一株番荔枝内生真菌F-31的化学成分研究
|
摘要
植物内生真菌是天然活性化合物的一个重要来源。本论文对一株来源于海南刺果番荔枝、能够抑制肿瘤细胞增殖的内生真菌(F-31)进行了菌种鉴定、放大发酵培养以及活性化学成分的研究。菌种鉴定表明,菌株F-31可能为黑团孢霉属的一个新种(Periconia sp.)。
应用硅胶柱色谱、薄层色谱、Sephadex LH-20凝胶柱色谱、正相及反相高效液相色谱等各种色谱手段对F-31发酵液的乙酸乙酯提取物和菌丝体的水层提取物分别进行了分离纯化,共得到11个化合物,并采用各种现代波谱技术对分离到的化合物进行了结构鉴定,其中6个化合物为新化合物。这些化合物包括：3个倍半萜类化合物(4S,5R,9S, 11S,12S)-Periconone A (1)、(3S,6S,7R,8S)-Periconone B (5)和Chloranthalactone E (6),1个二萜类化合物(6S,9R,10R,1 2R,16R)-Periconone C (3),1个单萜内酯(-)-(1R,4S,6R,7R)-2-Caren-4,9-olide (4),1个内酯类化合物4-(3'-Hydroxybutyl)-4H-furan-1-one (11),2个氨基酸类化合物L-色氨酸(8)和L-苯丙氨酸(10),1个醌类化合物7-hydroxy-11β,12α-di methyl-9,10-dihydronaphthalene-1,6-dione (2),1个香豆素类化合物5,7-二甲氧基-6-羟基香豆素(7),1个腺苷类化合物1,2,4-triazole-(1'R,2'R,3'R,4'R)-nucleosi des (9).上述化合物中,化合物1和3为两个新骨架化合物。
体外评价结果显示：上述化合物对HCT-8、Bel-7402、BGC-823、A549、A2780、MCF-7六株肿瘤细胞的增殖均无明显抑制作用。
Plant endophytic fungus is an important source of natural active compounds. An endophytic fungus F-31 (identified as Periconia sp.) derived from Annona muricata L which can inhibit proliferation of several tumor cells was selected for the chemical investigation.
Six new compounds, (4S,5R,9S,11S,12S)-Periconone A (1), 7-Hydroxy-11β,12α-dimethyl-9,10-dihydronaphthalene-1,6-dione (2), (6S,9R,10R, 12R,16 R)-Periconone C (3), (-)-(1R,4S,6R,7R)-2-Caren-4,9-olide (4), (3S,6S, 7R,8S)-Periconone B (5),4-(3'-Hydroxybutyl)-4H-furan-l-one (11), along with five known compounds, Chloranthalactone E (6),5,7-Dimethyl-6-hydroxycoumarin (7), L-Tryptophan (8), 1,2,4-Triazole-(1'R,2'R,3'R,4'R)-nucleosides (9), L-Phenylalanine (10), were isolated from the ethyl-acetate extraction of broth and water-soluble fraction of mycelia by means of chromatographic techniques and identified by various spectroscopic methods.
The in vitro pharmalogical evaluation results displayed that the above compounds exhibited no inhibitory effects on the proliferation of six tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7).
应用硅胶柱色谱、薄层色谱、Sephadex LH-20凝胶柱色谱、正相及反相高效液相色谱等各种色谱手段对F-31发酵液的乙酸乙酯提取物和菌丝体的水层提取物分别进行了分离纯化,共得到11个化合物,并采用各种现代波谱技术对分离到的化合物进行了结构鉴定,其中6个化合物为新化合物。这些化合物包括：3个倍半萜类化合物(4S,5R,9S, 11S,12S)-Periconone A (1)、(3S,6S,7R,8S)-Periconone B (5)和Chloranthalactone E (6),1个二萜类化合物(6S,9R,10R,1 2R,16R)-Periconone C (3),1个单萜内酯(-)-(1R,4S,6R,7R)-2-Caren-4,9-olide (4),1个内酯类化合物4-(3'-Hydroxybutyl)-4H-furan-1-one (11),2个氨基酸类化合物L-色氨酸(8)和L-苯丙氨酸(10),1个醌类化合物7-hydroxy-11β,12α-di methyl-9,10-dihydronaphthalene-1,6-dione (2),1个香豆素类化合物5,7-二甲氧基-6-羟基香豆素(7),1个腺苷类化合物1,2,4-triazole-(1'R,2'R,3'R,4'R)-nucleosi des (9).上述化合物中,化合物1和3为两个新骨架化合物。
体外评价结果显示：上述化合物对HCT-8、Bel-7402、BGC-823、A549、A2780、MCF-7六株肿瘤细胞的增殖均无明显抑制作用。
Plant endophytic fungus is an important source of natural active compounds. An endophytic fungus F-31 (identified as Periconia sp.) derived from Annona muricata L which can inhibit proliferation of several tumor cells was selected for the chemical investigation.
