麦角甾酮的药理活性、药代动力学及含量测定研究进展
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摘要
麦角甾酮是多种药用真菌的主要化学成分之一,具有利尿、抗肿瘤、免疫抑制、治疗慢性肾脏病等多种生物活性。基于已报道的相关文献,该文综述了麦角甾酮的波谱特征、含量测定、药理活性及药代动力学等研究进展,为深入研究与开发利用麦角甾酮提供一定价值的参考。
Ergosta-4,6,8( 14),22-tetraen-3-one( ergone) is one of main components in many medicinal fungi. Ergone has been reported to possess the activities of diuresis,cytotoxicity,antitumor,immunosuppression,as well as treatment of chronic kidney disease. According to reported literatures,an overview of spectroscopy characteristics,content determination,pharmacological activity and pharmacokinetics,etc. for ergone is presented in this review. Furthermore,the present review can provide a certain reference value for the further study and development of ergone.
Ergosta-4,6,8( 14),22-tetraen-3-one( ergone) is one of main components in many medicinal fungi. Ergone has been reported to possess the activities of diuresis,cytotoxicity,antitumor,immunosuppression,as well as treatment of chronic kidney disease. According to reported literatures,an overview of spectroscopy characteristics,content determination,pharmacological activity and pharmacokinetics,etc. for ergone is presented in this review. Furthermore,the present review can provide a certain reference value for the further study and development of ergone.
引文
[1]Bok J W,Lermer L,Chilton J,et al.Antitumor sterols from the mycelia of Cordyceps sinensis[J].Phytochemistry,1999,51(7):891.
[2]Zhao Y Y.Traditional uses,phytochemistry,pharmacology,pharmacokinetics and quality control of Polyporus umbellatus(Pers.)Fries:a review[J].J Ethnopharmacol,2013,149(1):35.
[3]Zhao Y Y,Yang L,Wang M,et al.1β-hydroxylfriedelin,a new natural pentacylic triterpene from the sclerotia of Polyporus umbellatus[J].J Chem Res,2009,11(11):699.
[4]Quang D N,Bach D D.Ergosta-4,6,8(14),22-tetraen-3-one from Vietnamese Xylaria sp.possessing inhibitory activity of nitric oxide production[J].Nat Prod Res,2008,22(10):901.
[5]Kuo Y H,Chang C I,Li S Y,et al.Cytotoxic constituents from the stems of Diospyros maritima[J].Planta Med,1997,63(4):363.
[6]Fujimoto H,Nakamura E,Okuyama E,et al.Six immunosuppressive features from an ascomycete,Zopfiella longicaudata,found in a screening study monitored by immunomodulatory activity[J].Chem Pharm Bull,2004,52(8):1005.
[7]Chobot V,Opletal L,Jahodar L,et al.Ergosta-4,6,8,22-tetraen-3-one from the edible fungus,Pleurotus ostreatus(oyster fungus)[J].Phytochemistry,1997,45(8):1669.
[8]Kovganko N V.Ecdysteroids and related compounds in fungi[J].Chem Nat Compd,1999,35(6):597.
[9]Price M J,Worth G K.The occurrence of ergosta-4,6,8(14),22-tetraen-3-one in several fungi[J].Aust J Chem,1974,27:2505.
[10]Yuan D,Mori J,Komatsu K I,et al.An anti-aldosteronic diuretic component(drain dampness)in Polyporus Sclerotium[J].Biol Pharm Bull,2004,27(6):867.
[11]Moyer J H,Morton F.Edema mechanism and management[M].London:WB Saunders Company,1960:173.
[12]Pitts R F,Sartorius O W.Mechanism of action and therapeutic use of diuretics[J].Pharmacol Rev,1950,2(1):161.
[13]Zhao Y Y.Metabolomics in chronic kidney disease[J].Clin Chim Acta,2013,422:59.
[14]Zhao Y Y,Cheng X L,Cui J H,et al.Effect of ergosta-4,6,8(14),22-tetraen-3-one(ergone)on adenine-induced chronic renal failure rat:a serum metabonomic study based on ultra performance liquid chromatography/high-sensitivity mass spectrometry coupled with Mass Lynx i-FIT algorithm[J].Clin Chim Acta,2012,413(19/20):1438.
[15]Zhao Y Y,Shen X,Cheng X L,et al.Urinary metabonomics study on the protective effects of ergosta-4,6,8(14),22-tetraen-3-one on chronic renal failure in rats using UPLC Q-TOF/MS and a novel MSEdata collection technique[J].Process Biochem,2012,47(12):1980.
