:1684–1688. https://doi.org/10.1021/acs.jnatprod.6b00194
Rieger PH, Liermann JC, Opatz T et al (2010) Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae. J Antibiot 63:285–289. https://doi.org/10.1038/ja.2010.31
Ríos J-L, Andújar I, Recio M-C, Giner R-M (2012) Lanostanoids from fungi: a group of potential anticancer compounds. J Nat Prod 75(11):2016–2044. https://doi.org/10.1021/np300412h
Robbins WJ, Kavanagh F, Hervey A (1947) Antibiotic substances from basidiomycetes: I. Pleurotus griseus. Proc Natl Acad Sci USA 33:171–176. https://doi.org/10.1073/pnas.33.6.171
Sadorn K, Saepua S, Boonyuen N et al (2016) Antimicrobial activity and cytotoxicity of polyketides isolated from the mushroom Xerula sp. BCC56836. RSC Adv 6:94510–94523. https://doi.org/10.1039/C6RA21898A
Schmidt-Dannert C (2014) Biosynthesis of terpenoid natural products in fungi. In: Biotechnology of isoprenoids. Springer, pp 19–61
Schneider P, Bouhired S, Hoffmeister D (2008) Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides. Fungal Genet Biol 45:1487–1496. https://doi.org/10.1016/j.fgb.2008.08.009
Schüffler A, Anke T (2014) Fungal natural products in research and development. Nat Prod Rep 31(10):1425–1448. https://doi.org/10.1039/C4NP00060A
Schüffler A, Wollinsky B, Anke T et al (2012) Isolactarane and sterpurane sesquiterpenoids from the basidiomycete Phlebia uda. J Nat Prod 75:1405–1408. https://doi.org/10.1021/np3000552
Schultes R, Hofmann A (1980) Pflanzen der Götter. Hallwag, Bern
Schwenk D, Nett M, Dahse H et al (2014) Injury-induced biosynthesis of methyl-branched polyene pigments in a white-rotting basidiomycete. J Nat Prod 77(12):2658–2663
Schwenk D, Brandt P, Blanchette RA et al (2016) Unexpected metabolic versatility in a combined fungal fomannoxin/vibralactone biosynthesis. J Nat Prod 79:1407–1414. https://doi.org/10.1021/acs.jnatprod.6b00147
Selles P (2005) Synthesis and biological evaluation of himanimide C and unnatural analogues. Org Lett 7:605–608. https://doi.org/10.1021/ol047664o
Shi X-W, Li X-J, Gao J-M, Zhang X-C (2011a) Fasciculols H and I, two lanostane derivatives from Chinese mushroom Naematoloma fasciculare. Chem Biodivers 8:1864–1870. https://doi.org/10.1002/cbdv.201000203
Shi XW, Liu L, Gao JM, Zhang AL (2011b) Cyathane diterpenes from Chinese mushroom Sarcodon scabrosus and their neurite outgrowth-promoting activity. Eur J Med Chem 46:3112–3117. https://doi.org/10.1016/j.ejmech.2011.04.006
Shi X-W, Zhang A-L, Pescitelli G, Gao J-M (2012) Secoscabronine M, a novel diterpenoid from the Chinese bitter mushroom Sarcodon scabrosus. Chirality 24:386–390. https://doi.org/10.1002/chir.22031
Shibata H, Irie A, Morita Y (1998) New antibacterial diterpenoids from the Sarcodon scabrosus fungus. Biosci Biotechnol Biochem 62:2450–2452. https://doi.org/10.1271/bbb.62.2450
Stadler M, Hoffmeister D (2015) Fungal natural products-the mushroom perspective. Front Microbiol 6:1–4. https://doi.org/10.3389/fmicb.2015.00127
Stadler M, Sterner O (1998) Production of bioactive secondary metabolites in the fruit bodies of macrofungi as a response to injury. Phytochemistry 49:1013–1019. https://doi.org/10.1016/S0031-9422(97)00800-5
Stipkovits L, Ripley PH, Tenk M, Glávits R, Molnár T, Fodor L (2005) The efficacy of valnemulin (Econor) in the control of disease caused by experimental infection of calves with Mycoplasma bovis. Res Vet Sci 78(3):207–215
Sulake RS, Chen C (2015) Total synthesis of (+)-antroquinonol and (+)-antroquinonol D. Org Lett 17:1138–1141. https://doi.org/10.1021/acs.orglett.5b00046
