Published September 30, 2020 | Version v1
Journal article Restricted

Chemical constituents and their cytotoxicities from mushroom Tricholoma imbricatum

  • 1. ∗ & ∗∗ & School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, Hubei, 430074, PR China

Description

Zhang, Fa-Lei, Yang, Hui-Xiang, Wu, Xing, Li, Jia-Yi, Wang, Shi-Qin, He, Juan, Li, Zheng-Hui, Feng, Tao, Liu, Ji-Kai (2020): Chemical constituents and their cytotoxicities from mushroom Tricholoma imbricatum. Phytochemistry (112431) 177: 1-9, DOI: 10.1016/j.phytochem.2020.112431, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112431

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFBCCE37B53EB245623FBD2BA0297879

Related works

References

  • Abraham, W.-R., Schmeda-Hirschmann, G., 1994. (24S)-3β -hydroxy-ergost-5-en-6-one from Cyttaria johowii. Phytochemistry 36, 459-461.
  • Adler, J.H., Young, M., Nes, W.R., 1977. Determination of the absolute configuration at C-20 and C-24 of ergosterol in ascomycetes and basidiomycetes by proton magnetic resonance spectroscopy. Lipids 12, 364-366.
  • Aiello, A., Ciminiello, P., Fattorusso, E., Magno, S., 1988. 3β, 5α -Dihydroxy-6β -methoxycholest-7-enes from the marine sponge Spongia agaricina. J. Nat. Prod. 51, 999-1002.
  • Bruhn, T., Schaumloffel, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249.
  • Burke, D.C., Turnbull, J.H., Wilson, W., 1953. Studies on the epoxides of 5α -hydroxy- and 5α -acetoxy-Δ7:9-steroids. J. Chem. Soc. 3237-3244.
  • Ceccherelli, P., Fringuelli, R., Federico Madruzza, G., Ribaldi, M., 1975. Cerevisterol and ergosterol peroxide from Acremonium luzulae. Phytochemistry 14, 1434.
  • Chen, M., Wang, K.-L., Liu, M., She, Z.-G., Wang, C.-Y., 2015. Bioactive steroid derivatives and butyrolactone derivatives from a gorgonian-derived Aspergillus sp. fungus. Chem. Biodivers. 12, 1398-1406.
  • Chobot, V., Opletal, L., Jahodar, L., Patel, A.V., Dacke, C.G., Blunden, G., 1997. Ergosta- 4,6,8,22-tetraen-3-one from the edible fungus, Pleurotus ostreatus (oyster fungus).
  • Phytochemistry 45, 1669-1671.
  • Choi, J.-H., Ogawa, A., Abe, N., Masuda, K., Koyama, T., Yazawa, K., Kawagishi, H., 2009. Chaxines B, C, D, and E from the edible mushroom Agrocybe chaxingu. Tetrahedron 65, 9850-9853.
  • De Riccardis, F., Spinella, A., Izzo, I., Giordano, A., Sodano, G., 1995. Synthesis of (17R)- 17-methylincisterol, a highly degraded marine steroid. Tetrahedron Lett. 36, 4303-4306.
  • Deng, H., Yao, Y.J., Pegler, D.N., 2004. An annotated checklist of Tricholoma from China. Journal of Fungal Research 2, 1-18.
  • Elks, J., Evans, R.M., Long, A.G., Thomas, G.H., 1954. Studies in the synthesis of cortisone. Part IV. The oxidation of steroid 7 : 9-dienes with sodium dichromate in acetic acid. J. Chem. Soc. 451-462.
  • Feng, T., He, J., Ai, H.-L., Huang, R., Li, Z.-H., Liu, J.-K., 2015. Three new triterpenoids from European mushroom Tricholoma terreum. Nat. Prod. Bioprospect. 5, 205-208.
  • Feng, T., Gan, X.-Q., Zhao, Y.-L., Zhang, S.-B., Chen, H.-P., He, J., Zheng, Y.-S., Sun, H., Huang, R., Li, Z.-H., Liu, J.-K., 2019. Tricholopardins A and B, anti-inflammatory terpenoids from the fruiting bodies of Tricholoma pardinum. J. Nat. Prod. 82, 45-50.
  • Frichert, A., Jones, P.G., Lindel, T., 2016. Enantioselective total synthesis of terreumols A and C from the mushroom Tricholoma terreum. Angew. Chem. Int. Ed. 55, 2916-2919.
  • Frisch, M.J., G.W.T.,Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian, Inc., Wallingford CT Gaussian 16, Revision B.01.
  • Greca, M.D., Fiorentino, A., Molinaro, A., Monaco, P., Previtera, L., 1993. Steroidal 5,6- epoxides from Arum italicum. Nat. Prod. Lett. 2, 27-32.
  • Hirata, Y., Nakazaki, A., Kawagishi, H., Nishikawa, T., 2017. Biomimetic synthesis and structural revision of chaxine B and its analogues. Org. Lett. 19, 560-563.
  • Ishizuka, T., Yaoita, Y., Kikuchi, M., 1997. Sterol constituents from the fruit bodies of Grifola frondosa (FR.) S. F. GRAY. Chem. Pharm. Bull. 45, 1756-1760.
  • Jinming, G., Lin, H., Jikai, L., 2001. A novel sterol from Chinese truffles Tuber indicum. Steroids 66, 771-775.
  • Kawagishi, H., Katsumi, R., Sazawa, T., Mizuno, T., Hagiwara, T., Nakamura, T., 1988. Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry 27, 2777-2779.
