Abstract
A new cytotoxic lanostane triterpenoid, 24(E)-3β-hydroxylanosta-8,24-dien-26-al-21-oic acid (1), was isolated from the fruiting bodies of the mushroom Hebeloma versipelle. The structure was elucidated on the basis of spectroscopic studies including 2D NMR experiments. Compound 1 moderately inhibited the growth of several tumor cell lines (IC50 10∼25.0 µg/ml).
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De Bernardi M, Fronza G, Gianotti MP, Mellerio G, Vidari G, Vita-Finzi P . Fungal metabolites XIII: New cytotoxic triterpene from Hebeloma species (Basidiomycetes). Tetrahedron Lett 24: 1635–1638 ( 1983)
Fujimoto H, Takano Y, Yamazaki M . Isolation, identification and pharmacological studies on three toxic metabolites from a mushroom, Hebeloma spoliatum. Chem Pharm Bull 40: 869–872 ( 1992)
Bocchi M, Garlaschelli L, Vidari G, Mellerio G . New farnesane fesquiterpenes from Hebeloma senescens. J Nat Prod 55: 428–431 ( 1992)
Garlaschelli L, Vidari G, Virtuani M, Vita-Finzi P, Mellerio G . The structures of new lanostane triterpenes from the fruiting bodies of Hebeloma senescens. J Nat Prod 58: 992–1002 ( 1995)
Fujimoto H, Suzuki K, Hagiwara H, Yamazaki M . New toxic metabolites from a mushroom, Hebeloma vinosophyllum. I. structures of hebevinosides I, II, III, IV, and V. Chem Pharm Bull 34: 88–99 ( 1986)
Fujimoto H, Hagiwara H, Suzuki K, Yamazaki M . New toxic metabolites from a mushroom, Hebeloma vinosophyllum. II. isolation and structures of hebevinosides VI, VII, VIII, IX, X, and XI. Chem Pharm Bull 35: 2254–2260 ( 1987)
Fujimoto H, Maeda K, Yamazaki M . New toxic metabolites from a mushroom, Hebeloma vinosophyllum. III. isolation and structures of three new glycosides, hebevinosides XII, XIII, and XIV, and productivity of the hebevinosides at three growth stages of the mushroom. Chem Pharm Bull 39: 1958–1961 ( 1991)
Wichlacz M, Ayer WA, Trifonov LS, Chakravarty P, Khasa D . Cis-fused caryophyllenes from liquid cultures of Hebeloma longicaudum. Phytochemistry 51: 873–877 ( 1999)
Wichlacz M, Ayer WA, Trifonov LS, Chakravarty P, Khasa D . A caryophyllene-related sesquiterpene and two 6,7-seco-caryophyllenes from liquid cultures of Hebeloma longicaudum. J Nat Prod 62: 484–486 ( 1999)
Wichlacz M, Ayer WA, Trifonov LS, Chakravarty P, Khasa D . Two 6,7-seco-caryophyllenes and an alloaromadendrane from liquid cultures of Hebeloma longicaudum. Phytochemistry 52: 1421–1425 ( 1999)
Liu JK . N-containing compounds of macromycetes. Chem Rev 105: 2723–2744 ( 2005)
Liu JK . Biologically active substances from mushrooms in Yunnan, China. Heterocycles 57: 157–167 ( 2002)
Ding ZH, Dong ZJ, Liu JK . Albaconol, a novel prenylated resorcinol from basidiomycetes Albatrellus confluens. Helv Chim Acta 84: 259–262 ( 2001)
Hellwig V, Nopper R, Mauler F, Freitag J, Liu JK, Ding ZH, Stadler M . Activities of prenylphenol derivatives from fruitbodies of Albatrellus spp. on the human and rat vanilloid receptor 1 (VR1) and characterisation of the novel natural product, confluentin. Arch Pharm Pharm Med Chem 2: 119–126 ( 2003)
Qing C, Liu MH, Yang WM, Zhang YL, Wang L, Liu JK . Effects of albaconol from the basidiomycete Albatrellus confluens on DNA topoisomerase II-mediated DNA cleavage and relaxation. Planta Med 70: 792–796 ( 2004)
Wang F, Luo DQ, Liu JK . Aurovertin E, A new polyene pyrone from the basidiomycete Albatrellus confluens. J Antibiot 58: 412–415 ( 2005)
Keller AC, Maillard MP, Hostettmann K . Antimicrobial steroids from the fungus Fomitopsis pinicola. Phytochemistry 41: 1041–1046 ( 1996)
Vieira LMM, Kijjoa A, Silva AMS, Mondranondra IO, Kengthong S, Gales L, Damas AM, Herz W . Lanostanes and friedolanostanes from the bark of Garcinia speciosa. Phytochemistry 65: 393–398 ( 2004)
Mosmman T . Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 65: 55–63 ( 1983)
Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL . Feasibility of drug screenig with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 48: 589–601 ( 1988)
Zhou JJ, Yue XF, Han JX, Yang WY . Improved MTT assay for activity of antitumor agents. Chin J Pharm 24: 455–457 ( 1993)
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Shao, HJ., Qing, C., Wang, F. et al. A New Cytotoxic Lanostane Triterpenoid from the Basidiomycete Hebeloma versipelle. J Antibiot 58, 828–831 (2005). https://doi.org/10.1038/ja.2005.111
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DOI: https://doi.org/10.1038/ja.2005.111
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