Sulake RS, Lin H-H, Hsu C-Y et al (2015) Synthesis of (+)-antroquinonol: an antihyperglycemic agent. J Org Chem 80:6044–6051. https://doi.org/10.1021/acs.joc.5b00345
Sun R, Zheng X, Wang X et al (2011) Two new benzofuran derivatives from the fungus Stereum sp. YMF1.1684. Phytochem Lett 4:320–322. https://doi.org/10.1016/j.phytol.2011.06.003
Suresh M, Kumar N, Veeraraghavaiah G et al (2016) Total synthesis of coprinol. J Nat Prod 79(10):2740–2743. https://doi.org/10.1021/acs.jnatprod.6b00277
Suzuki S, Murayama T, Shiono Y (2005) Illudalane sesquiterpenoids, echinolactones A and B, from a mycelial culture of Echinodontium japonicum. Phytochemistry 66:2329–2333. https://doi.org/10.1016/j.phytochem.2005.06.018
Tanaka N, Kitamura A, Mizushina Y et al (1998) Fomitellic acids, triterpenoid inhibitors of eukaryotic DNA polymerases from a basidiomycete, Fomitella fraxinea. J Nat Prod 61:193–197. https://doi.org/10.1021/np970127a
Tang H-Y, Yin X, Zhang C-C et al (2015) Structure diversity, synthesis, and biological activity of cyathane diterpenoids in higher fungi. Curr Med Chem 22:2375–2391. https://doi.org/10.2174/0929867322666150521091333
Tao Q, Ma K, Yang Y et al (2016a) Bioactive sesquiterpenes from the edible mushroom Flammulina velutipes and their biosynthetic pathway confirmed by genome analysis and chemical evidence. J Org Chem 81:9867–9877. https://doi.org/10.1021/acs.joc.6b01971
Tao QQ, Ma K, Bao L et al (2016b) New sesquiterpenoids from the edible mushroom Pleurotus cystidiosus and their inhibitory activity against α-glucosidase and PTP1B. Fitoterapia 111:29–35. https://doi.org/10.1016/j.fitote.2016.04.007
Tao QQ, Ma K, Bao L et al (2016c) Sesquiterpenoids with PTP1B inhibitory activity and cytotoxicity from the edible mushroom Pleurotus citrinopileatus. Planta Med 82:639–644. https://doi.org/10.1055/s-0041-111629
Tateishi K, Hoshi H, Matsunaga K (2005) Inventors; Kureha Corporation, assignee. Antiallergic agent. WO2005095412 A1
Tian MQ, Liu R, Li JF et al (2016) Three new sesquiterpenes from the fungus Stereum sp. YMF1.1686. Phytochem Lett 15:186–189. https://doi.org/10.1016/j.phytol.2016.01.006
Tian M-Q, Wu Q-L, Wang X et al (2017) A new compound from Stereum insigne CGMCC5.57. Nat Prod Res 31:932–937. https://doi.org/10.1080/14786419.2016.1255889
Tzeng YM, Geethangili M (2011) Review of pharmacological effects of Antrodia camphorata and its bioactive compounds. Evid Based Complement Alternat Med. https://doi.org/10.1093/ecam/nep108
Villaume MT, Sella E, Saul G et al (2015) Antroquinonol A: scalable synthesis and preclinical biology of a phase 2 drug candidate. ACS Cent Sci 2(1):27–31. https://doi.org/10.1021/acscentsci.5b00345
Wackler B, Lackner G, Chooi YH, Hoffmeister D (2012) Characterization of the Suillus grevillei quinone synthetase GreA supports a nonribosomal code for aromatic α-keto acids. ChemBioChem 13(1798–1804):S1798/1–S1798/5. https://doi.org/10.1002/cbic.201200187
Wang G-Q, Wei K, Feng T et al (2012a) Vibralactones G-J from cultures of the basidiomycete Boreostereum vibrans. J Asian Nat Prod Res 14:115–120. https://doi.org/10.1080/10286020.2011.636037
Wang Y, Bao L, Yang X et al (2012b) Bioactive sesquiterpenoids from the solid culture of the edible mushroom Flammulina velutipes growing on cooked rice. Food Chem 132:1346–1353. https://doi.org/10.1016/j.foodchem.2011.11.117
