Isolation of lanostane-type triterpene acids having an acetoxyl group from sclerotia of Poria cocos

Tai, Takaaki; Shingu, Tetsuro; Kikuchi, Tohru; Tezuka, Yasuhiro; Akahori, Akira

doi:10.1016/0031-9422(95)00182-7

Cited by 58 publications

(48 citation statements)

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“…PCB and PCC were then subjected to repeated column chromatography to isolate pure compounds. In all, nine lanostane-type triterpenes, including pachymic acid (1), 15) dehydropachymic acid (2), 15) 3-acetyloxy-16a-hydroxytrametenolic acid (3), 16) polyporenic acid C (4), 4) 3-epi-dehydropachymic acid (5), 16) 3-epi-dehydrotumulosic acid (6), 3,17) tumulosic acid (7), 29-hydroxypolyporenic acid C (8), and dehydrotumulosic acid (9) 17) were isolated and identified. Identification of known compounds was conducted by comparison of their physical and spectroscopic data ( 1 H-, 13 C-NMR and MS) with the corresponding compounds reported in the literatures.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic and Anti-oxidant Activities of Lanostane-Type Triterpenes Isolated from Poria cocos

et al. 2008

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NotesPoria cocos (P. cocos), which is also known as Fu Ling, is often used in Chinese traditional medicine for its diuretic and sedative effects.1) Compounds with anti-cancer properties have been isolated from both the aqueous and alcoholic extracts of P. cocos in various studies.2-7) Polysaccharides from aqueous extracts have also been shown to exhibit various anti-tumor and cytotoxic effects against certain cancer cell lines.8-10) Likewise, lanostane-type triterpenes from alcoholic extracts were shown to possess certain anti-cancer properties, including inhibition of DNA polymerases, 4,11) inhibition of tumor cell growth induced by TPA (12-O-tetradecanoylphorbol-13-acetate), 2,12,13) and inhibition of DNA topoisomerase II.4) Cytotoxicity of lanostane-type triterpenes against certain human cancer cell lines have also been reported. 2,3,14) Recently, we have shown that pachymic acid (1), a lanostane-type triterpene found in P. cocos alcoholic extract, is effective in preventing the growth of both androgenresponsive and -insensitive prostate cancer cells by inducing apoptosis in a dose-and time-dependent fashion.5) This finding, together with the observation that various lanostane-type triterpenes have been isolated from this plant, have motivated us to conduct further research on P. cocos to identify other pachymic acid-like compounds with equal or greater cytotoxicity. We report here the isolation and characterization of one novel and eight known lanostane-type triterpenes from the sclerotia of P. cocos, and the cytotoxic and antioxidant activity of these triterpenes. Results and DiscussionTo isolate compounds from P. cocos, dry sclerotia of P. cocos were crushed and extracted using 95% ethanol at 60°C under reflux. Subsequently, the alcoholic extracts were dried and fractionated using flash column chromatography. In all, four fractions, PC A-D, were obtained and evaluated for their cytotoxic activity against DU145 and A549 cells. Of these fractions, PCB gave the best response, which, at 37 mg/ml, caused cell viability of DU145 and A549 to decrease to 67.7% and 44%, respectively, after 72 h treatment (data not shown to conserve space). This was followed by PCC, which had slightly lower cytotoxicity against DU145 growth (84.7% vs. 67.7% growth inhibition at 37 mg/ml over a 72 h treatment period) relative to PCB but similar inhibiting activity as PCB on A549 cells (data not shown). PCB and PCC were then subjected to repeated column chromatography to isolate pure compounds. In all, nine lanostane-type triterpenes, including pachymic acid (1), 15) dehydropachymic acid (2), 15) 3-acetyloxy-16a-hydroxytrametenolic acid (3), 16) polyporenic acid C (4), 4) 3-epi-dehydropachymic acid (5), 16) 3-epi-dehydrotumulosic acid (6), 3,17) tumulosic acid (7), 29-hydroxypolyporenic acid C (8), and dehydrotumulosic acid (9) 17) were isolated and identified. Identification of known compounds was conducted by comparison of their physical and spectroscopic data ( 1 H-, 13 C-NMR and MS) with the corresponding compounds reported in the...

