Bioactive metabolites from the plant endophyte pestalotiopsis fici

Mycology

Volumn 2, Issue 1, 2011, Pages 37-45

  Liu, Ling ^a  

^a INSTITUTE OF MICROBIOLOGY   (China)

Author keywords

Anti hiv; Antimicrobial; Cytotoxic; Endophytic fungi; New secondary metabolites; Pestalotiopsis spp; Structure elucidation

Indexed keywords

FUNGI; HUMAN IMMUNODEFICIENCY VIRUS; PESTALOTIOPSIS;

EID: 79953113021     PISSN: 21501203     EISSN: 21501211     Source Type: Journal    
DOI: 10.1080/21501203.2011.562248     Document Type: Review

References (39)

1. Adeboya MO, Edwards RL, Lassøe T, Maitland DJ, Shields L, Whalley AJS. 1996. Metabolites of the higher fungi. Part 29. Maldoxin, maldoxone, dihydromaldoxin, isodihy-dromaldoxin and dechlorodihydromaldoxin. A spirocyclo-hexadienone, a depsidone and three diphenyl ethers: keys in the depsidone biosynthetic pathway from a member of the fungus genus Xylaria. J Chem Soc Perkin Trans. I: 1419-1425.
2. Aly AH, Debbab A, Kjer J, Proksch P. 2010. Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products. Fungal Divers. 41: 1-16.
3. Bode HB, Bethe B, Höfs R, Zeeck A. 2002. Big effects from small changes: possible ways to explore nature's chemical diversity. ChemBioChem. 3: 619-627.
4. Bringmann G, Gulder TAM, Reichert M, Gulder T. 2008. The online assignment of the absolute configuration of natural products: HPLC-CD in combination with quantum chemical CD calculations. Chirality 20: 628-642.
5. Ding G, Liu SC, Guo LD, Zhou YG, Che YS. 2008a. Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan. J Nat Prod. 71: 615-618.
6. Ding G, Jiang LH, Guo LD, Chen XL, Zhang H, Che YS. 2008b. Pestalazines and pestalomides, bioactive metabolites from the plant pathogenic fungus Pestalotiopsis theae. J Nat Prod. 71: 1861-1865.
7. Ding G, Li Y, Fu SB, Liu SC, Wei JC, Che YS. 2009a. Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp. J Nat Prod. 72: 182-186.
8. Ding G, Zheng ZH, Liu SC, Zhang H, Guo LD, Che YS. 2009b. Photinides A-F, cytotoxic benzofuranone-derived γ-lactones from the plant endophytic fungus Pestalotiopsis photiniae. J Nat Prod. 72: 942-945.
9. Ding G, Zhang F, Chen, H, Guo, LD, Zou, ZM, Che, YS. 2011. Pestaloquinols A and B, isoprenylated epoxyquinols from Petalotiopsis sp. J Nat Prod. In press
10. Grimme S, Neese F. 2007. Double-hybrid density functional theory for excited electronic states of molecules. J Chem Phys. 127: 154116-154118.
11. Harper JK, Arif AM, Ford EJ, Strobel GA, Jr. Porco JA, Tomer DP, O'Neill KL, Heider EM, Grant DM. 2003. Pestacin: a 1, 3-dihydro isobenzofuran from Pestalotiopsis microspora possessing antioxidant and antimycotic activities. Tetrahedron 59: 2471-2476.
12. Lee JC, Strobel GA, Lobkovsky E, Clardy J. 1996. Torreyanic acid: a selectively cytotoxic quinone dimer from the endo-phytic fungus Pestalotiopsis microspora. J Org Chem. 61: 3232-3233.
13. Li EW, Jiang LH, Guo LD, Zhang H, Che YS. 2008a. Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta. Bioorg Med Chem. 16: 7894-7899.
14. Li EW, Tian RR, Liu SC, Chen XL, Guo LD, Che YS. 2008b. Pestalotheols A-D, bioactive metabolites from the plant endo-phytic fungus Pestalotiopsis theae. J Nat Prod. 71: 664-668.
15. Li JY, Strobel GA. 2001. Jesterone and hydroxy-jesterone antioomycete cyclohexenone epoxides from the endophytic fungus Pestalotiopsis jesteri. Phytochemistry. 57: 261-265.
16. Liao CC, Peddinti PK. 2002. Masked o-benzoquinones in organic synthesis. Acc Chem Res. 35: 856-866.
17. Liao CC. 2005. Masked o-benzoquinone strategy in organic synthesis: short and efficient construction of cis-decalins and linear triquinanes from 2-methoxyphenols. Pure Appl Chem. 77: 1221-1234.
18. Liu L, Liu SC, Jiang LH, Chen XL, Guo LD, Che YS. 2008a. Chloropupukenananin, the first chlorinated pupukeanane derivative and its precursors from Pestalotiopsis fici. Org Lett. 10: 1397-1400.
