虫草及相关真菌的次生代谢产物及其活性Secondary metabolites and their bioactivities of Cordyceps and its related fungi
胡丰林;李增智;
摘要(Abstract):
全面系统地总结了目前在虫草及相关真菌中次生代谢产物研究方面的最新成果,发现目前在虫草及其密切相关的虫生真菌中共报道272个有具体结构的化合物,其活性涉及杀虫、抗癌、抗菌、免疫调节和抗疟原虫等多方面。这些化合物主要来源于20余种虫草、虫草无性型或与虫草密切相关的虫生真菌。虽然近年来有关虫草中生物活性代谢物的研究受到世界各国广泛关注,但仍有90%以上虫草及相关虫生真菌种类中尚无任何具体成分的研究报道,因此有关研究尚需要进一步深入。
关键词(KeyWords): 虫生真菌;生物活性物质
基金项目(Foundation): 国家自然科学基金项目(No.30570189);; 安徽省自然科学基金项目(No.00042425);; 安徽高校自然科学研究重点项目(No.DT200708)
作者(Authors): 胡丰林;李增智;
参考文献(References):
- Anon.,1999.Chinese Materia Medica.Edited by Chinese Materia Medica Committee.Shanghai:Shanghai Science and Technology Press.489~495(in Chinese)
- Anon.,2005.Pharmacopoeia of the People’s Republic of China(PartⅠ).Beijing:Science and Technology Press.1~633(in Chinese)
- Bok JW,Lermer L,Chilton J,1999.Antitumor sterols from the mycelia of Cordyceps sinensis.Phytochem,51:891~898
- Boros C,Hamilton SM,Katz B,1994.Comparison of balanol from Verticillium balanoides and ophiocordin from Cordyceps ophioglossoides.J Antibiot(Tokyo),47(9):1010~1016
- Buenz EJ,Bauer BA,Osmundson TW,2005.The traditional Chinese medicine Cordyceps sinensis and its effects on apoptotic homeostasis.J Ethnopharmacol,96:19~29
- Chen YJ,Shiao MS,Lee SS,1997.Effect of Cordyceps sinensis on the proliferation and differentiation of human leukemic U937cells.Life Sci,60:2349~2359
- Chen LT,Cao HF,Huang WF,2005.Components,pharmacological activities and applications of Cordyceps militaris.Mod Food Sci,21(3):192~195(in Chinese)
- Cheng YX,Li ZZ,Hamburger M,2004.Farinosones A-C,neurotrophic alkaloidal metabolites from the entomogenous deuteromycete Paecilomyces farinosus.J Nat Prod,67:1854~1858
- Chiou WF,Chang PC,Chou CJ,2000.Protein constituent contributes to the hypotensive and vasorelaxant activities of Codyceps sinensis.Life Sci,66:1369~1376
- Dunn CJ,2001.A review on Cyclosporins from fungi.Drugs,61:1957~2016
- Feng YJ,Blunt JW,Cole A,Munro M,2002.The isolation of two new chromone derivatives from the New Zealand fungus Tolypocladium extinguens.J Nat Prod,65:1681~1682
- Feng XZ,1995.Chemical constituents of Cordyceps sinensis and cultural Cordyceps.Modernization Studies on Chinese Herbal Medicine,1:99~103(in Chinese)
- Fu L,Chen ZH,2004.Research advances of chemical constituents and pharmacological activities of Cordyceps.Life Sci,8(1):1~5(in Chinese)
- Fujita T,Inoue K,Yamamoto S,1994.Fungal metabolites.Part11.A potent immunosuppressive activity found in Isaria sinclairii metabolite.J Antibiot,47:208~215
- Furuya T,Hirotani M,Matsuzawa M,1983.N6-(2’-hydroxyethyl)-adenosine,a biologically active compound from cultured mycelia of Cordyceps and Isaria species.Phytochem,22:509~512
- Gupta S,Montllor C,Hwang YS,1995.Isolation of novel beauvericin analogues from the fungus Beauveria bassiana.J Nat Prod,58:733~738
- Hamill RL,Higgens CE,Goman M,1969.The structure of beauvericin,a new depsipepide antibiotic toxic to Artemia salina,Ttetrahedron Lett,49:4255~4258
- Hsiao YM,Ko JL,2001.Determination of destruxins,cyclic peptide toxins,produced by different strains of Metarhizium anisopliae and their mutants induced by ethyl methane sulfonate and ultraviolet using HPLC method.Toxicon,39(6):837~41
