2005
DOI: 10.1038/ja.2005.111
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A New Cytotoxic Lanostane Triterpenoid from the Basidiomycete Hebeloma versipelle

Abstract: A new cytotoxic lanostane triterpenoid, 24(E)-3b -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 (IC 50 10ϳ25.0 mg/ml).

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Cited by 18 publications
(6 citation statements)
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“…While triterpenes are considered potential anticancer agents (Su et al, 2000;Gonzalez et al, 2002;Lin et al, 2003;Zhou et al, 2008;Cheng et al, 2010), compound 2's weak inhibition of hepatocellular carcinoma growth may indicate lack of anticancer properties. An insignificant cytotoxicity of some lanostane triterpenoids against tumour cell lines has also previously been reported (Kima et al, 2004;Shao et al, 2005). The cytotoxicity level of the isolated compound encourages the development of this compound into a pharmacological anti-platelet aggregation drug.…”
Section: Wellmentioning
confidence: 61%
“…While triterpenes are considered potential anticancer agents (Su et al, 2000;Gonzalez et al, 2002;Lin et al, 2003;Zhou et al, 2008;Cheng et al, 2010), compound 2's weak inhibition of hepatocellular carcinoma growth may indicate lack of anticancer properties. An insignificant cytotoxicity of some lanostane triterpenoids against tumour cell lines has also previously been reported (Kima et al, 2004;Shao et al, 2005). The cytotoxicity level of the isolated compound encourages the development of this compound into a pharmacological anti-platelet aggregation drug.…”
Section: Wellmentioning
confidence: 61%
“…The anti-inflammatory data revealed multiple anti-inflammatory bioactivities in active components which were purified from the fruiting bodies of T. cubensis and T. suaveolens . In previous reports, 5 showed growth inhibition on several tumor cell lines (IC 50 10–25 μg/mL) [ 32 ]. Compound 14 was reported to attenuate the growth and triggered an apoptotic process in prostate cancer cells [ 55 ].…”
Section: Resultsmentioning
confidence: 97%
“…In T. cubensis , two new triterpenoids ( 1 – 2 ) ( Figure 2 ) were characterized and their chemical structures were constructed with the assistance of the NMR spectral elucidation and MS spectrometric analysis. Moreover, fourteen known compounds, including eight triterpenoids, hexagonin F ( 3 ) [ 30 ], sinensoic acid ( 4 ) [ 31 ], 24( E )-3 β -hydroxylanosta-8,24-dien-26-al-21-oic acid ( 5 ) [ 32 ], trametenolic acid ( 6 ) [ 33 ], eburicoic acid ( 7 ) [ 34 ], 24-methylenelanost-8-en-3-ol ( 8 ) [ 35 ], eburicodiol ( 9 ) [ 36 ], and gloeophyllin B ( 10 ) [ 37 ]; four steroids, ergosterol peroxide ( 11 ) [ 38 ], ergosterol ( 12 ) [ 39 ], (22 E )-ergosta-7,22-dien-3 β -ol ( 13 ) [ 40 ], and (22 E ,24 R )-5-hydroxy-5 α -ergosta-7,22-diene-3,6-dione ( 14 ) [ 41 ]; and two isocoumarins, oospoglycol ( 15 ) [ 42 ] and oospolactone ( 16 ) [ 43 ], were identified. In addition, eleven known constituents, including one triterpenoid, lupeol ( 17 ) [ 44 ]; seven steroids, ergosterol peroxide ( 11 ), (22 E )-ergosta-7,22-dien-3 β -ol ( 13 ), (22 E ,24 R )-5-hydroxy-5 α -ergosta-7,22-diene-3,6-dione ( 14 ), 9,11-dehydroergosterol peroxide ( 18 ) [ 45 ], 5,8-epidioxy-(5 α ,8 α ,22 E )-ergosta-6,22-dien-3-one ( 19 ) [ 46 ], ergosta-7,22-diene-3-one ( 20 ) [ 40 ], and stigmast-4-en-3-one ( 21 ) [ 47 ]; and three benzenoids, syringic acid ( 22 ) [ 48 ], isovanillic acid ( 23 ) [ 49 ], and tyrosol ( 24 ) [ 50 ], were characterized from the fruiting bodies of T. suaveolens .…”
Section: Resultsmentioning
confidence: 99%
“…1.11) [44]. Compound 63 exhibited to possess cytotoxic activities against tumor cell lines, HL60, A549, SGC-7901, and Bel-7402, with IC 50 values 11.2, 20.9, 22.6, and 25.0 mg/mL, respectively [44].…”
Section: (1h H-3); D C 833 (C-3)]mentioning
confidence: 99%
“…Higher polymers (polyterpenoids) are encountered in materials such as rubber. In continuation of our studies on the chemical constituents from mushrooms, 44 In this chapter, we described our studies on the isolation and structure elucidation of the new terpenoids and sterols from the above mushrooms. Fungi are widespread, nonphotosynthetic microorganisms that play a vital role in the environment, particularly in the biodegradation of organic material.…”
Section: Introductionmentioning
confidence: 99%