Fomentarols A-D, sterols from the polypore macrofungus Fomes fomentarius

Phytochemistry

Volumn 92, Issue , 2013, Pages 137-145

  Zang, Yi ^a,b   Xiong, Juan ^a   Zhai, Wen Zhu ^a,b   Cao, Lei ^b   Zhang, Sheng Ping ^b   Tang, Yu ^a   Wang, Ji ^a,b   Su, Jing Jing ^a,b   Yang, Guo Xun ^a   Zhao, Yun ^b   Fan, Hui ^b   Xia, Gang ^b   Wang, Chuan Gui ^b   Hu, Jin Feng ^a,b  

^a FUDAN UNIVERSITY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Cytotoxicities; Fomentarols; Fomes fomentarius; Polyhydroxylated sterols; Polyporaceae

Indexed keywords

FOMES FOMENTARIUS; POLYPORACEAE;

EID: 84884903022     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.05.003     Document Type: Article

References (44)

1. Ahmed, A.F., Dai, C.-F., Kuo, Y.-H., Sheu, J.-H., 2003. 1a,3b,5b-Trihydroxy-24- methylenecholestan-6-one: a novel steroid from a soft coral Sinularia gibberosa. Steroids 68, 377-381. (Pubitemid 36638250)
2. Ahmed, A.F., Hsieh, Y.-T., Wen, Z.-H., Wu, Y.-C., Sheu, J.-H., 2006. Polyoxygenated sterols from the Formosan soft coral Sinularia gibberosa. J. Nat. Prod. 69, 1275-1279. (Pubitemid 44568233)
3. Aiello, A., Ciminiello, P., Fattorusso, E., Magno, S., 1988. 3b,5a-Dihydroxy-6bmethoxycholest- 7-enes from the marine sponge Spongia agaricina. J. Nat. Prod. 51, 999-1002.
4. Aoki, M., Tan, M., Fukushima, A., Hieda, T., Kubo, S., Takabayashi, M., Ono, K., Mikami, Y., 1993. Antiviral substances with systemic effects produced by Basidiomycetes such as Fomes fomentarius. Biosci. Biotechnol. Biochem. 57, 278-282.
5. Bruggisser, R., von Daeniken, K., Jundt, G., Schaffner, W., Tullberg-Reinert, H., 2002. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay. Planta Med. 68, 445-448. (Pubitemid 34606689)
6. Chen, W., Zhao, Z., Li, Y.Q., 2011. Simultaneous increase of mycelial biomass and intracellular polysaccharide from Fomes fomentarius and its biological function of gastric cancer intervention. Carbohydr. Polym. 85, 369-375.
7. Cui, C.-M., Li, X.-M., Meng, L., Li, C.-S., Huang, C.-G., Wang, B.-G., 2010. 7-Norergosterolide, a pentalactone-containing norsteroid and related steroids from the marine-derived endophytic Aspergillus ochraceus EN-31. J. Nat. Prod. 73, 1780-1784.
8. Colombain, M., Goll, V., Muyard, F., Girard, C., Bévalot, F., Richert, L., 2001. A bioassay using the human hepatoblastoma cell line HepG2 for detecting phototoxicity of furocoumarins. Planta Med. 67, 644-646. (Pubitemid 32929576)
9. Demarco, P.V., Farkas, E., Doddrell, D., Mylari, B.L., Wenkert, E., 1968. Pyridineinduced solvent shifts in the nuclear magnetic resonance spectra of hydroxylic compounds. J. Am. Chem. Soc. 90, 5480-5486.
10. Dewick, P.M., 2009. Medicinal Natural Products: A Biosynthetic Approach. John Wiley & Sons, Ltd., UK, pp. 256.
11. Feng, W., Yang, J.-S., 2010. Studies on chemical constituents of Fomes fomentarius (L. Ex. Fr.). Chin. Pharm. J. 45, 1528-1530.
12. Gao, J.M., Hu, L., Liu, J.K., 2001. A novel sterol from Chinese truffles Tuber indicum. Steroids 66, 771-775.