[16]Zhao Y Y,Cheng X L,Wei F,et al.Application of faecal metabonomics on an experimental model of tubulointerstitial fibrosis by ultra performance liquid chromatography/high-sensitivity mass spectrometry with MSEdata collection technique[J].Biomarkers,2012,17(8):721.
[17]Zhao Y Y,Zhang L,Long F Y,et al.UPLC-Q-TOF/HSMS/MSE-based metabonomics for adenine-induced changes in metabolic profiles of rat faeces and intervention effects of ergosta-4,6,8(14),22-tetraen-3-one[J].Chem-Biol Inter,2013,301(1/3):31.
[18]Zhao Y Y,Zhang L,Mao J R,et al.Ergosta-4,6,8(14),22-tetraen-3-one isolated from Polyporus umbellatus prevents early renal injury in aristolochic acid-induced nephropathy rats[J].J Pharm Pharmacol,2011,63(12):1581.
[19]Lee W Y,Park Y,Ahn J K,et al.Cytotoxic activity of ergosta-4,6,8(14),22-tetraen-3-one from the sclerotia of Polyporus umbellatus[J].Bull Korean Chem Soc,2005,26(9):1464.
[20]Zhao Y Y,Chao X,Zhang Y,et al.Cytotoxic steroids from Polyporus umbellatus[J].Planta Med,2010,76(15):1755.
[21]Tala M F,Wabo H K,Zeng,G Z,et al.A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea[J].Phytochem Lett,2013,6(3):326.
[22]Zhao Y Y,Shen X,Chao X,et al.Ergosta-4,6,8(14),22-tetraen-3-one induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma Hep G2cells[J].Biochim Biophys Acta-Gen Subjects,2011,1810(4):384.
[23]Froufe H J C,Abreu R M V,Barros L,et al.Docking studies to evaluate mushrooms low molecular weight compounds as inhibitors of the anti-apoptotic protein BCL-2[J].Planta Med,2012,78(11):1247.
[24]Roh E M,Jin Q,Jin H G,et al.Structural implication in cytotoxic effects of sterols from Sellaginella tamariscina[J].Arch Pharm Res,2010,33(9):1347.
[25]Sun Y,Ji Z,Zhao Y,et al.Enhanced distribution and antitumor activity of ergosta-4,6,8(14),22-tetraen-3-one by polyethylene glycol liposomalization[J].J Nanosci Nanotech,2013,13(2):1435.
[26]Liang X,Sun Y,Liu L,et al.Folate-functionalized nanoparticles for controlled ergosta-4,6,8(14),22-tetraen-3-one delivery[J].Int J Pharm,2013,441(1/2):1.
[27]Liang X,Sun Y,Liu L,et al.Folate-functionalized nanoparticles for controlled ergosta-4,6,8(14),22-tetraen-3-one delivery[J].J Control Release,2013,172:e80.
[28]Fangkrathok N,Sripanidkulchai B,Umehara K,et al.Bioactive ergostanoids and a new polyhydroxyoctane from Lentinus polychrous mycelia and their inhibitory effects on E2-enhanced cell proliferation of T47D cells[J].Nat Prod Res,2013,27(18):1611.
[29]Hong Y J,Jong A R,Yang K S.Inhibition of melanin production and tyrosinase expression of ergosterol derivatives from Phellinus pini[J].Nat Prod Sci,2013,19(3):258.
[30]León F,Brouard I,Torres F,et al.A new ceramide from Suillus luteus and its cytotoxic activity against human melanoma cells[J].Chem Biodivers,2008,5(1):120.
[31]Thang T D,Kuo P C,Hwang T L,et al.Triterpenoids and steroids from Ganoderma mastoporum and their inhibitory effects on superoxide anion generation and elastase release[J].Molecules,2013,19,18(11):14285.
[32]Macías M,Gamboa A,Ulloa M,et al.Phytotoxic naphthopyranone derivatives from the coprophilous fungus Guanomyces polythrix[J].Phytochemistry,2001,58(5):751.
[33]Mata R,Gamboa A,Macias M,et al.Effect of selected phytotoxins from Guanomyces polythrix on the calmodulin-dependent activity of the enzymes c AMP phosphodiesterase and NAD-kinase[J].J Agric Food Chem,2003,51(16):4559.
[34]Zhao Y Y,Qin X Y,Zhang Y,et al.Quantitative HPLC method and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one,a natural product with diuretic activity from Polyporus umbellatus[J].Biomed Chromatogr,2010,24(10):1120.