Six new compounds, (4S,5R,9S,11S,12S)-Periconone A (1), 7-Hydroxy-11β,12α-dimethyl-9,10-dihydronaphthalene-1,6-dione (2), (6S,9R,10R, 12R,16 R)-Periconone C (3), (-)-(1R,4S,6R,7R)-2-Caren-4,9-olide (4), (3S,6S, 7R,8S)-Periconone B (5),4-(3'-Hydroxybutyl)-4H-furan-l-one (11), along with five known compounds, Chloranthalactone E (6),5,7-Dimethyl-6-hydroxycoumarin (7), L-Tryptophan (8), 1,2,4-Triazole-(1'R,2'R,3'R,4'R)-nucleosides (9), L-Phenylalanine (10), were isolated from the ethyl-acetate extraction of broth and water-soluble fraction of mycelia by means of chromatographic techniques and identified by various spectroscopic methods.
The in vitro pharmalogical evaluation results displayed that the above compounds exhibited no inhibitory effects on the proliferation of six tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7).
引文
1 J. K. Stone, C.W. Bacon and J. F.White, in An Overview of Endophytic Microbes: Endophytism Defined, ed. C. W. Bacon and J. F. White, Jr.,M. Dekker, Inc., New York,2000, pp:3-5
2 R. X. Tan and W. X. Zou. Endophytes:a rich source of functional metabolites. Nat. Prod. Rep., 2001,18,448-459
3 G. Ding, Y. C. Song, J. R. Chen, H. M. Ge, X. T. Wang and R. X. Tan. Chaetoglobosin U, a Cytochalasan Alkaloid from Endophytic Chaetomium g-lobosum IFB-E019. J. Nat. Prod., 2006,69,302-304
4 H. Lu, W. X. Zou, J. C. Meng, J. Hu and R. X. Tan. New bioactive metabolites produced by Colletotrichum sp., an endophytic fungus in Artemisia annual. Plant Sci.,2000,151(1),67-73
5 C. L. Schardl and T. D. Phillips. Protective grass endophytes. Plant Dis.,1997,81,430-438
6 D. D. Rowan and G. C. M. Latch, in Biotechnology of endophytic fungi of grasses, eds. C. W. Bacon and J. F. White, Jr., CRC Press, Boca Raton,1994, pp:169-183
7 C. K. A. Gurney and P. G. Mantle. Biosynthesis of 1-N-methylalbonoursin by an Endophytic Streptomyces sp. Isolated from Perennial Ryegrass. J. Nat. Prod.,1993,56,1194-1198
8 J. Y. Li, G. Strobel, J. Harper, E. Lobkovsky and J. Clardy. Cryptocin, a Potent Tetramic Acid Antimycotic from the Endophytic Fungus Cryptosporiopsis cf. quercina. Org. Lett.,2000,23, 767-770
9 B. T. Larson, M. D. Samford, J. M. Camden, E. L. Piper, M. S. Kerley, J. A. Peterson and J. T. Turner. Ergovaline Binding and Activation of D2 Dopamine Receptors in GH(4)ZR(7) Cells. J. Animal Sci.,1995,73,1396-1400
10 J. R. Strickland, E. M. Bailey, L. K. Abney and J. W. Oliver. Assessment of The Mitogenic Potential of The Alkaloids Produced by Endophyte(Acremonium Coenophialum)-Infected Tall Fescue (Festuca Arundinacea) on Bovine Vascular Smoothmuscle in Vitro. J. Animal Sci.,1996,74,1664-1671
11 V. Rukachaisirikul, C. Tansakul, S. Saithong, C. Pakawatchai, M. Isaka, and R. Suvannakad. Hirsutane Sesquiterpenes from the Fungus Lentinus conatus BCC 8996. J. Nat. Prod.,2005, 68,1674-1676
12 K. Krohn, J. Dai, U. Florke, H. J. Aust, S. Drager and B. Schulz. Botryane Metabolites from the Fungus Geniculosporium sp. Isolated from the Marine Red Alga Polysiphonia. J. Nat. Prod.,2005,68,400-405
13 K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, P. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan and E. J. Sorensen. Total Synthesis of Taxol. Nature,1994,367,630-634
14 S. F. Brady, M. P. Singh, J. E. Janso and J. Clardy. Guanacastepene, a Fungal-derived Diterpene Antibiotic with a New Carbon Skeleton. J. Am. Chem. Soc.,2000,122,2116-2117
15 S. F. Brady, S. M. Bondi and J. Clardy. The Guanacastepenes:A Highly Diverse Family of Secondary Metabolites Produced by an Endophytic Fungus. J. Am. Chem. Soc.,2001,123, 9900-9901
