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Volumn 72, Issue 4, 2007, Pages 1211-1217

Pseudoceratins A and B, antifungal bicyclic bromotyrosine-derived metabolites from the marine sponge Pseudoceratina purpurea

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC BROMOTYROSINE; FUNCTIONAL GROUPS; PSEUDOCERATINA PURPUREA;

EID: 33846974766     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062010+     Document Type: Article
Times cited : (27)

References (27)
  • 7
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    • Reference 6; pp 260-261
    • Reference 6; pp 260-261.
  • 8
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    • 5 but from the red alga: Fan, X.; Xu, N.-J.; Shi, J.-G. J. Nat. Prod. 2003, 66, 455-458.
    • 5 but from the red alga: Fan, X.; Xu, N.-J.; Shi, J.-G. J. Nat. Prod. 2003, 66, 455-458.
  • 9
    • 33846949228 scopus 로고    scopus 로고
    • Reference 6; p 199
    • Reference 6; p 199.
  • 12
    • 33846949581 scopus 로고    scopus 로고
    • A substructural search of either 2,5-dioxabicyclo[4.3.1]dec-3-ene or 2,5-dioxabicyclo[4.3.1]deca-3,7-diene through SciFinder Scholar afforded no hits.
    • A substructural search of either 2,5-dioxabicyclo[4.3.1]dec-3-ene or 2,5-dioxabicyclo[4.3.1]deca-3,7-diene through SciFinder Scholar afforded no hits.
  • 13
    • 0037351833 scopus 로고    scopus 로고
    • Carbon chemical shifts of inositols are between 67 and 75 ppm (ref 6; p 401), whereas the methine carbon in a cyclohexene ring attached to the oxygen atom of an oxime ether group resonated at 84 ppm in trichodermamides: Caro, E.; Starks, C. M.; Jensen, P. R.; Fenical, W.; Lobkovsky, E.; Clardy, J. J. Nat. Prod. 2003, 66, 423-426.
    • Carbon chemical shifts of inositols are between 67 and 75 ppm (ref 6; p 401), whereas the methine carbon in a cyclohexene ring attached to the oxygen atom of an oxime ether group resonated at 84 ppm in trichodermamides: Caro, E.; Starks, C. M.; Jensen, P. R.; Fenical, W.; Lobkovsky, E.; Clardy, J. J. Nat. Prod. 2003, 66, 423-426.
  • 14
    • 84970589329 scopus 로고    scopus 로고
    • Compounds with a similar substitution pattern were isolated from the marine sponge Aplysina laevis. The oxymethine carbons substituted by a hydroxyl group in the cyclohexenone ring resonated at 78.4 and 78.9 ppm. (Capon, R. J.; MacLeod, J. K. Aust. J. Chem. 1987, 40, 341-346.)
    • Compounds with a similar substitution pattern were isolated from the marine sponge Aplysina laevis. The oxymethine carbons substituted by a hydroxyl group in the cyclohexenone ring resonated at 78.4 and 78.9 ppm. (Capon, R. J.; MacLeod, J. K. Aust. J. Chem. 1987, 40, 341-346.)
  • 15
    • 0030062843 scopus 로고    scopus 로고
    • The carbon chemical shifts of the acetal carbons of 1,1 -dimethoxy-cyclohexane, 2-cyclohexene-1-one dimethyl acetal, and cyclohexanone ethylene acetal are 100.0, 97.6, and 109.0, respectively (Spectral Database for Organic Compounds: http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi (accessed September 2006)). The structurally related acetal carbon in botryoxanthin A resonated at 107 ppm (Okada, S.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett. 1996, 37, 1065-1068).
    • The carbon chemical shifts of the acetal carbons of 1,1 -dimethoxy-cyclohexane, 2-cyclohexene-1-one dimethyl acetal, and cyclohexanone ethylene acetal are 100.0, 97.6, and 109.0, respectively (Spectral Database for Organic Compounds: http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi (accessed September 2006)). The structurally related acetal carbon in botryoxanthin A resonated at 107 ppm (Okada, S.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett. 1996, 37, 1065-1068).
  • 16
    • 33846995326 scopus 로고    scopus 로고
    • 6 due to coupling with exchangeable protons.
    • 6 due to coupling with exchangeable protons.
  • 19
    • 33847000767 scopus 로고    scopus 로고
    • Pseudoceratin B (2) was contaminated by 10% of inseparable related compound, which has not been characterized.
    • Pseudoceratin B (2) was contaminated by 10% of inseparable related compound, which has not been characterized.
  • 20
    • 33846982099 scopus 로고    scopus 로고
    • Even though the purity of the compound 7 prepared from 2 was not high, the chemical shift and shape of diagnostic signals, especially the one at δ 3.26, matched with those of 5.
    • Even though the purity of the compound 7 prepared from 2 was not high, the chemical shift and shape of diagnostic signals, especially the one at δ 3.26, matched with those of 5.
  • 21
    • 33846956999 scopus 로고    scopus 로고
    • 13 is noteworthy.
    • 13 is noteworthy.
  • 23
    • 33748778222 scopus 로고    scopus 로고
    • An exception to this generalization has recently been reported, Itampolins are biogentically considered as derived from homodetic tripeptides: Sorek, H, Rudi, A, Aknin, M, Gaydou, E, Kashman, Y. Tetrahedron Lett. 2006, 47, 7237-7239
    • An exception to this generalization has recently been reported, Itampolins are biogentically considered as derived from homodetic tripeptides: Sorek, H.; Rudi, A.; Aknin, M.; Gaydou, E.; Kashman, Y. Tetrahedron Lett. 2006, 47, 7237-7239.
  • 25
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    • Several dimeric diterpenes from the plants of the genus Plectranthus (Matloubi-Moghadam, F.; Rüedi, P.; Eugster, C. H. Helv. Chim. Acta 1987, 70, 975-983 and references cited therein)
    • Several dimeric diterpenes from the plants of the genus Plectranthus (Matloubi-Moghadam, F.; Rüedi, P.; Eugster, C. H. Helv. Chim. Acta 1987, 70, 975-983 and references cited therein)
  • 26
    • 0031921115 scopus 로고    scopus 로고
    • and dimers of triterpene and tetraterpene from the green alga Botryococcus braunii (Okada, S.; Tonegawa, I.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Phytochemistry 1998, 47, 1111-1115) connected through a intermolecular spiroacetal ring have been reported.
    • and dimers of triterpene and tetraterpene from the green alga Botryococcus braunii (Okada, S.; Tonegawa, I.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Phytochemistry 1998, 47, 1111-1115) connected through a intermolecular spiroacetal ring have been reported.
  • 27
    • 21844517996 scopus 로고    scopus 로고
    • Peptides tethered by the related diamines have been synthesized: Zajaczkowski, I.; Stepinski, J.; Temeriusz, A.; Tam, S. W. Z. Naturforsch. B: Chem. Sci. 1995, 50, 1329-1334.
    • Peptides tethered by the related diamines have been synthesized: Zajaczkowski, I.; Stepinski, J.; Temeriusz, A.; Tam, S. W. Z. Naturforsch. B: Chem. Sci. 1995, 50, 1329-1334.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.