  • Kobata, K., Wada, T., Hayashi, Y., Shibata, H., 1994. Volemolide, a novel norsterol from the fungus Lactarius volemus. Biosci. Biotechnol. Biochem. 58, 1542-1544.
  • Li, G., Kusari, S., Kusari, P., Kayser, O., Spiteller, M., 2015. Endophytic Diaporthe sp. LG23 produces a potent antibacterial tetracyclic triterpenoid. J. Nat. Prod. 78, 2128-2132.
  • Liu, X.-H., Miao, F.-P., Liang, X.-R., Ji, N.-Y., 2014. Ergosteroid derivatives from an algicolous strain of Aspergillus ustus. Nat. Prod. Res. 28, 1182-1186.
  • Luo, X., Li, F., Shinde, P.B., Hong, J., Lee, C.-O., Im, K.S., Jung, J.H., 2006. 26,27- Cyclosterols and other polyoxygenated sterols from a marine sponge Topsentia sp. J. Nat. Prod. 69, 1760-1768.
  • 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.
  • McCloskey, S., Noppawan, S., Mongkolthanaruk, W., Suwannasai, N., Senawong, T., Prawat, U., 2017. A new cerebroside and the cytotoxic constituents isolated from Xylaria allantoidea SWUF76. Nat. Prod. Res. 31, 1422-1430.
  • Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63.
  • Nakada, T., Yamamura, S., 2000. Three new metabolites of hybrid strain KO 0231, derived from Penicillium citreo-viride IFO 6200 and 4692. Tetrahedron 56, 2595-2602.
  • Notaro, G., Piccialli, V., Sica, D., 1992. New steroidal hydroxyketones and closely related diols from the marine sponge Cliona copiosa. J. Nat. Prod. 55, 1588-1594.
  • Nozoe, S., Takahashi, A., Kusano, G., Itai, A., Iitaka, Y., 1982. Tricholidic acid, a new triterpene lactonic acid from Tricholoma species. Chem. Lett. 11, 1679-1680.
  • Ohnuma, N., Amemiya, K., Kakuda, R., Yaoita, Y., Machida, K., Kikuchi, M., 2000. Sterol constituents from two edible mushrooms, Lentinula edodes and Tricholoma matsutake. Chem. Pharm. Bull. 48, 749-751.
  • Parsons, S., Flack, H.D., Wagner, T., 2013. Use of intensity quotients and differences in absolute structure refinement. Acta Crystallogr. B69, 249-259.
  • Reed, L.J., Muench, H., 1938. A simple method of estimating fifty percent endpoints. Am. J. Hyg. 27, 493-497.
  • Sright, J.L.C., McInnes, A.G., Shimizu, S., Smith, D.G., Walter, J.A., Idler, D., Khalil, W., 1978. Identification of C-24 alkyl epimers of marine sterols by 13C nuclear magnetic resonance spectroscopy. Can. J. Chem. 56, 1898-1903.
  • Stephens, P.J., Devlin, F.J., Cheeseman, J.R., Frisch, M.J., 2001. Calculation of optical rotation using density functional theory. J. Phys. Chem. 105, 5356-5371.
  • Togashi, H., Mizushina, Y., Takemura, M., Sugawara, F., Koshino, H., Esumi, Y., Uzawa, J., Kumagai, H., Matsukage, A., Yoshida, S., Sakaguchi, K., 1998. 4-Hydroxy-17- methylincisterol, an inhibitor of DNA polymerase-alpha activity and the growth of human cancer cells in vitro. Biochem. Pharmacol. 56, 583-590.
  • Wang, F., Fang, Y., Zhang, M., Lin, A., Zhu, T., Gu, Q., Zhu, W., 2008. Six new ergosterols from the marine-derived fungus Rhizopus sp. Steroids 73, 19-26.
  • Wangun, H.V.K., Albrecht, B., Waltraud, H., Nkengfack, A.E., Christian, H., 2005. Anti-inflammatory and anti-hyaluronate lyase activities of lanostanoids from Piptoporus betulinus. J. Antibiot. 36, 755.
  • Yaoita, Y., Endo, M., Tani, Y., Machida, K., Amemiya, K., Furumura, K., Kikuchi, M., 1999. Sterol constituents from seven mushrooms. Chem. Pharm. Bull. 47, 847-851.
  • Yin, X., Feng, T., Li, Z.-H., Dong, Z.-J., Li, Y., Liu, J.K., 2013. Highly oxygenated meroterpenoids from fruiting bodies of the mushroom Tricholoma terreum. J. Nat. Prod. 76, 1365-1368.
  • Yin, X., Feng, T., Shang, J.-H., Zhao, Y.-L., Wang, F., Li, Z.-H., Dong, Z.-J., Luo, X.-D., Liu, J.-K., 2014. Chemical and toxicological investigations of a previously unknown poisonous European mushroom Tricholoma terreum. Chem. Eur J. 20, 7001-7009.
  • Yue, J.-M., Chen, S.-N., Lin, Z.-W., Sun, H.-D., 2001. Sterols from the fungus Lactarium volemus. Phytochemistry 56, 801-806.
  • Zhao, Z.-Z., Chen, H.-P., Wu, B., Zhang, L., Li, Z.-H., Feng, T., Liu, J.-K., 2017. Matsutakone and matsutoic acid, two (nor)steroids with unusual skeletons from the edible mushroom Tricholoma matsutake. J. Org. Chem. 82, 7974-7979.
  • Zhao, Z.-Z., Han, K.-Y., Li, Z.-H., Feng, T., Chen, H.-P., Liu, J.-K., 2019. Cytotoxic ergosteroids from the fungus Stereum hirsutum. Phytochemistry Letters 30, 143-149.