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Volumn 11, Issue 6, 2009, Pages 1241-1244

Protostadienol biosynthesis and metabolism in the pathogenic fungus Aspergillus fumigatus

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DRUG DERIVATIVE; FUSIDIC ACID; HELVOLIC ACID; LANOSTEROL SYNTHASE; MUTASE; PROTOSTA 13(17),24 DIEN 3BETA OL; PROTOSTA-13(17),24-DIEN-3BETA-OL; TRITERPENE;

EID: 64049095850     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802696a     Document Type: Article
Times cited : (51)

References (45)
  • 4
    • 43249118838 scopus 로고    scopus 로고
    • Fedorova, N. D.; et al. PLoS Genet. 2008, 4, e1000046
    • (b) Fedorova, N. D.; et al. PLoS Genet. 2008, 4, e1000046
  • 5
    • 64349098532 scopus 로고    scopus 로고
    • see Supporting Information for full reference
    • (see Supporting Information for full reference).
  • 6
    • 53049108022 scopus 로고    scopus 로고
    • e1000154 see Supporting Information for full reference
    • (c) McDonagh, A.; et al. PLoS Pathog. 2008, 4, e1000154 (see Supporting Information for full reference).
    • (2008) PLoS Pathog , vol.4
    • McDonagh, A.1
  • 11
    • 36349025257 scopus 로고    scopus 로고
    • (b) Abe, I. Nat. Prod. Rep. 2007, 24, 1311-1331.
    • (2007) Nat. Prod. Rep , vol.24 , pp. 1311-1331
    • Abe, I.1
  • 12
    • 64349085020 scopus 로고    scopus 로고
    • Meeting announcements by us and others: (a) Ivanova, Y. M.; Xiong, Q.; Matsuda, S. P. T. American Society of Pharmacognosy Annual Meeting, Arlington, VA, 2006; p P-013.
    • Meeting announcements by us and others: (a) Ivanova, Y. M.; Xiong, Q.; Matsuda, S. P. T. American Society of Pharmacognosy Annual Meeting, Arlington, VA, 2006; p P-013.
  • 13
    • 64349100042 scopus 로고    scopus 로고
    • Reference 5b, p 1329
    • (b) Reference 5b, p 1329.
  • 14
    • 28644434509 scopus 로고    scopus 로고
    • see Supporting Information for full reference
    • Nierman, W. C.; et al. Nature 2005, 438, 1151-1156 (see Supporting Information for full reference).
    • (2005) Nature , vol.438 , pp. 1151-1156
    • Nierman, W.C.1
  • 20
    • 64349092698 scopus 로고    scopus 로고
    • Fusidanes and Protostanes
    • Academic Press: Amsterdam, chapter 16, pp
    • Cole, R. J.; Schweikert, M. A. Handbook of Secondary Fungal Metabolites, Vol 2; Academic Press: Amsterdam, 2003; chapter 16, "Fusidanes and Protostanes", pp 461-492.
    • (2003) Handbook of Secondary Fungal Metabolites , vol.2 , pp. 461-492
    • Cole, R.J.1    Schweikert, M.A.2
  • 21
    • 64349094676 scopus 로고    scopus 로고
    • The NMR chemical shifts in Table 1 are consistent with partial 1H NMR data reported for 2 prepared synthetically from fusidic acid, von Daehne, W, Godtfredsen, W. O. U. S. Patent 6177418, 2001
    • (a) The NMR chemical shifts in Table 1 are consistent with partial 1H NMR data reported for 2 (prepared synthetically from fusidic acid) : von Daehne, W.; Godtfredsen, W. O. U. S. Patent 6177418, 2001.
  • 22
    • 0014485231 scopus 로고    scopus 로고
    • 2 and 3 were isolated from Cephalosporium caerulens (Sarocladium oryzae), and their structures were elucidated from chemical correlations and limited spectral characterization: Hattori, T.; Igarashi, H.; Iwasaki, S.; Okuda, S. Tetrahedron Lett. 1969, 1023-1026.
    • (b) 2 and 3 were isolated from Cephalosporium caerulens (Sarocladium oryzae), and their structures were elucidated from chemical correlations and limited spectral characterization: Hattori, T.; Igarashi, H.; Iwasaki, S.; Okuda, S. Tetrahedron Lett. 1969, 1023-1026.
  • 24
    • 32644440439 scopus 로고    scopus 로고
    • Because of metabolism by yeast, the true levels of lanosterol and parkeol formation may be an order of magnitude higher: Lodeiro, S.; Wilson, W. K.; Shan, H.; Matsuda, S. P. T. Org. Lett. 2006, 8, 439-442.
    • Because of metabolism by yeast, the true levels of lanosterol and parkeol formation may be an order of magnitude higher: Lodeiro, S.; Wilson, W. K.; Shan, H.; Matsuda, S. P. T. Org. Lett. 2006, 8, 439-442.
  • 29
    • 30144439471 scopus 로고    scopus 로고