- Hu FL,2006.Metabolite comparison and bioactive compounds high throughput screening and identification in some entomogenous fungi.A dissertation of the requirements for a Ph.D.degree from Anhui Agricultural University.1~183
- Hu FL,Schmidt K,Li ZZ,Hamburger M,2002.Free radical scavengers from the entomogenous deuteromycete Beauveria amorpha.Planta Medica,68:64~65
- Hu Z,Xia BG,Wu XG,2005.Novel components from Cordyceps sinensis.Chin Edib Fungi,23(5):37~38(in Chinese)
- Isaka M,Kongsaeree P,Thebtaranonth Y,2001.Bioxanthracenes from the insect pathogenic fungus Cordyceps pseudomilitaris BCC1620.II.Structure elucidation.J Antibiot,54:36~43
- Isaka M,Kitakoop P,Kirtikara K,2005a.Bioactive substances from insect pathogenic fungi.Acc Chem Res,38(10):813~823
- Isaka M,Palasarn S,Sriklung K,2005b.Cyclohexadepsipeptides from the insect pathogenic fungus Hirsutella nivea BCC2594.J Nat Prod,68:1680~1682
- Isaka M,Rugseree N,Maithip P,2005c.Hirsutellones A~E,antimycobacterial alkaloids from the insect pathogenic fungus Hirsutella nivea BCC2594.Tetrahedron Lett,61(5):577~583
- Isaka M,Tanticharoen M,Thebtaranonth Y,2000.Cordyanhydrides A and B,two unique anhydrides from the insect pathogenic fungus Cordyceps pseudomilitaris BCC1620.Tetrahedron Lett,41:1657~1660
- Jaturapat A,Isaka M,Hywel-Jones NL,2001.Bioxanthracenes from the insect pathogenic fungus Cordyceps pseudomilitaris BCC1620.I.Taxonomy,fermentation,isolation,and antimalarial activity.J Antibiot,54:29~35
- Jegorov A,Sedmera P,Havlicek V,1998.Destruxin Ed1,a cyclopeptide from the fungus Metarhizium anisopliae.Phytochem,49(6):1815~1857
- Jia JM,Ma XC,Wu CF,2005.Cordycedipeptide A,a new cyclodipeptide from the culture liquid of Cordyceps sinensis(Berk.)Sacc.Chem Pharm Bull(Tokyo),53(5):582~583
- Jiang H,Liu K,Men S,2000.Chemical constuents of the dry sorophore of Cordyceps militaris.Acta Pharmaceutica Sin,35(9):663~668(in Chinese)
- Jin DQ,Park BC,Lee JS,2004.Mycelial extract of Cordyceps ophioglossoides prevents neuronal cell death and ameliorates beta-amyloid peptide-induced memory deficits in rats.Biol Pharm Bull,27(7):1126~1129
- Kawagishi H,Okamura K,Kobayashi F,2004.Estrogenic substances from the mycelia of medicinal fungus Cordyceps ophioglossoides.Int J Med Mushr,6(3):249~251
- Khachatourians GG,1996.Biochemistry and molecular biology of entomopathogenic fungi.In:Miller H(ed.)the Mycota VI:Humans and Animal Relationships.Berlin:Spring Verlag.336~339
- Kiho T,Ookubo K,Usui S,1999.Structural features and hypoglycemic activity of a polysaccharide(CS~F10)from the cultured mycelium of Cordyceps sinensis.Biol Pharm Bull,22:966~970
- Kikuchi H,Miyagawa Y,Nakamura K,2004a.A novel carbon skeletal trichothecane,tenuipesi A,isolated from an entomopathogenic fungus,Paecilomyces tenuipes.Org Lett,6(24):4531~4533
- Kikuchi H,Miyagawa Y,Sahashi Y,2004b.Novel spirocyclic trichothecanes,spirotenuipesine A and B,isolated from entomopathogenic fungus,Paecilomyces tenuipes.J Org Chem,69:352~356