19. Liu L, Tian RR, Liu SC, Chen XL, Guo LD, Che YS. 2008b. Pestaloficiols A-E, bioactive cyclopropane derivatives from the plant endophytic fungus Pestalotiopsis fici. Bioorg Med Chem. 16: 6021-6026.
20. Liu L, Li Y, Liu SC, Zheng ZH, Chen XL, Guo LD, Che YS. 2009a. Chloropestolide A, an antitumor metabolite with an unprecedented spiroketal skeleton from Pestalotiopsis fici. Org Lett. 11: 2836-2839.
21. Liu L, Liu SC, Chen XL, Guo LD, Che YS. 2009b. Pestalofones A-E, bioactive cyclohexanone derivatives from the plant endophytic fungus Pestalotiopsis fici. Bioorg Med Chem. 17: 606-613.
22. Liu L, Liu SC, Niu SB, Guo LD, Chen XL, Che YS. 2009c. Isoprenylated chromone derivatives from the plant endo-phytic fungus Pestalotiopsis fici. J Nat Prod. 72: 1482-1486.
23. Liu L, Niu SB, Lu XH, Chen XL, Zhang H, Guo L, Che YS. 2010. Unique metabolites of Pestalotiopsis fici suggest a biosynthetic hypothesis involving a Diels-Alder reaction and then mechanistic diversification. Chem Commun. 46: 460-462.
24. Liu, L, Bruhn, T, Guo, LD, Götz, DCG, Brun, B, Stich, A, Che, YS, Bringmann, G. 2011. Chloropukeanolides C-E, cyto-toxic pupukeanane chlorides with a spiroketal skeleton from Petalotiopsis fici. Chem Eur J. in press.
25. Ogawa, T, Ando, K, Aotani, Y, Shinoda, K, Tanaka, T, Tsukuda, E, Yoshida, M, Matsuda, Y. 1995. RES-1214-1 and-2, novel non-peptidic endothelin type A receptor antagonists produced by Pestalotiopsis sp. J Antibiot. 48: 1401-1406.
26. Sanson DR, Gracz H, Tempesta MS, Fukuda DS, Nakatsukasa WM, Sands TH, Baker PJ, Mynderse JS. 1991. A82775B and A82775C, novel metabolites of an unknown fungus of the order sphaeropsidales. Tetrahedron 47: 3633-3644.
27. Schäfer A, Horn H, Ahlrichs R. 1992. Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J Chem Phys. 97: 2571-2577.
28. Schulz B, Boyle C, Draeger S, Rommert AK, Krohn K. 2002. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res. 106: 996-1004.
29. Shimada A, Takahashi I, Kawano T, Kimura Y. 2001. Chloroisosulochrin, chloroisosulochrin dehydrate, and pestheic acid, plant growth regulators, produced by Pestalotiopsis theae. Z Naturforsch. 56B: 797-803.
30. Stocking EM, Williams RM. 2003. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew Chem Int Ed. 42: 3078-3115.
31. Strobel GA. 2003. Endophytes as sources of bioactive products. Microbes Infect. 5:535-544.
32. Strobel GA, Yang X, Sears J, Kramer R, Sidhu RS, Hess WM. 1996. Taxol from Pestalotiopsis microspora, an endo-phytic fungus of Taxus wallochiana. Microbiology 142: 435-440.
33. Strobel, GA, Hess, WM, Li, JY, Ford, E, Sears, J, Sidhu, RS, Summerell, B. 1997. Pestalotiopsis guepinii, a taxol-producing endophyte of the wollemi pine, Wollemia nobilis. Aust J Bot. 45: 1073-1082.
34. Strobel GA, Daisy B, Castillo U, Harper J. 2004. Natural products from endophytic microorganisms. J Nat Prod. 67: 257-268.
35. Suzuki T, Kobayashi S. 2010. Concise approach to pupukeanane skeleton: synthetic study of chloropupukeannanin. Org Lett. 12: 2920-2923.
36. Tan RX, Zou WX. 2001. Endophytes: a rich source of functional metabolites. Nat Prod Rep. 18: 448-459.
37. Xu J, Kjer J, Sendker J, Wray V, Guan HS, Edrada RA, Lin WH, Wu J, Proksch P. 2009a. Chromones from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. J Nat Prod. 72: 662-665.
38. Xu J, Kjer J, Sendker J, Wray V, Guan HS, Edrada RA, Muller WEG, Bayer M, Lin WH, Wu J, Proksch P. 2009b. Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp isolated from the Chinese mangrove plant Rhizophora mucronata. Bioorgan Med Chem. 17: 7362-7367.
39. Xu, J, Ebada, SS, Proksch, P. 2010. Pestalotiopsis a highly creative genus: chemistry and bioactivity of secondary metabolites. Fungal Divers. 44: 15-31.