Wang G-Q, Wei K, Li Z-H et al (2013a) Three new vibralactone-related compounds from cultures of Basidiomycete Boreostereum vibrans. J Asian Nat Prod Res 15:950–955. https://doi.org/10.1080/10286020.2013.824429
Wang S, Bao L, Han J et al (2013b) Pleurospiroketals A-E, perhydrobenzannulated 5,5-spiroketal sesquiterpenes from the edible mushroom Pleurotus cornucopiae. J Nat Prod 76:45–50. https://doi.org/10.1021/np3006524
Wang B, Han J, Xu W et al (2014a) Production of bioactive cyathane diterpenes by a birds nest fungus Cyathus gansuensis growing on cooked rice. Food Chem 152:169–176. https://doi.org/10.1016/j.foodchem.2013.11.137
Wang BT, Qi QY, Ma K et al (2014b) Depside α-glucosidase inhibitors from a culture of the mushroom Stereum hirsutum. Planta Med 80:918–924. https://doi.org/10.1055/s-0034-1382828
Wang S-C, Lee T-H, Hsu C-H et al (2014c) Antroquinonol D, isolated from Antrodia camphorata, with DNA demethylation and anticancer potential. J Agric Food Chem 62:5625–5635. https://doi.org/10.1021/jf4056924
Wang SM, Han JJ, Ma K et al (2014d) New alpha-glucosidase inhibitors with p-terphenyl skeleton from the mushroom Hydnellum concrescens. Fitoterapia 98:149–155. https://doi.org/10.1016/j.fitote.2014.07.019
Wang F, Ma H, Hu Z et al (2016a) Secondary metabolites from Colletotrichum capsici, an endophytic fungus derived from Siegesbeckia pubescens Makino. Nat Prod Res 31(16):1849–1854. https://doi.org/10.1080/14786419.2016.1261346
Wang J-C, Li G-Z, Lv N et al (2016b) Cryptoporic acid S, a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus. J Asian Nat Prod Res 6020:1–6. https://doi.org/10.1080/10286020.2016.1240170
Wangun HVK, Hertweck C (2007) Squarrosidine and Pinillidine: 3,3′-fused bis(styrylpyrones) from Pholiota squarrosa and Phellinus pini. Eur J Org Chem 2007(20):3292–3295. https://doi.org/10.1002/ejoc.200700090
Wawrzyn GT, Bloch SE, Schmidt-Dannert C (2012a) Discovery and characterization of terpenoid biosynthetic pathways of fungi, 1st edn. Elsevier, Amsterdam
Wawrzyn GT, Quin MB, Choudhary S et al (2012b) Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in basidiomycota. Chem Biol 19:772–783. https://doi.org/10.1016/j.chembiol.2012.05.012
Wilkins WH, Harris GCM (1943) Investigation into the production of bacteriostatic substances by fungi. Ann Appl Biol 30:226–229. https://doi.org/10.1111/j.1744-7348.1943.tb06193.x
Williams R (2013) Discontinued drugs in 2012: oncology drugs. Expert Opin Investig Drugs 22:1627–1644. https://doi.org/10.1517/13543784.2013.847088
Wittstein K, Rascher M, Rupcic Z et al (2016) Corallocins A-C, nerve growth and brain-derived neurotrophic factor inducing metabolites from the mushroom Hericium coralloides. J Nat Prod 79:2264–2269. https://doi.org/10.1021/acs.jnatprod.6b00371
Wu W, Zhao F, Bao L et al (2011a) Two new cryptoporic acid derivatives from the fruiting bodies of Cryptoporus sinensis. Helv Chim Acta 94:2020–2026. https://doi.org/10.1002/hlca.201100100
Wu W, Zhao F, Ding R et al (2011b) Four new cryptoporic acid derivatives from the fruiting bodies of Cryptoporus sinensis, and their inhibitory effects on nitric oxide production. Chem Biodivers 8:1529–1538. https://doi.org/10.1002/cbdv.201000184
Xia Q, Zhang H, Sun X et al (2014) A comprehensive review of the structure elucidation and biological activity of Triterpenoids from Ganoderma spp. Molecules 19:17478–17535. https://doi.org/10.3390/molecules191117478
