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Volumn 6, Issue 12, 2004, Pages 1951-1954

Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIN; PEDERIN; PSYMBERIN; UNCLASSIFIED DRUG;

EID: 3042706094     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049503q     Document Type: Article
Times cited : (168)

References (30)
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    • (b) Variabilin was identified by comparison to data in Faulkner, D. J. Tetrahedron Lett. 1973, 39, 3821-3822.
    • (1973) Tetrahedron Lett. , vol.39 , pp. 3821-3822
    • Faulkner, D.J.1
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    • 3042845090 scopus 로고    scopus 로고
    • note
    • 3, q).
  • 8
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    • Methylation of 1 was performed as described in Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478. Although we originally favored C1 as a possible substructure, we are grateful to an anonymous reviewer who noted the potential of phenols to undergo O-methylation (Toyohiko, A.; Terasawa, S.; Sudo, K.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3759-3760.).
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 1475-1478
    • Hashimoto, N.1    Aoyama, T.2    Shioiri, T.3
  • 9
    • 85010090220 scopus 로고
    • Methylation of 1 was performed as described in Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478. Although we originally favored C1 as a possible substructure, we are grateful to an anonymous reviewer who noted the potential of phenols to undergo O-methylation (Toyohiko, A.; Terasawa, S.; Sudo, K.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3759-3760.).
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 3759-3760
    • Toyohiko, A.1    Terasawa, S.2    Sudo, K.3    Shioiri, T.4
  • 10
    • 1242296319 scopus 로고    scopus 로고
    • The name has been retained because of its prior incorporation in the research at collaborating institutions
    • Shortly after the completion of this work we learned that iciniastatin A, possessing properties identical to those of psymberin (1) had been disclosed: Pettit, G. R.; Xu, J.-P.; Chapuis, J.-C.; Pettit, R. K.; Tackett, L. P.; Doubek, D. L.; Hooper, J. N. A.; Schmidt, J. M. J. Med. Chem. 2004, 47, 1149-1152. The name has been retained because of its prior incorporation in the research at collaborating institutions.
    • (2004) J. Med. Chem. , vol.47 , pp. 1149-1152
    • Pettit, G.R.1    Xu, J.-P.2    Chapuis, J.-C.3    Pettit, R.K.4    Tackett, L.P.5    Doubek, D.L.6    Hooper, J.N.A.7    Schmidt, J.M.8
  • 13
    • 3042851579 scopus 로고    scopus 로고
    • note
    • A different 7R* (same as position C-8 in psymberin, 1) configuration was proposed for irciniastatin A (see ref 5).
  • 16
    • 0034571687 scopus 로고    scopus 로고
    • Mulzer, J., Bohlmann, R., Eds.; Ernst Schering Research Foundation Workshop 32; Springer: New York, (b) See also Table S1
    • (a) Narquizian, R.; Kocienski, P. J. In The Role of Natural Products in Drug Discovery; Mulzer, J., Bohlmann, R., Eds.; Ernst Schering Research Foundation Workshop 32; Springer: New York, 2000; pp 25-56. (b) See also Table S1.
    • (2000) The Role of Natural Products in Drug Discovery , pp. 25-56
    • Narquizian, R.1    Kocienski, P.J.2
  • 19
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    • note
    • SAR studies have revealed that a 5S,8S absolute configuration is required for the potent cytotoxicity observed for analogous pederin-like compounds (see Figure 1 for numbering and ref 10).
  • 20
    • 0035009212 scopus 로고    scopus 로고
    • (a) All reported members of the pederin family possess optical rotations ranging between [α] = +22 (onnamide F: Vuong, D.; Capon, R. J.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Nat. Prod. 2001, 64, 640-642) and [α] = +172 (theopederin C: Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828-3832). (b) See Table S1 for the optical rotations for all pederin metabolites.
    • (2001) J. Nat. Prod. , vol.64 , pp. 640-642
    • Vuong, D.1    Capon, R.J.2    Lacey, E.3    Gill, J.H.4    Heiland, K.5    Friedel, T.6
  • 21
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    • (b) See Table S1 for the optical rotations for all pederin metabolites
    • (a) All reported members of the pederin family possess optical rotations ranging between [α] = +22 (onnamide F: Vuong, D.; Capon, R. J.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Nat. Prod. 2001, 64, 640-642) and [α] = +172 (theopederin C: Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828-3832). (b) See Table S1 for the optical rotations for all pederin metabolites.
    • (1992) J. Org. Chem. , vol.57 , pp. 3828-3832
    • Fusetani, N.1    Sugawara, T.2    Matsunaga, S.3
  • 24
    • 3042768824 scopus 로고    scopus 로고
    • note
    • The name psymberin is derived from Psammocinia + symbiont + pederin in view of its relationship to the pederin family.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.