16 J. C. Lee, E. Lobkovsky, N. B. Pliam, G. A. Strobel and J. Clardy. Subglutinols A and B: Immunosuppressive compounds from the endophytic fungus Fusarium subglutinans. J. Org. Chem.,1995,60,7076-7077
17 T. Akihisa, M. Tagata, M. Ukiya, H. Tokuda, T. Suzuki and Y. Kimura. Oxygenated Lanostane-Type Triterpenoids from the Fungus Ganoderma lucidum. J. Nat. Prod.,2005,68, 559-563
18 J. Y. Li and G. A. Strobel. Jesterone and hydroxy-jesterone antioomycete cyclohexenone epoxides from the endophytic fungus Pestalotiopsis jesteri. Phytochemistry,2001,57, 261-265
19 J. Y. Li, J. K. Harper, D. M. Grant, B. O. Tombe, B. Bashyal, W. M. Hess and G. A. Strobel. Ambuic acid, a highly functionalized cyclohexenone with antifungal activity from Pestalotiopsis spp. and Monochaetia sp. Phytochemistry,2001,56,463-468
20 S. B. Singh, D. L. Zink, Z. Guan, J. Collado, F. Pelaez, P. J. Felock and D. J. Hazuda. Isolation, Structure and HIV-1 Integrase Inhibitory Activity of Xanthoviridicatin E and F, Two Novel Fungal Metabolites Produced by Penicillium chrysogenum. Helv. Chim. Acta., 2003,86,3380-3385
21 H. M. Ge, Y. C. Song, C. Y. Shan, Y. H. Ye and R. X. Tan. New and cytotoxic anthraquinones from Pleospora sp. IFB-E006, an endophytic fungus in Imperata cylindrical. Planta Med.,2005,71,1063-1065
22 M. L. Sergio, D. T. Gina, D. C. Phyllis, A. K. Thomas, H. G. William and C. R. Luis. Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp. J. Nat. Prod., 2008,71,2011-2014
23 Y. Ju, J. N. Sacalis and C. C. Still. Bioactive Flavonoids from Endophyte-Infected Blue Grass (Poa ampla). J. Agric. Food. Chem.,1998,46,3785-3788
24 L. Du, T. J. Zhu, H. B. Liu, Y. C. Fang, W. M. Zhu and Q. Q. Gu. Cytotoxic Polyketides from a Marine-derived Fungus Aspergillus glaucus. J. Nat. Prod.,2008,71,1837-1842
25 R. K. Phipps, B. O. Petersen, K. B. Christensen, J. Duus, J. C. Frisvad and T. O. Larsen. Hesseltin A, a Novel Antiviral Metabolite from Penicillium hesseltinei. Org. Lett.,2004, 6(20),3441-3443
26 P. Kongsaeree, S. Prabpai, N. Sriubolmas, C. Vongvein and S. Wiyakrutta, Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides. J. Nat. Prod.,2003,66,709-711
27 R. Sappapan, D. Sommit, N. Ngamrojanavanich, S. Pengpreecha, S. Wiyakrutta, N. Sriubolmas and K. Pudhom.11-Hydroxymonocerin from the Plant Endophyic Fungus Exserohilum rostratum. J. Nat. Prod.,2008,71,1657-1659
28 B. Schulz, J. Sucker, H. J. Aust, K. Krohn, K. Ludewig, P. G. Jones and D. Doring. Biologically active secondary metabolites of endophytic Pezicula species. Mycol Res.,1995, 99,1007-1015
29 W. Zhang, K. Krohn, S. Draeger and B. Schulz. Bioactive Isocoumarins Isolated from the Endophytic Fungus Microdochium bolleyi. J. Nat. Prod.,2008,71,1078-1081
30 G. Strobel, E. Ford, J. Worapong, J. K. Harper, A. M. Arif, A. M. Grant, P. C. W. Fung and R. M. W. W. Chau. Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. Phytochemistry,2002,60,179-183
31 J. K. Harper, A. M. Arif, E. J. Ford, G. A. Strobel, J. A. Porco, Jr., D. P. Tomer, K. L. Oneill, E. M. Heider and D. M. Grant. Pestacin:a 1,3-dihydro-isobenzofuran from Pestalotiopsis microspora possessing antioxidant and antimycotic activities. Tetrahedron,2003,59, 2471-2476
32 B. P. Bashyal, E. M. K. Wijeratne, S. H. Faeth and A. A. L. Gunatilaka. Globosumones A-C, Cytotoxic Orsellinic Acid Esters from the Sonoran Desert Endophytic Fungus Chaetomium globosum. J. Nat. Prod.,2005,68,724-728