[35]Zhao Y Y,Cheng X L,Zhang Y,et al.A fast and sensitive HPLC-MS/MS analysis and preliminary pharmacokinetic characterization of ergone in rats[J].J Chromatogr B,2010,878(1):29.
[36]Sun Y,Zhao Y Y,Li G,et al.Studies of interaction between ergosta-4,6,8(14),22-tetraen-3-one(ergone)and human serum albumin by molecular spectroscopy and modeling[J].J Chin Chem Soc-Taipei,2011,58(5):602.
[37]Liu L,Sun Y,Wei S,Hu X,Zhao Y,Fan J.Solvent effect on the absorption and fluorescence of ergone:determination of ground and excited state dipole moments[J].Spectrochim Acta A Mol Biomol Spectrosc,2012,86:120.
[38]Zhao Y Y,Cheng X L,Wei F,et al.Ultra performance liquid chromatography coupled with electrospray and atmospheric pressure chemical ionization(ESCi)-quadrupole time-of-flight mass spectrometry with novel mass spectrometryElevated Energy(MSE)data collection technique:determination and pharmacokinetics,tissue distribution and biliary excretion study of ergone in rat[J].J Sep Sci,2012,35(13):1619.
[39]Zhao Y Y,Qin X Y,Cheng X L,et al.Rapid resolution liquid chromatography-mass spectrometry and high performance liquid chromatography-fluorescence detection for metabolism and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one[J].Anal Chim Acta,2010,675(2):199.
[40]Sun Y,Liang X,Zhao Y,et al.A sensitive spectrofluorometric method for determination of ergosta-4,6,8(14),22-tetraen-3-one in rat plasma,feces,and urine for application to pharmacokinetic studies using Cerium(III)as a probe[J].Appl Spectrosc,2013,67(1):106.
[41]Zhao Y Y,Zhao Y,Zhang Y M,et al.Qualitative and quantitative analysis of the diuretic component ergone in Polyporus umbellatus by HPLC with fluorescence detection and HPLC-APCI-MS/MS[J].Pharmazie,2009,64(6):366.
[42]赵英永,程显隆,张萍,等.HPLC法测定猪苓中麦角甾酮的含量[J].药物分析杂志,2009,29(9):1579.
[43]Yuan D,Yamamoto K,Bi K,et al.Studies on the marker compounds for standardization of traditional Chinese medicine“polyporus sclerotium(ChoRei)”[J].Yakugaku Zasshi,2003,123(2):53.
[44]Zhao Y Y,Cheng X L,Zhang Y,et al.Simultaneous determination of eight major steroids from Polyporus umbellatus by high-performance liquid chromatography coupled with mass spectrometry detections[J].Biomed Chromatogr,2010,24(2):222.
[45]孙洋,赵英永,刘璐莎,等.血清蛋白对麦角甾-4,6,8,22-四烯-3-酮荧光光增强作用的研究及应用[J].化学学报,2011,69(22):2703.
[46]胡珊梅,李玲玲,肖新月,等.雷丸药材定性和定量分析方法研究[J].药物分析杂志,2010,30(9):1781.
[2]Zhao Y Y.Traditional uses,phytochemistry,pharmacology,pharmacokinetics and quality control of Polyporus umbellatus(Pers.)Fries:a review[J].J Ethnopharmacol,2013,149(1):35.
[3]Zhao Y Y,Yang L,Wang M,et al.1β-hydroxylfriedelin,a new natural pentacylic triterpene from the sclerotia of Polyporus umbellatus[J].J Chem Res,2009,11(11):699.
[4]Quang D N,Bach D D.Ergosta-4,6,8(14),22-tetraen-3-one from Vietnamese Xylaria sp.possessing inhibitory activity of nitric oxide production[J].Nat Prod Res,2008,22(10):901.
[5]Kuo Y H,Chang C I,Li S Y,et al.Cytotoxic constituents from the stems of Diospyros maritima[J].Planta Med,1997,63(4):363.
[6]Fujimoto H,Nakamura E,Okuyama E,et al.Six immunosuppressive features from an ascomycete,Zopfiella longicaudata,found in a screening study monitored by immunomodulatory activity[J].Chem Pharm Bull,2004,52(8):1005.
[7]Chobot V,Opletal L,Jahodar L,et al.Ergosta-4,6,8,22-tetraen-3-one from the edible fungus,Pleurotus ostreatus(oyster fungus)[J].Phytochemistry,1997,45(8):1669.
[8]Kovganko N V.Ecdysteroids and related compounds in fungi[J].Chem Nat Compd,1999,35(6):597.