- Kikuchi H,Takahashi N,Oshima Y,2004c.Novel aromatics bearing4-methylglucose unit isolated from the oriental crude drug Bombyx Batryticatus.Tetrahedron Lett,45:367~370
- Kittakoop P,Punya J,Kongsaeree P,1999.Bioactive naphthoquinones from Cordyceps unilateralis.Phytochem,52:453~457
- Kneifel H,Konig WA,Loeffler W,1977.Ophiocordin,an antifungal antibiotic from Cordyceps ophioglossoides.Arch Microbiol,113:121~130
- Kolter T,Sandhoff K,1999.Sphingolipids:their metabolic pathways and the pathobiochemistry of neurodegenerative disease.Angrew Chem Int Edit,38(4):1532~1568
- Kuo YC,Weng SC,Chou CJ,2003.Activation and proliferation signals in primary human T lymphocytes inhibited by ergosterol peroxide isolated from Cordyceps cicadae.J Pharmcol,140(5):895~906
- Kuo YC,Tsai WJ,Wang JY,2001.Regulation of bronchoalveolar lavage fluids cell function by the immunomodulatory agents from Cordyceps sinensis.Life Sci,68:1067~1082
- Lang G,Blunt JW,Cummings NJ,2005.A cyclic tetrapeptide from a spider-derived entomopathogenic fungus,Hirsutella sp.J Nat Prod,68:1303~1305
- Leger RJ,Bidochka MJ,Roberts DW,1994.Characterization of a novel carboxypeptidase produced by the entomopathogenic fungus Metarhizium anisopliae.Arch Biochem Biophys,314(2):392~398
- Li ZZ,Li CR,Huang B,Fan MZ,2001.Discovery and demonstration of the teleomorph of Beauveria bassiana,an important entomogenous fungus.Chin Sci Bull,46:751~753
- Liang ZQ,2001.Current situation and ponderation of Cordyceps research and exploitation in China.Acta Edulis Fungi,8(2):53~62(in Chinese)
- Li CR,2003.Research advances in anamorph of Cordyceps in recent10years.Research and Utilization of Chinese Entomogenous Fungi,5:45~48(in Chinese)
- Lin CY,Lin CC,Chen CC,2004.The isolation of active fraction and active compound from Cordyceps sinensis can be used to improve bronchial hyperresponsiveness.Patent,CODEN:TWXXA5,CLASS:ICM:A61K035~84,APPLICATION:TW1999-88120132
- Li JX,Li J,Xu LZ,2003.Chemical constituents of Cordyceps sinensis from Tibet.J Chin Pharmaceut,38(7):499~501(in Chinese)
- Liu JK,Hu L,Ding ZH,2003.Metabolites and activities of higher fungi.J Chin Herb Med,34(1):84~86(in Chinese)
- Ma XC,Huang J,Liu D,2003.Studies on components of cultural broth of Cordyceps militaris.Journal of Shenyang Pharmceutical University,20(4):255~257(in Chinese)
- Mehdi L,Arie D,Marc D,2004.Anti-plasmodium activity of ceramide analogs.Malaria Journal,3:49~59
- Melissa MW,Donna MG,Jon C,2002.Akanthomycin,a new antibiotic pyridone from the entomopathogenic fungus Akanthomyces gracilis.Org Lett,4(5):671~673
- Nakamura T,2002.Synthesis of sphingofungin analogs.Tetrahedron,58(8):779~791
- Nam KS,Jo YS,Kim YH,2001.Cytotoxic activities of acetoxyscripenediol and ergosterol peroxide from Paecilomyces tenuipes.Life Sci,69(2):229~237
- Nilanonta C,Isaka M,Kittakoop P,2000.Antimycobacterial and antiplasmodial cyclodepsipeptides from the insect pathogenic fungus Paecilomyces tenuipes BCC1614.Planta Medica,66:756~758
- Nilanonta C,Isaka M,Kittakoop P,2002.Precursor-directed biosynthesis of beauvericin analogs by the insect pathogenic fungus Paecilomyces tenuipes BCC1614.Tetrahedron,58:355~360.