33 W. X. Zou, J. C. Meng, H. Lu, G. X. Chen, G. X. Shi, T. Y. Zhang and R. X. Tan. Metabolites of Colletotrichum gloeosporioides, an Endophytic Fungus in Artemisia mongolica. J. Nat. Prod.,2000,63,1529-1530
34 B. Guo, J. R. Dai, S. Ng, Y. Huang, C. Leong, W. Ong and B. K. Karte. Cytonic Acids A and B:Novel Tridepside Inhibitors of hCMV Protease from the Endophytic Fungus Cytonaema Species. J. Nat. Prod.,2000,63,602-604
35 B. Kopcke, M. Johansson, O. Stener and H. Anke. Biologically Active Secondary Metabolites from the Ascomycete A111-951 Production, Isolation and Biological Activities. J. Antibiot.,2002,55,36-40
36 M. Johansson, B. Kopcke, H. Anke and O. Stener. Biologically Active Secondary Metabolites. J. Antibiot.,2002,55,104-106
37 D. Weber, O. Stener, T. Anke, S. Gorzalczancy, V. Martino and C. Acevedo. Phomol, a new anti-inflammatory metabolite from an endophyte of the medicinal plant Erythrina crista-galli. J. Antibiot.,2004,57,559-563
38 A. S. Ratnayake, W. Y. Yoshida, S. L. Mooberry and T. Hemscheidt. TheStructure of Microcarpalide, a Microfilament Disrupting Agent from an Endophytic Fungus. Org. Lett., 2001,3,3479-3481
39 G. Y. Chen, Y. C. Lin, L. Wen, L. L. P. Vrijmoed and E. B. G. Jones. Two new metabolites of a marine endophytic fungus (No.1893) from an estuarine mangrove on the South China Sea coast. Tetrahedron,2003,59,4907-4909
40 D. B. Stierle, A. A. Stierle and T. Bugni. Sequoiamonascins A-D:Novel Anticancer Metabolites Isolated from a Redwood Endophyte. J. Org. Chem.,2003,68,4966-4969
41 T. Tanahashi, M. Kuroishi, A. Kuwahara, N. Nagakura and N. Hamada. For Phenolics from the Cultured Lichen Mycobiont of Graphis scripta var. pulverulenta. Chem. Pharm. Bull., 1997,45,1183-1185
42 T. Tanahashi, Y. Takenaka, N. Nagakura and N. Hamada.6H-Dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis sp.and their biosynthetic origin. Phytochemistry,2003,62,71-75
43 I. Rizzo, E. Varsavky, M. Haidukowski and H. Frade. Macrocyclic trichothecenes in Baccharis coridifolia plants and endophytes and Baccharis artemisioides plants. Toxicon, 1997,35,753-757
44 L. Shen, R. H. Jiao, Y. H. Ye, X. T. Wang, C. Xu, Y. C. Song, H. L. Zhu and R. X. Tan. Absolute configuration of new cytotoxic and other bioactive trichothecene macrolides. Chem. Eur.J.,2006,12,5596-5602
45 G. A. Strobel, R. V. Miller, C. M. Miller, M. M. Condron, D. B. Teplow and W. M. Hess. Cryptocandin, a potent antimycotic from the endophytic fungus Cryptosporiopsis cf. quercina. Microbiology,1999,145,1919-1926
46 G. A. Strobel and W. M. Hess. Glucosylation of the peptide leucinostatin A, produced by an endophytic fungus of European yew, may protect the host from leucinostatin toxicity. Chem. Biol.,1997,4,529-536
47 A. Stierle, D. Stierle and T. Bugni. Sequoiatones A and B:Novel Antitumor Metabolites Isolated from a Redwood Endophyte. J. Org. Chem.,1999,64,5479-5484
48彭小伟、陈有为等,黄花夹竹桃内生真菌产细胞松弛素的研究.中草药,2006,37(3),43-345
49 G. Ding, S. C. Liu, L. D. Guo, Y. G. Zhou and Y. S. Che. Antifungal Metabolites from the Plant Endophytic Fungus Pestalotiopsis foedan. J. Nat. Prod.,2008,71,615-618
50 Z. Y. Lu, Z. J. Lin, W. L. Wang, L. Du, T. J. Zhu, Y. C. Fang, Q. Q. Gu, and W. M. Zhu. Citrinin Dimers from the Halotolerant Fungus Penicillium citrinum B-57. J. Nat. Prod.,2008, 71,543-546
1 H. B. Kagan. Stereochemistry Fundamentals and Methods. Volume 2:Determination of Configurations by Dipole Moments, CD or ORD.1977 pp:123-125
2 H. B. Kagan. Stereochemistry Fundamentals and Methods. Volume 2:Determination of Configurations by Dipole Moments, CD or ORD.1977 pp:135-137
3 叶秀林编著.立体化学.北京大学出版社,北京,1999,pp：259-260.