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Section: Resultsmentioning

confidence: 99%

Cytotoxic and Anti-oxidant Activities of Lanostane-Type Triterpenes Isolated from Poria cocos

et al. 2008

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“…The main chemical constituents of P. cocos are polysaccharides, triterpenoids, egosterol and proteins (Tai, Akahori, & Shingu, 1992;Tai, Shingu, Kikuchi, Tezuka, & Akahori, 1995a;Tai, Shingu, Kikuchi, Tezuka, & Akahori, 1995b;Wang & Wan, 1998;Yang & Bao, 2005), in which triterpenoids are found to possess interesting pharmacological actions such as cytotoxic and anti-oxidant (Zhou et al, 2008), anti-cancer (Gapter, Wang, Glinski, & Ng, 2005), anti-inflammatory (Yasukawa et al, 1998), inhibition of free radical-induced lysis of red blood cells (Sekiya, Goto, Shimada, & Terasawa, 1998) and inhibition of calf DNA polymerase a and rat DNA polymerase b (Akihisa et al, 2004;Kaminaga et al, 1996). Up to now, more than 80 triterpenoid compounds were isolated and identified from P. cocos with the above-mentioned bioactivities.…”

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Advanced ultra-performance liquid chromatography–photodiode array–quadrupole time-of-flight mass spectrometric methods for simultaneous screening and quantification of triterpenoids in Poria cocos

et al. 2014

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“…Both dehydrotrametenonic acid and dehydroebriconic acid could prevent the growth of human gastric cancer cells, and their LD 50 values were 63. 6 o study the in vivo roles of mammalian DNA polymerases, we have tried to screen and isolate selective inhibitors from natural products. In the process, we found that many of the newly found polymerase inhibitors were also inhibitors of eukaryotic DNA topoisomerases, 1,2) and both the polymerases and the topoisomerases have a three-dimensionally very similar pocket accepting DNA.…”

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“…3,4) Whereas the inner parts, called Fu-Ling in Chinese, of the sclerotia of P. cocos were reported to have an invigorating activity in addition to diuretic and sedative activities, the epidermis (Fu-Ling-Pi in Chinese) of the sclerotia is reported to have only a diuretic activity and no invigorating activity. 3) Both the inner parts [4][5][6][7][8] and the epidermis 9,10) of the sclerotia of P. cocos were reported to contain several lanostane-type triterpene acids, 9,10) which were suggested to be the major medicinal components of the plant. Several of the lanostane-type triterpene acids were revealed to possess potent inhibitory effects on tumor cell growth.…”

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A novel DNA topoisomerase inhibitor: dehydroebriconic acid, one of the lanostane‐type triterpene acids from Poria cocos

et al. 2004

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Traditional Chinese medicinal plants are a treasure house for screening novel inhibitors of DNA polymerases and DNA topoisomerases from mammals; in the present study, nine lanostanetype triterpene acids were found in sclerotium of Poria cocos. Among the nine compounds, only dehydroebriconic acid could potently inhibit DNA topoisomerase II (topo II) activity (IC50=4.6 μM), while the compound moderately inhibited the activities of DNA polymerases α, β, γ, δ, ɛ, η, iota;, κ and λ only from mammals, to similar extents. Another compound, dehydrotrametenonic acid, also showed moderate inhibitory effects against topo II (IC50=37.5 μM) and weak effects against all the polymerases tested. Both compounds showed no inhibitory effect against topo I, higher plant (cauliflower) DNA polymerase I (α‐like polymerase) or II (βlike polymerase), calf thymus terminal deoxynucleotidyl transferase, human immunodeficiency virus type‐1 reverse transcriptase, prokaryotic DNA polymerases such as the Klenow fragment of E. coli DNA polymerase I, Taq DNA polymerase and T4 DNA polymerase, or DNA metabolic enzymes such as T7 RNA polymerase, T4 polynucleotide kinase and bovine deoxyribonu‐clease I. These findings suggest that dehydroebriconic acid and dehydrotrametenonic acid should be designated as topo II‐preferential inhibitors, although they also moderately inhibited all the mammalian DNA polymerases tested. Both dehydrotrametenonic acid and dehydroebriconic acid could prevent the growth of human gastric cancer cells, and their LD50 values were 63.6 and 38.4 μM, respectively. The cells were halted at the G1 phase in the cell cycle. The relation between the structure of triterpene acids and their inhibitory activities is discussed.

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Isolation of lanostane-type triterpene acids having an acetoxyl group from sclerotia of Poria cocos

Cited by 58 publications

References 4 publications

Cytotoxic and Anti-oxidant Activities of Lanostane-Type Triterpenes Isolated from Poria cocos

Cytotoxic and Anti-oxidant Activities of Lanostane-Type Triterpenes Isolated from Poria cocos

Advanced ultra-performance liquid chromatography–photodiode array–quadrupole time-of-flight mass spectrometric methods for simultaneous screening and quantification of triterpenoids in Poria cocos

A novel DNA topoisomerase inhibitor: dehydroebriconic acid, one of the lanostane‐type triterpene acids from Poria cocos

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