- Odier F,Vey A,Bureau JP,1992.In vitro effect of fungal cyclodepsipeptides on leukemic cells:study of destruxins A,B and E.Biol Cell,74(3):267~271
- Ohmori T,Tamura K,Tsuru S,1986.Antitumor activity of protein~bound polysaccharide from Cordyceps ophioglossoides.Jpn J Cancer Res,77(12):1256~1263
- Ohmori T,Tamura K,Ohgane N,1989.The correlation between molecular weight and antitumor activity of galactosaminoglycan(CO-N)from Cordyceps ophioglossoides.Chem Pharm Bull(Tokyo),37(5):1337~1340
- Park IW,Hwang GS,Kim HW,2004.Characterization of acetoxyscirpendiol of Paecilomyces tenuipes as inhibitor of sodium glucose co-transporters expressed in Xenopus laevis oocytes.J Appl Pharmacol,12(4):250~256
- Peeters H,Zocher R,Madry N,1983.Incorporation of radioactive precursors into beauvericin produced by Paecilomyces fumosoroseus.Phytochem,22:1719~1720
- Pu ZL,Li ZZ,1996.Insect Mycology,Hefei:Anhui Science and Technology Press.1~714(in Chinese)
- Puder C,Wagner K,Vettermann R,2005.Terphenylquinone inhibitors of the Src protein tyrosine kinase from Stilbella sp.J Nat Prod,68:323~326
- Quesada ME,Vey A,2004.Bassiacridin,a protein toxin for locusts secreted by the entomopathogenic fungus Beauveria bassiana.Mycol Res,108(4):441~452
- Riley RT,Plattner RD,2000.Fermentation,partial purification,and use of serine palmitoyltransferase inhibitors from Cordyceps sinclairii.Methods Enzymol,311:348~36
- Rukachaisirikul V,Chantaruk S,Tansakul C,2006.A cyclopeptide from the insect pathogenic fungus Cordyceps sp.BCC1788.J Nat Prod,69(2):305~307
- Rukachaisirikul V,Pramjit S,Pakawatchai C,2004.10-membered macrolides from the insect pathogenic fungus Cordyceps militaris.J Nat Prod,67(11):1953~1955
- Schimidt K,Riese U,Li ZZ,Hamburger M,2003.Noval tetramic acids and pyridone alkaloids,militarinones B,C and D,from the insect pathogenic fungus Paecilomyces militaris.J Nat Prod,66:378~383
- Schimidt K,Wolfgang G,Li ZZ,Hamburger M,2002.Militarinones A,a noval pyridone alkaloid from Paecilomyce militaris.Org Lett,4:179~199
- Seephonkai P,Isaka M,Kittakoop P,2001.A new tropolone from the insect pathogenic fungus Cordyceps sp.BCC1681.J Antibiot,54:751~752
- Skrobek A,Butt TM,2005.Toxicity testing of destruxins and crude extracts from the insectpathogenic fungus Metarhizium anisopliae.FEMS Microbiol Lett,251(1):23~28
- Su L,Lou FC,Zhao SX,2001.Studies on chemical constituents of cultural Cordyceps mycelia.Progress in Pharmaceuticals,25(1):43~45(in Chinese)
- Takahashi S,Kakinuma N,Uchhida K,1998.Pyridovericin and pyridomacrolidin:novel metabolites from entomopathogenic fungi,Beauveria bassiana.J Antibiot,51(6):596~598
- Toki S,Ando K,Kawamoto I,1992a.ES-242-2,3,4,5,6,7,and8,novel bioxanthracenes produced by Verticillium sp.,which act on the N-methyl-D-aspartate receptor.J Antibiot,45:1047~1054
- Toki S,Ando K,Yoshida M,1992b.ES-242-1,a novel compound from Verticillium sp.,binds to a site on N-methyl-D-aspartate receptor that is coupled to the channel domain.J Antibiot,45:1088~1093
- Unakul P,Wongsa P,Kittakoop P,2005.Production of red pigments by insect pathogenic fungus Cordyceps unilateralis BCC1869.J Ind Microbiol Biotechnol,32(4):135~140