4 D. D. Mass, M. Blagg and D. F. Wiemer. Synthesis and Reactions of (-)-and (+)-Carenones. J. Org.Chem.1984,49,853-856
5 A. Deagostino, P. B. Tivola, C. Prandi and P. Venturello. Lithium-potassium superbases as key reagents for the base-catalysed isomerisation of some terpenoids. J. Chem. Soc., Perkin Trans.1,2001,2856-60
6 L. D. Bari, G. Pescitelli, C. Pratelli, D. Pini and P. Salvadori. Determination of Absolute Configuration of Acyclic 1,2-Diols with Mo2(OAc)4.1. Snatzke's Method Revisited. J. Org. Chem.2001,66,4819-4825
7 M. Uchida, Y. Koike, G. Kusano, Y. Kondo, S. Nozoe, C. Kabuto and T. Takemoto. Studies on the Constituents of Chloranthus spp.Ⅲ. Six Sesquiterpenes from Chloranthus Japonicus. Chem. Pharm. Bull.,1980,28(1),92-102
8 H. B. Hu, Y. F. Jian, H. Cao and X. D. Zheng. Phenolic Compounds from Elsholtzia bodinieri Van't. J. Chin. Chem. Soc.,2007,54,1189-1194
9 X. J. Yan, M. Suzuki, M. O. Kameyama, Y. Sada, T. Nakanishi and T. Nagata. Extraction and Identification of Antioxidants in the Roots of Yacon (Smallanthus sonchifolius). J. Agric. Food. Chem.,1999,47,4711-4713
10 A. K. Drabikowska, L. Dudycz, D. Shugar. Studies on the mechanism of antiviral action of 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (ribavirin). J. Med. Chem.,1979,22(6), 653-657
11 M. Ichiro, O. Yukihiro, S. Isao, T. Jiro. Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines. Tetrahedron Lett., 1985,26(20),2449-2452
2 R. X. Tan and W. X. Zou. Endophytes:a rich source of functional metabolites. Nat. Prod. Rep., 2001,18,448-459
3 G. Ding, Y. C. Song, J. R. Chen, H. M. Ge, X. T. Wang and R. X. Tan. Chaetoglobosin U, a Cytochalasan Alkaloid from Endophytic Chaetomium g-lobosum IFB-E019. J. Nat. Prod., 2006,69,302-304
4 H. Lu, W. X. Zou, J. C. Meng, J. Hu and R. X. Tan. New bioactive metabolites produced by Colletotrichum sp., an endophytic fungus in Artemisia annual. Plant Sci.,2000,151(1),67-73
5 C. L. Schardl and T. D. Phillips. Protective grass endophytes. Plant Dis.,1997,81,430-438
6 D. D. Rowan and G. C. M. Latch, in Biotechnology of endophytic fungi of grasses, eds. C. W. Bacon and J. F. White, Jr., CRC Press, Boca Raton,1994, pp:169-183
7 C. K. A. Gurney and P. G. Mantle. Biosynthesis of 1-N-methylalbonoursin by an Endophytic Streptomyces sp. Isolated from Perennial Ryegrass. J. Nat. Prod.,1993,56,1194-1198
8 J. Y. Li, G. Strobel, J. Harper, E. Lobkovsky and J. Clardy. Cryptocin, a Potent Tetramic Acid Antimycotic from the Endophytic Fungus Cryptosporiopsis cf. quercina. Org. Lett.,2000,23, 767-770
9 B. T. Larson, M. D. Samford, J. M. Camden, E. L. Piper, M. S. Kerley, J. A. Peterson and J. T. Turner. Ergovaline Binding and Activation of D2 Dopamine Receptors in GH(4)ZR(7) Cells. J. Animal Sci.,1995,73,1396-1400
10 J. R. Strickland, E. M. Bailey, L. K. Abney and J. W. Oliver. Assessment of The Mitogenic Potential of The Alkaloids Produced by Endophyte(Acremonium Coenophialum)-Infected Tall Fescue (Festuca Arundinacea) on Bovine Vascular Smoothmuscle in Vitro. J. Animal Sci.,1996,74,1664-1671