Xiao H, Zhong JJ (2016) Production of useful terpenoids by higher-fungus cell factory and synthetic biology approaches. Trends Biotechnol 34:242–255. https://doi.org/10.1016/j.tibtech.2015.12.007
Xie C, Koshino H, Esumi Y et al (2005) Vialinin A, a novel 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenger from an edible mushroom in China. Biosci Biotechnol Biochem 69:2326–2332. https://doi.org/10.1271/bbb.69.2326
Xie C, Koshino H, Esumi Y et al (2008) Vialinins A and B: novel bioactive compounds from Thelephora vialis, an edible mushroom in China. ACS Symp Ser 993:465–472. https://doi.org/10.1021/bk-2008-0993.ch041
Xie HH, Xu XY, Dan Y, Wei XY (2011) Novel sesquiterpenes from the mycelial cultures of Dichomitus squalens. Helv Chim Acta 94:868–874. https://doi.org/10.1002/hlca.201000328
Xu Z, Yan S, Bi K et al (2013) Isolation and identification of a new anti-inflammatory cyathane diterpenoid from the medicinal fungus Cyathus hookeri Berk. Fitoterapia 86:159–162. https://doi.org/10.1016/j.fitote.2013.03.002
Yabuta T, Kobe K, Hayashi T (1934) Biochemical studies of the “bakanae” fungus of rice. I. Fusarinic acid, a new product of the “Bakanae” fungus. Z Pflanzenkrankh (Pflanzenpathol) Pflanzenschutz 10:1059–1068
Yamaoka M, Fukatsu Y, Nakazaki A, Kobayashi S (2009a) Synthetic study of fomitellic acids: construction of the AB ring moiety. Tetrahedron Lett 50:3849–3852. https://doi.org/10.1016/j.tetlet.2009.04.039
Yamaoka M, Nakazaki A, Kobayashi S (2009b) Total synthesis of fomitellic acid B. Tetrahedron Lett 50:6764–6768. https://doi.org/10.1016/j.tetlet.2009.09.088
Yang SS, Wang GJ, Wang SY et al (2009) New constituents with iNOS inhibitory activity from mycelium of Antrodia camphorata. Planta Med 75:512–516. https://doi.org/10.1055/s-0029-1185305
Yang SX, Yu ZC, Lu QQ et al (2012) Toxic lanostane triterpenes from the basidiomycete Ganoderma amboinense. Phytochem Lett 5:576–580. https://doi.org/10.1016/j.phytol.2012.05.017
Yang N, Ma Q, Huang S, Dai H (2014a) Two androstane derivatives from the cultures of fungus Marasmiellus ramealis (Bull.) Singer. Bull Kor Chem Soc 35:3224–3226
Yang X-Y, Li Z-H, Dong Z-J et al (2014b) Three new sesquiterpenoids from cultures of the basidiomycete Conocybe siliginea. J Asian Nat Prod Res 17:1–6. https://doi.org/10.1080/10286020.2014.939072
Yang N, Huang S, Dai H et al (2015) Chemical constituents from cultures of the fungus Marasmiellus ramealis (Bull.) Singer. J Braz Chem Soc 26:9–13. https://doi.org/10.5935/0103-5053.20140206
Yang L, Wang C, Zhou J, Kim S-W (2016) Combinatorial engineering of hybrid mevalonate pathways in Escherichia coli for protoilludene production. Microb Cell Factories 15:14. https://doi.org/10.1186/s12934-016-0409-7
Yaoita Y, Hiraob M, Kikuchi M, Machida K (2012) Three new lactarane sesquiterpenoids from the mushroom Russula sanguinea. Nat Prod Commun 7:1133–1135
Ye YQ, Koshino H, Onose J et al (2009) Structural revision of thelephantin G by total synthesis and the inhibitory activity against TNF-r production. J Org Chem 74(12):4642–4645. https://doi.org/10.1021/jo900638b
Ying YM, Shan WG, Zhang LW, Zhan ZJ (2013) Ceriponols A-K, tremulane sesquitepenes from Ceriporia lacerate HS-ZJUT-C13A, a fungal endophyte of Huperzia serrata. Phytochemistry 95:360–367. https://doi.org/10.1016/j.phytochem.2013.07.025
Yoshikawa K, Kaneko A, Matsumoto Y et al (2006) Russujaponols A-F illudoid sesquiterpenes from the fruiting body of Russula japonica. J Nat Prod 69:1267–1270. https://doi.org/10.1021/np068006a