    • This reference points out how earlier knowledge of the fusidane skeleton might have spared much confusion and controversy over the mechanism of triterpene biosynthesis
    • Eschenmoser, A.; Arigoni, D. Helv. Chim. Acta 2005, 88, 3011-3050. This reference points out how earlier knowledge of the fusidane skeleton might have spared much confusion and controversy over the mechanism of triterpene biosynthesis.
    • (2005) Helv. Chim. Acta , vol.88 , pp. 3011-3050
    • Eschenmoser, A.1    Arigoni, D.2
  • 34
    • 84869274898 scopus 로고    scopus 로고
    • An earlier 6-keto-7α-acetoxy structure of helvolic acid is given in ref 12 (p 491) and older papers, for example, ref 13b
    • An earlier 6-keto-7α-acetoxy structure of helvolic acid is given in ref 12 (p 491) and older papers, for example, ref 13b.
  • 35
    • 84869275932 scopus 로고    scopus 로고
    • 3c
    • 3c
  • 36
    • 44949164623 scopus 로고    scopus 로고
    • Helvolic acid was recently isolated from Me. anisopliae: Lee, S.-Y.; Kinoshita, H.; Ihara, F.; Igarashi, Y.; Nihira, T. J. Biosci. Bioeng. 2008, 105, 476-480.
    • Helvolic acid was recently isolated from Me. anisopliae: Lee, S.-Y.; Kinoshita, H.; Ihara, F.; Igarashi, Y.; Nihira, T. J. Biosci. Bioeng. 2008, 105, 476-480.
  • 37
    • 84869273580 scopus 로고    scopus 로고
    • 7 found no orthologs of any helvolic acid pathway genes in As. oryzae or As. nidulans.
    • 7 found no orthologs of any helvolic acid pathway genes in As. oryzae or As. nidulans.
  • 38
    • 64349108192 scopus 로고    scopus 로고
    • sequence was available only as ESTs, which lack synteny or intron data
    • (b) Me. anisopliae sequence was available only as ESTs, which lack synteny or intron data.
    • Me. anisopliae
  • 40
    • 42949174108 scopus 로고    scopus 로고
    • Fungi were originally rich in introns, which have been partially lost in some lineages and almost fully lost in the Saccharomycotina: Stajich, J. E.; Dietrich, F. S.; Roy, S. W. Genome Biol. 2007, 8, R223.
    • Fungi were originally rich in introns, which have been partially lost in some lineages and almost fully lost in the Saccharomycotina: Stajich, J. E.; Dietrich, F. S.; Roy, S. W. Genome Biol. 2007, 8, R223.
  • 41
    • 3042720475 scopus 로고    scopus 로고
    • see Supporting Information for full reference
    • (a) Dujon, B.; et al. Nature 2004, 430, 35-44 (see Supporting Information for full reference).
    • (2004) Nature , vol.430 , pp. 35-44
    • Dujon, B.1
  • 44
    • 64349120483 scopus 로고    scopus 로고
    • Also, barring HGT of an unknown bacterial PDS, H2 requires several recent instances of convergent evolution of fungal cyclases. Cycloartenol synthase of Stigmatella aurantiaca is a plausible HGT candidate (Figure 3B), although its GC content (68%) is elevated relative to PDSs (55-62%) ; see Table S10 (Supporting Information). Penicillin synthesis and likely recent HGTs of squalene cyclases in aspergilli provide precedent for H2.
    • Also, barring HGT of an unknown bacterial PDS, H2 requires several recent instances of convergent evolution of fungal cyclases. Cycloartenol synthase of Stigmatella aurantiaca is a plausible HGT candidate (Figure 3B), although its GC content (68%) is elevated relative to PDSs (55-62%) ; see Table S10 (Supporting Information). Penicillin synthesis and likely recent HGTs of squalene cyclases in aspergilli provide precedent for H2.
  • 45
    • 43749086015 scopus 로고    scopus 로고
    • Notably, nonenzymatic blocking of DNA methyl transferase and histone deacetylase can generate an abundance of otherwise silent secondary metabolites: Williams, R. B.; Henrikson, J. C.; Hoover, A. R.; Lee, A. E.; Cichewicz, R. H. Org. Biomol. Chem. 2008, 6, 1895-1897.
    • Notably, nonenzymatic blocking of DNA methyl transferase and histone deacetylase can generate an abundance of otherwise silent secondary metabolites: Williams, R. B.; Henrikson, J. C.; Hoover, A. R.; Lee, A. E.; Cichewicz, R. H. Org. Biomol. Chem. 2008, 6, 1895-1897.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.