11 V. Rukachaisirikul, C. Tansakul, S. Saithong, C. Pakawatchai, M. Isaka, and R. Suvannakad. Hirsutane Sesquiterpenes from the Fungus Lentinus conatus BCC 8996. J. Nat. Prod.,2005, 68,1674-1676
12 K. Krohn, J. Dai, U. Florke, H. J. Aust, S. Drager and B. Schulz. Botryane Metabolites from the Fungus Geniculosporium sp. Isolated from the Marine Red Alga Polysiphonia. J. Nat. Prod.,2005,68,400-405
13 K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, P. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan and E. J. Sorensen. Total Synthesis of Taxol. Nature,1994,367,630-634
14 S. F. Brady, M. P. Singh, J. E. Janso and J. Clardy. Guanacastepene, a Fungal-derived Diterpene Antibiotic with a New Carbon Skeleton. J. Am. Chem. Soc.,2000,122,2116-2117
15 S. F. Brady, S. M. Bondi and J. Clardy. The Guanacastepenes:A Highly Diverse Family of Secondary Metabolites Produced by an Endophytic Fungus. J. Am. Chem. Soc.,2001,123, 9900-9901
16 J. C. Lee, E. Lobkovsky, N. B. Pliam, G. A. Strobel and J. Clardy. Subglutinols A and B: Immunosuppressive compounds from the endophytic fungus Fusarium subglutinans. J. Org. Chem.,1995,60,7076-7077
17 T. Akihisa, M. Tagata, M. Ukiya, H. Tokuda, T. Suzuki and Y. Kimura. Oxygenated Lanostane-Type Triterpenoids from the Fungus Ganoderma lucidum. J. Nat. Prod.,2005,68, 559-563
18 J. Y. Li and G. A. Strobel. Jesterone and hydroxy-jesterone antioomycete cyclohexenone epoxides from the endophytic fungus Pestalotiopsis jesteri. Phytochemistry,2001,57, 261-265
19 J. Y. Li, J. K. Harper, D. M. Grant, B. O. Tombe, B. Bashyal, W. M. Hess and G. A. Strobel. Ambuic acid, a highly functionalized cyclohexenone with antifungal activity from Pestalotiopsis spp. and Monochaetia sp. Phytochemistry,2001,56,463-468
20 S. B. Singh, D. L. Zink, Z. Guan, J. Collado, F. Pelaez, P. J. Felock and D. J. Hazuda. Isolation, Structure and HIV-1 Integrase Inhibitory Activity of Xanthoviridicatin E and F, Two Novel Fungal Metabolites Produced by Penicillium chrysogenum. Helv. Chim. Acta., 2003,86,3380-3385
21 H. M. Ge, Y. C. Song, C. Y. Shan, Y. H. Ye and R. X. Tan. New and cytotoxic anthraquinones from Pleospora sp. IFB-E006, an endophytic fungus in Imperata cylindrical. Planta Med.,2005,71,1063-1065
22 M. L. Sergio, D. T. Gina, D. C. Phyllis, A. K. Thomas, H. G. William and C. R. Luis. Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp. J. Nat. Prod., 2008,71,2011-2014
23 Y. Ju, J. N. Sacalis and C. C. Still. Bioactive Flavonoids from Endophyte-Infected Blue Grass (Poa ampla). J. Agric. Food. Chem.,1998,46,3785-3788
24 L. Du, T. J. Zhu, H. B. Liu, Y. C. Fang, W. M. Zhu and Q. Q. Gu. Cytotoxic Polyketides from a Marine-derived Fungus Aspergillus glaucus. J. Nat. Prod.,2008,71,1837-1842
25 R. K. Phipps, B. O. Petersen, K. B. Christensen, J. Duus, J. C. Frisvad and T. O. Larsen. Hesseltin A, a Novel Antiviral Metabolite from Penicillium hesseltinei. Org. Lett.,2004, 6(20),3441-3443
26 P. Kongsaeree, S. Prabpai, N. Sriubolmas, C. Vongvein and S. Wiyakrutta, Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides. J. Nat. Prod.,2003,66,709-711