[9]Price M J,Worth G K.The occurrence of ergosta-4,6,8(14),22-tetraen-3-one in several fungi[J].Aust J Chem,1974,27:2505.
[10]Yuan D,Mori J,Komatsu K I,et al.An anti-aldosteronic diuretic component(drain dampness)in Polyporus Sclerotium[J].Biol Pharm Bull,2004,27(6):867.
[11]Moyer J H,Morton F.Edema mechanism and management[M].London:WB Saunders Company,1960:173.
[12]Pitts R F,Sartorius O W.Mechanism of action and therapeutic use of diuretics[J].Pharmacol Rev,1950,2(1):161.
[13]Zhao Y Y.Metabolomics in chronic kidney disease[J].Clin Chim Acta,2013,422:59.
[14]Zhao Y Y,Cheng X L,Cui J H,et al.Effect of ergosta-4,6,8(14),22-tetraen-3-one(ergone)on adenine-induced chronic renal failure rat:a serum metabonomic study based on ultra performance liquid chromatography/high-sensitivity mass spectrometry coupled with Mass Lynx i-FIT algorithm[J].Clin Chim Acta,2012,413(19/20):1438.
[15]Zhao Y Y,Shen X,Cheng X L,et al.Urinary metabonomics study on the protective effects of ergosta-4,6,8(14),22-tetraen-3-one on chronic renal failure in rats using UPLC Q-TOF/MS and a novel MSEdata collection technique[J].Process Biochem,2012,47(12):1980.
[16]Zhao Y Y,Cheng X L,Wei F,et al.Application of faecal metabonomics on an experimental model of tubulointerstitial fibrosis by ultra performance liquid chromatography/high-sensitivity mass spectrometry with MSEdata collection technique[J].Biomarkers,2012,17(8):721.
[17]Zhao Y Y,Zhang L,Long F Y,et al.UPLC-Q-TOF/HSMS/MSE-based metabonomics for adenine-induced changes in metabolic profiles of rat faeces and intervention effects of ergosta-4,6,8(14),22-tetraen-3-one[J].Chem-Biol Inter,2013,301(1/3):31.
[18]Zhao Y Y,Zhang L,Mao J R,et al.Ergosta-4,6,8(14),22-tetraen-3-one isolated from Polyporus umbellatus prevents early renal injury in aristolochic acid-induced nephropathy rats[J].J Pharm Pharmacol,2011,63(12):1581.
[19]Lee W Y,Park Y,Ahn J K,et al.Cytotoxic activity of ergosta-4,6,8(14),22-tetraen-3-one from the sclerotia of Polyporus umbellatus[J].Bull Korean Chem Soc,2005,26(9):1464.
[20]Zhao Y Y,Chao X,Zhang Y,et al.Cytotoxic steroids from Polyporus umbellatus[J].Planta Med,2010,76(15):1755.
[21]Tala M F,Wabo H K,Zeng,G Z,et al.A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea[J].Phytochem Lett,2013,6(3):326.
[22]Zhao Y Y,Shen X,Chao X,et al.Ergosta-4,6,8(14),22-tetraen-3-one induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma Hep G2cells[J].Biochim Biophys Acta-Gen Subjects,2011,1810(4):384.
[23]Froufe H J C,Abreu R M V,Barros L,et al.Docking studies to evaluate mushrooms low molecular weight compounds as inhibitors of the anti-apoptotic protein BCL-2[J].Planta Med,2012,78(11):1247.
[24]Roh E M,Jin Q,Jin H G,et al.Structural implication in cytotoxic effects of sterols from Sellaginella tamariscina[J].Arch Pharm Res,2010,33(9):1347.
[25]Sun Y,Ji Z,Zhao Y,et al.Enhanced distribution and antitumor activity of ergosta-4,6,8(14),22-tetraen-3-one by polyethylene glycol liposomalization[J].J Nanosci Nanotech,2013,13(2):1435.
[26]Liang X,Sun Y,Liu L,et al.Folate-functionalized nanoparticles for controlled ergosta-4,6,8(14),22-tetraen-3-one delivery[J].Int J Pharm,2013,441(1/2):1.
[27]Liang X,Sun Y,Liu L,et al.Folate-functionalized nanoparticles for controlled ergosta-4,6,8(14),22-tetraen-3-one delivery[J].J Control Release,2013,172:e80.
[28]Fangkrathok N,Sripanidkulchai B,Umehara K,et al.Bioactive ergostanoids and a new polyhydroxyoctane from Lentinus polychrous mycelia and their inhibitory effects on E2-enhanced cell proliferation of T47D cells[J].Nat Prod Res,2013,27(18):1611.