13. Gunatilaka, A.A.L., Gopichand, Y., Schmitz, F.J., Djerassi, C., 1981. Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5a,8a-epidioxy sterols from four marine organisms. J. Org. Chem. 46, 3860-3866.
14. Holland, I.P., McCluskey, A., Sakoff, J.A., Gilbert, J., Chau, N., Robinson, P.J., Motti, C.A., Wright, A.D., van Altena, I.A., 2009. Steroids from an Australian sponge Psammoclema sp. J. Nat. Prod. 72, 102-106.
15. Hu, J.-F., Kelly, M., Hamann, M.T., 2002. 26-Nor-25-isopropyl-ergosta-5, 7,22E-trien- 3b-ol: a new C29 sterol from the sponge Agelas sceptrum from Jamaica. Steroids 67, 743-747. (Pubitemid 34765662)
16. Ishizuka, T., Yaoita, Y., Kikuchi, M., 1997. Sterol constituents from the fruit bodies of Grifola frondosa (Fr.) S. F. Gary. Chem. Pharm. Bull. 45, 1756-1760. (Pubitemid 28550456)
17. Judova, J., Dubikova, K., Gaperova, S., Gaper, J., Pristas, P., 2012. The occurrence and rapid discrimination of Fomes fomentarius genotypes by ITS-RELP analysis. Fungal Biol. 116, 155-160.
18. Kawagishi, H., Katsumi, R., Sazawa, T., Mizuno, T., Hagiwara, T., Nakamura, T., 1988. Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry 27, 2777-2779.
19. Li, X.-W., Guo, Z.-T., Zhao, Y., Zhao, Z., Hu, J.-F., 2010. Chemical constituents from Saussurea cordifolia. Phytochemistry 71, 682-687.
20. Li, X.-W., Weng, L., Gao, X., Zhao, Y., Pang, F., Liu, J.-H., Zhang, H.-F., Hu, J.-F., 2011. Antiproliferative and apoptotic sesquiterpene lactones from Carpesium faberi. Bioorg. Med. Chem. Lett. 21, 366-372.
21. Madaio, A., Piccialli, V., Sica, D., Corriero, G., 1989. New polyhydroxysterols from the Dictyoceratid sponges Hippospongia communis, Spongia officinalis, Ircinia variabilis, and Spongionella gracilis. J. Nat. Prod. 52, 952-961.
22. Matthewman, W.G., Pielou, D.P., 1971. Arthropods inhabiting the sporophores of Fomes fomentarius (Polyporaceae) in Gatineau Park. Quebec. Can. Entomol. 103, 775-847.
23. Migliuolo, A., Notaro, G., Piccialli, V., Sica, D., 1990. New tetrahydroxylated sterols from the marine sponge Spongia officinalis. J. Nat. Prod. 53, 1414-1424.
24. Mansoor, T.A., Hong, J., Lee, C.-O., Bae, S.-J., Im, K.S., Jung, J.H., 2005. Cytotoxic sterol derivatives from a marine sponge Homaxinella sp. J. Nat. Prod. 68, 331-336. (Pubitemid 40545466)
25. Munro, H.D., Musgrave, O.C., 1971. Extractives from sporophores of some Fomes species. J. Chem. Soc. C, 685-688.
26. Odinokov, V.N., Afon'kina, S.R., Shafikov, R.V., Savchenko, R.G., Galyautdinov, I.V., Khalilov, L.M., Shashkov, A.S., 2007. 7,8-Dihydro analogs of ecdysteroids. Russ. J. Org. Chem. 43, 825-833.
27. Park, Y.-M., Kim, I.-T., Park, H.-J., Choi, J.-W., Park, K.-Y., Lee, J.-D., Nam, B.-H., Kim, D.-G., Lee, J.-Y., Lee, K.-T., 2004. Anti-inflammatory and anti-nociceptive effects of the methanol extract of Fomes fomentarius. Biol. Pharm. Bull. 27, 1588-1593. (Pubitemid 41701645)