27 R. Sappapan, D. Sommit, N. Ngamrojanavanich, S. Pengpreecha, S. Wiyakrutta, N. Sriubolmas and K. Pudhom.11-Hydroxymonocerin from the Plant Endophyic Fungus Exserohilum rostratum. J. Nat. Prod.,2008,71,1657-1659
28 B. Schulz, J. Sucker, H. J. Aust, K. Krohn, K. Ludewig, P. G. Jones and D. Doring. Biologically active secondary metabolites of endophytic Pezicula species. Mycol Res.,1995, 99,1007-1015
29 W. Zhang, K. Krohn, S. Draeger and B. Schulz. Bioactive Isocoumarins Isolated from the Endophytic Fungus Microdochium bolleyi. J. Nat. Prod.,2008,71,1078-1081
30 G. Strobel, E. Ford, J. Worapong, J. K. Harper, A. M. Arif, A. M. Grant, P. C. W. Fung and R. M. W. W. Chau. Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. Phytochemistry,2002,60,179-183
31 J. K. Harper, A. M. Arif, E. J. Ford, G. A. Strobel, J. A. Porco, Jr., D. P. Tomer, K. L. Oneill, E. M. Heider and D. M. Grant. Pestacin:a 1,3-dihydro-isobenzofuran from Pestalotiopsis microspora possessing antioxidant and antimycotic activities. Tetrahedron,2003,59, 2471-2476
32 B. P. Bashyal, E. M. K. Wijeratne, S. H. Faeth and A. A. L. Gunatilaka. Globosumones A-C, Cytotoxic Orsellinic Acid Esters from the Sonoran Desert Endophytic Fungus Chaetomium globosum. J. Nat. Prod.,2005,68,724-728
33 W. X. Zou, J. C. Meng, H. Lu, G. X. Chen, G. X. Shi, T. Y. Zhang and R. X. Tan. Metabolites of Colletotrichum gloeosporioides, an Endophytic Fungus in Artemisia mongolica. J. Nat. Prod.,2000,63,1529-1530
34 B. Guo, J. R. Dai, S. Ng, Y. Huang, C. Leong, W. Ong and B. K. Karte. Cytonic Acids A and B:Novel Tridepside Inhibitors of hCMV Protease from the Endophytic Fungus Cytonaema Species. J. Nat. Prod.,2000,63,602-604
35 B. Kopcke, M. Johansson, O. Stener and H. Anke. Biologically Active Secondary Metabolites from the Ascomycete A111-951 Production, Isolation and Biological Activities. J. Antibiot.,2002,55,36-40
36 M. Johansson, B. Kopcke, H. Anke and O. Stener. Biologically Active Secondary Metabolites. J. Antibiot.,2002,55,104-106
37 D. Weber, O. Stener, T. Anke, S. Gorzalczancy, V. Martino and C. Acevedo. Phomol, a new anti-inflammatory metabolite from an endophyte of the medicinal plant Erythrina crista-galli. J. Antibiot.,2004,57,559-563
38 A. S. Ratnayake, W. Y. Yoshida, S. L. Mooberry and T. Hemscheidt. TheStructure of Microcarpalide, a Microfilament Disrupting Agent from an Endophytic Fungus. Org. Lett., 2001,3,3479-3481
39 G. Y. Chen, Y. C. Lin, L. Wen, L. L. P. Vrijmoed and E. B. G. Jones. Two new metabolites of a marine endophytic fungus (No.1893) from an estuarine mangrove on the South China Sea coast. Tetrahedron,2003,59,4907-4909
40 D. B. Stierle, A. A. Stierle and T. Bugni. Sequoiamonascins A-D:Novel Anticancer Metabolites Isolated from a Redwood Endophyte. J. Org. Chem.,2003,68,4966-4969
41 T. Tanahashi, M. Kuroishi, A. Kuwahara, N. Nagakura and N. Hamada. For Phenolics from the Cultured Lichen Mycobiont of Graphis scripta var. pulverulenta. Chem. Pharm. Bull., 1997,45,1183-1185
42 T. Tanahashi, Y. Takenaka, N. Nagakura and N. Hamada.6H-Dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis sp.and their biosynthetic origin. Phytochemistry,2003,62,71-75