[29]Hong Y J,Jong A R,Yang K S.Inhibition of melanin production and tyrosinase expression of ergosterol derivatives from Phellinus pini[J].Nat Prod Sci,2013,19(3):258.
[30]León F,Brouard I,Torres F,et al.A new ceramide from Suillus luteus and its cytotoxic activity against human melanoma cells[J].Chem Biodivers,2008,5(1):120.
[31]Thang T D,Kuo P C,Hwang T L,et al.Triterpenoids and steroids from Ganoderma mastoporum and their inhibitory effects on superoxide anion generation and elastase release[J].Molecules,2013,19,18(11):14285.
[32]Macías M,Gamboa A,Ulloa M,et al.Phytotoxic naphthopyranone derivatives from the coprophilous fungus Guanomyces polythrix[J].Phytochemistry,2001,58(5):751.
[33]Mata R,Gamboa A,Macias M,et al.Effect of selected phytotoxins from Guanomyces polythrix on the calmodulin-dependent activity of the enzymes c AMP phosphodiesterase and NAD-kinase[J].J Agric Food Chem,2003,51(16):4559.
[34]Zhao Y Y,Qin X Y,Zhang Y,et al.Quantitative HPLC method and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one,a natural product with diuretic activity from Polyporus umbellatus[J].Biomed Chromatogr,2010,24(10):1120.
[35]Zhao Y Y,Cheng X L,Zhang Y,et al.A fast and sensitive HPLC-MS/MS analysis and preliminary pharmacokinetic characterization of ergone in rats[J].J Chromatogr B,2010,878(1):29.
[36]Sun Y,Zhao Y Y,Li G,et al.Studies of interaction between ergosta-4,6,8(14),22-tetraen-3-one(ergone)and human serum albumin by molecular spectroscopy and modeling[J].J Chin Chem Soc-Taipei,2011,58(5):602.
[37]Liu L,Sun Y,Wei S,Hu X,Zhao Y,Fan J.Solvent effect on the absorption and fluorescence of ergone:determination of ground and excited state dipole moments[J].Spectrochim Acta A Mol Biomol Spectrosc,2012,86:120.
[38]Zhao Y Y,Cheng X L,Wei F,et al.Ultra performance liquid chromatography coupled with electrospray and atmospheric pressure chemical ionization(ESCi)-quadrupole time-of-flight mass spectrometry with novel mass spectrometryElevated Energy(MSE)data collection technique:determination and pharmacokinetics,tissue distribution and biliary excretion study of ergone in rat[J].J Sep Sci,2012,35(13):1619.
[39]Zhao Y Y,Qin X Y,Cheng X L,et al.Rapid resolution liquid chromatography-mass spectrometry and high performance liquid chromatography-fluorescence detection for metabolism and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one[J].Anal Chim Acta,2010,675(2):199.
[40]Sun Y,Liang X,Zhao Y,et al.A sensitive spectrofluorometric method for determination of ergosta-4,6,8(14),22-tetraen-3-one in rat plasma,feces,and urine for application to pharmacokinetic studies using Cerium(III)as a probe[J].Appl Spectrosc,2013,67(1):106.
[41]Zhao Y Y,Zhao Y,Zhang Y M,et al.Qualitative and quantitative analysis of the diuretic component ergone in Polyporus umbellatus by HPLC with fluorescence detection and HPLC-APCI-MS/MS[J].Pharmazie,2009,64(6):366.
[42]赵英永,程显隆,张萍,等.HPLC法测定猪苓中麦角甾酮的含量[J].药物分析杂志,2009,29(9):1579.
[43]Yuan D,Yamamoto K,Bi K,et al.Studies on the marker compounds for standardization of traditional Chinese medicine“polyporus sclerotium(ChoRei)”[J].Yakugaku Zasshi,2003,123(2):53.
[44]Zhao Y Y,Cheng X L,Zhang Y,et al.Simultaneous determination of eight major steroids from Polyporus umbellatus by high-performance liquid chromatography coupled with mass spectrometry detections[J].Biomed Chromatogr,2010,24(2):222.
[45]孙洋,赵英永,刘璐莎,等.血清蛋白对麦角甾-4,6,8,22-四烯-3-酮荧光光增强作用的研究及应用[J].化学学报,2011,69(22):2703.
[46]胡珊梅,李玲玲,肖新月,等.雷丸药材定性和定量分析方法研究[J].药物分析杂志,2010,30(9):1781.