28. Rösecke, J., König, W.A., 2000. Constituents of various wood-rotting basidiomycetes. Phytochemistry 54, 603-610. (Pubitemid 30625836)
29. Roussel, B., Rapior, S., Masson, C.L., Boutie, P., 2002. Fomes fomrntarius (L. Fr.) Fr.: a mushroom with varied uses. Cryptogamie Mycol. 23, 349-366. (Pubitemid 36224801)
30. Scherrer, H., 1969. Über einige Eigenschaften von 6-Keto-D7-steroiden. Helv. Chim. Acta 52, 2428-2436.
31. Seniuk, O.F., Gorovoj, L.F., Beketova, G.V., Savichuk, H.O., Rytik, P.G., Kucherov, I.I., Prilutskay, A.B., Prilutsky, A.I., 2011. Anti-infective properties of the melanin- glucan complex obtained from medicinal tinder bracket mushroom, Fomes fomentarius (L. Fr.) Fr. (Aphyllophoromycetideae). Int. J. Med. Mushrooms 13, 7-18.
32. Smith, W.B., Newsoroff, G.P., 1973. The synthesis of 23,24-14C-ecdysone. Steroids 22, 819-828.
33. Takaishi, Y., Uda, M., Ohashi, T., Nakano, K., Murakami, K., Tomimatsu, T., 1991. Glycosides of ergosterol derivatives from Hericum erinacens. Phytochemistry 30, 4117-4120.
34. Voigt, B., Schmidt, J., Adam, G., 1985. Ergosterolperoxid aus dem Pilz Pisolithus tinctorius. Z. Chem. 25, 405-406.
35. Wang, Y., Wang, S.J., Mo, S.Y., Li, S., Yang, Y.C., Shi, J.G., 2006. An abietane diterpene and a sterol from fungus Phellinus igniarius. Chin. Chem. Lett. 17, 481-484. (Pubitemid 43652236)
36. Wright, J.L.C., McInnes, A.G., Shimizu, S., Smith, D.G., Walter, J.A., 1978. Identificaiton of C-24 alkyl epimers of marine sterols by 13C nuclear magnetic resonance spectroscopy. Can. J. Chem. 56, 1898-1903.
37. Wu, S.B., Bao, Q.Y., Wang, W.X., Zhao, Y., Xia, G., Zhao, Z., Zeng, H.Q., Hu, J.-F., 2011. Cytotoxic triterpenoids and steroids from the bark of Melia azedarach. Planta Med. 77, 922-928.
38. Wu, S.B., Ji, Y.P., Zhu, J.J., Zhao, Y., Xia, G., Hu, Y.H., Hu, J.-F., 2009. Steroids from the leaves of Chinese Melia azedarach and their cytotoxic effects on human cancer cell lines. Steroids 74, 761-765.
39. Wu, S.B., Su, J.J., Sun, L.H., Wang, W.X., Zhao, Y., Li, H., Zhang, S.P., Dai, G.H., Wang, C.G., Hu, J.-F., 2010. Triterpenoids and steroids from the fruits of Melia toosendan and their cytotoxic effects on two human cancer cell lines. J. Nat. Prod. 73, 1898-1906.
40. Yan, X.H., Liu, H.L., Huang, H., Li, X.B., Guo, Y.-W., 2011. Steroids with aromatic Arings from the Hainan soft coral Dendronephthya studeri Ridley. J. Nat. Prod. 74, 175-180.
41. Yang, S.-P., Xu, J., Yue, J.-M., 2003. Sterols from the fungus Catathelasma imperiale. Chin. J. Chem. 21, 1390-1394.
42. You, M., Xiong, J., Zhao, Y., Cao, L., Wu, S.B., Xia, G., Hu, J.-F., 2011. Glycosides from the methanol extract of Notopterygium incisum. Planta Med. 77, 1939-1943.
43. Yue, J.-M., Chen, S.-N., Lin, Z.-W., Sun, H.-D., 2001. Sterols from the fungus Lactarium volemus. Phytochemistry 56, 801-806. (Pubitemid 32288987)
44. Zhang, Z., Zhang, W., Ji, Y.P., Zhao, Y., Wang, C.G., Hu, J.-F., 2010. Gynostemosides A- E, megastigmane glycosides from Gynostemma pentaphyllum. Phytochemistry 71, 693-700.