43 I. Rizzo, E. Varsavky, M. Haidukowski and H. Frade. Macrocyclic trichothecenes in Baccharis coridifolia plants and endophytes and Baccharis artemisioides plants. Toxicon, 1997,35,753-757
44 L. Shen, R. H. Jiao, Y. H. Ye, X. T. Wang, C. Xu, Y. C. Song, H. L. Zhu and R. X. Tan. Absolute configuration of new cytotoxic and other bioactive trichothecene macrolides. Chem. Eur.J.,2006,12,5596-5602
45 G. A. Strobel, R. V. Miller, C. M. Miller, M. M. Condron, D. B. Teplow and W. M. Hess. Cryptocandin, a potent antimycotic from the endophytic fungus Cryptosporiopsis cf. quercina. Microbiology,1999,145,1919-1926
46 G. A. Strobel and W. M. Hess. Glucosylation of the peptide leucinostatin A, produced by an endophytic fungus of European yew, may protect the host from leucinostatin toxicity. Chem. Biol.,1997,4,529-536
47 A. Stierle, D. Stierle and T. Bugni. Sequoiatones A and B:Novel Antitumor Metabolites Isolated from a Redwood Endophyte. J. Org. Chem.,1999,64,5479-5484
48彭小伟、陈有为等,黄花夹竹桃内生真菌产细胞松弛素的研究.中草药,2006,37(3),43-345
49 G. Ding, S. C. Liu, L. D. Guo, Y. G. Zhou and Y. S. Che. Antifungal Metabolites from the Plant Endophytic Fungus Pestalotiopsis foedan. J. Nat. Prod.,2008,71,615-618
50 Z. Y. Lu, Z. J. Lin, W. L. Wang, L. Du, T. J. Zhu, Y. C. Fang, Q. Q. Gu, and W. M. Zhu. Citrinin Dimers from the Halotolerant Fungus Penicillium citrinum B-57. J. Nat. Prod.,2008, 71,543-546
1 H. B. Kagan. Stereochemistry Fundamentals and Methods. Volume 2:Determination of Configurations by Dipole Moments, CD or ORD.1977 pp:123-125
2 H. B. Kagan. Stereochemistry Fundamentals and Methods. Volume 2:Determination of Configurations by Dipole Moments, CD or ORD.1977 pp:135-137
3 叶秀林编著.立体化学.北京大学出版社,北京,1999,pp：259-260.
4 D. D. Mass, M. Blagg and D. F. Wiemer. Synthesis and Reactions of (-)-and (+)-Carenones. J. Org.Chem.1984,49,853-856
5 A. Deagostino, P. B. Tivola, C. Prandi and P. Venturello. Lithium-potassium superbases as key reagents for the base-catalysed isomerisation of some terpenoids. J. Chem. Soc., Perkin Trans.1,2001,2856-60
6 L. D. Bari, G. Pescitelli, C. Pratelli, D. Pini and P. Salvadori. Determination of Absolute Configuration of Acyclic 1,2-Diols with Mo2(OAc)4.1. Snatzke's Method Revisited. J. Org. Chem.2001,66,4819-4825
7 M. Uchida, Y. Koike, G. Kusano, Y. Kondo, S. Nozoe, C. Kabuto and T. Takemoto. Studies on the Constituents of Chloranthus spp.Ⅲ. Six Sesquiterpenes from Chloranthus Japonicus. Chem. Pharm. Bull.,1980,28(1),92-102
8 H. B. Hu, Y. F. Jian, H. Cao and X. D. Zheng. Phenolic Compounds from Elsholtzia bodinieri Van't. J. Chin. Chem. Soc.,2007,54,1189-1194
9 X. J. Yan, M. Suzuki, M. O. Kameyama, Y. Sada, T. Nakanishi and T. Nagata. Extraction and Identification of Antioxidants in the Roots of Yacon (Smallanthus sonchifolius). J. Agric. Food. Chem.,1999,47,4711-4713
10 A. K. Drabikowska, L. Dudycz, D. Shugar. Studies on the mechanism of antiviral action of 1-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (ribavirin). J. Med. Chem.,1979,22(6), 653-657
11 M. Ichiro, O. Yukihiro, S. Isao, T. Jiro. Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines. Tetrahedron Lett., 1985,26(20),2449-2452