- Vey A,Matha V,Dumas C,2002.Effects of the peptide mycotoxin destruxin E on insect haemocytes and on dynamics and efficiency of the multicellular immune reaction.J Invertebr Pathol,80(3):177~187
- Vongvilai P,Isaka M,Kittakoop P,2004.Isolation and structure elucidation of enniatins L,M1,M2,and N:novel hydroxy analogs.Helv Chem Acta,87:2066~2073
- Vongvanich N,Kittakoop P,Isaka M,2002.Hirsutellide A,a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii.J Nat Prod,65:1346~1348
- Wang C,Skrobek A,Butt TM,2004.Investigations on the destruxin production of the entomopathogenic fungus Metarhizium anisopliae.J Invertebr Pathol,85(3):168~74
- Wang G,Ma BJ,Liu JK,2004,Chemical constuents of cultured Cordyceps militaris.J Chin Gerb Med,35(5):493~495(in Chinese)
- Weng SD,Chou CJ,Lin LC,2002.Immunomodulatory functions of extracts from the Chinese medicinal fungus Cordyceps cicadae.J Ethnopharmacol,83(1~2):79~85
- Won SY,Park EH,2005.Anti-inflammatory and related pharmacological activities of cultured mycelia and fruiting bodies of Cordyceps militaris.J Ethnopharmacol,96(3):555~561
- Wu YL,Sun CR,Pan YJ,2006.Studies on isolation and structural features of a polysaccharide from the mycelium of a Chinese edible fungus(Cordyceps sinensis).Carbohydrate Polymers,63:251~256
- Wu YL,Ishurd O,Sun CR,2005a.Structure analysis and antitumor activity of(1->3)-beta-D-glucans(cordyglucans)from the mycelia of Cordyceps sinensis.Planta Medica,71(4):381~384
- Wu YL,Sun CR,Pan YJ,2005b.Structural analysis of a neutral(1-3),(1-4)-β-D-glucan from the mycelia of Cordyceps sinensis.J Nat Prod,68:812~814
- Yamada H,Kawaguchi N,Ohmori T,1984.Structure and antitumor activity of an alkasolubal polysacchride from Cordyceps ophioglossoides.Carbohydrate Research,125(1):107~115
- Yoo O,Son JH,Lee DH,2005.4-acetoxyscirpendiol of Paecilomyces tenuipes inhibits Na+/D-glucose cotransporter expressed in Xenopus laevis oocytes.J Biochem Mol Biol,38(2):211~217
- Yu R,Song L,Zhao Y,2004a.Isolation and biological properties of polysaccharide CPS-1from cultured Cordyceps militaris.Fitoterapia,75(5):465~472
- Yu R,Wang L,Zhang H,2004b.Isolation,purification and identification of polysaccharides from cultured Cordyceps militaris.Fitoterapia,75(7):662~666
- Zhu JS,Halpern GM,Kenneth J,1998.The scientific rediscovery of an ancient Chinese herbal medicine:Cordyceps sinenAlternative and Complementary Medicine,4(3):289~303
- 陈俐彤,曹红峰,黄文芳,2005.蛹虫草的化学成分、药效及应用.现代食品科技,21(3):192~195
- 国家药典编委会编,2005.中华人民共和国药典(第一部).北京:化学工业出版社.1~633
- 冯孝章,1995.冬虫夏草及人工虫草化学成分.中草药现代化研究,1:99~103
- 傅岚,陈作红,2004.虫草属真菌化学成分及药理作用研究进展.生命科学研究,8(1):1~5
- 胡丰林,2006.虫生真菌代谢物比较分析及生物活性物质高通量筛选与鉴定研究.安徽农业大学博士学位论文,1~183
- 胡征,夏服宝,吴小刚,2005.冬虫夏草新药效成分分析.中国食用菌,23(5):37~38
- 姜泓,刘珂,孟舒,2000.人工蛹虫草子实体化学成分.药学学报,35(9):663~668
- 李春如,2003.近十年虫草无性型研究进展.中国虫生真菌研究与应用,5:45~48
- 郦皆秀,李进,徐丽珍,2003.西藏产冬虫夏草化学成分研究.中国药学杂志,38(7):499~501
- 梁宗琦,2001.我国虫草属真菌研究开发的现状及思考.食用菌学报,8(2):53~62
- 刘吉开,胡琳,丁智慧,2003.高等真菌代谢产物及其活性.中草药,34(1):84~86
- 马骁弛,黄健,刘丹,2003.蛹虫草培养液成分研究.沈阳药科大学学报,20(4):255~257
- 蒲蛰龙,李增智,1996.昆虫真菌学.合肥:安徽科学技术出版社.1~714
- 苏亮,楼凤昌,赵守训,2001.虫草头孢菌丝体化学成分的研究.药学进展,25(1):43~45
- 王刚,麻兵继,刘吉开,2004.人工蛹虫草化学成分研究.中草药,35(5):493~495
- 中华本草编委会,1999.中华本草.上海:上海科学技术出版社.489~495