Yoshikawa K, Matsumoto Y, Hama H et al (2009) Russujaponols G-L, illudoid sesquiterpenes, and their neurite outgrowth promoting activity from the fruit body of Russula japonica. Chem Pharm Bull 57:311–314
Yoshikawa K, Koso K, Shimomura M et al (2013) Yellow pigments, fomitellanols A and B, and drimane sesquiterpenoids, cryptoporic acids P and Q, from Fomitella fraxinea and their inhibitory activity against COX and 5-LO. Molecules 18:4181–4191. https://doi.org/10.3390/molecules18044181
Yoshioka Y, Namiki D, Makiuchi M et al (2016) Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-α production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity. Bioorg Med Chem Lett 26:4237–4240. https://doi.org/10.1016/j.bmcl.2016.07.051
Yun BS, Lee IK, Kim JP, Yoo ID (2000) Curtisians A-D, new free radical scavengers from the mushroom Paxillus curtisii. J Antibiot 53:114–122
Zähner H, Anke H, Anke T (1983) Evolution of secondary pathways. In: Bennett J, Ciegler A (eds) Secondary metabolites and differentiation in fungi. Dekker, New York, pp 153–171
Zeiler E, Braun N, Böttcher T et al (2011) Vibralactone as a tool to study the activity and structure of the ClpP1P2 complex from Listeria monocytogenes. Angew Chem Int Ed 50:11001–11004. https://doi.org/10.1002/anie.201104391
Zhao PJ, Yang YL, Du L et al (2013) Elucidating the biosynthetic pathway for vibralactone: a pancreatic lipase inhibitor with a fused bicyclic β-lactone. Angew Chem Int Ed 52:2298–2302. https://doi.org/10.1002/anie.201208182
Zheng Y, Shen Y (2009) Clavicorolides A and B, sesquiterpenoids from the fermentation products of edible fungus Clavicorona pyxidata. Org Lett 11:109–112. https://doi.org/10.1021/ol8024549
Zheng X, Li G-H, Xie M-J et al (2013) Stereumins K–P, sesquiterpenes from the fungus Stereum sp. CCTCC AF 2012007. Phytochemistry 86:144–150. https://doi.org/10.1016/j.phytochem.2012.10.014
Zheng Y, Wang J, Pang H (2014) Inventor. Sesquiterpene compounds with antitumor activity and preparation method of sesquiterpene compounds. Chinese patent CN104059040 A. 2014 Sep 24
Zheng Y, Pang H, Wang J et al (2015) New apoptosis-inducing sesquiterpenoids from the mycelial culture of Chinese edible fungus Pleurotus cystidiosus. J Agric Food Chem 63:545–551. https://doi.org/10.1021/jf504931n
Zhong J-J, Xiao J-H (2009) Secondary metabolites from higher fungi: discovery, bioactivity, and bioproduction. In: Biotechnology in China I. pp 79–150
Zhou Z-Y, Liu J-K (2010) Pigments of fungi (macromycetes). Nat Prod Rep 27:1531–1570. https://doi.org/10.1039/c004593d
Zhou Q, Snider BB (2008a) Synthesis of (±)-vibralactone. Org Lett 10:1401–1404. https://doi.org/10.1021/ol800118c
Zhou Q, Snider BB (2008b) Synthesis of (±)- and (−)-vibralactone and vibralactone C. J Org Chem 73:8049–8056. https://doi.org/10.1021/jo8015743
Zhou Z-Y, Tang J-G, Wang F et al (2008) Sesquiterpenes and aliphatic diketones from cultures of the basidiomycete Conocybe siliginea. J Nat Prod 71:1423–1426. https://doi.org/10.1021/np8002657
Zhou L-Y, Yu X-H, Lu B, Hua Y (2016) Bioassay-guided isolation of cytotoxic isocryptoporic acids from Cryptoporus volvatus. Molecules 21:1692. https://doi.org/10.3390/molecules21121692
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Schüffler, A. (2018). Secondary Metabolites of Basidiomycetes. In: Anke, T., Schüffler, A. (eds) Physiology and Genetics. The Mycota, vol 15. Springer, Cham. https://doi.org/10.1007/978-3-319-71740-1_8
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